Falcarinol
(Synonyms: 人参炔醇; Panaxynol; Carotatoxin) 目录号 : GC43649
A plant defense polyacetylene
Cas No.:21852-80-2
Sample solution is provided at 25 µL, 10mM.
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- Purity: >98.00%
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Falcarinol is a C17-polyacetylene produced by the Apiaceae family that has antimicrobial properties due to its inhibition of fatty acid biosynthesis. [1] [2] Falcarinol binds to the human recombinant cannabinoid (CB) receptors, CB1 and CB2, (Kis = 594 and 2,100 nM, respectively) in an [3H]anandamide displacement assay in HEK293 cells.[3] It differentially modulates synaptic and extrasynaptic GABAA receptors in a recombinant HEK293 system. [4] In vitro assays of ATPase activity demonstrate that falcarinol inhibits breast cancer resistance protein ATP-binding cassette sub-family G member 2 (ABCG2; IC50 = 79.3 μM), a drug efflux transporter and mediator of drug resistance. [5] Falcarinol (6.88 μg/g feed) also inhibits aberrant crypt foci by 26.6% in azoxymethane-induced rats. [6]
Reference:
[1]. Dawid, C., Dunemann, F., Schwab, W., et al. Bioactive C₁₇-polyacetylenes in carrots (Daucus carota L.): Current knowledge and future perspectives. J. Agric. Food Chem. 63(42), 9211-9222 (2015).
[2]. Li, H., Cowie, A., Johnson, J.A., et al. Determining the mode of action of antimycobacterial C17 diyne natural products using expression profiling: Evidence for fatty acid biosynthesis inhibition. BMC Genomics 17(1), 621 (2016).
[3]. Leonti, M., Casu, L., Raduner, S., et al. Falcarinol is a covalent cannabinoid CB1 receptor antagonist and induces pro-allergic effects in skin. Biochem. Pharmacol. 79(12), 1815-1826 (2010).
[4]. Czyzewska, M.M., Chrobok, L., Kania, A., et al. Dietary acetylenic oxylipin falcarinol differentially modulates GABAA receptors. J. Nat. Prod. 77(12), 2671-2677 (2014).
[5]. Tan, K.W., Killeen, D.P., Li, Y., et al. Dietary polyacetylenes of the falcarinol type are inhibitors of breast cancer resistance protein (BCRP/ABCG2). Eur. J. Pharmacol. 723, 346-352 (2014).
[6]. Kobaek-Larsen, M., El-Houri, R.B., Christensen, L.P., et al. Dietary polyacetylenes, falcarinol and falcarindiol, isolated from carrots prevents the formation of neoplastic lesions in the colon of azoxymethane-induced rats. Food Funct. 8(3), 964-974 (2017).
| Cas No. | 21852-80-2 | SDF | |
| 别名 | 人参炔醇; Panaxynol; Carotatoxin | ||
| 化学名 | 1,9Z-heptadecadiene-4,6-diyn-3R-ol | ||
| Canonical SMILES | CCCCCCC/C=C\CC#CC#C[C@H](O)C=C | ||
| 分子式 | C17H24O | 分子量 | 244.4 |
| 溶解度 | DMF: 20 mg/ml; DMSO: 30 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml; Ethanol: 20 mg/ml | 储存条件 | -20°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.0917 mL | 20.4583 mL | 40.9165 mL |
| 5 mM | 0.8183 mL | 4.0917 mL | 8.1833 mL |
| 10 mM | 0.4092 mL | 2.0458 mL | 4.0917 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Quantification of the anti-neoplastic polyacetylene Falcarinol from carrots in human serum by LC-MS/MS
J Chromatogr B Analyt Technol Biomed Life Sci 2022 Nov 1;1210:123440.PMID:36088746DOI:10.1016/j.jchromb.2022.123440.
Falcarinol is a polyacetylene which is found in carrots and known to have anti-neoplastic properties in rodents. Research in the bioactivity of Falcarinol in humans require methods for quantification of Falcarinol in human serum. Here we report the development of an LC-MS/MS method and its use to measure serum Falcarinol concentrations in humans following intake of a carrot product. Falcarinol was measured by LC-MS/MS using the m/z 268 to m/z 182 mass transition. Six calibrator levels (0.2-20 ng/mL) and 3 control levels (0.4, 2 and 8 ng/mL) were prepared by addition of Falcarinol to human serum pools. Linearity of the developed method was good with a mean R2 of 0.9942. Within-day, between-day and total coefficients of variation were 6.9-13.1%, 4.1-5.0% and 8.1-14.0%, respectively. The limits of detection and quantitation were 0.1 and 0.2 ng/mL, respectively, matrix effects 84.2%, recovery 101.4-105.4% and carry-over -0.24-0.07%. Serum Falcarinol concentrations were measured in 18 healthy volunteers prior to and at 9 time-points following intake of a carrot product. Falcarinol concentrations peaked at the 1-hour time-point after intake in 15 out of 18 volunteers and declined according to a single exponential decay function with an aggregate t½ of 1.5 h. In conclusion, an LC-MS/MS method for quantification of Falcarinol in human serum with acceptable performance was developed and used to measure Falcarinol concentrations following intake of a carrot product.
Synthesis and Biological Evaluation of Falcarinol-Type Analogues as Potential Calcium Channel Blockers
J Nat Prod 2021 Aug 27;84(8):2138-2148.PMID:34319736DOI:10.1021/acs.jnatprod.1c00136.
A series of enantiomers of Falcarinol analogues (2) were synthesized using a chiral 1,1'-binaphth-2-ol (BINOL)-based catalytic system. The neuroprotective effects of Falcarinol (1a) and its analogues (2) on PC12 cells injured by sodium azide (NaN3) were investigated. The structure-function relationships and possible mechanism were studied. Pretreatment of PC12 cells with Falcarinol analogues (R)-2d and (R)-2i for 1 h following addition of NaN3 and culture in a CO2 incubator for 24 h resulted in significant elevation of cell viability, as determined by a CCK-8 assay and Hoechst staining, with reduction of LDH release and MDA content, increase of SOD activity, and decrease of ROS stress, when compared with the activity of natural Falcarinol (1a). These observations indicated that the Falcarinol analogues (R)-2d and (R)-2i can protect PC12 cells against NaN3-induced apoptosis via increasing resistance to oxidative stress. For the first time, Falcarinol (1a) and its analogue (R)-2i were found to have potential L-type calcium channel-blocking activity, as recorded using a manual patch clamp technique on HEK-293 cells stably expressing hCav1.2 (α1C/β2a/α2δ1). These findings suggest that the mechanism of the L-type calcium channel-blocking activity of Falcarinol (1a) and its analogue (R)-2i might be involved in neuroprotection by falcarinol-type analogues by inhibiting calcium overload in the upstream of the signaling pathway.
Aliphatic C(17)-polyacetylenes of the Falcarinol type as potential health promoting compounds in food plants of the Apiaceae family
Recent Pat Food Nutr Agric 2011 Jan;3(1):64-77.PMID:21114468DOI:10.2174/2212798411103010064.
Many epidemiological studies have provided evidence that a high intake of fruits and vegetables is associated with a reduced risk for the development of cancer and cardiovascular diseases. Fruits and vegetables are known to contain health promoting components such as vitamins, minerals, antioxidants and dietary fibers, however, it is unclear which of these are responsible for the health promoting properties of fruits and vegetables. Aliphatic C(17)-polyacetylenes of the Falcarinol type, which occur in common food plants of the Apiaceae family such as carrot, celeriac, parsnip and parsley, have demonstrated interesting bioactivities including antibacterial, antimycobacterial, and antifungal activity as well as anti-inflammatory, anti-platelet-aggregatory, neuritogenic and serotonergic effects. In addition, the cytotoxicity of Falcarinol type polyacetylenes towards human cancer cells, bioavailability, and their potential anticancer effect in vivo indicates that these compounds may contribute to the health effects of certain vegetables and hence could be important nutraceuticals. The bioactivity of Falcarinol type polyacetylenes occurring in food plants of the Apiaceae family, their possible mode of action and possible health promoting effects are discussed in this review as well as the effect of storage, processing and other factors that can influence the content of these compounds in particular root vegetables and products. Moreover, recent patents on bioactivity of Falcarinol type polyacetylenes and inventions making use of this knowledge are presented and discussed.
Falcarinol is a covalent cannabinoid CB1 receptor antagonist and induces pro-allergic effects in skin
Biochem Pharmacol 2010 Jun 15;79(12):1815-26.PMID:20206138DOI:10.1016/j.bcp.2010.02.015.
The skin irritant polyyne Falcarinol (panaxynol, carotatoxin) is found in carrots, parsley, celery, and in the medicinal plant Panax ginseng. In our ongoing search for new cannabinoid (CB) receptor ligands we have isolated Falcarinol from the endemic Sardinian plant Seseli praecox. We show that Falcarinol exhibits binding affinity to both human CB receptors but selectively alkylates the anandamide binding site in the CB(1) receptor (K(i)=594nM), acting as covalent inverse agonist in CB(1) receptor-transfected CHO cells. Given the inherent instability of purified Falcarinol we repeatedly isolated this compound for biological characterization and one new polyyne was characterized. In human HaCaT keratinocytes Falcarinol increased the expression of the pro-allergic chemokines IL-8 and CCL2/MCP-1 in a CB(1) receptor-dependent manner. Moreover, Falcarinol inhibited the effects of anandamide on TNF-alpha stimulated keratinocytes. In vivo, Falcarinol strongly aggravated histamine-induced oedema reactions in skin prick tests. Both effects were also obtained with the CB(1) receptor inverse agonist rimonabant, thus indicating the potential role of the CB(1) receptor in skin immunopharmacology. Our data suggest anti-allergic effects of anandamide and that falcarinol-associated dermatitis is due to antagonism of the CB(1) receptor in keratinocytes, leading to increased chemokine expression and aggravation of histamine action.
Biphasic effect of Falcarinol on caco-2 cell proliferation, DNA damage, and apoptosis
J Agric Food Chem 2007 Feb 7;55(3):618-23.PMID:17263451DOI:10.1021/jf0616154.
The polyacetylene Falcarinol, isolated from carrots, has been shown to be protective against chemically induced colon cancer development in rats, but the mechanisms are not fully understood. In this study CaCo-2 cells were exposed to Falcarinol (0.5-100 microM) and the effects on proliferation, DNA damage, and apoptosis investigated. Low-dose Falcarinol exposure (0.5-10 microM) decreased expression of the apoptosis indicator caspase-3 concomitantly with decreased basal DNA strand breakage. Cell proliferation was increased (1-10 microM), whereas cellular attachment was unaffected by <10 microM Falcarinol. At concentrations above 20 microM Falcarinol, proliferation of CaCo-2 cells decreased and the number of cells expressing active caspase-3 increased simultaneously with increased cell detachment. Furthermore, DNA single-strand breakage was significantly increased at concentrations above 10 microM Falcarinol. Thus, the effects of Falcarinol on CaCo-2 cells appear to be biphasic, inducing pro-proliferative and apoptotic characteristics at low and high concentrations of Falcarinol, respectively.