New Pyrrolobenzoxazine Sesquiterpenoid Derivatives from the Fungus Talaromyces trachyspermus.

Three new pyrrolobenzoxazine sesquiterpenoids, talatrachyoxazines A - C (1:  - 3: ), together with fourteen known compounds (4:  - 17: ), were isolated from the fungus Talaromyces trachyspermus EU23. Their structures were identified by spectroscopic evidence and mass spectrometry. The absolute configurations of 1:  - 3: were determined by NOESY data and comparison of their calculated and experimental electronic circular dichroism (ECD) spectra. Compound 1: showed cytotoxic activity against HelaS3, KB, HT-29, MCF-7, and HepG2 cell lines with IC50 values of 7, 11, 10, 12, and 10 µM, respectively. Compounds 1: and 14: showed weak antibacterial activity against the gram-positive bacteria Bacillus cereus and Bacillus subtilis, while 1:  - 3: and 14: showed weak antibacterial activity against the gram-negative bacterium Pseudomonas aeruginosa. In addition, compound 1: showed weak antibacterial activity against Escherichia coli.

Meroterpenoid pyrones, alkaloid and bicyclic brasiliamide from the fungus Neosartorya hiratsukae.

Two new meroterpenoid pyrones, chevalone G (1) and aszonapyrone C (2), a new indole alkaloid, 7-chlorofischerindoline (3) and a new bicyclic brasiliamide, brasiliamide H (4), together with sixteen known compounds, 5-20 were isolated from the fungus Neosartorya hiratsukae. Their structures were established on the basis of spectroscopic evidence. The antibacterial activity and the cytotoxic activity of new compounds were evaluated.

Meroditerpene pyrone, tryptoquivaline and brasiliamide derivatives from the fungus Neosartorya pseudofischeri.

Two new meroditerpene pyrones, chevalone F (1) and 11-hydroxychevalone E (2), a new tryptoquivaline analog, tryptoquivaline V (3) and a new brasiliamide analog, brasiliamide G (4), together with thirteen known compounds, chevalones A-C (5-7), chevalone E (8), 11-hydroxychevalone C (9), pyripyropene A (10), isochaetominine C (11), pyrrolobenzoxazine terpenoids CJ-12662 (12) and CJ-12663 (13), fischerindoline (14), eurochevalierine (15), 1,4-diacetyl-2,5-dibenzylpiperazine-3,7''-oxide (16) and lecanorin (17) were isolated from the fungus Neosartorya pseudofischeri. Their structures were established on the basis of spectroscopic evidence. Compound 2 showed weak antibacterial activity against Escherichia coli and Salmonella enterica serovar Typhimurium, whereas compounds 7, 12, 13 and 15 showed antibacterial activity against Bacillus cereus and Staphylococcus aureus. In addition, compounds 13 and 14 showed cytotoxicity against KB and MCF-7 cancer cell lines, as well as the Vero cell line.

Types A and D Trichothecene Mycotoxins from the Fungus Myrothecium roridum.

Chromatographic separation of extracts from the fungal biomass of a plant pathogenic fungus, Myrothecium roridum, yielded 8 trichothecene toxins including 6 type D trichothecenes (1: -6: ) and 2 type A trichothecenes (7: -8: ). 6',12'-Epoxymyrotoxin A (1: ) and 7'-hydroxymytoxin B (2: ) were new macrocyclic trichothecenes, while the other trichothecenes were identified as myrotoxin B (3: ), myrotoxin D hydrate (4: ), 2',3'-epoxymyrothecine A (5: ), miotoxin A (6: ), and 2 trichothecenes lacking the macrocyclic lactone system, roridin L-2 (7: ) and trichoverritone (8: ). The structures of these mycotoxins were characterized using spectroscopic methods. The absolute configurations of 1: and 2: were determined by NOESY and a comparison of their experimental and calculated ECD spectra. Most of these mycotoxins (1: -4: and 6: ) exhibited highly potent antimalarial activity against Plasmodium falciparum. They also showed strong cytotoxicity towards KB and NCI-H187 cell lines (IC50 0.60 - 112.28 nM), as well as the Vero cell line (IC50 1.50 - 46.51 nM).

Bioactive depsidones from the fungus Pilobolus heterosporus.

A new aromatic ester, pilobolusate (1), four new depsidones, pilobolusones A-D (2-5), five known depsidones, (6-10), and ergosterol were isolated from the fungus Pilobolus heterosporus. Their structures were established on the basis of spectroscopic data. Compounds 2 and 4-9 showed cytotoxicity against three cancer cell lines (KB, MCF-7, and NCI-H187) with IC50 values in the range of 9.94-97.42 µM. In addition, compounds 2, 5, 9, and 10 exhibited antimalarial activity against Plasmodium falciparum with IC50 values ranging from 3.67-23.56 µM.

A bioactive triterpenoid and vulpinic acid derivatives from the mushroom Scleroderma citrinum.

A new lanostane-type triterpenoid, (20 S,22 S,23 E)-22- O-acetyl-25-hydroxylanosta-8,23( E)-dien-3-one ( 1), isolated as a new natural product for the first time, methyl 4,4'-dimethoxyvulpinate ( 2), together with the known compound 4,4'-dimethoxyvulpinic acid ( 3) were isolated from the mushroom Scleroderma citrinum. Their structures were determined using spectroscopic and chemical methods, and an X-ray analysis was performed to confirm structure of 1. Compound 1 exhibited significant antiviral activity against Herpes simplex type 1. Compound 3 and two of its derivatives, the dibromo derivative 5 and acetate derivative 6, exhibited activity towards Mycobacterium tuberculosis. In addition, 5 and 6 also showed cytotoxicity against the NCI-H187 cell line.

Antimycobacterial anthraquinone-chromanone compound and diketopiperazine alkaloid from the fungus Chaetomium globosum KMITL-N0802.

Investigation of the fungus Chaetomium globosum KMITL-N0802 led to the isolation of a novel anthraquinone-chromanone compound named chaetomanone along with seven known compounds, ergosterol, ergosteryl palmitate, chrysophanol, chaetoglobosin C, alternariol monomethyl ether, echinuline and isochaetoglobosin D. These compounds were characterized by spectroscopic methods. Chaetomanone and echinulin exhibited activity towards Mycobacterium tuberculosis.