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New prenylated metabolites of Deguelia longeracemosa and evaluation of their antimicrobial potential.
Planta Med. 2006 Mar; 72(4):358-63.PM

Abstract

The analysis of root extracts from Deguelia longeracemosa (Benth.) A.M.G. Azevedo yielded fifteen prenylated metabolites. Nine of them are novel, and their molecular structures were determined through spectral analyses (UV, IR, MS and NMR) as being five derivatives of 4-hydroxy-3-phenylcoumarin: 4-hydroxy-3-(4'-hydroxyphenyl)-5-methoxy-6-(8',9'-epoxy-9'-methylbutyl)-2'',2''-dimethylpyrano-(5'',6'':8,7)-coumarin; 4-hydroxy-3-(3',4'-methylenedioxyphenyl)-5-methoxy-6-(3,3-dimethylallyl)-2'',2''-dimethypyrano-(5'',6'':8,7)-coumarin; 4-hydroxy-3-(3'-hydroxy-4'-methoxyphenyl)-5-methoxy-6-(3,3-dimethylallyl)-2'',2''-dimethylpyrano-(5'',6'':8,7)-coumarin; 4-hydroxy-3-(3'-hydroxy-4'-methoxyphenyl)-5-methoxy-2'',2''-dimethylpyrano-(5'',6'':6,7)-coumarin and 4-hydroxy-3-[4'-O-(3,3-dimethylallyl)phenyl]-5-methoxy-2'',2''-dimethylpyrano-(5'',6'':6,7)-coumarin, three derivatives of 1,2-diphenyl-1,2-ethanodione (alpha-oxodeoxybenzoin derivatives): 1-[6-hydroxy-2-methoxy-3-(3,3-dimethylallyl)-2'',2''-dimethylpyrano-(5'',6'':5,4)- ]-2-(4'-hydroxyphenyl)-1,2-ethanedione; 1-[6-hydroxy-2-methoxy-2'',2''-dimethylpyrano-(5'',6'':3,4)]-2-(4'-methoxyphenyl)-1,2-ethanedione; 1-[6-hydroxy-2-methoxy-2'',2''-dimethylpyrano-(5'',6'':3,4)]-2-(3',4'-methylenedioxyphenyl)-1,2-ethanedione and one derivative of deoxybenzoin: 2,4'-dimethoxy-6-hydroxy-2'',2''-dimethylpyrano-(5'',6'':3,4)-deoxybenzoin. The antimicrobial activity of roots extracts and some isolated compounds was screened through bioautography against bacteria and fungi.

Authors+Show Affiliations

Organic Chemistry Department, Chemistry Institute, UNICAMP, Campinas, São Paulo, Brazil. aderbal@iqm.unicamp.brNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

16557478

Citation

Magalhães, Aderbal F., et al. "New Prenylated Metabolites of Deguelia Longeracemosa and Evaluation of Their Antimicrobial Potential." Planta Medica, vol. 72, no. 4, 2006, pp. 358-63.
Magalhães AF, Tozzi AM, Magalhães EG, et al. New prenylated metabolites of Deguelia longeracemosa and evaluation of their antimicrobial potential. Planta Med. 2006;72(4):358-63.
Magalhães, A. F., Tozzi, A. M., Magalhães, E. G., & Souza-Neta, L. C. (2006). New prenylated metabolites of Deguelia longeracemosa and evaluation of their antimicrobial potential. Planta Medica, 72(4), 358-63.
Magalhães AF, et al. New Prenylated Metabolites of Deguelia Longeracemosa and Evaluation of Their Antimicrobial Potential. Planta Med. 2006;72(4):358-63. PubMed PMID: 16557478.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - New prenylated metabolites of Deguelia longeracemosa and evaluation of their antimicrobial potential. AU - Magalhães,Aderbal F, AU - Tozzi,Ana Maria G A, AU - Magalhães,Eva G, AU - Souza-Neta,Lourdes C, PY - 2006/3/25/pubmed PY - 2006/6/8/medline PY - 2006/3/25/entrez SP - 358 EP - 63 JF - Planta medica JO - Planta Med VL - 72 IS - 4 N2 - The analysis of root extracts from Deguelia longeracemosa (Benth.) A.M.G. Azevedo yielded fifteen prenylated metabolites. Nine of them are novel, and their molecular structures were determined through spectral analyses (UV, IR, MS and NMR) as being five derivatives of 4-hydroxy-3-phenylcoumarin: 4-hydroxy-3-(4'-hydroxyphenyl)-5-methoxy-6-(8',9'-epoxy-9'-methylbutyl)-2'',2''-dimethylpyrano-(5'',6'':8,7)-coumarin; 4-hydroxy-3-(3',4'-methylenedioxyphenyl)-5-methoxy-6-(3,3-dimethylallyl)-2'',2''-dimethypyrano-(5'',6'':8,7)-coumarin; 4-hydroxy-3-(3'-hydroxy-4'-methoxyphenyl)-5-methoxy-6-(3,3-dimethylallyl)-2'',2''-dimethylpyrano-(5'',6'':8,7)-coumarin; 4-hydroxy-3-(3'-hydroxy-4'-methoxyphenyl)-5-methoxy-2'',2''-dimethylpyrano-(5'',6'':6,7)-coumarin and 4-hydroxy-3-[4'-O-(3,3-dimethylallyl)phenyl]-5-methoxy-2'',2''-dimethylpyrano-(5'',6'':6,7)-coumarin, three derivatives of 1,2-diphenyl-1,2-ethanodione (alpha-oxodeoxybenzoin derivatives): 1-[6-hydroxy-2-methoxy-3-(3,3-dimethylallyl)-2'',2''-dimethylpyrano-(5'',6'':5,4)- ]-2-(4'-hydroxyphenyl)-1,2-ethanedione; 1-[6-hydroxy-2-methoxy-2'',2''-dimethylpyrano-(5'',6'':3,4)]-2-(4'-methoxyphenyl)-1,2-ethanedione; 1-[6-hydroxy-2-methoxy-2'',2''-dimethylpyrano-(5'',6'':3,4)]-2-(3',4'-methylenedioxyphenyl)-1,2-ethanedione and one derivative of deoxybenzoin: 2,4'-dimethoxy-6-hydroxy-2'',2''-dimethylpyrano-(5'',6'':3,4)-deoxybenzoin. The antimicrobial activity of roots extracts and some isolated compounds was screened through bioautography against bacteria and fungi. SN - 0032-0943 UR - https://www.unboundmedicine.com/medline/citation/16557478/New_prenylated_metabolites_of_Deguelia_longeracemosa_and_evaluation_of_their_antimicrobial_potential_ DB - PRIME DP - Unbound Medicine ER -