Xanthones and biphenyls from the stems of Garcinia cylindrocarpa and their cytotoxicity

Sukandar, Edwin Risky; Kaennakam, Sutin; Rassamee, Kitiya; Siripong, Pongpun; Fatmawati, Sri; Ersam, Taslim; Tip‐pyang, Santi

doi:10.1016/j.fitote.2018.08.019

Cited by 21 publications

(26 citation statements)

References 31 publications

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“…Among the group of xanthones, compound 4 was active against four cancer cells (KB, HeLa S3, MCF-7, and Hep G2) with IC 50 values ranging from 5.6 to 7.5 µM. Our earlier studies [11,39] reported that furanoxanthones 7 and 8 also significantly inhibited the growth of KB, HeLa S3, MCF-7, and Hep G2 cancer cells with IC 50 values less than 10 µM, while decreased cytotoxicity was observed for compound 6 with only one hydroxy group in the ring B of the xanthone skeleton. The hydration of the prenyl unit in 8 did not affect cytotoxic properties against the four cancer cells, as shown in schomburgone F [39].…”

Section: Cytotoxic Activity Against Human Cancer Cell Linesmentioning

confidence: 83%

“…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.…”

Section: Introductionmentioning

confidence: 99%

“…Cytotoxic activity of the isolated compounds against five human cancer cell lines. Results are expressed as the means ± SEM of three replicates.b The cytotoxic results based on our previous work[11,39]. c Doxorubicin was used as the positive control.…”

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confidence: 99%

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

et al. 2021

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Garcinia picrorhiza, a woody plant native to Sulawesi and Maluku Islands, Indonesia, has been traditionally used as a wound healing ointment. In our continuous search for bioactive compounds from this plant, 15 phenolic compounds were isolated from its stem bark, including a previously undescribed dihydroisocoumarin, 2′-hydroxyannulatomarin, and two undescribed furanoxanthones, gerontoxanthone C hydrate and 3′-hydroxycalothorexanthone. The structures of the new metabolites were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR and HRESIMS. Gerontoxanthone C hydrate possessed cytotoxicity against four cancer cells (KB, HeLa S3, MCF-7, and Hep G2) with IC50 values ranging from 5.6 to 7.5 µM. Investigation on the anti-inflammatory activities showed that 3′-hydroxycalothorexanthone inhibited NO production in RAW 264.7 and BV-2 cell lines with IC50 values of 16.4 and 13.8 µM, respectively, whereas only (−)-annulatomarin possessed inhibition activity on COX-2 enzyme over 10% at 20 µM. This work describes the presence of 3,4-dihydroisocoumarin structures with a phenyl ring substituent at C-3, which are reported the first time in genus Garcinia. These findings also suggest the potential of furanxanthone derivatives as cytotoxic and anti-inflammatory agents for further pharmacological studies.

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Section: Cytotoxic Activity Against Human Cancer Cell Linesmentioning

confidence: 83%

Section: Introductionmentioning

confidence: 99%

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

et al. 2021

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“…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 ].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2021

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This study aimed to isolate polyprenylated benzophenones from the rootbark of Garcinia celebica and assess their activities in vitro and in silico. The antioxidant activity was evaluated by the DPPH, ABTS, and FRAP methods. The cytotoxicity was evaluated against HeLa, MCF-7, A549, and B16 cancer cell lines. The antiplasmodial activity was performed against the chloroquine-sensitive Plasmodium falciparum strain 3D7. Molecular docking was analyzed on alpha-estrogen receptor (3ERT) and P. falciparum lactate dehydrogenase enzyme (1CET). The prediction of ADMET for the compounds was also studied. For the first time, (-)-cycloxanthochymol, isoxanthochymol, and xanthochymol were isolated from the root bark of Garcinia celebica. The antioxidant and cytotoxicity evaluation showed that all benzophenones exhibited antioxidant activity compared to gallic acid and quercetin as positive controls and also exhibited strong activity against HeLa, MCF-7, A549, and B16 cell lines compared to cisplatin as the positive control. The antiplasmodial evaluation showed that isoxanthochymol exhibited activity against the chloroquine-sensitive P. falciparum strain 3D7. In addition, the in silico molecular docking study supported in vitro activities. The ADMET analysis also indicated the isolated benzophenones are potential oral drug candidates.

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“…Considering the outstanding biological properties of chromene, we have designed a novel synthetic route to a Kobayashi precursor containing a 2,2-dimethyl-2H-chromene moiety, which is further used as a core building block to accomplish the total synthesis of a series of natural xanthones on the gram scale: 6-deoxyisojacareubin, [13] cylindroxanthone D, [14] staudtiixanthone D, [15,16] brasilixanthone A, [17] and cudracuspixanthone O. [18] In particular, the alkoxyl group is introduced to the precursor structure to direct regioselectivity, thereby enabling functional transformations of the product.…”

Section: Introductionmentioning

confidence: 99%

Design of a Functional Chromene‐Type Kobayashi Precursor: Gram‐Scale Total Synthesis of Natural Xanthones by Highly Regioselective Aryne Annulation

Sha

2020

Chemistry A European J

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The 2,2‐dimethyl‐2H‐chromene motif is widely found in many bioactive molecules, and is a privileged structure in the pharmaceutical arena. We have developed a concise and regioselective approach to chromenes and chromanes through an aryne‐based synthetic strategy. A practical, gram‐scale synthetic route to a chromene‐type aryne precursor was explored. Subsequently, cyclization under mild conditions afforded tetracyclic xanthone skeletons with excellent regioselectivity. Our approach provides a concise strategy for the gram‐scale synthesis of chromene‐type xanthones such as 6‐deoxyisojacareubin, cylindroxanthone D, staudtiixanthone D, brasilixanthone A and cudracuspixanthone O.

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Xanthones and biphenyls from the stems of Garcinia cylindrocarpa and their cytotoxicity

Cited by 21 publications

References 31 publications

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

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

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

Design of a Functional Chromene‐Type Kobayashi Precursor: Gram‐Scale Total Synthesis of Natural Xanthones by Highly Regioselective Aryne Annulation

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