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New saponins from Sechium mexicanum.
Magn Reson Chem. 2009 Nov; 47(11):994-1003.MR

Abstract

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.

Authors+Show Affiliations

Instituto de Recursos, Universidad del Mar, Puerto Angel, Oaxaca, 70900, México.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19637246

Citation

Hernández-Carlos, Beatriz, et al. "New Saponins From Sechium Mexicanum." Magnetic Resonance in Chemistry : MRC, vol. 47, no. 11, 2009, pp. 994-1003.
Hernández-Carlos B, Carmona-Pineda M, Villanueva-Cañongo C, et al. New saponins from Sechium mexicanum. Magn Reson Chem. 2009;47(11):994-1003.
Hernández-Carlos, B., Carmona-Pineda, M., Villanueva-Cañongo, C., López-Olguín, J. F., Aragón-García, A., & Joseph-Nathan, P. (2009). New saponins from Sechium mexicanum. Magnetic Resonance in Chemistry : MRC, 47(11), 994-1003. https://doi.org/10.1002/mrc.2487
Hernández-Carlos B, et al. New Saponins From Sechium Mexicanum. Magn Reson Chem. 2009;47(11):994-1003. PubMed PMID: 19637246.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - New saponins from Sechium mexicanum. AU - Hernández-Carlos,Beatriz, AU - Carmona-Pineda,Miriam, AU - Villanueva-Cañongo,Claudia, AU - López-Olguín,Jesús F, AU - Aragón-García,Agustín, AU - Joseph-Nathan,Pedro, PY - 2009/7/29/entrez PY - 2009/7/29/pubmed PY - 2010/1/5/medline SP - 994 EP - 1003 JF - Magnetic resonance in chemistry : MRC JO - Magn Reson Chem VL - 47 IS - 11 N2 - 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. SN - 1097-458X UR - https://www.unboundmedicine.com/medline/citation/19637246/New_saponins_from_Sechium_mexicanum_ L2 - https://doi.org/10.1002/mrc.2487 DB - PRIME DP - Unbound Medicine ER -