Abstract
Thuwalallenes A–E (1–3, 5 and 8) and thuwalenynes A–C (4, 6, 7), new C15 acetogenins featuring uncommon ring systems, along with cis-maneonene D (9), thyrsiferol (10) and 23-acetyl-thyrsiferol (11) were isolated from the organic extract of a population of the red alga Laurencia sp., collected at Rose Reef off the village of Thuwal in the Red Sea waters of the Kingdom of Saudi Arabia. The structure elucidation of the isolated natural products was based on extensive analysis of their spectroscopic data. Compounds 1–6, 8, 10 and 11 were evaluated for their anti-inflammatory activity by quantifying nitric oxide (NO) release in response to TLR4 stimulation in macrophages. Besides compound 4 that did not exhibit any activity, all other tested metabolites inhibited NO production from activated macrophages. Among them, thyrsiferol (10) and 23-acetylthyrsiferol (11) displayed activity with IC50 values in the low nM scale without cytotoxicity.
Highlights
The genus Laurencia (Rhodomelaceae) is a cosmopolitan genus, comprising ca. 140 accepted species [1]
Apart from the challenging taxonomy, the genus presents a wide chemical diversity and an unparalleled ability to produce a large variety of secondary metabolites, including C15 acetogenins, sesquiterpenes, diterpenes and triterpenes, often with a high degree of halogenation, conferring effective chemical defence against herbivores [2,3]
In the context of our ongoing interest on the chemical diversity of its secondary metabolites [2,7,8,9,10], we investigated the chemistry of a Laurencia sp. population of this genus and the bioactivity potential of its secondary metabolites [2,7,8,9,10], we investigated the collected near the village of Thuwal in the central Saudi Arabian Red Sea
Summary
The genus Laurencia (Rhodomelaceae) is a cosmopolitan genus, comprising ca. 140 accepted species [1]. Mar. Drugs 2019, 17, 644 last 60 years Laurencia has been extensively studied, and acknowledged as the most heavily investigated genus of red algae (Rhodophyta), new compounds are still being isolated [5,6,7]. Acknowledged as the most heavily investigated genus of red algae (Rhodophyta), new context of our ongoing interest on the chemical diversity of this genus and the bioactivity potential compounds are still being isolated [5,6,7]. Population of this genus and the bioactivity potential of its secondary metabolites [2,7,8,9,10], we investigated the collected near the village of Thuwal in the central Saudi Arabian Red Sea. we report the chemistry of a Laurencia sp. Among which 1–8 are new natural products, and the evaluation of their anti-inflammatory activity
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