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Biologically active secondary metabolites from Ginkgo biloba.
J Agric Food Chem. 2002 May 22; 50(11):3150-5.JA

Abstract

Three new compounds, (7E)-2beta,3alpha-dihydroxy-megastigm-7-en-9-one (1), 3-[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-8-yl]-4-methoxybenzoic acid (2), and 4'-O-methyl myricetin 3-O-(6-O-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside (3), were isolated from Ginkgo biloba, together with 27 known compounds. The structures of the new compounds were determined primarily from 1D- and 2D-NMR analysis. The 4-O-methylbenzoic acid structural feature at C-8 in 2 is encountered for the first time. The antioxidant activities of 29 compounds isolated from Ginkgo biloba were evaluated on intracellular reactive oxygen species in HL-60 cells. It was found that quercetin, kampferol, and tamarixetin had antioxidant activity that was approximately 3-fold greater than that of their respective glycosides and also approximately 3-fold greater than that of a standard ascorbic acid with an IC(50) at maximum effectiveness.

Authors+Show Affiliations

National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, and Department of Pharmacology and Pharmacognosy, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, USA.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Comparative Study
Journal Article
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

12009978

Citation

Bedir, Erdal, et al. "Biologically Active Secondary Metabolites From Ginkgo Biloba." Journal of Agricultural and Food Chemistry, vol. 50, no. 11, 2002, pp. 3150-5.
Bedir E, Tatli II, Khan RA, et al. Biologically active secondary metabolites from Ginkgo biloba. J Agric Food Chem. 2002;50(11):3150-5.
Bedir, E., Tatli, I. I., Khan, R. A., Zhao, J., Takamatsu, S., Walker, L. A., Goldman, P., & Khan, I. A. (2002). Biologically active secondary metabolites from Ginkgo biloba. Journal of Agricultural and Food Chemistry, 50(11), 3150-5.
Bedir E, et al. Biologically Active Secondary Metabolites From Ginkgo Biloba. J Agric Food Chem. 2002 May 22;50(11):3150-5. PubMed PMID: 12009978.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Biologically active secondary metabolites from Ginkgo biloba. AU - Bedir,Erdal, AU - Tatli,Irem I, AU - Khan,Riaz A, AU - Zhao,Jianping, AU - Takamatsu,Satoshi, AU - Walker,Larry A, AU - Goldman,Peter, AU - Khan,Ikhlas A, PY - 2002/5/16/pubmed PY - 2002/7/6/medline PY - 2002/5/16/entrez SP - 3150 EP - 5 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 50 IS - 11 N2 - Three new compounds, (7E)-2beta,3alpha-dihydroxy-megastigm-7-en-9-one (1), 3-[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-8-yl]-4-methoxybenzoic acid (2), and 4'-O-methyl myricetin 3-O-(6-O-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside (3), were isolated from Ginkgo biloba, together with 27 known compounds. The structures of the new compounds were determined primarily from 1D- and 2D-NMR analysis. The 4-O-methylbenzoic acid structural feature at C-8 in 2 is encountered for the first time. The antioxidant activities of 29 compounds isolated from Ginkgo biloba were evaluated on intracellular reactive oxygen species in HL-60 cells. It was found that quercetin, kampferol, and tamarixetin had antioxidant activity that was approximately 3-fold greater than that of their respective glycosides and also approximately 3-fold greater than that of a standard ascorbic acid with an IC(50) at maximum effectiveness. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/12009978/Biologically_active_secondary_metabolites_from_Ginkgo_biloba_ L2 - https://doi.org/10.1021/jf011682s DB - PRIME DP - Unbound Medicine ER -