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Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.
J Nat Prod. 2002 Dec; 65(12):1909-14.JN

Abstract

Fatty acid synthase (FAS) has been identified as a potential antifungal target. FAS prepared from Saccharomyces cerevisiae was employed for bioactivity-guided fractionation of Chlorophora tinctoria,Paspalum conjugatum, Symphonia globulifera, Buchenavia parviflora, and Miconia pilgeriana. Thirteen compounds (1-13), including three new natural products (1, 4, 12), were isolated and their structures identified by spectroscopic interpretation. They represented five chemotypes, namely, isoflavones, flavones, biflavonoids, hydrolyzable tannin-related derivatives, and triterpenoids. 3'-Formylgenistein (1) and ellagic acid 4-O-alpha-l-rhamnopyranoside (9) were the most potent compounds against FAS, with IC(50) values of 2.3 and 7.5 microg/mL, respectively. Furthermore, 43 (14-56) analogues of the five chemotypes from our natural product repository and commercial sources were tested for their FAS inhibitory activity. Structure-activity relationships for some chemotypes were investigated. All these compounds were further evaluated for antifungal activity against Candida albicans and Cryptococcus neoformans. Although there were several antifungal compounds in the set, correlation between the FAS inhibitory activity and antifungal activity could not be defined.

Authors+Show Affiliations

National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS 38677, USA. xli@olemiss.eduNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

12502337

Citation

Li, Xing-Cong, et al. "Fatty Acid Synthase Inhibitors From Plants: Isolation, Structure Elucidation, and SAR Studies." Journal of Natural Products, vol. 65, no. 12, 2002, pp. 1909-14.
Li XC, Joshi AS, ElSohly HN, et al. Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies. J Nat Prod. 2002;65(12):1909-14.
Li, X. C., Joshi, A. S., ElSohly, H. N., Khan, S. I., Jacob, M. R., Zhang, Z., Khan, I. A., Ferreira, D., Walker, L. A., Broedel, S. E., Raulli, R. E., & Cihlar, R. L. (2002). Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies. Journal of Natural Products, 65(12), 1909-14.
Li XC, et al. Fatty Acid Synthase Inhibitors From Plants: Isolation, Structure Elucidation, and SAR Studies. J Nat Prod. 2002;65(12):1909-14. PubMed PMID: 12502337.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies. AU - Li,Xing-Cong, AU - Joshi,Alpana S, AU - ElSohly,Hala N, AU - Khan,Shabana I, AU - Jacob,Melissa R, AU - Zhang,Zhizheng, AU - Khan,Ikhlas A, AU - Ferreira,Daneel, AU - Walker,Larry A, AU - Broedel,Sheldon E,Jr AU - Raulli,Robert E, AU - Cihlar,Ronald L, PY - 2002/12/28/pubmed PY - 2003/5/6/medline PY - 2002/12/28/entrez SP - 1909 EP - 14 JF - Journal of natural products JO - J Nat Prod VL - 65 IS - 12 N2 - Fatty acid synthase (FAS) has been identified as a potential antifungal target. FAS prepared from Saccharomyces cerevisiae was employed for bioactivity-guided fractionation of Chlorophora tinctoria,Paspalum conjugatum, Symphonia globulifera, Buchenavia parviflora, and Miconia pilgeriana. Thirteen compounds (1-13), including three new natural products (1, 4, 12), were isolated and their structures identified by spectroscopic interpretation. They represented five chemotypes, namely, isoflavones, flavones, biflavonoids, hydrolyzable tannin-related derivatives, and triterpenoids. 3'-Formylgenistein (1) and ellagic acid 4-O-alpha-l-rhamnopyranoside (9) were the most potent compounds against FAS, with IC(50) values of 2.3 and 7.5 microg/mL, respectively. Furthermore, 43 (14-56) analogues of the five chemotypes from our natural product repository and commercial sources were tested for their FAS inhibitory activity. Structure-activity relationships for some chemotypes were investigated. All these compounds were further evaluated for antifungal activity against Candida albicans and Cryptococcus neoformans. Although there were several antifungal compounds in the set, correlation between the FAS inhibitory activity and antifungal activity could not be defined. SN - 0163-3864 UR - https://www.unboundmedicine.com/medline/citation/12502337/Fatty_acid_synthase_inhibitors_from_plants:_isolation_structure_elucidation_and_SAR_studies_ DB - PRIME DP - Unbound Medicine ER -