Cariocal, a new seco-abietane diterpene from the labiate coleus barbatus
β Scribed by Alphonse Kelecom; Tereza C. Dos Santos
- Book ID
- 104222407
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 267 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
cariocal is a new seco-diterpene isolated from a cardioactive fraction of the false boldo, Codeti batbcztti.
The structure was deduced from chemical and spectral data. The hexane and dichloromethane crude extracts of stems of the Labiate Co&w butbatti Bentham induce, in anaestezised rats, small lowering of blood pressure and discrete bradycardia. This activity was shown to be associated with a fraction containing several abietane diterpeeported in previous communications 2-4 .
Common features to 1 nes , some of whose structures were r all these diterpenes are a catechol this paper, we wish to report on the n the C-ring and a substituted C-20 methyl group 2-4 . In structure of cariocal ('_), a new diterpene obtained from the hexane crude extract by a combination of gel permeation and silica gel chromatography. Cariocal (1j5 was isolated as a colorless crystalline solid (m.p. 186-'89?, 101i5= +39?) '8'(29) ; 'H NMR (CD3COCD3) : see Table I ; 13c Nm (CD3C~~~3) : see Table 2. 6. A.I. SCOTT in "Interpretation of the Ultraviolet Spectra of Natural Products" chap 3, pplO9 6 1'3, Pergamon Student Edition, Oxford (1964), 7. F. YOSHIZAKI, P. RUEDI & C.H. EUGSTER, He&~et&~ Ckimica Acta 2, 2754 ('977). 8. diacetate (2): gum ; IaID =
π SIMILAR VOLUMES
tified 20th carbon, C-6. Therefore, through the 'H assignments, the carbon skelton was given and the planner structure of ,$, was established. Relative stereochemistries of both rings were determined by the NOES observed with respect to those five pairs of protons, (H-l, H-3), (H-l, Me-19), (H-3, Me