- Biosynthesis of an Anti-Addiction Agent from the Iboga Plant
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(-)-Ibogaine and (-)-voacangine are plant derived psychoactives that show promise as treatments for opioid addiction. However, these compounds are produced by hard to source plants, making these chemicals difficult for broad-scale use. Here we report the complete biosynthesis of (-)-voacangine, and de-esterified voacangine, which is converted to (-)-ibogaine by heating, enabling biocatalytic production of these compounds. Notably, (-)-ibogaine and (-)-voacangine are of the opposite enantiomeric configuration compared to the other major alkaloids found in this natural product class. Therefore, this discovery provides insight into enantioselective enzymatic formal Diels-Alder reactions.
- Farrow, Scott C.,Kamileen, Mohamed O.,Caputi, Lorenzo,Bussey, Kate,Mundy, Julia E. A.,McAtee, Rory C.,Stephenson, Corey R. J.,O'Connor, Sarah E.
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- Photosensitized oxidation, by single-electron transfer, of catharanthine and vindoline: A highly regio- And diastereoselective photocyanation reaction
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The irradiation, by visible light, of (+)-catharanthine 1 and of (-)-16-O-acetylvindoline 5 in the presence of cyanide ion and a catalytic amount of a photosensitizer known to produce singlet oxygen leads to (+)-3β-cyanocatharanthine 3 and the new (-)-16-O-acetyl-3α-cyanovindoline 6. The complete stereostructural identification of these compounds has been ascertained by an accurate spectroscopic survey. High regio- and diastereoselectivities (de > 99%) are observed. Some experiments have been performed which confirm unambiguously that singlet oxygen is the oxidizing species in such photochemical conditions. The Royal Society of Chemistry 2000.
- Cocquet, Guillaume,Rool, Patrice,Ferroud, Clotilde
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- METHOD AND MEANS FOR MANUFACTURING TERPENE INDOLE ALKALOIDS
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The complex chemistry underlying the extensive transformations involved in terpene indole alkaloid synthesis makes identification of the biosynthetic genes challenging. The present invention relates to methods for producing a terpene indole alkaloid derivative, comprising the steps of: (1) providing a terpene indole alkaloid; and (2) providing a first enzyme termed "Precondylocarpine Acetate Synthase" (PAS) or a functional variant or homologue thereof; and/or a second enzyme termed "Dehydroprecondylocarpine Acetate Synthase" (DPAS) or a functional variant or homologue thereof, and optionally providing further identified enzymes involved in this pathway. The invention also encompasses related kits, enzymes, expression vectors, host cells and plants.
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Page/Page column 11; 31
(2019/10/04)
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- NEW BIS-INDOLE ALKALOIDS AS ANTICANCER DRUGS
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The field of this invention relates to novel cyclopropyl derivatives of the general formula (I) representing pharmaceutically applicable Vinca Rosea type alkaloid compounds, particularly having a cytostatic effect. The invention also is concerned processes for preparing these new alkaloids and their pharmacological compositions and the use of these compounds in treatment of cancer. R stands for a methyl or a formyl group, R1 stands for a methoxy or an amino group, R2 represents a hydroxy or acetoxy group, R3 stands for a hydrogen atom or a hydroxy group, R4 represents a hydrogen atom or R3 and R4 together represent a double bond, R5 and R6 represent hydrogen or fluorine atoms n = 1 or 2.
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Page/Page column 17
(2014/12/12)
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- SYNTHESIS OF VINCA ALKALOIDS AND RELATED COMPOUNDS XLVIII SYNTHESIS OF (+)-CATHARANTHINE AND (+/-)-ALLOCATHARANTHINE
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The first synthesis of natural (+)-catharanthine (1) has been achieved in a few steps and in ca. 20 percent overall yield based on indole-3-acetic acid.The isomeric (+/-)-allocatharanthine was also prepared.
- Szantay, Csaba,Boelcskei, Hedvig,Gacs-Baitz, Eszter
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p. 1711 - 1732
(2007/10/02)
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- COMPOSES ANTITUMORAUX DU GROUPE DE LA VINBLASTINE: NOUVELLE METHODE DE PREPARATION
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7'-Chloro-indolenines from several dimeric alkaloids of vinblastine type are useful intermediates in the preparation of antitumor derivatives belonging to seco-5',6' and nor-5'series.
- Andriamialisoa, R. Z.,Langlois, N.,Langlois, Y.,Potier, P.
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p. 3053 - 3060
(2007/10/02)
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