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Four new triterpenoidal saponins acylated with one monoterpenic acid from Gleditsia sinensis.
J Nat Prod. 1999 May; 62(5):740-5.JN

Abstract

Four new oleanane-type triterpenoidal glycosides, named gleditsiosides A-D (1-4), were isolated from the anomalous fruits of Gleditsia sinensis. Using modern NMR techniques, including DQF-COSY, HETCOR, HOHAHA, HMBC, and ROESY experiments and MS analysis as well as chemical methods, their structures were determined as 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- bet a-D-glucopyranosyl oleanolic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha- L-rhamnopyranosyl-(1-->2)-[(6S,2E)-6-hydroxy-2,6-dimethyl-2, 7-octadienoyl-(1-->6)]-beta-D-glucopyranosyl ester (1); 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- bet a-D-glucopyranosyl oleanolic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha- L-rhamnopyranosyl-(1-->2)-[(2E)-2-hydroxylmethyl-6-hydroxy-6-methy l-2 ,7-octadienoyl-(1-->6)]-beta-D-glucopyranosyl ester (2); 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- bet a-D-glucopyranosyl echinocystic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta- D-galactopyranosyl-(1-->2)]-alpha-L-rhamnopyranosyl-(1-->2)-[(2E)-2-h ydroxylmethyl-6-hydroxy-6-methyl-2, 7-octadienoyl-(1-->6)]-beta-D-glucopyranosyl ester (3); and 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- bet a-D-glucopyranosyl echinocystic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta- D-galactopyranosyl-(1-->2)]-alpha-L-rhamnopyranosyl-(1-->2)-[(6S, 2E)-6-hydroxy-2,6-dimethyl-2, 7-octadienoyl-(1-->6)]-beta-D-glucopyranosyl ester (4).

Authors+Show Affiliations

Department of Pharmacognosy, School of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba 274-8510, Japan.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

10346958

Citation

Zhang, Z, et al. "Four New Triterpenoidal Saponins Acylated With One Monoterpenic Acid From Gleditsia Sinensis." Journal of Natural Products, vol. 62, no. 5, 1999, pp. 740-5.
Zhang Z, Koike K, Jia Z, et al. Four new triterpenoidal saponins acylated with one monoterpenic acid from Gleditsia sinensis. J Nat Prod. 1999;62(5):740-5.
Zhang, Z., Koike, K., Jia, Z., Nikaido, T., Guo, D., & Zheng, J. (1999). Four new triterpenoidal saponins acylated with one monoterpenic acid from Gleditsia sinensis. Journal of Natural Products, 62(5), 740-5.
Zhang Z, et al. Four New Triterpenoidal Saponins Acylated With One Monoterpenic Acid From Gleditsia Sinensis. J Nat Prod. 1999;62(5):740-5. PubMed PMID: 10346958.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Four new triterpenoidal saponins acylated with one monoterpenic acid from Gleditsia sinensis. AU - Zhang,Z, AU - Koike,K, AU - Jia,Z, AU - Nikaido,T, AU - Guo,D, AU - Zheng,J, PY - 1999/5/29/pubmed PY - 1999/5/29/medline PY - 1999/5/29/entrez SP - 740 EP - 5 JF - Journal of natural products JO - J Nat Prod VL - 62 IS - 5 N2 - Four new oleanane-type triterpenoidal glycosides, named gleditsiosides A-D (1-4), were isolated from the anomalous fruits of Gleditsia sinensis. Using modern NMR techniques, including DQF-COSY, HETCOR, HOHAHA, HMBC, and ROESY experiments and MS analysis as well as chemical methods, their structures were determined as 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- bet a-D-glucopyranosyl oleanolic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha- L-rhamnopyranosyl-(1-->2)-[(6S,2E)-6-hydroxy-2,6-dimethyl-2, 7-octadienoyl-(1-->6)]-beta-D-glucopyranosyl ester (1); 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- bet a-D-glucopyranosyl oleanolic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha- L-rhamnopyranosyl-(1-->2)-[(2E)-2-hydroxylmethyl-6-hydroxy-6-methy l-2 ,7-octadienoyl-(1-->6)]-beta-D-glucopyranosyl ester (2); 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- bet a-D-glucopyranosyl echinocystic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta- D-galactopyranosyl-(1-->2)]-alpha-L-rhamnopyranosyl-(1-->2)-[(2E)-2-h ydroxylmethyl-6-hydroxy-6-methyl-2, 7-octadienoyl-(1-->6)]-beta-D-glucopyranosyl ester (3); and 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- bet a-D-glucopyranosyl echinocystic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta- D-galactopyranosyl-(1-->2)]-alpha-L-rhamnopyranosyl-(1-->2)-[(6S, 2E)-6-hydroxy-2,6-dimethyl-2, 7-octadienoyl-(1-->6)]-beta-D-glucopyranosyl ester (4). SN - 0163-3864 UR - https://www.unboundmedicine.com/medline/citation/10346958/Four_new_triterpenoidal_saponins_acylated_with_one_monoterpenic_acid_from_Gleditsia_sinensis_ L2 - https://doi.org/10.1021/np980441k DB - PRIME DP - Unbound Medicine ER -