Valeriana officinalis actinidine from

Actinidine (26) has been isolated from the roots and rhizomes of Valeriana officinalis L.2S Boschniakine (27) has been found in the seeds of Plantago sempervirens its absolute configuration has been established by optical rotatory dispersion comparisons with other monoterpene bases.26 Venoterpine (28) has been found in Striga hermonteca the stereochemistry is as yet uncertain.27... 

The (+)-enantiomer (40) of actinidine, an alkaloid of Valeriana officinalis and Actinidia polygama, has been synthesized as outlined in Scheme 7, the starting material being obtained from (+)-pulegone.35... 

There is a small group of alkaloids related to the iridane monoterpenes which have the general structure (86). The synthesis of a new representative, valerianine (86 R = OMe), found in Valeriana officinalis L., has been described (Scheme 2), and an isomer (87) of the known actinidine (86 R = H) has been made from citronellonitrile (88) (Scheme 3). Thin-layer chromatography of V. officinalis extracts shows 12 zones whose constituents react with DragendorfTs reagent. ... 

In addition, to actinidine (14), Janot and co-workers also isolated a new monoterpene alkaloid from the roots of Valeriana officinalis following treatment with ammonia (25). The isolate was analyzed for the formula Ci0H8N2O, and the UV spectrum showed maxima at 261,314, and 324 nm, and the IR spectrum a band at 1680 cm-1 for an aryl ketone. The mass spectrum displayed a molecular ion at m/z 172 with fragment ions at m/z 157 (M+-15) and 129 (MM3), suggesting the presence of a methyl ketone. A methyl singlet was observed at 2.65 ppm, and a complex pattern of five... 

Two quaternary alkaloids, derivatives of actinidine and 8-hydroxyactini-dine, previously isolated from Valeriana officinalis (1), A-(4-hydroxyphe-nethyl)-actinidine (130) and 6,7-dihydro-4-(hydroxymethyl)-2-(4-hydroxy-phenethyl)-7-methyl-5//-2-pyridinium (124), were isolated from Valeriana wallichii (132). 

A quaternary alkaloid isolated (202) from the roots of Valeriana officinalis L. as the chloride, C18H22NOCI (mp 201°-203° decomp. [ ]o +50.5° in methanol) has been shown to be A-jS-(p-hydroxyphenyl)-ethylactinidinium chloride (CLXI). Pyrolysis of CLXI gives -actinidine (CLX) hydrochloride and, according to mass spectral evidence, p-hydroxystyrene. 

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