New saponins from Sechium mexicanum.
The chemical study of Sechium mexicanum roots led to the isolation of the two new saponins {3-O-beta-D-glucopyranosyl (1 --> 3)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1 --> 3)-beta-D-xylopyranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranoside} (1) and {3-O-beta-D-glucopyranosyl (1 --> 3)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1 --> 3)-beta-D-xylopyranosyl-(1 --> 4)-[beta-D-apiosyl-(1 --> 3)]-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranoside} (2), together with the known compounds {3-O-beta-D-glucopyranosyl-(1 --> 3)-beta-D-glucopyranosyl-2beta,3beta,6beta,16alpha,23-pentahydroxyolean-12-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1 --> 3)-beta-D-xylopyranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranoside} (3), tacacosides A(1) (4) and B(3) (5). The structures of saponins 1 and 2 were elucidated using a combination of (1)H and (13)C 1D-NMR, COSY, TOCSY, gHMBC and gHSQC 2D-NMR, and FABMS of the natural compounds and their peracetylated derivates, as well as by chemical degradation. Compounds 1-3 are the first examples of saponins containing polygalacic and 16-hydroxyprotobasic acids found in the genus Sechium, while 4 and 5, which had been characterized partially by NMR, are now characterized in detail.
Hernández-Carlos
Beatriz
B
Instituto de Recursos, Universidad del Mar, Puerto Angel, Oaxaca, 70900, México.
Carmona-Pineda
Miriam
M
Villanueva-Cañongo
Claudia
C
López-Olguín
Jesús F
JF
Aragón-García
Agustín
A
Joseph-Nathan
Pedro
P
D019662:Cucurbitaceae / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D010936:Plant Extracts / Q000737:chemistry*; D018517:Plant Roots / Q000737:chemistry*; D012503:Saponins / Q000737:chemistry* / Q000145:classification
D010936:Plant Extracts; D012503:Saponins