Trichodermamides D–F, heterocyclic dipeptides with a highly functionalized 1,2-oxazadecaline core isolated from the endophytic fungus Penicillium janthinellum HDN13-309

Abstract

Three new heterocyclic dipeptides with a highly functionalized 1,2-oxazadecaline core, named trichodermamides D-F (1-3), together with the known trichodermamides A-C (4-6), were isolated from the broth of the mangrove-derived endophytic fungus Penicillium janthinellum HDN13-309. The structures were elucidated through extensive NMR spectroscopic and physical data. The absolute configurations of compounds 1-3 were determined by ECD calculations and single-crystal X-ray diffraction experiments. The cytoprotective activities were evaluated on different phase II detoxifying enzymes (SOD2, AKR1C1, HO-1 and NQO1), and compounds 4 and 6 showed potent inducing effects at the concentration of 10 mM.

Secondary metabolites from mangrove-associated fungi: source, chemistry and bioactivities

“…Three new heterocyclic dipeptides, trichodermamides D–F ( 1385–1387 ) with a 1,2-oxazadecaline core, named were identified from the mangrove-derived endophytic fungus Penicillium janthinellum HDN13-309. 496 The absolute configurations of compounds 1385–1387 were assigned by ECD calculations and single-crystal X-ray diffraction experiments. 496 …”

Mangrove-Associated Fungi: A Novel Source of Potential Anticancer Compounds

“…The new epipolythiodioxopiperazine alkaloids, penicisulfuranols A–C ( 112 – 114 ) ( Figure 7 ), were obtained from Penicillium janthinellum HDN13-309, the mangrove endophytic fungus associated with Sonneratia caseolaris collected from Hainan Province, China. Compounds 112 – 114 showed cytotoxicity against HeLa and HL-60 cell lines, with IC 50 values ranging from 0.1 to 3.9 µM [ 63 ].…”

Secondary Metabolites and Bioactivities of Penicillium sp. Sourced from Mangrove from 2007 to 2020

“…其中对青霉属 真菌 Penicillium citrinum、Penicillium janthinellum、 Penicillium commune、Penicillium brocae 的代谢产物研 究的较为广泛. 例如从桔青霉(P. citrinum)中分离得到 了 13 个代谢产物, 这些代谢产物具有抗菌及细胞毒活 性 [27,[30][31][32][33]52] ; 从微紫青霉(P. janthinellum)中分离得到了 28 个次级代谢产物, 这些代谢产物具有抗菌和细胞毒 活性 [4][5][6][7][64][65][66][67] ; 从 P. brocae 中分离得到了 27 个次级代谢 产物, 这些代谢产物具有抗菌、抗氧化及细胞毒活 性 [43][44][45][46][48][49] ; 从团青霉(P. commune)中分离得到了 10 个 异香豆素类次级代谢产物, 均对 α-葡萄糖苷酶具有较强 的抑制作用 [20] . 1 Alkaloids 1～33 produced by mangrove-derived Penicillium sp.…”

“…C(5) -C(5') 之 间 含 有 醚 桥 的 环 四 肽 5,5'-epoxy-MKN-349A (72) [37] . 从红树植物海桑(S. caseolaris)的 内生真菌 P. janthinellum HDN13-309 的发酵液中分离 得到了 3 个具有高度氧化的 1,2-噁唑烷核的杂环二肽 trichodermamides D～F (73～75) [64] 和 1 个新的杂环二肽 N-methyl-trichodermamide B (76) [66] , 其中化合物 76 对 H 2 O 2 诱导的氧化损伤具有细胞保护作用. 从红树林沉 积物来源的真菌 P. polonicum MCCC3A00951 的培养液 中分离了 1 个新的化合物 7-hydroxy-3,10-dehydrocyclopeptine (77) [19] .…”