Five New Prenylatedp-Hydroxybenzoic Acid Derivatives with Antimicrobial and Molluscicidal Activity fromPiper aduncumLeaves

Abstract

Five new prenylated benzoic acid derivatives, methyl 3-(3,7-dimethyl-2,6-octadienyl)-4-methoxybenzoate (1), 1-(1-methylethyl)-4-methyl-3-cyclohexenyl 3,5-bis(3-methyl-2-butenyl)-4-hydroxybenzoate (2), 1-(1-methylethyl)-4-methyl-3-cyclohexenyl 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoate (3), methyl 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoate (4), and 4-hydroxy-3-(3-methyl-2-butenyl)-5-(3-methyl-2-butenyl)-benzoic acid (5) were isolated from the dried leaves of Piper aduncum L. (Piperaceae). Together with the new metabolites, four known prenylated benzoic acid derivatives, 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoic acid (6), 4-hydroxy-3,5-bis(3-methyl-2-butenyl)-benzoic acid (nervogenic acid, 7), methyl 4-hydroxy-3,5-bis(3-methyl-2-butenyl)-benzoate (8), and methyl 4-hydroxy-3-(3-methyl-2-butenyl)-benzoate (9) as well as, dillapiol (10), myristicin, and the three sesquiterpenes humulene, caryophyllene epoxide, and humulene epoxide were isolated. Compounds 7, 8, and 9 are reported as natural products for the first time. The structures of the isolates were elucidated by spectroscopic methods, mainly 1D-and 2D-NMR spectroscopy. Isolates 4-7, 9, and 10 were molluscicidal while 2, 5-7, and 9 displayed significant antibacterial activities.

Volatile Chemical Constituents of Piper aduncum L and Piper gibbilimbum C. DC (Piperaceae) from Papua New Guinea

“…Phytochemical studies of the compositions of these two species of Piper from PNG have been reported [10,[13][14][15][16][17]. Four new cytotoxic alkenylphenol compounds, designated gibbilimbols A-D were obtained from P. gibbilimbum and their chemical structures established from spectroscopic evidence [10].…”

“…Phytochemical investigation of P. aduncum revealed a new amide, designated as aduncamide [13], three new dihydrochalcones, designated as piperaduncins A -C [14], five new prenylated p-hydroxybenzoic acid derivatives [15], five new unusual monoterpene substituted dihydrochalcones, designated adunctins A -E [16], three new natural products derivatives of chromene and benzoic acids [17] as well as other known chemical compounds.…”

Quantitative HPLC analysis of some marker compounds of hydroalcoholic extracts of Piper aduncum L.

“…Both compounds had been previously isolated from P. aduncum. [9][10][11][12] Dillapiol. 1 (27), 133 (29), 105 (40).…”

“…P. aduncum was registered in the First Edition of Brazilian Pharmacopeia 8 and many studies in the literature describe its phytochemicals and its antimicrobial effects. 9,10 This work describes part of the efforts for the standardization and quality control of hydroalcohol extracts of P. aduncum, based on the HPLC quantification of some marker compounds. This was a colaborative work with Siema Eco Essências da Amazônia, a company that develops an antimicotic product trademarked as Dermodilapiol from aerial parts of Piper aduncum.…”

Chemical Analysis of Essential Oil and Hydrolates of Leaves, Inflorescences and Stems of Piper chimonanthifolium Kunth

“…3 Piper aduncum L., known as fake jaborandi , is reported in folk medicine as diuretic, wound healing and antihemorrhagic, 4 Piper regnellii (Micah) C. DC has antifungal activity 5 and Piper hispidinervum C. DC. is used in the manufacture of fixative for fragrances and as natural insecticides.…”