Cucurbitacin IIa
(Synonyms: 葫芦素IIA,Hemslecin A) 目录号 : GC35758
Curcurbitacin IIA (Cucurbitacin Iia, CuIIa, Hemslecin A, Dihydrocucurbitacin Q1) is the major active component of the Helmseya amabilis root and is known to have antiviral and anti-inflammatory effects.
Cas No.:58546-34-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Curcurbitacin IIA (Cucurbitacin Iia, CuIIa, Hemslecin A, Dihydrocucurbitacin Q1) is the major active component of the Helmseya amabilis root and is known to have antiviral and anti-inflammatory effects.
| Cas No. | 58546-34-2 | SDF | |
| 别名 | 葫芦素IIA,Hemslecin A | ||
| Canonical SMILES | C[C@@]([C@@](CC=C1[C@@]2([H])C[C@H](O)[C@@H](O)C1(C)C)([H])[C@@]2(C)C3=O)(C[C@@H](O)[C@]4([H])[C@@](C)(O)C(CCC(C)(C)OC(C)=O)=O)[C@@]4(C3)C | ||
| 分子式 | C32H50O8 | 分子量 | 562.73 |
| 溶解度 | Soluble 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 | 1.7771 mL | 8.8853 mL | 17.7705 mL |
| 5 mM | 0.3554 mL | 1.7771 mL | 3.5541 mL |
| 10 mM | 0.1777 mL | 0.8885 mL | 1.7771 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。
Cucurbitacin IIa: A review of phytochemistry and pharmacology
Phytother Res 2021 Aug;35(8):4155-4170.PMID:33724593DOI:10.1002/ptr.7077.
Cucurbitacin IIa was first found in plants and it belongs to tetracyclo triterpenoids. It is one of the most important active components in cucurbitaceae plants. Studies have found that Cucurbitacin IIa has a variety of pharmacological effects, such as antitumor, antiinflammatory, antibacterial, antihepatitis B virus, inhibition of human immunodeficiency virus replication, and antidepressant effect. However, the underlying mechanisms, intracellular targets, and structure-activity relationships of Cucurbitacin IIa remain to be completely elucidated. This review summarizes the current advances concerning the phytochemistry and pharmacology of Cucurbitacin IIa. Electronic databases such as PubMed, Web of Science, Google Scholar, Science Direct, and CNKI were used to find relevant information about Cucurbitacin IIa using keywords such as "Cucurbitacin IIa," "Pharmacology," and "Phytochemistry." These pharmacological effects involve the actin cytoskeleton aggregation, the regulation of JAK2/STAT3, ERBB-MAPK, CaMKII α/CREB/BDNF signal pathways, as well as the regulation of survivin, caspases, and other cell cycles, apoptosis, autophagy-related cytokines, and kinases. It has high development and use value.
Comparative transcriptome analysis and identification of candidate genes involved in Cucurbitacin IIa biosynthesis in Hemsleya macrosperma
Plant Physiol Biochem 2022 Aug 15;185:314-324.PMID:35738187DOI:10.1016/j.plaphy.2022.06.014.
Hemsleya macrosperma (H. macrosperma) is widely used in southwestern China as folk medicine with various bioactivities. Cucurbitacin IIa is the main active component in H. macrosperma and draws increased attention for its potential pharmacological activities. In order to reveal the mechanism of Cucurbitacin IIa biosynthesis and regulation in H. macrosperma, transcriptome analysis was performed to compare differentially expressed genes in three tissues (root tuber, stem and leaf). A total of 47 946 unigenes were generated from these tissues and 55 unigenes were identified as candidate genes involved in triterpenoid backbone biosynthesis. Three homologous genes encoding squalene epoxidase (HmSE) were discovered and successfully expressed in a prokaryotic system. HmSE1 was found to be responsible for oxidization of squalene. In addition, several cytochrome P450s and transcription factors were predicted as candidates associated to Cucurbitacin IIa biosynthesis. Notably, the expression profiles of those putative genes showed a positive correlation with elevated curcurbitacin IIa production in methyl jasmonate-elicited suspension cells of H. macrosperma., suggesting probable functions of the candidates on curcurbitacin IIa biosynthesis. These findings provide insights on Cucurbitacin IIa biosynthesis and regulation in H. macrosperma.
Cucurbitacin IIa interferes with EGFR-MAPK signaling pathway leads to proliferation inhibition in A549 cells
Food Chem Toxicol 2019 Oct;132:110654.PMID:31265865DOI:10.1016/j.fct.2019.110654.
Cucurbitacin IIa (CuIIa), a tetracyclic triterpenoid harboring anticancer activity, was investigated in A549 cells to reveal its mechanism of targeting on epidermal growth factor receptor (EGFR) signaling pathway. Results showed that CuIIa was capable of inducing apoptosis and cell cycle arrest at G2/M phase. The transcription of EGFR pathway genes and their proteins accumulation was inconsistently influenced by CuIIa. Notably, transcription of Raf1 was significantly upregulated, nevertheless, MEK1 and ERK1 were significantly downregulated. On the other hand, the accumulation of the total and phosphorylated proteins of the most members in EGFR-mitogen-activated protein kinase (MAPK) pathway, as well as CylclinB1 and survivin were also shifted by CuIIa treatment. Remarkably, total MEK remained constant but survivin completely degraded. Moreover, phosphorylated BRAF continuously increased while Raf1 and MEK decreased continuously. CuIIa was further confirmed to be a tyrosine kinase inhibitor (TKI) of EGFR by kinase inhibition assay. The results of molecular simulation showed that the long side chain of CuIIa occupied the binding pocket of EGFR and the ligand was stabilized at the active site of EGFR. In view of the results above, it is suggested that CuIIa inhibits cell proliferation by interfering the EGFR-MAPK signaling pathway.
Synthesis of Cucurbitacin IIa derivatives with apoptosis-inducing capabilities in human cancer cells
RSC Adv 2020 Jan 23;10(7):3872-3881.PMID:35492669DOI:10.1039/c9ra09113k.
Twenty-one Cucurbitacin IIa derivatives were synthesized and screened for cytotoxic activity. Their structures were established using 1H NMR, 13C NMR, and LC-MS spectroscopic data. The absolute configuration of the derivatives was determined by single crystal diffraction. In sulforhodamine B (SRB) assays, nearly all compounds displayed low cytotoxicity toward normal human cells (HEK293). However, some derivatives displayed high cytotoxicity, in the low μM range, toward several human tumor cell lines (SKOV3, HT29, HEPG2, MCF-7, and LOVO). Low IC50 values were obtained, especially for acetyl-protected product 2, 2,4,6-trichlorophenylhydrazine derivative 4a, and 2-hydrazinopyridine derivative 4d. In particular, compounds 2 and 4d showed low IC50 values of 1.2 ± 0.01 and 2.2 ± 0.19 μM against SKOV3 cells. These compounds were submitted to extensive biological testing, which showed that compounds 2 and 4a did not inhibit tumor cells by influencing the cell cycle. Furthermore, compound 4a triggered the apoptotic pathway in cancer cells, showing high apoptosis ratios. This study mainly changed the structure of cucurbitacin tetracyclic triterpenoids and provided a novel tetracyclic skeleton derived from natural products that provided further references for the future modification of cucurbitacin tetracyclic triterpenoids.
Cucurbitacin IIa exerts antidepressant-like effects on mice exposed to chronic unpredictable mild stress
Neuroreport 2017 Mar 22;28(5):259-267.PMID:28240721DOI:10.1097/WNR.0000000000000747.
Cucurbitacin IIa (CuIIa) is the major active component of the Helmseya amabilis root and is known to have antiviral and anti-inflammatory effects. In this study, we examined the antidepressant-like effects of CuIIa in a mouse model of chronic unpredictable mild stress (CUMS) and investigated the possible underlying mechanisms. To evaluate the antidepressant-like effects of CuIIa on depression-like behaviors, mice were subjected to the open-field test, the elevated plus-maze test, the forced-swimming test, and the tail-suspension test. We found that CuIIa treatment reversed the CUMS-induced behavioral abnormalities. Western blot analyses showed that CUMS significantly decreased brain-derived neurotrophic factor (BDNF) levels, cAMP-response element binding protein (CREB), and calcium/calmodulin-dependent protein kinase II (CaMKII) phosphorylation, and N-methyl-D-aspartate receptor subtype GluN2B and α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor GluA1 expression in the amygdala; in addition, the expression of gamma-aminobutyric acid receptor A subunit α2 was upregulated in CUMS mice. These CUMS-induced changes were all normalized by CuIIa treatment and administration of the BDNF antagonist ANA-12 can block the antidepressant effect of CuIIa. Our findings suggest that the antidepressant-like effects of CuIIa may be exerted by regulation of the CaMKIIα-CREB-BDNF pathway and the balance between excitatory and inhibitory synaptic transmission in the amygdala.