Saliniquinones A - F, New Members of the Highly Cytotoxic Anthraquinone-γ-Pyrones from the Marine Actinomycete Salinispora arenicola

Abstract

Six new anthraquinone-γ-pyrones, saliniquinones A–F (1–6), which are related to metabolites of the pluramycin/altromycin class, were isolated from a fermentation broth of the marine actinomycete Salinispora arenicola (strain CNS-325). Their structures were determined by analysis of one- and two-dimensional NMR spectroscopic and high-resolution mass spectrometric data. The relative and absolute configurations of compounds 1–6 were determined by analysis of NOESY NMR spectroscopic data and by comparison of circular dichroism and optical rotation data with model compounds found in the literature. Saliniquinone A (1) exhibited potent inhibition of the human colon adenocarcinoma cell line (HCT-116) with an IC50 of 9.9 × 10−9 M. In the context of the biosynthetic diversity of S. arenicola, compounds 1–6 represent secondary metabolites that appear to be strain specific and thus occur outside of the core group of compounds commonly observed from this species.

Anticancer Drug Discovery from Microbial Sources: The Unique Mangrove Streptomycetes

“…Nevertheless, the expansion in microbial natural products research has led to the revelation of clinically important compounds such as romidepsin (from Chromobacterium violaceum ) [ 111 ], wortmannin (from Talaromyces wortmannin and Penicillium funiculosum ) [ 112 , 113 ], marinomycins ( Marinispora spp.) [ 114 ], saliniquinones (from Salinispora arenicola ) [ 115 ] and many more, which exerted potent cytotoxic capabilities. Thus, the current review attempts to provide a fresh perspective on anticancer compounds from mangrove-derived streptomycetes.…”

The marine actinomycete genus Salinispora: a model organism for secondary metabolite discovery

“…Another example of the metabolic diversity among strains that are clonal at the 16S rRNA level comes from S. arenicola strain CNS-325, which yielded saliniquinones A–F ( 45 - 50 ) 116 . These six new anthraquinone-γ-pyrones are highly cytotoxic and represent the first members of the pluramycin class to contain both a terminal olefin and five carbons in the C-2 side chain.…”

New Marine Natural Products of Microbial Origin from 2010 to 2013

“…nov. [86] . 蒽 醌-γ-吡喃酮类化合物 192～197 来自于一株居沙盐孢菌 (Salinispora arenicola, 帕劳), 化合物 193 对 HCT-116 细胞和 MRSA 都有很强的抑制作用 [87] ; 向异戊烯转移 酶缺失的突变株 S. arenicola CNS-205 [88] 的培养基中添 加 N-乙酰化色氨酸时, 得到新的环肽类化合物 198～ 201 [89] . 对太平洋盐孢菌 S. pacifica(斐济)进行基因组和 化学分析时得到 20S 蛋白酶体抑制物 202 [90] .…”