| Identification | Back Directory | [Name]
Hirsutine | [CAS]
7729-23-9 | [Synonyms]
16e)-
HIRSUTINE
Methyl (E)-2-[(2
corynan-16-carboxylicacid,16,17-didehydro-17-methoxy-,methylester,(3-bet
18-seco-3-beta-yohimban-16-carboxylicacid,16,17-didehydro-17-methoxy-1met
(3β,16E)-16,17-Didehydro-17-methoxycorynan-16-carboxylic acid methyl ester
(e)-16,17-didehydro-17-methoxy-17,18-seco-3-beta-yohimban-16-carboxylicacid
Methyl (E)-2-[(2S,3R,12bR)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[3,2-h]quinolizin-2-yl]-3-methoxyprop-2-enoate
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)- | [Molecular Formula]
C22H28N2O3 | [MDL Number]
MFCD01750089 | [MOL File]
7729-23-9.mol | [Molecular Weight]
368.47 |
| Chemical Properties | Back Directory | [Melting point ]
101 °C | [Boiling point ]
531.7±50.0 °C(Predicted) | [density ]
1.20±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO | [form ]
Solid | [pka]
18.13±0.60(Predicted) | [color ]
White to off-white | [InChIKey]
NMLUOJBSAYAYEM-YUPRPPKRNA-N | [SMILES]
[C@]12([H])C[C@@H]([C@@H](CC)CN1CCC1C3=C(C=CC=C3)NC2=1)/C(=C\OC)/C(=O)OC |&1:0,3,4,r| |
| Hazard Information | Back Directory | [Chemical Properties]
White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Uncaria rhynchophylla (Miq.) Miq. ex Havil. | [Uses]
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]. | [Biological Activity]
Hirsutine is a brain penetrant alkaloid from Uncaria rhynchophylla th at exhibit anti-cancercardioprotectiveanti-hypertensiveand anti-arrhythmic activities. It appears th at hirsutine induces apoptosis in lung cancer cells through opening of mitochondrial permeability transition pore (mPTP). Hirsutine exhibit potent anti-dengue virus activity. | [in vivo]
Hirsutine induces mPTP-dependent apoptosis through ROCK1/PTEN/PI3K/GSK3β pathway in human lung cancer cells[3]. | [storage]
Store at -20°C | [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. DOI:10.3389/fmicb.2017.01674
[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. PMID:29492513
[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. DOI:10.1038/s41419-018-0641-7 |
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