Lobetyolin | CAS#129277-38-9 | biochemical

MedKoo Cat#: 145700 | Name: Lobetyolin

Description:

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

Lobetyolin is a compound that is primarily derived from Lobelia inflata, a plant known for its use in traditional medicine. It has been studied for its potential pharmacological effects, particularly in the area of respiratory health. Lobetyolin is believed to have bronchodilatory properties, meaning it may help relax and open the airways, which could be useful in treating conditions like asthma or chronic obstructive pulmonary disease (COPD).

Chemical Structure

Lobetyolin

CAS#129277-38-9

Theoretical Analysis

MedKoo Cat#: 145700

Name: Lobetyolin

CAS#: 129277-38-9

Chemical Formula: C20H28O8

Exact Mass: 396.1800

Molecular Weight: 396.44

Elemental Analysis: C, 60.59; H, 7.12; O, 32.29

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Lobetyolin;

IUPAC/Chemical Name

(2R,3R,4S,5S,6R)-2-(((4E,6R,7R,12E)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

InChi Key

MMMUDYVKKPDZHS-MXFZCOKBSA-N

InChi Code

1S/C20H28O8/c1-2-3-4-5-7-10-14(23)15(11-8-6-9-12-21)27-20-19(26)18(25)17(24)16(13-22)28-20/h2-3,8,11,14-26H,6,9,12-13H2,1H3/b3-2+,11-8+/t14-,15-,16-,17-,18+,19-,20-/m1/s1

SMILES Code

[H][C@@](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)(\C=C\CCCO)[C@H](O)C#CC#C\C=C\C

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 396.44 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.

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: Bailly C. Anticancer Properties of Lobetyolin, an Essential Component of Radix Codonopsis (Dangshen). Nat Prod Bioprospect. 2021 Apr;11(2):143-153. doi: 10.1007/s13659-020-00283-9. Epub 2020 Nov 7. PMID: 33161560; PMCID: PMC7981376. 2: Ni SH, Zhang XJ, OuYang XL, Ye TC, Li J, Li Y, Sun SN, Han XW, Long WJ, Wang LJ, Yang ZQ, Lu L. Lobetyolin Alleviates Ferroptosis of Skeletal Muscle in 5/6 Nephrectomized Mice via Activation of Hedgehog-GLI1 Signaling. Phytomedicine. 2023 Jul;115:154807. doi: 10.1016/j.phymed.2023.154807. Epub 2023 Apr 5. PMID: 37121057. 3: Cheng L, Zhai H, Du J, Zhang G, Shi G. Lobetyolin inhibits cell proliferation and induces cell apoptosis by downregulating ASCT2 in gastric cancer. Cytotechnology. 2023 Oct;75(5):435-448. doi: 10.1007/s10616-023-00588-w. Epub 2023 Aug 19. PMID: 37655270; PMCID: PMC10465467. 4: He W, Tao W, Zhang F, Jie Q, He Y, Zhu W, Tan J, Shen W, Li L, Yang Y, Cheng H, Sun D. Lobetyolin induces apoptosis of colon cancer cells by inhibiting glutamine metabolism. J Cell Mol Med. 2020 Mar;24(6):3359-3369. doi: 10.1111/jcmm.15009. Epub 2020 Jan 28. PMID: 31990147; PMCID: PMC7131919. 5: Chen Y, Tian Y, Jin G, Cui Z, Guo W, Zhang X, Liu X. Lobetyolin inhibits the proliferation of breast cancer cells via ASCT2 down-regulation-induced apoptosis. Hum Exp Toxicol. 2021 Dec;40(12):2074-2086. doi: 10.1177/09603271211021476. Epub 2021 Jun 2. PMID: 34075790. 6: Tadege G, Alebachew Y, Hymete A, Tadesse S. Identification of lobetyolin as a major antimalarial constituent of the roots of Lobelia giberroa Hemsl. Int J Parasitol Drugs Drug Resist. 2022 Apr;18:43-51. doi: 10.1016/j.ijpddr.2022.01.002. Epub 2022 Jan 22. PMID: 35092864; PMCID: PMC8802882. 7: Hou YY, Qi SM, Leng J, Shen Q, Tang S, Zhang JT, Hu JN, Jiang S, Li W. Lobetyolin, a Q-marker isolated from Radix Platycodi, exerts protective effects on cisplatin-induced cytotoxicity in HEK293 cells. J Nat Med. 2023 Sep;77(4):721-734. doi: 10.1007/s11418-023-01714-w. Epub 2023 Jun 23. PMID: 37353674. 8: Chen Z, Su Y, Ding J, He J, Lai L, Song Y. Lobetyolin protects mice against LPS-induced sepsis by downregulating the production of inflammatory cytokines in macrophage. Front Pharmacol. 2024 May 10;15:1405163. doi: 10.3389/fphar.2024.1405163. PMID: 38799158; PMCID: PMC11116692. 9: Liu L, Liu Z, Yang L, Wu X, Zhu J, Liu L, Liu Y. Lobetyolin suppressed lung cancer in a mouse model by inhibiting epithelial-mesenchymal transition. Eur J Histochem. 2022 Jul 4;66(3):3423. doi: 10.4081/ejh.2022.3423. PMID: 35785916; PMCID: PMC9294612. 10: Hu J, Wang D, Wang F, Lin P. Lobetyolin Suppresses the Proliferation of Hepatocellular Carcinoma through Activating DUSP1-ERK1/2 Signaling Pathway. Biol Pharm Bull. 2024;47(10):1751-1758. doi: 10.1248/bpb.b24-00307. PMID: 39477468. 11: Wang J, Liu X, Wei W, Yang J, Li Q, Chu S, Liu P, Zhang J, He W. Regulation of oxygen-glucose deprivation/reperfusion-induced inflammatory responses and M1-M2 phenotype switch of BV2 microglia by lobetyolin. Metab Brain Dis. 2023 Dec;38(8):2627-2644. doi: 10.1007/s11011-023-01292-6. Epub 2023 Oct 14. PMID: 37837601. 12: Yoon IS, Cho SS. Effects of lobetyolin on xanthine oxidase activity in vitro and in vivo: weak and mixed inhibition. Nat Prod Res. 2021 May;35(10):1667-1670. doi: 10.1080/14786419.2019.1622108. Epub 2019 May 29. PMID: 31140315. 13: Liang Y, Wei G, Ning K, Zhang G, Liu Y, Dong L, Chen S. Contents of lobetyolin, syringin, and atractylolide III in Codonopsis pilosula are related to dynamic changes of endophytes under drought stress. Chin Med. 2021 Nov 22;16(1):122. doi: 10.1186/s13020-021-00533-z. PMID: 34809641; PMCID: PMC8607676. 14: Zhao F, Fan L, Yang J, Yang M, Zhang C, Wang F, Wang Y. Heterologous expression of BACE1 and its interaction with Codonopsis pilosula polysaccharides and Lobetyolin. Int J Biol Macromol. 2024 Oct;277(Pt 2):133440. doi: 10.1016/j.ijbiomac.2024.133440. Epub 2024 Jun 28. PMID: 38944075. 15: Xie Q, Wang H, Guan H, Xu N, Zhao X, Cheng X, Wang C. The in vitro/in vivo metabolic pathways analysis of lobetyol, lobetyolin, and lobetyolinin, three polyacetylenes from Codonopsis Radix, by UHPLC-Q/TOF-MS and UHPLC-MS/MS. J Pharm Biomed Anal. 2023 Jan 20;223:115140. doi: 10.1016/j.jpba.2022.115140. Epub 2022 Nov 4. PMID: 36356406. 16: Dong J, Cheng M, Xue R, Deng C, Liu H, Zhang T, Lu T, Mao C, Xiao S, Li L, Pi W. Comparative pharmacokinetic and bioavailability study of lobetyolin in rats after administration of lobetyolin and Codonopsis pilosula extract by ultra-performance LC-tandem mass spectrometry. Biomed Chromatogr. 2021 Aug;35(8):e5125. doi: 10.1002/bmc.5125. Epub 2021 Apr 18. PMID: 33783828. 17: Sun B, Gou X, Bai R, Abdelmoaty AAA, Ma Y, Zheng X, Hu F. Direct electrochemistry and electrocatalysis of lobetyolin via magnetic functionalized reduced graphene oxide film fabricated electrochemical sensor. Mater Sci Eng C Mater Biol Appl. 2017 May 1;74:515-524. doi: 10.1016/j.msec.2016.11.139. Epub 2016 Dec 14. PMID: 28254326. 18: Yoon YP, Ryu J, Park SH, Lee HJ, Lee S, Lee SK, Kim JO, Hong JH, Seok JH, Lee CJ. Effects of Lobetyolin, Lobetyol and Methyl linoleate on Secretion, Production and Gene Expression of MUC5AC Mucin from Airway Epithelial Cells. Tuberc Respir Dis (Seoul). 2014 Nov;77(5):203-8. doi: 10.4046/trd.2014.77.5.203. Epub 2014 Nov 28. PMID: 25473407; PMCID: PMC4250919. 19: Ni SH, OuYang XL, Liu X, Lin JH, Li Y, Sun SN, Deng JP, Han XW, Zhang XJ, Li H, Huang YS, Chen ZX, Lian ZM, Wang ZK, Long WJ, Wang LJ, Yang ZQ, Lu L. A molecular phenotypic screen reveals that lobetyolin alleviates cardiac dysfunction in 5/6 nephrectomized mice by inhibiting osteopontin. Phytomedicine. 2022 Dec;107:154412. doi: 10.1016/j.phymed.2022.154412. Epub 2022 Aug 28. PMID: 36191549. 20: Xu L, Ma L, Wei R, Ma Y, Ma T, Dang J, Chen Z, Li S, Ma S, Chen G. Effect of Continuous Cropping on Growth and Lobetyolin Synthesis of the Medicinal Plant Codonopsis pilosula (Franch.) Nannf. Based on the Integrated Analysis of Plant- Metabolite-Soil Factors. J Agric Food Chem. 2024 Sep 11;72(36):19604-19617. doi: 10.1021/acs.jafc.4c03664. Epub 2024 Aug 28. PMID: 39196612.