Cucurbitacin B | CAS#6199-67-3 | triterpene

MedKoo Cat#: 330102 | Name: Cucurbitacin B

Featured

Description:

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

Cucurbitacin B is a plant-derived triterpene that has the classic four-ring structure of mammalian steroids. Cucurbitacin B suppresses metastasis mediated by reactive oxygen species (ROS) via focal adhesion kinase (FAK) in breast cancer MDA-MB-231 cells. Cucurbitacin B induces inhibitory effects via CIP2A/PP2A/Akt pathway in glioblastoma multiforme. Cucurbitacin B acts a potential insect growth regulator by antagonizing 20-hydroxyecdysone activity.

Chemical Structure

Cucurbitacin B

CAS#6199-67-3

Theoretical Analysis

MedKoo Cat#: 330102

Name: Cucurbitacin B

CAS#: 6199-67-3

Chemical Formula: C32H46O8

Exact Mass: 558.3193

Molecular Weight: 558.71

Elemental Analysis: C, 68.79; H, 8.30; O, 22.91

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
250mg	USD 1,450.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Cucurbitacin B; Cuc B; NSC 49451; NSC49451; NSC-49451; NSC 144154; NSC144154; NSC-144154;

IUPAC/Chemical Name

(R,E)-6-((2S,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate

InChi Key

IXQKXEUSCPEQRD-DKRGWESNSA-N

InChi Code

InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22+,25+,29+,30-,31+,32+/m1/s1

SMILES Code

O[C@@H]1C(C(C)(C)C2=CC[C@]([C@@](C[C@@H](O)[C@]3([H])[C@](O)(C)C(/C=C/C(C)(C)OC(C)=O)=O)(C)[C@]3(C)CC4=O)([H])[C@]4(C)[C@]2([H])C1)=O

Appearance

Solid powder

Purity

>97% (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:

Cucurbitacin B belongs to a class of highly oxidized tetracyclic triterpenoids; could repress cancer cell progression.

In vitro activity:

CuB (cucurbitacin B) inhibited cell proliferation of PEL cell lines (BCBL-1, BC-1, GTO and TY-1) in a dose-dependent manner (0-50 nM) and induced apoptosis of BCBL-1 cells via caspase activation in a dose- and time-dependent manner. In addition, CuB caused cell-shape disruption by inducing actin aggregation and suppressing the p-cofilin level, resulting in BCBL-1 cell arrest at the G2/M phase. Reference: Phytomedicine. 2021 May;85:153545. https://pubmed.ncbi.nlm.nih.gov/33799222/

In vivo activity:

CuB (cucurbitacin B) effectively suppressed multiple stimuli-activated IL-1β secretion by interrupting NLRP3 inflammasome complex formation, inhibiting NLRP3 inflammasome activation and suppressing key enzymes of glycolysis in macrophages. Consistent with this, CuB pretreatment also ameliorated MSU-induced arthritis in vivo models of gout arthritis, manifested by reduced foot swelling and inflammatory cell infiltration. Reference: J Mol Endocrinol. 2021 Jun 21;67(2):27-40. https://pubmed.ncbi.nlm.nih.gov/34047713/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	178.98
	Ethanol	50.0	89.49

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 558.71 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. Yuan R, Zhao W, Wang QQ, He J, Han S, Gao H, Feng Y, Yang S. Cucurbitacin B inhibits non-small cell lung cancer in vivo and in vitro by triggering TLR4/NLRP3/GSDMD-dependent pyroptosis. Pharmacol Res. 2021 Aug;170:105748. doi: 10.1016/j.phrs.2021.105748. Epub 2021 Jul 1. PMID: 34217831. 2. Ueno M, Kariya R, Sittithumcharee G, Okada S. Cucurbitacin B induces apoptosis of primary effusion lymphoma via disruption of cytoskeletal organization. Phytomedicine. 2021 May;85:153545. doi: 10.1016/j.phymed.2021.153545. Epub 2021 Mar 10. PMID: 33799222. 3. Xue Y, Li R, Fang P, Ye ZQ, Zhao Y, Zhou Y, Zhang KQ, Li L. NLRP3 inflammasome inhibitor cucurbitacin B suppresses gout arthritis in mice. J Mol Endocrinol. 2021 Jun 21;67(2):27-40. doi: 10.1530/JME-20-0305. PMID: 34047713. 4. Tao B, Wang D, Yang S, Liu Y, Wu H, Li Z, Chang L, Yang Z, Liu W. Cucurbitacin B Inhibits Cell Proliferation by Regulating X-Inactive Specific Transcript Expression in Tongue Cancer. Front Oncol. 2021 Jul 6;11:651648. doi: 10.3389/fonc.2021.651648. PMID: 34295808; PMCID: PMC8290325.

In vitro protocol:

In vivo protocol:

1. Xue Y, Li R, Fang P, Ye ZQ, Zhao Y, Zhou Y, Zhang KQ, Li L. NLRP3 inflammasome inhibitor cucurbitacin B suppresses gout arthritis in mice. J Mol Endocrinol. 2021 Jun 21;67(2):27-40. doi: 10.1530/JME-20-0305. PMID: 34047713. 2. Tao B, Wang D, Yang S, Liu Y, Wu H, Li Z, Chang L, Yang Z, Liu W. Cucurbitacin B Inhibits Cell Proliferation by Regulating X-Inactive Specific Transcript Expression in Tongue Cancer. Front Oncol. 2021 Jul 6;11:651648. doi: 10.3389/fonc.2021.651648. PMID: 34295808; PMCID: PMC8290325.

1: Luo WW, Zhao WW, Lu JJ, Wang YT, Chen XP. Cucurbitacin B suppresses metastasis mediated by reactive oxygen species (ROS) via focal adhesion kinase (FAK) in breast cancer MDA-MB-231 cells. Chin J Nat Med. 2018 Jan;16(1):10-19. doi: 10.1016/S1875-5364(18)30025-6. PubMed PMID: 29425586. 2: Qin S, Li J, Si Y, He Z, Zhang T, Wang D, Liu X, Guo Y, Zhang L, Li S, Li Q, Liu Y. Cucurbitacin B induces inhibitory effects via CIP2A/PP2A/Akt pathway in glioblastoma multiforme. Mol Carcinog. 2018 Feb 2. doi: 10.1002/mc.22789. [Epub ahead of print] PubMed PMID: 29393542. 3: Zhou J, Zhao T, Ma L, Liang M, Guo YJ, Zhao LM. Cucurbitacin B and SCH772984 exhibit synergistic anti-pancreatic cancer activities by suppressing EGFR, PI3K/Akt/mTOR, STAT3 and ERK signaling. Oncotarget. 2017 Oct 9;8(61):103167-103181. doi: 10.18632/oncotarget.21704. eCollection 2017 Nov 28. PubMed PMID: 29262554; PubMed Central PMCID: PMC5732720. 4: Sallam AM, Esmat A, Abdel-Naim AB. Cucurbitacin-B attenuates CCl(4) -induced hepatic fibrosis in mice through inhibition of STAT-3. Chem Biol Drug Des. 2017 Dec 17. doi: 10.1111/cbdd.13160. [Epub ahead of print] PubMed PMID: 29250925. 5: Zou C, Liu G, Liu S, Liu S, Song Q, Wang J, Feng Q, Su Y, Li S. Cucurbitacin B acts a potential insect growth regulator by antagonizing 20-hydroxyecdysone activity. Pest Manag Sci. 2017 Dec 4. doi: 10.1002/ps.4817. [Epub ahead of print] PubMed PMID: 29205800. 6: Mallick MN, Khan W, Parveen R, Ahmad S, Sadaf, Najm MZ, Ahmad I, Husain SA. Exploring the Cytotoxic Potential of Triterpenoids-enriched Fraction of Bacopa monnieri by Implementing In vitro, In vivo, and In silico Approaches. Pharmacogn Mag. 2017 Oct;13(Suppl 3):S595-S606. doi: 10.4103/pm.pm_397_16. Epub 2017 Oct 11. PubMed PMID: 29142420; PubMed Central PMCID: PMC5669103. 7: Garg S, Kaul SC, Wadhwa R. Cucurbitacin B and cancer intervention: Chemistry, biology and mechanisms (Review). Int J Oncol. 2018 Jan;52(1):19-37. doi: 10.3892/ijo.2017.4203. Epub 2017 Nov 10. PubMed PMID: 29138804. 8: Wang Z, Zhu W, Gao M, Wu C, Yang C, Yang J, Wu G, Yang B, Kuang H. Simultaneous determination of cucurbitacin B and cucurbitacin E in rat plasma by UHPLC-MS/MS: A pharmacokinetics study after oral administration of cucurbitacin tablets. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Oct 15;1065-1066:63-69. doi: 10.1016/j.jchromb.2017.09.024. Epub 2017 Sep 18. PubMed PMID: 28946127. 9: Qu Y, Cong P, Lin C, Deng Y, Li-Ling J, Zhang M. Inhibition of paclitaxel resistance and apoptosis induction by cucurbitacin B in ovarian carcinoma cells. Oncol Lett. 2017 Jul;14(1):145-152. doi: 10.3892/ol.2017.6148. Epub 2017 May 10. PubMed PMID: 28693146; PubMed Central PMCID: PMC5494940. 10: Zhang ZR, Gao MX, Yang K. Cucurbitacin B inhibits cell proliferation and induces apoptosis in human osteosarcoma cells via modulation of the JAK2/STAT3 and MAPK pathways. Exp Ther Med. 2017 Jul;14(1):805-812. doi: 10.3892/etm.2017.4547. Epub 2017 Jun 6. PubMed PMID: 28673003; PubMed Central PMCID: PMC5488743. 11: Marostica LL, de Barros ALB, Oliveira J, Salgado BS, Cassali GD, Leite EA, Cardoso VN, Lang KL, Caro MSB, Durán FJ, Schenkel EP, de Oliveira MC, Simões CMO. Antitumor effectiveness of a combined therapy with a new cucurbitacin B derivative and paclitaxel on a human lung cancer xenograft model. Toxicol Appl Pharmacol. 2017 Aug 15;329:272-281. doi: 10.1016/j.taap.2017.06.007. Epub 2017 Jun 10. PubMed PMID: 28610991. 12: Wang X, Tanaka M, Peixoto HS, Wink M. Cucurbitacins: elucidation of their interactions with the cytoskeleton. PeerJ. 2017 May 30;5:e3357. doi: 10.7717/peerj.3357. eCollection 2017. PubMed PMID: 28584704; PubMed Central PMCID: PMC5452965. 13: Liu X, Duan C, Ji J, Zhang T, Yuan X, Zhang Y, Ma W, Yang J, Yang L, Jiang Z, Yu H, Liu Y. Cucurbitacin B induces autophagy and apoptosis by suppressing CIP2A/PP2A/mTORC1 signaling axis in human cisplatin resistant gastric cancer cells. Oncol Rep. 2017 Jul;38(1):271-278. doi: 10.3892/or.2017.5648. Epub 2017 May 18. PubMed PMID: 28534965. 14: Xiao Y, Yang Z, Wu QQ, Jiang XH, Yuan Y, Chang W, Bian ZY, Zhu JX, Tang QZ. Cucurbitacin B Protects Against Pressure Overload Induced Cardiac Hypertrophy. J Cell Biochem. 2017 Nov;118(11):3899-3910. doi: 10.1002/jcb.26041. Epub 2017 May 23. PubMed PMID: 28390176. 15: Bajcsik N, Pfab R, Pietsch J. Simultaneous determination of cucurbitacin B, E, I and E-glucoside in plant material and body fluids by HPLC-MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 May 1;1052:128-134. doi: 10.1016/j.jchromb.2017.03.030. Epub 2017 Mar 28. PubMed PMID: 28376351. 16: Hua S, Liu X, Lv S, Wang Z. Protective Effects of Cucurbitacin B on Acute Lung Injury Induced by Sepsis in Rats. Med Sci Monit. 2017 Mar 18;23:1355-1362. PubMed PMID: 28315572; PubMed Central PMCID: PMC5367850. 17: Ding X, Chi J, Yang X, Hao J, Liu C, Zhu C, Wang X, Liu X, Niu Y, Ji W, Chen D, Wu X. Cucurbitacin B synergistically enhances the apoptosis-inducing effect of arsenic trioxide by inhibiting STAT3 phosphorylation in lymphoma Ramos cells. Leuk Lymphoma. 2017 Oct;58(10):2439-2451. doi: 10.1080/10428194.2017.1289521. Epub 2017 Feb 20. PubMed PMID: 28278714. 18: Kim SH, Kang JG, Kim CS, Ihm SH, Choi MG, Yoo HJ, Lee SJ. Doxorubicin has a synergistic cytotoxicity with cucurbitacin B in anaplastic thyroid carcinoma cells. Tumour Biol. 2017 Feb;39(2):1010428317692252. doi: 10.1177/1010428317692252. PubMed PMID: 28218042. 19: Touihri-Barakati I, Kallech-Ziri O, Ayadi W, Kovacic H, Hanchi B, Hosni K, Luis J. Cucurbitacin B purified from Ecballium elaterium (L.) A. Rich from Tunisia inhibits α5β1 integrin-mediated adhesion, migration, proliferation of human glioblastoma cell line and angiogenesis. Eur J Pharmacol. 2017 Feb 15;797:153-161. doi: 10.1016/j.ejphar.2017.01.006. Epub 2017 Jan 17. PubMed PMID: 28108377. 20: Niu Y, Sun W, Lu JJ, Ma DL, Leung CH, Pei L, Chen X. PTEN Activation by DNA Damage Induces Protective Autophagy in Response to Cucurbitacin B in Hepatocellular Carcinoma Cells. Oxid Med Cell Longev. 2016;2016:4313204. doi: 10.1155/2016/4313204. Epub 2016 Nov 30. PubMed PMID: 28042385; PubMed Central PMCID: PMC5155108.