Molecules 2007, 12(7), 1307-1315; doi:10.3390/12071307
Article

A Simplified Procedure for Indole Alkaloid Extraction from Catharanthus roseus Combined with a Semi-synthetic Production Process for Vinblastine

1,2,* email, 2,* email, 3email, 2 and 1email
Received: 30 May 2007; in revised form: 1 July 2007 / Accepted: 4 July 2007 / Published: 5 July 2007
(This article belongs to the Special Issue Phenolics and Polyphenolics)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: Dried leaves of Catharanthus roseus were extracted with aqueous acidic 0.1 M solution of HCl. Alkaloid-embonate complexes were obtained as precipitates by treating the extract with an alkaline (NaOH) solution of embonic acid (4,4-methylene-bis-3-hydroxynaphtalenecarboxylic acid). The precipitate mainly consisted of catharanthine and vindoline embonates and it was directly used as the starting material for a semi-synthesis of the anti-cancer bisindole alkaloid vinblastine. The coupling reaction involved oxidation of catharanthine in aqueous acidic medium by singlet oxygen (1O2), continuously produced in situ by the reaction between H2O2 with NaClO. An excess of NaBH4 was used for the reduction step. Analysis of the reaction mixture indicated a maximum yield of 20% for vinblastine at pH 8.3, based on the initial amount of catharanthine concentration. Direct-injection electrospray ionization mass spectrometry in positive ion mode was used for the identification of vinblastine. The mass spectra of vinblastine were dominated by the corresponding protonated molecular ion [M+H]+ at m/z 811 and the characteristic fragment ions matched with those of the standard compound.
Keywords: Indole alkaloids;vinblastine;semi-synthesis;mass spectrometry;electrospray ionization.
PDF Full-text Download PDF Full-Text [75 KB, uploaded 18 June 2014 19:27 CEST]

Export to BibTeX |
EndNote


MDPI and ACS Style

Verma, A.; Laakso, I.; Seppänen-Laakso, T.; Huhtikangas, A.; Riekkola, M.-L. A Simplified Procedure for Indole Alkaloid Extraction from Catharanthus roseus Combined with a Semi-synthetic Production Process for Vinblastine. Molecules 2007, 12, 1307-1315.

AMA Style

Verma A, Laakso I, Seppänen-Laakso T, Huhtikangas A, Riekkola M-L. A Simplified Procedure for Indole Alkaloid Extraction from Catharanthus roseus Combined with a Semi-synthetic Production Process for Vinblastine. Molecules. 2007; 12(7):1307-1315.

Chicago/Turabian Style

Verma, Arvind; Laakso, Into; Seppänen-Laakso, Tuulikki; Huhtikangas, Aarre; Riekkola, Marja-Liisa. 2007. "A Simplified Procedure for Indole Alkaloid Extraction from Catharanthus roseus Combined with a Semi-synthetic Production Process for Vinblastine." Molecules 12, no. 7: 1307-1315.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert