New Xanthones from the Barks of Cratoxylum sumatranum ssp. neriifolium

Nuangnaowarat, Warraphong; Phupong, Worrapong; Isaka, Masahiko

doi:10.3987/com-10-11994

Cited by 14 publications

(5 citation statements)

References 18 publications

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“…The absolute configuration of 3 was established as 5 R ,7 S ,12 S ,10a S by comparing the experimental ECD of 3 with 2 (Figure ). Hence, 3 was confidently identified as the enantiomer of cochinchinoxanthone. − …”

Section: Results and Discussionmentioning

confidence: 97%

“…Racemic cochinchinoxanthone was initially obtained by chemical transformation . Naturally occurring was isolated from Cratoxylum sumatranum . Ren et al were the first to determine the absolute configuration of cochinchinoxanthone, and they described it as a new compound due to a lack of detailed spectroscopic data .…”

Section: Results and Discussionmentioning

confidence: 99%

“…35 Naturally occurring was isolated from Cratoxylum sumatranum. 36 Ren et al were the first to determine the absolute configuration of cochinchinoxanthone, and they described it as a new compound due to a lack of detailed spectroscopic data. 37 This study was cited by subsequent studies concerning the discovery of cochinchinoxanthone.…”

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: 97%

Section: Results and Discussionmentioning

confidence: 99%

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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“…Using chromatographic methods, 20 known compounds were isolated from dichloromethane and ethyl acetate fractions of the methanol extract of H. hookerianum aerial parts. The structures of these isolates were identified as quercetin ( 1 ), 13 (-)-epicatechin ( 2 ), 13 quercitrin ( 3 ), 13 3-hydroxy-2,4-dimethoxyxanthone ( 4 ), 14 neriifolone A ( 5 ), 15 and 4-hydroxy-26,4′-trimethoxydihydrochalcone ( 6 ) (Supplemental Table S1 and Figure S1), isolariciresinol 9′- O - β -D-glucopyranoside ( 7 ), 16 isocubein ( 8 ), 17 piperitol ( 9 ), 18 sesamin ( 10 ), 18 5,7-dihydroxy-2-(1-methylpropyl) chromone-8- β -D-glucopyranoside ( 11 ), 19 ethyl-4-methoxy- trans -cinnamate ( 12 ), 20 multifidol glucoside ( 13 ), 21 2-(2-methylbutyryl)phloroglucinol 1- O -(6′′- O - β -D-apiofuranosyl)- β -D-glucopyranoside ( 14 ), 22 chipericumin D ( 15 ), 23 uralione D ( 16 ), 24 hypercohin K ( 17 ), 25 uraloidin A ( 18 ), 26 furohyperforin ( 19 ), 27 and piceatannol ( 20 ) 28 by spectroscopic analyses and comparison with literature data (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

“…Twenty known compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were isolated from the aerial parts of H. hookerianum. Ten of these isolated compounds (5-10, 12-14, and 20) are novel for Hypericum species.…”

Section: Discussionmentioning

confidence: 99%

Chemical Constituents and Neuroprotective Activity of Hypericum hookerianum

Hong,

Vu,

Selvaraj

et al. 2023

Natural Product Communications

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Objective/Background The Hypericum hookerianum is widely distributed in Asian countries and prevalently used in traditional herbal medicines for its significant antioxidant, antipyretic, and anticancer properties. To date, very limited reports are available regarding the phytochemical profile, and there are no reports that have studied the neuroprotective potentials of this plant. Experimental Methods The aerial parts of H. hookerianum were collected from the Sapa mountainous district, Lao Cai province of Vietnam. The extracts were prepared using methanol, n-butanol, ethyl acetate, and chloroform and fractionated by normal-phase silica gel column chromatography to isolate compounds. The purity of the isolated compounds was analyzed by liquid chromatography combined with mass spectrometry. The structures were studied using nuclear magnetic resonance spectroscopy. All the isolates were evaluated for their neuroprotective activity against the neurotoxicity induced by glutamate in HT-22 hippocampal cells and 6-hydroxydopamine (6-OHDA) in SH-SY5Y neuroblastoma cells. The fluorescent dye calcein-AM image assay was used to measure the cell viability. Results Bioassay-guided fractionation of the aerial parts of H. hookerianum led to the isolation of 20 previously reported compounds (1-20), including 3 flavonoids (1-3), 2 xanthones (4 and 5), 1 chalcone (6), 4 lignans (7-0), 1 chromone-C-glycoside (11), 1 cinnamic acid derivative (12), 7 phloroglucinols (13-9), and 1 stilbene (20). The structures of the compounds were determined by spectroscopic methods and compared with the reported data. The extracts and isolated compounds showed neuroprotection in both cell models. The compounds 4-hydroxy-2,6,4′-trimethoxydihydrochalcone (6, EC50 = 1.48 µM) and sesamin (10, EC50 = 2.85 µM) exhibited significant neuroprotective effects in HT-22 and SH-SY5Y cells, respectively. Conclusion This is the first report on the neuroprotection of extracts and isolated compounds from H. hookerianum. The results provide information for further studies to develop products for the prevention and treatment of neurological disorders.

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