Cycloartenol

Last updated
Cycloartenol
Cycloartenol.svg
Cycloartenol molecule ball.png
Names
IUPAC name
9,19-Cyclo-9β-lanost-24-en-3β-ol
Systematic IUPAC name
(1R,3aS,3bS,5aR,7S,9aR,10aS,12aR)-3a,6,6,12a-Tetramethyl-1-[(2R)-6-methylhept-5-en-2-yl]tetradecahydro-2H,10H-cyclopenta[a]cyclopropa[e]phenanthren-7-ol
Other names
9β,19-cyclo-24-lanosten-3β-ol,
(3β)-9,19-Cyclolanost-24-en-3-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • InChI=1S/C30H50O/c1-20(2)9-8-10-21(3)22-13-16-28(7)24-12-11-23-26(4,5)15-14-25(31)30(23)19-29(24,30)18-17-27(22,28)6/h14,20-24,31H,8-13,15-19H2,1-7H3/t21-,22-,23+,24+,27-,28+,29+,30-/m1/s1 Yes check.svgY
    Key: UYPYBUZTJLFCHS-DGUMGERNSA-N Yes check.svgY
  • InChI=1/C30H50O/c1-20(2)9-8-10-21(3)22-13-16-28(7)24-12-11-23-26(4,5)15-14-25(31)30(23)19-29(24,30)18-17-27(22,28)6/h14,20-24,31H,8-13,15-19H2,1-7H3/t21-,22-,23+,24+,27-,28+,29+,30-/m1/s1
    Key: UYPYBUZTJLFCHS-DGUMGERNBH
  • CC(CCC=C(C)C)C1CCC2(C1(CCC34C2CCC5C3(C4)CCC(C5(C)C)O)C)C
  • CC(C)CCC[C@@H](C)[C@H]5CC[C@]1(C)[C@]5(C)CC[C@]24C[C@]34C(/O)=C\C[C@@](C)(C)[C@@H]3CC[C@@H]12
Properties
C30H50O
Molar mass 426.72 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Cycloartenol is an important triterpenoid often found in plants. It belongs to the sterol class of steroids. It is the starting point for the synthesis of almost all plant steroids, [1] making them chemically distinct from the steroids of fungi and animals, which are, instead, produced from lanosterol.

Synthesis

The biosynthesis of cycloartenol starts from the triterpenoid squalene. It is the first precursor in the biosynthesis of other stanols and sterols, referred to as phytostanols and phytosterols in photosynthetic organisms and plants. The identities and distribution of phytostanols and phytosterols is characteristic of a plant species.

Related Research Articles

<span class="mw-page-title-main">Cholesterol</span> Sterol biosynthesized by all animal cells

Cholesterol is the principal sterol of all higher animals, distributed in body tissues, especially the brain and spinal cord, and in animal fats and oils.

<span class="mw-page-title-main">Steroid</span> Polycyclic organic compound having sterane as a core structure

A steroid is an organic compound with four fused rings arranged in a specific molecular configuration.

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

Sterol is an organic compound with formula C
17
H
28
O
, whose molecule is derived from that of gonane by replacement of a hydrogen atom on C3 position by a hydroxyl group. It is therefore an alcohol of gonane. More generally, any compounds that contain the gonane structure, additional functional groups, and/or modified ring systems derived from gonane are called steroids. Therefore, sterols are a subgroup of the steroids. They occur naturally in most eukaryotes, including plants, animals, and fungi, and can also be produced by some bacteria. The most familiar type of animal sterol is cholesterol, which is vital to cell membrane structure, and functions as a precursor to fat-soluble vitamins and steroid hormones.

<span class="mw-page-title-main">Phytosterol</span> Class of steroids derived from plants

Phytosterols are phytosteroids, similar to cholesterol, that serve as structural components of biological membranes of plants. They encompass plant sterols and stanols. More than 250 sterols and related compounds have been identified. Free phytosterols extracted from oils are insoluble in water, relatively insoluble in oil, and soluble in alcohols.

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

Campesterol is a phytosterol whose chemical structure is similar to that of cholesterol, and is one of the ingredients for E number E499.

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

Stigmasterol – a plant sterol (phytosterol) – is among the most abundant of plant sterols, having a major function to maintain the structure and physiology of cell membranes. In the European Union, it is a food additive listed with E number E499, and may be used in food manufacturing to increase the phytosterol content, potentially lowering the levels of LDL cholesterol.

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

Lanosterol is a tetracyclic triterpenoid and is the compound from which all animal and fungal steroids are derived. By contrast, plant steroids are produced via cycloartenol.

<i>beta</i>-Sitosterol Chemical compound

β-sitosterol (beta-sitosterol) is one of several phytosterols with chemical structures similar to that of cholesterol. It is a white, waxy powder with a characteristic odor, and is one of the components of the food additive E499. Phytosterols are hydrophobic and soluble in alcohols.

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

Cholestane is a saturated tetracyclic triterpene. This 27-carbon biomarker is produced by diagenesis of cholesterol and is one of the most abundant biomarkers in the rock record. Presence of cholestane, its derivatives and related chemical compounds in environmental samples is commonly interpreted as an indicator of animal life and/or traces of O2, as animals are known for exclusively producing cholesterol, and thus has been used to draw evolutionary relationships between ancient organisms of unknown phylogenetic origin and modern metazoan taxa. Cholesterol is made in low abundance by other organisms (e.g., rhodophytes, land plants), but because these other organisms produce a variety of sterols it cannot be used as a conclusive indicator of any one taxon. It is often found in analysis of organic compounds in petroleum.

<span class="mw-page-title-main">Triterpene</span> Class of chemical compounds

Triterpenes are a class of terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the precursor to all steroids.

<span class="mw-page-title-main">Ginsenoside</span> Class of steroids

Ginsenosides or panaxosides are a class of natural product steroid glycosides and triterpene saponins. Compounds in this family are found almost exclusively in the plant genus Panax (ginseng), which has a long history of use in traditional medicine that has led to the study of pharmacological effects of ginseng compounds. As a class, ginsenosides exhibit a large variety of subtle and difficult-to-characterize biological effects when studied in isolation.

In enzymology, a sterol 24-C-methyltransferase is an enzyme that catalyzes the chemical reaction

The molecular formula C30H50O may refer to:

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

Stigmastanol (sitostanol) is a phytosterol found in a variety of plant sources. Similar to sterol esters and stanol esters, stigmastanol inhibits the absorption of cholesterol from the diet. Animal studies suggest that it also inhibits biosynthesis of cholesterol in the liver.

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

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<span class="mw-page-title-main">Viridin</span> Chemical compound: furanosteroid

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<span class="mw-page-title-main">Oxidosqualene cyclase</span>

Oxidosqualene cyclases (OSC) are enzymes involved in cyclization reactions of 2,3-oxidosqualene to form sterols or triterpenes.

Pierre Benveniste, born on 22 December 1937 in Neuilly-sur-Seine, is a French researcher in plant biochemistry and professor at the University of Strasbourg.

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

29- or 31-Norcycloartenol, also called 4α,14α-dimethyl-9β,19-cyclo-5α-cholest-24-en-3β-ol, is a Metabolic intermediate of plant sterol biosynthesis. In the pathway, it is transformed from demethylation of cycloartenol, then 9,19-cyclopropyl-ring opening reaction occurs to 29-Norlanosterol.

References

  1. Schaller, Hubert (May 2003). "The role of sterols in plant growth and development". Progress in Lipid Research. 42 (3): 163–175. doi:10.1016/S0163-7827(02)00047-4. PMID   12689617.