Vinca minor

The enzyme responsible for the stereospecific condensation of trypt-amine and secologanin 34) was called strictosidine synthase, and its presence was demonstrated by Treimer and Zenk 194) in a number of indole alkaloid-producing plants, including Amsonia salicifolia, Catharanthus roseus, Ochrosia elliptica, Rauwolfia vomitoria, Rhazya orientalis, Stem-madenia tomentosa. Vinca minor, and Voacanga africana. Enzyme activity as high as 1698 pkat/mg protein was observed for O. elliptica. No... 

Euonymus europaeus. Vinca minor Altemaria spp. altersetin, alternariol, alternariol monomethylether, tenuazonic acid 198, 203, 246... 

Vincamine, vinblastine and vincristine are very important clinic alkaloids. They are produced naturally by plants vincamine by Vinca minor, and vinblascine and vincristine by Madagascar periwinkle Catharanthus roseus). The vindoline synthesis pathway starts with strictosidine and, via dehydrogeissoschizine, preakuammicine, stemmadenine and tabersonine, is converted to vindoline and vincristine (Figure 42). Conversion from vindoline to vinblastine is based on the NADH enzyme activity. Vinblastine and vincristine are very similar alkaloids. The difference is that vincristine has CHO connected to N, whereas vinblastine in the same situation has only CO3. This synthetic structural differences influence their activity. Vinblastine is used to treat Hodgkin s disease (a form of lymphoid cancer), while vincristine is used clinically in the treatment of children s leukaemia. Vincristine is more neurotoxic than vinblastine. 

The following plants contained substantial proportions of apiose, about the same as found in parsley Aegopodium pologaria (bishop s weed), Apium graveolens L. (celery), Conopodium majus (earthnut), Datus aucaparia (rowan), Desfontania spinosa, Ilex aquifolium (holly), Lavatera annual, Lemna wolffia (duckweed), Menyanthes trifoliata (bob bean), and Vinca minor (periwinkle). 

Further variants on the terpenoid indole alkaloid skeleton (Figure 6.82) are found in ibogaine from Tabemanthe iboga, vincamine from Vinca minor, and ajmaline from Rauwolfia serpentina. Ibogaine is simply a C9 Iboga type alkaloid, but is of interest as an experimental drug to treat heroin addiction. In a number of European countries, vincamine is used clinically as a vasodilator to increase cerebral blood flow in cases of senility, and ajmaline for cardiac arrhythmias. Ajmaline... 

Boyadzhiev, L. and Yordanov, B. (2004) Pertraction of indole alkaloids from Vinca minor L. Separation Science and Technology, 39, 1321. 

Robinin (= Kaempferol 3-0- galactosyl-rhamnosyl-7-0- rhamnoside) (flavonol O-glycoside) Vinca minor (Apocynaceae), Pueraria spp., Robinia pseudoacacia, Vigna spp. (Fabaceae) HIV-1 protease (< 68 pM) [42]... 

Vinca minor, cultivated in Georgia, USSR, has been shown to contain ( )-vincadifformine and vincine, both already known to occur in this species, together with apovincamine and 11-methoxyvincadifformine.92 Voaphylline, voaphylline hydroxyindolenine, and 11-hydroxytabersonine have been isolated from the leaves of Tabernanthe pubescens,43/ and 5,22-dioxokopsane (177) from the root bark of Alstonia venenata R. Br. 93 this is the first report of an alkaloid of the heptacyclic kopsine group in this species. 

The Vinca minor alkaloids vincadine (II-A) and vincaminoreine (II-B) are the 3-carbomethoxy- and 3-carbomethoxy-Aa-methyl derivatives, respectively, of ( + )-quebrachamine (10a). The same plant also contains ( + )-indolic-A-methylquebrachamine (10b). 

Figure 2-18. Top left Vinca minor, Top right. Norwegian tulip Bottom stone-carvings along the Via Appia Antica in Rome (photographs by the authors).

Catharanthus roseus (Madagascar periwinkle), Rauwolfia serpentina (Indian snakeroot), R. tetraphyllo (pinque-pinque, four-leaf devil pepper), R. vomitoria (African snakeroot), Vinca minor (periwinkle) (Apocynaceae)... 

Boyadzhiev L and Yordanov B. Pertraction of Indole Alkaloids from Vinca minor L. Sep Sci Tech, 2004 39(6) 1321-1329. Coucouvanis D. Dell Rosa and Jay Pike recognition and transport of amphiphilic molecules by a new class of inorganic ditopic receptors. The synthesis of M- Bu - salphen-3n-cr-n complexes and their use (M = Mn,Fe, n = 6) in the transport of tryptophan and serotonin across bulk liquid membranes. Comptes Rendus Chimie, 2003 6(3) 317-327. 

Through a biomimetic approach, tabersonine is also the semisynthetic precursor of vincamine, a Eburna alkaloid isolated from Vinca minor, and is used for cerebral insufficiency in Europe. Tabemanthe iboga has a long history of use as a stimulant in tropical Africa its main active principle is ibogaine, a controlled substance in many countries (Fig. 40). It is being actively investigated in the United States for its potential to induce opium addiction withdrawal. 

Periwinkle Vinca major, vinca minor Cytotoxicity, renal failure, hepatic failure, neurological damage... 

Vincamine is an alkaloid extracted from the plant Vinca minor. Ethyl apovincaminate is a related synthetic ethyl ester of vincaminic acid. These drugs have spasmolytic effects similar to those of reserpine, but also have metabolic effects, including, in high doses, inhibition of phosphodiesterase. Although increased cerebral blood flow has been reported after the intravenous administration of vincamine, there have been no reliable studies of blood flow after oral medication. Improvement in scores on some psychometric tests have been obtained in some patients with cerebrovascular disease, but no clear-cut practical benefit has been demonstrated. 

Commercial formulations obtained from the alkaloids in Vinca minor may not be free from adverse effects. Ventricular dysrhythmias have been observed, but only after intramuscular or intravenous administration, and they seem to reflect a direct effect on myocardial cells. Hypokalemia and a prolonged QT interval seem to be predisposing factors. Vincamine should therefore be avoided in patients with a prolonged QT interval (SEDA-2, 183) (SEDA-5, 206) (SEDA-5, 207) (SEDA-7, 228). 

Vinca minor/major periwinkle - Most water plants. 

Diphosphoglycerate (2,3 DPG, 14), a naturally occurring material that increases in people with anemia, was reported to inhibit the second phase of platelet aggregation.55 The inhibitory effect was potentiated by dipyridamole and Vinca minor alkaloids. 

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