Furostane-Type Steroidal Saponins from the Roots of Chlorophytum borivilianum
✍ Scribed by Debabrata Acharya; Anne-Claire Mitaine-Offer; Nutan Kaushik; Tomofumi Miyamoto; Thomas Paululat; Marie-Aleth Lacaille-Dubois
- Publisher
- John Wiley and Sons
- Year
- 2008
- Tongue
- German
- Weight
- 193 KB
- Volume
- 91
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
Four new furostanol steroid saponins, borivilianosides A–D (1–4, resp.), corresponding to (3__β__,5__α__,22__R__,25__R__)‐26‐(β‐D‐glucopyranosyloxy)‐22‐hydroxyfurostan‐3‐yl O‐β‐D‐xylopyranosyl‐(1→3)‐O‐β‐D‐glucopyranosyl‐(1→4)‐O‐[α‐L‐rhamnopyranosyl‐(1→2)]‐β‐D‐galactopyranoside (1), (3__β__,5__α__,22__R__,25__R__)‐ 26‐(β‐D‐glucopyranosyloxy)‐22‐methoxyfurostan‐3‐yl O‐β‐D‐xylopyranosyl‐(1→3)‐O‐β‐D‐glucopyranosyl‐(1→4)‐O‐[α‐L‐rhamnopyranosyl‐(1→2)]‐β‐D‐galactopyranoside (2), (3__β__,5__α__,22__R__,25__R__)‐26‐(β‐D‐glucopyranosyloxy)‐22‐methoxyfurostan‐3‐yl O‐β‐D‐xylopyranosyl‐(1→3)‐O‐[β‐D‐glucopyranosyl‐(1→2)]‐O‐β‐D‐glucopyranosyl‐(1→4)‐β‐D‐galactopyranoside (3), and (3__β__,5__α__,25__R__)‐26‐(β‐D‐glucopyranosyloxy)furost‐20(22)‐en‐3‐yl O‐β‐D‐xylopyranosyl‐(1→3)‐O‐[β‐D‐glucopyranosyl‐(1→2)]‐O‐β‐D‐glucopyranosyl‐(1→4)‐β‐D‐galactopyranoside (4), together with the known tribuluside A and (3__β__,5__α__,22__R__,25__R__)‐26‐(β‐D‐glucopyranosyloxy)‐22‐methoxyfurostan‐3‐yl O‐β‐D‐xylopyranosyl‐(1→2)‐O‐[β‐D‐xylopyranosyl‐(1→3)]‐O‐β‐D‐glucopyranosyl‐(1→4)‐O‐[α‐L‐rhamnopyranosyl‐(1→2)]‐β‐D‐galactopyranoside were isolated from the dried roots of Chlorophytum borivilianum Sant and Fern. Their structures were elucidated by 2D‐NMR analyses (COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry.
📜 SIMILAR VOLUMES
A nom2 steroidal glycoside has been isolated from the starfish Protoreaster nodosus. The structure includes a 3B,5a,6B,8B,lScr,24S-hexahydroxysteroidal moiety and a sugar moiety [2-0-methyl-B-D-xylopyranosyl-(1 + 21-a-L-arabinofuranosyZ]which is glycosidicaZZy attached at C-24 of the aglycone.
NEARLY twenty years ago, Marker et al. (1) suggested that the true naturally occurring steroidal saponins synthesized by plants might have an open side chain moiety in which ring closure to the spiroketal structure encountered in the corresponding sapogenins is prevented by conjugation of the hydrox