Chemistry:Parkeol
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 from cycloartenol under Brønsted and Lewis acidic conditions[2][3], as a minor product by several oxidosqualene cyclase enzymes, and is the sole product of the enzyme parkeol synthase.[4]
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.[5]
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.
- ↑ 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" (in en). The Journal of Organic Chemistry 49 (4): 709–712. doi:10.1021/jo00178a030. ISSN 0022-3263. https://pubs.acs.org/doi/abs/10.1021/jo00178a030.
- ↑ 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" (in en). Journal of the American Chemical Society. doi:10.1021/jacs.5c22292. ISSN 0002-7863. https://pubs.acs.org/doi/10.1021/jacs.5c22292.
- ↑ 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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