Jervine - CAS 469-59-0
Catalog number: 469-59-0
Category: Inhibitor
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Molecular Formula:
C27H39NO3
Molecular Weight:
425.6
COA:
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Targets:
Hedgehog
Description:
Jervine is a naturally occuring steroidal alkaloid that causes cyclopia by blocking sonic hedgehog(Shh) signaling. It is an inhibitor of Smo and derived from the Veratrum plant species. Jervine can be used to induce abnormal morphogenesis in a number of experimental models.
Purity:
>98%
Synonyms:
11-Ketocyclopamine
MSDS:
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InChIKey:
CLEXYFLHGFJONT-DNMILWOZSA-N
InChI:
InChI=1S/C27H39NO3/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-/m0/s1
Canonical SMILES:
CC1CC2C(C(C3(O2)CCC4C5CC=C6CC(CCC6(C5C(=O)C4=C3C)C)O)C)NC1
1.Global detection and semi-quantification of Fritillaria alkaloids in Fritillariae Ussuriensis Bulbus by a non-targeted multiple reaction monitoring approach.
Wang L1, Yao ZP2,3, Li P1, Chen SB2,3, So PK2,3, Shi ZQ4, Hu B2,3, Liu LF1, Xin GZ1. J Sep Sci. 2016 Jan;39(2):287-95. doi: 10.1002/jssc.201500880. Epub 2015 Dec 7.
Methods based on triple quadrupole tandem mass spectrometry have been widely used and reported as highly selective and sensitive methods for quantifying substances of herbal medicines. However, most of them were limited to targeted components, due to the difficulties to optimize the multiple reaction monitoring transitions without authentic standards. This study proposed a novel strategy for non-targeted optimization of multiple reaction monitoring method based on the diagnostic ion guided family classifications, tandem mass spectrometry database establishment, and transitions and collision energy screening. Applying this strategy, 59 Fritillaria alkaloids in Fritillariae Ussuriensis Bulbus have been classified, and 51 of these Fritillaria alkaloids were successfully detected by the optimal multiple reaction monitoring method. For semi-quantification, the easy-to-obtain Fritillaria alkaloids of each type, such as verticinone for cevanine type and peimisine for jervine type, were used as the reference standards to calibrate the other Fritillaria alkaloids in the same type.
2.ABCG2 is required to control the sonic hedgehog pathway in side population cells with stem-like properties.
Balbuena J1, Pachon G, Lopez-Torrents G, Aran JM, Castresana JS, Petriz J. Cytometry A. 2011 Sep;79(9):672-83. doi: 10.1002/cyto.a.21103. Epub 2011 Jul 19.
The Sonic Hedgehog (Hh) pathway has been implicated in the maintenance of stem or progenitor cells in many adult tissues. Importantly, abnormal Hh pathway activation is also associated with initiation of neoplasia, but its role in tumor growth is still unclear. Here, we demonstrate that cyclopamine, a plant-derived alkaloid product used to inhibit the Hh signaling pathway, reduces the Side Population (SP) obtained by Hoechst 33342 (Ho342) dye measurements. In addition, cyclopamine is able to modulate, along with oxysterols and other products, the ABCG2 transporter by increasing Ho342 and mitoxantrone uptake. Therefore, if the SP is solely measured as a Ho342 dye extruding fraction, this may be significantly modulated by the inhibition of ABCG2 transport fraction, independently from the action of cyclopamine on the Hh pathway. Our results indicate that ABCG2 may act in the upstream regulation of the Hh signaling pathway to protect the stemness of the SP compartment, giving support to the cancer stem cell hypothesis and suggesting that ABCG2 is not only critical for increased resistance to anticancer agents.
3.Potent anti-inflammatory and analgesic steroidal alkaloids from Veratrum taliense.
Li Q1, Yang KX2, Zhao YL3, Qin XJ3, Yang XW3, Liu L1, Liu YP4, Luo XD5. J Ethnopharmacol. 2016 Feb 17;179:274-9. doi: 10.1016/j.jep.2015.12.059. Epub 2015 Dec 29.
ETHNOPHARMACOLOGICAL RELEVANCE: "Pimacao" (the roots and rhizomes of Veratrum taliense Loes.) has been used as traditional folk medicine in Yunnan province (PR China) for the treatment of pain, swelling, and inflammation. It is the main component of the renowned traditional Chinese medicine, "Yunnan Baiyao". Previous investigations and clinical research have shown significant analgesic activity of Pimacao.
4.Insecticidal metabolites from the rhizomes of Veratrum album against adults of Colorado potato beetle, Leptinotarsa decemlineata.
Aydin T1, Cakir A, Kazaz C, Bayrak N, Bayir Y, Taşkesenligil Y. Chem Biodivers. 2014 Aug;11(8):1192-204. doi: 10.1002/cbdv.201300407.
The dried rhizomes of Veratrum album were individually extracted with CHCl3 , acetone, and NH4 OH/benzene to test the toxic effects against the Colorado potato beetle, Leptinotarsa decemlineata, which is an important agricultural pest. Fifteen compounds in various amounts were isolated from the extracts using column and thin-layer chromatography. The chemical structures of 14 compounds were characterized as octacosan-1-ol (1), β-sitosterol (2), stearic acid (3), diosgenin (4), resveratrol (5), wittifuran X (6), oxyresveratrol (7), β-sitosterol 3-O-β-D-glucopyranoside (8), diosgenin 3-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyronoside (9), oxyresveratrol 3-O-β-D-glucopyranoside (10), jervine (11), pseudojervine (13), 5,6-dihydro-1-hydroxyjervine (14), and saccharose (15) using UV, IR, MS, (1) H- and (13)C-NMR, and 2D-NMR spectroscopic methods. However, the chemical structure of 12, an oligosaccharide, has not fully been elucidated. Compounds 4, 6, 9, and 10 were isolated from V.
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