Apovincaminic acid

Apovincaminic acid ethylester was supplied by Richter Gedeon Co., (-)-dihydroapovincaminic acid ethyl ester was prepared according to the procedure described in (11). fSj-a, -diphcnyl-2-py rro 1 idincmethanol was synthesised as described (12). 2-benzylidene-l-benzosuberone was prepared as described in (13). Isophorone was supplied by Merck. Cinchonidine was purchased from Fluka. 

Chrom Q column by Gazdag et al.. Derivatization (silylation with N,0-bis(trimethylsilyl) trifluoroacetamide) was needed for those alkaloids containing free hydroxy groups and/or a carboxylic acid group (vincaminic and apovincaminic acids). In Table 17.6 the retention times and elution temperatures of the vinca alkaloids investigated - as such and as derivatives -are given. 

PolgSr and Vereczkey applied gas chromatography with a glass capillary column for the determination of apovincaminic acid, the main metabolite of apovincaminic acid ethylester (vinpocetine) in human plasma. Apovincaminic acid was recovered from plasma by addition of tetrabutylammonium hydroxide and extraction with chloroform. It was transformed into its... 

Column pBondapak C18 (300x3.9 mm ID), mobile phase acetonitrile - 0.01 H ammonium carbonate (6 4), flow rate 1 ml/min, detection UV 280 nm. Peaks 1, (+)-cis-apovincamine 2, (+)-cis--dehydroepivincamine 3, (+)-cis-dehydrovincamine 4, (+)-trans-vincaminic acid ethyl ester 5, (+)-cis-epivincamine 6, (-)-cis-epivincamine 7, (+)-cis-vincamine 8, (-)-cis-vincamine 9, (+)-cis-epivincaminic acid ethyl ester 10, (+)-trans-epivincaminic acid ethyl ester 11, (+)-cis-vincamone 12, (+)-cis-vincanole 13, (+)-cis-vincaminic acid ethyl ester 14, (+)--cis-isovincanole 15, (+)-cis-apovincamine 16, (+)-trans-apovincaminic acid ethyl ester ... 

Farkas et al. compared the esters (-)-DHVin and (+)-DHVin with (-)-dihydro-apovincaminic acid as chiral modifiers in the enantioseleetive hydrogenation of EtPy and isophorone. 

Tungler, A., Mathe, T., Tamai, T., Fodor, K., Toth, G., Kajtar, J., Kolos-svary, 1., Herenyi, B., Sheldon, R.A. (1995) (-)-Dihydro-apovincaminic acid ethyl ester, preparation and use as a chiral modifier in enantioselective heterogeneous catal5dic hydrogenations. Tetrahedron Asymm. 6, 2395-2402. 

Vincamine, an alkaloid first isolated from Vinca minor has gained wide application in recent years as a specific cerebral vasodilator. Another alkaloid from the same species, (-)-ebur-namonine is marketed with a similar indication. A semisynthetic derivative of vincamine, the (+)-apovincaminic acid ethyl ester is produced under the trade name CAVINTON by the Hungarian Pharmaceutical Company Gedeon Richter. The latter compound has the trade name CALAN in Japan with a substantial share of the market. 

Direct Quantification of Apovincaminic Acid Ethyl Ester (Cavinton) in Human Plasma and Urine by Mass Fragmentography... 

Nyakas C, Felszeghy K, SzaboR, Keijser JN, LuitenPG, Szombathelyi Z, Tihanyi K (2009) Neuroprotective effects of vinpocetine and its major metabolite c -apovincaminic acid on NMDA-induced neurotoxicity in a rat entorhinal cortex lesirai model. CNS Neurosci Ther 15 89-99... 

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