Anti-inflammatory diterpenoids from an endophytic fungus Phomopsis sp. S12

Three new pimarane-type diterpenoids, along with two known compounds, were isolated from an endophytic fungus Phomopsis sp. S12. Their structures were determined by comprehensive analyses of HRESIMS, NMR, CD, as well as single-crystal X-ray diffractions. Compound 3 exhibited anti-inflammatory activity against the production of IL-1β and IL-6 induced by lipopolysaccharide (LPS) in macrophages. A putative biosynthetic pathway for compounds 1–5 were also proposed.     

Three new oblongolides from Phomopsis sp. XZ-01, an endophytic fungus from Camptotheca acuminate

Four new metabolites, including three new oblongolides named C1, P1, and X1 (1-3) and 6-hydroxyphomodiol (10), along with eight known compounds--oblongolides B (4), C (5), D (6), O (7), P (8) and U (9), (3R,4aR,5S,6R)-6-hydroxy-5-methylramulosin (11), and (3R)-5-methylmellein (12)--were isolated from the endophytic fungal strain Phomopsis sp. XZ-01 of Camptotheca acuminate. Their structures were elucidated by spectroscopic analyses, including 1H- and 13C-NMR, 2D NMR (HSQC, HMBC, 1H-1H COSY and NOESY) and HR-FT-MS. Cytotoxic activities of these compounds were evaluated. Some of them showed weak selective activities.     

Polyketides and nitrogenous metabolites from the endophytic fungus Phomopsis sp. D15a2a

Three new polyketides, phomopones A−C (1–3), one new cyclic tetrapeptide, 18-hydroxydihydrotentoxin (4), and a new amide, 6-hydroxyenamidin (5) together with a known derivative, enamindin (6) were obtained from the endophytic fungus Phomopsis sp. D15a2a isolated from the plant Alternanthera bettzickiana. The structures of the new compounds were elucidated by 1D, 2D NMR and HRMS data. The absolute configurations of the isolated metabolites were determined either by X-ray crystallography, Marfey’s method or by converting the compounds to Mosher esters.     

Phomosines H-J, novel highly substituted biaryl ethers, isolated from the endophytic fungus Phomopsis sp. from Ligustrum vulgare

From the endophytic fungus Phomosis sp., four known phomosines A-D (1-4) and three new phomosines H-J (5-7) have been isolated. The structures of the new compounds were determined on the basis of their spectroscopic data analysis (1H, 13C, 1H-1H COSY, HMQC, and HMBC NMR, as well as mass spectrometry). The structures of phomosine H (5) and J (7) were also confirmed by semisynthesis from phomosine A (1). The remaining four known compounds [phomosines A-D (1-4)] were identified by comparing their spectroscopic data with those reported in the literature. The four known metabolites were biologically active. Of the novel metabolites, only 6 was antifungal and antibacterial.     

A new phenol compound from endophytic Phomopsis sp. DC01

The strain DC01 was isolated from the branch tissue of Daphniphyllum longeracemosum and determined to be a member of Phomopsis according to the ITS sequence analysis. The extracts from the PDA solid fermentation media of Phomopsis sp. DC01 were purified and three compounds including one new phenol compound were obtained. The new compound was identified to be (E?)-7-(2-hydroxy-4-(hydroxymethyl)phenyl)-2-methyloct-6-enoic acid (1) based on 1-D NMR, 2-D NMR and HR-ESI data.     

Antiparasitic and anticancer constituents of the endophytic fungus Aspergillus sp. strain F1544

With the combined goal of finding the best anti-parasitic and anti-cancer activities as well as isolating the bioactive agents and studying their structures and biological properties, we proceeded to perform a small-scale cultivation of Aspergillus sp. strain F1544 using Potato Dextrose, Malt Extract, Czapek Dox and Eight Vegetables media. From the more promising extracts (obtaining using potato dextrose and czapek dox media in large scale) of this fungus, we isolated the five compounds: pseurotin A (1), 14-norpseurotin A (2), FD-838 (3), and pseurotin D (4), and fumoquinone B (5). All compounds showed good antileishmanial and moderate anticancer activities.     

Chemical constituents of the new endophytic fungus Mycosphaerella sp. nov. and their anti-parasitic activity

Chemical investigation of a new endophytic fungus, Mycosphaerella sp. nov. strain F2140, associated with the foliage of the plant Psychotria horizontalis (Rubiaceae) in Panama, resulted in the isolation of cercosporin (1) and a new cercosporin analog (3) as the major components. The structures of minor compounds in the extract were elucidated by detailed spectroscopic analysis as 2-(2-butyl)-6-ethyl-3-hydroxy-6-methylcyclohex-2-ene-1,5-dione (4), 3-(2-butyl)-6-ethyl-5-hydroxy-2-methoxy-6-methyl-cyclohex-2-enone (5), and an isomer of 5 (6). To study the influence of the hydroxy groups on the anti-parasitic activity of cercosporin, compound 1 was acetylated to obtain derivative 2. The isolated compounds 1- 6 were tested in vitro to determine their anti-parasitic activity against the causal agents of malaria (Plasmodium falciparum), leishmaniasis (Leishmania donovani), and Chagas disease (Trypanosoma cruzi). Cytotoxicity and potential anticancer activity of these compounds were evaluated using mammalian Vero cells and MCF7 cancer cell lines, respectively. Compounds 1 and 2 displayed high potency against L. donovani (IC50 0.46 and 0.64 microM), T. cruzi (IC50 1.08 and 0.78 microM), P. falciparum (IC50 1.03 and 2.99 microM), and MCF7 cancer cell lines (IC50 4.68 and 3.56 microM). Compounds 3-6 were not active in these assays at a concentration of 10 microg/mL.     

Pimarane diterpenes from the endophytic fungus Eutypella sp. BCC 13199

Two new pimarane-type diterpenes, eutypellones A (1) and B (2), were isolated from the endophytic fungus Eutypella sp. BCC 13199. Cytotoxic activities of the pimaranes 1-5, isolated from this fungus, were evaluated.     

Eremophilane sesquiterpenes from the endophytic fungus Xylaria sp. GDG-102

A new eremophilane sesquiterpene, xylareremophil (1), together with five known eremophilanes, 1α,10α-epoxy-3α-hydroxyeremophil-7(11)-en-12,8β-olide (2), 1,10α,13-trihydroxyeremophil-7(11)-en-12,8-olide (3), 1α,10α-epoxy-13-hydroxyeremophil-7(11)-en-12,8β-olide (4), mairetolides B (5) and G (6) were isolated from the endophytic fungus Xylaria sp. GDG-102 cultured from Sophora tonkinensis. Their structures were elucidated on the basis of spectroscopic data analysis. The absolute configurations of 1 was determined by comparing computed electronic circular dichroism (ECD) and optical rotation (OR) with experimental results. Compounds 1, 5 and 6 showed antibacterial activities against Proteus vulgaris, Micrococcus luteus, Micrococcus lysodeikticus and Bacillus subtilis with MIC values of 25–100 μg/mL.     

Xyloketal H from the mangrove endophytic fungus Xylaria sp. 2508

(3R*,3aR*,9aR*)-3,9a-Dimethyl-2,3,3a,9a-tetrahydro-4H-furo[2,3-b]chromene-5,7-diol (xyloketal H), a representative of a new family of xyloketals, was isolated from the marine-derived mangrove fungus Xylaria sp. 2508. Its structure was elucidated by spectroscopic data and single-crystal X-ray diffraction analysis. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1051–1052, June, 2006.     

Lasiodiplodins from mangrove endophytic fungus Lasiodiplodia sp. 318#

Four new lasiodiplodins (1–4), together with three known analogues, have been isolated from a mangrove endophytic fungus, Lasiodiplodia sp. 318#. Their structures were elucidated by spectroscopic techniques. Cytotoxic activities of compounds 1–7 were evaluated in vitro against human cancer lines THP1, MDA-MB-435, A549, HepG2 and HCT-116. Compound 4 exhibited moderate cytotoxic activities.     

A new sesquiterpene from endophytic fungus Aspergillus sp

A fungal strain named YLF-14 was isolated from the leaf of Altingia yunnunensis. Based on the sequence at the internal transcribed spacer (ITS) region, the strain was identified as an Aspergillus sp.. A new sesquiterpene 5β,8aβ-dimethyl-3,4,4aβ,5,6,7,8,8a-octahydronaphthalene-1,2,5α-trimethanol (1) and a known compound 12-N-methylcyclo-(L-tryptophyl-L-phenylalanyl) (2) were isolated from the culture of this strain. Bioassay experiments showed that the two compounds had no obvious effect on the growth of tested bacteria and nematodes.     

A new phthalide from the endophytic fungus Xylaria sp. GDG-102

A new phthalide derivative, xylarphthalide A (1), along with two known compounds (-)-5-carboxylmellein (2) and (-)-5-methylmellein (3), were isolated from the endophytic fungus Xylaria sp. GDG-102 cultured from the Chinese medicinal plant Sophora tonkinensis. Their structures were identified by MS and NMR experiments, and the absolute configuration of 1 was further confirmed by single-crystal X-ray diffraction analysis. Compound 1–3 showed antibacterial activities against Bacillus megaterium, Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Shigella dysenteriae with MIC values of 12.5–25 μg/mL.     

Cytotoxic triquinane-type sesquiterpenoids from the endophytic fungus Cerrena sp. A593

Abstract

The culture broth of Cerrena sp. A593, which was isolated from Pogostemon cablin, showed potent cytotoxicity against several human tumor cell lines. The following chemical study resulted in the isolation of two new triquinane-type sesquiterpenoids, named cerrenins D (1) and E (2), along with two known compounds plerocybellone A (3) and chloriolin B (4). Their structures were fully assigned with the aid of extensive spectroscopic analysis (¹H and ¹³C NMR, HSQC, HMBC, ¹H-¹H COSY, HRESIMS, and IR) and data from the literature. Moreover, cytotoxic activity in vitro of compounds 1–4 were evaluated against SF-268, MCF-7, NCI-H460, and HepG-2 tumor cell lines. The new compound 1 exhibited weak growth inhibitory activity against all the four tumor cell lines with IC₅₀ values of 41.01, 14.43, 29.67, 44.32?μM.     

Polyketides with different post-modifications from desert endophytic fungus Paraphoma sp.

Three new polyketides 4,6,8-trihydroxy-5-methyl-3,4-dihydronaphthalen-1(2H)-one (1), 5,7-dihydroxy-3-(1-hydroxyethyl)-3,4-dimethylisobenzofuran-1(3H)-one (2) and 1-(4-hydroxy-6-methoxy-1,7-dimethyl-3-oxo-1,3-dihydroisobenzofuran-1-yl) ethyl acetate (3) together with seven known analogues (4–10) were isolated from desert endophytic fungus Paraphoma sp. The structures of these compounds were elucidated by analysis of NMR data. The absolute configuration of (1–3) was established on the basis of CD experiments. The possible biosynthetic pathway of compounds (1–10) was suggested, which implied that these secondary metabolites might be originated from polyketide biosynthesis with different post-modification reactions. Compounds 2, and 5–8 were evaluated for bioactivities against plant pathogen A. solani, whereas none of them displayed any biological effects. In addition, compounds 1, 2 and 5–10 were also tested for cytotoxic activities against three human cancer cell lines (HepG2 cells, MCF-7 cells and Hela cells) without biological effects.