New steroid produced by Periconia pseudobyssoides K5 isolated from Toona sureni (Meliaceae) and its heme polymerization inhibition activity.

A new ergostane-type steroid named (22E)-3α,6α,9α-ergosta-7,22-diene-3,6,9-triol (1), along with six known steroids 5α,8α-epidioxy-24-ethyl-cholest-6-en-3ß-ol (2), ergosterol-5,8-peroxide (3), cerevisterol (4), isocyathisterol (5), 6ß-hydroxystigmast-4-en-3-one (6), 6ß-hydroxy-4-campesten-3-one (7), were isolated from the fermented unpolished rice media by Periconia pseudobyssoides K5 (Periconiaceae), an endophytic fungus from medicinal plant Toona sureni (Meliaceae). The fermentation takes at 28 ± 2 °C for 30 days. The structure of new steroid (1) was elucidated by extensive spectroscopic measurements (IR, HR-ESI-TOFMS, and 1D and 2D NMR) analyses. The isolated compounds (1-7) were evaluated for heme polymerization inhibition assay (HPIA). The IC50 HPIA value of 1 is 8.24 ± 0.03 mg/ml.

The 2,3-epoxy naphthoquinol produced by endophyte Arthrinium marii M-211.

A novel 2,3-epoxy naphthoquinol, named (6R,7R,8R)-theissenone A (1), possessing an oxatricyclo[5.4.0.03,5]undeca-trien-2-one skeleton, together with two known compounds, (6S,7R,8R)-theissenone (2) and arthrinone (3), were produced by an endophytic fungus, Arthrinium marii M-211, which was isolated from mangrove plants. The structure of 1, including the absolute stereochemistry, was elucidated by analysis of nuclear magnetic resonance (NMR) and mass spectrometry (MS) data and time-dependent density functional theory (TDDFT) calculations of electronic circular dichroism (ECD) spectra. Additionally, the absolute structure of 2 was deduced as a diastereomer of 1 using ECD spectral data analysis. Compounds 1, 2 and 3 exhibited cytotoxic activity against the H4IIE rat hepatoma cells, with IC50 values of 67.5, 46.6 and 13.4 µM, respectively.

Cochlioquinone derivatives produced by coculture of endophytes, Clonostachys rosea and Nectria pseudotrichia.

Three new meroterpenoid derivatives, furanocochlioquinol (1) and furanocochlioquinone (2), as well as nectrianolin D (3), together with two known biogenetically related compounds 4 and 5 were isolated from a mixed culture of two mangrove-derived fungi, Clonostachys rosea B5-2 and Nectria pseudotrichia B69-1. The structures of 1-3 were deduced based on the interpretation of HRMS and NMR data. Compounds 1-5 exhibited cytotoxicity against human promyelocytic leukemia (HL60) cells with IC50 values ranging from 0.47 to 10.16 µM.

Antiproliferation Activity and Apoptotic Mechanism of Soursop (Annona muricata L.) Leaves Extract and Fractions on MCF7 Breast Cancer Cells.

INTRODUCTION: Breast cancer is the second most common cancer in women globally, and the incidence rate has increased annually. Traditional medicine is frequently used as a cancer treatment, and soursop or Annona muricata L (A. muricata) is a traditional medicinal plant that has been widely used as an anticancer treatment and requires more thorough study. METHODS: In this research, we prepared ethanol extract and three solvents, ie, ethyl acetate, n-hexane and water fractions of A. muricata leaves and assessed their antiproliferation and cytotoxic activity on MCF7 breast cancer cells compared with that on CV1 normal kidney cells; observation of cell morphology by stained with mixture of propidium iodide and 4',6-diamidino-2-phenylindole indicated that this treatment induced an ongoing process of apoptotic cell death in MCF7 cells. To clarify the cell death mechanism via apoptosis, we assessed the mRNA expression in the caspase cascade of caspase-9, caspase-3, and PARP-1, and anti-apoptotic, Bcl-2 which mediated cytotoxic activity of extracts and ethyl acetate fractions of A. muricata leaves against MCF7 cells. RESULTS: The ethanol extract, ethyl acetate, n-hexane, and water fractions of A. muricata leaves had IC50 values of 5.3, 2.86, 3.08, and 48.31 µg/mL, respectively, in MCF7 cells but had no activity in CV1 cells. The high cytotoxic activity of A. muricata leaves was reflected by changes in the morphology of cancer cells that appeared after 6 h exposure to A. muricata leaf extract and ethyl acetate fraction; the membrane and nucleus of cells undergoing apoptosis were characterized by the rupture and loss of membranes and nuclei. The mechanism that mediates this cytotoxic activity in MCF7 cells was mediated through a decrease in the expression of Bcl-2 mRNA and an increase in caspase-9 and caspase-3 mRNA expression. CONCLUSION: Therefore, the leaves of the medicinal plant A. muricata contained compounds that on extraction exerted a highly effective activity as an anticancer treatment for breast cancer via induced apoptotic cell death.

ß-Resorcylic Acid Derivatives, with Their Phytotoxic Activities, from the Endophytic Fungus Lasiodiplodia theobromae in the Mangrove Plant Xylocarpus granatum.

Nine new ß-resorcylic acid derivatives, (15S)-de-O-methyllasiodiplodin (1), (13S,15S)-13-hydroxy-de-O-methyllasiodiplodin (2), (14S,15S)-14-hydroxy-de-O-methyllasiodiplodin (3), (13R,14S,15S)-13,14-dihydroxy-de-O-methyllasiodiplodin (4), ethyl (S)-2,4-dihydroxy-6-(8-hydroxynonyl)benzoate (5), ethyl 2,4-dihydroxy-6-(8-hydroxyheptyl)benzoate (6), ethyl 2,4-dihydroxy-6-(4-methoxycarbonylbutyl)benzoate (7), 3-(2-ethoxycarbonyl-3,5-dihydroxyphenyl)propionic acid (8), and isobutyl (S)-2,4-dihydroxy-6-(8-hydroxynonyl)benzoate (9), together with a known ethyl 2,4-dihydroxy-6-(8-oxononyl)benzoate (10) were obtained from Lasiodiplodia theobromae GC-22. The structures of these compounds were elucidated by extensive spectroscopic analyses. Compounds 1, 3, and 6 showed growth inhibitory effects against Digitaria ciliaris. Conversely, treatment with compounds 5, 6, 7, 9, and 10 stimulated elongation activity toward the root of Lactuca sativa. These data expand the repertoire of new ß-resorcylic acid derivatives that may function as lead compounds in the synthesis of new agrochemical agents.

A new antiplasmodial sterol from Indonesian marine sponge, Xestospongia sp.

A new antimalarial sterol, kaimanol (1), along with a known sterol, saringosterol (2) was isolated from the Indonesian Marine sponge, Xestospongia sp. The chemical structure of the new compound was determined on the basis of spectroscopic evidences and by comparison to those related compounds previously reported. Isolated compounds, 1 and 2 were evaluated for their antiplasmodial effect against Plasmodium falciparum 3D7 strains. Compounds 1 and 2 exhibited antiplasmodial activity with IC50 values of 359 and 0.250 nM, respectively.

New metabolites produced by endophyte Clonostachys rosea B5 - 2.

The endophytic fungus, Clonostachys rosea B5-2 was isolated from mangrove plants and subjected to the one strain many compounds (OSMAC) methodology. By this approach, it was found that modification of the culture media enhanced the production of secondary metabolites by C. rosea B5-2. The apple juice supplemented solid rice media led to significant changes in the secondary metabolism of the fungus, C. rosea B5-2, and induced the production of four new compounds, (-)-dihydrovertinolide (2), and clonostach acids A (3), B (4), and C (5) together with the known compound, (-)-vertinolide (1). The new compound (-)-dihydrovertinolide (2) exhibited phytotoxicity against lettuce seedlings at a concentration of 50 mg L-1.