Hirsutine
Hirsutine Basic information
- Product Name:
- Hirsutine
- Synonyms:
-
- HIRSUTINE
- (e)-16,17-didehydro-17-methoxy-17,18-seco-3-beta-yohimban-16-carboxylicacid
- 16e)-
- 18-seco-3-beta-yohimban-16-carboxylicacid,16,17-didehydro-17-methoxy-1met
- corynan-16-carboxylicacid,16,17-didehydro-17-methoxy-,methylester,(3-bet
- 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
- (3β,16E)-16,17-Didehydro-17-methoxycorynan-16-carboxylic acid methyl ester
- Methyl (E)-2-[(2
- CAS:
- 7729-23-9
- MF:
- C22H28N2O3
- MW:
- 368.47
- Mol File:
- 7729-23-9.mol
Hirsutine Chemical Properties
- 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|
Hirsutine Usage And Synthesis
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-cancer, cardioprotective, anti-hypertensive, and 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].
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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