Sclareol

Last updated
Sclareol
Sclareol.svg
Names
IUPAC name
Labd-14-ene-8,13-diol
Systematic IUPAC name
(1R,2R,4aS,8aS)-1-[(3R)-3-Hydroxy-3-methylpent-4-en-1-yl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.450 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • 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 X mark.svgN
    Key: XVULBTBTFGYVRC-HHUCQEJWSA-N X mark.svgN
  • InChI=1/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
    Key: XVULBTBTFGYVRC-HHUCQEJWBX
  • CC1(C)CCC[C@@]2(C)[C@@]1([H])CC[C@@](C)(O)[C@@H]2CC[C@](O)(C)C=C
Properties
C20H36O2
Molar mass 308.506 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sclareol is a fragrant chemical compound found in Salvia sclarea , from which it derives its name. It is classified as a bicyclic diterpene alcohol. It is an amber colored solid with a sweet, balsamic scent. [1]

In an experiment in which sclareol was dissolved in jojoba oil and applied to mice, sclareol was detected in the blood (transdermal absorption) 30 minutes after application. [2] In this study, higher concentrations of sclareol were detected in liver homogenates than in blood. Although sclareol accumulation in the liver was suggested, it was concluded that no acute liver dysfunction was seen because AST and ALT were not elevated. Sclareol is also able to kill human leukemic cells and colon cancer cells in vitro by apoptosis. [3] [4]

Related Research Articles

<i>Salvia sclarea</i> Species of flowering plant

Salvia sclarea, the clary or clary sage, is a biennial or short-lived herbaceous perennial in the genus Salvia. It is native to the northern Mediterranean Basin, along with some areas in north Africa and Central Asia. The plant has a lengthy history as an herb and is currently grown for its essential oil.

K562 cells were the first human immortalised myelogenous leukemia cell line to be established. K562 cells are of the erythroleukemia type, and the cell line is derived from a 53-year-old female chronic myelogenous leukemia patient in blast crisis. The cells are non-adherent and rounded, are positive for the bcr:abl fusion gene, and bear some proteomic resemblance to both undifferentiated granulocytes and erythrocytes.

The epoxyeicosatrienoic acids or EETs are signaling molecules formed within various types of cells by the metabolism of arachidonic acid by a specific subset of cytochrome P450 enzymes termed cytochrome P450 epoxygenases. These nonclassic eicosanoids are generally short-lived, being rapidly converted from epoxides to less active or inactive dihydroxy-eicosatrienoic acids (diHETrEs) by a widely distributed cellular enzyme, soluble epoxide hydrolase (sEH), also termed epoxide hydrolase 2. The EETs consequently function as transiently acting, short-range hormones; that is, they work locally to regulate the function of the cells that produce them or of nearby cells. The EETs have been most studied in animal models where they show the ability to lower blood pressure possibly by a) stimulating arterial vasorelaxation and b) inhibiting the kidney's retention of salts and water to decrease intravascular blood volume. In these models, EETs prevent arterial occlusive diseases such as heart attacks and brain strokes not only by their anti-hypertension action but possibly also by their anti-inflammatory effects on blood vessels, their inhibition of platelet activation and thereby blood clotting, and/or their promotion of pro-fibrinolytic removal of blood clots. With respect to their effects on the heart, the EETs are often termed cardio-protective. Beyond these cardiovascular actions that may prevent various cardiovascular diseases, studies have implicated the EETs in the pathological growth of certain types of cancer and in the physiological and possibly pathological perception of neuropathic pain. While studies to date imply that the EETs, EET-forming epoxygenases, and EET-inactivating sEH can be manipulated to control a wide range of human diseases, clinical studies have yet to prove this. Determination of the role of the EETS in human diseases is made particularly difficult because of the large number of EET-forming epoxygenases, large number of epoxygenase substrates other than arachidonic acid, and the large number of activities, some of which may be pathological or injurious, that the EETs possess.

<span class="mw-page-title-main">Cordycepin</span> Chemical compound

Cordycepin, or 3'-deoxyadenosine, is a derivative of the nucleoside adenosine, differing from the latter by the replacement of the hydroxy group in the 3' position with a hydrogen. It was initially extracted from the fungus Cordyceps militaris, but can now be produced synthetically. It is also found in other Cordyceps species as well as Ophiocordyceps sinensis.

<span class="mw-page-title-main">Ursolic acid</span> Pentacyclic chemical compound found in fruits

Ursolic acid, is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme.

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<span class="mw-page-title-main">Free fatty acid receptor 3</span> Protein-coding gene in the species Homo sapiens

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<span class="mw-page-title-main">CD47</span> Protein-coding gene in humans

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<span class="mw-page-title-main">MECOM</span> Protein-coding gene in the species Homo sapiens

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<span class="mw-page-title-main">Sodium-coupled monocarboxylate transporter 1</span> Protein-coding gene in the species Homo sapiens

Sodium-coupled monocarboxylate transporter 1 (i.e., SMCT1) and sodium-coupled monocarboxylate transporter 2 (i.e., SMCT2) are plasma membrane transport proteins in the solute carrier family. They transport sodium cations in association with the anionic forms (see conjugated base) of certain short-chain fatty acids (i.e., SC-FAs) through the plasma membrane from the outside to the inside of cells. For example, propionic acid (i.e., CH
3
CH
2
CO
2
H
) in its anionic "propionate" form (i.e., CH
3
CH
2
CO
2
) along with sodium cations (i.e., Na+) are co-transported from the extracellular fluid into a SMCT1-epxressing cell's cytoplasm. Monocarboxylate transporters (MCTs) are also transport proteins in the solute carrier family. They co-transport the anionic forms of various compounds into cells in association with proton cations (i.e. H+). Four of the 14 MCTs, i.e. SLC16A1 (i.e., MCT1), SLC16A7 (i.e., MCT22), SLC16A8 (i.e., MCT3), and SLC16A3 (i.e., MCT4), transport some of the same SC-FAs anions that the SMCTs transport into cells. SC-FAs do diffuse into cells independently of transport proteins but at the levels normally occurring in tissues far greater amounts of the SC-FAs are brought into cells that express a SC-FA transporter.

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Sclareol cyclase (EC 3.1.7.4, geranylgeranyl pyrophosphate:sclareol cyclase, geranylgeranyl pyrophosphate-sclareol cyclase, GGPP:sclareol cyclase) is an enzyme with systematic name geranylgeranyl-diphosphate diphosphohydrolase (sclareol-forming). This enzyme catalyses the following chemical reaction

<span class="mw-page-title-main">Chrysophanol</span> Chemical compound

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<span class="mw-page-title-main">HCT116 cells</span>

HCT116 is a human colon cancer cell line used in therapeutic research and drug screenings.

hPG80 refers to the extracellular and oncogenic version of progastrin. This name first appeared in a scientific publication in January 2020. Until that date, scientific publications only mention 'progastrin', without necessarily explicitly specifying whether it is intracellular or extracellular in the tumor pathological setting.

References

  1. Good Scents Company
  2. Matsumoto, Yutaka; Horikawa, Kazumasa (2022). "Transdermal Absorption of Sclareol, an Active Ingredient in Clary Sage Oil: A Complementary and Alternative Medicine for Menopausal Symptoms". Women. 2 (3): 304–312. doi: 10.3390/women2030028 .
  3. Dimas, Kostas; Kokkinopoulos, Dimitrios; Demetzos, Costas; Vaos, Basilios; Marselos, Marios; Malamas, Mixalis; Tzavaras, Theodoros (1999). "The effect of sclareol on growth and cell cycle progression of human leukemic cell lines". Leukemia Research. 23 (3): 217–234. doi:10.1016/S0145-2126(98)00134-9. PMID   10071073.
  4. K. Dimas; Hatziantoniou, S; Tseleni, S; Khan, H; Georgopoulos, A; Alevizopoulos, K; Wyche, JH; Pantazis, P; Demetzos, C (2007). "Sclareol induces apoptosis in human HCT116 colon cancer cells in vitro and suppression of HCT116 tumor growth in immunodeficient mice". Apoptosis. 12 (4): 685–694. doi:10.1007/s10495-006-0026-8. PMID   17260186. S2CID   42171668.