Tanjungides A and B: New Antitumoral Bromoindole Derived Compounds from Diazona cf formosa. Isolation and Total Synthesis

Marine Drugs

Carmen Murcia²  Laura Coello²  Rogelio Fernández²  Mar໚ Jesús Martín²  Fernando Reyes¹  Andrés Francesch²  Simon Munt² 

[1] Fundación MEDINA, Avda. del Conocimiento 3, Parque Tecnológico de Ciencias de la Salud, Granada 18016, Spain; E-Mail:;Medicinal Chemistry Department, PharmaMar S.A., Avda. de los Reyes 1, Pol. In. La Mina, Colmenar Viejo, Madrid 28770, Spain; E-Mails:

关键词: bromoindole;    tunicate;    Diazona cf formosa;    cytotoxicity;    isolation;    structure elucidation;    total synthesis;   

DOI  :  10.3390/md12021116

来源: mdpi

【 摘 要 】

Tanjungides A (1) (Z isomer) and B (2) (E isomer), two novel dibrominated indole enamides, have been isolated from the tunicate Diazona cf formosa. Their structures were determined by spectroscopic methods including HRMS, and extensive 1D and 2D NMR. The stereochemistry of the cyclised cystine present in both compounds was determined by Marfey’s analysis after chemical degradation and hydrolysis. We also report the first total synthesis of these compounds using methyl 1H-indole-3-carboxylate as starting material and a linear sequence of 11 chemical steps. Tanjungides A and B exhibit significant cytotoxicity against human tumor cell lines.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.