Two Antifungal Xanthones from the Heartwood of Calophyllum Symingtonianum (original) (raw)
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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
Natural products from stem bark of Calophyllum andersonii
2018
Phytochemical study on the stem bark of Calophyllum andersonii has resulted in the isolation of five xanthones, namely (1) caloxanthone I, (2) pyranojacareubin, (3) macluraxanthone, (4) caloxanthone C, and (5) euxanthone. In this study, the compounds were subjected to various spectroscopic analyses including FT-IR, GC-MS, 1D and 2D NMR for structural elucidations. Furthermore, these xanthones were obtained for the first time from Calophyllum andersonii, a plant never reported before. All four extracts, namely hexane, chloroform, ethyl acetate and methanol extracts of the plant showed moderate inhibitions against Bacillus subtilis
2019
Calophyllum is a pan-tropical genus belongs to the Guttiferae family and locally known in Malaysia as ‘bintangor’. There has been a continual interest to further investigate the phytochemistry of Calophyllum sp because this genus is a rich source of active secondary metabolites which shows anti-HIV, cytotoxicity and antimicrobial properties. In this study, antibacterial and antioxidant activities of barks and leaves of C. ferrugineum and C. incrassatum were investigated. Cold extraction method employing dichloromethane, ethyl acetate and methanol as solvent was performed. All extracts were tested for their total phenolic content and antioxidant activities by DPPH radical scavenging and Ferric Reducing Antioxidant Power (FRAP) assays. The methanol extract from the leaves of C. ferrugineum showed the highest TPC value at 122.08 mg GAE/g and the lowest DPPH SC50 value at 11.80 μg/mL. The methanol extract from the barks of C. ferrugineum was found to have the highest FRAP value among al...
The phytochemical content and antimicrobial activities of Malaysian Calophyllum canum (stem bark)
Pakistan journal of pharmaceutical sciences, 2012
Recently there was huge increase in using of 'herbal products'. These can be defined as plants, parts of plants or extracts from plants that are used for curing disease. However, Calophyllum species is a tropical plant and it has been used in traditional medicine, the limitation in safety and effectiveness information could lead to serious health problems. Providing information for communities by evaluating the phytochemical contents, antioxidant, antimicrobial and cytotoxic activities will improve the therapeutic values. Three main Calophyllum canum fractions (none - high polar) were tested to find out the phenolic, flavonoid, flavonol content, DPPH radical scavenging, reducing power and chelating iron ions. Also were tested against Bacillus cereus, Staphylococcus aureus, Escherichia coli, Psedomonas aeruginosa, Candida albicans, and Cryptococcus neoformans. In addition, cytotoxic activity was assayed against lung cancer A549 cell line. The methanol fraction showed no bioac...
Biological Importance of Phytochemicals from Calophyllum brasiliense Cambess
Annual Research & Review in Biology, 2014
A great diversity of medicinal plants have been traditionally used against gastropathy, infections and inflammatory pathological ailments. C. brasiliense (Clusiaceae) is a large tree native to the tropical forest which thrives from Brazil to Mexico. It is a plant commonly used in traditional medicine against several diseases, infections and other pathological disorders. Phytochemical isolations of heartwood, leaves, stem bark, and seed oil have confirmed the existence of several coumarins, xanthones and triterpenes which have a wide biological activity against bacteria, protozoa, fungus, virus and cancer. C. brasiliense is highlighted as an important resource of calanolides, a dipyranocoumarins that inhibit reverse transcriptase of human immunodeficiency virus type 1 (HIV-1 RT). Despite having wide medicinal importance, the fact that in Mexico it is poorly known is causing a reduction of this species. In this regard, studies on preservation and production of chemical compounds by plant cell culture need to be developed. The aim of this review is to provide the general characteristics of C. brasiliense, the most common traditional uses, and its phytochemical constituents. In particular, we discussed extracts and phytochemical components that have displayed anticancer, antiviral, antimicrobial and antiparasitic activity reported in the current literature. In addition, we intended to inspire new studies on phytotherapy, bioproduction and conservation to be developed.
2018
Calophyllum is a pan-tropical genus belongs to the Guttiferae family and locally known in Malaysia as ‘bintangor’. There has been a continual interest to further investigate the phytochemistry of Calophyllum sp since this genus is a rich source of active secondary metabolites which showed anti-HIV, cytotoxicity and antimicrobial properties. In this study, antibacterial and antioxidant activities of barks and leaves of C. ferrugineum and C. incrassatum were investigated. Cold extraction method employing dichloromethane, ethyl acetate and methanol as solvent was performed. All extracts were tested for their total phenolic content and antioxidant activities by DPPH radical scavenging and Ferric Reducing Antioxidant Power (FRAP) assays. The methanol extract from the leaves of C. ferrugineum showed the highest TPC value at 122.08 mg GAE/g and the lowest DPPH SC50 value at 11.80 µg/mL. The methanol extract from the barks of C. ferrugineum was found to have the highest FRAP value among all...
Chemical compositions and termiticidal activities of the heartwood from Calophyllum inophyllum L
Anais da Academia Brasileira de Ciências, 2015
Wood extractives from heartwood of Callophylum inophyllum (bintangor) were obtained by shaker method and analyzed for their constituents by gas chromatography-mass spectrometry (GC-MS). Ten compounds were identified by ethanol (EtOH) solvents, fourteen by methanol (MeOH) and only nine by petroleum ether (PETETHR). Major compounds were contributed by monoterpenes (75.11%, 53.75%) when extracted with EtOH and PETETHR solvents. The anti-termitic assay of the wood extracts was also investigated against Coptotermes curvignathus. The level of concentration for anti-termite activity may be an indication of the dose application of the wood extracts for new development of termiticide.
Constituents of the Cuban Endemic Species Calophyllum pinetorum
Journal of Natural Products, 2008
A new prenylated xanthone, pinetoxanthone (1), and two new pyranochromanones, pinetoric acid I (2) and pinetoric acid II (3), together with 10 known compounds, namely, the triterpenes friedelin and canophyllol, the xanthone macluraxanthone, the pyranochromanone derivatives calophyllic acid, isocalophyllic acid, calolongic acid, apetalic acid, and isoapetalic acid, and the flavonoids amentoflavone and apigenin, were isolated from the stem bark and leaves of Calophyllum pinetorum, an endemic species in Cuba. The structures of 1-3 were elucidated by spectroscopic methods including 1D and 2D NMR experiments as well as HRESIMS analysis. The genus Calophyllum is comprised of about 130 species, mostly trees, distributed in tropical areas of the world. Previous phytochemical studies of this genus have revealed it to be a rich source of secondary metabolites such as xanthones, 1,2 coumarins, 3,4 chromenes, 5,6 flavonoids, 7 and triterpenoids. 8 Some of these compounds exhibit biological effects such as imunomodulatory, 9 antifungal, 10,11 antimicrobial, 12 antimalarial, 13 and anti-HIV 14,15 activities. Calanolides, a series of pyranocoumarins isolated from Calophyllum species, are representatives of a class of nonnucleoside HIV-1-specific reverse-transcriptase inhibitors under development as AIDS chemotherapeutic agents. 4 As part of an ongoing study on species from the Guttiferae, 16-19 we report herein the first phytochemical investigation on Calophyllum pinetorum Bisse (Guttiferae), a rare endemic tree growing in Pinar del Rio Province of Cuba and used by local populations as a cicatrisant agent. 20 Three new natural products, a xanthone (1) and two pyranochromanone acids (2 and 3), were isolated and characterized from the stem bark and leaves of this plant, respectively, along with 10 compounds of previously known structure.
Phytochemical and antimicrobial studies of Xylopia aethiopica stem bark extracts
2022
The preliminary screening of phytochemical constituents of extracts of Xylopia aethiopica was evaluated. The n-hexane extract revealed the presence of terpenoids, alkaloids, and steroids, while the presence of alkaloids, terpenoids, saponins, steroids, and phenolics was indicated in ethyl acetate extract, and the methanol extract contained tannins, flavonoids, phenolics, terpenoids, saponins, alkaloids, steroids. The medicinal property of the extracts was investigated using in-vitro antimicrobial assays. The hexane extract indicates potent activity against Pseudomonas aeruginosa with MIC of 100mg/ml and ZI of 20 mm. Methanol and ethyl acetate extracts had inhibitory activities against Candida albican with MIC of 100mg/ml while the standard antibiotics have no inhibitory activities against Candida albican 2 suggesting that these extracts contain certain phytochemical that are active against Candida albican. Saponins which are constituents of methanol and ethyl acetate extracts from the phytochemical screening are known to be antifungal, especially against Candida albican. This suggests that the presence of saponins in both ethyl acetate and methanol extracts may be responsible for the inhibitory activities against Candida albican.