Tabernaemontana indole alkaloids from

Abe F, Tatsuo Y, Guevara- BQ. Indole alkaloids from Tabernaemontana pandaeaqui in the Philippines. Biochem Syst Ecol 1993 21 847-848. 

III. Indole Alkaloids from ChemicaUy Investigated Tabernaemontana Species... 

Indole alkaloids from Tabernaemontana plants are all biogenetically derived from tryptophan (tryptamine) and secologanine, which constitute the indole and terpenic portions, respectively, and can be classified into nine main types depending on the structural characteristics of their skeleton (Fig. 1). 

In an extensive study of indole alkaloids from Tabernaemontana dichotoma, Perera and co-workers reported the isolation and characterization of eight bisindole alkaloids of the vobasine-coronaridine type (90,93). Of these, the previously known alkaloids tabernamine (173), voacamine (175), and 3 R/S-hydroxyvoacamine (178) were identified from their spectral characteristics and co-TLC with authentic samples (91). UV, IR, and XH NMR data of three of the bisindole alkaloids indicated a close structural relationship to tabernamine (173), and the XH NMR of one of these alkaloids was identical to that of tabernamine, except that the signal at 6 2.62 ppm due to the N-Me group was missing. The MS and IR spectroscopic data... 

Heijden der van R, Brouwer RL, Verpoorte R, Beek van TA, Harkes PAA, Svendsen AB. Indole alkaloids from Tabernaemontana elegans. Planta Med 1986 52 144-7. 

Indole alkaloids from suspension cultures. of Tabernaemontana species. 

R. van der Heijden, A. Hermans-Lokkerbol, R. Verpoorte and A. Baerheim Svendsen, Pharmacognostical studies on Tabernaemontana XX. Ion-pair droplet counter-current chromatography of indole alkaloids from suspension cultures,... 

P.A.A. Harkes and A. Baerheim Svendsen, Indole alkaloids from a callus culture of Tabernaemontana elegans, Phytochemistry, 25 (1986) 843. 

Fig. 1. Classification of indole alkaloids isolated from Tabernaemontana plants.

The monoterpenoid indole alkaloids constitute a laige group and careful investigation of plants, particularly from the Apocynaceae (Kopsia, Tabernaemontana, Alstonia, Leuconotis) and Rubiaceae (Uncaria, Mitragyna) have yielded many novel compounds. 

Tubotaiwine (168), a condylocarpine-type indole alkaloid, obtained from Tabernaemontana dichotoma of Sri Lankan origin, was subjected to a stereochemical investigation with extensive NMR studies involving NOE dif-... 

The genus Tabernaemontana (Apocynaceae) is a wellknown source of a variety of indole alkaloids, many of which have pharmacological interest (40). Cell cultures of plants from this genus have been initiated (41) and were found to produce alkaloids. In order to be able to identify the alkaloids an isolation method has been elaborated, using droplet counter current chromatography (DCCC). 

Munoz V, Morretti C, Sauvain M et al (1994) Isolation of bis-indole alkaloids with antileishmanial and antibacterial activities from Peschiera van heurkii (syn. Tabernaemontana van heurkii). Planta Med 60 455-459... 

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]. 

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