Vindoline

Names

[ Name ]:
Vindoline

[Synonym ]:
Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2β,4β,5α,12β,19α)-
methyl (2β,3β,4β,5α,12β,19α)-4-(acetyloxy)-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
Vindoline
4-acetoxy-3-hydroxy-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester
(2b,3b,4b,5a,12b,19a)-4-(Acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylic Acid Methyl Ester
Methyl (2β,4β,5α,12β,19α)-4-acetoxy-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
Vindoline (8CI)
vindolin
EINECS 218-558-0
Vindoline, (-)-

Biological Activity

[Description]:

Vindoline, a vinca alkaloid extracted from the leaves of Catharanthus roseus, weakly inhibits tubulin self-assembly[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin

Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

[References]

[1]. Prakash V, et al. Mechanism of interaction of vinca alkaloids with tubulin: catharanthine and vindoline. Biochemistry. 1991 Jan 22;30(3):873-80.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
569.8±50.0 °C at 760 mmHg

[ Melting Point ]:
163-165ºC

[ Molecular Formula ]:
C₂₅H₃₂N₂O₆

[ Molecular Weight ]:
456.531

[ Flash Point ]:
298.4±30.1 °C

[ Exact Mass ]:
456.226044

[ PSA ]:
88.54000

[ LogP ]:
2.20

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.626

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CJ0120000

CHEMICAL NAME :: Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1- methyl-, methyl ester, (2-beta,3-beta,4-beta,5-alpha,12-beta,19-alpha)-

CAS REGISTRY NUMBER :: 2182-14-1

LAST UPDATED :: 198009

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C25-H32-N2-O6

MOLECULAR WEIGHT :: 456.59

WISWESSER LINE NOTATION :: T C6 B5665 2AB S BX IN QN NU JH&&TTTJ FO1 I1 KVO1 KQ LOV1 M2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - excitement

REFERENCE :: 33GVAL "Catharanthus Alkaloids," Taylor, W.I., and N.R. Farnsworth, eds., New York, Marcel Dekker, 1975 Volume(issue)/page/year: -,73,1975

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H341

[ Precautionary Statements ]:
P281

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
68

[ Safety Phrases ]:
36/37-24/25

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
CJ0120000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Increased availability of tryptophan in 5-methyltryptophan-tolerant shoots of Catharanthus roseus and their postharvest in vivo elicitation induces enhanced vindoline production.

Appl. Biochem. Biotechnol. 168(3) , 568-79, (2012)

Ten 5-methyltryprophan (5-MT)-resistant multiple shoot culture lines in three genotypes of Catharanthus roseus were selected in vitro. The variant shoot lines displayed a differential threshold tolera...

Simultaneous determination of vinblastine and its monomeric precursors vindoline and catharanthine in Catharanthus roseus by capillary electrophoresis-mass spectrometry.

J. Sep. Sci. 34 , 2885-2892, (2011)

Catharanthus roseus is an important dicotyledonous medicinal plant that contains various anticancer components, such as vinblastine (VLB) and its monomeric precursors (vindoline and catharanthine). A ...

Catharanthine C16 substituent effects on the biomimetic coupling with vindoline: preparation and evaluation of a key series of vinblastine analogues.

Bioorg. Med. Chem. Lett. 20(22) , 6408-10, (2010)

The examination of the catharanthine C16 substituent effects on the Fe(III)-promoted biomimetic coupling reaction with vindoline is detailed, confirming the importance of the presence of a C16 electro...

Related Compounds

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