Hirsutide, a cyclic tetrapeptide from a spider-derived entomopathogenic fungus, Hirsutella sp

The entomopathogenic fungus Hirsutella sp., isolated from an infected spider, was found to produce the new cyclotetrapeptide hirsutide (1), cyclo-(L-NMe-Phe-L-Phe-L-NMe-Phe-L-Val), along with the known cytochalasin Q (2), using a cytotoxicity-guided isolation procedure. The structure of 1 was elucidated using one- and two-dimensional NMR experiments, mass spectrometry, and Marfey's method for analyzing the configuration of the amino acids.     

A cytotoxic xanthone dimer from the entomopathogenic fungus Aschersonia sp. BCC 8401

Ascherxanthone A (1), a novel symmetrical tetrahydroxanthone dimer, was isolated from the entomopathogenic fungus Aschersonia sp. BCC 8401. The structure of 1 was elucidated by spectroscopic analysis, especially 2D-NMR. Compound 1 exhibited activity against Plasmodium falciparum K1 with an IC(50) value of 0.20 microg/mL, but it also showed cytotoxic activities against Vero cells and three tumor cell lines.     

Lanostane and hopane triterpenes from the entomopathogenic fungus Hypocrella sp. BCC 14524

Seven new lanostane-type triterpenes, hypocrellols A-G (1-7), and six new hopane-type triterpenes, 7β,15α-dihydroxy-22(29)-hopene (8), 3β,7β-dihydroxy-22(29)-hopene (9), 3β-acetoxy-15α-hydroxy-22(29)-hopene (10), 3β,7β,15α,22-tetrahydroxyhopane (11), 3β-acetoxy-7β,15α,22-trihydroxyhopane (12), and 7β,15α,22-trihydroxyhopane (13), were isolated from the scale insect pathogenic fungus Hypocrella sp. BCC 14524. The structures of the new compounds were elucidated by analyses of the NMR spectroscopic and mass spectrometry data. The structure of 1 was confirmed by X-ray crystallography.     

Cyclohexadepsipeptides from the insect pathogenic fungus Hirsutella nivea BCC 2594

Two new cyclohexadepsipeptides, hirsutatins A (1) and B (2), were isolated from a culture filtrate of the insect pathogenic fungus Hirsutella nivea BCC 2594. Structures of these compounds were elucidated primarily by NMR and mass spectroscopic analyses. The alpha-carbon stereochemistry of 1 was established by HPLC analysis of its acid hydrolysate using a chiral column. Hirsutatin B (2) exhibited activity against the malarial parasite Plasmodium falciparum K1 with an IC50 value of 5.8 microg/mL, while hirsutatin A (1) was inactive at a concentration of 20 microg/mL.     

Phenolic glycosides from the filamentous fungus Acremonium sp. BCC 14080

New phenolic mono- and digalactopyranosides (1 and 2), their aglycone KS-501a (3), and a new phenolic 4-O-methylglucopyranoside (4) were isolated from the filamentous fungus Acremonium sp. BCC 14080. Structures of these compounds were elucidated by extensive MS and NMR spectroscopic analyses. Compound 1 displayed anti-HSV-1 activity with an IC(50) value of 7.2 microM. Compound 3 exhibited activity against Plasmodium falciparum K1 with an IC(50) value of 9.9 microM.     

Chromone derivatives from the filamentous fungus Lachnum sp. BCC 2424

Five new chromones, named lachnones A-E (1-5), were isolated from the filamentous fungus Lachnum sp. BCC 2424 along with known (2E,6S)-2,6-dimethyl-2,7-octadiene-1,6-diol. Their structures were elucidated by spectroscopic methods. Lachnones B (2) and D (4) mildly inhibited the growth of Mycobacterium tuberculosis, both with MIC values of 200 microg/mL.     

Hirsutellide A,a new antimycobacterial cyclohexadepsipeptide from the entomopathogenic fungus Hirsutella kobayasii

A new cyclohexadepsipeptide, named hirsutellide A (1), was isolated from a cell extract of the entomopathogenic fungus Hirsutella kobayasii BCC 1660. The structure of 1 was elucidated by analyses of spectroscopic data, and its absolute stereochemistry was addressed by the use of Marfey's method. Hirsutellide A (1) exhibited antimycobacterial and antimalarial activities, but was inactive toward the Vero cell line (at 50 microg/mL).     

A cyclopeptide from the Insect pathogenic fungus Cordyceps sp. BCC 1788

A new cycloheptapeptide, cordyheptapeptide A (1), was isolated from the insect pathogenic fungus Cordyceps sp. BCC 1788 along with four known bioxanthracenes (2-5). The structure was elucidated by spectroscopic data. The absolute configuration of amino acid residues was determined by HPLC and X-ray diffraction analyses.     

Aurocitrin and related polyketide metabolites from the wood-decay fungus Hypocrea sp. BCC 14122

The known gentisaldehyde antibiotic aurocitrin (1), its cis-olefinic isomer (2), a salicylaldehyde analogue (3), two new benzofuran derivatives (4 and 5), and a new dihydroisocoumarin (6) were isolated from the wood-decay fungus Hypocrea sp. BCC 14122. The structures were elucidated primarily by NMR and mass spectroscopic analyses.     

Pyridone and tetramic acid alkaloids from the spider pathogenic fungus Torrubiella sp. BCC 2165

Torrubiellones A-D (1-4), new pyridone and tetramic acid alkaloids, were isolated from the spider pathogenic fungus Torrubiella sp. BCC 2165. Torrubiellone A (1) exhibited antimalarial activity with an IC(50) value of 8.1 μM, while it showed very weak cytotoxic activity.     

Paecilodepsipeptide A, an antimalarial and antitumor Cyclohexadepsipeptide from the insect pathogenic fungus Paecilomyces cinnamomeus BCC 9616

Paecilodepsipeptide A (1), a new cyclohexadepsipeptide possessing three d-amino acid residues, together with its linear analogues paecilodepsipeptides B (2) and C (3), was isolated from the insect pathogenic fungus Paecilomyces cinnamomeus BCC 9616. Structures of these compounds were elucidated primarily by NMR and mass spectroscopic analyses. The absolute configurations of the amino acid and hydroxy acid residues of 1 were addressed by HPLC analysis of its acid hydrolyzate using a chiral column and Marfey's method. Paecilodepsipeptide A (1) showed activity against the malarial parasite Plasmodium falciparum K1 with an IC50 value of 4.9 microM. This compound also showed cytotoxicity to two cancer cell lines, KB (IC50 5.9 microM) and BC (IC50 6.6 microM); however, it was inactive against noncancerous Vero cells up to 67 microM (50 microg/mL).     

Depsidones from the endophytic fungus BCC 8616

Three new depsidones (1-3) have been isolated from the endophytic fungus BCC 8616 and their structures analyzed on the basis of spectroscopic data interpretation. Compound 1 exhibited weak cytotoxic activity against breast and epidermoid carcinoma cell lines.     

Hirsutane sesquiterpenes from the fungus Lentinus connatus BCC 8996

Two new hirsutane sesquiterpenes, connatusins A (1) and B (2), were isolated from the fungus Lentinus connatus BCC 8996. The structures, closely related to hypnophilin, were elucidated on the basis of the spectroscopic data. An X-ray analysis was performed to confirm the structure of 1. Six known compounds were also obtained. Panepoxydone (5), panepoxydione (6), and dihydrohypnophilin (8) exhibited significant antimalarial and cytotoxic activities.     

Aurovertins F-H from the entomopathogenic fungus Metarhizium anisopliae

Analysis of fermentation broth of the entomopathogenic fungus Metarhizium anisopliae has led to isolation of aurovertin D ( 1) and three new aurovertin-type metabolites, aurovertin F ( 2), aurovertin G ( 3), and aurovertin H ( 4). Their structures were determined on the basis of spectroscopic analyses and chemical conversions.     

ES-242 derivatives and cycloheptapeptides from Cordyceps sp. strains BCC 16173 and BCC 16176

Five new ES-242 analogues ( 1- 5) were isolated together with nine known compounds ( 6- 14) from the insect pathogenic fungus Cordyceps sp. BCC 16173. A closely related strain, BCC 16176, provided cordyheptapeptide A ( 15) and small amount of its new analogue, cordyheptapeptide B ( 16), along with known ES-242s. Structures of the new bioxanthracenes, 1- 5, were determined to be 6'- O-desmethyl analogues of 6 (ES-242-4), 8, 9 (ES-242-2), 12, and 13, respectively, primarily by spectroscopic analyses. Cordyheptapeptide B ( 16) has an N-methyl- l-phenylalanine residue instead of the N-methyl- l-tyrosine in 15.     

Bioactive compounds from the seed fungus Menisporopsis theobromae BCC 3975

Eight new compounds (2-9), together with a known dithiodiketopiperazine (1), were isolated from the seed fungus Menisporopsis theobromae BCC 3975. The structures of these substances were elucidated by analyses of spectroscopic data. Compounds 1 and 4 exhibited moderate cytotoxicity against BC-1 cell lines with IC50 values of 29.2 and 57.4 microM, respectively. Cytotoxicity of 1, 2, 4, and 9 against the NCI-H187 cell line showed respective IC50 values of 22.9, 20.3, 1.8, and 56.6 microM. Compounds 2 and 4 exhibited antimalarial activity with IC50 values of 2.95 and 28.8 microM, respectively. Substances 1, 4, 7, 8, and 9 possessed weak antimycobacterial activity (MIC 154.8-952.3 microM), while compounds 2 and 3 showed potent antimycobacterial activity with respective MIC values of 1.24 and 7.14 microM.     

A xanthocillin-like alkaloid from the insect pathogenic fungus Cordyceps brunnearubra BCC 1395

Cordyformamide (4), the plausible biogenetic precursor of xanthocillin Y2, was isolated from a culture broth of the insect pathogenic fungus Cordyceps brunnearubra BCC 1395. Cordyformamide was found to exhibit activity against the malarial parasite Plasmodium falciparum K1 with an IC50 value of 18 microM, whereas it showed weak or no cytotoxicity.     

10-membered macrolides from the insect pathogenic fungus Cordyceps militaris BCC 2816

Three new 10-membered macrolides (1-3) have been isolated from the entomopathogenic fungus Cordyceps militaris BCC 2816, together with six known compounds, cepharosporolides C (4), E (5), and F (6), 2-carboxymethyl-4-(3'-hydroxybutyl)furan (7), cordycepin (8), and pyridine-2,6-dicarboxylic acid. The structures were determined by analysis of NMR data, and an X-ray analysis was performed to confirm the structure of 1. The antimalarial activity of 1-4 and 8 against Plasmodium falciparum K1 was evaluated.     

Bioactive compounds from the scale insect pathogenic fungus Conoideocrella tenuis BCC 18627

A new cyclohexadepsipeptide, conoideocrellide A (1), its linear derivatives, conoideocrellides B-D (2-4), three new hopane triterpenoids (5-7), two new bioxanthracenes (9 and 10), and a new isocoumarin glycoside (13) were isolated from the scale insect pathogenic fungus Conoideocrella tenuis BCC 18627. Biological activities of the new compounds were evaluated.     

Isariotins A-D, alkaloids from the insect pathogenic fungus Isaria tenuipes BCC 7831

Isariotins A-D (1- 4), alkaloids possessing a unique bicyclo[3.3.1]nonane ring, were isolated from the insect pathogenic fungus Isaria tenuipes BCC 7831. The structures of these compounds were elucidated primarily by NMR and mass spectroscopic analyses.