Methoxynepetaefolin, a new labdane diterpene from Leonotis nepetaefolia
β Scribed by P.S. Manchand
- Publisher
- Elsevier Science
- Year
- 1973
- Tongue
- French
- Weight
- 98 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Our recent studies's2 on the constituents of the tropical plant Leonotis nepetaefolia R. Br (Labiatae) have resulted in the isolation and structural elucidation of a number of new labdane ditkrpenes of which nepetaefolin (I) is the most abundant. This comunication reports the isolation of an additional but biogenetically interesting labdane diterpene, methoxynepetaefolin (II), as a minor constituent of L. nepetaefolia. 26 Methoxynepetaefolin has the molecular formula C23H3208 (Mt 436.1985), mp 275-278O, {a)D -35.8' (C 1.2, CHC13), v CHC13 max 1737 (OAc), 1725 (s-lactone) and 1031 cm-l (OMe). The n.m.r. spectrum (1ZDc13)~ of methoxynepetaefolin revealed a close structural similarity to that of nepetaefolin. Thus, two sharp 3H singlets at 1.16 and 2.02 are attributed to methyl and acetate groups at C4 and C6 respectively; absorption due to the methine proton at C6 appeared as overlapping triplets centred at 5.20. Three AB quartets were discernible: the first of these, at 2.30 and 2.62 (J = 3.5 Hz), is due to the protons of the terminal epoxide at C8; the second, at 3.53 and 3.78 (J = 8 Hz), represents absorption due to the methylene protons on Cl6; the third, at 4.00 and 5.10 (J = 11 Hz), is indicative of the methylene protons on C20 which form part of the d-lactone system. A pair of doublets at 4.96 and 5.02 (J = 6 and 3 Hz) are attributed to the X part of an ABX system, these absorptions are therefore ascribed to the proton on C15. Absorption due to the methoxyl group appeared as a sharp singlet at 3.38. No structurally diagnostic features of any significance could be obtained from the mass spectrum4 of methoxynepetaefolin; the main peaks present were at m/e 405 (M-OCH3), 376 (Y-CH3C02H) and 361 (M-CH3C02H -CH3).
π SIMILAR VOLUMES
A bicyclic diterpene triol with a new rearranged labdane carbon skeleton was isolated from the aerial parts of Halimium viscosum (Willk.) Pinto da Silva (S. Joa Λo da Pesqueira). Its structure was established by FAB MS and two-dimensional NMR experiments ( 1 H/ 1 H, 1 H/ 13 C) and its stereochemistr