Bioactive Metabolites from the Deep-Sea-Derived Fungus Diaporthe longicolla FS429

Abstract

The chemical investigation of a methanol extract of the deep-sea-derived fungus Diaporthe longicolla FS429 led to the isolation of two novel diterpenoids longidiacids A and B (1 and 2), two new polyketides (3 and 4), two new cytochalasin analogues longichalasins A and B (6 and 8) and three known analogues 5, 7, 9. Their structures were elucidated through comprehensive spectroscopic analysis, while the absolute configurations were established by the comparison of the experimental and quantum chemical calculated ECD spectra. The structure of compound 7 was confirmed through X-ray diffraction for the first time. In the bioassays compound 8 exhibited antiproliferative effects against SF-268, with an IC50 value of 16.44 μM. Moreover, compounds 1 and 8 were detected to inhibit 35.4% and 53.5% of enzyme activity of Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB) at a concentration of 50 μM.

Marine natural products

“…199 Lipopeptide epimers 500 and 501 and phthalide glycerol ether 502 were isolated from Cochliobolus lunatus, 200 whilst diterpenoids 503 and 504, polyketides 505 and 506 and cytochalasin analogues 507 and 508 were obtained from Diaporthe longicolla. 201 A simple and effective approach to the determination of relative conguration utilising a liquid crystalline phase, was validated on four known NPs and then used to determine the relative conguration of a thiodiketopiperazine, spiroepicoccin A, isolated from Epicoccum nigrum. The absolute conguration of spiroepicoccin A was also determined as 509 (by X-ray crystallography).…”

“…199 Lipopeptide epimers 500 and 501 and phthalide glycerol ether 502 were isolated from Cochliobolus lunatus , 200 whilst diterpenoids 503 and 504 , polyketides 505 and 506 and cytochalasin analogues 507 and 508 were obtained from Diaporthe longicolla . 201…”

Potential of Secondary Metabolites of Diaporthe Species Associated with Terrestrial and Marine Origins

“…Two novel metabolites, longidiacid A (203) and longichalasin B (204), were isolated from the deep-sea-derived fungus Diaporthe longicolla FS429. These compounds were shown to inhibit 35.4% and 53.3% of the enzyme activity of the Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB), respectively, at a concentration of 50 µM [63]. The new diaporpenoid A (205) and the new diaporpyrone A (206) were isolated from a MeOH extract obtained from cultures of the endophytic mangrove fungus Diaporthe sp.…”

Extremophilic Fungi from Marine Environments: Underexplored Sources of Antitumor, Anti-Infective and Other Biologically Active Agents

“…Numerous potential antitumor agents (some also with antibacterial activity) continue to be isolated and reported from deep-sea-derived fungi collected from the Indian Ocean. The new diterpenoids, longidiacids A (1) and B, polyketides, and the cytochalasin analogs, longichalasins A and B (2), were isolated from the fungus Diaporthe longicolla FS429 [10] obtained from deep-sea sediment collected at a depth of 3000 m. Longidiacid A (1) and longichalasin B (2) inhibited tyrosine phosphatase B in Mycobacterium tuberculosis cells by 35.4% and 53.5%, respectively, and longichalasin B (2) exhibited antiproliferative activity against glioblastoma cells (SF-268) with an IC 50 value of 16.44 µM.…”