Four New Isocoumarins from the Mangrove Fungus Alternaria Malorum with Antimicrobial Activities.

Four new isocoumarins, alternariethers A-C (1-3) and alternariester (4) were separated from the fermentation of the fungus Alternaria malorum FL39, purified from Myoporum bontioides. Their structures were ascertained using NMR and HR-ESI-MS spectroscopy. For compound 4, the absolute configuration was solved with the help of ECD calculation and the DP4+ method. Compared with the positive control triadimefon, compound 1 showed more potent antifungal effects on Colletotrichum musae. The antifungal effects of compounds 1, 2, and 3 on Fusarium oxysporum and Fusarium graminearum, of compound 4 on F. oxysporum, were equal to those of triadimefon. Except for compound 4 which was inactive against Escherichia coli with O78 serotype, all compounds showed moderate or weak antibacterial activity against Staphylococcus aureus ATCC 6538 and E. coli with O6 or O78 serotype.

Furanosesquiterpenes and Related Natural Products from Myoporum Species: Isolation and Semisynthesis.

Myoporum species are recognized as toxic plants. Essential oils from the leaves of these species contain furanosesquiterpenes, which comprise the active toxins. In this report, natural products isolation studies of three Myoporum species (M. insulare, M. parvifolium, and M. montanum) afforded two previously unreported furanosesquiterpenes (24 and 25) and three unprecedented γ-lactone-containing analogues (26-28), along with nine previously reported furanosesquiterpenes and five other natural products. Among the 14 furanosesquiterpenes and related compounds isolated in this study, we observed three distinct types of furanosesquiterpene structures isolated from each of these Myoporum species. Semisyntheses of four sesquiterpene natural products were completed from (-)-ngaione over two steps in each case. This included the synthesis of the lactam-containing sesquiterpene myoporumine A.

[Metabolites of endophytic fungus Nigrospora sphaerica S5 from Myoporum bontioides].

The endophytic fungus Nigrospora sphaerica S5 derived from the semi-mangrove plant Myoporum bontioides was fermented. Its metabolites were purified by column chromatography. Nine compounds were obtained and identified as terezine P(1), 3-(1-hydroxyethyl)-4-methyl dihydrofuran-2(3H)-one(2), methylhydroheptelidate(3), hydroheptelidic acid(4), 5, 7-dimethoxy-4, 6-dimethylphthalide(5),(3R,4S)-(-)-4-hydroxymellein(6), pestalopyrone(7), indole-3-formaldehyde(8) and p-hydroxybenzaldehyde(9) by spectroscopic techniques. Terezine P(1) was a new alkaloid belonging to the terezine class with a pyrazine ring. Compounds 2-7 were lactones, of which 3 and 4 belonged to sesquiterpenes. Compounds 8 and 9 were indole alkaloids and phenols, respectively. Compounds 3-6 were purified from Nigrospora sp. for the first time. These compounds showed different degrees of antibacterial activity against Staphylococcus aureus, Escherichia coli of O6 serotype and E. coli of O78 serotype.

Anti-MRSA Sesquiterpenes from the Semi-Mangrove Plant Myoporum bontioides A. Gray.

The striking rise of methicillin-resistant Staphylococcus aureus (MRSA) infections has become a serious threat to public health worldwide. In an effort to search for new anti-MRSA agents from natural products, a bioassay-guided phytochemical study was conducted on the semi-mangrove plant Myoporum bontioides A. Gray, which led to the isolation of two new sesquiterpene alkaloids (1 and 2) and six known furanosesquiterpenes (3⁻8). Their structures were elucidated on the basis of extensive analysis of their 1D, 2D NMR and mass spectroscopic data. These two new alkaloids (1 and 2) displayed potent anti-MRSA activity with MIC value of 6.25 µg/mL. This is the first report of sesquiterpene alkaloids from the plants of Myoporum genus and their anti-MRSA activity.

Structure Elucidation and Botanical Characterization of Diterpenes from a Specific Type of Bee Glue.

Investigation of the single plant source bee glue type originating from Southern Australia resulted in the isolation and structure elucidation of major serrulatane diterpenes, novel 7,8,18-trihydroxyserrulat-14-ene (1), along with its oxidized product, 5,18-epoxyserrulat-14-en-7,8-dione (3) and known (18RS)-5,18-epoxyserrulat-14-en-8,18-diol (2). Exploration into the botanical origin revealed Myoporum insulare R. Br, as the plant source of the bee glue materials. This discovery was made through comparative analysis of the myoporum bee glue samples collected from the beehives, analyses of plant resinous exudate, and resin carried on the hind legs of bees foraging for bee glue.

A Flavone Constituent from Myoporum bontioides Induces M-Phase Cell Cycle Arrest of MCF-7 Breast Cancer Cells.

Myoporum bontioides is a traditional medicinal plant in Asia with various biological activities, including anti-inflammatory and anti-bacterial characteristics. To identify the bioactive constituents from M. bontioides, a newly-identified flavone, 3,4'-dimethoxy-3',5,7-trihydroxyflavone (compound 1), along with eight known compounds, were investigated in human MCF-7 breast cancer, SCC4 oral cancer, and THP-1 monocytic leukemia cells. Among these compounds, compound 1 exhibited the strongest antiproliferative activity with half-maximal inhibitory concentration (IC50) values ranging from 3.3 µM (MCF-7) to 8.6 µM (SCC4). Flow cytometric analysis indicated that compound 1 induced G2/M cell cycle arrest in MCF-7 cells. Mechanistic evidence suggests that the G2/M arrest could be attributable to compound 1's modulatory effects on the phosphorylation and expression of numerous key signaling effectors, including cell division cycle 2 (CDC2), CDC25C, and p53. Notably, compound 1 downregulated the expression of histone deacetylase 2 (HDAC2) and HDAC4, leading to increased histone H3 acetylation and p21 upregulation. Together, these findings suggest the translational potential of compound 1 as a breast cancer treatment.

Chlorine-containing iridoid and iridoid glucoside, and other glucosides from leaves of Myoporum bontioides.

Sixteen compounds were isolated from the MeOH extract of leaves of Myoporum bontioides. The five compounds hitherto unknown, were elucidated to be a chlorine-containing iridoid, named myopochlorin, and an iridoid glucoside, an acylated iridoid glucoside, a linear acetogenin glucoside, and an acyclic monoterpene glucoside, named myobontiosides A-D, respectively, by means of spectroscopic analyses.

Inhibitory activity against plant pathogenic fungi of extracts from Myoporum bontioides A. Gray and indentification of active ingredients.

BACKGROUND: In order to understand the bioactivity of Myoporum bontioides A. Gray against plant pathogens and determine its active ingredients, the inhibitory activities of methanol extracts from M. bontioides against Fusarium oxysporum f. sp. niveum (E. F. Smith) Snyder & Hansen, Pestalotia mangiferae P. Henn., Thielaviopsis paradoxa (De Seynes) v. Hohnel, Colletotrichum musae (Berk. & M. A. Curtis) v. Arx, Alternaria alternata (Fr.) Keissler, Mycosphaerella sentina (Fr.) Schroter and Sphaceloma fawcettii Jenk. were evaluated using a growth rate method, and the active ingredient was isolated by activity-directed isolation and identified by determination and analysis of IR, (1)H NMR, (13)C NMR and mass spectra and correlative physical constants. RESULTS: The results showed that the extracts from stems and leaves of M. bontioides exhibited inhibitory activity against the seven fungi, with > 58% inhibition at 10 g L(-1) after 72 h. The active compound was isolated and identified as (-)-epingaione, and showed inhibitory activity against the above seven fungi. The inhibitory activity against P. mangiferae was the highest, with an EC(50) value of 77 mg L(-1). The EC(50) values against the other six fungi were 147-245 mg L(-1). (-)-Epingaione also inhibited spore germination of F. oxysporum f. sp. niveum, T. paradoxa and S. fawcettii. CONCLUSION: (-)-Epingaione demonstrated broad-spectrum inhibitory activity against plant pathogenic fungi and is promising for exploitation as a fungicide.

[Bioactivity of Myoporum bontioides extracts to Plutella xylostella].

The bioactivity of Myoporum bontioides extracts to Plutella xylostella was studied with IIPC as evaluated index. The results showed that petroleum ether and chloroform extracts had a higher activity than ethyl acetate and alcohol extracts. At 0.01 gDW x ml(-1), the ODR of petroleum ether and chloroform extracts was 84.69% and 79.90%, and 76.47% and 45.70% after treated 1d and 3d, while the IIPC was 0.1565 and 0.2055, respectively. Provided with a higher concentration of 0.05 gDW x ml(-1), the ODR was 88.52% and 72.25%, and 87.33%, 58.37%, while the IIPC was 0.1125 and 0.2620, respectively. From the chloroform extract of Myopdrum Bontioides, three flavonoids, 2, 3-dihydro-5, 7-dihydroxy-2-phenyl-4H-1-Benzopyran-4-one (I), 3, 5, 7-trihydroxy-2-phenyl-4H-1-Benzopyran-4-one (II) and 5, 7-dihydroxy-3-methoxy-2-(4-methoxyphenyl)-4H-1-Benzopyran-4-one (III), were isolated, and their structure were identified based on the analyses of physical and spectrum data. Among these compounds, (II) had a better bioactivity to Plutella xylostella.

[Bioactivity of volatile oils from Myoporum bontioides on Plutella xylostella].

This study showed that the volatile oils from Myoporum bontioides had a significant repellent action on Plutella xylostella. When Plutella xylostella adults entered into the 4-arm selective olfactometer, the preferred times and average staying duration, in the order from more to less, were 3, 1, 4, and 2 arms, which showed a tendency of keeping away from the treatment arms. The males were more sensitive to the volatile oils than the females, when the velocity of flow was 200 ml.min-1. On the first day of the 3rd bioassay, the oviposition deterrent rate and IIPC of the volatile oils on Plutella xylostella adults was 94.48% and 0.0552, respectively. A liquid component of the volatile oils from Myoporum bontioides was isolated, purified, and identified as myoporone.