bigelovin profile

bigelovin: a potent cytotoxic sesquiterpene lactone from Inula sp.; structure given in first source; RN refers to (3aR-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9abeta))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

bigelovin : A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetoxy group at position 4. Isolated from Inula hupehensis, it exhibits antineoplastic 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]

Related Flora

Flora	Rank	Flora Definition	Family	Family Definition
Inula	genus	A plant genus of the family ASTERACEAE. Members contain INULIN, alantol, helenin, alantic acid, and acrid resin.[MeSH]	Asteraceae	A 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]
Inula hupehensis	species	[no description available]	Asteraceae	A 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]

ID Source	ID
PubMed CID	3080597
CHEMBL ID	486997
CHEBI ID	69337
MeSH ID	M0261869

Synonym
ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8alpha-dihydroxy-4-oxo-, 12,8-lactone, acetate
3668-14-2
CHEMBL486997
6-o-acetylmexicanin
chebi:69337 ,
bigelovin
[(3as,5r,5ar,8ar,9s,9ar)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] acetate
(3ar,4s,4ar,7ar,8r,9as)-4a,8-dimethyl-3-methylidene-2,5-dioxo-2,3,3a,4,4a,5,7a,8,9,9a-decahydroazuleno[6,5-b]furan-4-yl acetate
6alpha,8alpha-dihydroxy-4-oxo-ambrosa-2,11(13)-dien-12-oic acid-12,8-lactone acetate
3OZJ
DTXSID80190130
CS-0065662
HY-116506
Q27137678
F82266
MS-24395
AKOS040763664

Excerpt	Reference	Relevance
"Bigelovin is a sesquiterpene lactone isolated from the plant Inula helianthus-aquatica which was traditionally used in cancer treatment in Yunnan, China. "	( Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica. Chan, BC; Fung, KP; Ji, CJ; Kwok, HF; Lau, CB; Leung, HW; Leung, PC; Tan, NH; Wong, YL; Yue, GG, 2013)	2.06
"Bigelovin (BigV) is a sesquiterpene lactone, isolated from Inula helianthus aquatica, which has been reported to induce apoptosis and show anti-inflammatory and anti-angiogenic activities. "	( Bigelovin, a sesquiterpene lactone, suppresses tumor growth through inducing apoptosis and autophagy via the inhibition of mTOR pathway regulated by ROS generation in liver cancer. Nie, CH; Wan, DL; Wang, B; Zheng, SS; Zhou, TY, 2018)	3.37

Excerpt	Reference	Relevance
" Within a series of helenalin esters, the acetate (2) and isobutyrate (3) were more toxic than helenalin itself (1)."	( Structure-cytotoxicity relationships of some helenanolide-type sesquiterpene lactones. Beekman, AC; Konings, AW; Pras, N; Schmidt, TJ; van Uden, W; Wikström, HV; Woerdenbag, HJ, 1997)	0.3

Role	Description
apoptosis inducer	Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
immunomodulator	Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
antineoplastic agent	A substance that inhibits or prevents the proliferation of neoplasms.
plant metabolite	Any 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]

Class	Description
acetate ester	Any carboxylic ester where the carboxylic acid component is acetic acid.
organic heterotricyclic compound	An organic tricyclic compound in which at least one of the rings of the tricyclic skeleton contains one or more heteroatoms.
sesquiterpene lactone	Any 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.
cyclic ketone
gamma-lactone	A lactone having a five-membered 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]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Retinoic acid receptor RXR-alpha	Homo sapiens (human)	ED50	4.9000	4.9000	4.9000	4.9000	AID1180602
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
positive regulation of cholesterol efflux	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
negative regulation of transcription by RNA polymerase II	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
positive regulation of thyroid hormone mediated signaling pathway	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
hormone-mediated signaling pathway	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
positive regulation of bone mineralization	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
positive regulation of transporter activity	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
response to retinoic acid	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
peroxisome proliferator activated receptor signaling pathway	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
mRNA transcription by RNA polymerase II	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
steroid hormone mediated signaling pathway	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
positive regulation of DNA-templated transcription	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
positive regulation of transcription by RNA polymerase II	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
retinoic acid receptor signaling pathway	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
positive regulation of vitamin D receptor signaling pathway	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
cell differentiation	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
anatomical structure development	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
vitamin D response element binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
transcription cis-regulatory region binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
RNA polymerase II transcription regulatory region sequence-specific DNA binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specific	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
transcription coregulator binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
retinoic acid binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
double-stranded DNA binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
DNA-binding transcription factor activity	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
nuclear steroid receptor activity	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
nuclear receptor activity	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
protein binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
zinc ion binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
enzyme binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
peptide binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
identical protein binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
nuclear vitamin D receptor binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
sequence-specific DNA binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
retinoic acid-responsive element binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
DNA binding domain binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
LBD domain binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
sequence-specific double-stranded DNA binding	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
nucleus	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
nucleoplasm	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
transcription regulator complex	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
mitochondrion	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
cytosol	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
RNA polymerase II transcription regulator complex	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
chromatin	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
receptor complex	Retinoic acid receptor RXR-alpha	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (37)

Assay ID	Title	Year	Journal	Article
AID725132	Immunomodulatory effect in phytohemagglutininin-activated human PBMC assessed as inhibition of INFgamma production measured after 24 hrs by ELISA	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725138	Inhibition of HMEC1 cells growth measured after 48 hrs by MTT assay	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725129	Immunomodulatory effect in phytohemagglutininin-activated human PBMC assessed as inhibition of INFgamma production at 250 nM measured after 24 hrs by ELISA	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID1180602	Agonist activity at human RXR-alpha expressed in HEK293 cells coexpressing with pCMX-beta-gal after 24 to 48 hrs by luciferase reporter gene assay	2014	Journal of natural products, Jul-25, Volume: 77, Issue:7	Rexinoids isolated from Sophora tonkinensis with a gene expression profile distinct from the synthetic rexinoid bexarotene.
AID725142	Anti-angiogenic activity in transgenic zebrafish Tg(fli1a:EGFP)y1 1 to 4 cell stage embryo assessed as down-regulation of Tie-2 angiogenic gene expression measured after 24 hrs by real-time PCR analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725131	Immunomodulatory effect in phytohemagglutininin-activated human PBMC assessed as inhibition of IL2 production measured after 24 hrs by ELISA	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725123	Effect on cell adhesion gene expression in TNFalpha stimulated HMEC1 cells assessed as reduction in VCAM1 mRNA level at 1000 or 3000 nM measured after 12 hrs by real-time PCR analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725135	Immunomodulatory effect in phytohemagglutininin-activated human PBMC assessed as stimulation of cell proliferation at 62.5 to 250 nM measured after 72 hrs	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725128	Immunomodulatory effect in phytohemagglutininin-activated human PBMC assessed as inhibition of TNFalpha production at 250 nM measured after 24 hrs by ELISA	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID401842	Cytotoxicity against mouse cloned EN2 cells after 2 hrs by MTT assay	1997	Journal of natural products, Mar, Volume: 60, Issue:3	Structure-cytotoxicity relationships of some helenanolide-type sesquiterpene lactones.
AID725141	Anti-angiogenic activity in transgenic zebrafish Tg(fli1a:EGFP)y1 1 to 4 cell stage embryo assessed as down-regulation of Ang-1 angiogenic gene expression measured after 24 hrs by real-time PCR analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725124	Cytotoxicity against human HMEC1 cells	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725146	Anti-angiogenic activity in transgenic zebrafish Tg(fli1a:EGFP)y1 1 to 4 cell stage embryo assessed as inhibition of subintestinal vessels formation measured after 48 hrs by fluorescent microscopy	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725119	Effect on cell adhesion gene expression in TNFalpha stimulated HMEC1 cells assessed as reduction in VCAM1 protern expression at 1000 or 3000 nM measured after 24 hrs by Western blotting	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725139	Inhibition of cell proliferation of HMEC1 cells assessed as [methyl-3H] thymidine incorporation measured after 48 hrs	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725125	Effect on cell adhesion gene expression in TNFalpha stimulated HMEC1 cells assessed as reduction in ICAM1 mRNA level at 1000 or 3000 nM measured after 12 hrs by real-time PCR analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725144	Anti-angiogenic activity in transgenic zebrafish Tg(fli1a:EGFP)y1 1 to 4 cell stage embryo assessed as inhibition of subintestinal vessel length measured at 25 to 100 uM after 48 hrs by fluorescent microscopy	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725127	Immunomodulatory effect in phytohemagglutininin-activated human PBMC assessed as inhibition of IL2 production at 250 nM measured after 24 hrs by ELISA	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID626782	Antiinflammatory action in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide production treated 30 mins before LPS challenge measured after 24 hrs by griess reaction	2011	Journal of natural products, Sep-23, Volume: 74, Issue:9	Pseudoguaianolides and guaianolides from Inula hupehensis as potential anti-inflammatory agents.
AID771667	Cytotoxicity against human MDA-MB-231 cells assessed as growth inhibition after 72 hrs by MTT assay	2013	European journal of medicinal chemistry, Oct, Volume: 68	Selective cytotoxicity, inhibition of cell cycle progression, and induction of apoptosis in human breast cancer cells by sesquiterpenoids from Inula lineariifolia Turcz.
AID725130	Immunomodulatory effect in phytohemagglutininin-activated human PBMC assessed as inhibition of IL12 production measured after 24 hrs by ELISA	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725121	Cytotoxicity against human HMEC1 cells at 1000 or 3000 nM measured after 12 hrs by MTT assay	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725126	Inhibition of adhesion of THP1 cells to TNFalpha stimulated HMEC1 cells measured after 5 hrs	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725140	Anti-angiogenic activity in transgenic zebrafish Tg(fli1a:EGFP)y1 1 to 4 cell stage embryo assessed as down-regulation of Tie-1 angiogenic gene expression measured after 24 hrs by real-time PCR analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725145	Anti-angiogenic activity in transgenic zebrafish Tg(fli1a:EGFP)y1 1 to 4 cell stage embryo assessed as complete inhibition of subintestinal vessels formation measured at 100 uM after 48 hrs by fluorescent microscopy	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725143	Anti-angiogenic activity in transgenic zebrafish Tg(fli1a:EGFP)y1 1 to 4 cell stage embryo assessed as down-regulation of Ang-2 angiogenic gene expression measured after 24 hrs by real-time PCR analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID771666	Cytotoxicity against human MCF10A cells assessed as growth inhibition after 72 hrs by MTT assay	2013	European journal of medicinal chemistry, Oct, Volume: 68	Selective cytotoxicity, inhibition of cell cycle progression, and induction of apoptosis in human breast cancer cells by sesquiterpenoids from Inula lineariifolia Turcz.
AID725137	Inhibition of HMEC1 cells growth measured after 48 hrs	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725120	Effect on cell adhesion gene expression in TNFalpha stimulated HMEC1 cells assessed as reduction in E-selectin protern expression at 1000 or 3000 nM measured after 24 hrs by Western blotting	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725122	Effect on cell adhesion gene expression in TNFalpha stimulated HMEC1 cells assessed as reduction in E-selectin mRNA level at 1000 or 3000 nM measured after 12 hrs by real-time PCR analysis	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725134	Immunomodulatory effect in phytohemagglutininin-activated human PBMC assessed as inhibition of TNFalpha production measured after 24 hrs by ELISA	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725136	Antimigratory activity against HMEC1 cells assessed as decrease in cell motility measured after 24 hrs by scratch wound assay	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID725133	Cytotoxicity against human PBMC at 62.5 to 250 nM for 72 hrs by XTT assay	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID401843	Cytotoxicity against mouse cloned EN2 cells after 72 hrs by MTT assay	1997	Journal of natural products, Mar, Volume: 60, Issue:3	Structure-cytotoxicity relationships of some helenanolide-type sesquiterpene lactones.
AID771668	Cytotoxicity against human MCF7 cells assessed as growth inhibition after 72 hrs by MTT assay	2013	European journal of medicinal chemistry, Oct, Volume: 68	Selective cytotoxicity, inhibition of cell cycle progression, and induction of apoptosis in human breast cancer cells by sesquiterpenoids from Inula lineariifolia Turcz.
AID725118	Effect on cell adhesion gene expression in TNFalpha stimulated HMEC1 cells assessed as reduction in ICAM1 protern expression at 1000 or 3000 nM measured after 24 hrs by Western blotting	2013	European journal of medicinal chemistry, Jan, Volume: 59	Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica.
AID626783	Cytotoxicity against mouse RAW264.7 cells after 24 hrs by MTT assay	2011	Journal of natural products, Sep-23, Volume: 74, Issue:9	Pseudoguaianolides and guaianolides from Inula hupehensis as potential anti-inflammatory agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	2 (11.76)	18.2507
2000's	2 (11.76)	29.6817
2010's	11 (64.71)	24.3611
2020's	2 (11.76)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	17 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
pimagedine pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.	2.06	1	guanidines; one-carbon compound	EC 1.14.13.39 (nitric oxide synthase) inhibitor; EC 1.4.3.4 (monoamine oxidase) inhibitor
helenalin helenalin: toxic principle of Helenium microcephalum (smallhead sneezeweed); structure. helenalin : A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer).. NF-kappaB inhibitor : An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.	1.99	1	cyclic ketone; gamma-lactone; organic heterotricyclic compound; secondary alcohol; sesquiterpene lactone	anti-inflammatory agent; antineoplastic agent; metabolite; plant metabolite
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	2.08	1	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
honokiol [no description available]	2.1	1	biphenyls
bexarotene [no description available]	2.1	1	benzoic acids; naphthalenes; retinoid	antineoplastic agent
Mexicanin I [no description available]	1.99	1	sesquiterpene lactone
tomentosin tomentosin: isolated from fresh Inula viscosa (Asteraceae) flowers; structure in first source	2.06	1	sesquiterpene lactone
confertin confertin: structure. confertin : A pseudoguaianolide that is decahydroazuleno[6,5-b]furan-2(3H)-one substituted by an oxo group at position 5, methyl groups at positions 4a and 8 and a methylidene group at position 3. It has been isolated from the aerial parts of Inula hupehensis.	2.06	1	cyclic ketone; gamma-lactone; organic heterotricyclic compound; pseudoguaianolide	anti-inflammatory agent; metabolite; plant metabolite
inuviscolide inuviscolide: from Inula viscosa; structure in first source. inuviscolide : A sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2(3H)-one substituted by a hydroxy group at position 5, a methyl group at position 5 and methylidene groups at positions 3 and 8 (the 3aR,4aR,5R,7aS,9aS stereoisomer). Isolated from the aerial parts of Inula hupehensis, it exhibits anti-inflammatory activity.	2.06	1	gamma-lactone; organic heterotricyclic compound; sesquiterpene lactone; tertiary alcohol	anti-inflammatory agent; plant metabolite
ergolide ergolide: a potent cytotoxic sesquiterpene lactone from Inula sp.; structure given in first source. ergolide : A sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetyloxy group at position 4. It has been isolated from the aerial parts of Inula hupehensis.	7.72	3	acetate ester; cyclic ketone; gamma-lactone; organic heterotricyclic compound; sesquiterpene lactone	anti-inflammatory agent; antineoplastic agent; metabolite; NF-kappaB inhibitor; plant metabolite
aromaticin [no description available]	2.06	1	cyclic ketone; gamma-lactone; organic heterotricyclic compound; sesquiterpene lactone	anti-inflammatory agent; metabolite; plant metabolite
sophoranone sophoranone: a flavonoid compound with isoprenoid side chains; extracted from a traditional Chinese medicine Shan Dou Gen, isolated from the roots of Sophora subprostrata; structure in first source. sophoranone : A dihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 7 and 4' and prenyl groups at positions 3' and 5' respectively.	2.1	1	4'-hydroxyflavanones; dihydroxyflavanone	plant metabolite
angustibalin angustibalin: sesquiterpene lactone from Balduina angustifolia (Pursh) Robins; structure	1.99	1	sesquiterpene lactone
11alpha,13-dihydrohelenalin [no description available]	1.99	1	sesquiterpene lactone
docosahexaenoate efalex: a mixture of fish oil and primrose oil; used as a high-docosahexaenoic acid fatty acid supplement. docosahexaenoic acid : Any C22 polyunsaturated fatty acid containing six double bonds.. docosahexaenoate : A polyunsaturated fatty acid anion that is the conjugate base of docosahexaenoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.. all-cis-docosa-4,7,10,13,16,19-hexaenoic acid : A docosahexaenoic acid having six cis-double bonds at positions 4, 7, 10, 13, 16 and 19.	2.1	1	docosahexaenoic acid; omega-3 fatty acid	algal metabolite; antineoplastic agent; Daphnia tenebrosa metabolite; human metabolite; mouse metabolite; nutraceutical
sesquiterpenes [no description available]	3.95	12
chamissonolide chamissonolide: structure given in first source	1.99	1

Condition	Relationship Strength	Studies
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	1.99	1
Breast Cancer [description not available]	2.08	1
Breast Neoplasms Tumors or cancer of the human BREAST.	2.08	1
Hepatocellular Carcinoma [description not available]	7.6	1
Cancer of Liver [description not available]	2.69	2
Cancer of Lung [description not available]	2.6	1
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.6	1
Liver Neoplasms Tumors or cancer of the LIVER.	2.69	2
Lung Neoplasms Tumors or cancer of the LUNG.	2.6	1
Cancer of Colon [description not available]	2.31	1
Colonic Neoplasms Tumors or cancer of the COLON.	2.31	1
Colorectal Cancer [description not available]	2.57	2
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	2.57	2
Kahler Disease [description not available]	2.08	1
Multiple Myeloma A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.	7.08	1
Benign Neoplasms [description not available]	2.11	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	2.11	1

bigelovin

Description

Cross-References

Synonyms (17)

Research Excerpts

Overview

Toxicity

Roles (4)

Drug Classes (5)

Protein Targets (1)

Other Measurements

Biological Processes (16)

Molecular Functions (22)

Ceullar Components (8)

Bioassays (37)

Research

Studies (17)

Market Indicators

Research Demand Index: 12.41

Study Types

bigelovin

Description

Related Flora

Cross-References

Synonyms (17)

Research Excerpts

Overview

Toxicity

Roles (4)

Drug Classes (5)

Protein Targets (1)

Other Measurements

Biological Processes (16)

Molecular Functions (22)

Ceullar Components (8)

Bioassays (37)

Research

Studies (17)

Market Indicators

Research Demand Index: 12.41

Study Types

Related Drugs (17)

Related Conditions (17)