Page last updated: 2024-11-08

parthenin

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

Description

parthenin: sesqiterpene lactone from Parthenium hysterophorus; structure; RN given refers to 3aS-(3aalpha,6beta,6abeta,9abeta,9balpha)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
Partheniumgenusnull[CHeBI]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 CID442288
CHEMBL ID401149
CHEBI ID7938
SCHEMBL ID382003
MeSH IDM0077738

Synonyms (22)

Synonym
10-alpha-h-ambrosa-2,11(13)-dien-12-oic acid, 1,6-beta-dihydroxy-4-oxo-, gamma-lactone
(3as-(3aalpha,6beta,6aalpha,9abeta,9balpha))-3,3a,4,5,6,6a,9a,9b-octahydro-6a-hydroxy-6,9a-dimethyl-3-methyleneazuleno (4,5-b)furan-2,9-dione
10alphah-ambrosa-2,11(13)-dien-12-oic acid, 1,6beta-dihydroxy-4-oxo-, gamma-lactone
nsc 85239
azuleno(4,5-b)furan-2,9-dione, 3,3a,4,5,6,6a,9a,9b-octahydro-6a-hydroxy-6,9a-dimethyl-3-methylene-, (3as-(3aalpha,6beta,6aalpha,9abeta,9balpha))-
parthenin
508-59-8
C09523
LMPR0103420001
CHEMBL401149
chebi:7938 ,
(3as,6s,6as,9as,9br)-6a-hydroxy-6,9a-dimethyl-3-methylidene-4,5,6,9b-tetrahydro-3ah-azuleno[8,7-b]furan-2,9-dione
982djp4w6a ,
unii-982djp4w6a
partenin
SCHEMBL382003
azuleno(4,5-b)furan-2,9-dione, 3,3a,4,5,6,6a,9a,9b-octahydro-6a-hydroxy-6,9a-dimethyl-3-methylene-, (3as,6s,6as,9as,9br)-
10.alpha.h-ambrosa-2,11(13)-dien-12-oic acid, 1,6.beta.-dihydroxy-4-oxo-, .gamma.-lactone
parthenin [mi]
Q27107626
DTXSID40877834
azuleno[4,5-b]furan-2,9-dione, 3,3a,4,5,6,6a,9a,9b-octahydro-6a-hydroxy-6,9a-dimethyl-3-methylene-, (3as,6s,6as,9as,9br)-

Research Excerpts

Overview

Parthenin is a metabolite of Parthenium hysterophorus. It is believed to contribute to the weed's invasiveness via allelopathy.

ExcerptReferenceRelevance
"Parthenin is a metabolite of Parthenium hysterophorus and is believed to contribute to the weed's invasiveness via allelopathy. "( Investigating a Potential Auxin-Related Mode of Hormetic/Inhibitory Action of the Phytotoxin Parthenin.
Belz, RG, 2016
)
2.1

Dosage Studied

ExcerptRelevanceReference
"In the rabbit isolated aorta, hymenin (10(-6) M), a novel marine alkaloid, caused a parallel rightward shift of the dose-response curve for norepinephrine without affecting that for histamine or KCl, suggesting that hymenin is a competitive antagonist of alpha-adrenoceptors in vascular smooth muscles."( Alpha-adrenoceptor blocking action of hymenin, a novel marine alkaloid.
Kobayashi, J; Nakamura, H; Ohizumi, Y, 1988
)
0.27
" This biphasic action was hypothesized to be auxin-like and, therefore, an auxin-related mode of parthenin action was investigated using two approaches: joint action experiments with Lactuca sativa, and dose-response experiments with auxin/antiauxin-resistant Arabidopsis thaliana genotypes."( Investigating a Potential Auxin-Related Mode of Hormetic/Inhibitory Action of the Phytotoxin Parthenin.
Belz, RG, 2016
)
0.87
" We tested the response of Lactuca sativa in complete dose-response experiments to six different toxicants at doses that did not decrease population mean and beyond."( Low doses of six toxicants change plant size distribution in dense populations of Lactuca sativa.
Belz, RG; Patama, M; Sinkkonen, A, 2018
)
0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
sesquiterpene lactoneAny member of a diverse class of complex, multicyclic phytochemicals showing a variety of skeleton arrangements and bioactivities, and having in common a sesquiterpenoid structure including a lactone ring.
[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]

Bioassays (31)

Assay IDTitleYearJournalArticle
AID1155391Cytotoxicity against human HeLa cells after 48 hrs by sulforhodamine B assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design and synthesis of novel 1,2,3-triazole derivatives of coronopilin as anti-cancer compounds.
AID1155388Cytotoxicity against human THP1 cells after 48 hrs by sulforhodamine B assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design and synthesis of novel 1,2,3-triazole derivatives of coronopilin as anti-cancer compounds.
AID1155392Cytotoxicity against human A549 cells after 48 hrs by sulforhodamine B assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design and synthesis of novel 1,2,3-triazole derivatives of coronopilin as anti-cancer compounds.
AID310936Cytotoxicity against human KB cells2007Bioorganic & medicinal chemistry, Apr-15, Volume: 15, Issue:8
Quantitative structure-activity relationship of sesquiterpene lactones with cytotoxic activity.
AID608573Toxicity in Swiss albino mouse transplanted with EAC cells assessed as mortality at 50 mg/kg, ip administered for 9 days measured on day 2nd2011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.
AID1155393Cytotoxicity against human MCF7 cells after 48 hrs by sulforhodamine B assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design and synthesis of novel 1,2,3-triazole derivatives of coronopilin as anti-cancer compounds.
AID608572Toxicity in Swiss albino mouse transplanted with EAC cells assessed as mortality at 25 mg/kg, ip administered for 9 days measured on day 4th2011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.
AID608478Toxicity in Swiss albino mouse model of Ehrlich Ascites tumor assessed as mortality at 50 mg/kg, ip administered for 9 days measured on second day2011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.
AID608563Antitumor activity against mouse EAC cells transplanted in ip dosed Swiss albino mouse assessed as tumor growth inhibition administered for 9 days2011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.
AID320961Inhibition of serotonin release in bovine platelets2008Journal of medicinal chemistry, Mar-13, Volume: 51, Issue:5
Neural networks as valuable tools to differentiate between sesquiterpene lactones' inhibitory activity on serotonin release and on NF-kappaB.
AID432383Cytotoxicity against human HeLa cells after 48 hrs by MTT assay2009Bioorganic & medicinal chemistry letters, Aug-01, Volume: 19, Issue:15
Structure-activity relationship (SAR) of parthenin analogues with pro-apoptotic activity: Development of novel anti-cancer leads.
AID608579Antitumor activity against mouse EAC cells transplanted in Swiss albino mouse assessed as tumor growth inhibition at 10 mg/kg, ip administered for 9 days (Rvb = 4.57+/-0.39 mL)2011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.
AID1155390Cytotoxicity against human HCT15 cells after 48 hrs by sulforhodamine B assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design and synthesis of novel 1,2,3-triazole derivatives of coronopilin as anti-cancer compounds.
AID1090869Larvicidal activity against Helicoverpa zea (corn earworm) assessed as growth inhibition at 3 mM/kg relative to control by chronic feeding bioassay2007Journal of agricultural and food chemistry, Dec-12, Volume: 55, Issue:25
Screening of dialkoxybenzenes and disubstituted cyclopentene derivatives against the cabbage looper, Trichoplusia ni, for the discovery of new feeding and oviposition deterrents.
AID1155389Cytotoxicity against human PC3 cells after 48 hrs by sulforhodamine B assay2014European journal of medicinal chemistry, Jul-23, Volume: 82Design and synthesis of novel 1,2,3-triazole derivatives of coronopilin as anti-cancer compounds.
AID608472Antitumor activity against mouse Ehrlich Ascites tumor xenografted in Swiss albino mouse assessed as decrease in tumor weight at 10 mg/kg, ip administered for 9 days (Rvb = 1708+/-51.07 mg)2011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.
AID608477Toxicity in Swiss albino mouse model of Ehrlich Ascites tumor assessed as mortality at 25 mg/kg, ip administered for 9 days measured on fourth day2011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.
AID432385Induction of apoptosis in human HL60 cells assessed as DNA population at sub G0/G1 phase at 10 uM after 6 hrs by flow cytometry2009Bioorganic & medicinal chemistry letters, Aug-01, Volume: 19, Issue:15
Structure-activity relationship (SAR) of parthenin analogues with pro-apoptotic activity: Development of novel anti-cancer leads.
AID608461Cytotoxicity against human DU145 cells assessed as cell growth after 48 hrs by sulforhodamine B assay2011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.
AID608575Antitumor activity against mouse EAC cells transplanted in Swiss albino mouse assessed as decrease in tumor cells in ascetic fluid at 10 mg/kg, ip administered for 9 days (Rvb = 4.57+/-0.39 mL)2011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.
AID432384Cytotoxicity against human HL60 cells after 48 hrs by MTT assay2009Bioorganic & medicinal chemistry letters, Aug-01, Volume: 19, Issue:15
Structure-activity relationship (SAR) of parthenin analogues with pro-apoptotic activity: Development of novel anti-cancer leads.
AID608480Antitumor activity against mouse Ehrlich Ascites tumor xenografted in Swiss albino mouse assessed as tumor growth inhibition at 10 mg/kg, ip administered for 9 days measured on day 132011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.
AID608460Cytotoxicity against human SW620 cells assessed as cell growth after 48 hrs by sulforhodamine B assay2011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.
AID608661Toxicity in ip dosed Swiss albino mouse transplanted with mouse EAC cells assessed as mortality administered for 9 days2011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.
AID612625Antiinflammatory activity in mouse neutrophils assessed as inhibition of LPS-stimulated TNFalpha cytokine expression at 1 ug/ml after 3 hrs by flow cytometeric analysis2011Bioorganic & medicinal chemistry letters, Aug-15, Volume: 21, Issue:16
Psilostachyin, acetylated pseudoguaianolides and their analogues: preparation and evaluation of their anti-inflammatory potential.
AID608462Cytotoxicity against human PC3 cells assessed as cell growth after 48 hrs by sulforhodamine B assay2011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.
AID608565Toxicity in Swiss albino mouse transplanted with mouse EAC cells assessed as mortality at 25 mg/kg, ip administered for 9 days measured on day 2nd2011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.
AID387024Cytotoxicity against human KB cells2008European journal of medicinal chemistry, Oct, Volume: 43, Issue:10
Use of self-organizing maps and molecular descriptors to predict the cytotoxic activity of sesquiterpene lactones.
AID608566Toxicity in Swiss albino mouse transplanted with mouse EAC cells assessed as mortality at 50 mg/kg, ip administered for 9 days measured on day 3rd2011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.
AID336310Antimigraine activity in bovine citreated platelet assessed as inhibition of [14C]serotonin release after 6 mins by scintillation counting1992Journal of natural products, Aug, Volume: 55, Issue:8
A bioassay for inhibition of serotonin release from bovine platelets.
AID608568Antitumor activity against mouse EAC cells transplanted in Swiss albino mouse assessed as decrease in astic fluid volume at 10 mg/kg, ip administered for 9 days (Rvb = 4.57+/-0.39 mL)2011European journal of medicinal chemistry, Aug, Volume: 46, Issue:8
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (42)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (21.43)18.7374
1990's3 (7.14)18.2507
2000's12 (28.57)29.6817
2010's13 (30.95)24.3611
2020's5 (11.90)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 33.55

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 Index33.55 (24.57)
Research Supply Index3.81 (2.92)
Research Growth Index4.93 (4.65)
Search Engine Demand Index44.85 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (33.55)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (6.82%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other41 (93.18%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]