Antibacterial activity of prenylated benzopyrans from Peperomia obtusifolia (Piperaceae)

Abstract

Peperomia obtusifolia is a herbaceous perennial plant native to the Americas reported as a traditional medicine to treat snake bites and as a skin cleanser. The bioassay-guided fractionation of crude extracts from aerial parts of P. obtusifolia against a panel of clinically important fungi and bacteria, showed that hexane and dichloromethane extracts demonstrated selective bacterial inhibition, allowing the isolation of the known compounds peperobtusin A (1), and 3,4-dihydro-5hydroxy-2,7-dimethyl-8-(3"-methyl-2"-butenyl)-2-(4'-methyl-1',3'-pentadienyl)-2H-1-benzopyran-6-carboxylic acid (2) from dichloromethane extract. Compound 2 was active against Gram-positive bacteria including community acquired methicillin-resistant Staphylococcus aureus (CA-MRSA) isolates and an Enterococcus faecalis vancomycin-resistant strain, with minimal inhibitory concentration (MIC) values of 4 μg/mL (10.8 μM) and 8 μg/mL (21.6 μM) respectively. The interaction of compound 2 with the bacterial membrane was demonstrated by means of Zeta potential experiments on S. aureus, then confirming the membrane damage by fluorescent microscopy experiments.

Ethnobotany and the Role of Plant Natural Products in Antibiotic Drug Discovery

“…A prenylated benzopyran, 3,4-dihydro-5-hydroxy-2,7dimethyl-8-(3″-methyl-2″-butenyl)-2-(4′-methyl-1′,3′-pentadienyl)-2 H -1-benzopyran 6-carboxylic acid ( 103 ), was isolated by Ruiz Mostacero et al from Peperomia obtusifolia (L.) A. Dietr. (Piperaceae) aerial parts.…”

Vibrational Circular Dichroism for the Assignment of Absolute Configuration of Natural Products in Brazil

“…The reassignment of the absolute configuration of a prenylated chromane isolated from Peperomia obtusifolia (L.) A. Dietr., Piperaceae, an herbaceous perennial plant native to the Americas reported as a traditional medicine to treat snake bites and used as a skin cleanser (Ruiz Mostacero et al 2021), marks the beginning of the use of VCD in Brazil (Batista Jr et al 2010). The absolute configuration of 3,4dihydro-5-hydroxy-2,7-dimethyl-8-(3″-methyl-2″-butenyl)-2-(4′-methyl-1′,3′-pentadienyl)-2H-1-benzopyran-6-carboxylic acid (3) was initially assigned as the incorrect (+)-(S) enantiomer by ECD (Batista Jr et al 2009).…”

“…Antibacterial, antifungal, and antiviral activities have been described for this class of prenylated chromanes from Peperomia species (Gutierrez et al 2016). Compound 3 was active against Gram-positive bacteria including community-acquired methicillin-resistant Staphylococcus aureus isolates and an Enterococcus faecalisvancomycin-resistant strain, with minimal inhibitory concentration (MIC) values of 4 μg/ml (10.8 μM) and 8 μg/ml (21.6 μM), respectively (Ruiz Mostacero et al 2021).…”

Senyawa Bioaktif Kromen Pada Genus Peperomia

“…Peperomia obtusifolia secara tradisional digunakan untuk mengobati luka akibat gigitan serangga dan ular serta penyakit kulit (Toyama et al, 2017). Peperomia obtusifolia memiliki efek farmakologi sebagai antiinflamasi, anti bakteri dan anti jamur (Morandim-Giannetti et al, 2010;Finato et al, 2018;Ruiz Mostacero et al, 2019). Peperomia obtusifolia memiliki senyawa kromen yaitu peperobtusin A, dan 3,4-dihidro-5-hidroksi-2,7-dimetil-8-(3"-metil-2"-butenil)-2-(4"metil-1",3"-pentadienil)-2H-1-benzopiran-6asam karboksilat dari ekstrak diklorometana.…”

“…Peperomia obtusifolia memiliki senyawa kromen yaitu peperobtusin A, dan 3,4-dihidro-5-hidroksi-2,7-dimetil-8-(3"-metil-2"-butenil)-2-(4"metil-1",3"-pentadienil)-2H-1-benzopiran-6asam karboksilat dari ekstrak diklorometana. Senyawa 3,4-dihidro-5-hidroksi-2,7-dimetil-8-(3"-metil-2"-butenil)-2-(4"-metil-1",3"pentadienil)-2H-1-benzopiran-6-asam karboksilat memiliki aktifitas antibakteri terhadap bakteri Gram positif termasuk community acquired methicillin-resistant Staphylococcus aureus (CA-MRSA) dan Enterococcus faecalis vancomycin-resistant, dengan konsentrasi inhibisi minimal adalah 4 µg/mL (10.8 µM) dan 8 µg/mL (21.6 µM) (Kato et al, 2012;Ruiz Mostacero et al, 2019)…”