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.
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
Jonathan Roepke et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(34), 15287-15292 (2010-08-11)
The monoterpenoid indole alkaloids (MIAs) of Madagascar periwinkle (Catharanthus roseus) continue to be the most important source of natural drugs in chemotherapy treatments for a range of human cancers. These anticancer drugs are derived from the coupling of catharanthine and
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
Yoshikazu Sasaki et al.
Journal of the American Chemical Society, 132(38), 13533-13544 (2010-09-03)
Concise asymmetric total syntheses of vindoline (1) and vindorosine (2) are detailed based on a unique intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of 1,3,4-oxadiazoles inspired by the natural product structures. A chiral substituent on the tether linking the
Grégory Guirimand et al.
Journal of plant physiology, 168(6), 549-557 (2010-11-05)
Vindoline constitutes the main terpenoid indole alkaloid accumulated in leaves of Catharanthus roseus, and four genes involved in its biosynthesis have been identified. However, the spatial organization of the tabersonine-to-vindoline biosynthetic pathway is still incomplete. To pursue the characterization of
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