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• W37486146 abstract "Abstract Sterols and triterpenoids occur in all major groups of organisms, from fungi to humans, as secondary metabolites. It has been reported that various sterols and triterpenoids isolated from mushrooms to possess inhibitory activities on inflammation induced by 12- O -tetradecanoyl-phorbol-13-acetate (TPA), a well-known tumor promoter, and for tumor promotion in two-stage carcinogenesis in mice. Therefore, these compounds may possibly prove useful for producing cancer chemopreventive agents. Over the past 20 years, our research group has been involved in the phytochemical study of sterols and triterpenoids from mushrooms. From 18 species, namely, Amanita pantherina , Amanita virgineoids , Daedaleopsis tricolor , Flammulina velutipes , Grifola frondosa , Hypsizigus marmoreus , Lentinula edodes , Lyophyllum shimeji , Naematoloma sublateritium , Omphalia lapidescens , Panellus serotinus , Pholiota nameko , Pleurotus eryngii , Pl. ostreatus , Polyporus umbellatus , Sarcodon aspratus , Tricholoma matustake , and T. portentosum , we isolated 28 new sterols and 3 new triterpenoids. In this review, structural features of a sterol having Δ 5,8 structure ( 1 ), six sterols having 5α,6α-epoxy group ( 2 – 7 ), five sterols having 5α,9α-epidioxy group ( 8 – 12 ), six sterols having enone, diene, and ketone ( 13 – 18 ), four sterols having 3,5,6,9-tetrol and 3,5,6,7-tetrol structures ( 19 – 22 ), a sterol having 1,2,3,4,5,10,19-heptanor structure ( 23 ), five 23-methylergostane-type sterols ( 24 – 28 ), and three lanostane-type triterpenoids ( 29 – 31 ) are discussed. The structures of compounds 1 – 31 are shown below. Among these, compounds 2 – 4 are the first examples of a naturally occurring 5α,6α-epoxy-3β,7β-dihydroxy-Δ 8 -sterol, a 5α,6α-epoxy-3β,7β,14α-trihydroxy-Δ 8 -sterol, and a 5α,6α-epoxy-3β,7α-dihydroxy-Δ 8,14 -sterol, respectively. 5α,6α;8α,9α-Diepoxy-3β,7α-dihydroxy ( 6 ) and 5α,6α;8α,9α-diepoxy-3β,7β-dihydr-oxy moieties ( 7 ) are unprecedented in the natural sterols previously known. Compounds 8 – 12 are the first example of a naturally occurring 5α,9α-epidioxy sterol. Compounds 15 and 16 are the first examples of a naturally occurring 3β,5α,9α,14α-tetrahydroxy-7-en-6-one sterol and a 3β,5α,9α,14β-tetrahydroxy-7-en-6-one sterol, respectively. Compounds 17 and 18 are the first examples of a naturally occurring 3β,5α,6β-trihydroxy-Δ 7,9(11) -sterol and a 3β,5α,6β-trihydroxy-7-keto sterol, respectively. Although a sterol with the (22 E ,24 R )-23,24-dimethyl-Δ 22 -side chain has been detected in marine organisms, the isolation of a sterol with this side chain ( 24 – 28 ) from terrestrial sources is rare." @default.
• W37486146 created "2016-06-24" @default.
• W37486146 creator A5049707282 @default.
• W37486146 creator A5054778059 @default.
• W37486146 creator A5064201194 @default.
• W37486146 date "2015-01-01" @default.
• W37486146 modified "2023-10-02" @default.
• W37486146 title "Terpenoids and Sterols from Mushrooms" @default.
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