Polyprenylated Xanthones and Benzophenones from the Bark of <i>Garcinia oblongifolia</i>

Shan, Wei‐Guang; Lin, Tian‐Song; Yu, Haining; Cao, Yan; Zhan, Zha‐Jun

doi:10.1002/hlca.201200019

Cited by 30 publications

(17 citation statements)

References 18 publications

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“…The major C 5 unit of the substituents included the commonly found 3-methylbut-2-enyl or isoprenyl group as in isoemericellin and the less frequent 3-hydroxy-3-methylbutyl as in nigrolineaxanthone P and 1,1-dimethylprop-2-enyl as in globuxanthone, respectively [35][36][37]. Prenylated xanthones, caloxanthone O and caloxanthone P, were isolated from Calophyllum inophyllum [38] and polyprenylated xanthones and benzophenones from Garcinia oblongifolia [39].…”

Section: Prenylated and Related Xanthonesmentioning

confidence: 99%

Naturally Occurring Xanthones: Chemistry and Biology

Negi

Bisht

Singh

et al. 2013

Journal of Applied Chemistry

164

120

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Xanthones are one of the biggest classes of compounds in natural product chemistry. A number of xanthones have been isolated from natural sources of higher plants, fungi, ferns, and lichens. They have gradually risen to great importance because of their medicinal properties. This review focuses on the types, isolation, characterization, biological applications, and biosynthesis of naturally occurring xanthones isolated so far. Different physicochemical and instrumental methods such as liquid-solid and liquid-liquid extraction, TLC, flash chromatography, column chromatography, IR,1H NMR and13C NMR spectroscopy, GLC, HPLC, GC, and LCMS have been widely used for isolation and structural elucidation of xanthones. Hepatoprotective, anticarcinogenic, antileprosy, antimalarial, antioxidant, anticholinergic, mutagenicity, radioprotective, immunomodulatory, antibone resorption, antiparasitic, neuraminidase inhibitory, anticomplement, antibacterial, antifungal, algicidal, anti-HIV, cardioprotective, antitumoral, antidiabetes, antihyperlipidemic, antiatherogenic, anti-inflammatory, antiulcer, antidiabetic, hypolipidemic, analgesic, antiasthmatic, antihistaminic, antiamoebic, diuretic, antidiarrheal, larvicidal, and ovicidal activities have been reported for natural occurring xanthones. To a certain extent, this review provides necessary foundation for further research and development of new medicines.

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Section: Prenylated and Related Xanthonesmentioning

confidence: 99%

Naturally Occurring Xanthones: Chemistry and Biology

Negi

Bisht

Singh

et al. 2013

Journal of Applied Chemistry

164

120

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“…It has been used for many years as a folk medicine in China to treat stomatitis, eczema, and burns 1 2 . Previous phytochemical studies of this species led to the discovery of many new compounds, including prenylated benzoylphloroglucinols 3 4 5 6 , xanthones 4 5 , biphenyls 2 , and a new bixanthone derivative, garciobioxanthone 7 , which have been reported to possess a wide range of biological activities, including antitumor 1 8 9 10 , anti-inflammatory 11 , and antienteroviral effects 3 12 .…”

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confidence: 99%

UPLC-PDA-QTOFMS-guided isolation of prenylated xanthones and benzoylphloroglucinols from the leaves of Garcinia oblongifolia and their migration-inhibitory activity

Zhang

Zheng

Ding

et al. 2016

Sci Rep

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A UPLC-PDA-QTOFMS-guided isolation strategy was employed to screen and track potentially new compounds from Garcinia oblongifolia. As a result, two new prenylated xanthones, oblongixanthones D and E (1–2), six new prenylated benzoylphloroglucinol derivatives, oblongifolins V–Z (3–7) and oblongifolin AA (8), as well as a known compound oblongifolin L (9), were isolated from the EtOAc-soluble fraction of an acetone extract of the leaves of Garcinia oblongifolia guided by UPLC-PDA-QTOFMS analysis. The structures of the new compounds were elucidated by 1D- and 2D-NMR spectroscopic analysis and mass spectrometry. Experimental and calculated ECD spectra were used to determine the absolute configurations. The results of wound healing and transwell migration assay showed that oblongixanthones D (1), E (2), and oblongifolin L (9) have the ability to inhibit cancer cell migration in lower cytotoxic concentrations. Western blotting results showed that these compounds exhibited an anti-metastasis effect mainly through downregulating RAF protein levels. In addition, 2 and 9 could inhibit phospho-MEK and phospho-ERK at downstream. Moreover, 1, 2, and 9 could inhibit snail protein level, suggesting that they could regulate the EMT pathway.

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“…The ten known compounds, nujiangexanthones A-B (5-6) [6], nujiangefolins A-B (7-8) [6], guttiferone F (9) [10], jacareubin (10) [11], xanthone V 1 a (11) [12], xanthone V 1 (12) [12], 6-deoxy-jacareubin (13) [13], and cudratricusxanthone E (14) A C C E P T E D M A N U S C R I P T ACCEPTED MANUSCRIPT [14] were identified by comparison of spectroscopic data with reported values.…”

Section: Resultsmentioning

confidence: 99%