Taraxerol
(Synonyms: 蒲公英萜醇) 目录号 : GC60352
Taraxerol 具有抗炎和抗癌作用。
Cas No.:127-22-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
| Cell experiment [1]: | |
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Cell lines |
RAW264.7 macrophages |
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Preparation Method |
The cells were treated with various concentrations of taraxerol or LPS plus taraxerol for 24 h. Then cells were incubated with 5 mg/ml of MTT working solution for 4 h at 37°C. After being treated with 100 µl of DMSO to dissolve the crystals, the cells were detected under an ELx800 Universal Microplate Reader to measure the absorbance at 570 nm. |
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Reaction Conditions |
0、10、20、40 μM Taraxerol for 1h |
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Applications |
Taraxerol downregulates the expression of proinflammatory mediators in macrophages by interfering with the activation of TAK1 and Akt, thus preventing NF-κB activation. |
| Animal experiment [2]: | |
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Animal models |
Wistar rats (♂, 150 ± 20 g) |
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Preparation Method |
groups were treated with taraxerol at the doses of 5 and 10 mg/kg, i.p., respectively. |
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Dosage form |
5 and 10 mg/kg Taraxerol for 0-4h |
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Applications |
Taraxerol treatment significantly attenuated carrageenan induced paw edema 2 h onward. The anti-inflammatory effect of taraxerol was sustained up to 4 h. |
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References: [1]. Yao X, Li G, et,al. Taraxerol inhibits LPS-induced inflammatory responses through suppression of TAK1 and Akt activation. Int Immunopharmacol. 2013 Feb;15(2):316-24. doi: 10.1016/j.intimp.2012.12.032. Epub 2013 Jan 15. PMID: 23333629. |
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Taraxerol has anti-inflammatory and anticancer effects. Taraxerol attenuates acute inflammation by inhibiting NF-κB signaling[5,6].
Taraxerol downregulates the expression of proinflammatory mediators in macrophages by interfering with the activation of TAK1 and Akt, thus preventing NF-κB activation[3].
Taraxerol enhanced ROS levels and attenuated the MMP (Δψm) in HeLa cells. Taraxerol induced apoptosis mainly via the mitochondrial pathway including the release of cytochrome c to the cytosol and activation of caspases 9 and 3, and anti-poly (ADPribose) polymerase (PARP). Taraxerol could induce the down-regulation of the anti-apoptotic protein Bcl-2 and up-regulation of pro-apoptotic protein Bax. It suppressed the PI3K/ Akt signaling pathway [1].
Taraxerol treatment significantly attenuated carrageenan induced paw edema 2 h onward. The anti-inflammatory effect of taraxerol was sustained up to 4 h[2]. Taraxerol (20mg/kg, p.o.) treatment stimulated glucose metabolism in skeletal muscle, regulated blood glycaemic status and lipid profile in the sera, reduced the secretion of pro-inflammatory cytokines, and restored the renal physiology in T2D rats[4]. AChE activity inhibition in animals and indicate that Taraxerol has anti-amnesic activity that may hold significant therapeutic value in alleviating certain memory impairments observed in AD[7].
References:
[1]: Yaoi X, Lu B, et,al. Taraxerol Induces Cell Apoptosis through A Mitochondria-Mediated Pathway in HeLa Cells. Cell J. 2017 Oct;19(3):512-519. doi: 10.22074/cellj.2017.4543. Epub 2017 Aug 19. PMID: 28836414; PMCID: PMC5572297.
[2]: Khanra R, Dewanjee S, et,al. Taraxerol, a pentacyclic triterpene from Abroma augusta leaf, attenuates acute inflammation via inhibition of NF-κB signaling. Biomed Pharmacother. 2017 Apr;88:918-923. doi: 10.1016/j.biopha.2017.01.132. Epub 2017 Feb 6. PMID: 28178622.
[3]: Yao X, Li G, et,al. Taraxerol inhibits LPS-induced inflammatory responses through suppression of TAK1 and Akt activation. Int Immunopharmacol. 2013 Feb;15(2):316-24. doi: 10.1016/j.intimp.2012.12.032. Epub 2013 Jan 15. PMID: 23333629.
[4]: Khanra R, Bhattacharjee N, et,al. Taraxerol, a pentacyclic triterpenoid, from Abroma augusta leaf attenuates diabetic nephropathy in type 2 diabetic rats. Biomed Pharmacother. 2017 Oct;94:726-741. doi: 10.1016/j.biopha.2017.07.112. Epub 2017 Aug 9. PMID: 28802226.
[5]: Khanra R, Dewanjee S, et,al. (Malvaceae) leaf extract attenuates diabetes induced nephropathy and cardiomyopathy via inhibition of oxidative stress and inflammatory response. J Transl Med. 2015 Jan 16;13:6. doi: 10.1186/s12967-014-0364-1. PMID: 25591455; PMCID: PMC4301895.
[6]: Tsao CC, Shen YC, et,al. New diterpenoids and the bioactivity of Erythrophleum fordii. Bioorg Med Chem. 2008 Nov 15;16(22):9867-70. doi: 10.1016/j.bmc.2008.09.021. Epub 2008 Sep 12. PMID: 18926710.
[7]: Berté TE, Dalmagro AP, Zimath PL, Gon?alves AE, Meyre-Silva C, Bürger C, Weber CJ, Dos Santos DA, Cechinel-Filho V, de Souza MM. Taraxerol as a possible therapeutic agent on memory impairments and Alzheimer's disease: Effects against scopolamine and streptozotocin-induced cognitive dysfunctions. Steroids. 2018 Apr;132:5-11. doi: 10.1016/j.steroids.2018.01.002. PMID: 29355563.
Taraxerol 具有抗炎和抗癌作用。蒲公英甾醇通过抑制 NF-κB 信号通路减轻急性炎症[5,6]。
紫杉醇通过干扰 TAK1 和 Akt 的激活来下调巨噬细胞中促炎介质的表达，从而阻止 NF-κB 激活[3]。
紫杉醇增强了 HeLa 细胞中的 ROS 水平并减弱了 MMP (δψm)。 Taraxerol 主要通过线粒体途径诱导细胞凋亡，包括将细胞色素 c 释放到胞质溶胶和半胱天冬酶 9 和 3 的激活，以及抗多聚 (ADPribose) 聚合酶 (PARP)。 Taraxerol 可诱导抗凋亡蛋白 Bcl-2 的下调和促凋亡蛋白 Bax 的上调。抑制PI3K/Akt信号通路[1]。
2 小时后，紫杉醇处理可显着减轻角叉菜胶诱导的爪水肿。蒲公英甾醇的抗炎作用可持续长达4 h[2]。蒲公英甾醇（20 毫克/千克，口服）治疗可刺激骨骼肌中的葡萄糖代谢，调节血糖状态和血清中的脂质分布，减少促炎细胞因子的分泌，并恢复 T2D 大鼠的肾脏生理机能[4] 。动物 AChE 活性抑制表明 Taraxerol 具有抗遗忘活性，在减轻 AD[7] 中观察到的某些记忆障碍方面可能具有重要的治疗价值。
| Cas No. | 127-22-0 | SDF | |
| 别名 | 蒲公英萜醇 | ||
| Canonical SMILES | C[C@]12C3=CC[C@@](C)(CCC(C)(C)C4)[C@]4([H])[C@@]3(CC[C@]1([H])[C@@]5([C@@](C(C)([C@@H](O)CC5)C)([H])CC2)C)C | ||
| 分子式 | C30H50O | 分子量 | 426.72 |
| 溶解度 | ≥ 40 mg/mL in DMSO | 储存条件 | 4°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 | 2.3435 mL | 11.7173 mL | 23.4346 mL |
| 5 mM | 0.4687 mL | 2.3435 mL | 4.6869 mL |
| 10 mM | 0.2343 mL | 1.1717 mL | 2.3435 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。
The Biosynthesis and Medicinal Properties of Taraxerol
Biomedicines 2022 Mar 30;10(4):807.PMID:35453556DOI:10.3390/biomedicines10040807.
Taraxerol is a pentacyclic triterpenoid that is actively produced by some higher plants as part of a defense mechanism. The biosynthesis of Taraxerol in plants occurs through the mevalonate pathway in the cytosol, in which dimethylallyl diphosphate (DMAPP) and isopentyl pyrophosphate (IPP) are first produced, followed by squalene. Squalene is the primary precursor for the synthesis of triterpenoids, including Taraxerol, β-amyrin, and lupeol, which are catalyzed by Taraxerol synthase. Taraxerol has been extensively investigated for its medicinal and pharmacological properties, and various biotechnological approaches have been established to produce this compound using in vitro techniques. This review provides an in-depth summary of the hypothesized Taraxerol biosynthetic pathway, the medicinal properties of Taraxerol, and recent developments on tissue culture for the in vitro production of Taraxerol.
Heterologous biosynthesis of Taraxerol by engineered Saccharomyces cerevisiae
FEMS Microbiol Lett 2022 Aug 16;369(1):fnac070.PMID:35896500DOI:10.1093/femsle/fnac070.
Taraxerol is an oleanane-type pentacyclic triterpenoid compound distributed in many plant species that has good effects on the treatment of inflammation and tumors. However, the Taraxerol content in medicinal plants is low, and chemical extraction requires considerable energy and time, so Taraxerol production is a problem. It is a promising strategy to produce Taraxerol by applying recombinant microorganisms. In this study, a Saccharomyces cerevisiae strain WKde2 was constructed to produce Taraxerol with a titer of 1.85 mg·l-1, and the Taraxerol titer was further increased to 12.51 mg·l-1 through multiple metabolic engineering strategies. The endoplasmic reticulum (ER) size regulatory factor INO2, which was reported to increase squalene and cytochrome P450-mediated 2,3-oxidosqualene production, was overexpressed in this study, and the resultant strain WTK11 showed a Taraxerol titer of 17.35 mg·l-1. Eventually, the highest reported titer of 59.55 mg·l-1 Taraxerol was achieved in a 5 l bioreactor. These results will serve as a general strategy for the production of other triterpenoids in yeast.
Taraxerol Induces Cell Apoptosis through A Mitochondria-Mediated Pathway in HeLa Cells
Cell J 2017 Oct;19(3):512-519.PMID:28836414DOI:10.22074/cellj.2017.4543.
Objectives: Taraxerol acetate has potent anti-cancer effects via the induction of apoptosis, autophagy, cell cycle arrest, and inhibition of cell migration. However, whether Taraxerol induced apoptosis and its underlying mechanisms of action is not clear. In the present study, we assess the effects of Taraxerol on the mitochondrial apoptotic pathway and determine the release of cytochrome c to the cytosol and activation of caspases. Materials and methods: In this experimental study, we mainly investigated the effect of Taraxerol on HeLa cells. We tested cell viability by the MTT assay and morphologic changes, analyzed apoptosis by DAPI staining and flow cytometry. We also determined reactive oxygen species (ROS) and mitochondrial membrane potential (MMP) using a Microplate Reader. In addition, the apoptotic proteins were tested by Western blot. Results: Taraxerol enhanced ROS levels and attenuated the MMP (Δψm) in HeLa cells. Taraxerol induced apoptosis mainly via the mitochondrial pathway including the release of cytochrome c to the cytosol and activation of caspases 9 and 3, and anti-poly (ADPribose) polymerase (PARP). Taraxerol could induce the down-regulation of the anti-apoptotic protein Bcl-2 and up-regulation of pro-apoptotic protein Bax. It suppressed the PI3K/ Akt signaling pathway. Conclusions: These results demonstrated that Taraxerol induced cell apoptosis through a mitochondria-mediated pathway in HeLa cells. Thus, Taraxerol might be a potential anticervical cancer candidate.
Occurrence of Taraxerol and taraxasterol in medicinal plants
Pharmacogn Rev 2015 Jan-Jun;9(17):19-23.PMID:26009688DOI:10.4103/0973-7847.156317.
Indian soil germinates thousands of medicinal drugs that are cultivated with a purpose to obtain a novel drug. As it is a well-established fact that the structural analogs with greater pharmacological activity and fewer side-effects may be generated by the molecular modification of the functional groups of such lead compounds. This review throws light on two natural triterpenes - Taraxerol and Taraxasterol which have many important pharmacological actions including anti-cancer activity, their chemistry, biosynthesis aspects, and possible use of these compounds as drugs in treatment of cancer. A silent crisis persists in cancer treatment in developing countries, and it is intensifying every year. Although at least 50-60% of cancer victims can benefit from radiotherapy that destroys cancerous tumors, but search for the paramount therapy which will prove to be inexpensive with minimal side effects still persists. Various treatment modalities have been prescribed, along with conventional and non-conventional medicine but due to their adverse effects and dissatisfaction among users, these treatments are not satisfactory enough to give relief to patients. Hence, this review sparks the occurrence of Taraxerol (VI) and Taraxasterol (VII) in nature, so that the natural godowns may be harvested to obtain these potent compounds for novel drug development as well as discusses limitations of these lead compounds progressing clinical trials.
Taraxerol, a pentacyclic triterpene from Abroma augusta leaf, attenuates acute inflammation via inhibition of NF-κB signaling
Biomed Pharmacother 2017 Apr;88:918-923.PMID:28178622DOI:10.1016/j.biopha.2017.01.132.
Abroma augusta L. (Malvaceae) leaf is traditionally used to treat inflammatory disorders. In our laboratory, we have scientifically validated the anti-inflammatory effect of A. augusta leaf extract. In this study, it has been aimed to evaluate in vivo anti-inflammatory effect of Taraxerol isolated from the methanol extract of A. augusta leaf. It was further intended to find out the probable mechanism of anti-inflammatory effect of Taraxerol. The anti-inflammatory effect of Taraxerol (5 and 10mg/kg, i.p.) was measured employing carrageenan-induced paw edema model of acute inflammation. The carrageenan injection resulted significant edema formation in the right paw when compared with un-injected left paw. However, Taraxerol (10mg/kg) treatment could significantly (p<0.05-0.01) attenuate carrageenan induced paw edema 2h onward. The effect of Taraxerol at the dose of 5mg/kg was found to be significant (p<0.05) only after 4h of carrageenan treatment. Taraxerol (10mg/kg) treatment could significantly (p<0.01) attenuate carrageenan mediated up-regulation in the levels of IL 1β, IL 6, IL 12 and TNF α in the right paw tissues. In search of molecular mechanism, Taraxerol (10mg/kg) could significantly (p<0.05-0.01) reinstate carrageenan provoked NF-κB signaling and thereby caused significant down-regulation in the expressions of COX-2 (p<0.01) and iNOS (p<0.05). In conclusion, Taraxerol would attenuate acute inflammation via inhibition of NF-κB signaling.