Bioactive polyketides and meroterpenoids from the mangrove-derived fungus Talaromyces flavus TGGP35.

Six new polyketides, which includes three new lactones (talarotones A-C) (1-3), one new polyketide (talarotide A) (4), two new polyenes (talaroyenes A, B) (5, 6), together with one new meroterpenoid (talaropenoid A) (7) and 13 known compounds (8-20) were isolated from the mangrove-derived fungus Talaromyces flavus TGGP35. The structure and configuration of the compounds 1-7 were elucidated from the data obtained from HR-ESI-MS, IR, 1D/2D NMR spectroscopy, Mo2 (OAc)4-induced electronic circular dichroism (ECD), CD spectroscopy, and modified Mosher's method. Compounds 5 and 20 displayed antioxidant activity with IC50 values of 0.40 and 1.36 mM, respectively. Compounds 3, 6, 11, 16, and 17 displayed cytotoxic activity against human cancer cells Hela, A549, and had IC50 values ranging from 28.89 to 62.23 µM. Compounds 7, 10-12, and 14-18 exhibited moderate or potent anti-insect activity against newly hatched larvae of Helicoverpa armigera Hubner, with IC50 values in the range 50-200 µg/mL. Compound 18 showed antibacterial activity against Ralstonia solanacearum with the MIC value of 50 µg/mL.

Four New Polyhydroxy Cyclohexanes from the Stems of Fissistigma tientangense.

Four undescribed polyhydroxy cyclohexanes, fissoxhydrylenes A-D (1-4), together with two known biogenetically related polyhydroxy cyclohexanes (5 and 6) were isolated from the stems of Fissistigma tientangense Tsiang et P. T. Li. Their structures were elucidated by detailed analysis of NMR, HR-ESI-MS, IR, UV and Optical rotations data. The absolute configuration of 1 was confirmed by X-ray crystallographic. The absolute configurations of 2-4 were confirmed by chemical reaction and optical rotations. Compound 4 represent the first example of a no substituent polyhydroxy cyclohexanes from natural products. All isolated compounds were evaluated for their anti-inflammatory activities against the lipopolysaccharide-induced nitric oxide (NO) production in mouse macrophage RAW 264.7 cells in vitro. Compounds 3 and 4 showed inhibitory activities with the IC50 values of 16.63±0.06 µM and 14.38±0.08 µM, respectively.

Guaiane-Type Sesquiterpenes from the Stems of Fissistigma oldhamii.

Two new guaiane-type sesquiterpenes dysodensiols J and L, one new natural product dysodensiol K together with four known biogenetically related guaiane-type sesquiterpenes were isolated from the stems of Fissistigma oldhamii. Their structures were elucidated by detailed analysis of NMR, HR-ESI-MS, IR and Optical rotations data. Compound 1 contains an uncommon five-membered ether ring. The inhibitory effect of all compounds on the proliferation of primary synovial cells was evaluated. Compound 3 showed inhibitory activity with an IC50 value of 6.8 µM. Compounds 5-7 exhibited moderate inhibitory activity with IC50 values of 23.8, 26.6, and 27.1 µM, respectively.

Talaromarins A-F: Six New Isocoumarins from Mangrove-Derived Fungus Talaromyces flavus TGGP35.

Six new isocoumarin derivative talaromarins A-F (1-6), along with 17 known analogues (7-23), were isolated from the mangrove-derived fungus Talaromyces flavus (Eurotiales: Trichocomaceae) TGGP35. Their structures were identified by detailed IR, UV, 1D/2D NMR and HR-ESI-MS spectra. The absolute configurations of new compounds were determined by the modified Mosher's method and a comparison of their CD spectra with dihydroisocoumarins described in the literature. The antioxidant, antibacterial, anti-phytopathogenic and inhibitory activity against α-glucosidase of all the isolated compounds were tested. Compounds 6-11, 17-19 and 21-22 showed similar or better antioxidant activity than the IC50 values ranging from 0.009 to 0.27 mM, compared with the positive control trolox (IC50 = 0.29 mM). Compounds 10, 18, 21 and 23 exhibited strong inhibitory activities against α-glucosidase with IC50 values ranging from 0.10 to 0.62 mM, while the positive control acarbose had an IC50 value of 0.5 mM. All compounds showed no antibacterial or anti-phytopathogenic activity at the concentrations of 50 µg/mL and 1 mg/mL, respectively. These results indicated that isocoumarins will be useful to developing antioxidants and as diabetes control agents.

Rare isotachin-derived from the Dasymaschalon rostratum fungus Penicillium tanzanicum ZY-5.

Four rare isotachin-derived, isotachins E-H (1-4), together with two known biogenetically related isotachin derivatives (5 and 6) were isolated from the solid rice fermentation of a fungus Penicillium tanzanicum ZY-5 obtained from a medicinal plant Dasymaschalon rostratum collected from the Changjiang County, Hainan Province, China. Their structures were elucidated using comprehensive spectroscopic methods. The single-crystal X-ray diffraction of compound 5 was determined. Compounds 1-4 have a trans-3-(methylthio)-acrylic acid fragment, which are rare in nature. The inhibitory activities of all compounds against the nitric oxide (NO) production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells in vitro were evaluated.

One new α,ß-unsaturated 7-ketone sterol from the mangrove-derived fungus Phomopsis sp.MGF222.

A new α,ß-unsaturated 7-ketone sterol, 5ß,6ß-epoxy-3ß, 15α-dihydroxy-(22E,24R)-ergosta-8(14),22-dien-7-one (1), along with five known sterone derivatives, 5ß,6ß-epoxy-3ß,7α-dihydroxy-(22E,24R)-ergosta-8(14),22-dien-15-one (2), 5ß,6ß-epoxy-3ß,7α,9α-trihydroxy-(22E,24R)-ergosta-8(14),22-dien-15-one (3), 3ß,9α,15α-trihydroxy-(22E,24R)-10(5→4)-abeo-ergosta-6,8(14),22-trien-5-one (4), 3,15-dihydroxyl-(22E,24R)-ergosta-5,8(14),22-trien-7-one (5) and (22E,24R)-ergosta-4,6,8(14),22-tetraen-3,15-dione (6) were isolated from the mangrove-derived fungus Phomopsis sp. MGF222. Their structures were established on the basis of extensive spectroscopic data and comparison with the data of literature. Compound 2 showed weak antibacterial activity against Micrococcus tenuis with the MIC value of 28.2 (±0.52) µM. Compound 5 exhibited moderate antibacterial activity against Staphylococcus aureus with the MIC value of 14.6 (±0.47) µM.

A new phenol derivative isolated from mangrove-derived fungus Eupenicillium sp. HJ002.

A new phenol derivative, 3-chloro-5-hydroxy-4-methoxyphenylacetic acid methyl ester (1), along with five known compounds methyl 4-hydroxyphenylacetate (2), cytosporone B (3), (R)-striatisporolide A (4), (R)-butanedioic acid (5) and ergosterol (6) were isolated from the mangrove-derived fungus Eupenicillium sp. HJ002. Their structures were established by spectroscopic methods, GIAO based 13C NMR chemical shift calculations and comparison with the data of literature. Compounds 1-5 were isolated from Xylocarpus granatum Koening-derived fungus for the first time.

Four New Chromone Derivatives from Colletotrichum gloeosporioides.

Four previously unreported chromones, 5-hydroxy-2-(hydroxymethyl)-8-methoxy-4H-chromen-4-one (1), (5R,7S)-5,7-dihydroxy-2-propyl-5,6,7,8-tetrahydro-4H-chromen-4-one (2), (5R,7S)-5,7-dihydroxy-2-methyl-5,6,7,8-tetrahydro-4H-chromen-4-one (3), and (5R,7S)-5,7-dihydroxy-2-[(E)-prop-1-en-1-yl]-5,6,7,8-tetrahydro-4H-chromen-4-one (4), as well as one known analogue 5-hydroxy-2-methyl-4H-chromen-4-one (5) were isolated from the fermentation broth of the endophytic fungus Colletotrichum gloeosporioides derived from the mangrove Ceriops tagal. Their structures were elucidated based on extensive spectroscopic analyses. The absolute configurations of 2-4 were determined by comparison the experimental and calculated electronic circular dichroism (ECD) spectra. Compound 2 showed cytotoxic activity against A549 cell line with the IC50 value of 0.094 mm.

Four New Insecticidal Xanthene Derivatives from the Mangrove-Derived Fungus Penicillium sp. JY246.

Four new xanthene derivatives, penicixanthenes A-D (1-4), and one known compound 5 were isolated from a marine mangrove endophytic fungus Penicillium sp. JY246 that was obtained from the stem of Ceriops tagal. Their structures were determined by detailed NMR, MS spectroscopic data, modified Mosher's method, and calculated electronic circular dichroism data. All of the isolated compounds were examined for insecticidal activity. Compounds 2 and 3 showed growth inhibition activity against newly hatched larvae of Helicoverpa armigera Hubner with the IC50 values 100 and 200 µg/mL, respectively, and compounds 1, 3, and 4 showed insecticidal activity against newly hatched larvae of Culex quinquefasciatus with LC50 values of 38.5 (±1.16), 11.6 (±0.58), and 20.5 (±1) µg/mL, respectively. The four xanthene derivatives have the potential to be developed as new biopesticides.

Bioactive Lactones from the Mangrove-Derived Fungus Penicillium sp. TGM112.

Three new lactones penicilactones A-C (1-3) were obtained from the mangrove-derived fungus Penicillium sp. TGM112. Their structures and absolute configurations were determined by detailed NMR, MS spectroscopic data, Mo2(OAc)4-induced electronic circular dichroism (ECD), and circular dichroism (CD) spectroscopy. Compound 1 showed antibacterial activity against Staphylococcus aureus with an MIC value of 6.25 µg/mL. Compound 2 showed insecticidal activity against newly hatched larvae of Culex quinquefasciatus with the LC50 value of 78.5 (±0.58) µg/mL.

Three new polyketides from a mangrove-derived fungus Colletotrichum gloeosporioides.

Three new polyketides, (2S)-2,3-dihydro-5,6-dihydroxy-2-methyl-4H-1-benzopyran-4-one (1), (2'R)-2-(2'-hydroxypropyl)-4-methoxyl-1,3-benzenediol (2), and 4-ethyl-3-hydroxy-6-propenyl-2H-pyran-2-one (3) were isolated from the culture broth of Colletotrichum gloeosporioides, an endophytic fungus derived from the mangrove Ceriops tagal. The structures of 1-3 were elucidated on the basis of NMR spectra and HR-ESI-MS data. Their absolute configurations were determined by comparing with the experimental and calculated ECD spectrum. Compounds 1 and 3 showed potent antibacterial activities against some of the tested microbes.

Bioactive Meroterpenoids and Isocoumarins from the Mangrove-Derived Fungus Penicillium sp. TGM112.

Two new meroterpenoids, penicianstinoids A and B (1 and 2), and eight new isocoumarins, peniciisocoumarins A-H (3-10), together with 10 known analogues (11-20) were obtained from the mangrove-derived fungus Penicillium sp. TGM112. The structures and absolute configurations of 1-10 were determined by interpretation of detailed NMR, MS spectroscopic data, X-ray diffraction analyses, modified Mosher's method, and calculated electronic circular dichroism data. Compounds 1-4, 7, 8, 10, 12, 13, and 16 showed growth inhibition activity against newly hatched larvae of Helicoverpa armigera Hubner with IC50 values ranging from 50 to 200 µg/mL, respectively. Compounds 1, 2, and 11-15 displayed activity against Caenorhabditis elegans with EC50 values ranging from 9.4 (± 1.0) to 38.2 (± 0.6) µg/mL, respectively. Compound 1 represents an austinoid-like meroterpenoid that is reported here for the second time, in which a carbon-carbon double bond was oxidized to a carbonyl group at C-1'-C-2'.

Bioactive cytosporone derivatives isolated from the mangrove-derived fungus Dothiorella sp. ML002.

Three new cytosporone derivatives dothiorelones K-M (1, 2 and 7), together with six known ones (3-6, 8 and 9) were isolated from the mangrove-derived fungus Dothiorella sp. ML002. Their structures were determined by comprehensive 1D, 2D NMR spectroscopic and HR-ESI-MS spectroscopic data. Compounds 1, 2 and 5 displayed inhibitory activities against α-glucosidase with the IC50 values of 22.0, 77.9 and 5.4 µg/mL, respectively. Additionally, compounds 1, 2, and 5 also exhibited antibacterial activities against Staphylococcus aureus (ATCC 6538) with the same MIC values of 50 µg/mL, respectively. The results indicated that cytosporone derivatives will be useful to as diabetes control agents.

Chemical constituents from ethanol extract of Polyalthia rumphii branches and their cytotoxicity evaluation

ABSTRACT Twelve known compounds, including eight alkaloids, three lignans and one gossypol derivative, were isolated from the branches of Polyalthia rumphii (Blume ex Hensch.) Merr., Annonaceae. The chemical structures were determined by spectroscopic methods and comparison with literature data. All the isolates were evaluated the cytotoxicity against three human cancer cell lines: Hela, MCF-7 and A549, the results showed that partial of isolates displayed weak cytotoxicities with the IC50 values ranging from 25 to 40 µg/ml.

Penicilindoles A-C, Cytotoxic Indole Diterpenes from the Mangrove-Derived Fungus Eupenicillium sp. HJ002.

Three new indole diterpenes, penicilindoles A-C (1-3), were isolated from the mangrove-derived fungus Eupenicillium sp. HJ002. Their planar structures and absolute configurations were determined by interpretation of NMR spectroscopic data, HR-ESIMS, and X-ray diffraction analysis using Cu Kα radiation. The cytotoxic and antibacterial activities were evaluated in vitro; penicilindole A (1) showed cytotoxic activity against human A549 and HepG2 cell lines with IC50 values of 5.5 and 1.5 µM, respectively.

One new cytochalasin metabolite isolated from a mangrove-derived fungus Daldinia eschscholtzii HJ001.

One new cytochalasin metabolite [11]-cytochalasa-5(6),13-diene-1,21-dione-7,18-dihydroxy-16,18-dimethyl-10-phenyl-(7S*,13E,16S*,18R*) (1), together with three known compounds (2-4) were obtained from the EtOAc extract of the endophytic fungus Daldinia eschscholtzii HJ001 isolated from the mangrove Brguiera sexangula var. rhynchopetala collected in the South China Sea. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. Compounds 1 and 2 were evaluated for their antibacterial and cytotoxic activities.

Hepatoprotective triterpenoids and lignans from the stems of Schisandra pubescens.

One new triterpenoid (1) and 13 known compounds (2-14) were isolated from Schisandra pubescens stems. The structure of the new compound was established on the basis of 1D/2D NMR and HRESIMS spectroscopic analyses. The isolated compounds were evaluated for their hepatoprotective activities against D-GalN-induced cell injury in QSG7701 cells. Compounds 1, 13 and 14 at 10 µM showed hepatoprotective activities, with survival rates of 60.5, 50.4 and 48.9%, respectively.

Dihydroisocoumarins from the Mangrove-Derived Fungus Penicillium citrinum.

Three new dihydroisocoumarin penicimarins G-I (1-3), together with one known dihydroisocoumarin (4) and three known meroterpenoids (5-7), were obtained from a fungus Penicillium citrinum isolated from the mangrove Bruguiera sexangula var. rhynchopetala collected in the South China Sea. Their structures were elucidated by the detailed analysis of spectroscopic data. The absolute configuration of 1 was determined by the X-ray diffraction analysis using Cu Kα radiation. The absolute configurations of 2 and 3 were determined by comparison of their circular dichroism (CD) spectra with the literature. All compounds were evaluated for their antibacterial activities and cytotoxic activities.

Heteroclitins R-S: new dibenzocylooctadiene lignans from Kadsura heteroclita.

AIM: To study the dibenzocylooctadiene lignans from the stems of Kadsura heteroclita. METHOD: Chromatographic separations of silica gel and semi-preparative HPLC were used. All of the structures were elucidated on the basis of spectroscopic analysis, including 2D-NMR and HR-MS techniques. RESULTS: Four dibenzocylooctadiene lignans were isolated from K. heteroclita. Their structures were identified as heteroclitin R (1), heteroclitin S (2), gonisin O (3), and schisanlignone A (4). CONCLUSION: Heteroclitin R (1) and heteroclitin S (2) are new natural lignans.

[Renchangianin E: a new dibenzocyclooctadiene lignan from Kadsura renchangiana].

A new dibenzocyclooctadiene lignan, renchangianin E (1) was isolated from the stems of Kadsura renchangiana. Its structure and stereochemistry were elucidated by spectroscopic methods, including 2D-NMR techniques.