Chemistry:Parkeol
From HandWiki
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| IUPAC name
Lanosta-9(11),24-dien-3β-ol
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| Systematic IUPAC name
(1R,3aS,3bS,5aR,7S,9aS,11aR)-3a,6,6,9a,11a-Pentamethyl-1-[(2R)-6-methylhept-5-en-2-yl]-2,3,3a,3b,4,5,5a,6,7,8,9,9a,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol | |
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C30H50O | |
| Molar mass | 426.729 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Parkeol is a relatively uncommon sterol secondary metabolite found mostly in plants, particularly noted in Butyrospermum parkii (now called Vitellaria paradoxa, or the shea tree).[1] It can be synthesized as a minor product by several oxidosqualene cyclase enzymes, and is the sole product of the enzyme parkeol synthase.[2]
Parkeol is the dominant sterol found in the planctomycete Gemmata obscuriglobus, a rare example of a sterol-synthesizing prokaryote. The only other sterol identified in this organism is lanosterol, a key component of the sterol biosynthetic pathway in animals and fungi; this relatively limited sterol repertoire may resemble the early evolution of sterol synthesis, which is ubiquitous in eukaryotes.[3]
References
- ↑ Itoh, Toshihiro; Uetsuki, Toshimitsu; Tamura, Toshitake; Matsumoto, Taro (June 1980). "Characterization of triterpene alcohols of seed oils from some species of theaceae, phytolaccaceae and sapotaceae". Lipids 15 (6): 407–411. doi:10.1007/BF02534064.
- ↑ Ito, R; Mori, K; Hashimoto, I; Nakano, C; Sato, T; Hoshino, T (20 May 2011). "Triterpene cyclases from Oryza sativa L.: cycloartenol, parkeol and achilleol B synthases.". Organic Letters 13 (10): 2678–81. doi:10.1021/ol200777d. PMID 21526825.
- ↑ Pearson, A; Budin, M; Brocks, JJ (23 December 2003). "Phylogenetic and biochemical evidence for sterol synthesis in the bacterium Gemmata obscuriglobus.". Proceedings of the National Academy of Sciences of the United States of America 100 (26): 15352–7. doi:10.1073/pnas.2536559100. PMID 14660793. Bibcode: 2003PNAS..10015352P.
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