Careful reexamination of the published 1H- and 13C-NMR spectral data of (22E)-24-methylcholesta-8(14),22-diene-3β,5α,6β,7α-tetraol (1), isolated from the marine-derived fungus Penicillium sp., indicates that, in reality, the compound is 5α,6α-epoxy-(22E,24R)-24-methylcholesta-8(14),22-diene-3β,7α-diol (5).
YaoitaY, KikuchiM, MachidaK. (2015) Structure revision of two polyoxygenated sterols from the marine sponge Neofibularia nolitangere. Natural Product Communications, 10, 881–883.
3.
YaoitaY, KikuchiM, MachidaK. (2014) Terpenoids and sterols from some Japanese mushrooms. Natural Product Communications, 9, 419–426.
4.
IshizukaT, YaoitaY, KikuchiM. (1997) Sterol constituents from the fruit bodies of Grifola frondosa (Fr.) S.F. Gray. Chemical & Pharmaceutical Bulletin, 45, 1756–1760.
5.
CarvalhoJFS, Manuel CruzSilva M, MoreiraJN, SimoesS, Luisa SaeMelo M. (2009) Efficient chemoenzymatic synthesis, cytotoxic evaluation, and SAR of epoxysterols. Journal of Medicinal Chemistry, 52, 4007–4019.
6.
KobayashiM, KandaF. (1991) Marine sterols. 18. Isolation and structure of four novel oxygenated sterols from a gorgonian coral Melithaea ocracea. Journal of the Chemical Society, Perkin Transactions1, 1177–1179.
7.
DellaGreca M, FiorentinoA, MolinaroA, MonacoP, PreviteraL. (1993) Steroidal 5,6-epoxides from Arum italicum. Natural Product Letters, 2, 27–32.
8.
MigliuoloA, PiccialliV, SicaD, GiordanoF. (1993) New A8- and A8(14)-5α,6α-epoxysterols from the marine sponge Spongia officinalis.Steroids, 58, 134–140.
9.
LuoX, LiF, ShindePB, HongJ, LeeC-O, ImKS, JungJH., (2006) 26,27-Cyclosterols and other polyoxygenated sterols from a marine sponge Topsentia sp. Journal of Natural Products, 69, 1760–1768.
10.
GaoH, HongK, ChenGD, WangCX, TangJS, YuY, JiangM-M, LiMM, WangNL, YaoXS., (2010) New oxidized sterols from Aspergillus awamori and the endo-boat conformation adopted by the cyclohexene oxide system. Magnetic Resonance in Chemistry, 48, 38–43.
