Chemical investigation of an Indonesian specimen of Theonella swinhoei afforded the new dimeric macrolides isoswinholide B (5) and swinholide K (6), along with the known swinholides A (1), B (2) and D (3) and isoswinholide A (4). Isoswinholide B showed an unprecedented 21/19' lactonization pattern, while swinholide K included an sp(2) methylene attached at C-4 and an additional oxymethine group at C-5, whose configuration has been determined through application of J-based configuration analysis. The isolated swinholides (1-6), with the exception of isoswinholide B, showed a cytotoxic activity on HepG2 (hepatocarcinoma cell line) in the nanomolar range
Isoswinholide B and swinholide K, potently cytotoxic dimeric macrolides from Theonella swinhoei / Sinisi, Annamaria; Calcinai, B; Cerrano, C; Dien H., A; Zampella, Angela; D'Amore, C; Renga, B; Fiorucci, S; TAGLIALATELA SCAFATI, Orazio. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - 21:17(2013), pp. 5332-5338. [10.1016/j.bmc.2013.06.015]
Isoswinholide B and swinholide K, potently cytotoxic dimeric macrolides from Theonella swinhoei
SINISI, ANNAMARIA;ZAMPELLA, ANGELA;TAGLIALATELA SCAFATI, ORAZIO
2013
Abstract
Chemical investigation of an Indonesian specimen of Theonella swinhoei afforded the new dimeric macrolides isoswinholide B (5) and swinholide K (6), along with the known swinholides A (1), B (2) and D (3) and isoswinholide A (4). Isoswinholide B showed an unprecedented 21/19' lactonization pattern, while swinholide K included an sp(2) methylene attached at C-4 and an additional oxymethine group at C-5, whose configuration has been determined through application of J-based configuration analysis. The isolated swinholides (1-6), with the exception of isoswinholide B, showed a cytotoxic activity on HepG2 (hepatocarcinoma cell line) in the nanomolar rangeI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
