Page last updated: 2024-12-10

petasin

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

Description

petasin: both petasin and neopetasin inhibit biosynthesis of cysteinyl-leukotriene; unlike petasin, neopetasin does not inhibit eosinophil cation protein releasenor suppresses cPLA2 activity; from Petasites formosanus Kitamurai; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

petasin : An enoate ester obtained by formal condensation of the carboxy group of angelic acid with the hydroxy group of (1R,2R,7S,8aR)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-ol. [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
PetasitesgenusA plant genus of the family ASTERACEAE. Members contain SESQUITERPENES. The common name of sweet coltsfoot is similar to the common name for TUSSILAGO.[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]
Petasites formosanusspecies[no description available]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 CID5281526
CHEMBL ID3291073
CHEBI ID8030
SCHEMBL ID12621121
MeSH IDM0377075

Synonyms (24)

Synonym
(+)-petasin
9z0q32j0qc ,
2-butanoic acid, 2-methyl-, 1,2,3,4,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-6-oxo-2-naphthalenyl ester, (1r-(1alpha,2beta(z),7beta,8aalpha))-
unii-9z0q32j0qc
26577-85-5
petasin
C09706 ,
AC1NQYL4 ,
[(1r,2r,7s,8ar)-1,8a-dimethyl-6-oxo-7-prop-1-en-2-yl-1,2,3,4,7,8-hexahydronaphthalen-2-yl] (z)-2-methylbut-2-enoate
o-angeloylsencathenone
petasine
petaforce
crotonic acid, 2-methyl-, ester with 3.alpha.-hydroxy-eremophila-9,11-dien-8-one, (z)-
2-butenoic acid, 2-methyl-, (1r,2r,7s,8ar)-1,2,3,4,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-6-oxo-2-naphthalenyl ester, (2z)-
CHEMBL3291073
CHEBI:8030 ,
(1r,2r,7s,8ar)-1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl (2z)-2-methylbut-2-enoate
SCHEMBL12621121
surecn12621121
zinc05132525
[(1r,2r,7s,8ar)-7-isopropenyl-1,8a-dimethyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalen-2-yl] (z)-2-methylbut-2-enoate
Q7171781
XP173205
DTXSID201030056

Research Excerpts

Overview

S-petasin is a bioactive compound isolated from leaves or roots of Petasites hybridus.

ExcerptReferenceRelevance
"S-petasin is a bioactive compound isolated from leaves or roots of Petasites hybridus."( Effects of S-petasin on corticosterone release in rats.
Chang, LL; Lin, YL; Tseng, YC; Wang, PS; Wun, WS, 2002
)
1.24
"S-petasin is a bioactive compound isolated from leaves or roots of P."( Effects of S-petasin on cyclic AMP production and enzyme activity of P450scc in rat zona fasciculata-reticularis cells.
Chang, LL; Lin, YL; Wang, PS; Wun, WS, 2004
)
1.25

Effects

S-Petasin has been used to relieve gastrointestinal pain, lung disease, and spasms of the urogenital tract.

ExcerptReferenceRelevance
"S-Petasin has been isolated from Petasites hybridus (L.), Petasites officinalis (L.) and Petasites formosanus, but not from Petasites japonicus."( S-Petasin isolated from Petasites japonicus exerts anti-adipogenic activity in the 3T3-L1 cell line by inhibiting PPAR-γ pathway signaling.
Choi, YW; Cui, ZW; Guo, L; Kang, JS; Li, K; Son, BG, 2019
)
1.79
"S-petasin has been used to relieve gastrointestinal pain, lung disease, and spasms of the urogenital tract."( Effects of S-petasin on corticosterone release in rats.
Chang, LL; Lin, YL; Tseng, YC; Wang, PS; Wun, WS, 2002
)
1.24

Actions

ExcerptReferenceRelevance
"S-Petasin could inhibit I(Ca,L) evoked by action potential waveforms effectively."( The mechanism of inhibitory actions of S-petasin, a sesquiterpene of Petasites formosanus, on L-type calcium current in NG108-15 neuronal cells.
Chen, H; Lin, YL; Wu, SN, 2003
)
1.14
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
vasodilator agentA drug used to cause dilation of the blood vessels.
anti-allergic agentA drug used to treat allergic reactions.
EC 2.7.11.31 {[hydroxymethylglutaryl-CoA reductase (NADPH)] kinase} activatorAny compound that binds to and activates the enzyme [hydroxymethylglutaryl-CoA reductase (NADPH)] kinase (EC 2.7.11.31).
[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 (4)

ClassDescription
sesquiterpenoidAny terpenoid derived from a sesquiterpene. The term includes compounds in which the C15 skeleton of the parent sesquiterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
enoneAn alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position.
alicyclic ketoneA cyclic ketone in which the carbocyclic ring structure which may be saturated or unsaturated, but may not be a benzenoid or other aromatic system.
enoate esterAn alpha,beta-unsaturated carboxylic ester of general formula R(1)R(2)C=CR(3)-C(=O)OR(4) (R(4) =/= H) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.
[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 (38)

Assay IDTitleYearJournalArticle
AID1387101Antiproliferative activity against human MV411 cells after 72 hrs by MTT assay
AID1154420Activation of AMPK in glucose loaded C57BL/6J mouse assessed as decrease of AUC of blood glucose level at 100 to 200 mg/kg, po after 1 hr by oral glucose tolerance test2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154410Increase of AMPKalpha phosphorylation at Thr172 in mouse 3T3L1 cells at 10 uM after 2 hrs by Western blot analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154415Activation of AMPK in C57BL/6J mouse white adipose tissue assessed as phosphorylated ACC level at 200 mg/kg, po after 2 hrs by Western blot analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1387100Antiproliferative activity against human HeLa cells after 72 hrs by MTT assay
AID1154417Activation of AMPK in C57BL/6J mouse skeletal muscle assessed as phosphorylated ACC level at 200 mg/kg, po after 2 hrs by Western blot analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154419Activation of AMPK in C57BL/6J mouse skeletal muscle assessed as increase of PGC-1alpha transcription at 100 to 200 mg/kg, sc after 2 hrs by Western blot analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154425Activation of AMPK in rat H4IIE cells assessed as increase of ADP level by spectrophotometric analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154435Activation of AMPK in mouse 3T3L1 cells assessed as increase of ADP/ATP ratio level after 2 hrs by spectrophotometric analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154434Activation of AMPK in rat H4IIE cells assessed as increase of ADP/ATP ratio level after 1 hr by spectrophotometric analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154407Increase of AMPKalpha phosphorylation at Thr172 in rat H4IIE cells after 1 hr by Western blot analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154409Increase of AMPKalpha phosphorylation at Thr172 in rat H4IIE cells at 0.3 uM after 2 hrs by Western blot analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154428Activation of AMPK in rat H4IIE cells assessed as decrease of ATP level by spectrophotometric analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154414Activation of AMPK in C57BL/6J mouse white adipose tissue at 200 mg/kg, po after 2 hrs by Western blot analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154413Activation of AMPK in C57BL/6J mouse liver assessed as phosphorylated ACC level at 200 mg/kg, po after 2 hrs by Western blot analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154427Activation of AMPK in mouse C2C12 cells assessed as increase of ADP level by spectrophotometric analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154431Activation of AMPK in rat H4IIE cells assessed as increase of AMP/ATP ratio level after 1 hr by spectrophotometric analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154424Activation of AMPK in mouse C2C12 cells assessed as increase of AMP level by spectrophotometric analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154421Activation of AMPK in glucose loaded C57BL/6J mouse assessed as decrease of AUC of blood glucose level at 500 mg/kg, po after 1 hr by oral glucose tolerance test2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154430Activation of AMPK in mouse C2C12 cells assessed as decrease of ATP level by spectrophotometric analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154439Inhibition of rat liver mitochondrial respiratory chain complex 2 assessed as reduction of oxygen consumption at stage 4 in presence of succinate and rotenone2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154416Activation of AMPK in C57BL/6J mouse skeletal muscle at 200 mg/kg, po after 2 hrs by Western blot analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154422Activation of AMPK in rat H4IIE cells assessed as increase of AMP level by spectrophotometric analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154433Activation of AMPK in mouse C2C12 cells assessed as increase of AMP/ATP ratio level after 2 hrs by spectrophotometric analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154423Activation of AMPK in mouse 3T3L1 cells assessed as increase of AMP level by spectrophotometric analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1387098Antiproliferative activity against human A549 cells after 72 hrs by MTT assay
AID1387099Antiproliferative activity against human HGC27 cells after 72 hrs by MTT assay
AID1154411Increase of AMPKalpha phosphorylation at Thr172 in mouse C2C12 cells at 5 uM after 2 hrs by Western blot analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154426Activation of AMPK in mouse 3T3L1 cells assessed as increase of ADP level by spectrophotometric analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154412Activation of AMPK in C57BL/6J mouse liver at 200 mg/kg, po after 2 hrs by Western blot analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154408Activation of AMPKalpha in rat H4IIE cells assessed as ACC phosphorylation at Ser79 after 1 hr by Western blot analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154429Activation of AMPK in mouse 3T3L1 cells assessed as decrease of ATP level by spectrophotometric analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154438Inhibition of rat liver mitochondrial respiratory chain complex 1 assessed as reduction of oxygen consumption at stage 4 in presence of glutamate and malate2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154432Activation of AMPK in mouse 3T3L1 cells assessed as increase of AMP/ATP ratio level after 2 hrs by spectrophotometric analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154436Activation of AMPK in mouse C2C12 cells assessed as increase of ADP/ATP ratio level after 2 hrs by spectrophotometric analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154437Inhibition of rat liver mitochondrial respiratory chain complex 1 assessed as reduction of oxygen consumption at stage 4 at 10 uM in presence of glutamate and ADP2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154440Activation of AMPK in LKB1-deficient human HeLa cells at 10 to 100 uM after 1 hr by Western blot analysis2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
AID1154406Increase of AMPK phosphorylation at Thr172 in rat H4IIE cells at 5 to 10 uM after 1 hr by ELISA2014Journal of natural products, Jun-27, Volume: 77, Issue:6
Petasin activates AMP-activated protein kinase and modulates glucose metabolism.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (39)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (2.56)18.7374
1990's0 (0.00)18.2507
2000's19 (48.72)29.6817
2010's11 (28.21)24.3611
2020's8 (20.51)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.49

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 Index34.49 (24.57)
Research Supply Index3.76 (2.92)
Research Growth Index5.47 (4.65)
Search Engine Demand Index49.68 (26.88)
Search Engine Supply Index2.38 (0.95)

This Compound (34.49)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (7.69%)5.53%
Reviews2 (5.13%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other34 (87.18%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]