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Phytochemical investigation of Cycas circinalis and Cycas revoluta leaflets: moderately active antibacterial biflavonoids.

ABSTRACT: Chemical examination of the methanolic extract of the leaflets of CYCAS CIRCINALIS L. led to the isolation of one new biflavonoid, (2 S, 2'' S)-2,3,2'',3''-tetrahydro-4',4'''-di- O-methylamentoflavone (tetrahydroisoginkgetin; 2), and 15 known compounds, 11 of which are reported for the first time from C. CIRCINALIS. Chromatographic separation of the chloroform extract of C. REVOLUTA Thunb. leaflets afforded 12 compounds, seven of which are reported for the first time from this species. The isolated compounds from both species include 14 biflavonoids, three lignans, three flavan-3-ols, two flavone- C-glucosides, two NOR-isoprenoids, and one flavanone. This is the first report of NMR and CD data of 2,3,2'',3''-tetrahydro-4'- O-methyl- and 2,3-dihydro-4'- O-methyl-amentoflavone ( 6) and ( 7). The effect of O-methylation on the chemical shifts of the neighboring carbons in the (13)C NMR spectra of the dihydro- and tetrahydro-amentoflavone skeletons provides a tool to identify the location of the methoxy groups. Compounds 2, 6, and 18 displayed moderate antibacterial activity against STAPHYLOCOCCUS AUREUS (IC (50) values of 3.9, 9.7, and 8.2 microM, respectively) and methicillin-resistant S. AUREUS (MRSA; IC (50) values of 5.9, 12.5, and 11.5 microM, respectively).

SUBMITTER: Moawad A

PROVIDER: S-EPMC3711132 | biostudies-literature | 2010 May

REPOSITORIES: biostudies-literature

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Phytochemical investigation of Cycas circinalis and Cycas revoluta leaflets: moderately active antibacterial biflavonoids.

Moawad Abeer A Hetta Mona M Zjawiony Jordan K JK Jacob Melissa R MR Hifnawy Mohamed M Marais Jannie P J JP Ferreira Daneel D

Planta medica 20100112 8

Chemical examination of the methanolic extract of the leaflets of CYCAS CIRCINALIS L. led to the isolation of one new biflavonoid, (2 S, 2'' S)-2,3,2'',3''-tetrahydro-4',4'''-di- O-methylamentoflavone (tetrahydroisoginkgetin; 2), and 15 known compounds, 11 of which are reported for the first time from C. CIRCINALIS. Chromatographic separation of the chloroform extract of C. REVOLUTA Thunb. leaflets afforded 12 compounds, seven of which are reported for the first time from this species. The isola ...[more]

PMID: 20072955

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Project description:Abstract A cryptic lineage is a genetically diverged but morphologically unrecognized variant of a known species. Clarifying cryptic lineage evolution is essential for quantifying species diversity. In sympatric cryptic lineage divergence compared with allopatric divergence, the forces of divergent selection and mating patterns override geographical isolation. Introgression, by supplying preadapted or neutral standing genetic variations, can promote sympatric cryptic lineage divergence via selection. However, most studies concentrated on extant species introgression, ignoring the genetic legacy of introgression from extinct or unsampled lineages (“ghost introgression”). Cycads are an ideal plant for studying the influence of ghost introgression because of their common interspecific gene flow and past high extinction rate. Here, we utilized reference‐based ddRADseq to clarify the role of ghost introgression in the evolution of a previously identified sympatric cryptic lineage in Cycas revoluta. After re‐evaluating the evolutionary independency of cryptic lineages, the group‐wise diverged single‐nucleotide polymorphisms among sympatric and allopatric lineages were compared and functionally annotated. Next, we employed an approximate Bayesian computation method for hypothesis testing to clarify the cryptic lineage evolution and ghost introgression effect. SNPs with the genomic signatures of ghost introgression were further annotated. Our results reconfirmed the evolutionary independency of cryptic lineage among C. revoluta and demonstrated that ghost introgression to the noncryptic lineage facilitated their divergence. Gene function related to heat stress and disease resistance implied ecological adaptation of the main extant populations of C. revoluta. Previous population genetics study revealed a sympatric cryptic lineage of Cycas revoluta in Taiwan. By detecting the SNP outliers and annotating its functions of lineages sympatric and allopatric to the cryptic lineage, plus approximate Bayesian computation model selection, this article provided a mechanism of the sympatric cryptic lineage divergence by ghost introgression.

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Dataset Information

Phytochemical investigation of Cycas circinalis and Cycas revoluta leaflets: moderately active antibacterial biflavonoids.

Publications

Phytochemical investigation of Cycas circinalis and Cycas revoluta leaflets: moderately active antibacterial biflavonoids.

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