Seven New Drimane-Type Sesquiterpenoids from a Marine-Derived Fungus Paraconiothyrium sporulosum YK-03

Abstract

Seven new drimane-type sesquiterpenoids, namely the sporulositols A–D (1–4), 6-hydroxydiaporol (5), seco-sporulositol (6) and sporuloside (7) were isolated from the ethyl acetate extract of fermentation broth for a marine-derived fungus Paraconiothyrium sporulosum YK-03. Their structures were elucidated by analysis of extensive spectroscopic data, and the absolute configurations were established by crystal X-ray diffraction analysis and comparisons of circular dichroism data. Among them, sporulositols A–E (1–4) and seco-sporulositol (6) represent the first five examples of a unique class of drimanic mannitol derivatives, while compounds 6 and 7 may represent two new series of natural drimanes, possessing an aromatic ring with a rare 4,5-secodrimanic skeleton and an unusual CH3-15 rearranged drimanic α-D-glucopyranside, respectively. Furthermore, the origin of mannitol moiety was investigated by reliable HPLC and NMR analyses.

Chemical Diversity and Biosynthesis of Drimane‐Type Sesquiterpenes in the Fungal Kingdom

“…Different from the large chemical variety of DTS‐esters, ethers are usually formed at C‐11 (Figure 4). Reported examples include sporulositols ( 106 – 109 ), isolated from Paraconiothyrium sporulosum , containing a D‐mannitol group [45] . Other relevant ethers are cryptoporic acids ( 110 – 112 ), with an isocitric acid moiety, initially isolated from C. volvatus [46] .…”

A Review of Terpenes from Marine-Derived Fungi: 2015–2019

“…Asperienes A-D (35)(36)(37)(38), two pairs of C-6/C-7 epimeric drimane sesquiterpene esters, were successfully isolated for the first time from the marine sediment fungus Aspergillus flavus CF13-11. All displayed significant cytotoxic activities against HeLa, MCF-7, MGC-803, and A549 cell lines, with the IC 50 values ranging from 1.4 to 8.3 µM (with cisplatin as p.c.)…”

“…Seven new drimane-type sesquiterpenoids, sporulositols A-D (108-111), 6-hydro-xydiaporol (112), seco-sporulositol (113), and sporuloside (114), were later found in the sea mud-derived fungus Paraconiothyrium sporulosum YK-03 collected from the intertidal zone of Bohai Bay in Liaoning Province [35]. Structurally, compounds 108-111 and 113 represent the first five examples of a unique class of drimanic mannitol derivatives, while compounds 113 and 114 might belong to two new series of natural drimanes possessing an aromatic ring with a rare 4,5-secodrimanic skeleton and an unusual CH 3 -15 rearranged drimanic α-d-glucopyranside, respectively [35]. Compounds 108-114 did not show any detectable cytotoxicity against the two tested cell lines A549 and MCF-7 [35].…”

“…Structurally, compounds 108-111 and 113 represent the first five examples of a unique class of drimanic mannitol derivatives, while compounds 113 and 114 might belong to two new series of natural drimanes possessing an aromatic ring with a rare 4,5-secodrimanic skeleton and an unusual CH 3 -15 rearranged drimanic α-d-glucopyranside, respectively [35]. Compounds 108-114 did not show any detectable cytotoxicity against the two tested cell lines A549 and MCF-7 [35].…”

“…Penicillium (75, 45.5%) and Aspergillus (33, 20.0%) were the principal sources of marine meroterpenoids, though they were also found in 10 other genera of marine fungi (Alternaria, Eupenicillium, Lophiostoma, Mucor, Myrothecium, Neosartorya, Pestalotiopsis, Pleosporales, Stachybotrys, and Talaromyces). These fungi were mainly isolated from living matter (125, 75.8%), such as marine animals (66, 40.0%) and aquatic plants (59,35.8%), and to a lesser extent, living environments (35, 21.2%, mainly marine sediments). The most important specific source of fungi was algae (31), followed by sponges (24), mangrove habitats (23), other marine sediments (18), deep-sea sediments (11), mollusks (12), and sea worms (11).…”