Dehydrocorydalin

Names

[ Name ]:
Dehydrocorydalin

[Synonym ]:
dehydrocorydalmine
dehydeocorydaline
5,6-Dihydro-2,3,9,10-tetramethoxy-13-methyldibenzo[a,g]quinolizinium
2,3,9,10-Tetramethoxy-13-methyl-5,6-dihydro-isochino[3,2-a]isochinolinylium
Dehydrocorydalin
13-Methyl-2,3,9,10-tetramethoxy-5,6-dihydrodibenzo[a,g]quinolizinium
13-methylpalmatine
2,3,9,10-tetramethoxy-13-methyl-5,6-dihydro-isoquino[3,2-a]isoquinolinylium

Biological Activity

[Description]:

Dehydrocorydaline (13-Methylpalmatine) is an alkaloid isolated from traditional Chinese herb Corydalis yanhusuo W.T. Wang. Dehydrocorydaline regulates protein expression of Bax, Bcl-2; activates caspase-7, caspase-8, and inactivates PARP.

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Bcl-2 Family

Signaling Pathways >> Apoptosis >> Caspase

Signaling Pathways >> Cell Cycle/DNA Damage >> PARP

Signaling Pathways >> Epigenetics >> PARP

Natural Products >> Alkaloid

Research Areas >> Cancer

[Target]

Bcl-2

Bax

Caspase-7

Caspase-8

PARP

[In Vitro]

Dehydrocorydaline (0-200 μM) treatment significantly inhibits the growth of MCF-7 cells in a dose-dependent manner. The cell viability is decreased by approximate 40% after 24 h of 200 μM Dehydrocorydaline[1]. Dehydrocorydaline (0-200 μM)dose-dependently increases Bax protein expression and decreases Bcl-2 protein expression[1]. Dehydrocorydaline (0-200 μM)induces activation of caspase-7,-8 and the cleavage of PARP without affecting caspase-9[1].

[In Vivo]

Dehydrocorydaline manifests a low acute toxicity with an LD50 of about 277.5±19.0 mg/kg body weight in mice following oral administration and 21.1±1.4 mg/kg for intraperitoneal injection[2].

[References]

[1]. Xu Z, et al. Dehydrocorydaline inhibits breast cancer cells proliferation by inducing apoptosis in MCF-7 cells. Am J Chin Med. 2012;40(1):177-85.

[2]. Yin ZY, et al. Antinociceptive effects of dehydrocorydaline in mouse models of inflammatory pain involve the opioid receptor and inflammatory cytokines. Sci Rep. 2016 Jun 7;6:27129.

[Related Small Molecules]

Chemical & Physical Properties

[ Melting Point ]:
170-173℃

[ Molecular Formula ]:
C₂₂H₂₄NO₄+

[ Molecular Weight ]:
366.43000

[ Exact Mass ]:
366.17100

[ PSA ]:
40.80000

[ LogP ]:
3.69320

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DR9868000

CHEMICAL NAME :: Berbinium, 7,8,13,13a-tetradehydro-2,3,9,10-tetramethoxy-13-meth yl-

CAS REGISTRY NUMBER :: 30045-16-0

BEILSTEIN REFERENCE NO. :: 1556798

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C22-H24-N-O4

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 78 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 84,73,1964

Safety Information

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Related Compounds

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