Diverse Secondary Metabolites from the Marine-Derived Fungus Dichotomomyces cejpii F31-1

Abstract

By adding l-tryptophan and l-phenylalanine to GPY medium, twenty-eight compounds, including amides, polyketides, a sesquiterpenoid, a diterpenoid, a meroterpenoid, diketopiperazines, β-carbolines, fumiquinazolines, and indole alkaloids, were discovered from the marine-derived fungus Dichotomomyces cejpii F31-1, demonstrating the tremendous biosynthetic potential of this fungal strain. Among these compounds, four amides dichotomocejs A–D (1–4), one polyketide dichocetide A (5), and two diketopiperazines dichocerazines A–B (15 and 16) are new. The structures of these new compounds were determined by interpreting detailed spectroscopic data as well as calculating optical rotation values and ECD spectra. Obviously, Dichotomomyces cejpii can effectively use an amino acid-directed strategy to enhance the production of nitrogen-containing compounds. Dichotomocej A (1) displayed moderate cytotoxicity against the human rhabdomyosarcoma cell line RD with an IC50 value of 39.1 µM, and pityriacitrin (22) showed moderate cytotoxicity against the human colon carcinoma cell line HCT116 with an IC50 value of 35.1 µM.

Marine-derived fungi as a source of bioactive indole alkaloids with diversified structures

“…Z-4 isolated from the gut of the marine isopod L. oceanica (Wang et al 2015). By adding L-tryptophan and L-phenylalanine to GPY medium, dichotomocej D (400) was discovered from the marine-derived fungus D. cejpii F31-1 (Chen et al 2017). A Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula yielded hermitamide B (401), which exhibited the LD 50 value of 18.0 μmol/L in the brine shrimp bioassay and an IC 50 value of 5.5 μmol/L to Neuro-2a neuroblastoma cells in tissue culture (Tan et al 2000).…”

Nonocarbolines A–E, β-Carboline Antibiotics Produced by the Rare Actinobacterium Nonomuraea sp. from Indonesia

“…According to our literature survey, 1,3-disubstituted β-carboline derivatives bearing a carbonyl moiety at C-1 and a carboxyl group at C-3 are known from plants, sponges, and fungi, while their amide-bearing analogues were reported from plants and bacteria. Of these, we show in Figure 3 stellarine A (6) from the marine-derived fungus Dichotomomyces cejpii F31-1 [26], cestrumine B (7) from the plant Cestrume hediundinum [27], and marinacarboline B (8) from the marine actinobacterium Marinactinospora thermotolerans [13].…”

Recent Advances in the Synthesis of β-Carboline Alkaloids

“…Noctiluca milaris [10] Strychnos johnsonii [11] Lycoris longituba [12] Selaginella delicatula [13] Trichosanthes kirilowii Maxim [14] Rauwolfia caffra [15] Didemnum sp [16] MAO Cnemidocarpa stolonifera [20] apoptosis in PC3 human prostate cancer cell line [20] 8: Eudistoma olivaceum [21] 9: Eudistoma olivaceum [22] 10: Lissoclinum fragile [23] 11: Eudistoma olivaceum [24] 12: analogues of natural products 13: soybean [28] Flindersia laevicarpa [29] 14: analogues of natural products 15: Flindersia Caevicarpa [29] 16: Picrasma quassioides [30] 13: anti-neuroin-flammatory activities [28] 14: n.a. 15: vasorelaxant effect [31] binding affinity to imidazoline I2B receptors [32] 16: cytotoxic activity [33] AMP phosphodiesterase inhibitor [34] anti-inflammatory agent [35,36] trigonostemine [37] 17, 18, 19: Trigonostemone filipes [38] 20: Malassezia furfur [39] Paracoccus marine bacteria [40] Dichotomomyces cejpii [41] 21: Hyrtio erectus [42] Alocasia macrorrhiza [43] 17, 18, 19: cytotoxic activity [44] 20: antiproliferative activity [45] anticancer activity [46,47] 21: antiproliferative activity [48,49] antimalarial activity [46] antiphospholipase A2 [50] and antioxidant activity …”