Tetrandraxanthones A–I, Prenylated and Geranylated Xanthones from the Stem Bark of <i>Garcinia tetrandra</i>

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

doi:10.1021/acs.jnatprod.9b00046

Cited by 17 publications

(11 citation statements)

References 31 publications

(38 reference statements)

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“…As of today, thousands of natural xanthone derivatives have been isolated from Amaranthaceae, Anacardiaceae, Annonaceae, Asteraceae, Clusiaceae, Eriocaulaceae, Fabaceae, Filicineae, Gentianaceae, Guttiferae, Hypericaeae, Moraceae, Leguminosae, Loganiaceae, and Polygalaceae families [42][43][44][45][46][47][48][49][50][51][52]. Within 2012-2019, as many as 1225 xanthone derivatives have been isolated from natural sources.…”

Section: Isolation Of Xanthone Derivativesmentioning

confidence: 99%

An Update on the Anticancer Activity of Xanthone Derivatives: A Review

et al. 2021

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The annual number of cancer deaths continues increasing every day; thus, it is urgent to search for and find active, selective, and efficient anticancer drugs as soon as possible. Among the available anticancer drugs, almost all of them contain heterocyclic moiety in their chemical structure. Xanthone is a heterocyclic compound with a dibenzo-γ-pyrone framework and well-known to have “privileged structures” for anticancer activities against several cancer cell lines. The wide anticancer activity of xanthones is produced by caspase activation, RNA binding, DNA cross-linking, as well as P-gp, kinase, aromatase, and topoisomerase inhibition. This anticancer activity depends on the type, number, and position of the attached functional groups in the xanthone skeleton. This review discusses the recent advances in the anticancer activity of xanthone derivatives, both from natural products isolation and synthesis methods, as the anticancer agent through in vitro, in vivo, and clinical assays.

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Section: Isolation Of Xanthone Derivativesmentioning

confidence: 99%

An Update on the Anticancer Activity of Xanthone Derivatives: A Review

et al. 2021

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“…Several polyprenylated benzoylphloroglucinols from the genus Garcinia have been previously reported to have anticancer and anti-inflammatory activities. 13,14,26−29 For example, (−)-garcimultin D, a benzoylphloroglucinol featuring a tricyclo[4.3.1.0 3,7 ]decane core, induces apoptosis in human erythroleukemia cells and G1-phase cell-cycle arrest and inhibits leukemia oncogene expression. 29 Another benzoylphloroglucinol-type compound, garcinol, showed anti-inflammatory effects by inhibiting iNOS and COX-2 expression and NF-κB and JAK/STAT-1 activation in LPS-activated macrophages.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…In the continuing search for novel bioactive substances in Garcinia plants, − the stem bark of G. picrorhiza was investigated, leading to the isolation of known metabolite 9 and new picrorhizones A–H ( 1 – 8 ), along with three known benzoylphloroglucinols ( 10 – 12 ). Herein, the isolation and structural elucidation of the isolated compounds, as well as an in vitro cytotoxic evaluation of five human cancer cell lines using the MTT viability method and anti-inflammatory activity using COX-1 and COX-2 inhibitory assays, are described.…”

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confidence: 99%

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

et al. 2020

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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).

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“…[16] The results compiled here agree with previous findings reported, [2] highlighting the Clusiaceae family (mainly represented by Garcinia) as the most important plant source of prenylated xanthones, while xanthone glycosides are mostly described for the Gentianaceae family (represented by Swertia and Gentianella genera). Simple xanthones are distributed in all most important families (Figure 4), which is to be [135] Swerpunilactone B Swertia hispidicalyx Whole plant no [135] Tetrandraxanthone A Garcinia tetrandra Stem bark no [136] Tetrandraxanthone B Garcinia tetrandra Stem bark no [136] Tetrandraxanthone C Garcinia tetrandra Stem bark no [136] Tetrandraxanthone D Garcinia tetrandra Stem bark no [136] Tetrandraxanthone E Garcinia tetrandra Stem bark yes [136] Tetrandraxanthone F Garcinia tetrandra Stem bark no [136] Tetrandraxanthone G Garcinia tetrandra Stem bark no [136] Tetrandraxanthone H Garcinia tetrandra Stem bark no [136] Tetrandraxanthone I Garcinia tetrandra Stem bark no [136] Venuloxanthone…”

Section: Garcinia Schomburgkianamentioning

confidence: 99%

Xanthones and Cancer: from Natural Sources to Mechanisms of Action

Klein‐Júnior

Campos

Niero

et al. 2020

Chemistry & Biodiversity

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Xanthones are a class of heterocyclic natural products that have been widely studied for their pharmacological potential. In fact, they have been serving as scaffolds for the design of derivatives focusing on drug development. One of the main study targets of xanthones is their anticancer activity. Several compounds belonging to this class have already demonstrated cytotoxic and antitumor effects, making it a promising group for further exploration. This review therefore focuses on recently published studies, emphasizing their natural and synthetic sources and describing the main mechanisms of action responsible for the anticancer effect of promising xanthones.

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Tetrandraxanthones A–I, Prenylated and Geranylated Xanthones from the Stem Bark of Garcinia tetrandra

Cited by 17 publications

References 31 publications

An Update on the Anticancer Activity of Xanthone Derivatives: A Review

An Update on the Anticancer Activity of Xanthone Derivatives: A Review

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

Xanthones and Cancer: from Natural Sources to Mechanisms of Action

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