Biological active metabolite cyclo (l-Trp-l-Phe) produced by South China Sea sponge Holoxea sp. associated fungus Aspergillus versicolor strain TS08

Abstract

Sponge-associated fungi represent the single most prolific source of novel natural products from marine fungi. Cyclo (L-Trp-L-Phe) exhibits biological functions such as plant growth regulation, moderate cytotoxicity and thus has the application potential in pharmaceutical and agricultural biotechnologies. In this study, a fungal strain TS08 was isolated from sponge Holoxea sp. in the South China Sea and identified as A. versicolor according to its 18S rRNA gene and morphological, physiological, and biochemical characteristics. Meanwhile, cyclo (L-Trp-L-Phe) was found to be produced by A. versicolor strain TS08 mainly in the exponential growth phase. The highest yield of cyclo (L-Trp-L-Phe), 13.24 mg/g (per crude extract of EtOAc), 2.51% of cell dry weigh, was obtained on the tenth day of the fungal cultivation. It was the first time to find the biological active cyclo (L-Trp-L-Phe) in sponge-associated microorganism.

Penicyrones A and B, an epimeric pair of α-pyrone-type polyketides produced by the marine-derived Penicillium sp.

“…[7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] Penicyrones A (1) and B (2) were first obtained as a mixture by HPLC (octadecylsilyl (ODS)) with CH 3 OH-H 2 O (1:1). The mixture showed a clear 1 H NMR spectrum; however, two sets of signals were detected for several carbons in the 13 C NMR spectrum.…”

“…TPU1271 was found to produce various types of secondary metabolites. HPLC separation from a culture broth of strain TPU1271 led to the isolation of an epimeric pair of polyketides containing α-pyrone and the tetrahydrofuran rings, penicyrones A (1) and B (2) (Figure 1), as well as nine known compounds: verrucosidin (3), 7-11 fructigenine A (4), 12,13 verrucofortine (5), 9,12 cyclo-(L-Trp-L-Phe) (6), 14,15 cyclopenol (7), 9,16 cyclopenin (8), 9,17 penipratynolene (9), 18,19 aspterric acid (10) 20 and viridicatol (11) 16,21 (Figure 1). Although the planar structure of penicyrones was found in the SciFinder as a compound in commercial chemical libraries, the stereostructure, spectroscopic data and origin were not available.…”

Antimicrobial activities of secondary metabolites and phylogenetic study of sponge endosymbiotic bacteria, Bacillus sp. at Agatti Island, Lakshadweep Archipelago

“…So far, increasing evidence has demonstrated that most of the sponge-derived natural products come from sponge-associated microorganisms [26] , [7] . Accordingly, the isolation and scale-up cultivation of sponge-associated microbes, which produce the bioactive natural products, may solve the current bottleneck problem of supply limitation [10] . Hence, the present study was carried out to find out the potential lead of endosymbiotic bacteria protection towards the inhibition of multi-drug resistant and emerging fish pathogens in aquatic systems.…”

Assessment of a diketopiperazine, cyclo(Trp-Phe) from Streptomyces griseoplanus SAI-25 against cotton bollworm, Helicoverpa armigera (Lepidoptera: Noctuidae)

“…DKPs have antiviral, antifungal, antibacterial, hypoglycemic, antidepressant, and neuroprotecting properties (Wang et al 2013a). The DKP reported in this study-cyclo(Trp-Phe)-was first isolated from Penicillium sp., (Link) (Kimura et al 1996) and later from a fungal species EF8 (Ding et al 2008), sponge-associated fungi Aspergillus versicolor TS08 (Vuillemin) (Chu et al 2011), and an entomopathogenic nematode associated bacterium, Comamonas testosteroni (Marcus and Talalay) (Nishanth Kumar et al 2014). This is the first report on cyclo(Trp-Phe) in an actinomycete, S. griseoplanus SAI-25.…”