Secologanin

Names

[ CAS No. ]:
19351-63-4

[ Name ]:
Secologanin

[Synonym ]:
loniceroside
secologanin

Biological Activity

[Description]:

Secologanin, a secoiridoid glucoside, is a pivotal terpenoid intermediate in the biosynthesis of biologically active monoterpenoid indole alkaloids such as reserpine, ajmaline, and vinblastine. Secologanin synthase (cytochrome P450 isoform CYP72A1) catalyzes the oxidative cleavage of loganin into Secologanin[1][2].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[References]

[1]. Inoue K. Yakugaku Zasshi. 2005;125(1):31-49. doi:10.1248/yakushi.125.31

[2]. Irmler S, et al. Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase. Plant J. 2000;24(6):797-804.

Chemical & Physical Properties

[ Density]:
1.42g/cm3

[ Boiling Point ]:
595.5ºC at 760mmHg

[ Molecular Formula ]:
C₁₇H₂₄O₁₀

[ Molecular Weight ]:
507.74400

[ Flash Point ]:
212.2ºC

[ Exact Mass ]:
506.05100

[ PSA ]:
151.98000

[ LogP ]:
0.20990

[ Vapour Pressure ]:
1.15E-16mmHg at 25°C

[ Index of Refraction ]:
1.571

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Precursor & DownStream

Precursor

DownStream

Articles

The leaf epidermome of Catharanthus roseus reveals its biochemical specialization.

Plant Cell 20(3) , 524-42, (2008)

Catharanthus roseus is the sole commercial source of the monoterpenoid indole alkaloids (MIAs), vindoline and catharanthine, components of the commercially important anticancer dimers, vinblastine and...

2,4-D and alkaloid accumulation in periwinkle cell suspensions.

Biochimie 76(5) , 410-6, (1994)

Omission of 2,4-D from culture medium during one subculture of Catharanthus roseus cells, strain C20, resulted in an increased alkaloid accumulation, without effect on growth. Alkaloid accumulation, r...

Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase.

Plant J. 24 , 797, (2000)

The molecular characterization of CYP72A1 from Catharanthus roseus (Madagascar periwinkle) was described nearly a decade ago, but the enzyme function remained unknown. We now show by in situ hybridiza...