Xylopine
(Synonyms: 木番荔枝碱) 目录号 : GC64127
Xylopine 是一种阿朴啡生物碱，对癌细胞具有细胞毒活性。Xylopine 诱导氧化应激，导致癌细胞的 G2/M 细胞周期停滞和细胞凋亡 (apoptosis)。
Cas No.:517-71-5
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
Xylopine is an aporphine alkaloid with cytotoxic activity on cancer cells. Xylopine induces oxidative stress, causes G2/M cell cycle arrest and apoptosis in cancer cells[1].
Xylopine (3.5 μM-14 μM; 24-48 hours) displays potent cytotoxicity in a time- and does-depenpent manner[1].Xylopine (72 h) has cytotoxic activity, with IC50 values ranging from 6.4 to 26.6 μM in eight different cancer cell lines (MCF7, HCT116, HepG2, SCC-9, HSC-3, HL-60, K-562, and B16-F10)[1].Xylopine (3.5 μM-14 μM; 24-48 hours) causes cell cycle block at the phase G2/M, which is followed by internucleosomal DNA fragmentation[1].Xylopine (3.5 μM-14 μM; 24-48 hours) significantly increases the early and late apoptosis, induces mitochondrial depolarization, and increases caspase-3 activation[1].Xylopine also causes an increase in the production of reactive oxygen/nitrogen species (ROS/RNS), including hydrogen peroxide and nitric oxide, but not superoxide anion, and reduces glutathione levels are decreased in Xylopine-treated HCT116 cells[1].HCT116 cells[1]3.5 μM, 7 μM, and 14 μM 24 hours, 48 hoursInduced G2/M phase arrest.HCT116 cells[1]3.5 μM, 7 μM, and 14 μM 24 hours, 48 hoursSignificantly increased the early and late apoptosis.
[1]. Luciano de Souza Santos, et al. Xylopine Induces Oxidative Stress and Causes G 2/M Phase Arrest, Triggering Caspase-Mediated Apoptosis by p53-Independent Pathway in HCT116 Cells. Oxid Med Cell Longev. 2017;2017:7126872.
| Cas No. | 517-71-5 | SDF | Download SDF |
| 别名 | 木番荔枝碱 | ||
| 分子式 | C18H17NO3 | 分子量 | 295.33 |
| 溶解度 | 储存条件 | 4°C, away from moisture and 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 | 3.386 mL | 16.9302 mL | 33.8604 mL |
| 5 mM | 0.6772 mL | 3.386 mL | 6.7721 mL |
| 10 mM | 0.3386 mL | 1.693 mL | 3.386 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。
Xylopine Induces Oxidative Stress and Causes G2/M Phase Arrest, Triggering Caspase-Mediated Apoptosis by p53-Independent Pathway in HCT116 Cells
Oxid Med Cell Longev 2017;2017:7126872.PMID:29362667DOI:10.1155/2017/7126872.
Xylopine is an aporphine alkaloid that has cytotoxic activity to cancer cells. In this study, the underlying mechanism of Xylopine cytotoxicity was assessed in human colon carcinoma HCT116 cells. Xylopine displayed potent cytotoxicity in different cancer cell lines in monolayer cultures and in a 3D model of cancer multicellular spheroids formed from HCT116 cells. Typical morphology of apoptosis, cell cycle arrest in the G2/M phase, increased internucleosomal DNA fragmentation, loss of the mitochondrial transmembrane potential, and increased phosphatidylserine externalization and caspase-3 activation were observed in xylopine-treated HCT116 cells. Moreover, pretreatment with a caspase-3 inhibitor (Z-DEVD-FMK), but not with a p53 inhibitor (cyclic pifithrin-α), reduced xylopine-induced apoptosis, indicating induction of caspase-mediated apoptosis by the p53-independent pathway. Treatment with Xylopine also caused an increase in the production of reactive oxygen/nitrogen species (ROS/RNS), including hydrogen peroxide and nitric oxide, but not superoxide anion, and reduced glutathione levels were decreased in xylopine-treated HCT116 cells. Application of the antioxidant N-acetylcysteine reduced the ROS levels and xylopine-induced apoptosis, indicating activation of ROS-mediated apoptosis pathway. In conclusion, Xylopine has potent cytotoxicity to different cancer cell lines and is able to induce oxidative stress and G2/M phase arrest, triggering caspase-mediated apoptosis by the p53-independent pathway in HCT116 cells.
[Blocking actions of l-stephanine, Xylopine and 7 other tetrahydroisoquinoline alkaloids on alpha adrenoceptors]
Zhongguo Yao Li Xue Bao 1989 Jul;10(4):302-6.PMID:2576175doi
The blocking action and selectivity of 9 tetrahydroisoquinoline alkaloids on alpha adrenoceptors have been investigated in isolated tissues. Dehydrostephanine and berbamine suppressed the inhibition of clonidine for the electrically stimulated twitch response of rat vas deferens, with pA2 values of 5.36 and 5.49, respectively. l-Crebanine, l-tetrahydrocoptisine, berberine, l-stepholidine and l-tetrahydropalmatine had obvious blocking effects on alpha 1 and alpha 2 adrenoceptors. l-Stephanine and Xylopine could competitively inhibit anococcygeus muscle contraction induced by phenylephrine with pA2 values of 6.76 and 6.68, respectively. These 2 alkaloids showed no effect on the inhibition of clonidine for contractile response of rat vas deferens to field stimulation, and their selectivity ratios to block alpha 1 and alpha 2 adrenoceptors were 57.5 and 47.9, respectively. These results indicate that l-stephanine and Xylopine are 2 potent and highly selective alpha 1 adrenoceptor blockers.
Analgesic effects of the ethanolic extract from Magnolia ovata (Magnoliaceae) trunk bark and of N-acetylxylopine, a semi-synthetic analogue of Xylopine
Phytomedicine 2011 Jan 15;18(2-3):143-7.PMID:20637574DOI:10.1016/j.phymed.2010.06.001.
This study investigated the antinociceptive effects of the ethanolic extract (EEMO) obtained from Magnolia ovata (A.St.-Hil.) Spreng and N-acetylxylopine (AXyl), a stable derivative of Xylopine in different models of nociception. The EEMO and AXyl inhibited the nociception induced by acetic acid in mice, in a dose-dependent manner with a maximal inhibition of 91 ± 9% and 50 ± 11%, respectively. Oral administration of EEMO or AXyl also significantly inhibited the inflammatory phase of formalin-induced nociception with maximal reduction of 87 ± 3.9% and 71 ± 10%, respectively. Confirming the effectiveness of the extract and the isolated compound in inflammatory responses, EEMO or AXyl inhibited carrageenan-induced mechanical allodynia with percentage of inhibition of 40 ± 6% for EEMO and 82 ± 8% for AXyl. Intraplantar injection of AXyl in the ipsilateral paw, but not in the contralateral paw, also reduced carrageenan-induced mechanical allodynia in mice. The response of the animals for maximal doses tested of EEMO and AXyl in the hot-plate or rota-rod models were not altered. These results show that the extract from M. ovata and the stable derivative AXyl possess analgesic properties towards inflammatory pain acting on peripheral sites.
Natural Aporphine Alkaloids with Potential to Impact Metabolic Syndrome
Molecules 2021 Oct 10;26(20):6117.PMID:34684698DOI:10.3390/molecules26206117.
The incidence and prevalence of metabolic syndrome has steadily increased worldwide. As a major risk factor for various diseases, metabolic syndrome has come into focus in recent years. Some natural aporphine alkaloids are very promising agents in the prevention and treatment of metabolic syndrome and its components because of their wide variety of biological activities. These natural aporphine alkaloids have protective effects on the different risk factors characterizing metabolic syndrome. In this review, we highlight the activities of bioactive aporphine alkaloids: thaliporphine, boldine, nuciferine, pronuciferine, roemerine, dicentrine, magnoflorine, anonaine, apomorphine, glaucine, predicentrine, isolaureline, Xylopine, methylbulbocapnine, and crebanine. We particularly focused on their impact on metabolic syndrome and its components, including insulin resistance and type 2 diabetes mellitus, endothelial dysfunction, hypertension and cardiovascular disease, hyperlipidemia and obesity, non-alcoholic fatty liver disease, hyperuricemia and kidney damage, erectile dysfunction, central nervous system-related disorder, and intestinal microbiota dysbiosis. We also discussed the potential mechanisms of actions by aporphine alkaloids in metabolic syndrome.
[Studies on alkaloids from Fissistigma oldhamii]
Zhongguo Zhong Yao Za Zhi 2016 Aug;41(15):2838-2842.PMID:28914026DOI:10.4268/cjcmm20161516.
14 alkaloids were obtained from stems and leaves of Fissistigma oldhamii, by silica gel, ODS, Sephadex LH-20 column chromatographies, and semi-preparative HPLC. Using physicochemical and spectral methods, the isolated alkaloids were identified as norcepharadione B(1), asimilobine(2), lanuginosine(3), laurotanine(4), isocorydine(5), anolobine(6), Xylopine(7), N-methylbuxifoline(8), aristolactam AIIIa(9), piperumbellactam A(10), goniopedaline(11), aristololactam BIII(12), liriodenine(13), and salutaridine(14), respectively. Compounds 3-5, 8, 10, 11 and 14 were isolated from the genus Fissistigma for the first time.