Xanthones from Calophyllum teysmannii var. inophylloide (original) (raw)

Xanthones from Calophyllum inophyllum

The roots of Calophyllum inophyllum (Guttiferae), furnished six xanthones which are brasilixanthone (1), 1,3,5-trihydroxy-2-methoxy xanthone (2), caloxanthone A (3), pyranojacareubin (4), caloxanthone B (5) and tovopyrifolin (6), Structural elucidations of these compounds, were achieved through 1D and 2D NMR and MS techniques. In this paper, the isolation and structural elucidation data for these xanthones are reported.

New Xanthones from Calophyllum caledonicum

Journal of Natural Products, 2000

Four new xanthones, caledonixanthones A-D (1-4), were isolated from the trunk bark of Calophyllum caledonicum, in addition to 17 known compounds. The structures of 1-4 were determined by means of spectroscopic analysis and chemical derivatization.

Two New Xanthones from Calophyllum nodusum (Guttiferae)

2011

The air-dried powdered stem bark of Calophyllum nodusum (Guttiferea) collected from Sandakan (Sabah, Malaysia), was extracted sequentially with hexane, chloroform and methanol. The solvents were removed by rotary evaporator to give dark viscous extracts. Detailed and repeated chromatographic separation of the extracts lead to isolation of two new xanthones, identified as nodusuxanthone (1a) and trapezifolixanthone A (2). Other common terpenoids such as betulinic acid, lupeol, stigmasterol and friedelin were also isolated from the extracts and identified. The structures of the compounds were established by detailed spectral analysis and comparison with previously reported data.

Two Antifungal Xanthones from the Heartwood of Calophyllum Symingtonianum

Japan Agricultural Research Quarterly: JARQ, 2012

Antifungal Xanthones from Calophyllum Symingtonianum ly against diarrhea and after childbirth, externally against skin and eye diseases and rheumatism; while the leaves, flowers and seeds are sometimes also used in local medicine 19. The constituents of C. inophyllum are known to show various bioactivities such as anti-HIV 3, 19 , anticancer 7 , antifungal 15 , antibacterial 18 , cytotoxic 5 , piscicidal 12 , and trypanocidal 1 activities. In our previous paper, extracts from the heartwood, sapwood and bark of 11 Malaysian timbers were antifungal assayed against Gloeophyllum trabeum (a brown-rot fungus) and Pycnoporus sanguineus (a white-rot fungus) 9. In the results of the antifungal assay, only the methanol extracts from the heartwood of C. symingtonianum showed very high activity against both fungi. In the present study, therefore, we investigated the compounds contained in the heartwood extracts of C. symingtonia

Antifungal Xanthones from Calophyllum brasiliensis Heartwood

Journal of Chemical Ecology, 2000

The heartwood of the tropical tree Calophyllum brasiliensis is known to be highly resistant to fungi and termites. To determine whether resistance to wood-rotting fungi could be caused by bioactive secondary metabolites, a chemical and biological study was carried out. Hexane, acetone, methanol, and water extracts were prepared. The yield of the extracts ranged from 0.04% (hexane) to 4.81% (acetone). Methanol, acetone, and water extracts (5 mg/ml = 0.5%) inhibited the mycelial growth of the brown rot fungus Postia placenta by 83%, 59%, and 2 1 % , respectively. Chromatographic separation of the acetone and methanol extracts afforded five prenylated xanthones: 6-desoxyjacareubin (I), 1,5-dihydroxy-2-(3,3-dimethylallyl)-3-methoxy-xanthone (II), jacareubin (III) and l,3,5-trihydroxy-2-(3,3dimethylallylj-xanthone (IV) and l,3,5,6-tetrahydroxy-2-(3,3-dimethylallyl)xanthone (V). Xanthones III, IV, and especially V, were the most abundant constituents of both extracts and inhibited at 0.25 mg/ml the mycelial growth of P. placenta. Inhibitory activity ranged from 55.5% (V) to 68.8% (III and IV mixture). Acetylation of xanthones did not induce a sharp change in the extent of fungistasis compared with parent compounds. The above results suggest that C. brasiliensis xanthones actually play a defensive role against wood decay fungi

Xanthones from Calophyllum gracilipes and Their Cytotoxic Activity

Extraction and chromatographic isolation of the hexane, chloroform and methanol extracts of stem bark of Calophyllum gracilipes has led to the isolation of a new xanthone, gracixanthone (1) and the known zeyloxanthanone (2) and trapezifolixanthone (3) together with three common sterols, namely stigmasterol, friedelin and lupeol. The structures of the compounds were elucidated and established by spectroscopic analysis and compared with the spectral data from literature. The cytotoxicity of the compounds was evaluated and zeyloxanthanone (2) exhibited strong activity towards five cell lines with IC 50 values ranging at 8.00-26.00 µΜ.

Calocalabaxanthone, the putative isoprenyl precursor of calabaxanthone from Calophyllum calaba

Phytochemistry, 1982

bark of Calophyllum calaba var. calaba contains a new xanthone, 2,8-di-(3-methylbut-2-enyl)-1,3dihydroxy-7-methoxyxanthone (calocalabaxanthone), the precursor of S-hydroxy-8-methoxy-22-dimethyl-7-(3methylbut-2-enyl)-2H,6H-pyano-(3,2-b)-xanthen-6-one (calabaxanthone). In addition the bark contains calabaxthone and the other constituents isolated earlier from Calophyllum calaba var. worthingtonii.

Thirteen New Xanthone Derivatives from Calophyllum caledonicum (Clusiaceae)

Molecules, 2002

An EtOAc extract of the stem bark of Calophyllum caledonicum (Clusiaceae) yielded thirteen new hydroxylated and/or prenylated xanthone derivatives, namely 5hydroxy-8-methoxyxanthone (1), 3,5-dihydroxy-1,2-dimethoxyxanthone (2), 1,8-dihydroxy-6,7-dimethoxyxanthone (3), 5,7-dihydroxy-2,6-dimethoxyxanthone (4), 6,8-dihydroxy-3,7dimethoxy-xanthone (5), 2,5,6,7,8-pentahydroxyxanthone (6), 1,3,8-trihydroxy-5,7dimethoxyxanthone (7) and according to a previously adopted nomenclature [3], caledonixanthone G-L. (8-13). The structural elucidation of 1-13 were mainly established on the basis of 1D and 2D NMR and HRMS spectroscopic analysis.

A new chromanone acid from the stem bark of Calophyllum teysmannii

Natural Product Research, 2015

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