Arthpyrones A–C, Pyridone Alkaloids from a Sponge-Derived Fungus Arthrinium arundinis ZSDS1-F3

Abstract

Three new 4-hydroxy-2-pyridone alkaloids, arthpyrones A-C (1-3), were isolated from the sponge-derived fungus Arthrinium arundinis ZSDS1-F3. Their structures were elucidated on the basis of spectroscopic analysis, CD spectra, quantum chemical calculation, and X-ray single-crystal diffraction analysis. Compounds 1 and 2 possessed a 2-pyridone core featured with a decalin moiety linked via a carboxide bridge bearing a novel oxabicyclo[3.3.1]nonane ring system rarely discovered in nature. A possible biosynthetic pathway for them was proposed.

Deciphering the regulatory and catalytic mechanisms of an unusual SAM-dependent enzyme

“…[4][5][6][7] Pyridone alkaloids (e.g., PF1140, leporins, and fusaricides) are present in numerous fungi, displaying diverse biological activities and applied for various pharmaceutical purposes. 8,9 Owing to the complexity of pyridone alkaloids with a chiral center and pure forms, the efficient synthesis of these compounds has drawn increasing attention from chemists and biochemists. [10][11][12][13][14] Pericyclic reactions are facile access to obtain various biomolecules including some pyridone alkaloids and have been considered as a key transformational process in the biosynthesis of many natural compounds.…”

Perylenequione Derivatives with Anticancer Activities Isolated from the Marine Sponge-Derived Fungus, Alternaria sp. SCSIO41014

“…Sponge-derived fungi are one of the richest sources of many structurally unique and biologically active secondary metabolites among marine sources [8]. As part of our ongoing research for bioactive natural products from sponge-derived fungi [9,10,11,12,13], the fungus Alternaria sp. SCSIO41014 was studied.…”

One Strain-Many Compounds Method for Production of Polyketide Metabolites Using the Sponge-Derived Fungus Arthrinium arundinis ZSDS1-F3

“…A. arundinis ZSDS1-F3 was incubated on a rotary shaker at 28qC for 12 days in a liquid medium previously. Detailed chemical investigation resulted in the isolation of cytotoxic pyridine alkaloids arthpyrones A-C [4], cytochalasins arthriniumnins A-D [5], naphthalene derivative 1,8-dihydroxynaphthol-1-O-D-L-rhamnopyranoside, and some known xanthones [6]. Based on the potential biosynthetic ability of this strain, the OSMAC (one strain-many compounds) approach was carried out to find new compounds.…”

“…Detailed chemical investigation resulted in the isolation of a new natural product, phenethyl 5-hydroxy-4-oxohexanoate (1), which had been previously obtained by natural product biosynthesis [10] (4) [11], decarboxycitrinone (5) [12], and altechromone A (6) [13]. Their cytotoxic activities against the K562, MCF-7, HeLa, DU145, U937, H1975, SGC-7901, A549, MOLT-4, and HL60 cell lines were examined.…”

“…This is the first report of phenethyl 5-hydroxy-4-oxohexanoate (1) as a natural product. (4), decarboxycitrinone (5), and altechromone A (6), were also isolated and identified using their NMR and MS data and comparing their experimental data with those reported in the literature. This is the first report deducing the absolute configuration of compound 2 as 3R, 4S and confirming it by X-ray diffraction analysis.…”