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Glandulosides A-D, triterpene saponins from Acanthophyllum glandulosum.
J Nat Prod. 2004 Jul; 67(7):1114-8.JN

Abstract

Four novel triterpenoid saponins, glandulosides A (1), B (2), C (3), and D (4), together with two known saponins (5 and 6) have been isolated from the roots of Acanthophyllum glandulosum. Their structures were elucidated using a combination of homo- and heteronuclear 2D NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FABMS. The new compounds were characterized as 23-O-beta-D-galactopyranosylgypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[beta-d-galactopyranosyl-(1-->6)]-beta-D-galactopyranoside (1), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-3-O-acetyl-beta-D-fucopyranoside (2), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-3,4-di-O-acetyl-beta-D-fucopyranoside (3), and 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-[3-O-acetyl-beta-D-quinovopyranosyl-(1-->4)]-beta-D-fucopyranoside (4).

Authors+Show Affiliations

Gaidi G
Laboratoire de Pharmacognosie, Unité de Molécules d'Intérêt Biologique (UMIB), EA 3660, Faculté de Pharmacie, Université de Bourgogne, 7, Boulevard Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France.
Miyamoto T
No affiliation info available
Ramezani M
No affiliation info available
Lacaille-Dubois MA
No affiliation info available

MeSH

CaryophyllaceaeIranMolecular StructureNuclear Magnetic Resonance, BiomolecularPlant RootsPlants, MedicinalSaponinsStereoisomerismTriterpenes

Pub Type(s)

Journal Article

Language

eng

PubMed ID

15270563

Citation

Gaidi, Ghezala, et al. "Glandulosides A-D, Triterpene Saponins From Acanthophyllum Glandulosum." Journal of Natural Products, vol. 67, no. 7, 2004, pp. 1114-8.
Gaidi G, Miyamoto T, Ramezani M, et al. Glandulosides A-D, triterpene saponins from Acanthophyllum glandulosum. J Nat Prod. 2004;67(7):1114-8.
Gaidi, G., Miyamoto, T., Ramezani, M., & Lacaille-Dubois, M. A. (2004). Glandulosides A-D, triterpene saponins from Acanthophyllum glandulosum. Journal of Natural Products, 67(7), 1114-8.
Gaidi G, et al. Glandulosides A-D, Triterpene Saponins From Acanthophyllum Glandulosum. J Nat Prod. 2004;67(7):1114-8. PubMed PMID: 15270563.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Glandulosides A-D, triterpene saponins from Acanthophyllum glandulosum. AU - Gaidi,Ghezala, AU - Miyamoto,Tomofumi, AU - Ramezani,Mohammad, AU - Lacaille-Dubois,Marie-Aleth, PY - 2004/7/24/pubmed PY - 2004/9/9/medline PY - 2004/7/24/entrez SP - 1114 EP - 8 JF - Journal of natural products JO - J Nat Prod VL - 67 IS - 7 N2 - Four novel triterpenoid saponins, glandulosides A (1), B (2), C (3), and D (4), together with two known saponins (5 and 6) have been isolated from the roots of Acanthophyllum glandulosum. Their structures were elucidated using a combination of homo- and heteronuclear 2D NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FABMS. The new compounds were characterized as 23-O-beta-D-galactopyranosylgypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[beta-d-galactopyranosyl-(1-->6)]-beta-D-galactopyranoside (1), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-3-O-acetyl-beta-D-fucopyranoside (2), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-3,4-di-O-acetyl-beta-D-fucopyranoside (3), and 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl-(1-->2)-[3-O-acetyl-beta-D-quinovopyranosyl-(1-->4)]-beta-D-fucopyranoside (4). SN - 0163-3864 UR - https://www.unboundmedicine.com/medline/citation/15270563/Glandulosides_A_D_triterpene_saponins_from_Acanthophyllum_glandulosum_ DB - PRIME DP - Unbound Medicine ER -