Three nitrogen-containing metabolites from an algicolous isolate of Trichoderma asperellum

Abstract

As one of the most productive species, Trichoderma asperellum, especially isolated from marine algae, has contributed a number of new terpenes and nitrogen-bearing compounds, encouraging our continuous efforts to further explore them. Consequently, three new nitrogen-containing secondary metabolites, including cyclo(L-5-MeO-Pro-L-5-MeO-Pro) (1), 5′-acetoxy-deoxycyclonerin B (2), and 5′-acetoxy-deoxycyclonerin D (3) were isolated from the marine alga-derived endophytic fungus Trichoderma asperellum A-YMD-9-2. Their structures and relative configurations were fully elucidated through spectroscopic techniques, mainly including 1D/2D NMR and MS. The absolute configurations of 1 and 2 were ascertained on the basis of X-ray diffraction (Cu Kα radiation) and ECD data, respectively. The isolation of these new nitrogen-bearing compounds adds to the structural diversity of marine algicolous Trichoderma spp., and they display potent inhibition against some marine phytoplankton species.

Trichoderma: A Treasure House of Structurally Diverse Secondary Metabolites With Medicinal Importance

“…Dehydroxymethylbis(dethio)bis(methylthio)gliotoxin ( 131) and (3S,6R)-6-(para-hydroxybenzyl)-1,4-dimethyl-3,6-bis(methylthio)piperazine-2,5-dione (132), which were structurally characterized as two undescribed sulfurated diketopiperazines, were produced by an algicolous isolate of T. virens Y13-3 (Shi et al, 2018b). The fungal strain T. asperellum A-YMD-9-2 from Gracilaria verrucosa produced an undescribed symmetric diketopiperazine, cyclo(L-5-MeO-Pro-L-5-MeO-Pro) (133) (Song et al, 2020).…”

“…141 was the first example of a 3-amino-5-hydroxy-5-vinyl-2cyclopenten-1-one dimer. Two nitrogen-containing cyclonerane sesquiterpene derivatives, 5 -acetoxy-deoxycyclonerin B ( 142) and 5 -acetoxy-deoxycyclonerin D (143), were obtained from the marine fungus T. asperellum A-YMD-9-2 (Song et al, 2020).…”

Acremocholone, an Anti‐Vibrio Steroid from the Marine Mesophotic Zone Ciocalypta Sponge‐Associated Fungus Acremonium sp. NBUF150

“…Many studies have supported the long‐standing hypothesis that symbiotic microorganisms are the real producers of many compounds reported previously from marine invertebrate [15–18] . Long evolutionary connections have led to some sharing of biosynthesis genes between symbionts and their host invertebrates, including sponges [19–21] …”

“…[15 -18] Long evolutionary connections have led to some sharing of biosynthesis genes between symbionts and their host invertebrates, including sponges. [19][20][21] A mesophotic coral ecosystem is a marine ecosystem that is light dependent, typically 30 to 150 m deep. MCEs provide up to 80 % of prospective coral reef ecosystems globally but relatively less research has focused on them compared to shallow reefs.…”

Structures and Biological Activities of Diketopiperazines from Marine Organisms: A Review

“…One new DKP namely cyclo(L-5-MeO-Pro-L-5-MeO-Pro) ( 220 ) was isolated from the fungus Trichoderma asperellum A-YMD-9-2, which was obtained from marine macroalga Gracilaria verrucose collected from Yangma Island. Compound 220 exhibited inhibitory activities against Chattonella marina , Heterosigma akashiwo , Karlodinium veneficum and Prorocentrum donghaiense with the EC 50 values of 47.3, 276, 327 and 351 μM, respectively [ 104 ]. Three novel sulfur-containing DKPs namely pretrichodermamides D–F ( 221–223 ) were separated from the fungus Penicillium sp.…”