Calophyllum plants have great pharmaceutical value. Some species of this genus are used in folk medicine to treat and cure diseases, such as toothache, rheumatism, diarrhea, chronic ulcers, skin infections, and wounds. The genus is known to be rich in chromanone derivatives, and some of these compounds have antiviral, antifungal, antibacterial, cytotoxic, and other activities. In order to come to a more complete understanding of chromanone derivatives and gain new bioactive constituents from Calophyllum, chemical structures, pharmacological activities, and biogenesis of chromanone derivatives from Calophyllum have been discussed in this review.
Calophyllum ; chemistry ; metabolism ; Chromones ; chemistry ; metabolism ; Drugs, Chinese Herbal ; chemistry ; metabolism ; Molecular Structure

To study the xanthones from the leaves of Calophyllum inophyllum Linn., several chromatography methods were employed to isolate the constituents. Investigation on the CHCl3 extract led to the isolation of a new xanthone named inophyxanthone A (1) and four known compounds, which were pancixanthone A (2), gerontoxanthone B (3), jacareubin (4) and pyranojacareubin (5). Among them, compound 2 was obtained from this plant firstly, and compound 3 was obtained for the first time from this genus. The structure of inophyxanthone A (1) was identified as 1, 3, 5-trihydroxy-2-(1, 1-dimethylallyl)xanthone by spectral analysis.
Calophyllum ; chemistry ; Molecular Structure ; Plant Leaves ; chemistry ; Plants, Medicinal ; chemistry ; Xanthones ; chemistry ; isolation & purification

This paper reports in vitro cytotoxic, anti-inflammatory and adipocyte diffentiation with adipogenic effects of coumarins inophyllum D (1) and calanone (2), and a chromanone carboxylic acid namely isocordato-oblongic acid (3) isolated from Calophyllum symingtonianum as well as a biflavonoid morelloflavon e (4) isolated from Garcinia prainiana on MCF-7 breast adenocarcinoma RAW 264.7 macrophages and 3T3-L1 preadipocytes cells, respectively. The cytotoxicity study on MCF-7 cell was conducted by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Meanwhile, the study of anti-inflammatory effects in RAW 264.7 macrophages and adipogenic effects on 3T3-L1 pre-adipocytes were conducted through nitrite determination assay and induction of adipocyte differentiation, respectively. In the cytotoxicity study, inophyllum D (1) was the only compounds that exhibited significant cytotoxic effect against MCF-7 cell with IC₅₀ of 84 µg/mL. Further, all by inhibiting the compounds have shown anti-inflammatory effects in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages of nitrite concentration with production. In addition, the compounds also exhibited adipogenic effects on 3T3-L1 pre-adipocytes by stimulating lipid formation. Thus, this study may provide significant input in discovery of the potential effects cytotoxic, anti-inflammatory and adipogenic agents.
Adenocarcinoma ; Adipocytes ; Breast ; Calophyllum ; Cell Line* ; Coumarins ; Garcinia ; In Vitro Techniques ; Macrophages ; MCF-7 Cells

AIMTo investigate the effects of fungal elicitors on inophyllums production in suspension cultured cell of Calophyllum inophyllum Linn.

METHODSThe pathogen of leaf spot disease of C. inophyllum L. was isolated and prepared as fungal elicitor. The fungal elicitor was added to the medium with different concentrations and culture period. Their effects on biomass and inophyllums content of the suspension of cultured cells were studied.

RESULTSThe optimum effects of S-I fungal elicitor concentrations on inophyllums content was 60 mg GE x L(-1). Adding the fungi elicitor into the cell suspension culture system at stationary phase (being cultured for 18 days) resulted in a highest inophyllum content of 59.174 mg x L(-1) at the 3rd day with 27% higher than control. Fungal elicitor treatment promoted the inophyllums accumulation in medium.

CONCLUSIONAdding the Stagonospora curtisii (Berk.) Sacc. to the medium was effective approaches to enhance inophyllums yield in the suspension of C. inophyllum L culture cell.

Calophyllum ; cytology ; metabolism ; Cell Division ; Cells, Cultured ; Coumarins ; metabolism ; Culture Media ; Mitosporic Fungi ; physiology

Callophylum symingtonianum (Guttiferae), an evergreen broad-leaved tree that usually grows in hill forests, can be found distributed in the Malay Peninsula. The barks, leaves, flowers and seeds is often used medicinally to treat diarrhea and rheumatism. In the present study, we isolated two inophyllum type coumarins, 12-O-ethylinophyllum D (1) and iso-soulattrolide (2) from the stembarks of C. symingtonianum together with their antibacterial activity. The compounds were isolated by chromatographic methods on a silica gel. The structures were established by spectroscopic methods including UV, IR, (1D and 2D) NMR and mass spectrometry as well as by comparison with several literature sources. The antibacterial activity of those compounds was tested using a disc-diffusion assay against Staphylococcus aureus, Bacillus cereus, Escherichia coli and Pseudomonas aeruginosa. Both compound exhibited mild inhibition against P. aeruginosa with both 111 µg/ml MIC value. Compound 2 also inhibits S. aureus with 25 µg/ml MIC value.
Bacillus cereus ; Calophyllum ; Coumarins ; Diarrhea ; Escherichia coli ; Flowers ; Forests ; Malaysia ; Mass Spectrometry ; Pseudomonas aeruginosa ; Rheumatic Diseases ; Silica Gel ; Staphylococcus aureus ; Trees

OBJECTIVETo study the chemical constituents from the stems and leaves of Calophyllum inophyllum.

METHODThe compounds were isolated by column chromatography on silica gel, Sephadex LH-20 and preparative TLC. Their structures were elucidated by chemical methods and NMR, MS spectroscopic data.

RESULTNine compounds were identified as 2-hydroxyxanthone (1), 4-hydroxyxanthone (2), 1, 5-dihydroxyxanthone (3), 1, 7-dihydroxyxanthone (4), 1, 3, 5-trihydroxy-2-methoxyxanthone (5), 6-deoxyjacareubin (6), amentoflavone (7), kaempferol-3-O-alpha-L-rhamnoside (8) and quercetin-3-O-alpha-L-rhamnoside (9).

CONCLUSIONCompounds 8 and 9 were isolated from the genus Calophyllum and compounds 1, 2, 4-6 were isolated from this plant for the first time.

Calophyllum ; chemistry ; Chromatography ; methods ; Flavonoids ; analysis ; chemistry ; isolation & purification ; Glycosides ; analysis ; chemistry ; isolation & purification ; Kaempferols ; analysis ; chemistry ; isolation & purification ; Magnetic Resonance Spectroscopy ; methods ; Mass Spectrometry ; methods ; Plant Leaves ; chemistry ; Plant Stems ; chemistry ; Plants, Medicinal ; chemistry ; Pyrans ; analysis ; chemistry ; isolation & purification ; Quercetin ; analogs & derivatives ; analysis ; chemistry ; isolation & purification ; Xanthenes ; analysis ; chemistry ; isolation & purification