Lithocarpins A–D: four tenellone-macrolide conjugated [4 + 2] hetero-adducts from the deep-sea derived fungus Phomopsis lithocarpus FS508

Abstract

Lithocarpins A–D, four novel tenellone-macrolide conjugated dimers containing a fascinating 9,14-epoxynaphtho[2,3-e]oxecin-3(2H)-one skeleton.

Highly Substituted Phenol Derivatives with Nitric Oxide Inhibitory Activities from the Deep-Sea-Derived Fungus Trichobotrys effuse FS524

“…In summary, six new highly substituted phenol derivatives, trieffusols A-F (1-6), along with eleven known analogs (7)(8)(9)(10)(11)(12)(13)(14)(15)(16), were identified from the deep-sea-derived fungus Trichobotrys effuse FS524. Interestingly, trieffusols A and B share an intriguing 6-6/6/6 tetracyclic ring system with the formation of an unprecedented ploy-substituted 9-phenyl-hexahydroxanthone skeleton, which is often encountered as one of the most ubiquitous and intriguing functional moieties in the pharmaceutical drugs but rarely discovered in natural products.…”

“…Therefore, in-depth chemical research on the MNPs would pave the way to providing potential model structures and precursor drugs for new drug developments. During our continuing research for structurally unique and biologically significant NPs from marine fungi [15][16][17], the fungus strain Trichobotrys effuse FS524, isolated from a sediment sample collecting at the South China Sea, attracted our attention, and chemical investigation of the strain resulted in the isolation of six new highly substituted phenol derivatives, trieffusols A-F (1-6), along with eleven known analogues ( Figure 1), including phomalone (7) [18], 2,4-dihydroxy-3-(2-hydroxyethyl)-6-methoxyphenyl)-3-hydroxybutan-1-one (8) [18], (E)-1-(2,4-dihydroxy-3-(2-hydroxyethyl)-6-methoxyphenyl)but-2-en-1-one (9) [18], deoxyphomalone (10) [18], phomalichenone A (11) [18], methylindole-3-acetate (12) [19], 3-indole acetic acid (13) [20], 4-methoxyphenylacetic acid (14) [21], papuline (15) [22], and stigmast-4-en-3-one (16) [23]. Furthermore, their structures with absolute configurations were successfully established with the aid of spectroscopic data analyses, single-crystal X-ray diffraction experiments, and ECD calculations.…”

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

“…Our group has focused on the discovery of bioactive secondary metabolites from deep-sea-derived fungi for over ten years. In our previous study, a number of bioactive compounds with unprecedented skeletons were discovered in deep-sea-fungi from the South China Sea and Indian Ocean, such as the highly oxygenated tenellone-macrolide conjugated dimers lithocarpins A–D [ 9 ] and multi-cyclic meroterpenoids phomeroids A and B [ 10 ], both of which displayed significant cytotoxicity against human cancer cell lines. In this study, the chemical and biological investigation of a deep-sea-derived fungus Diaporthe longicolla FS429 was carried out and six new secondary metabolites (compounds 1 – 4 , 6 and 8 ) together with three known compounds 5 , 7 , 9 were isolated ( Figure 1 ).…”

Highly Substituted Benzophenone Aldehydes and Eremophilane Derivatives from the Deep-Sea Derived Fungus Phomopsis lithocarpus FS508

“…Motivated by an ongoing research program focusing on biologically meaningful natural products with novel structural diversity and architectural complexity from the marine-derived fungi, numerous new compounds with cytotoxic and enzyme inhibitory activities were obtained, including lithocarpins, dichotocejpins, eutypellols and acaromycin [ 20 , 21 , 22 , 23 , 24 ]. Recently, a continuing investigation of Phomopsis lithocarpus FS508, which was isolated from the sediment sample of the India Ocean, led to obtain five new benzophenone derivatives with a rare naturally occurring aldehyde functionality named tenellones D–H ( 1 – 5 ) as well as a new eremophilane derivative lithocarin A ( 7 ), together with two related known compounds tenellone A [ 25 ] and AA03390 [ 26 ] ( Figure 1 ).…”