A New Alkaloid and Other Anti-Implantation Principles from Tabernaemontana heyneana [**]

Abstract

A new alkaloid designated as ervatine, in addition to seven known alkaloids, viz. tabersonine, coronaridine, heyneanine, voacristine, voacristine hydroxyindolenine, hydroxyibogamine, and coronaridine hydroxyindolenine, were isolated from the fruit of Tabernaemontana heyneana Wall. Characterisation and structure elucidation of these compounds was made on the basis of their spectral analyses. The ethanolic extract and isolated alkaloids heyneanine and voacristine prevented pregnancy when administered during the preimplantation period in Sprague-Dawley rats. These were, however, found to possess significant uterotrophic activity.

References

• 1 Kirtikar K R, Basu D B. Indian Medicinal Plants. Vol II Allahabad, India; Lalit Mohan Basu 1987: 1576-77
• 2 Jain S K, DeFilipps R A. Medicinal Plants of India. Vol I Michigan; Reference Publication Inc 1991: 132
• 3 Wenkert E, Cochran D W, Hagaman E W, Schell F M, Neuss N, Katner  A S. Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances.  Journal of American Chemical Society. 1973;  95 4990-5
• 4 Plat M, Men J L, Maurice M J. Mass spectrometry in structural and stereochemical problems. Tetrahedron Letters 1962: 271-6
• 5 Gunasekara S P, Cordell G A, Farnsworth N R. Anticancer indole alkaloids of Ervatamia heyneana .  Phytochemistry. 1980;  19 1213-8
• 6 Kan C, Husson H P, Kan S K, Lounasmma M. Determination de structures Par RMN du 1H a 400 MHz: Albifloranine, un Nouvel Alacaloide de Tabernaemontana albiflora .  Planta Medica. 1981;  41 72-4
• 7 Govindachari T R, Joshi B S, Saksena A K. The structure of heyneanine. Tetrahedron Letters 1965: 3873-8
• 8 Schnoes H K, Thomas D W, Aksornvitaya R, Schleigh W R, Kupchan S M. The isolation and structural elucidation of voacristine hydroxyindolenine.  Journal of Organic Chemistry. 1968;  33 1225-7
• 9 Madinaveitia A, Reina M, Fuente G, Gonzalez A G. Obovamine, a new indole alkaloid from Stemmadenia obovata .  Journal of Natural Products. 1996;  59 185-9
• 10 Bullefon M D, Debray M M, Men-Olivier L, LeMen J. Alcaloides du Pandaca Mocquerysii var. Pendula.  Phytochemistry. 1975;  14 1649-52
• 11 Rastogi K, Kapil R S, Popli S P. New alkaloids from Tabernaemontana divaricata .  Phytochemistry. 1980;  19 1209-12
• 12 Wenkert E, Gottlieb H E. The C(2) stereochemistry of iboluteine.  Hetrocycles. 1977;  7(2) 753-8
• 13 Joshi B S, Rao P G, Roger D, Singri B P, Williams D J. Structure of tabernoxidine, a novel oxindole alkaloid from Tabernaemontana heyneana Wall.  Indian Journal of Chemistry. 1984;  23(B) 101-4
• 14 Mehrotra P K, Kamboj V P. Hormonal profile of coronaridine hydrochloride an antifertility agent of plant origin.  Planta Medica. 1978;  33 345-9
• 15 Singh M M, Chowdhury S R, Kulshreshtha D K, Kamboj V P. Antigestagenic activity of Ixora finlaysoniana in rat.  Contraception. 1993;  48 178-91
• 16 Keshri G, Lakshmi V, Singh M M, Kamboj V P. Post coital contraceptive property of Ferula assafoetida Linn. in female rats.  Pharmaceutical Biology. 1999;  37 273-6

1 ** CDRI Communication No. 5946.