A new secondary metabolite from the marine-derived fungus Phomopsis lithocarpus FS508.

Based on the One Strain-Many Compounds (OSMAC) strategy, the secondary metabolites of Phomopsis lithocarpus FS508 were investigated. As a result, a new secondary metabolite, 4-methoxy-3-[4-(acetyloxy)-3-methyl-2-butenyl]benzoic acid (1) as well as eleven known compounds were isolated from the fermentation product of the strain FS508. Their structures were determined by NMR, IR, UV, and MS spectroscopic data analyses. All the isolated compounds were evaluated for cytotoxic and anti-inflammatory activities. Among them, compounds 3 and 9 displayed potent cytotoxicity against HepG-2 cell line, and compounds 2, 3 and 12 showed significant anti-inflammatory activities.

Cytosporins A-D, novel benzophenone derivatives from the endophytic fungus Cytospora rhizophorae A761.

Four novel benzophenone derivatives, cytosporins A-D (1-4), hemiterpene-conjugated phenolics with an unprecedented benzo[b][1,5]dioxocane skeleton, were isolated from Cytospora rhizophorae A761. The structures of the new compounds were fully characterized on the basis of extensive spectroscopic analysis. The deduced structure represents the first example of natural meroterpenoids which bear a benzo[b][1,5]dioxocane framework embodying hemiterpene and benzophenone moieties. Moreover, compounds 1-4 were evaluated for in vitro antimicrobial activity.

Tersone A-G, New Pyridone Alkaloids from the Deep-Sea Fungus Phomopsis tersa.

Four phenylfuropyridone racemates, (±)-tersones A-C and E (1-3, 5), one phenylpyridone racemate, (±)-tersone D (4), one new pyridine alkaloid, tersone F (6), single new phenylfuropyridone, tersone G (7) and two known analogs 8 and 9 were isolated from the deep-sea fungus Phomopsis tersa. Their structures and absolute configurations were characterized on the basis of comprehensive spectroscopic analyses, single-crystal X-ray diffraction experiments, and electronic circular dichroism (ECD) calculations. Moreover, compounds 1-9 were evaluated for in vitro antimicrobial and cytotoxic activity. Compounds 5b and 8b exhibited antibacterial activity against S. aureus with the MIC value of 31.5 µg/mL, while compound 5b showed cytoxic activities against SF-268, MCF-7, HepG-2 and A549 cell lines with IC50 values of 32.0, 29.5, 39.5 and 33.2 µM, respectively.

Chromone-Derived Polyketides from the Deep-Sea Fungus Diaporthe phaseolorum FS431.

Five new chromone-derived polyketides phaseolorins A-F (1⁻5), together with nine known compounds, were isolated from the deep-sea derived fungus Diaporthe phaseolorum FS431. The structures of new compounds were determined by analysis of their NMR and high-resolution electrospray ionization mass spectroscopy (HRESIMS) spectroscopic data. The absolute configurations were confirmed by chemical transformations, extensively experimental electron capture detection (ECD) calculations, or X-ray crystallography. Among them, compound 2 represented the first example for a new family of chromone derivative possessing an unprecedented recombined five-member γ-lactone ring. Moreover, the new compounds (1⁻5) were evaluated for in vitro cytotoxic activities against a panel of human cancer cell lines.

Two new 12-membered macrolides from the endophytic fungal strain Cladosprium colocasiae A801 of Callistemon viminalis.

Two new polyketide metabolites, the 12-membered macrolides 4-hydroxy-12-methyloxacyclododecane-2,5,6-trione (1) and 12-methyloxacyclododecane-2,5,6-trione (2), were isolated from the endophytic fungal strain Cladosprium colocasiae A801 of the plant Callistemon viminalis, together with five known derivatives. Their structures were fully characterized by means of detailed spectroscopic analysis for new structures, and in comparison with published data for known compounds. The antibacterial, cytotoxic, and α-glucosidase inhibitory activities of the new compounds 1 and 2 were evaluated.

Two new metabolites from Daldinia eschscholtzii, an endophytic fungus derived from Pogostemon cablin.

The chemical investigation of the mycelia of endophytic fungus Daldinia eschscholtzii A630, which was isolated from the medicinal plant Pogostemon cablin, resulted in the isolation of two new compounds, named eschscholin A (1), 3-ene-2-methyl-2H-1-benzopyran-5-ol (2), and one new natural product 3,5-dihydroxy-2-methyl-4H-chromen-4-one (3), along with seven known compounds. Their structures were fully characterized by means of detailed spectroscopic analysis, and in comparison with published data for known compounds. All of the isolated compounds (1-10) were evaluated for their antibacterial activities.

Cytotoxic Polyketides from a Deep-Sea Sediment Derived Fungus Diaporthe phaseolorum FS431.

Two new chromone-derived polyketides phaseolorins, G and H (1 and 2), and one new anthraquinone derivative, phaseolorin I (3), together with three known compounds (4-6), were isolated from the deep-sea sediment-derived fungus Diaporthe phaseolorum FS431. The structures of the new compounds were determined by comprehensive analysis of their spectroscopic data, and the absolute configuration of 1 was established by quantum chemical calculations of electron capture detection (ECD). All the isolated compounds (1-6) were tested for their in vitro cytotoxic activities against four human tumor cell lines, of which compound 4 exhibited significant effect against MCF-7, HepG-2, and A549 tumor cell lines with IC50 values of 2.60, 2.55, and 4.64 µM, respectively.

Highly Substituted Benzophenone Aldehydes and Eremophilane Derivatives from the Deep-Sea Derived Fungus Phomopsis lithocarpus FS508.

Five new benzophenone derivatives named tenellones D⁻H (1⁻5), sharing a rare naturally occurring aldehyde functionality in this family, and a new eremophilane derivative named lithocarin A (7), together with two known compounds (6 and 8), were isolated from the deep marine sediment-derived fungus Phomopsis lithocarpus FS508. All of the structures for these new compounds were fully characterized and established on the basis of extensive spectroscopic interpretation and X-ray crystallographic analysis. Compound 5 exhibited cytotoxic activity against HepG-2 and A549 cell lines with IC50 values of 16.0 and 17.6 µM, respectively.

Anti-inflammatory and antimicrobial coumarins from the stems of Eurya chinensis.

Two new coumarins, named (±)-euryacoumarin A (1) and 6-demethylobtusinin (2), and one new natural coumarin, named euryacoumarin B (3), along with two known compounds, scopoletin (4) and obtusinol (5), were isolated from the stems of Eurya chinensis. Their structures were elucidated by means of extensive spectroscopic methods and comparison with data reported in the literatures. Compound 1 exhibited significant inhibition of LPS-induced nitric oxide (NO) production in RAW264.7 cells with IC50 value of 35.64 ± 1.73 µM, and showed marginal antibacterial activities against Bacillus subtilis and B. cereus with MIC values of 50.59 ± 2.12 and 35.42 ± 0.96 µM, respectively.

Monoterpenes and sesquiterpenes from the marine sediment-derived fungus Eutypella scoparia FS46.

Eutypellol A (1), the first norsesquiterpenoid of sequicarene family, as well as eutypellol B (2), a rare 7-methyl oxidized 2-carene derivative, and one new natural product 2-(2-hydroxy-4-methylcyclohex-3-enyl)propanoic acid (3), along with eight known terpenoids, were isolated from the marine sediment-derived fungus Eutypella scoparia FS46 collected from the South China Sea. Their structures were established on the basis of extensive spectroscopic analysis. Compounds 1-3 were evaluated for their antibacterial activities against Staphylococcus aureus and cytotoxic activities against MCF-7, NCI-H460, and SF-268 tumor cell lines.

Two New Metabolites from the Endophytic Fungus Alternaria sp. A744 Derived from Morinda officinalis.

Two new compounds isobenzofuranone A (1) and indandione B (2), together with eleven known compounds (3-13) were isolated from liquid cultures of an endophytic fungus Alternaria sp., which was obtained from the medicinal plant Morinda officinalis. Among them, the indandione (2) showed a rarely occurring indanone skeleton in natural products. Their structures were elucidated mainly on the basis of extensive spectroscopic data analysis. All of the compounds were evaluated with cytotoxic and α-glucosidase inhibitory activity assays. Compounds 11 and 12 showed significant inhibitory activities against four tumor cell lines; MCF-7, HepG-2, NCI-H460 and SF-268, with IC50 values in the range of 1.91-9.67 µM, and compounds 4, 5, 9, 10, 12 and 13 showed excellent inhibitory activities against α-glucosidase with IC50 values in the range of 12.05-166.13 µM.

[Sesquiterpenoids of endophytic fungus Cerrena sp. from Pogostemon cablin and their cytotoxic activities].

The secondary metabolites of endophytic fungus Cerrena sp.A593 from Pogostemon cablin and their cytotoxic activities were investigated. Eight sesquiterpenoids were isolated from the fermentation broth of the strain A593 by silica gel, reverse phase silica gel, Sephadex LH-20, HPLC and so on. Their structures were identified as chloriolin B(1), chloriolin C(2), pleurocybellone A(3), dihydrohypnophilin(4), cucumin F(5), antrodin A(6), 10α-hydroxyamorphan-4-en-3-one(7), and connatusin A(8). Compounds 1- 8 were firstly found from the genus Cerrena. All isolated sesquiterpenoids were evaluated for in vitro cytotoxic activities against HepG-2, SF-268, MCF-7 and NCI-H460 tumor cell lines. Compounds 1-3 showed inhibitory activities against the four tumor cell lines with IC50 values ranging from 20.33 to 63.13 µmol•L⁻¹.

Rhodomentones A and B, novel meroterpenoids with unique NMR characteristics from Rhodomyrtus tomentosa.

Two novel meroterpenoids, rhodomentones A and B bearing an unprecedented caryophyllene-conjugated oxa-spiro[5.8] tetradecadiene skeleton, were isolated from the leaves of Rhodomyrtus tomentosa. Their structures with unique NMR characteristics were determined by extensive spectroscopic analysis, single-crystal X-ray diffraction, quantum molecular calculation, chemical transformation as well as total synthesis.

Dichotocejpins A-C: New Diketopiperazines from a Deep-Sea-Derived Fungus Dichotomomyces cejpii FS110.

Three new diketopiperazines, dichotocejpins A-C (1-3), together with eight known analogues (4-11), were isolated from the culture of the deep-sea sediment derived fungus Dichotomomyces cejpii FS110. Their structures, including absolute configurations, were elucidated by a combination of HRESIMS, NMR, X-ray crystallography, and ECD calculations. Compounds 4-6, 10-11 showed significant cytotoxic activities against MCF-7, NCI-H460, HepG-2, and SF-268 tumor cell lines. Compound 1 exhibited excellent inhibitory activity against α-glucosidase with an IC50 of 138 µM.

Antimicrobial acylphloroglucinols from the leaves of Rhodomyrtus tomentosa.

Phytochemical study on the leaves of Rhodomyrtus tomentosa resulted in the isolation of fourteen compounds including a new acylphloroglucinol, named tomentosone C (1), and a new flavonol glycoside, namely myricetin-3,7,3'-trimethyl ether-5'-O-ß-glucopyranoside (2). Their structures were characterized by spectral data interpretation for new structures and in comparison with published data for known compounds. The antimicrobial activity evaluation revealed that 1 and the known acylphloroglucinol rhodomyrtone (3) exhibited significant antimicrobial activity with MIC 3.66 and 1.83 µg ml(-1), respectively, toward Staphylococcus aureus, responsible for the antimicrobial activity observed with the n-hexane and EtOAc-soluble fraction of the ethanol extract of R. tomentosa leaves.

Two new xyloketals from the endophytic fungus Endomelanconiopsis endophytica derived from medicinal plant Ficus hirta.

Chemical examination of the liquid culture of Endomelanconiopsis endophytica A326 isolated from the Chinese folk medicine Ficus hirta resulted in the isolation of two new xyloketals named xyloketals K and L (1-2) and three known analogs (3-5) including a new natural product (5). Their structures were determined on the basis of extensive spectroscopic analysis. All compounds were evaluated for their cytotoxic activities against the SF-268, MCF-7, NCI-H460, and HepG-2 tumor cell lines. Nonetheless, no significant activity was observed.

Perangustols A and B, a pair of new azaphilone epimers from a marine sediment-derived fungus Cladosporium perangustm FS62.

A pair of new azaphilone epimers, perangustols A-B (1-2), and two new natural products (3-4), together with two known metabolites (5-6) were isolated from the culture of the marine sediment-derived fungus Cladosporium perangustum FS62. The structures of these compounds were established on the basis of extensive spectroscopic analysis. The isolated compounds (1-6) were evaluated for their cytotoxic activities against the SF-268, MCF-7, NCI-H460, and HepG-2 tumor cell lines. Nonetheless, no significant activity was observed.

Cytotoxic trichothecene macrolides from the endophyte fungus Myrothecium roridum.

A new cytotoxic roridin-type trichothecene macrolide named epiroridin acid (1) and two known compounds epiroridin E (2) and mytoxin B (3) were isolated from the liquid culture of Myrothecium roridum A553, which was isolated from the medicinal plant Pogostemon cablin. The structure of the new macrolide (1) was elucidated by extensive spectroscopic measurements (UV, IR, MS, and 1D and 2D NMR) analyses. All isolated compounds (1-3) were evaluated for their cytotoxic activities against SF-268, MCF-7, NCI-H460, and HepG-2 tumor cell lines. The new compound (1) exhibited well cytotoxicity against the four selected tumor cell lines.

Two New Secondary Metabolites from the Endophytic Fungus Endomelanconiopsis endophytica.

Two new secondary metabolites, endomeketals A-B (1-2), a new natural product (3), and a known compound (4) were isolated from the ethyl acetate extract of the endophytic fungus Endomelanconiopsis endophytica A326 derived from Ficus hirta. Their structures were determined on the basis of extensive spectroscopic analysis. All compounds were evaluated for their cytotoxic activities against SF-268, MCF-7, NCI-H460, and HepG-2 tumor cell lines. However, no compound showed cytotoxic activity against these human tumor cell lines.

[Chemical Constituents from Mitrasacme pygmaea].

Objective: To study the chemical constituents from Mitrasacme pygmaea. Methods: The compounds were isolated and purified by column chromatography and their structure were identified by NMR and MS,and comparison spectral data with literature. Results: Eleven compounds were isolated and identified as tricin-7-O-ß-D-glucopyranoside( 1),massonianoid A( 2),kaempferol( 3),cinnamic acid( 4),quercetin( 5),tiliroside( 6),tricin( 7),ß-sitosterol( 8),adenosine( 9),α-tocopherolquinone( 10)and ß-daucosterol( 11). Conclusion: All the compounds are isolated from this genus for the first time.