Cycloartane glycosides from Sutherlandia frutescens.

Cycloartane glycosides from Sutherlandia frutescens.
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来自 Sutherlandia frutescens 的环阿麻苷。

DOI:
10.1021/np800328r
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发表时间:
2008-10
影响因子:
5.1
通讯作者:
Khan, Ikhlas A.
Khan, Ikhlas A.
中科院分区:
生物学2区
文献类型:
--
作者:
Fu, Xiang;Li, Xing-Cong;Smillie, Troy J.;Carvalho, Paulo;Mabusela, Wildfred;Syce, James;Johnson, Quinton;Folk, William;Avery, Mitchell A.;Khan, Ikhlas A.

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Four new cycloartane glycosides, sutherlandiosides A–D (1–4), were isolated from the South African folk medicine Sutherlandia frutescens and their structures established by spectroscopic methods and X-ray crystallography as 1S,3R,24S,25-tetrahydroxy-7S,10S-epoxy-9,10-seco-9,19-cyclolanost-9(11)-ene 25-O-β-d-glucopyranoside (1), 3R,7S,24S,25-tetrahydroxycycloartan-1-one 25-O-β-d-glucopyranoside (2), 3R,24S,25-trihydroxycycloartane-1,11-dione 25-O-β-d-glucopyranoside (3), and 7S,24S,25-trihydroxycycloart-2-en-1-one 25-O-β-d-glucoyranoside (4). Compound 1 represents the first secocycloartane skeleton possessing a 7,10-oxygen bridge. Compounds 2–4 are also the first examples of naturally occurring cycloartanes with a C-1 ketone functionality. Biosynthetic considerations and chemical evidence suggest that the presence of the C-1 ketone in 2 may facilitate the ring opening of the strained cyclopropane system.
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