Pronuciferine | CAS#2128-60-1 | alkaloid

MedKoo Cat#: 584799 | Name: Pronuciferine

Description:

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

Pronuciferine ameliorate the glucose and lipid metabolism in insulin-resistant 3T3-L1 adipocytes.

Chemical Structure

Pronuciferine

CAS#2128-60-1

Theoretical Analysis

MedKoo Cat#: 584799

Name: Pronuciferine

CAS#: 2128-60-1

Chemical Formula: C19H21NO3

Exact Mass: 311.1521

Molecular Weight: 311.38

Elemental Analysis: C, 73.29; H, 6.80; N, 4.50; O, 15.41

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.

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Related CAS #

No Data

Synonym

Pronuciferine; (+)-Pronuciferine

IUPAC/Chemical Name

Spiro(2,5-cyclohexadiene-1,7'-1'H-cyclopent(ij)isoquinolin)-4-one, 2',3',8',8'a-tetrahydro-5',6'-dimethoxy-1'-methyl-, (R)-

InChi Key

WUYQEGNOQLRQAQ-CQSZACIVSA-N

InChi Code

InChI=1S/C19H21NO3/c1-20-9-6-12-10-15(22-2)18(23-3)17-16(12)14(20)11-19(17)7-4-13(21)5-8-19/h4-5,7-8,10,14H,6,9,11H2,1-3H3/t14-/m1/s1

SMILES Code

O=C1C=CC2(C3=C4[C@](C2)([H])N(C)CCC4=CC(OC)=C3OC)C=C1

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 311.38 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: Ma C, Li G, He Y, Xu B, Mi X, Wang H, Wang Z. Pronuciferine and nuciferine inhibit lipogenesis in 3T3-L1 adipocytes by activating the AMPK signaling pathway. Life Sci. 2015 Sep 1;136:120-5. doi: 10.1016/j.lfs.2015.07.001. Epub 2015 Jul 9. PubMed PMID: 26164185. 2: Bayazeid O, Eylem CC, Reçber T, Yalçın FN, Kır S, Nemutlu E. An LC-ESI-MS/MS method for the simultaneous determination of pronuciferine and roemerine in some Papaver species. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Oct 1;1096:223-227. doi: 10.1016/j.jchromb.2018.08.020. Epub 2018 Aug 21. PubMed PMID: 30189375. 3: Tomita M, Kato A, Ibuka T, Furukawa H. Mass spectra of pronuciferine and stepharine. Tetrahedron Lett. 1965 Aug;(32):2825-9. PubMed PMID: 5828474. 4: Xiao H, Chen AH, Ji AM, Li ZL, Song XD. [Isolation and identification of pronuciferine monomer]. Zhong Yao Cai. 2007 Mar;30(3):289-91. Chinese. PubMed PMID: 17634034. 5: Honda T, Shigehisa H. Novel and efficient synthetic path to proaporphine alkaloids: total synthesis of (+/-)-stepharine and (+/-)-pronuciferine. Org Lett. 2006 Feb 16;8(4):657-9. PubMed PMID: 16468735. 6: Fajardo V, Araya M, Cuadra P, Oyarzun A, Gallardo A, Cueto M, Diaz-Marrero AR, Darias J, Villarroel L, Alvarez C, Mora-Pérez Y, Joseph-Nathan P. Pronuciferine N-oxide, a proaporphine N-oxide alkaloid from Berberis coletioides. J Nat Prod. 2009 Jul;72(7):1355-6. doi: 10.1021/np9000976. PubMed PMID: 19469512. 7: Xiao H, Chen A, Ji A, Li Z. [The effects of pronuciferine on NO and NOS production in cultured human umbilical vein endothelium cells]. Zhong Yao Cai. 2005 Jun;28(6):503-5. Chinese. PubMed PMID: 16209270. 8: Gaskin RS, Feng PC. Some pharmacological activities of crotonosine and pronuciferine. J Pharm Pharmacol. 1967 Mar;19(3):195-6. PubMed PMID: 4382344. 9: Wu N, Xie H, Fang Y, Liu Y, Xi X, Chu Q, Dong G, Lan T, Wei Y. Isolation and purification of alkaloids from lotus leaves by ionic-liquid-modified high-speed countercurrent chromatography. J Sep Sci. 2018 Jan;41(2):571-577. doi: 10.1002/jssc.201700851. Epub 2017 Dec 5. PubMed PMID: 29087605. 10: Wang YX, Liu B, Shi RB. [HPLC determination of 2-hydroxy-1-methoxyaporphine, pronuciferine, nuciferine and roemerine in Nelumbo nucifera and its alkaloid fraction]. Zhongguo Zhong Yao Za Zhi. 2008 Jul;33(14):1713-6. Chinese. PubMed PMID: 18841775. 11: Ma C, Wang J, Chu H, Zhang X, Wang Z, Wang H, Li G. Purification and characterization of aporphine alkaloids from leaves of Nelumbo nucifera Gaertn and their effects on glucose consumption in 3T3-L1 adipocytes. Int J Mol Sci. 2014 Feb 26;15(3):3481-94. doi: 10.3390/ijms15033481. PubMed PMID: 24577311; PubMed Central PMCID: PMC3975348. 12: Bernauer K. [Total synthesis of D,L-pronuciferine]. Experientia. 1964 Jul 15;20(7):380-1. German. PubMed PMID: 5855678. 13: Kametani T, Yagi H. Total syntheses of (plus or minus)-glaziovine and (plus or minus)-pronuciferine by phenolic oxidative coupling. J Chem Soc Perkin 1. 1967;21:2182-4. PubMed PMID: 6069796. 14: Dong JW, Cai L, Fang YS, Xiao H, Li ZJ, Ding ZT. Proaporphine and aporphine alkaloids with acetylcholinesterase inhibitory activity from Stephania epigaea. Fitoterapia. 2015 Jul;104:102-7. doi: 10.1016/j.fitote.2015.05.019. Epub 2015 May 29. PubMed PMID: 26028544. 15: Do TC, Nguyen TD, Tran H, Stuppner H, Ganzera M. Analysis of alkaloids in Lotus (Nelumbo nucifera Gaertn.) leaves by non-aqueous capillary electrophoresis using ultraviolet and mass spectrometric detection. J Chromatogr A. 2013 Aug 9;1302:174-80. doi: 10.1016/j.chroma.2013.06.002. Epub 2013 Jun 12. PubMed PMID: 23838305. 16: Semwal DK, Semwal RB. Efficacy and safety of Stephania glabra: an alkaloid-rich traditional medicinal plant. Nat Prod Res. 2015;29(5):396-410. doi: 10.1080/14786419.2014.955487. Epub 2014 Sep 4. Review. PubMed PMID: 25186139. 17: Phillipson JD, Thomas OO, Gray AI, Sariyar G. Alkaloids from Papaver armeniacum, P. fugax and P. tauricola. Planta Med. 1981 Feb;41(2):105-18. PubMed PMID: 17401828. 18: Morikawa T, Kitagawa N, Tanabe G, Ninomiya K, Okugawa S, Motai C, Kamei I, Yoshikawa M, Lee IJ, Muraoka O. Quantitative Determination of Alkaloids in Lotus Flower (Flower Buds of Nelumbo nucifera) and Their Melanogenesis Inhibitory Activity. Molecules. 2016 Jul 19;21(7). pii: E930. doi: 10.3390/molecules21070930. PubMed PMID: 27447599; PubMed Central PMCID: PMC6272935. 19: Wang J, Hu X, Yin W, Cai H. [Alkaloids of plumula Nelumbinis]. Zhongguo Zhong Yao Za Zhi. 1991 Nov;16(11):673-5, 703. Chinese. PubMed PMID: 1804171. 20: Cheng P, Ma YB, Yao SY, Zhang Q, Wang EJ, Yan MH, Zhang XM, Zhang FX, Chen JJ. Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida. Bioorg Med Chem Lett. 2007 Oct 1;17(19):5316-20. Epub 2007 Aug 16. PubMed PMID: 17723297.