(S)-Falcarinol
Carotatoxin；Carrotatoxin
CAS: 21852-80-2
Molecular Formula: C17H24O
(S)-Falcarinol - Names and Identifiers
(S)-Falcarinol - Physico-chemical Properties
| Molecular Formula | C17H24O |
| Molar Mass | 244.37 |
| Density | 0.931±0.06 g/cm3(Predicted) |
| Melting Point | 115°C |
| Boling Point | 115 °C(Press: 0.02 Torr) |
| Specific Rotation(α) | (c, 0.77 in CHCl3)-36.9 |
| Solubility | Soluble in methanol, ethanol, DMSO and other organic solvents |
| Appearance | Oil |
| pKa | 11.66±0.20(Predicted) |
| Storage Condition | -20℃ |
| In vitro study | Panaxynol inhibits the sphere-forming ability of NSCLC CSCs by inducing apoptosis. Panaxynol suppresses the viability of NSCLC cells with no effects on normal cells. |
(S)-Falcarinol - Reference
| Reference Show more | 1. Wang, Yi, et al. "Biophysical characterization of interactions between falcarinol-type polyacetylenes and human serum albumin via multispectroscopy and molecular docking techniques." Journal of Luminescence 200 (2018): 111-119.https://doi.org/10.1016/j.jlu 2. [IF=3.935] Shan-Shan Zhou et al."Synchronous characterization of carbohydrates and ginsenosides yields deeper insights into the processing chemistry of ginseng."J Pharmaceut Biomed. 2017 Oct;145:59 |
(S)-Falcarinol - Reference Information
| Overview | panaxynol, also known as panaxynol (falcarin01), is a polyacetylene any of a group of compounds that are widely distributed in the plant kingdom. Carthol is mainly distributed in Araliaceae, Umbelliferae, Compositae, Platycodon, haitanaceae, Oleaceae, Santalaceae, with anti-cancer, anti-bacterial, functions such as anti-fungal and nerve cell protection. Because of the instability of the light and thermal chemistry of the leaf, it is difficult to obtain the refined monomer by using the current physical and chemical means, so the research of the leaf of the leaf is late, from the mid-60s of the 20th century, it has been gradually paid attention. figure: Araliaceae plants |
| Source | in 1964, Gaoqiao sanxiong and others isolated a polyalkynyl compound monomer from Raw ginseng for the first time, designated as paecilenol, 1966, determine its chemical structure formula:(9z) a 1,9 Diene a 4,6 two acetylene one seventeen carbon A 3 alcohol, molecular weight of 244, and by chemical synthesis and Spectral determination method further confirmed. 1980 popawski et al. Reported that the content of falciparum l. In raw sun-cured ginseng was 0.03l%. In 1986, Lene Hansen et al applied preparative liquid chromatography technique to separate and purify Alcohol monomer from stems and leaves of P. Chinense, its content was 0.042%, and then purified from red ginseng and fresh ginseng root by silica gel column chromatography , the content was 0.030% and 0.006%[7J], respectively. In 2002, Lin et al, under the guidance of Golden Staphylococcus aureus growth inhibition test, isolated from Panax notoginseng of Acanthaceae, its content is 0.01%. paecilinol is also found in plants of the Araliaceae family, such as Vinca, wild carrot and saposhnikovia. |
| pharmacological effects | Anti-tumor effects: the sensitivity of cells to carthol depends to some extent on the affinity of the cells, which is more active against malignant cells than normal cells, the mode of action may be dose-dependent. Falcatol has strong inhibitory activity on human gastric adenocarcinoma cells MK-I, Hela cells and B16F10 cells in vitro. In addition, carthol is cytotoxic and can inhibit the synthesis of DNA, RNA and protein in latent lymphoid white blood cells. The cytotoxicity of falciparum is related to the chemical structure of C9 and C10 in its structural formula, which may inhibit cell proliferation by regulating cell cycle. It inhibits human malignant tumor cell SK. The molecular mechanism of MEI -1 proliferation is to increase the PIT(PIPl)(or P21' "1) and reduce the level of cdc2 protein expression, so that cell growth arrest in the G1 phase. anticoagulant effect: falcatol has obvious anticoagulant effect, the mechanism of action may be through the regulation of platelet cGMP and thromboxane A2(TXA :) levels inhibit thrombin-induced platelet aggregation, 100 mg · L. The sickle leaf carthol can completely inhibit the platelet aggregation reaction caused by collagen. inhibition of prostaglandin (PG) degradation: falcatol acts on Prostaglandin synthetase, 25-200 mmol · L, in isolated rabbit antral mucosa. Carthol has no effect on exogenous arachidonic acid synthesis of prostaglandins E:, F2 and D: But dose-dependently inhibits 15-hydroxyprostaglandin dehydrogenase (PGDH) in this concentration range the activity of this inhibition is non-competitive, it can be seen that falcatol has the effect of inhibiting the degradation of prostaglandins. antibacterial effect: falcatol on Gram-positive Staphylococcus aureus (S.aureus) and Bacillus subtilis (B. The minimum inhibitory concentration (MIC) of subtilis is 10 mg · L, respectively. And lO.5 mg • L ~, while for four gram-negative bacteria: Escherichia coli, salmonella and Pseudomonas, and yeast (yeast) had no significant inhibitory effect. Hypotensive effect: falcerol dose-dependently inhibits the vasoconstrictive response of rat aorta induced by angiotensin II. The mechanism of lowering blood pressure in spontaneously hypertensive rats (SHR) may be that the formation of Angiotensin II is affected by inhibiting the activation of lipoxygenase, which further affects the renin-angiotensin system, play a role in lowering blood pressure. sedative and analgesic effects: falcatol has strong analgesic and sedative effects, the mechanism may be related to enhancing the function of endogenous opioid peptide system in mouse brain preventing atherosclerosis: carthol reduces plasma total cholesterol and low density lipoprotein by mechanisms such as inhibiting β-hydroxyβ-methylglutaryl coenzyme A reductase (HMG-CoA), CETP and ACAT, thereby reducing the risk of cardiovascular disease such as atherosclerosis. nerve cell protection: falciparin can promote the synaptic growth of PCI2 cells, and also has a nutritional and protective effect on nerve cells, falciparin can also protect rat brain slices against oxygen-glucose deprivation and hydrogen peroxide-induced injury, but has no protective effect on glutamate-induced injury, its protective activity may be related to the increase of cAMP content in nerve cells, and the nerve cell protective activity of sickle leaf is likely to be applied to the treatment of Alzheimer's disease. figure: antineoplastic agents |
| extraction | the fat-soluble components of Panax notoginseng were extracted and purified by supercritical CO2 extraction technology, purity> 98, meeting the requirements of biochemical standard. The yield of carthol from Sickle leaf was also higher (0.077 ), which was nearly 8 times higher than that reported in (0.01). The application of supercritical technology provides a broad space for the further development of . |
| references | [1] Duan Xianchun, Wang Yongzhong, Ju Jing, etc. Research progress on carthol of sickle leaf [J]. Anhui Medical Journal, 2008, 12(1):1-3. [2] Wang Zejian, Chen Hongjia, Lu Yang. Nutritional and protective effects of carthanol on nerve cells [J]. Chinese Pharmaceutical Journal, 2005, 40(14):1073-1076. [3] Li Haiqing, Liu Rong, Zhao Qianqian, et al. Effects of falciparin on cardiac function in rats [J]. Chinese Journal of medical innovation, 2016, 13(17):1-7. [4] Jiang Liping, ni Bao-ming, Lu Hui-min, et al. Inhibitory effect and mechanism of sickle cell on proliferation of rat aortic smooth muscle cells [J]. Chinese pharmacological Bulletin, 2005, 21(11):1313-1319. [5] Duan Xianchun, Wang Yongzhong, Zhou an, et al. Extraction, isolation and identification of carthol from Panax notoginseng [J]. Journal of Anhui University of Traditional Chinese Medicine, 2008, 27(2):50-52. |
| biological activity | Falcarinol (Panaxynol) is a natural, orally active Hsp90 inhibitor, targeting the N-and C- termini of Hsp90 has limited toxicity. Falcarinol (Panaxynol) induces apoptosis. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:49:11
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