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Heliosupine

Names

[ CAS No. ]:
32728-78-2

[ Name ]:
Heliosupine

[Synonym ]:
Cynoglossofine
7-Angelyl-9-echimidinylheliotridine
HELIOSUPINE
Heliosupin
Cynoglossophine
[(7S,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2,3-dihydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
Cynoglossofin

Biological Activity

[Description]:

Heliosupine is a pyrrolizidine alkaloid. Heliosupine is an acetylcholinesterase (AChE) inhibitor, with an IC50 0.57 mM. Heliosupine exhibits deterrent effects against generalist herbivores[1][2].

[Related Catalog]:

Research Areas >> Others
Signaling Pathways >> Neuronal Signaling >> AChE

[Target]

IC50: 0.57 mM (AChE)[1]


[In Vivo]

Heliosupine prevents feeding by the polyphagous larvae of Spodoptera exigua[2].

[References]

[1]. Benamar H, et, al. Pyrrolizidine alkaloids from Solenanthus lanatus DC. with acetylcholinesterase inhibitory activity. Nat Prod Res. 2016 Nov;30(22):2567-2574.

[2]. Dam NM, et, al. The "Raison D'être" of pyrrolizidine alkaloids in Cynoglossum officinale: Deterrent effects against generalist herbivores. J Chem Ecol. 1995 May;21(5):507-23.

Chemical & Physical Properties

[ Density]:
1.26g/cm3

[ Boiling Point ]:
535.7ºC at 760mmHg

[ Molecular Formula ]:
C20H31NO7

[ Molecular Weight ]:
397.46300

[ Flash Point ]:
277.8ºC

[ Exact Mass ]:
397.21000

[ PSA ]:
116.53000

[ LogP ]:
0.24260

[ Index of Refraction ]:
1.565

Related Compounds