Thuwalallenes A-E and Thuwalenynes A-C: New C15 Acetogenins with Anti-Inflammatory Activity from a Saudi Arabian Red Sea Laurencia sp.

TY - JOUR

T1 - Thuwalallenes A-E and Thuwalenynes A-C

T2 - New C15 Acetogenins with Anti-Inflammatory Activity from a Saudi Arabian Red Sea Laurencia sp.

AU - Koutsaviti, Aikaterini

AU - Daskalaki, Maria G.

AU - Agusti, Susana

AU - Kampranis, Sotirios C.

AU - Tsatsanis, Christos

AU - Duarte, Carlos M.

AU - Roussis, Vassilios

AU - Ioannou, Efstathia

PY - 2019/11/15

Y1 - 2019/11/15

N2 - 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 SaudiArabia. The structure elucidation of the isolated natural productswas 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.

AB - 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 SaudiArabia. The structure elucidation of the isolated natural productswas 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.

KW - Acetogenins

KW - Anti-inflammatory activity

KW - Laurencia

KW - Thuwalallene

KW - Thuwalenyne

UR - http://www.scopus.com/inward/record.url?scp=85075051175&partnerID=8YFLogxK

U2 - 10.3390/md17110644

DO - 10.3390/md17110644

M3 - Journal article

C2 - 31731724

AN - SCOPUS:85075051175

SN - 1660-3397

VL - 17

JO - Marine Drugs

JF - Marine Drugs

IS - 11

M1 - 644

ER -