CAS#52659-56-0

MedKoo Cat#: 329887 | Name: Kirenol

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Description:

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

Kirenol is a compound from Herba Siegesbeckiae, induces apoptosis in human chronic myeloid leukemia K562 cells. Kirenol attenuates experimental autoimmune encephalomyelitis by inhibiting differentiation of Th1 and th17 cells and inducing apoptosis of effector T cells. Kirenol stimulates osteoblast differentiation through activation of the BMP and Wnt/β-catenin signaling pathways in MC3T3-E1 cells.

Chemical Structure

Kirenol

CAS#52659-56-0

Theoretical Analysis

MedKoo Cat#: 329887

Name: Kirenol

CAS#: 52659-56-0

Chemical Formula: C20H34O4

Exact Mass: 338.2457

Molecular Weight: 338.49

Elemental Analysis: C, 70.97; H, 10.13; O, 18.91

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 290.00	2 Weeks
25mg	USD 600.00	2 Weeks

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Synonym

Kirenol,

IUPAC/Chemical Name

(R)-1-((2S,4aR,4bS,6S,8R,8aS)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydrophenanthren-2-yl)ethane-1,2-diol

InChi Key

NRYNTARIOIRWAB-JPDRSCFKSA-N

InChi Code

InChI=1S/C20H34O4/c1-18(17(24)11-21)7-6-15-13(8-18)4-5-16-19(2,12-22)9-14(23)10-20(15,16)3/h8,14-17,21-24H,4-7,9-12H2,1-3H3/t14-,15-,16-,17+,18+,19+,20+/m1/s1

SMILES Code

OC[C@]1(C)C[C@@H](O)C[C@@]2(C)[C@]3([H])CC[C@@]([C@H](CO)O)(C)C=C3CC[C@]12[H]

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

>2 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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Kirenol is isolated from Siegesbeckia orientalis with anti-inflammatory and analgesic activity.

In vitro activity:

On Ox-LDL-stimulated HUVECs, KNL significantly inhibited the production of pro-inflammatory mediators such as NO, IL-1β, iNOS, TNF-α and IL-6. p38, ROS and Nrf2 expression were inhibited by KNL. Reference: Braz J Biol. 2022 May 4;84:e259421. https://pubmed.ncbi.nlm.nih.gov/35544792/

In vivo activity:

In vivo, the cartilage in kirenol-treated mice exhibited less cartilage degradation and lower OARSI scores. Taken together, the results of this study provide potent evidence that kirenol could be utilized as a potentially therapeutic agent in prevention and treatment of OA. Reference: J Orthop Surg Res. 2022 Apr 1;17(1):195. https://pubmed.ncbi.nlm.nih.gov/35365162/

	Solvent	mg/mL	mM
Solubility
	DMF	14.3	42.55
	DMSO	55.0	162.49
	Ethanol	5.0	14.77

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 338.49 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

Formulation protocol:

1. AbuZahra HM. Kirenol protects against oxidized low-density lipoprotein induced damages in endothelial cells. Braz J Biol. 2022 May 4;84:e259421. doi: 10.1590/1519-6984.259421. PMID: 35544792. 2. Rajendran P, Alzahrani AM, Ahmed EA, Veeraraghavan VP. Kirenol Inhibits B[a]P-Induced Oxidative Stress and Apoptosis in Endothelial Cells via Modulation of the Nrf2 Signaling Pathway. Oxid Med Cell Longev. 2021 Apr 23;2021:5585303. doi: 10.1155/2021/5585303. PMID: 33981385; PMCID: PMC8088375. 3. Li J, Zhang J, Yang M, Huang X, Zhang M, Fang X, Wu S. Kirenol alleviates diabetic nephropathy via regulating TGF-β/Smads and the NF-κB signal pathway. Pharm Biol. 2022 Dec;60(1):1690-1700. doi: 10.1080/13880209.2022.2112239. PMID: 36073930; PMCID: PMC9467559. 4. Hu W, Mao C, Sheng W. The protective effect of kirenol in osteoarthritis: an in vitro and in vivo study. J Orthop Surg Res. 2022 Apr 1;17(1):195. doi: 10.1186/s13018-022-03063-y. PMID: 35365162; PMCID: PMC8974005.

In vitro protocol:

In vivo protocol:

1. Li J, Zhang J, Yang M, Huang X, Zhang M, Fang X, Wu S. Kirenol alleviates diabetic nephropathy via regulating TGF-β/Smads and the NF-κB signal pathway. Pharm Biol. 2022 Dec;60(1):1690-1700. doi: 10.1080/13880209.2022.2112239. PMID: 36073930; PMCID: PMC9467559. 2. Hu W, Mao C, Sheng W. The protective effect of kirenol in osteoarthritis: an in vitro and in vivo study. J Orthop Surg Res. 2022 Apr 1;17(1):195. doi: 10.1186/s13018-022-03063-y. PMID: 35365162; PMCID: PMC8974005.

1: Wang J, Duan H, Wang Y, Pan B, Gao C, Gai C, Wu Q, Fu H. ent-Strobane and ent-Pimarane Diterpenoids from Siegesbeckia pubescens. J Nat Prod. 2017 Jan 27;80(1):19-29. doi: 10.1021/acs.jnatprod.6b00150. Epub 2016 Dec 23. PubMed PMID: 28009521. 2: Kim J, Kim MB, Yun JG, Hwang JK. Protective Effects of Standardized Siegesbeckia glabrescens Extract and Its Active Compound Kirenol against UVB-Induced Photoaging through Inhibition of MAPK/NF-κB Pathways. J Microbiol Biotechnol. 2017 Feb 28;27(2):242-250. doi: 10.4014/jmb.1610.10050. PubMed PMID: 27880964. 3: An J, Yang H, Zhang Q, Liu C, Zhao J, Zhang L, Chen B. Natural products for treatment of osteoporosis: The effects and mechanisms on promoting osteoblast-mediated bone formation. Life Sci. 2016 Feb 15;147:46-58. doi: 10.1016/j.lfs.2016.01.024. Epub 2016 Jan 18. Review. PubMed PMID: 26796578. 4: Xiao J, Yang R, Yang L, Fan X, Liu W, Deng W. Kirenol attenuates experimental autoimmune encephalomyelitis by inhibiting differentiation of Th1 and th17 cells and inducing apoptosis of effector T cells. Sci Rep. 2015 Mar 12;5:9022. doi: 10.1038/srep09022. PubMed PMID: 25762107; PubMed Central PMCID: PMC4356981. 5: Kong FY, Hu HH, Han ZB, Xu WY, Feng MX, Ma CH. [Study on index components and fingerprints of crude and processed Siegesbeckia Herbs]. Zhongguo Zhong Yao Za Zhi. 2014 Aug;39(15):2907-11. Chinese. PubMed PMID: 25423830. 6: Kim MB, Song Y, Hwang JK. Kirenol stimulates osteoblast differentiation through activation of the BMP and Wnt/β-catenin signaling pathways in MC3T3-E1 cells. Fitoterapia. 2014 Oct;98:59-65. doi: 10.1016/j.fitote.2014.07.013. Epub 2014 Jul 23. PubMed PMID: 25062891. 7: Lu Y, Qian R, Xiao J, Xu D, Fu H, Chen Y. Kirenol, a compound from Herba Siegesbeckiae, induces apoptosis in human chronic myeloid leukemia K562 cells. Pharmazie. 2014 Feb;69(2):148-53. PubMed PMID: 24640606. 8: Kim MB, Song Y, Kim C, Hwang JK. Kirenol inhibits adipogenesis through activation of the Wnt/β-catenin signaling pathway in 3T3-L1 adipocytes. Biochem Biophys Res Commun. 2014 Mar 7;445(2):433-8. doi: 10.1016/j.bbrc.2014.02.017. Epub 2014 Feb 12. PubMed PMID: 24530909. 9: Huo L, Jiang Z, Lei M, Wang X, Guo X. Simultaneous quantification of Kirenol and ent-16β,17-dihydroxy-kauran-19-oic acid from Herba Siegesbeckiae in rat plasma by liquid chromatography-tandem mass spectrometry and its application to pharmacokinetic studies. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Oct 15;937:18-24. doi: 10.1016/j.jchromb.2013.08.019. Epub 2013 Aug 19. PubMed PMID: 24008120. 10: Huo L, Jiang Z, Li H, Wang M, Ye X, Ji B, Guo X. Simultaneous determination of seven major diterpenoids in Siegesbeckia pubescens Makino by high-performance liquid chromatography coupled with evaporative light scattering detection. J Sep Sci. 2012 Oct;35(19):2585-91. doi: 10.1002/jssc.201200286. Epub 2012 Aug 9. PubMed PMID: 22887919. 11: Chen FF, Xie XY, Shi YP. Magnetic molecularly imprinted polymer for the detection of rhaponticin in Chinese patent medicines. J Chromatogr A. 2012 Aug 24;1252:8-14. doi: 10.1016/j.chroma.2012.06.071. Epub 2012 Jun 27. PubMed PMID: 22776726. 12: Wang JP, Zhou YM, Zhang YH. Kirenol production in hairy root culture of Siegesbeckea orientalis and its antimicrobial activity. Pharmacogn Mag. 2012 Apr;8(30):149-55. doi: 10.4103/0973-1296.96569. PubMed PMID: 22701289; PubMed Central PMCID: PMC3371437. 13: Lu Y, Xiao J, Wu ZW, Wang ZM, Hu J, Fu HZ, Chen YY, Qian RQ. Kirenol exerts a potent anti-arthritic effect in collagen-induced arthritis by modifying the T cells balance. Phytomedicine. 2012 Jul 15;19(10):882-9. doi: 10.1016/j.phymed.2012.04.010. Epub 2012 Jun 4. PubMed PMID: 22673798. 14: Lu Y, Xiao J, Wu Z, Wang Z, Fu H, Chen Y, Qian R. Effects of kirenol on bovine type II collagen-induced rat lymphocytes in vivo and in vitro. Nan Fang Yi Ke Da Xue Xue Bao. 2012 Jan;32(1):1-6. PubMed PMID: 22365994. 15: Chen FF, Wang R, Shi YP. Molecularly imprinted polymer for the specific solid-phase extraction of kirenol from Siegesbeckia pubescens herbal extract. Talanta. 2012 Jan 30;89:505-12. doi: 10.1016/j.talanta.2011.12.080. Epub 2012 Jan 4. PubMed PMID: 22284524. 16: Wang JP, Zhou YM, Ye YJ, Shang XM, Cai YL, Xiong CM, Wu YX, Xu HX. Topical anti-inflammatory and analgesic activity of kirenol isolated from Siegesbeckia orientalis. J Ethnopharmacol. 2011 Oct 11;137(3):1089-94. doi: 10.1016/j.jep.2011.07.016. Epub 2011 Jul 21. PubMed PMID: 21798328. 17: Wang ZM, Zhu SG, Wu ZW, Lu Y, Fu HZ, Qian RQ. Kirenol upregulates nuclear annexin-1 which interacts with NF-κB to attenuate synovial inflammation of collagen-induced arthritis in rats. J Ethnopharmacol. 2011 Sep 1;137(1):774-82. doi: 10.1016/j.jep.2011.06.037. Epub 2011 Jul 2. PubMed PMID: 21745559. 18: Jiang Z, Yu QH, Cheng Y, Guo XJ. Simultaneous quantification of eight major constituents in Herba Siegesbeckiae by liquid chromatography coupled with electrospray ionization time-of-flight tandem mass spectrometry. J Pharm Biomed Anal. 2011 Jun 1;55(3):452-7. doi: 10.1016/j.jpba.2011.02.023. Epub 2011 Feb 24. PubMed PMID: 21411260. 19: Song XL, Zhang QY, Wang ZM, Fu HZ, Qian RQ. A rapid and simple RP-HPLC method for quantification of kirenol in rat plasma after oral administration and its application to pharmacokinetic study. Biomed Chromatogr. 2011 May;25(5):542-6. doi: 10.1002/bmc.1481. Epub 2010 Aug 4. PubMed PMID: 20687099. 20: Liu Z, Chou G, Wang Z. [Determination of kirenol in Herba Siegesbeckiae Preparata by high performance liquid chromatography]. Zhongguo Zhong Yao Za Zhi. 2010 Mar;35(6):729-31. Chinese. PubMed PMID: 20545198.