Selective cytotoxic eremophilane-type sesquiterpenes from Penicillium citreonigrum

• Published in: Journal of asian natural products research Vol. 17; no. 12; pp. 1239 - 1244
• Main Authors: Yuan, Wei-Hua, Goto, Masuo, Hsieh, Kan-Yen, Yuan, Bo, Zhao, Yu, Morris-Natschke, Susan. L, Lee, Kuo-Hsiung
• Format: Journal Article
• Language: English
• Published: ABINGDON Taylor & Francis 02.12.2015; Taylor & Francis Ltd
• Subjects: Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Breast Neoplasms - drug therapy; Chemistry; Chemistry, Applied; Chemistry, Medicinal; Crystallography, X-Ray; Crystals; cytotoxic; Cytotoxicity; Data interpretation; Diffraction; Drug Screening Assays, Antitumor; eremophilane-type sesquiterpene; Humans; Life Sciences & Biomedicine; Metabolites; Molecular Conformation; Molecular Structure; Penicillium - chemistry; Penicillium citreonigrum; Pharmacology & Pharmacy; Physical Sciences; Plant Sciences; Science & Technology; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; Sesquiterpenes - pharmacology; X-ray diffraction; Penicillium citreonigrum; eremophilane-type sesquiterpene; Metabolites; cytotoxic
• ISSN: 1028-6020; 1477-2213; 1477-2213
• DOI: 10.1080/10286020.2015.1115020

One new eremophilane-type sesquiterpene (1, citreopenin) was isolated from Penicillium citreonigrum (HQ738282), and the structure was elucidated by a combination of spectroscopic data interpretation and single-crystal X-ray diffraction analysis using Cu Kα radiation (CCDC 1030588). Compound 1 showed weak activity against KB-VIN (IC 50  = 11.0 ± 0.156 μM), while the known compound 3 exhibited selective cytotoxicity against MDA-MB-231 triple-negative breast cancer (TNBC) (IC 50  = 5.42 ± 0.167 μM).