Picrorhizones A–H, Polyprenylated Benzoylphloroglucinols from the Stem Bark of Garcinia picrorhiza

Abstract

Eight new polyprenylated benzoylphloroglucinol derivatives (1−8) and four known analogues (9−12) were isolated from the stem bark of Garcinia picrorhiza. Their structures were determined by spectroscopic data analysis (1D and 2D NMR and HRESIMS), and the absolute configurations were established by single-crystal X-ray diffraction combined with experimental and calculated ECD data. The new metabolites represent rare examples of benzoylphloroglucinols bearing a cyclobutyl-containing side chain. The isolated compounds were evaluated for their cytotoxic properties against five types of human cancer cells (KB, HeLa S3, MCF-7, Hep G2, and HT-29 cells) and their inhibitory activities against COX-1 and COX-2 enzymes. The cytotoxicity results showed that compound 6 was active against KB, HeLa S3, MCF-7, and Hep G2 cancer cells, with IC 50 values ranging from 5.9 to 9.4 μM. Among the compounds tested for cyclooxygenase inhibition, compound 8 possessed the highest inhibitory effect toward COX-1 (35.2 ± 9.6% inhibition at 20 μM).

Polyprenylated Acylphloroglucinols With Different Carbon Skeletons From the Fruits of Garcinia multiflora

“…Compounds 8–9 are the presence of an enolized C-2 via ether ring closure and C-4 keto form, while compound 10 is the presence of C-2 keto form and an enolized C-4 via ether ring closure. These findings could imply that the position of an enolized 1,3-diketo group in the core structure might affect the molecular conformation and hence the ECD curves ( Le et al, 2016 ; Sukandar et al, 2020 ).…”

Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from Garcinia picrorhiza

“…The crude extract (92.0 g) was partitioned with CH 2 Cl 2 and EtOAc solvents to yield two organic fractions. The CH 2 Cl 2 -soluble fraction (54.1 g) was separated by silica gel column chromatography with hexanes/EtOAc (95:5-0:100) to afford fractions A-R, following the previous procedure [8]. Fraction F (1.1 g) was chromatographed on a Sephadex LH-20 column with CH 2 Cl 2 /MeOH (1:1) to obtain subfractions F1-F4.…”

“…Previously, our group reported eleven polyprenylated benzoylphloroglucinols (PPBPs), including eight derivatives (Picrorhizone A-H) bearing a cyclobutane-containing side chain, with cytotoxic and anti-inflammatory activities. In particular, picrorhizone F was active against four human cancer cells (KB, HeLa S3, MCF-7, and Hep G2) with IC 50 values in the range of 5.9-9.4 µM, while picrorhizone H exhibited the highest COX-1 inhibitory activity (35.2 ± 9.6% inhibition) at 20 µM [8]. Encouraged by structurally diverse bioactive compounds from Garcinia species [8][9][10][11][12], we decided to revisit G. picrorhiza in part of a comprehensive phytochemical and biological investigation.…”

“…In particular, picrorhizone F was active against four human cancer cells (KB, HeLa S3, MCF-7, and Hep G2) with IC 50 values in the range of 5.9-9.4 µM, while picrorhizone H exhibited the highest COX-1 inhibitory activity (35.2 ± 9.6% inhibition) at 20 µM [8]. Encouraged by structurally diverse bioactive compounds from Garcinia species [8][9][10][11][12], we decided to revisit G. picrorhiza in part of a comprehensive phytochemical and biological investigation. Herein, we report the isolation, structural elucidation, and cytotoxic and anti-inflammatory effects of the phenolic compounds from the stem bark of G. picrorhiza.…”

Biological Activity Evaluation and In Silico Studies of Polyprenylated Benzophenones from Garcinia celebica

“…Xanthones vieillardixanthone, isocudraniaxanthone A, 1,3,7-trihydroxyxanthone, cheffouxanthone, smeathxanthone, and benzophenones 2,4,6,3′,4′,6′-hexahydroxybenzophenone and garcinol exhibited impressive antioxidant activity against DPPH [ 6 , 7 , 8 , 9 , 10 , 11 ]. In addition, xanthones 9-hydroxycalabaxanthone, macluraxanthone, garcinoxanthocins A and B, 14-deoxygarcinol garcicowin C, isogarcinol, gaudichaudione H, cantleyanone A, oliganthin I, garcibractatin A, forbesione, isoforbesione, gambogic acid [ 12 , 13 , 14 , 15 , 16 , 17 , 18 ], and polyprenylated benzophenones guttiferone E, guttiferone H, garcinol, and picrorhizone H [ 9 , 19 , 20 ] were shown to exhibit cytotoxicity against cancer cell lines. Mckeanianones A–C, bannaxanthones E and I, pancixanthones A and B, and assiguxanthone A have also been reported to be active against P. falciparum strain TM4 and K1; α-mangostin and β-mangostin have been reported active against P. falciparum strain D6 and W2; while subelliptenone and 12b-hydroxy-des-D-garcigerrin A have also been reported to be active against P. falciparum strain 3D7 [ 21 , 22 , 23 ].…”