Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H36O2 |
| Molecular Weight | 308.4986 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@@](C)(O)[C@H](CC[C@@](C)(O)C=C)[C@@]1(C)CCCC2(C)C
InChI
InChIKey=XVULBTBTFGYVRC-HHUCQEJWSA-N
InChI=1S/C20H36O2/c1-7-18(4,21)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)22/h7,15-16,21-22H,1,8-14H2,2-6H3/t15-,16+,18-,19-,20+/m0/s1
| Molecular Formula | C20H36O2 |
| Molecular Weight | 308.4986 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22250858
https://www.ncbi.nlm.nih.gov/pubmed/27466023
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22250858
https://www.ncbi.nlm.nih.gov/pubmed/27466023
Sclareol isolated from Salvia officinalis is widely used as a fragrance material. Sclareol is known to exert various biological activities. Sclareol possesses high lipophilicity, that precluded the evaluation of its anticancer effect in vivo. To overcome high toxicity and high lipophilicity of clareol, it was incorporated in liposomes. It demonstrated significant cytotoxic activity against human leukemic cell lines, but no cytotoxicity towards normal cells at concentration as high as 100 uM. Thus, sclareol possesses chemotherapeutic potential for the treatment of colorectal and other types of human cancer. Also was found, that sclareol-containing cream improved wrinkles in a clinical trial. It alleviates facial wrinkle formation via an antiphotoaging mechanism and may be an effective candidate ingredient. The anti-inflammatory mechanisms of sclareol might be related to a decrease of inflammatory cytokines and an increase of antioxidant enzyme activity.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Diterpenes from the berries of Juniperus excelsa. | 1999 Apr |
|
| Chromatographic (GC-MS, HPLC) and virological evaluations of Salvia sclarea infected by BBWV-I. | 2001 Mar |
|
| A plant plasma membrane ATP binding cassette-type transporter is involved in antifungal terpenoid secretion. | 2001 May |
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| Antimycobacterial plant terpenoids. | 2001 Nov |
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| The ABC transporter SpTUR2 confers resistance to the antifungal diterpene sclareol. | 2002 Jun |
|
| The plant PDR family of ABC transporters. | 2002 Nov |
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| Antibacterial diterpenoids from Astragalus brachystachys. | 2002 Nov-Dec |
|
| Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit. | 2002 Oct |
|
| Identification of regulatory sequence elements within the transcription promoter region of NpABC1, a gene encoding a plant ABC transporter induced by diterpenes. | 2003 Jul |
|
| Pathogen-responsive expression of a putative ATP-binding cassette transporter gene conferring resistance to the diterpenoid sclareol is regulated by multiple defense signaling pathways in Arabidopsis. | 2003 Nov |
|
| Effect of 13-epi-sclareol on the bacterial respiratory chain. | 2004 Nov |
|
| First enantiospecific synthesis of the antitumor marine sponge metabolite (-)-15-oxopuupehenol from (-)-sclareol. | 2005 Apr 14 |
|
| Microbial hydroxylation of sclareol by Rhizopus stolonifer. | 2005 Aug 31 |
|
| A comparative study of the effects of cholesterol and sclareol, a bioactive labdane type diterpene, on phospholipid bilayers. | 2005 Feb |
|
| NpPDR1, a pleiotropic drug resistance-type ATP-binding cassette transporter from Nicotiana plumbaginifolia, plays a major role in plant pathogen defense. | 2005 Sep |
|
| Labd-14-ene-8,13-diol (sclareol) induces cell cycle arrest and apoptosis in human breast cancer cells and enhances the activity of anticancer drugs. | 2006 Apr |
|
| Hemisynthesis of new labdane derivatives from (-)-sclareol. | 2006 Aug |
|
| Structure elucidation and antibacterial activity of new fungal metabolites of sclareol. | 2006 Jan |
|
| Cytotoxic and antitumor activity of liposome-incorporated sclareol against cancer cell lines and human colon cancer xenografts. | 2006 Jan |
|
| Synthesis of ent-thallusin. | 2006 May 11 |
|
| Antibacterial and cytotoxic activity of the acetone extract of the flowers of Salvia sclarea and some natural products. | 2007 Apr |
|
| Sclareol induces apoptosis in human HCT116 colon cancer cells in vitro and suppression of HCT116 tumor growth in immunodeficient mice. | 2007 Apr |
|
| Liposomes modify the subcellular distribution of sclareol uptake by HCT-116 cancer cell lines. | 2007 Feb-Apr |
|
| Calorimetric study on the induction of interdigitated phase in hydrated DPPC bilayers by bioactive labdanes and correlation to their liposome stability: The role of chemical structure. | 2007 Jan |
|
| Screening of terpenes and derivatives for antimycobacterial activity; identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro. | 2007 Oct |
|
| Fragrance material review on sclareol. | 2008 Nov |
|
| Hemisynthesis of two marine cheilanthane sesterterpenes from (-)-sclareol: first enantioselective synthesis of petrosaspongiolide R. | 2009 |
|
| Sclareol modulates the Treg intra-tumoral infiltrated cell and inhibits tumor growth in vivo. | 2010 |
|
| Chemical composition and antimicrobial activity of the essential oils from Cleome spinosa. | 2010 Aug |
|
| Identification and analysis of in planta expressed genes of Magnaporthe oryzae. | 2010 Feb 10 |
|
| Inhibition of angiogenesis- and inflammation-inducing factors in human colon cancer cells in vitro and in ovo by free and nanoparticle-encapsulated redox dye, DCPIP. | 2010 Jul 15 |
|
| A copal-8-ol diphosphate synthase from the angiosperm Cistus creticus subsp. creticus is a putative key enzyme for the formation of pharmacologically active, oxygen-containing labdane-type diterpenes. | 2010 Sep |
|
| Mitochondria-targeted liposomes improve the apoptotic and cytotoxic action of sclareol. | 2010 Sep |
Sample Use Guides
immunodeficient SCID mice: liposome-encapsulated sclareol
Route of Administration:
Intraperitoneal
Sclareol triggers phospholipid scrambling of the erythrocyte cell membrane, an effect in part due to activation of p38 kinase and casein kinase 1α. A 48 hours exposure of human erythrocytes to Sclareol (≥ 50 µM) significantly increased the percentage of annexin-V-binding cells without significantly modifying the average forward scatter. Sclareol (100 µM) significantly increased Fluo3-fluorescence, but the effect of Sclareol on annexin-V-binding was not significantly blunted by removal of extracellular Ca2+. Instead, the effect of Sclareol on annexin-V-binding was significantly blunted in the presence of p38 kinase inhibitor skepinone (2 µM) and in the presence of casein kinase 1α inhibitor D4476 (10 µM).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 20:08:58 GMT 2023
by
admin
on
Sat Dec 16 20:08:58 GMT 2023
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| Record UNII |
B607NP0Q8Y
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| Record Status |
Validated (UNII)
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| Record Version |
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EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION |
SCCS/1459/11
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admin on Sat Dec 16 20:08:58 GMT 2023 , Edited by admin on Sat Dec 16 20:08:58 GMT 2023
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208-194-0
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2007
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DTXSID0047111
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SCLAREOL
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515-03-7
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163263
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9053
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B607NP0Q8Y
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C070760
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| Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
ASSAY (GC)
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