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Triterpene glycosides from Astragalus icmadophilus.
Phytochemistry. 2010 Jun; 71(8-9):956-63.P

Abstract

Six cycloartane-type triterpene glycosides were isolated from Astragalus icmadophilus along with two known cycloartane-type glycosides, five known oleanane-type triterpene glycosides and one known flavonol glycoside. The structures of the six compounds were established as 3-O-[alpha-L-arabinopyranosyl-(1-->2)-O-3-acetoxy-alpha-L-arabinopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl-(1-->2)-O-beta-D-xylopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxy cycloartane, 3-O-[alpha-L-arabinopyranosyl-(1-->2)-O-3,4-diacetoxy-alpha-L-arabinopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane, 3-O-[alpha-L-arabinopyranosyl-(1-->2)-O-3-acetoxy-alpha-L-arabinopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,25-tetrahydroxy-20(R),24(S)-epoxycycloartane, 3-O-[alpha-L-arabinopyranosyl-(1-->2)-O-beta-D-xylopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24alpha-tetrahydroxy-20(R),25-epoxycycloartane, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl-(1-->2)-O-beta-D-xylopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24alpha-tetrahydroxy-20(R),25-epoxycycloartane by the extensive use of 1D- and 2D-NMR experiments along with ESIMS and HRMS analysis. The first four compounds are cyclocanthogenin and cycloastragenol glycosides, whereas the last two are based on cyclocephalogenin as aglycone, more unusual in the plant kingdom, so far reported only from Astragalus spp.

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Authors+Show Affiliations

Horo I
Ege University, Faculty of Science, Department of Chemistry, Bornova, Izmir, Turkey.
Bedir E
No affiliation info available
Perrone A
No affiliation info available
Ozgökçe F
No affiliation info available
Piacente S
No affiliation info available
Alankuş-Calişkan O
No affiliation info available

MeSH

Astragalus PlantGlycosidesMolecular StructureNuclear Magnetic Resonance, BiomolecularStereoisomerismTriterpenesTurkey

Pub Type(s)

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

Language

eng

PubMed ID

20231024

Citation

Horo, Ibrahim, et al. "Triterpene Glycosides From Astragalus Icmadophilus." Phytochemistry, vol. 71, no. 8-9, 2010, pp. 956-63.
Horo I, Bedir E, Perrone A, et al. Triterpene glycosides from Astragalus icmadophilus. Phytochemistry. 2010;71(8-9):956-63.
Horo, I., Bedir, E., Perrone, A., Ozgökçe, F., Piacente, S., & Alankuş-Calişkan, O. (2010). Triterpene glycosides from Astragalus icmadophilus. Phytochemistry, 71(8-9), 956-63. https://doi.org/10.1016/j.phytochem.2010.02.014
Horo I, et al. Triterpene Glycosides From Astragalus Icmadophilus. Phytochemistry. 2010;71(8-9):956-63. PubMed PMID: 20231024.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Triterpene glycosides from Astragalus icmadophilus. AU - Horo,Ibrahim, AU - Bedir,Erdal, AU - Perrone,Angela, AU - Ozgökçe,Fevzi, AU - Piacente,Sonia, AU - Alankuş-Calişkan,Ozgen, Y1 - 2010/03/16/ PY - 2010/01/21/received PY - 2010/02/10/revised PY - 2010/02/11/accepted PY - 2010/3/17/entrez PY - 2010/3/17/pubmed PY - 2010/8/7/medline SP - 956 EP - 63 JF - Phytochemistry JO - Phytochemistry VL - 71 IS - 8-9 N2 - Six cycloartane-type triterpene glycosides were isolated from Astragalus icmadophilus along with two known cycloartane-type glycosides, five known oleanane-type triterpene glycosides and one known flavonol glycoside. The structures of the six compounds were established as 3-O-[alpha-L-arabinopyranosyl-(1-->2)-O-3-acetoxy-alpha-L-arabinopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl-(1-->2)-O-beta-D-xylopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxy cycloartane, 3-O-[alpha-L-arabinopyranosyl-(1-->2)-O-3,4-diacetoxy-alpha-L-arabinopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane, 3-O-[alpha-L-arabinopyranosyl-(1-->2)-O-3-acetoxy-alpha-L-arabinopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,25-tetrahydroxy-20(R),24(S)-epoxycycloartane, 3-O-[alpha-L-arabinopyranosyl-(1-->2)-O-beta-D-xylopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24alpha-tetrahydroxy-20(R),25-epoxycycloartane, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl-(1-->2)-O-beta-D-xylopyranosyl]-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta,24alpha-tetrahydroxy-20(R),25-epoxycycloartane by the extensive use of 1D- and 2D-NMR experiments along with ESIMS and HRMS analysis. The first four compounds are cyclocanthogenin and cycloastragenol glycosides, whereas the last two are based on cyclocephalogenin as aglycone, more unusual in the plant kingdom, so far reported only from Astragalus spp. SN - 1873-3700 UR - https://www.unboundmedicine.com/medline/citation/20231024/Triterpene_glycosides_from_Astragalus_icmadophilus_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0031-9422(10)00058-0 DB - PRIME DP - Unbound Medicine ER -