Tuberostemonine
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MedKoo CAT#: 462583

CAS#: 6879-01-2

Description: 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

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Tuberostemonine
CAS# 6879-01-2
Instruction

Theoretical Analysis

MedKoo Cat#: 462583
Name: Tuberostemonine
CAS#: 6879-01-2
Chemical Formula: C22H33NO4
Exact Mass: 375.24
Molecular Weight: 375.509
Elemental Analysis: C, 70.37; H, 8.86; N, 3.73; O, 17.04

Price and Availability

Size Price Availability Quantity
10mg USD 300 2 Weeks
25mg USD 600 2 Weeks
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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:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 10.0 26.63
DMF:PBS (pH 7.2) (1:2) 0.3 0.88
DMSO 1.0 2.66

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: 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 Jul 2. doi: 10.1002/jssc.202100174. Epub ahead of print. PMID: 34212514.

2: 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.

3: 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.

4: 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.

5: 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.

6: 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.

7: 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.

8: 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.

9: 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.

10: 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.

11: 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.

12: Jung Jang E, Kil YS, Ryeon Park H, Oh S, Kyeong Kim H, Gyeong Jeong M, Kyoung Seo E, Sook Hwang E. Suppression of IL-2 production and proliferation of CD4(+) T cells by tuberostemonine O. Chem Biodivers. 2014 Dec;11(12):1954-62. doi: 10.1002/cbdv.201400074. PMID: 25491339.

13: Lim D, Lee E, Jeong E, Jang YP, Kim J. Stemona tuberosa prevented inflammation by suppressing the recruitment and the activation of macrophages in vivo and in vitro. J Ethnopharmacol. 2015 Feb 3;160:41-51. doi: 10.1016/j.jep.2014.11.032. Epub 2014 Dec 2. PMID: 25476485.

14: Kongkiatpaiboon S, Keeratinijakal V, Gritsanapan W. TLC-image analysis of non-chromophoric tuberostemonine alkaloid derivatives in Stemona species. Nat Prod Commun. 2013 Aug;8(8):1065-8. PMID: 24079167.

15: Sun H, Dong W, Zhang A, Wang W, Wang X. Pharmacokinetics study of multiple components absorbed in rat plasma after oral administration of Stemonae radix using ultra-performance liquid-chromatography/mass spectrometry with automated MetaboLynx software analysis. J Sep Sci. 2012 Dec;35(24):3477-85. doi: 10.1002/jssc.201200791. PMID: 23225713.

16: Sun H, Dong W, Zhang A, Wang W, Wang X. Ultra-performance liquid- chromatography with tandem mass spectrometry performing pharmacokinetic and biodistribution studies of croomine, neotuberostemonine and tuberostemonine alkaloids absorbed in the rat plasma after oral administration of Stemonae Radix. Fitoterapia. 2012 Dec;83(8):1699-705. doi: 10.1016/j.fitote.2012.09.027. Epub 2012 Oct 4. PMID: 23041522.

17: Astelbauer F, Gruber M, Brem B, Greger H, Obwaller A, Wernsdorfer G, Congpuong K, Wernsdorfer WH, Walochnik J. Activity of selected phytochemicals against Plasmodium falciparum. Acta Trop. 2012 Aug;123(2):96-100. doi: 10.1016/j.actatropica.2012.04.002. Epub 2012 Apr 17. PMID: 22537982.

18: Kongkiatpaiboon S, Schinnerl J, Felsinger S, Keeratinijakal V, Vajrodaya S, Gritsanapan W, Brecker L, Greger H. Structural relationships of stemona alkaloids: assessment of species-specific accumulation trends for exploiting their biological activities. J Nat Prod. 2011 Sep 23;74(9):1931-8. doi: 10.1021/np2004374. Epub 2011 Sep 8. PMID: 21902195.

19: Xu YT, Shaw PC, Jiang RW, Hon PM, Chan YM, But PP. Antitussive and central respiratory depressant effects of Stemona tuberosa. J Ethnopharmacol. 2010 Apr 21;128(3):679-84. doi: 10.1016/j.jep.2010.02.018. Epub 2010 Feb 26. PMID: 20219659.

20: Zhou X, Leung PH, Li N, Ye Y, Zhang L, Zuo Z, Lin G. Oral absorption and antitussive activity of tuberostemonine alkaloids from the roots of Stemona tuberosa. Planta Med. 2009 May;75(6):575-80. doi: 10.1055/s-0029-1185363. Epub 2009 Feb 12. PMID: 19214944.