Alkaloids from the Mangrove-Derived Actinomycete Jishengella endophytica 161111

Abstract

A new alkaloid, 2-(furan-2-yl)-6-(2S,3S,4-trihydroxybutyl)pyrazine (1), along with 12 known compounds, 2-(furan-2-yl)-5-(2S,3S,4-trihydroxybutyl)pyrazine (2), (S)-4-isobutyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (3), (S)-4-isopropyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (4), (4S)-4-(2-methylbutyl)-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (5), (S)-4-benzyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (6), flazin (7), perlolyrine (8), 1-hydroxy-β-carboline (9), lumichrome (10), 1H-indole-3-carboxaldehyde (11), 2-hydroxy-1-(1H-indol-3-yl)ethanone (12), and 5-(methoxymethyl)-1H-pyrrole-2-carbaldehyde (13), were isolated and identified from the fermentation broth of an endophytic actinomycetes, Jishengella endophytica 161111. The new structure 1 and the absolute configurations of 2–6 were determined by spectroscopic methods, J-based configuration analysis (JBCA) method, lactone sector rule, and electronic circular dichroism (ECD) calculations. Compounds 8–11 were active against the influenza A virus subtype H1N1 with IC50 and selectivity index (SI) values of 38.3(±1.2)/25.0(±3.6)/39.7(±5.6)/45.9(±2.1) μg/mL and 3.0/16.1/3.1/11.4, respectively. The IC50 and SI values of positive control, ribavirin, were 23.1(±1.7) μg/mL and 32.2, respectively. The results showed that compound 9 could be a promising new hit for anti-H1N1 drugs. The absolute configurations of 2–5, 13C nuclear magnetic resonance (NMR) data and the specific rotations of 3–6 were also reported here for the first time.

Agricultural and Other Biotechnological Applications Resulting from Trophic Plant-Endophyte Interactions

“…Table 4 presents a summary of the most popular bioactive compounds synthesized by endophytic microbiota. Usually, cytotoxic activity [129][130][131] followed by anticancer and antibacterial activities [132][133][134], antiviral effects [135], and protective impact against pathogens [134] were detected. Many such cases have been documented in literature older than from the last two years are included in Table 4.…”

“…De Melo et al [138] isolated bacterial endophytes that belonged to the Bacillus genus. B. pumilus MAIIIM4a exhibited strong inhibitory activity against the fungi Rhizoctonia solani, Pythium aphanidermatum, and Sclerotium rolfsii [135]. After LC/MS analysis, it appeared that B. pumilus MAIIIM4a produced an antifungal compound, which was identified as pumilacidin [138].…”

Cyclopeptides from marine actinomycete Streptomyces sp. G261

“…This observation strongly suggested that the leucine unit of 1 was replaced by the 4hydroxyphenylanaline moiety in 5. Comparison with the literature, [10][11][12] compound 5 was identified as Cyclo-(Pro-Tyr). This cyclodipeptide had antibacterial activity against both Gram-positive and Gram-negative bacteria and antifungal property.…”

Antioxidant and Antiglycation Activity of Rhizosphere and Endophytic Actinobacteria of Xylocarpus granatum

“…The alkaloids appear to offer the considerable promise for further investigation as anti-inflammatory compounds, and some appears to be remarkably active (Filho et al, 2006). Alkaloid compounds isolated from Jishengella endophytica 16111, an endophytic organism from X. granatum, have antiviral activity (Wang et al, 2014). Flavonoids possess many biochemical properties, but the best described property of almost every group of flavonoids is their capacity to act as antioxidants.…”