Morushalunin D, a tri-O-bridged Diels-Alder type adduct from Morus alba var. shalun root cultures and the related precursors.

Three Diels-Alder type adducts (1-3) along with their precursors, including one 2-arylbenzofuran (4) and one stilbene (5), were isolated from the MeOH extract of M. alba var. shalun root cultures. Among them, 1 is a new Diels-Alder type adduct named morushalunin D. The molecular structures of 1-5 were elucidated based on spectroscopic data and comparison with the literatures. Cytotoxic properties of compounds 1-5 were evaluated against murine leukemia P-388 cells. Morushalunin D (1), mulberrofuran T (2), sorocein A (3), moracin M (4), and oxyresveratrol (5) were active, significantly inhibiting the growth of P-388 cells with IC50 values of 0.5, 1.0, 0.6, 2.0, and 3.3 µg/ml, respectively.

Secondary metabolites from Colletotrichum gloeosporioides isolated from Artocarpus heterophyllus and evaluation of their cytotoxic and antibacterial activities.

A new lactone, collectindolide (1), as well as three known compounds, (S)-sydonic acid (2), (S)-hidroxysydonic acid (3), and indole-3-aceticacid (4) were obtained from the liquid media of Colletotrichum gloeosporioides, which was obtained from Artocarpus heterophyllus. The chemical structures of 1-4 were established by spectroscopic analyses, including NMR experiments and by HR-ESI-TOF-MS mass spectroscopy. Compounds 1-4 were evaluated for their cytotoxicity against murine leukaemia P-388 cell lines by MTT assay. Antibacterial activity of compounds 1-4 was also assayed against four bacteria. Phytochemical investigation of the genus Colletotrichum derived from the plant genus Artocarpus is reported for the first time.

New indole alkaloid Morucolletotricin from endophytic fungus Colletotrichum queenslandicum associated with Morus australis Poir. Leaf.

Six compounds were isolated from the ethyl acetate extract of endophytic fungus Colletotrichum queenslandicum derived from Morus australis Poir. leaf. Based on NMR and MS data led to characterised of these compounds including one new indole alkaloid Morucolletotricin (1) along with two other indole alkaloids; tryptopol (2) and indole-3-acetic acid (3), phomopyronol (4), 2-(3-aminophenyl)acetic acid (5) and ergosterol (6). phomopyronol (4) and 2-(3-aminophenyl)acetic acid (5) were first reported from Colletotrichum fungi. The cytotoxic activity of compounds 1-6 was evaluated against murine leukaemia P-388 cells and showed that all compounds were moderate cytotoxic. phomopyronol (4) was the most active among the five other compounds with IC50 = 37.17 µg/mL.

Metabolite Profiles of the Green Beans of Indonesian Arabica Coffee Varieties.

The green beans of 3 Indonesian arabica coffee varieties, namely, ateng, buhun, and sigararutang, were analyzed with 1H NMR-based metabolomics coupled with alpha-glucosidase inhibitory activity assay. These coffees were cultivated in the same geographical conditions. The PLSDA model successfully classified the green coffee beans based on their varieties. To reveal the characteristic metabolites for each coffee variety, S-plot of two-class OPLSDA models was generated and analyzed. Ateng coffee was characterized with trigonelline, sucrose, 5-CQA, and acetic acid. The characteristic metabolites of buhun coffee were citric acid and malic acid. Meanwhile, the most discriminant compound of sigararutang coffee was quinic acid. HCA analysis revealed the lineage relationship of the 3 coffee varieties. Ateng coffee had closer lineage relationship to sigararutang compared to the buhun coffee. Alpha-glucosidase inhibitory activity of the coffee samples did not differ widely. IC50 values of alpha-glucosidase inhibitory activity of ateng, sigararutang, and buhun coffees were 3.01 ± 0.16, 3.14 ± 0.20, and 5.05 ± 0.28 mg/mL, respectively. Although grown in the same geographical conditions, our results revealed that each coffee variety possessed a unique metabolome clarifying the diversity of Indonesian arabica coffees. This study verified that 1H NMR-based metabolomics is an excellence method for discovering the lineage relationship in the samples with different varieties or cultivars.

Secondary metabolites from Diaporthe lithocarpus isolated from Artocarpus heterophyllus.

Fractionation and purification of the ethyl acetate extract of Diaporthe lithocarpus, an endophytic fungus from the leaves of Artocarpus heterophyllus, yielded one new compound, diaporthindoic acid (1), along with seven known compounds (2-8). The new compound was characterized and established by the basis of extensive spectroscopic methods including NMR (1D and 2D) and HRMS. Compound 6 showed the best citotoxicity against murine leukemia P-388 cells with an IC50 value of 0.41 µg/mL. All compounds (1-8) were also tested for their antimicrobial activities. To the best of our knowledge, this is the first chemical evaluation of fungal Diaporthe derived from Artocarpus.

Potential cytotoxic Diels-Alder type adducts from liquid medium of Morus Alba var. shalun root cultures.

A new Diels-Alder type adduct named morushalunin (1), together with three similar compounds, guangsangon E (2), chalcomoracin (3), and kuwanon J (4) were isolated from the EtOAc extract of liquid medium of Morus alba var. shalun root cultures. The structures of the isolated compounds were determined based on spectroscopic data, including 1D, 2D NMR, and MS data. Cytotoxic properties of compounds 1-4 were evaluated against murine leukemia P-388 cells. Morushalunin (1), guangsangon E (2), and chalcomoracin (3) were found to have significant cytotoxicity with IC50 values 0.7, 2.5, and 1.7 µg/mL, respectively, while kuwanon J (4) showed weak cytotoxicity (IC50 = 5.9 µg/mL).

Single Production of Kojic Acid by Aspergillus flavus and the Revision of Flufuran.

Timor Island is very hot and dry due to the high intensity of sunlight experienced throughout the year. The endophytic fungi Aspergillus flavus had been isolated from medicinal plants such as Catharanthus roseus, Annona squamosa and Curcuma xanthorisa. The endophytic fungi A. flavus from each plant was cultivated on solid rice media and then analyzed for its capability for producing kojic acid. The production of kojic acid was analyzed by HPLC; the highest amount of kojic acid was observed from the endophytic fungi A. flavus, isolated from the stem of Catharanthus roseus, followed by A. flavus from Annona squamosa and Curcuma xanthorisa. Simple VLC fractionation of the extract of A. flavus from C.roseus led to the isolation of around 11.1 g of pure kojic acid. The structure of kojic acid (1) was confirmed by NMR and MS spectroscopic data. A comparison of the NMR data with the literature supported the revision of the natural product flufuran to kojic acid. To the best of our knowledge, this is the first report of a strain of endophytic fungi producing only kojic acid without any other toxic metabolites such as alfatoxins. Therefore, this Aspergillus flavus strain can be applied as a potential producer of kojic acid for industrial use.

Anti-angiogenic effect of α-mangostin.

Eleven known prenyl xanthones, isolated from the pericarp of Garcinia mangostana, were tested for their ability to inhibit the phosphorylation of kinase domain receptor (KDR) tyrosine kinase. α-Mangostin was found to inhibit phosphorylation of KDR. α-Mangostin also showed to inhibit phosphorylation of the Y1175 residue of KDR (10 µM). This is the first report that α-mangostin inhibited the phosphorylation of KDR tyrosine kinase and also the Y1175 residue of KDR. α-Mangostin also showed inhibitory effects on proliferation of human umbilical vein endothelial cells (HUVECs) (IC(50) 1.2 µM) and human umbilical artery endothelial cells (IC(50) 2.4 µM), as well as the migration (IC(50) 0.034 µM) and tubule formation (at the concentrations of 0.6 and 1.2 µM) of HUVECs. These results suggest that the inhibition of the phosphorylation of KDR tyrosine kinase is concerned in the anti-angiogenic activity of α-mangostin.

Artoindonesianins N and O, new prenylated stilbene and prenylated arylbenzofuran derivatives from Artocarpus gomezianus.

A new prenylated stilbene, named artoindonesianin N (1) and a new prenylated arylbenzofuran, named artoindonesianin O (2), were isolated from Artocarpus gomezianus Wall. ex Trec. (Moraceae). Their structures were elucidated as 1 and 2 on the basis of spectroscopic evidence. Along with these new compounds, a known phenolic compound was also isolated from this plant and identified as oxyresveratrol (3).

Artoindonesianin P, a new prenylated flavone with cytotoxic activity from Artocarpus lanceifolius.

A new prenylated flavone, named artoindonesianin P (1), was isolated from the tree bark of Artocarpus lanceifolius, together with three known related compounds, artobiloxanthone (2), cycloartobiloxanthone (3) and artonol B (4). The structure of artoindonesianin P 1 was determined on the basis of spectral evidence (MS, 1H and 13C NMR) and by comparison with known related compounds. Compounds 1-4 exhibited significant cytotoxicity against murine P388 leukemia cells.