Page last updated: 2024-12-07

spathulenol

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

Description

Spathulenol is a sesquiterpene alcohol with a bicyclic structure. It is found in a variety of plants, including ferns, mosses, and liverworts. Spathulenol has been shown to possess a range of biological activities, including antifungal, antibacterial, and anti-inflammatory properties. It has also been found to be a potent inhibitor of the enzyme cyclooxygenase-2 (COX-2), which is involved in the production of prostaglandins, inflammatory mediators that contribute to pain and inflammation. The compound's interesting biological activities have led to ongoing research into its potential therapeutic applications. The biosynthesis of spathulenol is thought to involve a series of enzymatic steps that begin with the conversion of farnesyl pyrophosphate (FPP) to the sesquiterpene precursor, spathulenol. Further research is ongoing to elucidate the specific enzymes involved in its synthesis and to investigate its potential therapeutic applications.'

spathulenol: sesquiterpene alcohol isolated from essential oils of Artemisia vulgaris L. & Artemisia dracunculus L. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

spathulenol : A tricyclic sesquiterpenoid that is 4-methylidenedecahydro-1H-cyclopropa[e]azulene carrying three methyl substituents at positions 1, 1 and 7 as well as a hydroxy substituent at position 7. [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
Dracunculusgenus[no description available]AraceaeA plant family of the order ALISMATALES. Many members contain OXALIC ACID and calcium oxalate (OXALATES).[MeSH]
ArtemisiagenusA plant genus of the family ASTERACEAE with strong-smelling foliage. It is a source of SANTONIN and other cytotoxic TERPENES.[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]
Artemisia dracunculusspecies[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]
Artemisia dracunculusspecies[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]
Artemisia vulgarisspeciesThe common name of wormwood or mugwort may refer to other species of ARTEMISIA. Source of allergen Ag7.[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]
Artemisia vulgarisspeciesThe common name of wormwood or mugwort may refer to other species of ARTEMISIA. Source of allergen Ag7.[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]
Artemisia vulgarisspeciesThe common name of wormwood or mugwort may refer to other species of ARTEMISIA. Source of allergen Ag7.[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]
Dracunculusgenus[no description available]AraceaeA plant family of the order ALISMATALES. Many members contain OXALIC ACID and calcium oxalate (OXALATES).[MeSH]
ArtemisiagenusA plant genus of the family ASTERACEAE with strong-smelling foliage. It is a source of SANTONIN and other cytotoxic TERPENES.[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]
Artemisia dracunculusspecies[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]
Artemisia dracunculusspecies[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]
Artemisia vulgarisspeciesThe common name of wormwood or mugwort may refer to other species of ARTEMISIA. Source of allergen Ag7.[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]
Artemisia vulgarisspeciesThe common name of wormwood or mugwort may refer to other species of ARTEMISIA. Source of allergen Ag7.[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]
Artemisia vulgarisspeciesThe common name of wormwood or mugwort may refer to other species of ARTEMISIA. Source of allergen Ag7.[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 CID522266
SCHEMBL ID3847321
MeSH IDM0060865
PubMed CID92231
CHEMBL ID518542
CHEBI ID132824
SCHEMBL ID309962
MeSH IDM0060865

Synonyms (35)

Synonym
spathulenol
6750-60-3
1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-ol
(1ar,4ar,7s,7ar,7br)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-ol
(7s)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-ol
beta-spathulenol
SCHEMBL3847321
FRMCCTDTYSRUBE-UHFFFAOYSA-N
1,7,7-trimethyl-4-methylidene-decahydro-1h-cyclopropa[e]azulen-1-ol
decahydro-1,1,7-trimethyl-4-methylene-1h-cycloprop[e]azulen-7-ol
AKOS032948354
1h-cycloprop[e]azulen-7-ol, decahydro-1,1,7-trimethyl-4-methylene-, [1ar-(1aalpha,4aalpha,7beta,7abeta,7balpha)]-
1,1,7-trimethyl-4-methylidenedecahydro-1h-cyclopropa[e]azulen-7-ol
DTXSID40863939
CHEBI:132824 ,
(1ar,4ar,7s,7ar,7br)-1,1,7-trimethyl-4-methylidenedecahydro-1h-cyclopropa[e]azulen-7-ol
CHEMBL518542
spatulenol
(+)-spathulenol
espatulenol
unii-7xv9l96sjj
7xv9l96sjj ,
1h-cycloprop(e)azulen-7-ol, decahydro-1,1,7-trimethyl-4-methylene-, (1ar-(1aalpha,4aalpha,7beta,7abeta,7balpha))-
1h-cycloprop(e)azulen-7-ol, decahydro-1,1,7-trimethyl-4-methylene-
1h-cycloprop(e)azulen-7-ol, decahydro-1,1,7-trimethyl-4-methylene-, (1ar,4ar,7s,7ar,7br)-
SCHEMBL309962
spathulenol?
AKOS037515399
HY-N1205
Q1376658
spathulenol,(+)-spathulenol,espatulenol
CS-0016592
F82083
MS-23227
(1ar,4ar,7s,7ar,7br)-1,1,7-trimethyl-4-methylidenedecahydro-1h-cyclopropa(e)azulen-7-ol

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Finally, a dose-response correlation was observed between Waldhemia glabra essential oil concentration and viability of human breast adenocarcinoma cells MDA-MB-231 and MCF-7."( Screening of the chemical composition and bioactivity of Waldheimia glabra (Decne.) Regel essential oil.
Catalano, E; Dallavalle, S; Giorgi, A; Iriti, M; Manzo, A; Musso, L; Panseri, S; Scarì, G, 2016
)
0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
volatile oil componentAny plant metabolite that is found naturally as a component of a volatile oil.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
anaestheticSubstance which produces loss of feeling or sensation.
vasodilator agentA drug used to cause dilation of the blood vessels.
[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).
carbotricyclic compoundA carbopolyclic compound comprising of three carbocyclic rings.
tertiary alcoholA tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it.
olefinic compoundAny organic molecular entity that contains at least one C=C bond.
[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 (29)

Assay IDTitleYearJournalArticle
AID335041Cytotoxicity against human ZR-75-1 cells1992Journal of natural products, May, Volume: 55, Issue:5
Plant anticancer agents, L. cytotoxic triterpenes from Sandoricum koetjape stems.
AID332532Cytotoxicity against human SK-MEL-2 cells1994Journal of natural products, Jun, Volume: 57, Issue:6
Cytotoxic constituents of Baccharis gaudichaudiana.
AID332530Cytotoxicity against human KBV1 cells1994Journal of natural products, Jun, Volume: 57, Issue:6
Cytotoxic constituents of Baccharis gaudichaudiana.
AID335037Cytotoxicity against human vinblastine-resistant KBV1 cells1992Journal of natural products, May, Volume: 55, Issue:5
Plant anticancer agents, L. cytotoxic triterpenes from Sandoricum koetjape stems.
AID1484072Cytotoxicity against African green monkey Vero cells assessed as decrease in cell viability at 90 uM after 2 days by MTT assay2017Journal of natural products, 02-24, Volume: 80, Issue:2
Sesquiterpenoids with Various Carbocyclic Skeletons from the Flowers of Chrysanthemum indicum.
AID335040Cytotoxicity against human SK-MEL-2 cells1992Journal of natural products, May, Volume: 55, Issue:5
Plant anticancer agents, L. cytotoxic triterpenes from Sandoricum koetjape stems.
AID1484076Antiviral activity against Porcine epidemic diarrhea virus infected in African green monkey Vero cells assessed as inhibition of virus-induced cytopathic effect at 50 uM after 3 days2017Journal of natural products, 02-24, Volume: 80, Issue:2
Sesquiterpenoids with Various Carbocyclic Skeletons from the Flowers of Chrysanthemum indicum.
AID332526Cytotoxicity against human BC1 cells1994Journal of natural products, Jun, Volume: 57, Issue:6
Cytotoxic constituents of Baccharis gaudichaudiana.
AID335043Antimitotic activity in rat ASK cells at 0.32 to 20 ug/mL1992Journal of natural products, May, Volume: 55, Issue:5
Plant anticancer agents, L. cytotoxic triterpenes from Sandoricum koetjape stems.
AID1070523Partition coefficient, log K of the compound in n-hexane/methyl tert-butylether/acetonitrile 10:1:10 solvent system by HSCCC/EECCC analysis2014Journal of natural products, Mar-28, Volume: 77, Issue:3
Airborne antituberculosis activity of Eucalyptus citriodora essential oil.
AID402548Antiinflammatory activity against mouse assessed as inhibition TPA-induced ear edema at 0.5 mg/kg2004Journal of natural products, May, Volume: 67, Issue:5
Three new sesquiterpenes from Croton arboreous.
AID335034Cytotoxicity against human Col2 cells1992Journal of natural products, May, Volume: 55, Issue:5
Plant anticancer agents, L. cytotoxic triterpenes from Sandoricum koetjape stems.
AID335033Cytotoxicity against human BC1 cells1992Journal of natural products, May, Volume: 55, Issue:5
Plant anticancer agents, L. cytotoxic triterpenes from Sandoricum koetjape stems.
AID332529Cytotoxicity against human KB cells1994Journal of natural products, Jun, Volume: 57, Issue:6
Cytotoxic constituents of Baccharis gaudichaudiana.
AID335038Cytotoxicity against human LNCAP cells1992Journal of natural products, May, Volume: 55, Issue:5
Plant anticancer agents, L. cytotoxic triterpenes from Sandoricum koetjape stems.
AID332533Cytotoxicity against mouse P388 cells1994Journal of natural products, Jun, Volume: 57, Issue:6
Cytotoxic constituents of Baccharis gaudichaudiana.
AID671764Inhibition of HCV NS3 helicase ATP hydrolysis activity overexpressed in Escherichia coli BL21(DE3) assessed as inhibition of inorganic phosphate release by AM/MG-based colometric analysis in the presence of M13 ssDNA2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Identification of myricetin and scutellarein as novel chemical inhibitors of the SARS coronavirus helicase, nsP13.
AID671761Inhibition of SARS coronavirus nsP13 helicase activity expressed in Escherichia coli Rosetta assessed inhibition of DNA unwinding activity at 10 uM by FRET assay2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Identification of myricetin and scutellarein as novel chemical inhibitors of the SARS coronavirus helicase, nsP13.
AID671762Inhibition of HCV NS3 helicase overexpressed in Escherichia coli BL21(DE3) assessed as inhibition of DNA unwinding activity at 10 uM by FRET assay2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Identification of myricetin and scutellarein as novel chemical inhibitors of the SARS coronavirus helicase, nsP13.
AID332531Cytotoxicity against human Lu1 cells1994Journal of natural products, Jun, Volume: 57, Issue:6
Cytotoxic constituents of Baccharis gaudichaudiana.
AID335036Cytotoxicity against human KB cells1992Journal of natural products, May, Volume: 55, Issue:5
Plant anticancer agents, L. cytotoxic triterpenes from Sandoricum koetjape stems.
AID335042Cytotoxicity against mouse P388 cells1992Journal of natural products, May, Volume: 55, Issue:5
Plant anticancer agents, L. cytotoxic triterpenes from Sandoricum koetjape stems.
AID1256913Inhibition of human IDH1 expressed in IPTG-induced Escherichia coli BL21 cells assessed as reduction of NADP+ to NADPH after 5 mins by spectrophotometry2015Bioorganic & medicinal chemistry letters, Dec-01, Volume: 25, Issue:23
Discovery of α-mangostin as a novel competitive inhibitor against mutant isocitrate dehydrogenase-1.
AID335032Cytotoxicity against human A431 cells1992Journal of natural products, May, Volume: 55, Issue:5
Plant anticancer agents, L. cytotoxic triterpenes from Sandoricum koetjape stems.
AID332528Cytotoxicity against human HT1080 cells1994Journal of natural products, Jun, Volume: 57, Issue:6
Cytotoxic constituents of Baccharis gaudichaudiana.
AID335035Cytotoxicity against human HT1080 cells1992Journal of natural products, May, Volume: 55, Issue:5
Plant anticancer agents, L. cytotoxic triterpenes from Sandoricum koetjape stems.
AID332527Cytotoxicity against human Col2 cells1994Journal of natural products, Jun, Volume: 57, Issue:6
Cytotoxic constituents of Baccharis gaudichaudiana.
AID1256912Inhibition of human IDH1 R132H mutant expressed in IPTG-induced Escherichia coli BL21 cells assessed as oxidation of NADPH to NADP+ after 5 mins by spectrophotometry2015Bioorganic & medicinal chemistry letters, Dec-01, Volume: 25, Issue:23
Discovery of α-mangostin as a novel competitive inhibitor against mutant isocitrate dehydrogenase-1.
AID335039Cytotoxicity against human Lu1 cells1992Journal of natural products, May, Volume: 55, Issue:5
Plant anticancer agents, L. cytotoxic triterpenes from Sandoricum koetjape stems.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (67)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (4.48)18.2507
2000's6 (8.96)29.6817
2010's49 (73.13)24.3611
2020's9 (13.43)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 36.73

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index36.73 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index5.03 (4.65)
Search Engine Demand Index47.56 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (36.73)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews1 (1.64%)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%
Other60 (98.36%)84.16%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]