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Identification of a low vindoline accumulating cultivar of Catharanthus roseus (L.) G. Don by alkaloid and enzymatic profiling.
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The Madagascar periwinkle [Catharanthus roseus (L.) G. Don] is a commercially important horticultural flower species and is the only source of the monoterpenoid indole alkaloids (MIAs), vinblastine and vincristine, key pharmaceutical compounds used to combat a number of different cancers. The
The Suzuki-Miyaura reaction in the chemical transformations of vindoline.
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Vindoline and its analogues are important constituents of the Madagascan periwinkle Catharanthus roseus, and some of them are valuable chemotherapy drugs used in treatment for some types of cancer, including leukaemia, lymphoma, breast and lung cancer. The search for semi-synthetic congeners of
Completion of the seven-step pathway from tabersonine to the anticancer drug precursor vindoline and its assembly in yeast.
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Antitumor substances related to vinblastine and vincristine are exclusively found in the Catharanthus roseus (Madagascar periwinkle), a member of the Apocynaceae plant family, and continue to be extensively used in cancer chemotherapy. Although in high demand, these valuable compounds only
Efficacy and tolerability of vinorelbine in the cancer therapy.
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Vinorelbine (VRN) is one of the most representative compounds of its class: the vinca alkaloids. VRN interferes with microtubule assembly. VRN shows a better therapeutic index than the parent compound vincristine and vinblastine probably because of its higher affinity for mitotic microtubules. VNR
Molecular docking and pharmacogenomics of vinca alkaloids and their monomeric precursors, vindoline and catharanthine.
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Vinblastine and vincristine are dimeric indole alkaloids derived from Catharanthus roseus (formerly: Vinca rosea). Their monomeric precursor molecules are vindoline and catharanthine. While vinblastine and vincristine are well-known mitotic spindle poisons, not much is known about vindoline and
Modulation of drug cytotoxicity in wild-type and multidrug-resistant tumor cells by stereoisomeric series of C-20'-vinblastine congeners that lack antimicrotubule activity.
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Seven binary vinca alkaloid congeners were newly synthesized as the C14' or C16'(20') or C14'16'(20') stereoisomers of C20'-modified VBL. These congeners lacked detectable antimicrotubule activity in assays of polymerization of purified microtubule protein and of mitotic arrest induction. The
The effect of conjugation on antitumor activity of vindoline derivatives with octaarginine, a cell-penetrating peptide.
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Some Vinca alkaloids (eg, vinblastine, vincristine) have been widely used as antitumor drugs for a long time. Unfortunately, vindoline, a main alkaloid component of Catharanthus roseus (L.) G. Don, itself, has no antitumor activity. In our novel research program, we have prepared and identified new
Double-sides sticking mechanism of vinblastine interacting with α,β-tubulin to get activity against cancer cells.
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Vinblastine (VLB) and its derivatives have been used for clinical first-line drugs to treat various cancers. Due to the resistance and serious side effects from using VLB and its derivatives, there is a need to discover and develop novel VLB derivatives with high activity against cancer cells. In
Discovery of a P450-catalyzed step in vindoline biosynthesis: a link between the aspidosperma and eburnamine alkaloids.
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Here we report the discovery of a cytochrome P450 that is required for the biosynthesis of vindoline, a plant-derived natural product used for semi-synthesis of several anti-cancer drugs. This enzyme catalyzes the formation of an epoxide that can undergo rearrangement to yield the
Synthesis of anti-tumor dimeric indole alkaloids in catharanthus roseus was promoted by irradiation with near-ultraviolet light at low temperature.
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We have found that coupling between catharanthine and vindoline occurs non-enzymatically in the presence of flavin mononucleotide and manganese ions with near-ultraviolet light irradiation in vitro. The present study found that the concentrations of catharanthine and vindoline in Catharanthus roseus
Chromatographic analysis of Vinca alkaloids in human neoplastic tissues and host (mouse) tissues after injection in vivo or after incubation in vitro.
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A method for extracting from biological tissues vincristine, vinblastine, and their metabolites and analysis by high-performance liquid chromatography has been developed. After excision tissues are rapidly frozen in liquid nitrogen (less than 10 s) and powders are made under liquid N2. Extraction of
Ceric ammonium nitrate-promoted oxidative coupling reaction for the synthesis and evaluation of a series of anti-tumor amide anhydrovinblastine analogs.
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A new, practical and efficient method for the synthesis of anhydrovinblastine AVBL (1f) by oxidative coupling of vindoline and catharanthine in the presence of ceric ammonium nitrate (CAN) was developed. Under the optimized reaction conditions, we synthesized a new series of amide anhydrovinblastine
Development of efficient Catharanthus roseus regeneration and transformation system using agrobacterium tumefaciens and hypocotyls as explants.
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BACKGROUND
As a valuable medicinal plant, Madagascar periwinkle (Catharanthus roseus) produces many terpenoid indole alkaloids (TIAs), such as vindoline, ajamlicine, serpentine, catharanthine, vinblastine and vincristine et al. Some of them are important components of drugs treating cancer and
Heteromeric and homomeric geranyl diphosphate synthases from Catharanthus roseus and their role in monoterpene indole alkaloid biosynthesis.
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Catharanthus roseus is the sole source of two most important monoterpene indole alkaloid (MIA) anti-cancer agents: vinblastine and vincristine. MIAs possess a terpene and an indole moiety derived from terpenoid and shikimate pathways, respectively. Geranyl diphosphate (GPP), the entry point to the
Next Generation Antineoplastic Agents: A Review on Structurally Modified Vinblastine (VBL) Analogues.
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BACKGROUND
Throughout the history of human civilizations, cancer has been a major health problem. Despite the advancements made by modern medical sciences, complete treatment or removal of cancerous cells is still a challenging task. Vinblastine, an alkaloid obtained from Catharanthus roseus (L.) G.
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