03179
Vindoline
≥98.0% (HPLC)
别名:
Methyl (2β,3β,4β,5α,12R,19α)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylate
InChI key
CXBGOBGJHGGWIE-ACSXSLCXSA-N
InChI
1S/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3/t19-,20+,21+,23+,24+,25-/m0/s1
SMILES string
CC[C@]12C=CCN3CC[C@]4([C@@H](N(C)c5cc(OC)ccc45)[C@](O)([C@@H]1OC(C)=O)C(=O)OC)[C@H]23
assay
≥98.0% (HPLC)
optical activity
[α]/D -65±3°, c = 1.5 in methanol
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
storage temp.
2-8°C
Application
Vindoline, a monoterpenoid indole alkaloid, is used to synthesize vinblastine and vincristine via coupling catharanthine. Vindoline may be used as a reference standard during its identification and purification of from plant materials.
Biochem/physiol Actions
Vindoline is a monoterpenoid indole alkaloid exclusive to the Madagascar periwinkle plant (Catharanthus roseus). Vindoline combines catharanthine to derive the anti-cancer agents vinblastine and vincristine.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Shouhong Gao et al.
Journal of analytical methods in chemistry, 2018, 7967694-7967694 (2018-07-27)
Therapeutic drug monitoring for anticancer drugs could timely reflect in vivo drug exposure, and it was a powerful tool for adjusting and maintaining drug concentration into a reasonable range, so that an enhanced efficacy and declined adverse reactions could be
Daisuke Kato et al.
Journal of the American Chemical Society, 132(11), 3685-3687 (2010-03-02)
A concise asymmetric total synthesis of (-)-vindoline (1) is detailed based on a tandem intramolecular [4+2]/[3+2] cycloaddition cascade of a 1,3,4-oxadiazole inspired by the natural product structure, in which the tether linking the initiating dienophile and oxadiazole bears a chiral
Lesley-Ann Giddings et al.
The Journal of biological chemistry, 286(19), 16751-16757 (2011-04-02)
Plant cytochrome P450s are involved in the production of over a hundred thousand metabolites such as alkaloids, terpenoids, and phenylpropanoids. Although cytochrome P450 genes constitute one of the largest superfamilies in plants, many of the catalytic functions of the enzymes
Travis C Turner et al.
Organic letters, 15(5), 1100-1103 (2013-02-21)
The regioselective intermolecular coupling reaction of vindoline with a wide range of substrates including β-ketoesters, β-diketones, β-ketoaldehydes, β-ketonitriles, malononitriles, and β-cyanoesters provides an opportunity for the synthesis of vinblastine analogues containing deep-seated changes in the upper velbanamine subunit. The transition-metal-free
Péter Keglevich et al.
Molecules (Basel, Switzerland), 17(5), 5893-5914 (2012-05-23)
The synthetic investigation of biologically active natural compounds serves two main purposes: (i) the total synthesis of alkaloids and their analogues; (ii) modification of the structures for producing more selective, more effective, or less toxic derivatives. In the chemistry of
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