Polyprenylated Benzoylphloroglucinols with DNA Polymerase Inhibitory Activity from the Fruits ofGarcinia schomburgkiana

Abstract

Chemical investigation of the fruits of Garcinia schomburgkiana collected in Vietnam led to the isolation of eight new schomburgkianones, A-H (1-8), four known (9-12) polyprenylated benzoylphloroglucinols, and four known biflavonoids. The structures of these compounds were elucidated by spectroscopic and chemical means. The absolute configuration at C-40 of 1 and 2 was determined by (1)H NMR analyses of their MPA esters. The configuration of the bicyclo[3.3.1]nonane core of the polyprenylated benzoylphloroglucinols was assigned by comparison of their experimental ECD spectra with those of related compounds. The polyprenylated benzoylphloroglucinols exhibited inhibitory activities against mammalian DNA polymerases α and λ, with IC50 values ranging from 5.0 to 8.8 μM. Compounds 1, 2, 4, 5, and 9-11 showed cytotoxic effects against HeLa human cervical cancer cells with median lethal dose values lower than 10 μM.

Two new xanthones and cytotoxicity from the bark of Garcinia schomburgkiana

“…In folk medicine in these countries, its leaves, roots, and fruits are used for the treatment of cough, menstrual disturbances, expectorant, laxative and diabetes [ 1 ]. Previous chemical and biological studies on the chemical constituents of G. schomburgkiana showed the presence of xanthones, depsidones, biphenyls, flavonoids, triterpenoids, and phloroglucinols, some of which exhibited antimalarial activity and cytotoxicity [ 2 ], [ 3 ]. Here, we reported two new xanthone derivatives, named schomburgones A ( 1 ) and B ( 2 ), along with six known xanthones ( 3 – 8 ) and two known anthraquinones ( 9 – 10 ) from the bark of this plant.…”

Cytotoxicity Effect of the Pericarp Extracts of Garcinia forbesii King on MCF-7 Breast Cancer and HepG2 Liver Cancer Cell Lines

“…The stem bark of G. cola contains alkaloids, flavonoids and terpenoids 25 . The fruits of G. scomburgkiana contains biflavonoids and flavones 26 . Xanthone flavonoids are contained in the roots of G. ovalifolia 11 .…”

New Compounds and Potential Candidates for Drug Discovery from Medicinal Plants of Vietnam

“…New guttiferones Q-S (74-76) were isolated from the pericarp of G. conchinchinensis, 57) guttiferone I (77) from the stem bark of G. griffithii, 50) and guttiferone T (78) from the bark of G. conchinchinensis. 58) Guttiferone Q may be the biogenetic precur- Fig. 4.…”

“…59) The absolute configuration at C-40 of 78 and 79 was determined by Mosher's modified method. 58,59) The absolute configuration of the bicyclo[3.3.1] nonane core of the schomburgkianones was assigned by comparison of their experimental electronic circular dichroism (ECD) spectra with those of related compounds. 59) New non-isoprenylated benzophenones, benthaphenone (87) and 3′,6-dihydroxy-2,4,4′-trimethoxybenzophenone (88) were isolated from the bark of G. benthami and the heartwood of G. mangostana, 50,60) respectively (Fig.…”

“…57) Guttiferone T (78) showed weak activity, with IC 50 values of 19.88±0.14 and 14.31±0.94 µg/mL, respectively, against HeLa and MCF-7 human cancer cell lines. 58) 3.5. SIRT1 Inhibitory Activity Silent information regulator two ortholog 1 (SIRT1) is a member of the sirtuin deacetylase family of enzymes that removes acetyl groups from lysine residues in histones and other proteins.…”