Structure and Absolute Configuration of Aspergilumamide A, a Novel Lumazine Peptide from the Mangrove‐Derived Fungus Aspergillus sp.

Abstract

A novel lumazine peptide, aspergilumamide A (1), as well as a known analog penilumamide (2), were isolated from the mycelia of a marine‐derived fungus Aspergillus sp. (33241), obtained from the mangrove Bruguiera sexangula var. rhynchopetala collected from the South China Sea. The structure of 1 was identified by comprehensive spectroscopic analysis, including 1D‐ and 2D‐NMR, ESI‐MS, and MS/MS experiments. The absolute configuration of 1 was determined by Marfey's method.

Dihydroisocoumarins from the Mangrove-Derived Fungus Penicillium citrinum

“…These results have drawn the attention of both pharmaceutical and natural product chemists. In our search for new bioactive natural products from marine fungi in the South China Sea, we have found several bioactive compounds, including anthraquinone derivatives, cytochalasins, lumazine peptides, benzopyrans, stemphol sulfates, triterpenes, and α -pyrone derivatives [7,8,9,10,11,12,13]. Our previous investigation on the endophytic fungus Penicillium citrinum has resulted in the discovery of one new benzopyran derivative (2 R *,4 R *)-3,4-dihydro-5-methoxy-2-methyl-2H-1-benzopyran-4-ol [10].…”

Recent Discovery of Heterocyclic Alkaloids from Marine-Derived Aspergillus Species

“…These seven heterocyclic alkaloids were characterized as new pyrazinone alkaloids. The structures of compounds 125-127 were characterized as three open-chain peptides with an unusual skeleton of 1,3-dimethyllumazine-6-carboxylic acid, coupled to glutamine and anthranilic acid methyl ester [68,69]. In contrast, compound 125 was isolated from a culture of the mangrove-derived fungal strain A. sp.…”

“…In contrast, compound 125 was isolated from a culture of the mangrove-derived fungal strain A. sp. (33241) [68], while compounds 126 and 127 were obtained from cultures of the marine sediment-derived fungal strain A. terreus FA009 [69]. Compound 128 was identified as a novel oxadiazin derivative and it was also isolated from a coculture of the marine gorgonian-derived P. citrinum SCSGAF 0052 and A. sclerotiorum [49].…”

“…Moreover, the producing strain of 125 originated from the mangrove Bruguiera sexangula var. rhynchopetala that was collected in the South China Sea [68]. Interestingly, two heterocyclic alkaloids (44 and 45) were isolated from the fungi residing in an unidentified marine organism that was collected in the Ross Sea without any detailed description for species identification [41].…”

“…Figures 1-6 present the structures of newly reported heterocyclic alkaloids (1-130) produced by marine-derived Aspergillus species from 2014 to 2018, in which the nitrogen-containing heterocyclic rings are marked in red. These heterocyclic alkaloids could be classified into six major categories: indole alkaloids , diketopiperazine alkaloids , quinazoline alkaloids (59)(60)(61)(62)(63)(64)(65)(66)(67)(68)(69)(70)(71)(72), pyrrolidine alkaloids , cyclopeptide alkaloids (97-108), and other heterocyclic alkaloids (109-130) based on their structural patterns.…”