New Biphenyls from<i>Garcinia multiflora</i>

Ji, Bing‐Kun; Li, Yin-Ke; Ye, Yanqing; Jiang, Zhi‐Yong; Yang, Haiying; Du, Gang; Zhou, Min; Pan, Xiao-Xia; Liu, Wenxing; Hu, Qiu‐Fen

doi:10.5935/0103-5053.20150235

Cited by 4 publications

(5 citation statements)

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“…Investigation of the MeOH extract of G. gracilis by chromatographic techniques resulted in the isolation of 35 polyphenols, including nine undescribed structures ( 1 – 3 , 5 – 7 , 10 , 12 , and 17 ) and 26 known compounds: forbesione ( 4 ), isojacareubin ( 8 ), oblongixanthone A ( 9 ), cowadepsidone ( 11 ), multibiphenyl C ( 13 ), schomburgbiphenyl A ( 14 ), doitungbiphenyl A ( 15 ), calophymembranside A ( 16 ), quercetin, naringenin, volkensiflavone, pancibiflavonol, GB 1a, fukugiside, morelloflavone, 1,7-dihydroxy-6-methoxyxanthone, 1,6-dihydroxy-3,7-dimethoxyxanthone, 1,7-dihydroxyxanthone, 1,6-dihydroxy-5-methoxyanthone, 1,6,7-trihydroxyxanthone, 1,3,6,7-tetrahydroxyxanthone, 3,4,5-trihydroxyxanthone, 1,5-dihydroxy-6-methoxyxanthone, 1,2,7-trihydroxyxanthone, isoathyriol, and α-tocospiro A …”

Section: Results and Discussionmentioning

confidence: 99%

“…1 H NMR data indicated four aromatic hydrogens including a singlet signal (δ H 6.29) and three coupled signals as an AMX system (δ H 6.67, d, J = 2.2 Hz; δ H 6.72, d, J = 7.8 Hz; δ H 6.54, dd, J = 7.8 and 2.2 Hz) (Table ). Based on comparisons of NMR, HRESIMS, IR, and UV data, it could be ascertained that 12 possessed a similar structure to that of multibiphenyl C ( 13 ) . Differences in the molecular formulas of the two compounds (C 18 H 20 O 4 for 13 ) and the coupled systems of the B ring (AA′XX′ for 13 ) suggested that 12 was substituted by an additional hydroxyl group at C-3′.…”

Section: Results and Discussionmentioning

confidence: 99%

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Structurally Diverse Cytotoxic Polyphenols from Garcinia gracilis

Ye,

Duan,

Zhou

et al. 2023

J. Nat. Prod.

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Thirty-five diverse polyphenols, belonging to seven structure classes, were isolated from Garcinia gracilis, a medicinal and edible plant sampled from Laos. The structures of nine new compounds, gargarcilones A−I (1−3, 5−7, 10, 12, and 17), were established using spectroscopic, X-ray diffraction, and experimental and calculated ECD methods. Additionally, we revised the stereochemical assignment of cochinchinoxanthone and cochinchinoxanthone C. The compounds were evaluated for antiproliferative activity against five human tumor cell lines (HL-60, A549, SMMC-7721, MDA-MB-231, and SW480). Compounds 1−4, 7, and 8 exhibited cytotoxic activity with IC 50 values of 0.5−8.9 μM. Compound 3 significantly induced apoptosis in SMMC-7721 cells.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

Structurally Diverse Cytotoxic Polyphenols from Garcinia gracilis

Ye,

Duan,

Zhou

et al. 2023

J. Nat. Prod.

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“…It is obvious that all the substances under study have some potential when their therapeutic indices (TIs) or the selective indices (SIs) are compared to the corresponding positive controls. The TI value of the anti-rotavirus positive control Ribavirin is about 20 ( Gao et al, 2016 ), and the SI value of the anti-syncytium positive control azidothymidine is larger than 2.73 ( Chaturonrutsamee et al, 2018 ).…”

Section: Diverse Biphenyls From Clusiaceae and Their Bioactivitymentioning

confidence: 97%

“…Multibiphenyls A-C ( 55–57 ) were three new biphenyls isolated from Garcinia multiflora Champion ex Bentham ( Figure 5 ) ( Gao et al, 2016 ). The distinct structures of these biphenyls are interestingly correlated.…”

Section: Diverse Biphenyls From Clusiaceae and Their Bioactivitymentioning

confidence: 99%

Biphenyls in Clusiaceae: Isolation, structure diversity, synthesis and bioactivity

et al. 2022

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Clusiaceae plants contain a wide range of biologically active metabolites that have gotten a lot of interest in recent decades. The chemical compositions of these plants have been demonstrated to have positive effects on a variety of ailments. The species has been studied for over 70 years, and many bioactive compounds with antioxidant, anti-proliferative, and anti-inflammatory properties have been identified, including xanthones, polycyclic polyprenylated acylphloroglucinols (PPAPs), benzophenones, and biphenyls. Prenylated side chains have been discovered in many of these bioactive substances. To date, there have been numerous studies on PPAPs and xanthones, while no comprehensive review article on biphenyls from Clusiaceae has been published. The unique chemical architectures and growing biological importance of biphenyl compounds have triggered a flurry of research and interest in their isolation, biological evaluation, and mechanistic studies. In particular, the FDA-approved drugs such as sonidegib, tazemetostat, daclatasvir, sacubitril and trifarotene are closely related to their biphenyl-containing moiety. In this review, we summarize the progress and development in the chemistry and biological activity of biphenyls in Clusiaceae, providing an in-depth discussion of their structural diversity and medicinal potential. We also present a preliminary discussion of the biological effects with or without prenyl groups on the biphenyls.

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“…Biological activity studies demonstrated that 1. 43 Garcinia species [53,[56][57][58][59]. Dibenzofuran paucinervin C (1.67) was obtained from the leaves of G. paucinervis [60].…”

Section: Biosynthesis Ofmentioning

confidence: 99%

Chemical constituents from the stems of garcinia cylindrocarpa and the stem bark of garcinia picrorhiza and garcinia tetrandra

Sukandar

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Aiming to discover novel bioactive secondary metabolites from genus Garcinia, we performed phytochemical and biological investigations of three�Garcinia�species collected from Indonesia. A series of chromatographic techniques and spectroscopic data analysis�were used to isolate and characterize�the Garcinia phytochemicals. The cytotoxicity of the isolated compounds was�evaluated against five human cancer cell lines�(HeLa S3, Hep G2, HT-29, MCF-7, and KB) using MTT assay. Four new xanthones, cylindroxanthones DG, and two new biphenyls, cylindrobiphenyls A and B, together with 28 known compounds were successfully isolated from�G. cylindrocarpa stems. From the stem bark of G. tetrandra, nine new xanthones, tetrandraxanthones AI, were identified along with 22 previously described analogues. Eight new polyprenylated benzoylphloroglucinols (PPBPs), picrorhizones AH, and four known analogues were reported from the stem bark of�G. picrorhiza. Among the tested compounds, 9-hydroxycalabaxanthone showed significant cytotoxicity against five human cancer cell lines�with IC50 values in the range of 1.63.4 ?M, while 2-deprenylrheediaxanthone B and picrorhizone F were active against four cancer cells, except HT-29, with IC50 values ranging from 2.2 to 9.4 ?M.

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New Biphenyls fromGarcinia multiflora

Cited by 4 publications

References 0 publications

Structurally Diverse Cytotoxic Polyphenols from Garcinia gracilis

Structurally Diverse Cytotoxic Polyphenols from Garcinia gracilis

Biphenyls in Clusiaceae: Isolation, structure diversity, synthesis and bioactivity

Chemical constituents from the stems of garcinia cylindrocarpa and the stem bark of garcinia picrorhiza and garcinia tetrandra

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