Parkeol

Parkeol

Names
IUPAC name lanosta-9(11),24-dien-3β-ol
Identifiers
ChEBI	CHEBI:63460
ChemSpider	23255009
Jmol interactive 3D	Image
PubChem	12313974
InChI InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,15,21-22,24-26,31H,9,11-14,16-19H2,1-8H3/t21-,22-,24-,25+,26+,28-,29-,30+/m1/s1 Key: MLVSYGCURCOSKP-FXCPCPCLSA-N
SMILES [H][C@@]1(CC[C@@]2(C)[C@]3([H])CC[C@@]4([H])C(C)(C)[C@@H](O)CC[C@]4(C)C3=CC[C@]12C)[C@H](C)CCC=C(C)C
Properties
Chemical formula	C30H50O
Molar mass	426.73 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

1. 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.
2. 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. PMID 21526825.
3. 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. PMID 14660793.