Phenolic derivatives from Garcinia multiflora Champion ex Bentham and their chemotaxonomic significance

Yang, Haojie; Tian, Dongsong; Zeng, Yan-Rong; Huang, Liejun; Gu, Wei; Hao, Xiao‐Jiang; Yuan, Chun‐Mao

doi:10.1016/j.bse.2019.103981

Cited by 4 publications

(5 citation statements)

References 28 publications

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“…Yuan group systematically discovered and structurally characterized Garmultines A-C ( 20–22 ) ( Figure 3 ) from Garcinia multiflora Champion ex Bentham ( Tian et al, 2017 ), which contains PPAPs with apoptosis-inducing or cytotoxic properties ( Chien et al, 2008 ; Liu et al, 2010 ; Fan et al, 2015 ; Tian et al, 2016 ; Yang et al, 2020 ) and others ( Wang et al, 2018 ). Compounds 21 and 22 are proved to be isomers.…”

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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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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“…Genus Garcinia is a large genus of the flowering plants which belong to the family Clusiaceae. Plants of this genus with about 450 species are now native to Asia, Australia, America, and Southern Africa [1]. Garcinia species have always contributed valuable properties as traditional medicines to the food chemistry and pharmacology.…”

Section: Introductionmentioning

confidence: 99%

“…Polyisoprenylated benzophenone derived from some Garcinia species, namely garcinol, was recommended for the antioxidant therapeutic targets [4]. Phytochemical investigations of Garcinia plants indicated that xanthones, flavonoids, and benzophenones were major components [1]. Among about 30 Garcinia species distributed in Viet Nam, G. mackeaniana was selected for phytochemical investigation and antioxidant examination [5].…”

Section: Introductionmentioning

confidence: 99%

chemical constituents from methanolic extract of Garcinia mackeaniana leaves and their antioxidant activity

Thu

Van²,

Thanh

et al. 2020

JST

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A phytochemical investigation of the methanolic extract of Garcinia mackeaniana leaves led to the isolation, and determination of five secondary metabolites, including one benzophenone 4,3',4'-trihydroxy-2,6-dimethoxybenzophenone (1), two flavone C-glucosides vitexin (2) and its 2''-O-acetyl derivative (3), one biflavone amentoflavone (4), and one mono-phenol methyl protocatechuate (5). The chemical structures of these compounds were characterized by the NMR-spectroscopic method. These isolated compounds were isolated from G. mackeaniana species for the first time. Benzophenone derivative 1 has shown to be associated with a significant IC50 value of 14.97±0.8 µg/mL in the DPPH-antioxidant assay.

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“…(1.6), and 1,6-dihydroxy-3,7-dimethoxyxanthone (1.7), were obtained from the leaves and twigs of G. multiflora [27]. Another phytochemical investigation led to the isolation of prenylated xanthone α-mangostin (1.8) and its analogues, garcinone D…”

Section: Biosynthesis Ofmentioning

confidence: 99%

“…54 PPB derivative with its benzoyl unit at C-1 of the phloroglucinol skeleton and 1.76 is identified as a type-B PPB with benzoyl ring linked to the C-3. Further cyclization of type-A yields a PPB having an adamantyl skeleton as compound 1.74, while oxidative coupling between hydroxyl group at C-2 and aromatic carbon at C-16 in type-B constructs a γ-pyrone ring as compound 1.77 [27,28]. The isolated compounds were characterized from the leaves and twigs of G.…”

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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Phenolic derivatives from Garcinia multiflora Champion ex Bentham and their chemotaxonomic significance

Cited by 4 publications

References 28 publications

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

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

chemical constituents from methanolic extract of Garcinia mackeaniana leaves and their antioxidant activity

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

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