Abstract
Six new prenylated indole diketopiperazine alkaloids, asperthrins A–F (1–6), along with eight known analogues (7–14), were isolated from the marine-derived endophytic fungus Aspergillus sp. YJ191021. Their planar structures and absolute configurations were elucidated by HR-ESI-MS, 1D/2D NMR data, and time-dependent density functional theory (TDDFT)/ECD calculation. The isolated compounds were assayed for their inhibition against three agricultural pathogenic fungi, four fish pathogenic bacteria, and two agricultural pathogenic bacteria. Compound 1 exhibited moderate antifungal and antibacterial activities against Vibrio anguillarum, Xanthomonas oryzae pv. Oryzicola, and Rhizoctonia solani with minimal inhibitory concentration (MIC) values of 8, 12.5, and 25 μg/mL, respectively. Furthermore, 1 displayed notable anti-inflammatory activity with IC50 value of 1.46 ± 0.21 μM in Propionibacterium acnes induced human monocyte cell line (THP-1).
Highlights
Endophytic fungi refer to microorganisms that spend their entire or part of their life cycle in plant tissues, animals, and environments without causing any obvious infection or visible disease to the host [1]
Prenylated indole alkaloids have been reported to show a wide array of biological activities including antimicrobial, insecticidal, and cytotoxic activities [14,15]
The fascinating structural and biological properties of prenylated indole alkaloids make it possible for them to be developed into our armor and weaponry: Natural agrochemicals and drugs
Summary
Endophytic fungi refer to microorganisms that spend their entire or part of their life cycle in plant tissues, animals, and environments without causing any obvious infection or visible disease to the host [1]. Diketopiperazine alkaloids are valued for their properties and functions in fungal self-biology, and for niche establishment to defend abiotic and biotic stress in nature. They are cyclodipeptides formed by condensation of two amino acids under the control of NRPS genes [10], especially those isolated from the genera Aspergillus and Penicillium [11]. Among them, those derived from tryptophan and proline are the most popular types in the current study, especially in structural diversity, chemical synthesis, and pharmacological activity [12,13,14]. The fascinating structural and biological properties of prenylated indole alkaloids make it possible for them to be developed into our armor and weaponry: Natural agrochemicals and drugs
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