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Hirsutine

Names

[ CAS No. ]:
7729-23-9

[ Name ]:
Hirsutine

[Synonym ]:
Indolo[2,3-a]quinolizine-2-acetic acid, 3-ethyl-1,2,3,4,6,7,12,12b-octahydro-α-(methoxymethylene)-, methyl ester, (αE,2S,3R,12bR)-
Methyl (3β,16E)-16-(methoxymethylene)corynan-17-oate
Hirsutine
Methyl (3β,16E)-17-methoxycoryn-16-en-16-carboxylate
methyl (3β,16E)-16-(methoxymethylidene)corynan-17-oate

Biological Activity

[Description]:

Hirsutine, an indole alkaloid of Uncaria rhynchophylla, exhibits anti-cancer activity. Hirsutine induces apoptosis and is a potent Dengue virus inhibitor exhibiting low cytotoxicity[1][2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Research Areas >> Infection

[In Vitro]

Hirsutine remarkably reduces the viability of MCF-7 and MDA-MB-231 cells in a time- and dose-dependent manner with IC50 values of 447.79 and 179.06 μM, respectively. In the MDA-MB-231 cells, Hirsutine induces apoptosis and depolarization of MMP, releases Cyt C from mitochondria, and activates caspase 9 and caspase 3[2].

[In Vivo]

Hirsutine induces mPTP-dependent apoptosis through ROCK1/PTEN/PI3K/GSK3β pathway in human lung cancer cells[3].

[References]

[1]. Hishiki T, et al. Hirsutine, an Indole Alkaloid of Uncaria rhynchophylla, Inhibits Late Step in Dengue Virus Lifecycle. Front Microbiol. 2017 Aug 30;8:1674.

[2]. Huang QW, et al. [Hirsutine induces apoptosis of human breast cancer MDA-MB-231 cells through mitochondrial pathway]. Sheng Li Xue Bao. 2018 Feb 25;70(1):40-46.

[3]. Zhang R, et al. Hirsutine induces mPTP-dependent apoptosis through ROCK1/PTEN/PI3K/GSK3β pathway in human lung cancer cells. Cell Death Dis. 2018 May 22;9(6):598.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
531.7±50.0 °C at 760 mmHg

[ Melting Point ]:
101℃

[ Molecular Formula ]:
C22H28N2O3

[ Molecular Weight ]:
368.469

[ Flash Point ]:
275.4±30.1 °C

[ Exact Mass ]:
368.209991

[ PSA ]:
54.56000

[ LogP ]:
3.96

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.613

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VS3660000
CHEMICAL NAME :
17,18-Seco-3-beta-yohimban-16-carboxylic acid, 16,17-didehydro-17-methoxy-, methyl ester, (E)-
CAS REGISTRY NUMBER :
7729-23-9
LAST UPDATED :
198909
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C22-H28-N2-O3
MOLECULAR WEIGHT :
368.52

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 :
110 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 94,17,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
35 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 94,17,1989

Related Compounds