Page last updated: 2024-12-06

kaurenoic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Kaurenoic acid is a diterpenoid compound found in various plants, particularly in the genus _Salvia_. It is a precursor to gibberellins, a class of plant hormones crucial for stem elongation, seed germination, and flower development. Kaurenoic acid's biosynthesis pathway involves the cyclization of geranylgeranyl pyrophosphate (GGPP) through a series of enzymatic reactions. The compound exhibits various biological activities, including anti-inflammatory, antioxidant, and antimicrobial properties. It has been studied for its potential therapeutic applications in conditions like cancer and Alzheimer's disease. Research interest in kaurenoic acid stems from its diverse biological roles, its potential as a lead compound for drug development, and its role in plant growth regulation.'

kaurenoic acid: isolated from leaves of Montanoa tomentosa; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ent-kaur-16-en-19-oic acid : An ent-kaurane diterpenoid that is ent-kauran-19-oic acid in which a double bond is present at position 16(17); exhibits anticancer and anti-HIV 1 activity. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

FloraRankFlora DefinitionFamilyFamily Definition
MontanoagenusA plant genus of the family ASTERACEAE. Steroidal activity has been observed in animals. Members of this genus contain sesquiterpene lactones such as tomentosin, OXEPINS such as zoapatanol, and kaurene type DITERPENES.[MeSH]AsteraceaeA large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH]
MontanoagenusA plant genus of the family ASTERACEAE. Steroidal activity has been observed in animals. Members of this genus contain sesquiterpene lactones such as tomentosin, OXEPINS such as zoapatanol, and kaurene type DITERPENES.[MeSH]AsteraceaeA large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH]

Cross-References

ID SourceID
PubMed CID73062
CHEMBL ID489140
CHEBI ID15417
SCHEMBL ID21803663
MeSH IDM0146404
PubMed CID3034087
CHEMBL ID523791
MeSH IDM0146404

Synonyms (47)

Synonym
(5beta,8alpha,9beta,10alpha,13alpha)-kaur-16-en-18-oic acid
CHEBI:15417 ,
kauren-19-oic acid
(-)-kaur-16-en-19-oic acid
kaur-16-en-18-oic acid
kaurenic acid
ent-kaurenoic acid
ent-kaur-16(17)-en-19-oic acid
(1s,9s,5r,13r)-5,9-dimethyl-14-methylenetetracyclo[11.2.1.0<1,10>.0<4,9>]hexadecane-5-carboxylic acid
kaur-16-en-18-oic acid, (4alpha)-
nsc 339145
S9439
unii-d572d9r2tz
ent-kaur-16-en-18-oic acid
3beta-hydroxy-kaurenoic acid
kaurenoicacid
(4r,4as,6as,9r,11ar,11bs)-4,11b-dimethyl-8-methylenetetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid
CHEMBL489140
AKOS026674268
kaurenoic acid, >=95% (lc/ms-elsd)
SCHEMBL21803663
(4r,4as,6as,9s,11ar,11bs)-4,11b-dimethyl-8-methylenetetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid
Q27089430
NIKHGUQULKYIGE-OTCXFQBHSA-N
CS-0016962
HY-N1469
CCG-267494
kaurenoate
AS-56534
bdbm50466103
ne4 ,
(8alpha,9beta,10alpha,13alpha)-kaur-16-en-18-oic acid
cunabic acid
nsc-339145
ent-kaur-16-en-19-oic acid
6730-83-2
kaurenoic acid
ccris 1514
CHEMBL523791
LMPR0104130004
d572d9r2tz ,
bdbm50370742
NIKHGUQULKYIGE-SHAPNJEPSA-N
AKOS037515278
DTXSID801024912
1481688-54-3
(4alpha)-kaur-16-en-18-oic acid

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"Acetaminophen (paracetamol) is a widely used analgesic and antipyretic drug that is safe at therapeutic doses."( Kaurenoic acid extracted from Sphagneticola trilobata reduces acetaminophen-induced hepatotoxicity through inhibition of oxidative stress and pro-inflammatory cytokine production in mice.
Arakawa, NS; Borghi, SM; Bussmann, AJC; Casagrande, R; Fattori, V; Hirooka, EY; Lourenco-Gonzalez, Y; Marcondes-Alves, L; Verri, WA, 2019
)
0.51

Pharmacokinetics

ExcerptReferenceRelevance
" However, there are no pharmacokinetic data available about this molecule."( Pharmacokinetic profile and oral bioavailability of Kaurenoic acid from Copaifera spp. in rats.
Alvim, MCO; Carvalho, LSA; Da Silva Filho, AA; Leite, LHR; Matos, DM; Nascimento, JWL; Viana, MR, 2018
)
0.48

Bioavailability

ExcerptReferenceRelevance
" The purpose of the study was to determine the pharmacokinetic profile and the oral bioavailability of KA in rats."( Pharmacokinetic profile and oral bioavailability of Kaurenoic acid from Copaifera spp. in rats.
Alvim, MCO; Carvalho, LSA; Da Silva Filho, AA; Leite, LHR; Matos, DM; Nascimento, JWL; Viana, MR, 2018
)
0.48

Dosage Studied

ExcerptRelevanceReference
" The four diterpene acids dosed at 25 approximately 100 mg/kg had dose-dependently anti-asthmatic effects: 7-oxo-sandaracopimaric acid > 17-hydroxy-ent-kaur-15-en-19-oic acid > kaurenoic acid > hederagenin."( Inhibitory effects of diterpene acids from root of Aralia cordata on IgE-mediated asthma in guinea pigs.
Cho, JH; Kim, CJ; Lee, JY; Sim, SS; Whang, WK, 2010
)
0.36
" trilobata, for subsequent use in the quality control of dosage forms."( Development and validation of a stability indicative HPLC-PDA method for kaurenoic acid in spray dried extracts of Sphagneticola trilobata (L.) Pruski, Asteraceae.
Baccarin, T; Block, LC; Bresolin, TM; Filho, VC; Fucina, G; Quintão, NL; Ribeiro, TR; Silva, RM, 2012
)
0.38
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
anti-HIV-1 agentAn anti-HIV agent that destroys or inhibits the replication of HIV-1, the more infective and more virulent of the two types of HIV virus.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
ent-kaurane diterpenoidA diterpenoid compound having an ent-kaurane skeleton.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (2)

PathwayProteinsCompounds
Gibberellin A12 biosynthesis07
GA12 biosynthesis112

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Tyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)IC50 (µMol)20.20000.00053.49849.7600AID266456
Corticosteroid 11-beta-dehydrogenase isozyme 1Mus musculus (house mouse)IC50 (µMol)0.35700.00200.24103.7600AID758689
Corticosteroid 11-beta-dehydrogenase isozyme 2Mus musculus (house mouse)IC50 (µMol)500.00000.08200.14400.2060AID758690
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (27)

Processvia Protein(s)Taxonomy
positive regulation of JUN kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
actin cytoskeleton organizationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of endocytosisTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of vascular endothelial growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulum unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of intracellular protein transportTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cellular response to unfolded proteinTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
platelet-derived growth factor receptor-beta signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor recyclingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of MAP kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of type I interferon-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
growth hormone receptor signaling pathway via JAK-STATTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of protein tyrosine kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of ERK1 and ERK2 cascadeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of hepatocyte growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of endoplasmic reticulum stress-induced intrinsic apoptotic signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of PERK-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylation involved in inactivation of protein kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of receptor catabolic processTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
RNA bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
zinc ion bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
enzyme bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
receptor tyrosine kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cadherin bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
ephrin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein phosphatase 2A bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
non-membrane spanning protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
plasma membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial matrixTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytosolTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial cristaTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endosome lumenTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
sorting endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmic side of endoplasmic reticulum membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein-containing complexTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (159)

Assay IDTitleYearJournalArticle
AID426145Antituberculosis activity against Mycobacterium tuberculosis H37Rv assessed as parasite growth inhibition at 25 ug/ml after 4 days by microplate alamar blue assay2009Journal of natural products, Jul, Volume: 72, Issue:7
Macrophyllin-type bicyclo[3.2.1]octanoid neolignans from the leaves of Pleurothyrium cinereum.
AID734082Selectivity index, ratio of CC50 for human HepG2 cells to IC50 for chloroquine-resistant Plasmodium falciparum W2 infected in human erythrocytes2013European journal of medicinal chemistry, Apr, Volume: 62Synthesis, cytotoxicity and antiplasmodial activity of novel ent-kaurane derivatives.
AID426150Antibacterial activity against Salmonella Typhimurium MS 7953 by radial diffusion assay2009Journal of natural products, Jul, Volume: 72, Issue:7
Macrophyllin-type bicyclo[3.2.1]octanoid neolignans from the leaves of Pleurothyrium cinereum.
AID357845Binding affinity to calf thymus DNA assessed as reduction in DNA peak by pre-incubation method
AID669309Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as gated cells in upper right quadrant at 400 uM after 3 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 1.40%)2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID707336Antiinflammatory activity in complete Freund's adjuvant-induced Swiss mouse pain model assessed as inhibition of paw flinching at 10 mg/kg, po administered 30 mins prior to challenge2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID357846Binding affinity to yeast tRNA assessed as reduction in tRNA peak by pre-incubation method
AID707334Antihyperalgesic activity in po dosed carrageenan-induced mechanical hyperalgesia Swiss mouse model assessed as paw withdrawal latency administered 30 mins prior to challenge by electronic pressure-meter test2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID336447Antiplatelet activity against washed rabbit platelet assessed as inhibition of arachidonic acid-induced platelet aggregation at 200 uM2002Journal of natural products, Oct, Volume: 65, Issue:10
New ent-kaurane diterpenoids with anti-platelet aggregation activity from Annona squamosa.
AID1683372Antischistosomal activity against male Schistosoma mansoni BH assessed as dilation of testes at 25 uM after 72 hrs microscopic method
AID707134Antiinflammatory activity in Swiss mouse model assessed as inhibition of carrageenan-induced IL-1beta production in cutaneous plantar tissue at 10 mg/kg, po administered 30 mins prior to challenge measured 3 hrs post challenge by ELISA2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID707135Antiinflammatory activity in Swiss mouse model assessed as inhibition of carrageenan-induced TNFalpha production in cutaneous plantar tissue at 10 mg/kg, po administered 30 mins prior to challenge measured 3 hrs post challenge by ELISA2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID669314Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as gated cells in upper left quadrant at 400 uM after 3 hrs by rhodamine 123 staining-based flow cytometric analysis (Rvb = 1.54%)2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID426147Antibacterial activity against Enterococcus faecalis ATCC 29212 by radial diffusion assay2009Journal of natural products, Jul, Volume: 72, Issue:7
Macrophyllin-type bicyclo[3.2.1]octanoid neolignans from the leaves of Pleurothyrium cinereum.
AID707126Antihyperalgesic activity in carrageenan-induced mechanical hyperalgesia Swiss mouse model assessed as paw withdrawal latency at 10 mg/kg, po administered 30 mins prior to challenge measured after 1 to 5 hrs post challenge by electronic pressure-meter tes2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID1169836Antiinflammatory activity in human PBMC assessed as inhibition of LPS-induced IL-1beta expression pretreated 1 hr before LPS challenge followed by incubated for 16 hrs by flow cytometry2014Journal of natural products, Nov-26, Volume: 77, Issue:11
Anti-inflammatory diterpenoids from the root bark of Acanthopanax gracilistylus.
AID707123Antihyperalgesic activity against thermal hyperalgesia in Swiss mouse assessed as increase in thermal nociceptive threshold at 10 mg/kg, po after 1.5 to 5.5 hrs by hot plate test2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID707338Antinociceptive activity against formalin-induced pain in Swiss mouse assessed as inhibition of paw flinching at 10 mg/kg, po administered 30 mins prior to formalin challenge2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID758685Inhibition of human 11beta-HSD1 expressed in HEK293 cell microsomes assessed as inhibition of [3H]cortisone conversion to [3H]cortisol at 1 uM by scintillation proximity assay2013European journal of medicinal chemistry, Jul, Volume: 65Discovery and structure-activity relationships of ent-Kaurene diterpenoids as potent and selective 11β-HSD1 inhibitors: potential impact in diabetes.
AID1683379Cytotoxicity against human SH-SY5Y cells assessed as reduction in cell viability after 48 hrs by MTT assay
AID734086Growth inhibition against human IGROV cells after 72 hrs by inverted microscopy2013European journal of medicinal chemistry, Apr, Volume: 62Synthesis, cytotoxicity and antiplasmodial activity of novel ent-kaurane derivatives.
AID1417119Antileishmanial activity against Leishmania amazonensis WHOM/BR/75/Josefa promastigotes after 72 hrs by Neubauer chamber method2018European journal of medicinal chemistry, Sep-05, Volume: 157Natural products as inhibitors of Leishmania major dihydroorotate dehydrogenase.
AID707343Antinociceptive activity in Swiss mouse assessed as inhibition of acetic acid-induced writhing at 3 to 30 mg/kg, ip administered 30 mins prior to acetic acid challenge2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID707133Antihyperalgesic activity in PGE2-induced mechanical hyperalgesia Swiss mouse model assessed as paw withdrawal latency at 10 mg/kg, po administered 30 mins prior to challenge measured at 3 hrs post compound treatment by electronic pressure-meter test2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID758688Inhibition of human 11beta-HSD1 expressed in HEK293 cell microsomes assessed as inhibition of [3H]cortisone conversion to [3H]cortisol by scintillation proximity assay2013European journal of medicinal chemistry, Jul, Volume: 65Discovery and structure-activity relationships of ent-Kaurene diterpenoids as potent and selective 11β-HSD1 inhibitors: potential impact in diabetes.
AID707337Antinociceptive activity against formalin-induced pain in Swiss mouse assessed as inhibition of paw licking at 10 mg/kg, po administered 30 mins prior to formalin challenge2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID669300Cytotoxicity against monkey LLC-MK2 cells after 96 hrs by sulforhodamine B assay2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID354581Toxicity against brine shrimp1996Journal of natural products, Mar, Volume: 59, Issue:3
Bioactive ent-kaurene diterpenoids from Annona senegalensis.
AID1417094Inhibition of recombinant oligo-histidine-tagged Leishmania major DHODH expressed in Escherichia coli BL21(DE3) cells using DHO as substrate measured after 60 secs2018European journal of medicinal chemistry, Sep-05, Volume: 157Natural products as inhibitors of Leishmania major dihydroorotate dehydrogenase.
AID1683377Cytotoxicity against human HaCaT cells assessed as reduction in cell viability after 48 hrs by MTT assay
AID707117Gastrointestinal toxicity in Swiss mouse assessed as increase in stomach MPO activity at at 10 mg/kg, po for 7 days measured over 7 days relative to vehicle-treated control2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID734088Growth inhibition against human K562 cells after 72 hrs by inverted microscopy2013European journal of medicinal chemistry, Apr, Volume: 62Synthesis, cytotoxicity and antiplasmodial activity of novel ent-kaurane derivatives.
AID1683371Antischistosomal activity against female Schistosoma mansoni BH assessed as dilation of ovaries at 25 uM after 72 hrs microscopic method
AID284140Induction of total haemolysis in Albino mouse blood infected with Trypanosoma cruzi Y at 5 mM2007Bioorganic & medicinal chemistry, Jan-01, Volume: 15, Issue:1
Synthesis and trypanocidal activity of ent-kaurane glycosides.
AID669307Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as gated cells in lower left quadrant at 400 uM after 3 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 89.35%)2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID426151Antibacterial activity against Salmonella Typhimurium EG10627 by radial diffusion assay2009Journal of natural products, Jul, Volume: 72, Issue:7
Macrophyllin-type bicyclo[3.2.1]octanoid neolignans from the leaves of Pleurothyrium cinereum.
AID707335Antiinflammatory activity in complete Freund's adjuvant-induced Swiss mouse pain model assessed as inhibition of paw licking at 10 mg/kg, po administered 30 mins prior to challenge2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID758687selectivity ratio of IC50 for human 11beta-HSD2 to IC50 for human 11beta-HSD12013European journal of medicinal chemistry, Jul, Volume: 65Discovery and structure-activity relationships of ent-Kaurene diterpenoids as potent and selective 11β-HSD1 inhibitors: potential impact in diabetes.
AID669299Antitrypanosomal activity against Trypanosoma cruzi Y amastigotes infected in monkey LLC-MK2 cells after 96 hrs by Geimsa staining method2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID707121Hepatotoxicity in Swiss mouse assessed as change in plasma AST level at 10 mg/kg, po for 7 days measured over 7 days relative to vehicle-treated control2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID354583Cytotoxicity against human MCF7 cells after 7 days by MTT assay1996Journal of natural products, Mar, Volume: 59, Issue:3
Bioactive ent-kaurene diterpenoids from Annona senegalensis.
AID758689Inhibition of mouse 11beta-HSD1 expressed in HEK293 cell microsomes assessed as inhibition of [3H]cortisone conversion to [3H]cortisol by scintillation proximity assay2013European journal of medicinal chemistry, Jul, Volume: 65Discovery and structure-activity relationships of ent-Kaurene diterpenoids as potent and selective 11β-HSD1 inhibitors: potential impact in diabetes.
AID1169837Antiinflammatory activity in human PBMC assessed as inhibition of LPS-induced IL-8 expression pretreated 1 hr before LPS challenge followed by incubated for 16 hrs by flow cytometry2014Journal of natural products, Nov-26, Volume: 77, Issue:11
Anti-inflammatory diterpenoids from the root bark of Acanthopanax gracilistylus.
AID707127Antihyperalgesic activity in carrageenan-induced mechanical hyperalgesia Swiss mouse model assessed as paw withdrawal latency at 10 mg/kg, po administered 30 mins prior to challenge measured after 1 to 5 hrs post challenge by electronic pressure-meter tes2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID1684121Inhibition of NF-kappaB activation in mouse RaW264.7 cells assessed as reduction in LPS-induced NO production after 24 hrs by Griess reagent based assay2020Journal of natural products, 12-24, Volume: 83, Issue:12
3α-Angeloyloxy-
AID758684Inhibition of mouse 11beta-HSD1 expressed in HEK293 cell microsomes assessed as inhibition of [3H]cortisone conversion to [3H]cortisol at 1 uM by scintillation proximity assay2013European journal of medicinal chemistry, Jul, Volume: 65Discovery and structure-activity relationships of ent-Kaurene diterpenoids as potent and selective 11β-HSD1 inhibitors: potential impact in diabetes.
AID669296Antitrypanosomal activity against Trypanosoma cruzi Y infected in monkey LLC-MK2 cells assessed as reduction in number of amastigotes after 96 hrs by Geimsa staining method2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID589274Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide release pretreated for 15 mins before LPS challenge measured after 24 hrs by Griess method2011European journal of medicinal chemistry, Apr, Volume: 46, Issue:4
Synthesis and anti-inflammatory activity of ent-kaurene derivatives.
AID734081Cytotoxicity against human HepG2 cells after 24 hrs by MTT assay2013European journal of medicinal chemistry, Apr, Volume: 62Synthesis, cytotoxicity and antiplasmodial activity of novel ent-kaurane derivatives.
AID284134Trypanocidal activity against Trypanosoma cruzi Y blood stream trypomastigotes assessed as parasite lysis at 2.50 mM relative to control2007Bioorganic & medicinal chemistry, Jan-01, Volume: 15, Issue:1
Synthesis and trypanocidal activity of ent-kaurane glycosides.
AID669301Toxicity in human RBC assessed as hemolysis after 3 hrs2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID707138Antihyperalgesic activity in complete Freund's adjuvant-induced Swiss mouse pain model assessed as paw withdrawal latency at 10 mg/kg, po starting 1 hr post challenge for 7 days measured after 2 to 7 days by electronic pressure-meter test2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID758690Inhibition of mouse 11beta-HSD22013European journal of medicinal chemistry, Jul, Volume: 65Discovery and structure-activity relationships of ent-Kaurene diterpenoids as potent and selective 11β-HSD1 inhibitors: potential impact in diabetes.
AID707331Antihyperalgesic activity in carrageenan-induced mechanical hyperalgesia Swiss mouse model assessed as paw withdrawal latency at 10 mg/kg, po administered 30 mins prior to challenge measured after 1 to 5 hrs post stimulus by electronic pressure-meter test2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID426149Antibacterial activity against Salmonella Typhimurium ATCC 14028s by radial diffusion assay2009Journal of natural products, Jul, Volume: 72, Issue:7
Macrophyllin-type bicyclo[3.2.1]octanoid neolignans from the leaves of Pleurothyrium cinereum.
AID707332Antihyperalgesic activity in carrageenan-induced mechanical hyperalgesia Swiss mouse model assessed as paw withdrawal latency at 3 mg/kg, po administered 30 mins prior to challenge measured after 1 to 3 hrs post stimulus by electronic pressure-meter test2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID734084Growth inhibition against human LoVo cells after 72 hrs by inverted microscopy2013European journal of medicinal chemistry, Apr, Volume: 62Synthesis, cytotoxicity and antiplasmodial activity of novel ent-kaurane derivatives.
AID1103177Antifungal activity against Botryotinia fuckeliana inoculated in tomato leaf assessed as reduction in lesion area at 40 ug/ml after 4 days (Rvb =9.7 +/- 1.8 mm2 )2004Journal of agricultural and food chemistry, May-19, Volume: 52, Issue:10
Characterization of the antifungal activity on Botrytis cinerea of the natural diterpenoids kaurenoic acid and 3beta-hydroxy-kaurenoic acid.
AID707333Antihyperalgesic activity in carrageenan-induced mechanical hyperalgesia Swiss mouse model assessed as paw withdrawal latency at 1 mg/kg, po administered 30 mins prior to challenge by electronic pressure-meter test2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID336450Antiplatelet activity against washed rabbit platelet assessed as inhibition of thrombin-induced platelet aggregation at 200 uM2002Journal of natural products, Oct, Volume: 65, Issue:10
New ent-kaurane diterpenoids with anti-platelet aggregation activity from Annona squamosa.
AID1103182Antifungal activity against Botryotinia fuckeliana assessed as inhibition of mycelial growth at 40 to 160 ug/ml up to 7 days2004Journal of agricultural and food chemistry, May-19, Volume: 52, Issue:10
Characterization of the antifungal activity on Botrytis cinerea of the natural diterpenoids kaurenoic acid and 3beta-hydroxy-kaurenoic acid.
AID1417120Antileishmanial activity against Leishmania amazonensis WHOM/BR/75/Josefa amastigotes after 72 hrs by Neubauer chamber method2018European journal of medicinal chemistry, Sep-05, Volume: 157Natural products as inhibitors of Leishmania major dihydroorotate dehydrogenase.
AID354587Cytotoxicity against human MIAPaCa2 cells after 7 days by MTT assay1996Journal of natural products, Mar, Volume: 59, Issue:3
Bioactive ent-kaurene diterpenoids from Annona senegalensis.
AID669311Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as gated cells in lower left quadrant at 400 uM after 3 hrs by rhodamine 123 staining-based flow cytometric analysis (Rvb = 2.40%)2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID1683381Antischistosomal activity against Schistosoma mansoni BH assessed as reduction in parasitic viability inverted light microscopic method
AID669298Antitrypanosomal activity against Trypanosoma cruzi Y trymastigotes infected in monkey LLC-MK2 cells after 24 hrs by Brenner counter method2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID758691Selectivity ratio of IC50 for mouse 11beta-HSD2 to IC50 for mouse 11beta-HSD12013European journal of medicinal chemistry, Jul, Volume: 65Discovery and structure-activity relationships of ent-Kaurene diterpenoids as potent and selective 11β-HSD1 inhibitors: potential impact in diabetes.
AID1103180Antifungal activity against Botryotinia fuckeliana assessed as reduction in mycelial growth rate at 40 to 160 ug/ml up to 9 days (Rvb = 1.82 cm/day)2004Journal of agricultural and food chemistry, May-19, Volume: 52, Issue:10
Characterization of the antifungal activity on Botrytis cinerea of the natural diterpenoids kaurenoic acid and 3beta-hydroxy-kaurenoic acid.
AID707342Antinociceptive activity in po dosed Swiss mouse assessed as inhibition of acetic acid-induced writhing administered 30 mins prior to acetic acid challenge2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID284138Induction of total haemolysis in Albino mouse blood infected with Trypanosoma cruzi Y at 1.25 mM2007Bioorganic & medicinal chemistry, Jan-01, Volume: 15, Issue:1
Synthesis and trypanocidal activity of ent-kaurane glycosides.
AID1181215Cytotoxicity against human K562 cells after 72 hrs by alamar blue assay2014Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15
ent-Kaurane diterpenes from the stem bark of Annona vepretorum (Annonaceae) and cytotoxic evaluation.
AID669313Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as gated cells in upper right quadrant at 400 uM after 3 hrs by rhodamine 123 staining-based flow cytometric analysis (Rvb = 94.94%)2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID266456Inhibition of human recombinant PTP1B2006Bioorganic & medicinal chemistry letters, Jun-01, Volume: 16, Issue:11
Inhibition of protein tyrosine phosphatase 1B by diterpenoids isolated from Acanthopanax koreanum.
AID354585Cytotoxicity against human A498 cells after 7 days by MTT assay1996Journal of natural products, Mar, Volume: 59, Issue:3
Bioactive ent-kaurene diterpenoids from Annona senegalensis.
AID669302Selectivity ratio of CC50 for monkey LLC-MK2 cells to IC50 for Trypanosoma cruzi Y amastigotes2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID707341Antinociceptive activity in Swiss mouse assessed as inhibition of PBQ-induced writhing at 10 mg/kg, po administered 30 mins prior to PBQ challenge2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID1103176Antifungal activity against Botryotinia fuckeliana grown assessed as membrane leakage measuring efflux of phosphorus at 100 ug/ml after 6 hr by ICP-OES analysis2004Journal of agricultural and food chemistry, May-19, Volume: 52, Issue:10
Characterization of the antifungal activity on Botrytis cinerea of the natural diterpenoids kaurenoic acid and 3beta-hydroxy-kaurenoic acid.
AID1103173Antifungal activity against Botryotinia fuckeliana grown assessed as induction of production of p-nitrophenyl butyrate esterase after 20 days relative to control2004Journal of agricultural and food chemistry, May-19, Volume: 52, Issue:10
Characterization of the antifungal activity on Botrytis cinerea of the natural diterpenoids kaurenoic acid and 3beta-hydroxy-kaurenoic acid.
AID734495Growth inhibition against human LoVo/DX cells after 72 hrs by inverted microscopy2013European journal of medicinal chemistry, Apr, Volume: 62Synthesis, cytotoxicity and antiplasmodial activity of novel ent-kaurane derivatives.
AID1683380Selectivity index, ratio of CC50 for cytotoxicity against human SH-SY5Y cells to LC50 for antischistosomal activity against Schistosoma mansoni BH
AID734085Growth inhibition against human HeLa cells after 72 hrs by inverted microscopy2013European journal of medicinal chemistry, Apr, Volume: 62Synthesis, cytotoxicity and antiplasmodial activity of novel ent-kaurane derivatives.
AID1181216Cytotoxicity against concanavalin-A stimulated human PBMC after 72 hrs by alamar blue assay2014Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15
ent-Kaurane diterpenes from the stem bark of Annona vepretorum (Annonaceae) and cytotoxic evaluation.
AID376818Inhibition of HIV reverse transcriptase at 33 ug/mL by scintillation counting1998Journal of natural products, Apr, Volume: 61, Issue:4
Bioactive kaurane diterpenoids from Annona glabra.
AID734087Growth inhibition against human IGROV-ET cells after 72 hrs by inverted microscopy2013European journal of medicinal chemistry, Apr, Volume: 62Synthesis, cytotoxicity and antiplasmodial activity of novel ent-kaurane derivatives.
AID426146Antibacterial activity against Staphylococcus aureus ATCC 65380 by radial diffusion assay2009Journal of natural products, Jul, Volume: 72, Issue:7
Macrophyllin-type bicyclo[3.2.1]octanoid neolignans from the leaves of Pleurothyrium cinereum.
AID1169838Antiinflammatory activity in human PBMC assessed as inhibition of LPS-induced TNFalpha expression pretreated 1 hr before LPS challenge followed by incubated for 16 hrs by flow cytometry2014Journal of natural products, Nov-26, Volume: 77, Issue:11
Anti-inflammatory diterpenoids from the root bark of Acanthopanax gracilistylus.
AID336448Antiplatelet activity against washed rabbit platelet assessed as inhibition of collagen-induced platelet aggregation at 200 uM2002Journal of natural products, Oct, Volume: 65, Issue:10
New ent-kaurane diterpenoids with anti-platelet aggregation activity from Annona squamosa.
AID354584Cytotoxicity against human HT29 cells after 7 days by MTT assay1996Journal of natural products, Mar, Volume: 59, Issue:3
Bioactive ent-kaurene diterpenoids from Annona senegalensis.
AID1181212Cytotoxicity against mouse B16F10 cells after 72 hrs by alamar blue assay2014Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15
ent-Kaurane diterpenes from the stem bark of Annona vepretorum (Annonaceae) and cytotoxic evaluation.
AID669312Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as gated cells in lower right quadrant at 400 uM after 3 hrs by rhodamine 123 staining-based flow cytometric analysis (Rvb = 1.12%)2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID669310Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as gated cells in upper left quadrant at 400 uM after 3 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 3.76%)2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID1683375Antischistosomal activity against Schistosoma mansoni BH assessed as reduction in parasitic viability at 25 uM after 24 hrs inverted light microscopic method
AID707124Toxicity in Swiss mouse assessed as effect on muscle-relaxing effect at 10 mg/kg, po after 1.5 to 5.5 hrs by roto-rod test2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID354586Cytotoxicity against human PC3 cells after 7 days by MTT assay1996Journal of natural products, Mar, Volume: 59, Issue:3
Bioactive ent-kaurene diterpenoids from Annona senegalensis.
AID336449Antiplatelet activity against washed rabbit platelet assessed as inhibition of platelet activating factor-induced platelet aggregation at 200 uM2002Journal of natural products, Oct, Volume: 65, Issue:10
New ent-kaurane diterpenoids with anti-platelet aggregation activity from Annona squamosa.
AID284135Trypanocidal activity against blood stream Trypanosoma cruzi Y trypomastigotes assessed as parasite lysis at 5 mM relative to control2007Bioorganic & medicinal chemistry, Jan-01, Volume: 15, Issue:1
Synthesis and trypanocidal activity of ent-kaurane glycosides.
AID1683378Selectivity index, ratio of CC50 for cytotoxicity against human HaCaT cells to LC50 for antischistosomal activity against Schistosoma mansoni BH
AID707132Antihyperalgesic activity in carrageenan-induced mechanical hyperalgesia Swiss mouse model assessed as paw withdrawal latency at 10 mg/kg, po administered 30 mins prior to challenge measured after 1 to 5 hrs post challenge by electronic pressure-meter tes2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID707136Antihyperalgesic activity in complete Freund's adjuvant-induced Swiss mouse pain model assessed as paw withdrawal latency at 5 mg/kg, ip starting 1 hr post challenge for 7 days measured after 2 to 7 days by electronic pressure-meter test2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID1181214Cytotoxicity against human HL60 cells after 72 hrs by alamar blue assay2014Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15
ent-Kaurane diterpenes from the stem bark of Annona vepretorum (Annonaceae) and cytotoxic evaluation.
AID1417091Inhibition of human DHODH at 100 uM2018European journal of medicinal chemistry, Sep-05, Volume: 157Natural products as inhibitors of Leishmania major dihydroorotate dehydrogenase.
AID734083Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 infected in human erythrocytes assessed as inhibition of parasite growth after 24 hrs by [3H]hypoxanthine incorporation assay2013European journal of medicinal chemistry, Apr, Volume: 62Synthesis, cytotoxicity and antiplasmodial activity of novel ent-kaurane derivatives.
AID707131Antihyperalgesic activity in carrageenan-induced mechanical hyperalgesia Swiss mouse model assessed as paw withdrawal latency at 10 mg/kg, po administered 30 mins prior to challenge measured after 1 to 5 hrs post challenge by electronic pressure-meter tes2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID284132Trypanocidal activity against Trypanosoma cruzi Y blood stream trypomastigotes assessed as parasite lysis at 0.63 mM relative to control2007Bioorganic & medicinal chemistry, Jan-01, Volume: 15, Issue:1
Synthesis and trypanocidal activity of ent-kaurane glycosides.
AID1417093Inhibition of recombinant oligo-histidine-tagged Leishmania major DHODH expressed in Escherichia coli BL21(DE3) cells at 100 uM using DHO as substrate measured after 60 secs2018European journal of medicinal chemistry, Sep-05, Volume: 157Natural products as inhibitors of Leishmania major dihydroorotate dehydrogenase.
AID426074Antituberculosis activity against Mycobacterium tuberculosis H37Rv assessed as parasite growth inhibition at 100 ug/ml after 4 days by microplate alamar blue assay2009Journal of natural products, Jul, Volume: 72, Issue:7
Macrophyllin-type bicyclo[3.2.1]octanoid neolignans from the leaves of Pleurothyrium cinereum.
AID707137Antihyperalgesic activity in complete Freund's adjuvant-induced Swiss mouse pain model assessed as paw withdrawal latency at 10 mg/kg, po starting 1 hr post challenge for 7 days measured on day 1 post challenge by electronic pressure-meter test2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID734089Growth inhibition against human PANC1 cells after 72 hrs by inverted microscopy2013European journal of medicinal chemistry, Apr, Volume: 62Synthesis, cytotoxicity and antiplasmodial activity of novel ent-kaurane derivatives.
AID707128Antihyperalgesic activity in carrageenan-induced mechanical hyperalgesia Swiss mouse model assessed as paw withdrawal latency at 10 mg/kg, po administered 30 mins prior to challenge measured after 1 to 5 hrs post challenge by electronic pressure-meter tes2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID1181213Cytotoxicity against human HepG2 cells after 72 hrs by alamar blue assay2014Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15
ent-Kaurane diterpenes from the stem bark of Annona vepretorum (Annonaceae) and cytotoxic evaluation.
AID284133Trypanocidal activity against Trypanosoma cruzi Y blood stream trypomastigotes assessed as parasite lysis at 1.25 mM relative to control2007Bioorganic & medicinal chemistry, Jan-01, Volume: 15, Issue:1
Synthesis and trypanocidal activity of ent-kaurane glycosides.
AID669308Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as gated cells in lower right quadrant at 400 uM after 3 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 5.41%)2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID426075Antituberculosis activity against Mycobacterium tuberculosis H37Rv assessed as parasite growth inhibition at 50 ug/ml after 4 days by microplate alamar blue assay2009Journal of natural products, Jul, Volume: 72, Issue:7
Macrophyllin-type bicyclo[3.2.1]octanoid neolignans from the leaves of Pleurothyrium cinereum.
AID707125Toxicity in Swiss mouse assessed as sedative effect at 10 mg/kg, po after 1.5 to 5.5 hrs by roto-rod test2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID1683376Antischistosomal activity against Schistosoma mansoni BH assessed as reduction in parasitic viability after 72 hrs by inverted microscopic method
AID1683373Antischistosomal activity against Schistosoma mansoni BH assessed as reduction in oviposition at 25 uM after 72 hrs light microscopic method
AID669297Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes after 96 hrs by neubauer chamber2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID458882Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viability after 24 hrs by MTT assay2010Bioorganic & medicinal chemistry, Feb-15, Volume: 18, Issue:4
Synthesis and induction of apoptosis signaling pathway of ent-kaurane derivatives.
AID707130Antihyperalgesic activity in carrageenan-induced mechanical hyperalgesia Swiss mouse model assessed as paw withdrawal latency at 10 mg/kg, po administered 30 mins prior to challenge measured after 1 to 5 hrs post challenge by electronic pressure-meter tes2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID354582Cytotoxicity against human A549 cells after 7 days by MTT assay1996Journal of natural products, Mar, Volume: 59, Issue:3
Bioactive ent-kaurene diterpenoids from Annona senegalensis.
AID758686Inhibition of human 11beta-HSD22013European journal of medicinal chemistry, Jul, Volume: 65Discovery and structure-activity relationships of ent-Kaurene diterpenoids as potent and selective 11β-HSD1 inhibitors: potential impact in diabetes.
AID1103179Antifungal activity against Botryotinia fuckeliana grown in malt-yeast extract medium assessed as inhibition of mycelial growth at 40 to 160 ug/ml2004Journal of agricultural and food chemistry, May-19, Volume: 52, Issue:10
Characterization of the antifungal activity on Botrytis cinerea of the natural diterpenoids kaurenoic acid and 3beta-hydroxy-kaurenoic acid.
AID1103172Antifungal activity against Botryotinia fuckeliana grown assessed as induction of production of laccase after 10 days relative to control2004Journal of agricultural and food chemistry, May-19, Volume: 52, Issue:10
Characterization of the antifungal activity on Botrytis cinerea of the natural diterpenoids kaurenoic acid and 3beta-hydroxy-kaurenoic acid.
AID669306Antitrypanosomal activity against Trypanosoma cruzi Y epimastigotes assessed as lipid peroxidation at 400 uM after 6 hrs2012Journal of medicinal chemistry, Apr-12, Volume: 55, Issue:7
Terpenes from Copaifera demonstrated in vitro antiparasitic and synergic activity.
AID426148Antibacterial activity against Escherichia coli ATCC 25922 by radial diffusion assay2009Journal of natural products, Jul, Volume: 72, Issue:7
Macrophyllin-type bicyclo[3.2.1]octanoid neolignans from the leaves of Pleurothyrium cinereum.
AID707129Antihyperalgesic activity in carrageenan-induced mechanical hyperalgesia Swiss mouse model assessed as paw withdrawal latency at 10 mg/kg, po administered 30 mins prior to challenge measured after 1 to 5 hrs post challenge by electronic pressure-meter tes2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID284131Trypanocidal activity against Trypanosoma cruzi Y blood stream trypomastigotes assessed as parasite lysis at 0.31 mM relative to control2007Bioorganic & medicinal chemistry, Jan-01, Volume: 15, Issue:1
Synthesis and trypanocidal activity of ent-kaurane glycosides.
AID1103183Antifungal activity against Botryotinia fuckeliana assessed as inhibition of mycelial growth at 40 to 160 ug/ml up to 6 days2004Journal of agricultural and food chemistry, May-19, Volume: 52, Issue:10
Characterization of the antifungal activity on Botrytis cinerea of the natural diterpenoids kaurenoic acid and 3beta-hydroxy-kaurenoic acid.
AID734494Growth inhibition against human HT-29 cells after 72 hrs by inverted microscopy2013European journal of medicinal chemistry, Apr, Volume: 62Synthesis, cytotoxicity and antiplasmodial activity of novel ent-kaurane derivatives.
AID284139Induction of total haemolysis in Albino mouse blood infected with Trypanosoma cruzi Y at 2.5 mM2007Bioorganic & medicinal chemistry, Jan-01, Volume: 15, Issue:1
Synthesis and trypanocidal activity of ent-kaurane glycosides.
AID589275Cytotoxicity against LPS-stimulated mouse RAW264.7 cells assessed as cell viability at 1 to 25 uM pretreated for 15 mins before LPS challenge measured after 24 hrs by MTT assay2011European journal of medicinal chemistry, Apr, Volume: 46, Issue:4
Synthesis and anti-inflammatory activity of ent-kaurene derivatives.
AID355092Antiviral activity against HIV1 3B replication in human H9 cells up to 100 ug/mL after 3 days by p24 antigen capture assay1996Journal of natural products, Jun, Volume: 59, Issue:6
Identification of ent-16 beta, 17-dihydroxykauran-19-oic acid as an anti-HIV principle and isolation of the new diterpenoids annosquamosins A and B from Annona squamosa.
AID707120Hepatotoxicity in Swiss mouse assessed as change in plasma ALT level at 10 mg/kg, po for 7 days measured over 7 days relative to vehicle-treated control2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID707115Antihyperalgesic activity in complete Freund's adjuvant-induced Swiss mouse pain model assessed as paw withdrawal latency at 5 mg/kg, ip starting 1 hr post challenge for 7 days measured on day 1 post challenge by electronic pressure-meter test2012Journal of natural products, May-25, Volume: 75, Issue:5
Kaurenoic acid from Sphagneticola trilobata Inhibits Inflammatory Pain: effect on cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
AID1447311Induction of apoptosis in human SMMC7721 cells assessed as late apoptotic cells at IC50 after 24 hrs by annexin V/PI-staining based flow cytometry (Rvb = 0.5 %)2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447310Induction of apoptosis in human SMMC7721 cells assessed as early apoptotic cells at IC50 after 24 hrs by annexin V/PI-staining based flow cytometry (Rvb = 0.6 %)2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447327Cell cycle arrest in human SMMC7721 cells assessed as G1 phase accumulation at half IC50 after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 57.6 %)2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447319Induction of apoptosis in human SMMC7721 cells assessed as increase in cleaved caspase 9 levels after 24 hrs by Western blot method2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447325Induction of apoptosis in human SMMC7721 cells assessed as necrotic cells at half IC50 after 24 hrs by annexin V/PI-staining based flow cytometry (Rvb =1.6 %)2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447323Induction of apoptosis in human SMMC7721 cells assessed as early apoptotic cells at half IC50 after 24 hrs by annexin V/PI-staining based flow cytometry (Rvb = 0.6 %)2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447312Induction of apoptosis in human SMMC7721 cells assessed as necrotic cells at IC50 after 24 hrs by annexin V/PI-staining based flow cytometry (Rvb =1.6 %)2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447320Induction of apoptosis in human SMMC7721 cells assessed as increase in Bax levels after 24 hrs by Western blot method2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447329Cell cycle arrest in human SMMC7721 cells assessed as G2/M phase accumulation at half IC50 after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 28.8 %)2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447324Induction of apoptosis in human SMMC7721 cells assessed as late apoptotic cells at half IC50 after 24 hrs by annexin V/PI-staining based flow cytometry (Rvb = 0.5 %)2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447315Cell cycle arrest in human SMMC7721 cells assessed as S phase accumulation at IC50 after 24 hrs by propidium iodide staining based flow cytometry (Rvb = 12.7 %)2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447316Cell cycle arrest in human SMMC7721 cells assessed as G2/M phase accumulation at IC50 after 24 hrs by propidium iodide staining based flow cytometry (Rvb = 28.8 %)2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447328Cell cycle arrest in human SMMC7721 cells assessed as S phase accumulation at half IC50 after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 12.7 %)2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447313Cell cycle arrest in human SMMC7721 cells assessed as sub-G1 phase accumulation at IC50 after 24 hrs by propidium iodide staining based flow cytometry (Rvb = 0.8 %)2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447317Induction of apoptosis in human SMMC7721 cells assessed as increase in cleaved caspase 3 levels after 24 hrs by Western blot method2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447318Induction of apoptosis in human SMMC7721 cells assessed as increase in cleaved caspase 8 levels after 24 hrs by Western blot method2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447322Induction of apoptosis in human SMMC7721 cells assessed as live cells at half IC50 after 24 hrs by annexin V/PI-staining based flow cytometry (Rvb = 97.3 %)2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447321Induction of apoptosis in human SMMC7721 cells assessed as decrease in Bcl2 levels after 24 hrs by Western blot method2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447314Cell cycle arrest in human SMMC7721 cells assessed as G1 phase accumulation at IC50 after 24 hrs by propidium iodide staining based flow cytometry (Rvb = 57.6 %)2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447332Induction of apoptosis in human SMMC7721 cells assessed as broken nuclei after 24 hrs by Hoechst 33258 staining based fluorescent microscopic method2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447308Induction of apoptosis in human SMMC7721 cells assessed as live cells at IC50 after 24 hrs by annexin V/PI-staining based flow cytometry (Rvb = 97.3 %)2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447330Induction of apoptosis in human SMMC7721 cells after 24 hrs by annexin V/PI-staining based flow cytometry2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447326Cell cycle arrest in human SMMC7721 cells assessed as sub-G1 phase accumulation at half IC50 after 24 hrs by propidium iodide-staining based flow cytometry (Rvb = 0.8 %)2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447331Induction of apoptosis in human SMMC7721 cells assessed as condensed nuclei after 24 hrs by Hoechst 33258 staining based fluorescent microscopic method2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
AID1447309Cytotoxicity against human SMMC7721 cells after 48 hrs by MTT assay2017Bioorganic & medicinal chemistry letters, 05-01, Volume: 27, Issue:9
Studies on anti-hepatoma activity of Annona squamosa L. pericarp extract.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (117)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (0.85)18.7374
1990's7 (5.98)18.2507
2000's34 (29.06)29.6817
2010's61 (52.14)24.3611
2020's14 (11.97)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.81

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index32.81 (24.57)
Research Supply Index3.04 (2.92)
Research Growth Index4.77 (4.65)
Search Engine Demand Index38.40 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (32.81)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other20 (100.00%)84.16%
Other106 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]