Tuberostemonine
(Synonyms: 对叶百部碱) 目录号 : GC61360
An alkaloid with diverse biological activities
Cas No.:6879-01-2
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
Tuberostemonine is an alkaloid that has been found in S. tuberosa and has diverse biological activities.1,2,3 It exhibits feeding deterrent and repellant activities against S. littoralis fifth instar larvae when applied to lettuce leaf disks at concentrations of 0.01 and 0.1 ?g/cm2, respectively.1 Tuberostemonine (100 mg/kg) reduces the number of citric acid-induced coughs in guinea pigs.2 In vivo, tuberostemonine (1-10 mg/kg) decreases bronchoalveolar lavage fluid (BALF) neutrophil and macrophage, but not lymphocyte, infiltration and reduces peribronchial and perivascular inflammatory cell infiltration in a cigarette smoke-induced mouse model of acute lung inflammation.3
1.Brem, B., Seger, C., Pacher, T., et al.Feeding deterrence and contact toxicity of Stemona alkaloids-a source of potent natural insecticidesJ. Agric. Food Chem.50(22)6383-6388(2002) 2.Zhou, X., Leung, P.H.H., Li, N., et al.Oral absorption and antitussive activity of tuberostemonine alkaloids from the roots of Stemona tuberosaPlanta Med.75(6)575-580(2009) 3.Jung, K.-H., Beak, H., Park, S., et al.The therapeutic effects of tuberostemonine against cigarette smoke-induced acute lung inflammation in miceEur. J. Pharmacol.77480-86(2016)
| Cas No. | 6879-01-2 | SDF | |
| 别名 | 对叶百部碱 | ||
| Canonical SMILES | [H][C@@]([C@]1([H])[C@@]23[H])(CCCCN1[C@]([H])([C@@]4([H])OC([C@@H](C)C4)=O)C3)[C@@H](CC)[C@]([C@]2([H])[C@@H]5C)([H])OC5=O | ||
| 分子式 | C22H33NO4 | 分子量 | 375.5 |
| 溶解度 | 储存条件 | Store at -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 | 2.6631 mL | 13.3156 mL | 26.6312 mL |
| 5 mM | 0.5326 mL | 2.6631 mL | 5.3262 mL |
| 10 mM | 0.2663 mL | 1.3316 mL | 2.6631 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。
Tuberostemonine reverses multidrug resistance in chronic myelogenous leukemia cells K562/ADR
J Cancer 2017 Apr 9;8(6):1103-1112.PMID:28529625DOI:10.7150/jca.17688.
Objective: To investigate the reversal effect of Tuberostemonine on MDR in myelogenous leukemia cells K562/ADR. Methods: Human myelogenous leukemia cells K562 and their adriamycin-resistance cells K562/ADR were used. The growth curve of cells treated by Tuberostemonine and the Non-toxic concentration of Tuberostemonine were determined by MTT, Cell apoptosis was determined by MTT and flow cytometry. The expression of MDR1, Survivin and Livin was detected by RT-PCR. The activity of P-gp was detected by flow cytometry. Western blot was used to detect the expression of NF-κB and Survivin. Results: The effect of Tuberostemonine on K562/ADR showed a dose-dependence, and 350μg/mL and 500μg/mL of Tuberostemonine could inhibit the expression of MDR1 (P<0.05). While no function difference of P-gp was detected. With the increased concentration of Tuberostemonine, the inhibitory effect were enhanced to the expression of NF-κB. Tuberostemonine combined with adriamycin could time-dependently inhibit the cell proliferation (P<0.05) and obviously promoted the cell apoptosis (P<0.05). Also the Tuberostemonine could inhibit the expression of Survivin. Conclusion: There are no direct relations between Tuberostemonine and P-gp, but Tuberostemonine could reverse the multidrug resistance of K562/ADR via down-regulating the expression of Nf-κB and inhibiting th1e expression of Survivin.
Structural Revision of the Stemona Alkaloids Tuberostemonine O, Dehydrocroomines A and B, and Dehydrocroomine
J Nat Prod 2022 Aug 26;85(8):2110-2115.PMID:35969376DOI:10.1021/acs.jnatprod.2c00332.
The structural revision of four Stemona alkaloids from Stemona tuberosa is reported. The misassignment of the Tuberostemonine O structure (1) was recognized when a new alkaloid, Tuberostemonine P, was isolated and unambiguously assigned structure 1 in this work. Reinvestigation of the spectroscopic data and NMR calculations led to the revised structure 1a for Tuberostemonine O. The structural misassignment of dehydrocroomine A as 2 was corrected by reinterpreting the X-ray crystal structure, which was consistent with 2a. The structural reassignments of dehydrocroomine B (3 to 3a) and dehydrocroomine (4 to 4a) were confirmed by X-ray crystallography and NMR calculations, respectively.
TLC-image analysis of non-chromophoric Tuberostemonine alkaloid derivatives in Stemona species
Nat Prod Commun 2013 Aug;8(8):1065-8.PMID:24079167doi
A simple, selective, precise, and accurate thin-layer chromatographic (TLC) image analytical method was developed and validated for simultaneous quantification of the major components in the root extracts of Stemona tuberosa (Tuberostemonine, Tuberostemonine N and neotuberostemonine)), and S. phyllantha (Tuberostemonine and Tuberostemonine A). The analysis was performed by TLC on silica gel 60 F254 aluminum plates using a mixture of dichloromethane: ethyl acetate: methanol: ammonium hydroxide (50:45:4:1) as mobile phase. Post-derivatization was employed by dipping the TLC plate into Dragendorff's reagent to visualize the spots. Image analysis of the scanned TLC plate was performed to detect the contents of Tuberostemonine derivatives. The polynomial regression data for the calibration plots showed good linear relationships within the concentration range of 2-7 microg/spot. The method gave satisfactory precision, accuracy, selectivity and could simultaneously quantify Tuberostemonine, Tuberostemonine A, Tuberostemonine N and neotuberostemonine. Dried powdered roots of S. tuberosa grown in Thailand contained 1.31 +/- 0.28, 1.63 +/- 0.18 and 1.24 +/- 0.27% Tuberostemonine, Tuberostemonine N, and neotuberostemonine (dry weight), respectively, while S. phyllantha roots contained 1.39 +/- 0.14% Tuberostemonine and 0.39 +/- 0.08% Tuberostemonine A (dry weight). The proposed method was simple, inexpensive, and more accessible to apply for many local authorities and small laboratories.
Total synthesis of (-)-tuberostemonine
J Am Chem Soc 2002 Dec 18;124(50):14848-9.PMID:12475317DOI:10.1021/ja028603t.
The first total synthesis of the complex pentacyclic Stemona alkaloid Tuberostemonine was accomplished in 24 steps and in 1.4% overall yield from a hydroindole intermediate which is readily obtained in three steps from Cbz-l-tyrosine. An innovative synthetic strategy was applied that relays the single stereocenter of the amino acid precursor into nine of the ten stereogenic carbons of the target molecule. Among the highlights of the synthetic methodology are the 3-fold use of ruthenium catalysis, first in an azepine ring-closing metathesis and then in an alkene isomerization followed by a cross-metathesis propenyl-vinyl exchange, as well as the stereoselective attachment of the gamma-butyrolactone moiety to the core tetracycle by use of a lithiated ortho ester.
Tuberostemonine N, an active compound isolated from Stemona tuberosa, suppresses cigarette smoke-induced sub-acute lung inflammation in mice
Phytomedicine 2016 Jan 15;23(1):79-86.PMID:26902410DOI:10.1016/j.phymed.2015.11.015.
Objective: Our previous study demonstrated that a Stemona tuberosa extract had significant effects on cigarette smoking (CS)-induced lung inflammation in mice. The present study evaluated the potential of Tuberostemonine N (T.N) to prevent airway inflammation and suppress airway responses in a CS-induced in vivo COPD model. Methods: T.N was isolated from the root of ST and analyzed using 1D and 2D NMR. The purity of T.N was accessed using HPLC-ELSD analysis. C57BL/6 mice in this study were whole-body exposed to mainstream CS or room air for 4 weeks, and T.N (1, 5 and 10 mg/kg body wt.) was administered to mice via intraperitoneal (i.p.) injection before CS exposure. The number of inflammatory cells, including neutrophils, macrophages and lymphocytes, and the amount of proinflammatory cytokines and chemokines were accessed from bronchoalveolar lavage fluid (BALF) to investigate the anti-inflammatory effects of T.N. Average alveoli size was also measured using histological analyses. Results: Cellular profiles and histopathological analyses revealed that the infiltration of peribronchial and perivascular inflammatory cells decreased significantly in the T.N-treated groups compared to the CS-exposed control group. T.N significantly inhibited the secretion of proinflammatory cytokines and chemokines in BALF and decreased alveoli size in lung tissue. Conclusions: These data suggest that T.N exerts anti-inflammatory effects against airway inflammation, and T.N may be a novel therapeutic agent for lung diseases, such as COPD.