Dataset Information

Anti-cancer activity of new benzyl isoquinoline alkaloid from Saudi plant Annona squamosa.

ABSTRACT: Two alkaloids, belonging to benzylisoquinoline alkaloids, were isolated from Annona squamosa. One of these alkaloids, 6, 7-dimethoxy-1-(?-hydroxy-4-methoxybenzyl)-2-methyl-1, 2, 3, 4-tetrahydroisoquinoline, was isolated for the first time from natural sources, while, the alkaloid, Coclaurine was known in Annona squamosa L. Moreover, the isolated alkaloids tested for the anti-cancer activities on various cell lines (HepG-2, MCF-7, and HCT-116).

SUBMITTER: Al-Ghazzawi AM

PROVIDER: S-EPMC6661725 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Anti-cancer activity of new benzyl isoquinoline alkaloid from Saudi plant Annona squamosa.

Al-Ghazzawi Adel M AM

BMC chemistry 20190204 1

Two alkaloids, belonging to benzylisoquinoline alkaloids, were isolated from Annona squamosa. One of these alkaloids, 6, 7-dimethoxy-1-(α-hydroxy-4-methoxybenzyl)-2-methyl-1, 2, 3, 4-tetrahydroisoquinoline, was isolated for the first time from natural sources, while, the alkaloid, Coclaurine was known in Annona squamosa L. Moreover, the isolated alkaloids tested for the anti-cancer activities on various cell lines (HepG-2, MCF-7, and HCT-116). ...[more]

PMID: 31384762

Similar Datasets

Project description:Ipecac alkaloids produced in the medicinal plant Psychotria ipecacuanha such as emetine and cephaeline possess a monoterpenoid-tetrahydroisoquinoline skeleton, which is formed by condensation of dopamine and secologanin. Deglucosylation of one of the condensed products N-deacetylisoipecoside (1 alpha(S)-epimer) is considered to be a part of the reactions for emetine biosynthesis, whereas its 1 beta(R)-epimer N-deacetylipecoside is converted to ipecoside in P. ipecacuanha. Here, we isolated a cDNA clone Ipeglu1 encoding Ipecac alkaloid beta-D-glucosidase from P. ipecacuanha. The deduced protein showed 54 and 48% identities to raucaffricine beta-glucosidase and strictosidine beta-glucosidase, respectively. Recombinant IpeGlu1 enzyme preferentially hydrolyzed glucosidic Ipecac alkaloids except for their lactams, but showed poor or no activity toward other substrates, including terpenoid-indole alkaloid glucosides. Liquid chromatography-tandem mass spectrometry analysis of deglucosylated products of N-deacetylisoipecoside revealed spontaneous transitions of the highly reactive aglycons, one of which was supposed to be the intermediate for emetine biosynthesis. IpeGlu1 activity was extremely poor toward 7-O-methyl and 6,7-O,O-dimethyl derivatives. However, 6-O-methyl derivatives were hydrolyzed as efficiently as non-methylated substrates, suggesting the possibility of 6-O-methylation prior to deglucosylation by IpeGlu1. In contrast to the strictosidine beta-glucosidase that stereospecifically hydrolyzes 3 alpha(S)-epimer in terpenoid-indole alkaloid biosynthesis, IpeGlu1 lacked stereospecificity for its substrates where 1 beta(R)-epimers were preferred to 1 alpha(S)-epimers, although ipecoside (1 beta(R)) is a major alkaloidal glucoside in P. ipecacuanha, suggesting the compartmentalization of IpeGlu1 from ipecoside. These facts have significant implications for distinct physiological roles of 1 alpha(S)- and 1 beta(R)-epimers and for the involvement of IpeGlu1 in the metabolic fate of both of them.

Dataset Information

Anti-cancer activity of new benzyl isoquinoline alkaloid from Saudi plant Annona squamosa.

Publications

Anti-cancer activity of new benzyl isoquinoline alkaloid from Saudi plant <i>Annona squamosa</i>.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets