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MedKoo Cat#: 462583 | Name: Tuberostemonine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tuberostemonine is an alkaloid that has been found in S. tuberosa and has diverse biological activities. 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 µg/cm2, respectively. Tuberostemonine (100 mg/kg) reduces the number of citric acid-induced coughs in guinea pigs. 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.

Chemical Structure

Tuberostemonine
Tuberostemonine
CAS#6879-01-2

Theoretical Analysis

MedKoo Cat#: 462583

Name: Tuberostemonine

CAS#: 6879-01-2

Chemical Formula: C22H33NO4

Exact Mass: 375.2410

Molecular Weight: 375.51

Elemental Analysis: C, 70.37; H, 8.86; N, 3.73; O, 17.04

Price and Availability

Size Price Availability Quantity
5mg USD 400.00 2 Weeks
10mg USD 600.00 2 Weeks
25mg USD 900.00 2 Weeks
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Related CAS #
No Data
Synonym
Tuberostemonine, NSC 366235; NSC366235; NSC-366235;
IUPAC/Chemical Name
(2S,31R,7aR,8R,8aS,11S,11aS,11bR)-8-ethyl-11-methyl-2-((2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl)dodecahydroazepino[3,2,1-hi]furo[3,2-e]indol-10(2H)-one
InChi Key
GYOGHROCTSEKDY-JJDZUBOLSA-N
InChi Code
InChI=1S/C22H33NO4/c1-4-13-14-7-5-6-8-23-16(17-9-11(2)21(24)26-17)10-15(19(14)23)18-12(3)22(25)27-20(13)18/h11-20H,4-10H2,1-3H3/t11-,12-,13+,14+,15+,16-,17-,18+,19+,20-/m0/s1
SMILES Code
CC[C@@H]1[C@H]2CCCCN3[C@@H](C[C@H]([C@H]4[C@H](C)C(=O)O[C@@H]14)[C@@H]23)[C@@H]5C[C@H](C)C(=O)O5
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Solvent mg/mL mM
Solubility
DMF 10.0 26.63
DMF:PBS (pH 7.2) (1:2) 0.3 0.88
DMSO 1.0 2.66
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 375.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Tang A, Liu Y, Ding Q, Huang G, Sha Z, Yang C, Cao F. Tuberostemonine may alleviates proliferation of lung fibroblasts caused by pulmonary fibrosis. Int J Immunopathol Pharmacol. 2024 Jan-Dec;38:3946320241274225. doi: 10.1177/03946320241274225. PMID: 39140804; PMCID: PMC11325469. 2: Xiong H, Sun S, Zhang W, Zhao D, Liu X, Tian Y, Feng S. Spatial metabolomics method to reveal the differences in chemical composition of raw and honey-fried Stemona tuberosa Lour. by using UPLC-Orbitrap Fusion MS and desorption electrospray ionization mass spectrometry imaging. Phytochem Anal. 2024 Jul 28. doi: 10.1002/pca.3428. Epub ahead of print. PMID: 39072901. 3: Zhang N, Xu Y, Yue X, Xiong L, Li H, Chen L. Isolation, characterization and anti-inflammatory effect of alkaloids from the roots of Stemona tuberosa Lour. Phytochemistry. 2024 Apr;220:114013. doi: 10.1016/j.phytochem.2024.114013. Epub 2024 Feb 7. PMID: 38331134. 4: Jiang W, Liu B, Chen G, Wei L, Zhou D, Wang Y, Gui Y, Wang C, Yang Y, Sun L, Li N. Characteristic alkaloids from Stemona sessilifolia with lung protective effects. Bioorg Chem. 2024 Feb;143:107033. doi: 10.1016/j.bioorg.2023.107033. Epub 2023 Dec 13. PMID: 38104498. 5: Liu Y, Tang A, Liu M, Xu C, Cao F, Yang C. Tuberostemonine may enhance the function of the SLC7A11/glutamate antiporter to restrain the ferroptosis to alleviate pulmonary fibrosis. J Ethnopharmacol. 2024 Jan 10;318(Pt B):116983. doi: 10.1016/j.jep.2023.116983. Epub 2023 Aug 1. PMID: 37532076. 6: Fu S, Song X, Hu Y, Zhu Q, Lv X, Tang X, Zhang M. Neotuberostemonine and tuberostemonine ameliorate pulmonary fibrosis through suppressing TGF-β and SDF-1 secreted by macrophages and fibroblasts via the PI3K-dependent AKT and ERK pathways. Chin J Nat Med. 2023 Jul;21(7):527-539. doi: 10.1016/S1875-5364(23)60444-3. PMID: 37517820. 7: Li Y, Sun M, Su S, Qi X, Liu S, Pan T, Zhou L, Li Y. Tuberostemonine alleviates high-fat diet-induced obesity and hepatic steatosis by increasing energy consumption. Chem Biol Interact. 2023 Aug 25;381:110545. doi: 10.1016/j.cbi.2023.110545. Epub 2023 May 24. PMID: 37236577. 8: Jiang JM, Shi ZH, Yang XW, Zhu D, Zhao BJ, Gao Y, Xia D, Yin ZQ, Pan K. Structural Revision of the Stemona Alkaloids Tuberostemonine O, Dehydrocroomines A and B, and Dehydrocroomine. J Nat Prod. 2022 Aug 26;85(8):2110-2115. doi: 10.1021/acs.jnatprod.2c00332. Epub 2022 Aug 15. PMID: 35969376. 9: Zheng X, Fan H, Song Z, Cheng P, Jiang H, Shi W, Xiao C, Wang J, Li Q, Yin G, Zhao X. Immobilized beta2-adrenergic receptor: A powerful chromatographic platform for drug discovery and evaluation of drug-like property for natural products. J Chromatogr A. 2021 Dec 6;1659:462635. doi: 10.1016/j.chroma.2021.462635. Epub 2021 Oct 21. PMID: 34731755. 10: Fu X, Zhao X, Zheng X, Wang T, Shayiranbieke A, Li L, Cao F, Ren J, Li Q, Zhao X. Rapidly identifying bioactive compounds from Zhisou oral liquid by immobilized receptor-based high-performance affinity chromatography. J Sep Sci. 2021 Sep;44(17):3219-3228. doi: 10.1002/jssc.202100174. Epub 2021 Jul 11. PMID: 34212514. 11: Liu Y, Shen Y, Teng L, Yang L, Cao K, Fu Q, Zhang J. The traditional uses, phytochemistry, and pharmacology of Stemona species: A review. J Ethnopharmacol. 2021 Jan 30;265:113112. doi: 10.1016/j.jep.2020.113112. Epub 2020 Jul 26. PMID: 32726680. 12: Pudjiastuti P, Puspaningsih NNT, Siswanto I, Fanani MZ, Ariga YK, Hase T, Sarker SD, Nahar L. Inhibitory Activity and Docking Analysis of Antimalarial Agents from Stemona sp. toward Ferredoxin-NADP+ Reductase from Malaria Parasites. J Parasitol Res. 2018 Aug 26;2018:3469132. doi: 10.1155/2018/3469132. PMID: 30225138; PMCID: PMC6129339. 13: Chen G, Brecker L, Felsinger S, Cai XH, Kongkiatpaiboon S, Schinnerl J. Morphological and chemical variation of Stemona tuberosa from southern China - Evidence for heterogeneity of this medicinal plant species. Plant Biol (Stuttg). 2017 Sep;19(5):835-842. doi: 10.1111/plb.12587. Epub 2017 Jun 28. PMID: 28580601. 14: Wang YJ, Zhao HD, Zhu CF, Li J, Xie HJ, Chen YX. Tuberostemonine reverses multidrug resistance in chronic myelogenous leukemia cells K562/ADR. J Cancer. 2017 Apr 9;8(6):1103-1112. doi: 10.7150/jca.17688. PMID: 28529625; PMCID: PMC5436265. 15: Tong Y, Xu W, Wu Y, Ou L, Zhang M, Xu X, Zhang C. Metabolic profiles of neotuberostemonine and tuberostemonine in rats by high performance liquid chromatography/quadrupole time-of-flight mass spectrometry. J Pharm Biomed Anal. 2017 Jul 15;141:210-221. doi: 10.1016/j.jpba.2017.04.018. Epub 2017 Apr 17. PMID: 28448890. 16: Wang Y, Qi Q, Li A, Yang M, Huang W, Xu H, Zhao Z, Li S. Immuno-enhancement effects of Yifei Tongluo Granules on cyclophosphamide-induced immunosuppression in Balb/c mice. J Ethnopharmacol. 2016 Dec 24;194:72-82. doi: 10.1016/j.jep.2016.08.046. Epub 2016 Aug 30. PMID: 27586820. 17: Liu G, Qiao S, Liu T, Yu H, Wang W, Zhou Y, Li Q, Li S. Simultaneous Determination of 18 Chemical Constituents in Traditional Chinese Medicine of Antitussive by UPLC-MS-MS. J Chromatogr Sci. 2016 Oct 17;54(9):1540-1552. doi: 10.1093/chromsci/bmw099. PMID: 27325684. 18: Jung KH, Kil YS, Jung J, Park S, Shin D, Lee K, Seo EK, Bae H. 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. doi: 10.1016/j.phymed.2015.11.015. Epub 2015 Dec 23. PMID: 26902410. 19: Jung KH, Beak H, Park S, Shin D, Jung J, Park S, Kim J, Bae H. The therapeutic effects of tuberostemonine against cigarette smoke-induced acute lung inflammation in mice. Eur J Pharmacol. 2016 Mar 5;774:80-6. doi: 10.1016/j.ejphar.2016.02.006. Epub 2016 Feb 2. PMID: 26849941. 20: Liao JN, Qin SD, Qu XS, Lin K, Huang DP, Li FX, Fan LL. [Comparative study of four alkaloids contents and antitussive activities of Stemona tuberosa from different habitats of Guangxi Province]. Zhong Yao Cai. 2014 Nov;37(11):1956-60. Chinese. PMID: 26027114.