RESUMO
Extraction of the aerial part of Rinorea yaundensis has led to the isolation of a new monoterpene indole alkaloid (1) along with 10 known compounds (2-11) for the first time from this plant. Their structures were determined by HRMS and NMR spectroscopic analyses as yaundentine hydrochloride (1), Nb-oxide of iso-reserpiline (2), iso-reserpiline (3), iso-carapanaubine (4), lichenxanthone (5), stigmastane-3,6-dione (6), methyl ß-orcinol carboxylate (7), ß-sitosterol-3-O-ß-D-glucoside (8), betulinic acid (9), ursolic acid (10) and benzoic acid (11) while the stereochemistry and absolute configuration of 1 was confirmed by single crystal x-ray crystallography and circular dichroism CD spectrum. Yaundentine hydrochloride (1) exhibited pronounced antioxidant, urease and lipoxygenase inhibitory activities with IC50 values of 35.6 ± 0.23, 20.3 ± 0.58 and 29.6 ± 0.77 µM, respectively. Compound 1 also showed good antimicrobial activity against some Gram positive and negative bacteria.
Assuntos
Alcaloides Indólicos , Monoterpenos , Dicroísmo Circular , Cristalografia por Raios X , Alcaloides Indólicos/química , Estrutura Molecular , Monoterpenos/farmacologiaRESUMO
One new drimane-type sesquiterpenoid, 3 ß-angeloyloxy-7-epifutronolide (1), and one new natural product, polygonumate (2), along with six known drimane-type sesquiterpenes [dendocarbin L (3), (+) winterin (4), (+) fuegin (5), changweikangic acid A (6), futronolide (7), and 7-ketoisodrimenin (8)] were isolated from the whole plant of Polygonum hydropiper Linn. Their structures were determined using spectroscopic techniques. Single-crystal X-ray diffraction study on dendocarbin L (3) and ¹³C-NMR spectroscopic data of (+) winterin (4) are described for the first time. Compound 6 was evaluated for inhibitions of α-chymotrypsin, acetylcholinesterase, and butyrylcholinesterase enzymes.
Assuntos
Extratos Vegetais/química , Polygonum/química , Sesquiterpenos/isolamento & purificação , Acetilcolinesterase/efeitos dos fármacos , Butirilcolinesterase/efeitos dos fármacos , Quimotripsina/antagonistas & inibidores , Cristalografia por Raios X , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Plantas Medicinais/química , Sesquiterpenos Policíclicos , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Difração de Raios XRESUMO
Microbial transformation of 6-dehydroprogesterone (1) with Aspergillus niger yielded three new metabolites, including 6ß-chloro-7α,11α-dihydroxypregna-4-ene-3,20-dione (2), 7α-chloro-6ß,11α-dihydroxypregna-4-ene-3,20-dione (3), and 6α,7α-epoxy-11α-hydroxypregna-4-ene-3,20-dione (4), and two known metabolites; 6α,7α-epoxypregna-4-ene-3,20-dione (5), and 11α-hydroxypregna-4,6-diene-3,20-dione (6). Compounds 2, and 3 contain chlorohydrin moiety at C-6, and C-7, respectively. The biotransformation of 1 with Gibberella fujikuroi yielded a known compound, 11α,17ß-dihydroxyandrosta-4,6-dien-3-one (7).
Assuntos
Aspergillus niger/metabolismo , Gibberella/metabolismo , Progesterona/química , Progesterona/metabolismo , Biotransformação , Estrutura Molecular , EstereoisomerismoRESUMO
Phytochemical studies on the aerial parts of Withania somnifera L. Dunal. (Solanaceae) led to the isolation of a chlorinated steroidal lactone (27-acetoxy-4ß,6α-dihydroxy-5ß-chloro-1-oxowitha-2,24-dienolide), a diepoxy withanolide (5ß,6ß,14α,15α-diepoxy-4ß,27-dihydroxy-1-oxowitha-2,24-dienolide), and withaferin A. Their structures were elucidated by using spectroscopic techniques. All three compounds exhibited a growth inhibition and cytotoxic activity against human lung cancer cell line (NCI-H460), with withaferin A being the most potent (GI(50)=0.18 µg/mL and LC(50)=0.45 µg/mL) among three compounds tested.