Two new neo-clerodane diterpenoids, teucvisins A and B (1, 2), and three new 19-nor-neoclerodane diterpenoids, teucvisins C-E (3-5), together with ten known constituents (6-15) were isolated from the whole plants of Teucrium viscidum. All the isolates were evaluated for their inhibitory activities of lipopolysaccharide (LPS)-induced nitric oxide production in RAW264.7 macrophages. The results indicated that compounds 11 and 15 showed moderate inhibition with an IC 50 value of 21.9 and 22.4 µM, respectively.
Key words clerodane diterpene; Teucrium viscidum; anti-inflammatoryThe genus Teucrium (Lamiaceae) includes approximately 300 species which are mainly distributed in the Mediterranean area. In China, there are eighteen species and ten varieties, mostly distributed in southern part of China. Teucrium species are generally aromatic and ornamental plants, meanwhile, a large number of species are used in folk medicine and pharmacy for their diverse bioactivities, such as anti-inflammatory, 1) antiacetylcholinesterase, 2) antidiabetic, 3-5) antifeedancy 6,7) and antimicrobial effects. 8) Teucrium viscidum, a folk medicine in China, is used to treat hematemesis, pulmonary abscesses, traumatic injuries, and bites from rabid dogs or venomous snakes.9) Previous phytochemical studies of this plant have afforded diterpenes, 10-13) triterpenoids, sterols and lignans.14) Our further investigation on this plant led to the isolation of five new neo-clerodane diterpenes, teucvisins A-E (1-5) (Fig. 1), together with ten known diterpenes (6-15). Herein, we described the isolation and structure elucidation of 1-5 and the anti-inflammatory activities of all the isolates. C-NMR spectrum (Table 1) revealed the presence of 20 carbons, which could in combination with the heteronuclear single quantum coherence (HSQC) and be assigned to two lactone carbonyls (δ C 178.1, 177.8), four olefinic carbons (δ C 144.4, 139.7, 125.2, 108.2), four oxygenated carbons (δ C 78.4, 72.4, 70.1, 69.6) and ten aliphatic resonances (δ C 51.8, 48.4, 42.7, 40.0, 34.2, 33.7, 32.7, 23.5, 21.4, 16.6). The fulfilled analysis of NMR data including HSQC, heteronuclear multiple bond connectivity (HMBC) and rotating frame Overhauser enhancement spectroscopy (ROESY) experiments, allowed for an unambiguous assignment of all proton and carbon signals. The above total data showed that 1 was a neo-clerodane diterpene, whose NMR data were similar to teucrin H2, previously isolated from the genus Teucrium.
Results and Discussion