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

Abstract

Marine-derived fungi are a significant source of pharmacologically active metabolites with interesting structural properties, especially terpenoids with biological and chemical diversity. In the past five years, there has been a tremendous increase in the rate of new terpenoids from marine-derived fungi being discovered. In this updated review, we examine the chemical structures and bioactive properties of new terpenes from marine-derived fungi, and the biodiversity of these fungi from 2015 to 2019. A total of 140 research papers describing 471 new terpenoids of six groups (monoterpenes, sesquiterpenes, diterpenes, sesterterpenes, triterpenes, and meroterpenes) from 133 marine fungal strains belonging to 34 genera were included. Among them, sesquiterpenes, meroterpenes, and diterpenes comprise the largest proportions of terpenes, and the fungi genera of Penicillium, Aspergillus, and Trichoderma are the dominant producers of terpenoids. The majority of the marine-derived fungi are isolated from live marine matter: marine animals and aquatic plants (including mangrove plants and algae). Moreover, many terpenoids display various bioactivities, including cytotoxicity, antibacterial activity, lethal toxicity, anti-inflammatory activity, enzyme inhibitor activity, etc. In our opinion, the chemical diversity and biological activities of these novel terpenoids will provide medical and chemical researchers with a plenty variety of promising lead compounds for the development of marine drugs.

Secondary Metabolites with Nitric Oxide Inhibition from Marine-Derived Fungus Alternaria sp. 5102

“…The 1 H NMR spectrum ( Figure S2) (Table 1) along with the HSQC experiment showed three aromatic protons owing to a 1,2,3-trisubstituted aromatic ring [δ H 7.56 (1H, t, J = 7.9 Hz); 6.96 (1H, dd, J = 2.5, 7.3 Hz); 6.96 (1H, dd, J = 2.5, 7.3 Hz)], three methines [δ H 5.90 (1H ,t, J = 6.6 Hz); 4.86 (1H, m); 3.73 (1H, m);], one methylene [δ H 2.95 (2H, m)], and two methyls [1.25 (3H, d, J = 6.4 Hz); 1.18 (3H, d, J = 6.4 Hz)]. The 13 C NMR ( Figure S3) and HSQC data ( Figure S4) of 1 indicated the presence of 14 carbons for eight sp 2 hybridized carbons including two ester carbonyls (δ C 171.5, 168.8) and six sp 3 A 7-hydroxybenzofuran was assigned by 1 H-1 H COSY correlations ( Figure S5) between H-4 and H-5, H-5 and H-6, H-6 and H-7, and HMBC correlations ( Figure S6) from H-4 to C-3a and C-7a, and H-3 to ester carbonyl C-1, as well as four-bond W-type correlation from H-6 to ester carbonyl C-1 ( Figure 2). The HMBC correlations from H-8 to C-3 and H-3 to C-9 indicated that C-8 of acetoxy was linked to C-3 of 7-hydroxy-benzofuran group.…”

“…Marine-derived fungi are a significant source of pharmacological molecules with interesting and diversified structural properties [1][2][3][4]. Among them, the fungal genus Alternaria had a widespread distribution in marine source [4] (including sediment [5], sponge [6], alga [7], mangrove [8], soft coral [9]) and could produce plenty of structural molecules, including nitrogen-containing compounds, steroids, terpenoids, pyranones, quinones, and phenolics [10].…”

Genome Mining for Antimicrobial Compounds in Wild Marine Animals-Associated Enterococci

“…In addition to bacteriocins, a wide variety of novel gene clusters encoding putative terpenes, NRPs, polyketides, and other active compounds have been uncovered by in silico analysis, creating new opportunities for drug development [23,24,49,79]. NRPs and terpenes have been reported with activity against several antibiotic-resistant strains [80][81][82][83][84][85]. A small library of predicted NRP peptides was chemically synthesized, based on the primary sequence of NRP clusters in the human microbiome, and a potent anti-MRSA (methicillin-resistant Staphylococcus aureus) peptide with a new mechanism of action, named humimycin, was identified [80].…”

Molecular methods unravel the biosynthetic potential of Trichoderma species

“…are reported to produce many terpenes, their responsible biosynthetic gene clusters in Trichoderma have been under-investigated. 53,82,103,104 T. viride J1-030 was mined for terpene cyclases, one of which, named Tvi09626, was expressed in an FPP-overproducing strain of S. cerevisiae. This produced a new 5/6 bicyclic brasilane-type sesquiterpene 72 (Scheme 5).…”