Neoclerodane Diterpenoids from Reehal Fatima, Teucrium yemense

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2017-06, Vol.80 (6), p.1900-1908
• Main Authors: Nur-e-Alam, Mohammad, Yousaf, Muhammad, Ahmed, Sarfaraz, Al-Sheddi, Ebtesam S, Parveen, Ifat, Fazakerley, David M, Bari, Ahmed, Ghabbour, Hazem A, Threadgill, Michael D, Whatley, Kezia C. L, Hoffmann, Karl F, Al-Rehaily, Adnan J
• Format: Article
• Language: English
• Subjects: Candida albicans - drug effects; Crystallography, X-Ray; Diterpenes - chemistry; Diterpenes - isolation & purification; Escherichia coli - drug effects; Hep G2 Cells; Humans; Lamiaceae - chemistry; Microbial Sensitivity Tests; Molecular Conformation; Molecular Structure; Mycobacterium smegmatis - drug effects; Nuclear Magnetic Resonance, Biomolecular; Plants, Medicinal - chemistry; Pseudomonas aeruginosa - drug effects; Saudi Arabia; Staphylococcus aureus - drug effects; Teucrium - chemistry
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.7b00188

Teucrium yemense (Defl), locally known as Reehal Fatima, is a medicinal plant commonly grown in Saudi Arabia and Yemen. Phytochemical investigation of the aerial parts of T. yemense yielded six new neoclerodane diterpenoids, namely fatimanol A–E (1, 2, 3, 5, and 6) and fatimanone (4), and the known teulepicephin (7). As both the Teucrium genus and the related Lamiaceae family have previously been widely reported to possess anthelmintic and antimicrobial activities, the structural and biological characterization of the seven diterpenoids was pursued. The structures of the new compounds were elucidated from their 2D NMR and MS profiles and by comparison to related compounds. The structure of fatimanol D (5) was confirmed by X-ray crystallographic analysis. The new structures contribute to the breadth of knowledge of secondary metabolites in this genus.