Parkeol

Parkeol
Names
IUPAC name
Lanosta-9(11),24-dien-3β-ol
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
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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
  • [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
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).

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). It can be synthesized from cycloartenol under Brønsted and Lewis acidic conditions, as a minor product by several oxidosqualene cyclase enzymes, and is the sole product of the parkeol synthase enzyme.

Parkeol is the dominant sterol found Gemmata obscuriglobus, a planctomycete and 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.

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. S2CID 25505422.
  2. ↑ Shimizu, Naoto; Itoh, Toshihiro; Saito, Masao; Matsumoto, Taro (February 1984). "Acid-catalyzed isomerization of cycloartane triterpene alcohols. The formation of cucurbitane- and lanostane-type isomers". The Journal of Organic Chemistry. 49 (4): 709–712. doi:10.1021/jo00178a030. ISSN 0022-3263.
  3. ↑ Kizakis, Manuel; Treger, Marvin; Dräger, Gerald; König, Carolin; Heretsch, Philipp (2026-03-26). "Navigating the Landscape of Cycloartanyl Cations: Synthesis of Fortunefuroic Acid I, Parkeol, 25,26,27-Trinor-3α-hydroxy-17,13-friedolanosta-8,12-dien-23-one, and Spirochensilide A". Journal of the American Chemical Society. doi:10.1021/jacs.5c22292. ISSN 0002-7863.
  4. ↑ 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.
  5. ↑ 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. Bibcode:2003PNAS..10015352P. doi:10.1073/pnas.2536559100. PMC 307571. PMID 14660793.