New Sesterterpenes from the Antarctic Sponge Suberites sp.

IF 4.9 2区医学 Q1 CHEMISTRY, MEDICINAL

Marine Drugs Pub Date : 2024-12-06 DOI:10.3390/md22120551

Stine S H Olsen, Sydney K Morrow, Julia L Szabo, Michael N Teng, Kim C Tran, Charles D Amsler, James B McClintock, Bill J Baker

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Abstract

Chemical investigation of the Antarctic sponge Suberites sp. has previously led to the identification of new suberitane derivatives, some of which show bioactivity toward respiratory syncytial virus (RSV). Our ongoing NMR-guided investigation of new specimens of the sponge resulted in the isolation of five new analogs (1-5), previously reported suberitenones A-D (6-9), and oxaspirosuberitenone (10). Suberitenone K (1) was characterized as the 8-keto derivative of 6, while three new phenols, suberitandiol (2), abeosuberitandiol (3), and furanosuberitandiol (4), and the degraded sesterterpene norsuberitenone B (5) were also found. Compound 3 displays a ring contraction while 4 has a new dihydrofuran ring. Structural characterization was achieved by a combination of NMR, HR-MS, and X-ray diffraction (XRD). Moderate activity towards RSV was reported for 9 and the new metabolite 1, with IC₅₀ values of 15.0 μM and 39.8 μM, respectively.

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南极海绵亚亚种的新酯萜。

对南极海绵Suberites sp.的化学研究已经鉴定出新的Suberites衍生物，其中一些对呼吸道合胞病毒（RSV）具有生物活性。我们正在对海绵新标本进行核磁共振引导调查，结果分离出五种新的类似物（1-5），先前报道的亚戊烯酮A-D（6-9）和oxaspiro亚戊烯酮（10）。亚癸烯酮K(1)被鉴定为6的8-酮衍生物，同时还发现了三个新的酚，亚癸烯二醇(2)、亚癸烯二醇(3)和呋喃亚癸烯二醇(4)，以及降解的二萜去癸烯二酮B(5)。化合物3有缩环，而化合物4有一个新的二氢呋喃环。结构表征是通过NMR， HR-MS和x射线衍射（XRD）的组合来实现的。9和新代谢产物1对RSV有中等活性，IC50值分别为15.0 μM和39.8 μM。

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来源期刊

Marine Drugs 医学-医药化学

CiteScore

9.60

自引率

14.80%

发文量

671

审稿时长

1 months

期刊介绍： Marine Drugs (ISSN 1660-3397) publishes reviews, regular research papers and short notes on the research, development and production of drugs from the sea. Our aim is to encourage scientists to publish their experimental and theoretical research in as much detail as possible, particularly synthetic procedures and characterization information for bioactive compounds. There is no restriction on the length of the experimental section.