Labdane Diterpenes from Marrubium velutinum and Marrubium cylleneum.

Chemical Constituents of Marrubium vulgare as Potential Inhibitors of Nitric Oxide and Respiratory Burst

“…IR absorptions were observed at 1770 (C=O), 3467 (OH) and 874 cm -1 (furan). The NMR spectral data showed characteristic signals of a labdane diterpene skeleton [8][9][10]. The spectral data of 1 (Table 1) closely resembled those of the labdane-type diterpene, marrubiin (5) [8], except for the presence of a carbonyl group (δ C 210.2) in place of a C-11 methylene group in compound 1.…”

“…The 1 H NMR spectrum exhibited three methyl groups at δ H 0.90, 0.98 and 1.43. Three olefinic proton signals at δ H 6.24, 7.21 and 7.34 indicated the presence of a furan ring [9,10]. Three spin systems were identified through COSY correlation spectroscopy.…”

Diterpene Lactones with Labdane, Halimane and Clerodane Frameworks

“…From the dichloromethane extract of the aerial parts of Marrubium velutinum a new diterpene bislactone, velutine C (37) was isolated [24]. This compound has two lactone groups one of them on side chain and the other on the decaline ring system.…”

“…The synthesis of compound 19 was achieved by a concise, highly efficient pathway featuring stereoselective addition of a new silyloxyfuryltitanium reagent to the aldehyde intermediate 10 and silyloxyfuranoxy-functionalization to give compound 21 before (+)-zerumin B (19)[16].The genus Leonurus is a widely distributed, medicinally important member of the Lamiaceae. Preparations of some plants of this genus have been utilized in the treatment of cardiovascular diseases and for sedative as well as uterotonic effects in Europe and China.From aerial parts of Leonurus heterophyllus were isolated leoheteronins A (22), B (23), C(24) and E (25)[17].…”

The Diterpenoids of the Genus Marrubium (Lamiaceae)

“…The latter substance appears to be identical to polyodonin (16). (25), and velutine C (26) [56]. From M. cylleneum, three products were isolated: marrubiin (1) [36,39] a natural product, although it had been reported a long time ago [39] as a semisynthetic derivative prepared by chemical transformation of marrubiin.…”