Three New Sesquiterpenoids from Xylaria sp. NCY2

Three new sesquiterpenoids, xylarenones A ( 1 ) and B ( 2 ), and xylarenic acid ( 3 ), were obtained from the endophytic fungal strain Xylaria sp. NCY2, which was isolated from Torreya jackii Chun . Their structures were elucidated by spectroscopic analyses, including 1D‐ and 2D‐NMR experiments, and by HR‐Q‐TOF mass spectrometry. The antitumor and antibacterial properties of the new compounds were evaluated.     

Seven Novel Linear Polyketides from Xylaria sp. NCY2

Seven novel polyketides, namely, 1‐(xylarenone A)xylariate A ( 1 ), xylarioic acid B ( 2 ), xylariolide A ( 3 ), xylariolide B ( 4 ), xylariolide C ( 5 ), methyl xylariate C ( 6 ), and xylariolide D ( 7 ), together with the known one taiwapyrone ( 8 ), were isolated from the endophytic fungal strain Xylaria sp. NCY2 of Torreya jackii Chun . Their structures were elucidated by spectroscopic analyses, including 1D‐ and 2D‐NMR experiments, and on the basis of HR‐Q‐TOF mass spectrometry. Antitumor and antibacterial assays of compounds 1 – 8 were carried out, which show moderate activities.     

New Cytochalasins from the Marine‐Derived Fungus Xylaria sp. SCSIO 156

Two new cytochalasins, 18‐deoxycytochalasin Q ( 1 ) and 21‐O‐deacetylcytochalasin Q ( 2 ), together with four known analogues, cytochalasin Q ( 3 ), 19,20‐epoxycytochalasin Q ( 4 ), 21‐O‐deacetyl‐19,20‐epoxycytochalasin Q ( 5 ), and cytochalasin D ( 6 ), were isolated from the fungus Xylaria sp. SCSIO156 originated from the South China Sea marine sediment. The structures of 1 and 2 were elucidated by MS and 1D‐ and 2D‐NMR data analyses, and comparison with known compounds. The known compounds 3 – 6 were identified by comparison of their MS and NMR data with those reported in the literature. In the in vitro antitumor assay, compounds 2 – 6 showed mild cytotoxicity against three tumor cell lines (MCF‐7, SF‐268, and NCI‐H460).     

Secondary metabolites of Xylaria sp., an endophytic fungus from Taxus mairei

One new metabolite 3,7-dimethyl-9-(-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)nona-1,6-dien-3-ol, together with nine known compounds, were isolated from the strain Xylaria sp., an endophytic fungus of Taxus mairei. Their structures were deduced from 1D and 2D NMR data. In vitro cytotoxicity and antibacterial activity of these compounds were evaluated. Some of them exhibited substantial activity.     

Structure elucidation of three diphenyl ether derivatives from the mangrove endophytic fungus SBE‐14 from the South China Sea

Two new natural products, tenelate A ( 1 ) and B ( 2 ), together with the known compound, tenellic acid C ( 3 ), were isolated from the mangrove endophytic fungus Talaromyces sp. (SBE‐14), from the South China Sea. Their structures were elucidated by spectroscopic methods, mainly 1D and 2D NMR techniques. Copyright © 2009 John Wiley & Sons, Ltd.     

Chemical Constituents of the Endophytic Fungal Strain Phomopsis sp. NXZ‐05 of Camptotheca acuminata

From the endophytic fungal strain Phomopsis sp. NXZ‐05 of Camptotheca acuminata Decne . (Nyssaceae), six new compounds were isolated, including the ten‐membered macrolides 1 – 4 and their (known) parent compound multiplolide A ( 7 ), as well as a new unsaturated fatty acid, (4E)‐6,7,9‐trihydroxydec‐4‐enoic acid ( 5 ) and its methyl ester 6 . Their structures were elucidated by spectroscopic and mass‐spectrometric analyses, including 1D‐ and 2D‐NMR experiments and HR‐ESI‐MS, and their biological activities were elucidated.     

Pseudonocardides A – G,New γ‐Butyrolactones from Marine‐derived Pseudonocardia sp. YIM M13669

Seven new γ‐butyrolactones, named pseudonocardides A – G ( 1  –  7 ), were isolated from the marine‐derived actinomycete strain Pseudonocardia sp. YIM M13669. Their structures were elucidated on the basis of spectroscopic data including 1D‐ and 2D‐NMR, and HR‐ESI‐MS. The absolute configuration of 1 was determined by X‐ray crystallographic analysis of 1a (4‐bromobenzoate derivative of 1 ). The antibacterial activity against Mycobacterium smegmatis MC²155 and cytotoxicities of compounds 1  –  7 were evaluated in this study.     

New Lactone and Xanthone Derivatives Produced by a Mangrove Endophytic Fungus Phoma sp. SK3RW1M from the South China Sea

A new lactone, 1,8‐dihydroxy‐10‐methoxy‐3‐methyldibenzo[b,e]oxepine‐6,11‐dione ( 1 ), and two new xanthones, 1‐hydroxy‐8‐(hydroxymethyl)‐6‐methoxy‐3‐methyl‐9H‐xanthen‐9‐one ( 2 ) and 1‐hydroxy‐8‐(hydroxymethyl)‐3‐methoxy‐6‐methyl‐9H‐xanthen‐9‐one ( 3 ), were isolated from a mangrove endophytic fungus Phoma sp. SK3RW1M collected from the South China Sea. This is the first report on xanthone derivatives isolated as secondary metabolites from Phoma species. Their structures were elucidated by spectroscopic methods, mainly 1D‐ and 2D‐NMR techniques, and the structure of compound 2 was confirmed by X‐ray crystallography. Cytotoxicity assays showed that compounds 1 – 3 were inactive against KB and KBv200 cells.     

Tuberculariols A – C,New Sesquiterpenes from the Mutant Strain M‐741 of Tubercularia sp. TF5

Three new sesquiterpenes, tuberculariols A–C ( 1 – 3 , resp.), were isolated from the mutant strain M‐741 of Tubercularia sp. TF5, an endophytic fungus of Taxus mairei. Their structures were elucidated by spectroscopic analyses including 1D‐ and 2D‐NMR experiments, and HR‐Q‐TOF‐MS. Antitumor and antibacterial properties of these compounds were evaluated.     

Structural and Biological Properties of Vermistatin and Two New Vermistatin Derivatives Isolated from the Marine‐Mangrove Endophytic Fungus Guignardia sp. No. 4382

Vermistatin (=(3R)‐4,6‐dimethoxy‐3‐{4‐oxo‐6‐[(1E)‐prop‐1‐en‐1‐yl]‐4H‐pyran‐3‐yl}‐2‐benzofuran‐1(3H)‐one; 1 ) and two new vermistatin derivatives, compounds 2 and 3 , were isolated from the fungal strain Guignardia sp. No. 4382 obtained from the South‐China Sea. Their structures were elucidated by various methods, including circular dichroism (CD), 1D‐ and 2D‐NMR, and HR‐EI‐MS. The structures of 1 and 2 were unequivocally corroborated by X‐ray crystallography, and their absolute configurations were derived by CD spectroscopy based on a literature comparison. The in vitro cytotoxic and antifungal activities of 1 and 2 were tested.     

A new compound: Xyloketal H from mangrove fungus <Emphasis Type="Italic">Xylaria</Emphasis> sp. from the South China Sea coast

A new metabolite xyloketal H (1), was isolated from mangrove fungus Xylaria sp. (No.2508) obtained from the South China Sea. By spectroscopic analyses, primarily 2D NMR methods and X-ray diffraction experiments, its structure was elucidated. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 5–6, January–February, 2008.     

Characterization of Eight New Secondary Metabolites from the Mutant Strain G‐444 of Tubercularia sp. TF5

Eight new metabolites, including five new sesquiterpenoids, 10,11‐epoxyguaian‐10‐ol ( 1 ), 10,11‐epoxyguaian‐13‐ol ( 2 ), a new backbone sesquiterpene rearranged from guaiane ( 3 ), two 1,5 : 1,10‐disecoguaianes, 4 and 5 , two new dihydroisocoumarins, 7‐chloromellein‐4‐ol ( 6 ) and 7‐chloromellein‐5‐ol ( 7 ), and one new tetralone, 7‐chloroscytalone ( 8 ), were isolated from the mutant strain G‐444 of Tubercularia sp. TF5, an endophytic fungus of Taxus mairei, along with ten known compounds, 3,4‐dihydro‐4,8‐dihydroxy‐2H‐naphthalen‐1‐one ( 9 ), (3R,4S)‐4‐hydroxymellein ( 10 ), 5‐formylmellein ( 11 ), 5‐carboxymellein ( 12 ), sporogen‐AO1 ( 13 ), tuberculariols A ( 14 ) and B ( 15 ), hymatoxin E ( 16 ), 4‐oxo‐4H‐pyran‐3‐acetic acid ( 17 ), and penicillic acid ( 18 ). Their structures were elucidated by spectroscopic analyses including HR‐ESI‐MS, 1D‐ and 2D‐NMR (HMQC, HMBC, ¹H,¹H‐COSY and NOESY). The antimicrobial activities of 1 – 8 were evaluated, but none showed any substantial effect.     

N‐Bearing Furanone Derivatives from an Endophytic Fungus in Huperzia serrata

Two new polyketide derivatives, huaspenones C and D ( 1 and 2 , resp.), were isolated from the cultures of an endophytic fungus Peyronellaea sp. HS‐12, derived from the stems of Huperzia serrata. They share N‐bearing furan‐3(2H)‐one backbone, and 2 has an unprecedented furo[3,2‐c]pyridine skeleton. Their structures including the absolute configuration were elucidated by extensive spectroscopic analysis combined with quantum‐chemical calculations. (2E,4E)‐6‐hydroxy‐2‐methylocta‐2,4‐dienoic acid ( 3 ), a key intermediate of the biosynthesis of 1 and 2 , was also obtained from the endophyte.     

Isolation and Characterization of Secondary Metabolites from Rhododendron microphyton

Four new iridoids, incarvoids D–F ( 1 – 3 , resp.) and incarvoid B 9‐O‐β‐D ‐glucopyranoside ( 4 ), and one new monoterpenoid, argutoid B ( 5 ), along with 14 known compounds, were isolated from Rhododendron microphyton. Their structures were established by comprehensive 1D‐ and 2D‐NMR spectroscopic analysis.     

Three New ent‐Trachylobane Diterpenoids from Co‐cultures of the Calli of Trewia nudiflora and Fusarium sp. WXE

Five diterpenoids, including three new ent‐trachylobane diterpenoids, i.e., (3α)‐3‐hydroxy‐ent‐trachylobane‐17,19‐dioic acid 19‐methyl ester ( 1 ), ent‐trachylobane‐17,19‐dioic acid 19‐methyl ester ( 2 ), ent‐trachylobane‐17,19‐dioic acid ( 3 ), and two known atisane‐type ones, i.e., (16α)‐16,17‐dihydroxy‐ent‐atisan‐19‐oic acid methyl ester ( 4 ), and 17‐hydroxy‐ent‐atisan‐19‐oic acid methyl ester ( 5 ), were isolated from the co‐culture extract of the calli of Trewia nudiflora and its endophytic fungus Fusarium sp. WXE. Their structures were elucidated by spectroscopic analyses, including 1D‐ and 2D‐NMR experiments, and HR‐Q‐TOF mass spectrometry. The antitumor and antibacterial properties of the new compounds were evaluated.     

Three New Triterpenes from Xylarialean sp. A45, an Endophytic Fungus from Annona squamosa L.

From the fermentation extract of Xylarialean sp. A45, an endophytic fungus of Annona squamosa L., three new triterpenes, namely xylariacins A–C ( 1 – 3 , resp.) were obtained. Their structures were determined by spectroscopic analyses, including 1D‐ and 2D‐NMR experiments and HR‐ESI‐Q‐TOF mass spectrometry. The in vitro cytotoxic activities of compounds 1 – 3 were tested against human tumor cell line HepG2, and these compounds showed modest cytotoxic activity.     

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.     

两种南海海洋真菌2508代谢产物的DNA活性研究

研究了从南海海洋真菌2508号分离得到的一种新的海洋代谢产物Xylopyridine A (1)和一个已知代谢产物xylopyrazine A (2).他们的结构由光谱数据确定。同时通过荧光淬灭实验和光谱滴定实验研究了两种化合物与DNA的结合。结果表面1显示出很强的DNA结合作用并且是通过扦插结合的,可开发用于强DNA结合剂方面的用途。     

Structure elucidation of new fusarielins from Fusarium sp. and their antimicrobial activity

Three new fusarielins, 3‐epi‐fusarielin H ( 1 ), 3‐O‐methyl‐fusarielin H ( 2 ), and 3‐O‐methyl‐epi‐fusarielin H ( 3 ), were isolated from the fungus Fusarium sp. together with the known analogues, fusarielins F ( 4 ) and G ( 5 ). The structures of these compounds were elucidated by analysis of their ESI‐HRTOFMS, 1D and 2D NMR spectroscopic data. The new compounds exhibited weak antibacterial effect against Staphylococcus aureus.     

Two New Abietane Diterpenoids from the Roots of Tripterygium wilfordii Hook. f.

Two new abietane‐type diterpenoids, named triptobenzene R ( 1 ) and triptobenzene S ( 2 ), together with three known abietane‐type diterpenoids, triptophenolide ( 3 ), triptonodiol ( 4 ), and triptonoterpene methyl ether ( 5 ), were isolated from the roots of Tripterygium wilfordii Hook . f. Their structures and relative configurations were established by detailed spectral studies, including 1D‐ and 2D‐NMR (HSQC, HMBC, and NOESY), and HR‐ESI‐TOF‐MS, and by comparison with published data. Their absolute configurations were assigned by the CD technique, applied for the first time to abietane diterpenes from Tripterygium wilfordii. Compound 2 is the first abietane‐type norditerpenoid isolated from the genus Tripterygium.