Tabernaemontana divaricata

Cathanthus roseus Nicotiana tabacum Cinchona robusta Tabernaemontana divaricata 3-1 STR (2 1 wv) D 4.5 cm batch and chemostat N 2.5 -16.7 s Q 0.33 wm t < 30 d biomass production total organic carbon extracellular protein membrane integrity substrate consumption [107]... 

Related alkaloids 19,20-Z-vallesamine (10a) and 19,20-E-vallesamine (10b) have been extracted from the leaves of Alstonia scholaris (87H(26)413), from the bark of Tabernaemontana dichotoma (85P2097) and from cell cultures Tabernaemontana divaricata (88MI393). 

In Tabernaemontana divaricata treatment of plant cell suspension cultures with an elicitor cause inhibition of CS activity [24,25]. This response is accompanied by stimulation of activity of constitutive enzyme activities of the isoprenoid pathway leading to 2,3-oxidosqualene (squalene synthase and squalene oxidase), and induction of enzymes required for biosynthesis of pentacyclic triterpenoid phytoalexins (/lAS and aAS). Thus inhibition of the branchpoint enzyme CS results in increased flux through the triterpenoid pathway. 

Voacamine has been found to occur in the root bark of Tabernaemontana divaricata.102... 

Fulton, D.C., Kroon, P.A. and ThrelfaU, D.R. (1994) Enzymological aspects of the redirection of terpenoid biosynthesis in elicitor-treated cultures of Tabernaemontana divaricata. Phytochemistry, 35,1183-6. 

SOURCE Ervatamia coronaria (Jacq) Stapf (syn. Tabernaemontana divaricata R.Br. 

Tabernaemontana divaricata (double flower variety) provided an unusual minor alkaloid, voaharine (178), whose structure was established by X-ray analysis [137]. Voaharine is exceptional in being in all probability a tryptamine and jccologanine derived alkaloid but possessing a 3-quinolone instead of an indole chromophore. Voaharine is probably derived from voaphylline (180) (which is also present in the plant) via oxidation and rearrangement and represents the first instance of a 3-quinolone-type alkaloid obtained from Tabernaemontana. Besides these, and the known alkaloids N-methylvoaphylline (181), pachysiphine (tabersonine-P-epoxide) and apparicine, as well as two new bisindoles (vide infra), the plant also provided several new alkaloids of the aspidosperma-type including (-)-mehranine (179), voafinine (182), N-methylvoafinine (183), voafinidine (184) and voalenine (185) which were obtained in minute amounts [138-140]. 

The popular garden plant Tabernaemontana divaricata which is extensively grown in gardens in Malaysia as well as in India provided several novel bisindoles, one of which, viz., conophylline (303) has been shown to be a potent inhibitor of ras functions (vide infra). There are two distinct varieties, the single flower variety produces both conophylline (303) and conophyllidine (304) [137,180] while the double flower variety gives in addition, a third dimeric alkaloid, conofoline (305) [ 138] as well as several new aspidosperma-type compounds. 

As no major differences were found for the glucolysis products of strictosidine for the C. roseus and the Tabernaemontana divaricata enzymes, the key for the formation of the different types of indole alkaloids is probably after the glucosidase, as the two cell cultures do produce quite different alkaloids (39,52,182,218),... 

Chaiyana W, Rades T, and Okonogi S. (2013). Characterization and in vitro permeation study of microemulsions and liquid crystalline systems containing the anticholinesterase alkaloidal extract from Tabernaemontana divaricata. International Journal of Pharmaceuticals, 452, 201-210. 

R. van der Heijden, A. Hermans-Lokkerbol, L.P.J. de Kool, P.A.A. Harkes and R. Verpoorte, Indole alkaloids from suspension cultures of Tabernaemontana divaricata, I. Isolation and identification of the alkaloids. Plants Medica. Submitted. 

Formation and degradation of some aspidospermatan indole alkaloids in suspension cultures of Tabernaemontana divaricata, Zeitschrift f. 

R. van der Heijden, P.J. Lamping, P.P.Out, R. Wijnsma and R. Verpoorte, High-performance liquid chromatographic determination of indole alkaloids in a suspension culture of Tabernaemontana divaricata, J. Chromatogr. 396 (1987) 287-295. 

Pedunculine and Conofoline have not been compared but are probably identical. Mp. and opt. rotn. refer to Confoline. Alkaloid from leaves of Ervatamia peduncularis and Tabernaemontana divaricata (Apocynaceae). Purple amorph. solid. Mp 196-198 . [aj -97 (c, 0.725 in CHCI3). 

The TIAs form a family of more than 3,000 representatives. These alkaloids, which are unique in plants, have been found in several plant families such as Apocynaceae, Loganiaceae, Nyssaceae, and Rubiaceae, which belong all to the Gentianales order. The most important and weU-known plants that produce TLAs are Tabernaemontana divaricata, Rauvolfia serpentina, and C. roseus [1]. 

---