Phenolic Compounds from Baseonema acuminatum Leaves: Isolation and Antimicrobial Activity

Abstract

Three new phenolic compounds, 1-galloyl-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (1), 2-methoxy-5-(1′,2′,3′-trihydroxypropyl)-phenyl-1-O-(6′′-galloyl)-β-D-glucopyranoside (2), and 2-methoxy-5-hydroxymethyl-phenyl-1-O-(6′′-galloyl)-β-D-glucopyranoside (3), together with the known compounds benzyl 6′-O-galloyl-β-D-glucopyranoside (4), 1,6-di-O-galloyl-β-D-glucopyranose (5), myrciaphenone B (6), kaempferol 3-O-(6′′-galloyl)-β-D-glucopyranoside (7), quercetin 3-O-(6′′-galloyl)-β-D-glucopyranoside (8), vomifoliol 9-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside, 2,3-dihydrobenzofuran-2-(4′-hydroxy-3′-methoxyphenyl)-3-α-L-rhamnopyranosyloxymethyl-7-methoxy-5-propanol, and benzyl-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside were isolated from the leaves of Baseonema acuminatum P. Choux (Asclepiadaceae). Their structures were determined by 1D- and 2D-NMR spectroscopy and by ESI-MS analysis. The antimicrobial activity of all compounds was evaluated in vitro against bacteria (Staphylococcus aureus two strains, Bacillus cereus, Bacillus subtilis, Escherichia coli, Salmonella thyphimurium) and three strains of Candida albicans. The new compounds 2 and 3, together with the known compound 4, showed antifungal activity against two clinically isolated Candida albicans strains and against C. albicans ATCC 2091; MIC values were in the range of 25 - 100 μg/mL. Compound 5 was active against the two clinically isolated strains of C. albicans with MICs of 12.5 μg/mL and 25 μg/mL. Compounds 1, 6, 7, and 8 inhibited only one strain of C. albicans at the maximum concentration used. None of the phenolic compounds tested was active against the bacteria studied.

Key words

Baseonema acuminatum - Asclepiadaceae - phenolic compounds - antimicrobial activity

References

• 1 Rabesa Z A. Pharmacopeé de l’Alaotra, Madagascar: Fanantenana.  Antanarivo. 1986;  1 123-34
• 2 Ratsimbason A M, Rasamison V E, Razafindrabeaza T, Rahelinirina L. Test anti-anaphylactique des extraits d’une Asclepiadaceae: Baseonema acuminatum .  Revue Med Pharm Afr. 1997 - 1998;  11 - 12 143-7
• 3 Carrai V, Borgognini-Tarli S M, Huffman M A, Bardi M. Increase in tannin consumption by sifaka (Propithecus verreauxi verreauxi) females during the birth season: a case for self-medication in prosimians?.  Primates. 2003;  44 61-6
• 4 Rasamison V E, Okunade A L, Ratsimbason A M, Rafidinarivo E. Pregnane glycosides from Baseonema acuminatum .  Fitoterapia. 2001;  72 5-11
• 5 Rasamison V E, Cutrone J Q, Okunade A L. Additional pregnane glycosides from Baseonema acuminatum .  Fitoterapia. 2002;  73 442-4
• 6 Braca A, De Tommasi N, Morelli I, Pizza C. New metabolites from Onopordum illyricum .  J Nat Prod. 1999;  62 1371-5
• 7 Lundgren L N, Shen Z, Theander O. The constituents of conifer needles. Dilignol glycosides from Pinus massoniana Lamb.  Acta Chem Scand B. 1985;  39 241-8
• 8 Isaza J H, Ito H, Yoshida T. A flavonol glycoside-lignan ester and accompanying acylated glucosides from Monochaetum multiflorum .  Phytochemistry. 2001;  58 321-7
• 9 Haddock E A, Gupta R K, Al-Shafi S MK, Haslam E. The metabolism of gallic acid and hexahydroxydiphenic acid in plants. Part 1. Introduction. Naturally occurring galloyl ester. J Chem Soc Perkin Trans1 1982: 2515-24
• 10 Yoshikawa M, Shimada H, Nishida N, Li Y, Toguchida I, Yamahara J, Matsuda H. Antidiabetic principles of natural medicines. II. Aldose reductase and α-glucosidase inhibitors from Brazilian natural medicine, the leaves of Myrcia multiflora DC. (Myrtaceae): structures of myrciacitrins I and II and myrciaphenones A and B.  Chem Pharm Bull. 1998;  46 113-9
• 11 Collins F W, Bohm B A, Wilkins C K. Flavonol glycosides gallates from Tellima grandiflora .  Phytochemistry. 1975;  14 1099
• 12 Agrawal P K. Carbon-13 NMR of flavonoids. Elsevier Amsterdam; 1989
• 13 De Tommasi N, Aquino R, De Simone F, Pizza C. Plant metabolites. New sesquiterpene and ionone glycosides from Eriobotrya japonica .  J Nat Prod. 1992;  55 1025-32
• 14 De Tommasi N, Rastrelli L, Cumanda J, Speranza G, Pizza C. Aryl and triterpenic glycosides from Magyricarpus setosus .  Phytochemistry. 1996;  42 163-7
• 15 Braca A, Morelli I, Mendez J, Battinelli L, Braghiroli L, Mazzanti G. Antimicrobial triterpenoids from Licania heteromorpha .  Planta Medica. 2000;  66 768-9
• 16 Otsuka H, Kashima N, Nakamoto K. A neolignan glycoside and acylated iridoid glucosides from stem bark of Alangium platanifolium .  Phytochemistry. 1996;  42 1435-8
• 17 Shen Y -C, Hsieh P -W, Kuo Y -H. Neolignan glucosides from Jasminum urophyllum .  Phytochemistry. 1998;  48 719-23
• 18 Shukla Y N, Srivastava A, Kumar S, Kumar S. Phytotoxic and antimicrobial constituents of Argyreia speciosa and Oenothera biennis .  J Ethnopharmacol. 1999;  67 241-5
• 19 Kubo I, Xiao P, Nihei K, Fujita K, Yamagiwa Y, Kamikawa T. Molecular design of antifungal agents.  J Agr Food Chem. 2002;  50 3992-8