A new sesquiterpene from the entomogenous fungus Phomopsis amygdali

A new sesquiterpene, (+)-S-1-methyl-abscisic-6-acid (1), together with five known compounds, (+)-S-abscisic acid (2), fusicoccin J (3), 3α-hydroxyfusicoccin J (4), (R)-5-hydroxymethylmellein (5) and 4-hydroxyphenethyl acetate (6) was isolated from the fermentation extract of Phomopsis amygdali, an entomogenous fungus isolated from Call midge. Their structures were determined mainly by analysis of MS and NMR spectroscopic data. Compounds 1–6 were tested for antimicrobial activity against three plant pathogenic fungi: Gibberella zeae, Verticillium albo-atrum, and Fusarium nivale, and two bacteria: Escherichia coli and Pseudomonas aeruginosa 2033E. As a result, compounds 1–4 displayed antibacterial activity against Gram-negative P. aeruginosa 2033E, and the minimum inhibition concentration (MIC value) of 1–4 is 30 μg/mL, 58 μg/mL, 26 μg/mL, and 26 μg/mL, respectively.     

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.     

A new phthalic acid ester from Ajuga bracteosa

A new phthalic acid ester 1,2-benzenedicarboxylic acid bis(2S-methyl heptyl) ester (1) was isolated from the hexane extract of the whole plant of Ajuga bracteosa. In addition, chloroform and methanol extracts yielded neo-clerodane diterpene ajugarin-I and two iridoid glycosides, reptoside and 8-O-acetyl harpagide. The structures of all the compounds were confirmed by extensive spectroscopic analysis. From the two oily fractions nine and six volatile constituents respectively were identified by GCMS. Linalyl acetate was found to be common in both the oil fractions. This plant is a new source of linalyl acetate, a valuable perfumery compound.     

Antimicrobial chemical constituents from the endophytic fungus Phomopsis sp. from Notobasis syriaca

Phomosine K (1), a new phomosine derivative, has been isolated from Phomopsis sp., in addition to six known compounds: phomosine A (2), phenylalanine amide (3), 2-hydroxymethyl-4beta,5alpha,6beta-trihydroxycyclohex-2-en (4), (-)-phyllostine (5), (+)-epiepoxydon (6), and (+)-epoxydon monoacetate (7). Preliminary studies showed that compound 1 had strong antibacterial activity, while compounds 4-7 showed good antifungal, antibacterial, and algicidal properties, except compounds 4 and 6, which lacked antifungal activity.     

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.     

A new synthesis of the phytotoxin porritoxin

A convenient synthesis of the phytotoxin porritoxin is described. Central to the approach employed is the formation of the isoindolinone template obtained via a directed lithiation/Parham cyclization process enabling the concomitant connection of an acetal appendage. Further conversion into the requisite hydroxyalkyl chain, selective deprotection, and O-prenylation complete the synthesis of the title compound.     

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.     

A new eudesmane derivative and a new fatty acid ester from Sambucus williamsii

1,4,13-Trihydroxy-eudesm-11(12)-ene, a new eudesmane derivative (3), (9E)-8,11,12-trihydroxyoctadecenoic acid methyl ester, a new fatty acid ester (2) and tianshic acid (1) were obtained from the stems of Sambucus williamsii. Their structures were elucidated by physiochemical properties and spectroscopic analysis. Both compounds 1 and 2 showed stimulating effects on alkaline phosphatase activity of the osteoblastic UMR106 cell about 1.5 fold at 30 mumol/l while they had no effects on cell proliferation.     

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.     

A new ferulic acid ester from Rhodiola wallichiana var. cholaensis (Crassulaceae)

A new ferulic acid ester, 6-feruloyloxyhexanoic acid (1), was isolated along with 10 known ones (2–11), from the concentrated water extract of Rhodiola wallichiana var. cholaensis. Their chemical structures were elucidated on the basis of extensive spectroscopic methods including Two-dimensional nuclear magnetic resonance (2D NMR) experiments. Compound 3 was isolated from this plant for the first time. The protective effects against H₂O₂-induced myocardial cell injury in cultured H9c2 cells were also evaluated. Compounds 1, 5 and 7–11 provided significant protective effects on H₂O₂-induced H9c2 cells injury at the concentration of 25 μg/mL. And the protective effects of compound 1 was also investigated by the oxygen–glucose deprivation/reperfusion (OGD/R) tests.     

A novel alkenoic acid ester and a new benzophenone from Ranunculus ternatus

A novel alkenoic acid ester,(E)-4-hydroxy-dodec-2-enedioic acid-12-O-methyl ester and a new benzophenone,ethyl (S)-3-[2- (3,4-dihydroxybenzoyl)-4,5-dihydroxyphenyl]-2-hydroxypropanoate,together with a known compound,(E)-4-hydroxy-dodec-2- enedioic acids were isolated from the roots of Ranunculus ternatus.Their structures were elucidated by spectroscopic methods.     

A new fatty acid ester from an edible mushroom Rhizopogon luteolus

Phytochemical investigation of the Rhizopogon luteolus Fr. led to the isolation of one new fatty acid ester, 3-hydroxy-2,4-dimethylheptacosyl acetate (1) together with two known compounds tetracosanoic acid (2) and ergosterol (3). 1D and 2D NMR, and MS techniques were used for structural elucidation. Phenolic and fatty acid compositions were identified using HPLC–DAD and GC–MSD, respectively. Fumaric acid was the major phenolic acid, whereas linoleic, stearic and oleic acids were the most abundant fatty acids. Antioxidant and anticholinesterase activities of the extracts and compounds (1–3) were tested spectrophotometrically. Among the extracts, hexane extract showed the highest activity in all tests, particularly in β-carotene-linoleic acid assay (IC₅₀: 16.65 ± 1.12 μg/mL). Furthermore, compound 3 exhibited higher antioxidant and anticholinesterase activities. The study indicates that R. luteolus can be used in food, cosmetic and pharmaceutical industries.     

A new azaphilone from the entomopathogenic fungus Hypocrella sp.

This report describes the isolation of a new azaphilone, designated hypocrellone A (2), together with five known compounds (1, 3–6) from a submerged culture of the entomopathogenic fungus Hypocrella sp. (isolate WYTY-21). The absolute stereostructures of the two compounds (1 and 2) were elucidated based on 1D and 2D NMR spectroscopic and mass spectrometric data combined with the data from various chemical transformations. Hypocrellone A (2) and three (3–6) of the five known compounds were cytotoxic to hepatoma cells (cell line BEL-7404); IC₅₀ values ranged from 6.2 to 17.4 μM. At 200 μM, none of the six compounds was toxic to normal human liver cells (cell line HL-7702) or to normal human kidney epithelial cells (cell line HEK-293T).