Epoxyquinophomopsins A and B from endophytic fungus Phomopsis sp. and their activity against tyrosine kinase.

Two new quinone derivatives, epoxyquinophomopsins A (1) and B (2), were purified from the EtOAc extract of endophytic fungus Phomopsis sp isolated from Morus cathayana. The structures of both compounds were determined based on 1D and 2D NMR and mass spectral data, as well as by x-ray diffraction analysis for 1. Compounds 1 and 2 were screened against eight receptor- (RTKs) and eight non-receptor tyrosine kinases (nRTKs). Both compounds showed strong inhibitory properties against Bruton's Tyrosine Kinase (nRTK) with their kinase activity were 19% and 20%, respectively. Only compound 1 that showed strong inhibitory properties against RTKs EGFR and HER-4 with its kinase activity were 16 and 15%, respectively. Thus, both compounds have potential as tyrosine kinase inhibitors.

Flavonoid and stilbene derivatives from Macaranga trichocarpa.

A new farnesylated flavonol (4'-O-methylmacagigantin) and a new geranylated stilbene (macatrichocarpin H), together with eight known phenolic compounds, have been isolated from the leaves of Macaranga trichocarpa. Structures of these compounds were determined based on NMR and mass spectrroscopic data. Cytotoxic properties of the isolated compounds were tested against P-388 cells showing that mactrichocarpin G was the most active compound with IC50 was 3.5µM.

Dihydroflavonol and flavonol derivatives from Macaranga recurvata.

Two new dihydroflavonol derivatives, macarecurvatins A and B, have been isolated from the leaves of Macaranga recurvata (Euphorbiaceaae), along with the known compounds diisoprenylaromadendrin, glyasperin A and broussoflavonol F. The structures of the new compounds were determined on the basis of spectroscopic evidence. Upon cytotoxic evaluation against P-388 cells, macarecurvatin B showed strong activity with an IC50 of 0.83 microM.

Geranylated flavonols from Macaranga rhizinoides.

Two geranylated and methylated flavonol derivatives, macarhizinoidins A (1) and B (2), along with a known phenolic compound methyl 4-isoprenyloxycinnamate (3), have been isolated from the methanol extract of the leaves M. rhizinoides. The structures of these compounds were identified based on their spectroscopic data. On cytotoxic evaluation against murine leukemia P-388 cells, compounds 1-2 showed IC50 values of 11.4 and 13.9 microM, respectively, while compound 3 was inactive.

Phenolic compounds from Cryptocarya konishii: their cytotoxic and tyrosine kinase inhibitory properties.

Two chalcone derivatives, 2'-hydroxychalcone (1) and desmethylinfectocaryone (2), together with five known phenolic compounds infectocaryone (3), cryptocaryone (4), kurzichalcolactone A (5), pinocembrin (6) and trans-N-feruloyltyramine (7), were isolated from the methanol extract of the wood of Cryptocarya konishii. The structures of the new compounds were determined based on the analysis of spectroscopic data, including UV, IR, 1D and 2D NMR, and mass spectra. Evaluation of the cytotoxic and tyrosine kinase inhibitory activities of compounds 1-7 showed that compounds 2-4 strongly inhibited the growth of murine leukemia P-388 cells, whereas compound 4 significantly inhibited the enzyme.

Prenylated flavones from Artocarpus lanceifolius and their cytotoxic properties against P-388 cells.

New prenylated flavones, artoindonesianins Z-4 and Z-5, together with four known prenylated flavones, artonin E, 12-hydroxyartonin E, artobiloxanthone, and cycloartobiloxanthone, have been isolated from the methanol extract of the tree bark of Artocarpus lanceifolius. The structures of these compounds were determined on the basis of spectroscopic data, including UV, IR, 1D and 2D NMR, and mass spectra. The cytotoxic effect of the isolated compounds against murine leukemia P-388 cells is described.

A 2-arylbenzofuran derivative from Hopea mengarawan.

A new 2-arylbenzofuran derivative (diptoindonesin G) (1), along with nine known oligostilbenes, have been isolated and identified from the acetone extract of the tree bark of Hopea mengarawan. The structures of these compounds were determined based on spectroscopic data, including 2D NMR and HREIMS spectra. On cytotoxic evaluation of the isolated compounds against murin leukemia P-388 cells, compound 1 was the strongest in inhibiting the growth of the cells.

Isoprenylated flavanones and dihydrochalcones from Macaranga trichocarpa.

Two isoprenylated flavanones, macatrichocarpins A and B, and two isoprenylated dihydrochalcones, macatrichocarpins C and D, have been isolated and identified from the acetone extract of the leaves of Macaranga trichocarpa. The structures of these compounds were determined based on spectroscopic data, including UV, IR, 1D and 2D NMR spectroscopic and HREIMS data. This is the first report of the presence of dihydrochalcone derivatives in the genus Macaranga.

A modified oligostilbenoid, diptoindonesin C, from Shorea pinanga Scheff.

A new oligostilbenoid, diptoindonesin C, has been isolated from the tree bark of Shorea pinanga Scheff., along with the two known oligostilbenoids gnetin H and hopeaphenol, and a known coumarin scopoletin. The new oligostilbenoid was moderately active against brine shrimps Artemia salina.

Phenolic constituents from the wood of Morus australis with cytotoxic activity.

A new methylated flavonol, 5,7,2',4'-tetrahydroxy-3-methoxyflavone (1), had been isolated from the methanol extract of the wood of Morus australis, along with nine known compounds, kuwanon C (2), morusin (3), morachalcone A (4), oxyresveratrol (5), 4'-(2-methyl-2-buten-4-yl)oxyresveratrol (6), moracins M (7) and C (8), alboctalol (9), and macrourin B (10). The structures of these compounds were determined based on spectral evidence, including UV, IR, NMR, and mass spectra. Cytotoxic properties of compounds 1-10 were evaluated against murine leukemia P-388 cells. The prenylated stilbene 6 and 2-arylbenzofuran 8, and morusin (3) were found to have strong cytotoxic effects with IC50 values of 6.9, 8.7, and 10.1 microM, respectively.

Oligostilbenoids from Shorea gibbosa and their cytotoxic properties against P-388 cells.

A new oligostilbenoid derivative, diptoindonesin F (1), along with five known oligostilbenoids, (-)-ampelopsin A (2), (-)-alpha-viniferin (3), ampelopsin E (4), (-)-vaticanol B (5), and (-)-hemsleyanol D (6), were isolated from the methanol extract of the tree bark of Shorea gibbosa. The structure of the new compound was determined based on the analysis of spectroscopic data, including UV, IR, NMR 1-D and 2-D, and mass spectra. Cytotoxic properties of the isolated oligostilbenoids were evaluated against murine leukemia P-388 cells with the result that compounds 2 and 4 showed the highest cytotoxicity.

Cytotoxic resveratrol oligomers from the tree bark of Dipterocarpus hasseltii.

A new resveratrol tetramer, named diptoindonesin E, was isolated from the acetone extract of the tree bark of Dipterocarpus hasseltii, together with five known resveratrol oligomers (-)-epsilon-viniferin, laevifonol, (-)-alpha-viniferin, vaticanol B, (-)-hopeaphenol, and a coumarin, scopoletin. The structures of these compounds were determined from spectroscopic evidence. Cytotoxicity test of the isolated compounds showed that hopeaphenol strongly inhibited murine leukemia P-388 cells.

Prenylated flavonoids and related compounds of the Indonesian Artocarpus (Moraceae).

Several species of the genus Artocarpus (Moraceae) have been investigated in our laboratories during the last decade. Over 60 phenolic constituents have been discovered and characterized, including 27 new compounds from 13 Indonesian taxa of Artocarpus, namely A. champeden, A. lanceifolius, A. teysmanii, A. scortechinii, A. rotunda, A. maingayi, A. kemando, A. bracteata, A. altilis, A. fretessi, A. gomezianus, A. reticulatus and A. glaucus. The principal and the most pronounced features of these phenolic constituents are the assembly of an isoprenyl substituent at C-3 of a flavone skeleton by closure of an ether bridge or a carbon-carbon linkage with the B ring of the skeleton, which may further rearrange into xanthone to produce various classes of natural products. The structures of the new and unusual natural products are presented. Many of the metabolites also exhibit cytotoxic effect against murine leukemia P388 cells.

Molecular diversity of Artocarpus champeden (Moraceae): a species endemic to Indonesia.

A summary of results obtained in the study of natural products isolated from a Moraceae species Artocarpus champeden is presented. The various classes of 3-prenylflavonoids isolated and the biogenetical correlation between the metabolites are discussed. Some of the flavonoids exhibited strong cytotoxicity against murine leukemia P388 cell lines, suggesting that flavonoids derived from moraceous plants represent a plausible unexplored resource of novel antitumor leads.

Two new cytotoxic isoprenylated flavones, artoindonesianins U and V, from the heartwood of Artocarpus champeden.

Two new isoprenylated flavones, artoindonesianins U (1) and V (2), have been isolated from the heartwood of Artocarpus champeden together with three known isoprenylated flavonoids, 5'-hydroxycudraflavone A, cyclocommunin and artonin B. The structures of the new flavones were elucidated on the basis of spectroscopic evidence. Both compounds 1 and 2 showed strong cytotoxic activity against P-388 cell lines.

Diptoindonesin A, a new C-glucoside of epsilon-viniferin from Shorea seminis (Dipterocarpaceae).

A new C-glucoside of epsilon-viniferin, named diptoindonesin A (1), was isolated from the ethyl acetate extract of the tree bark of Shorea seminis, together with the known stilbene oligomers (-)-ampelopsin A (2), (-)-alpha-viniferin (3), and (-)-hopeaphenol (4). The structure of 1 was determined from spectroscopic evidence.