Two novel triterpenoid pentasaccharides with an unusual glycosyl glycerol side chain from Ardisia crenata
✍ Scribed by Zhonghua Jia; Kazuo Koike; Tamotsu Nikaido; Taichi Ohmoto
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 815 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
A)rlroel:TwonoveltritapeaoidptatPeaccharideg~EMdF,waeisolusd~the roots of hdisia cretlata. They are the first examples of a tritelpc&d glycuside hybrid&d with a glycosylglycaol. lbtirstructllnswenmainlyestablisbedontkebasisoflligbfieldNMRstudies. IO additiuu, molecular mechanics nad dyoamics calctition studies showed that the lack of 13C glycosylation shift9 in tJse Rhamal-QG'lc~ and G'k$l+4Ama fmgmeata ia ud&mmMh E could be axrelatcdwithtbedisbniionofrhecomspoodingmrsicmangIes. Bo&compuodsexkibitedmotkrate itlbibiw activity on CAMP pbospbodiuuaape. Ardisia crenata Sims (Myrsinaceae) is a widely occurring shrub in the south part of China. Its roots have been used in the treatment of respiratory tract infections and menstrual diso&rs in Chinese traditional medicine, and showed sign&ant anti-fertility effects in modern pharmacological studies.* previous chemical studies showed that triterpenoid glycosides were the main components of this genns.2-4 Most mcently, we have reported the isolation and structure study of several tritetpenoid glycosides from A. crenaza.~~6 In this paper, we wish to report the isolation and strnctum study of two novel triterpenoid pemasaccharides. anlisicmnosides E (1) and F (2), from this source. RESULTS AND DISCUSSION Compound 1, an amorphous solid, [U]D + 30.4' (MeOH), has a molecular formnla of C&llo@51, as detetmined from its positive ion FARMS (m/z 1355 [M+H]+. 1377 [M+Na]+) and 13C. DRPT NMR spectra. Its spectral features and physichemical properties suggested 1 to be a tritupenoid glycoside. Of the 63 carbons, 30 wem assigned to the aglycone part, 29 to the oligosaccharlde moiety, one to a methoxyl group, and the mmaining 3 to a glycerol group (Tables 1 and2).