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The first euphane-type triterpene tridesmosides and bisdesmoside from Rhoiptelea chiliantha

✍ Scribed by Zhi-Hong Jiang; Takashi Tanaka; Haruko Hirata; Reiko Fukuoka; Isao Kouno


Book ID
104208218
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
504 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis


Two euphane-type triterpene a'idesmosides rhoiptelesides A (1) and B (2), and a bisdesmoside, rhoipteleside E (3) were isolated from the leaves and fruits of Rhoiptelea chiliantha Diels et Hand.-Mazz. (Rhoipteleaceae). Their structures were elucidated on the basis of extensive analysis of their 1D and 2D-NMR spectral data and chemical evidence. These compounds represent the first example of the glycoside of euphane-type triterpene. Β© 1997 Elsevier Science Ltd. 28.4 28.4 28.2 28.2 a) 125 Ml-lz in CD3OD; b) 125 MHz in C5D5N; c) 75 MHz in CD3OD The detailed analyses of the aglycone signals using the 1H-1H COSY and HSQC techniques disclosed three partial structural units shown by heavy lines in Fig. 1. This was also supported by analysis of the HMBC spectrum, which showed the two-and three-bond correlations between H-1 and C-2; between H-3 and C-1, between H-7 and both C-5 and C-9; between H-11 and C-12; between H3-21 and C-17, C-20 and C-22; between H-23 and C-20; and between H-24 and C-22, C-26 and C-27 (Fig. 1), respectively, confirmed above three partial structures. Furthermore, the HMBC correlations of the five individual tertiary methyl signals on the rings A-D [between H3-28 (8 0.95) and C-29, C-4 and C-3; between H3-29 (8 0.96) and both C-28 and C-5; between H3-19 (8 0.94) and C-l, C-5 and C-9; between H3-30 (8 0.93) and C-8, C-13 and C-15; and between H3-18 (8 0.91) and C-12, C-13 and C-17] firmly established the linkages of these partial structural units. Thus, the plane structure of the aglycone was unequivocally elucidated as shown in Fig. 1. The locations of two rhamnoses and a fucose at C-3 (8 80.8), C-23 (8 71.4) and C-11 (5 72.3), respectively, were also established by the observation of the HMBC correlations of the oxygen-beating carbon signals of the


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