Laurene-type sesquiterpenes from the Red Sea red alga Laurencia obtusa as potential antitumor–antimicrobial agents

• Published in: European journal of medicinal chemistry 2012-09, Vol.55, p.462-466
• Main Authors: Alarif, Walied M., Al-Lihaibi, Sultan S., Ayyad, Seif-Eldin N., Abdel-Rhman, Mohamed H., Badria, Farid A.
• Format: Article
• Language: English
• Subjects: Animals; Anti-Infective Agents - chemistry; Anti-Infective Agents - isolation & purification; Anti-Infective Agents - pharmacology; Anti-Infective Agents - therapeutic use; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Antineoplastic Agents - therapeutic use; Bacteria - drug effects; Biological and medical sciences; Candida albicans; Carcinoma, Ehrlich Tumor - drug therapy; EAC; Fungi - drug effects; Gram-positive bacteria; Laurencia - chemistry; Marine algae; Medical sciences; Microbial Sensitivity Tests; Miscellaneous; Pharmacology. Drug treatments; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; Sesquiterpenes - pharmacology; Sesquiterpenes - therapeutic use; Terpenoids
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2012.06.060

Three new laurene-type sesquiterpenes, 12-hydroxy isolaurene (1), 8,11-dihydro-12-hydroxy isolaurene (2) and isolauraldehyde (3) were isolated from the organic extract of the red alga Laurencia obtusa. The chemical structures of isolates were determined by interpretation of their spectral data 1D and 2D NMR, UV, IR and MS. The newly isolated compounds were tested for their antimicrobial and antitumor activities. Compounds (1–3) exhibited potent activity against the Gram-positive Bacillus subtilis and Staphylococcus aureus, where 3 proved to be the most active (MIC 35 and 27 μg/mL, respectively). Moreover, compound 3 exhibited a significant activity against Candida albicans (MIC of 70 μg/mL) and revealed to have very promising activity in an in vitro model of Ehrlich ascites Carcinoma. Novel laurene sesquiterpenes exhibited promising antimicrobial and antitumor activity in an in vitro model of Ehrlich ascites carcinoma were isolated from marine alga Laurencia obtusa. [Display omitted] ► New laurene-sesquiterpenes were isolated from nature. ► 1–3 exhibited potent activity against the Gram-positive B. subtilis and S. aureus. ► Compound 3 showed a significant activity against Candida albicans. ► 3 has very promising activity in an in vitro model of EAC.