Antimycobacterial Substances from Phaeosphaeria sp BCC8292

Abstract

Eleven substances including naphthalenones, naphthoquinones, unsymmetrical naphthoquinone dimers and a chlorinated diphenyl ether, three of which are new, have been isolated from the fungus Phaeosphaeria sp. The absolute stereochemistry of naphthalenones has been determined by the Mosher and exciton chirality methods. The biological activity of these compounds against Mycobacterium tuberculosis and cytotoxicity against KB, BCA, NCI-H 187 and Vero cell lines were evaluated.

Cyclobotryoxide, a Phytotoxic Metabolite Produced by the Plurivorous Pathogen Neofusicoccum australe

“…Comparison of these and reported data identified 5 and 6 as botryosphaerone D 7 and (3S,4S)-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-1(2H)-naphthalenone. 30 The absolute configuration of botryosphaerone D (5), not previously reported, was also determined. Its ECD spectrum ( Figure 3B) was recorded under the same conditions and compared to that of 6.…”

“…Its ECD spectrum ( Figure 3B) was recorded under the same conditions and compared to that of 6. 30 On the basis of coincident negative and positive Cotton effects at 214, and 239 and 280 nm, 5), together with three other new naphthalenone polyketides, had previously been isolated from N. australe strain ZJ12-1A, a fungus obtained from sterilized root epidermis of Sonneratia apetala in China. This compound did not show any antimicrobial and cytotoxic activities.…”

“…7 Finally, (3S,4S)-3,4,8-trihydroxy-6-methoxy-3,4-dihydro-1(2H)-naphthalenone (6) was reported as a new naphthalenone produced from wooddecaying fungus Phaeosphaeria sp. 30 Cyclobotryoxide was characterized as a new naturally occurring compound belonging to a family of epoxycyclohexenones that have been isolated from bacteria, fungi, higher plants, and mollusks. These compounds have shown interesting biological properties such as antifungal, antibacterial, antitumoral, phytotoxic, and enzyme-inhibitory activities.…”

Antimycobacterial dihydronaphthalenone from the endophytic fungus Nodulisporium sp. of Antidesma ghaesembilla

“…Nodulisporium, a common group of xylariaceous anamorphic fungi (Bills et al, 2012), is known to produce bioactive secondary metabolites such as cytotoxic and antimycobacterial quinones (Pontius et al, 2008), antibiotic naphthalenones (Isaka et al, 2009;Pittayakhajonwut et al, 2008), cytotoxic polyketides (Shiono et al, 2012), antifungal and antibiotic terpenoids , and antimalarial coumarins (Chinworrungsee et al, 2001). Our chemical investigation for bioactive secondary metabolites from the endophytic fungus Nodulisporium sp.…”

Biocatalytic Properties and Structural Analysis of Phloroglucinol Reductases

“…Thel atter are known for the reduction of av ariety of compounds ( Figure S1 in the Supporting Information);h owever,t hey do not share any common substrates with the PGRs. [28,29] In contrast, PGRs are involved in the primary metabolism of bacteria, where they participate in the anaerobic degradation of 1 as acarbon source.Moreover, and in regard to structural comparison within the SDR family, substrate promiscuity and substrate specificity are probably determined by variations in the flexible C-terminal segment. [28,29] In contrast, PGRs are involved in the primary metabolism of bacteria, where they participate in the anaerobic degradation of 1 as acarbon source.Moreover, and in regard to structural comparison within the SDR family, substrate promiscuity and substrate specificity are probably determined by variations in the flexible C-terminal segment.…”