Geranyl N-Dimethylallylanthranilate, a New Compound from Esenbeckia yaaxhokob

Abstract

Through a bioactivity-guided fractionation from the acetone extract of the leaves from Esenbeckia yaaxhokob geranyl N-dimethylallylanthranilate (1), the first natural N- and O-prenylated anthranilate, was isolated in addition of the known natural products caryophyllene β-oxide, caryolane-5β,9β-diol, spathulenol (2), friedeline, friedelanol, decaprenol, flindersiamine (3) and  β-sitosterol. The antimicrobial activities of the extract, fractions and pure compounds were evaluated against two Gram (+) and four Gram (-) bacteria. Compounds 1 and 2 exhibited moderated antimicrobial activity against Staphyloccocus aureus, while 3 was active against S. aureus and Streptococcus faecalis.

References

• 1 Mata R, Macías M L, Rojas I S, Lotina-Hennsen B, Toscano R A, Anaya A L. Phytotoxic Compounds from Esenbeckia yaxhokob .  Phytochemistry. 1998;  49 441-9
• 2 Hamburguer M O, Cordell G A. A Direct Bioautographic TLC Assay for compounds possessing antibacterial activity.  J Nat Prod. 1987;  50 19-22
• 3 Tanaka Y, Sato H, Kageyu A. Structural characterization of polyprenols by ¹³C NMR spectroscopy: Signal assignments of polyprenol homologs.  Polymer. 1982;  23 1087-91
• 4 Inagaki F, Akira A. Analysis of ¹H and ¹³C nuclear magnetic resonance spectra of spathulenol by two-dimensional methods.  J Chem Soc Perkin Trans. 1985;  II 1773-8
• 5 Iwabuchi H, Kato N, Yoshikura M. Studies on the sesquiterpenoids of Panax ginseng C.A. Meyer IV.  Chem Pharm Bull. 1990;  38 1405-7
• 6 Heymann H, Tezuka Y, Kikuchi T. Supriyatna S. Constituents of Sindora sumatrana Miq I. Isolation and NMR spectral analysis of sesquiterpenes from the dried pods.  Chem Pharm Bull. 1994;  42 138-46
• 7 Vaquette J, Hifnawy M S, Pousset J L, Fournet A, Bouquet A, Cavé A. Alcaloides d’Araliopsis soyauxii. Isolement d’un nouvel alcaloide, l’araliopsine.  Phytochemistry. 1976;  15 743-5
• 8 Ríos J, Recio C, Villar A. Screening methods for natural products with antimicrobial activity: A review of the literature.  J Ethnopharmacol. 1988;  23 127-49
• 9 Bohlmann F, Zdero C h. Neue Furanoeremophylane und Andere Sesquiterpene aus Vertretern der Gattung Euryops .  Phytochemistry. 1978;  17 1135-53
• 10 Gunatilaka A AL, Nanayakkara N PD, Wazeer M IM. ¹³C NMR spectra of some D:A-friedo-oleananes.  Phytochemistry. 1983;  22 991-2
• 11 Patra A, Chaudhuri S K, Acharyya A K. Applications of two-dimensional NMR in spectral assignments of some friedelanes and secofriedelanes.  Magn Reson Chem. 1990;  28 85-9
• 12 Suga T, Kondo S. Alkanes and triterpenoids of Quercus glauca .  Phytochemistry. 1974;  13 522-3