Identification of new pyrrole alkaloids from the fruits of Lycium chinense
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  • 作者:Ui Joung Youn ; Joo Yun Lee ; Yun-Seo Kil ; Ah-Reum Han…
  • 关键词:Lycium chinense ; Solanaceae ; Pyrrole alkaloid ; ECD ; Absolute configuration
  • 刊名:Archives of Pharmacal Research
  • 出版年:2016
  • 出版时间:March 2016
  • 年:2016
  • 卷:39
  • 期:3
  • 页码:321-327
  • 全文大小:523 KB
  • 参考文献:Amos RIJ, Gourlay BS, Molesworth PP, Smith JA, Sprod OR (2005) Annulation of pyrrole: application to the synthesis of indolizidine alkaloids. Tetrahedron 61:8226–8230CrossRef
    Barone V, Cossi MJ (1998) Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model. J Phys Chem A 102:1995–2001CrossRef
    Bruhn T, Hemberger Y, Schaumlöffel A, Bringmann G (2010) SpecDis version 1.50. University of Wűerzburg, Wűerzburg
    Chan TH, Lee SD (1983) 1,4-Dichloro-1,4-dimethoxybutane as a mild reagent for the conversion of primary amines to pyrroles. Synthesis of a pyrrole compound from tobacco. J Org Chem 48:3059–3061CrossRef
    Charles WJ, Qian T, Alexander ZJ (1991) Short, enantiogenic syntheses of (−)-indolizidine 167B and (+)-monomorine. J Am Chem Soc 113:3513–3518CrossRef
    Cossi M, Rega N, Scalmani G, Barone V (2003) Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model. J Comput Chem 24:669–681CrossRef PubMed
    Dieter RK, Yu H (2000) A facile synthesis of polysubstituted pyrroles. Org Lett 2:2283–2286CrossRef PubMed
    Duke JA, Bogenschutz-Godwin MJ, duCellier J, Duke PAK (2002) Handbook of medicinal herbs. CRC Press, New YorkCrossRef
    Franc C, Denone F, Cuisiner C, Ghosez L (1999) A general synthesis of 2-formyl-3-arylpyrroles. Tetrahedron Lett 40:4555–4558CrossRef
    Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE Jr., Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09. Revision D.01. Gaussian, Inc, Wallingford
    Gaullier JM, Bazin M, Valla A, Giraud M, Santus RJ (1995) Amino acid-pyrrole N-conjugates; a new class of antioxidants II. Effectiveness of singlet oxygen quenching by luminescence measurements. J Photochem Photobiol B 30:195–200CrossRef
    Jefford CW, Sienkiewicz K, Thornton SR (1995) Short, enantiospecific syntheses of indolizidines 209B and 209D, and piclavine A from diethyl-L-glutamate. Helv Chim Acta 78:1511–1524CrossRef
    Josey AD, Jenner EL (1962) N-Functionally substituted pyrroles. J Org Chem 27:2466–2470CrossRef
    Kang YK (2001) Ab initio MO and density functional studies on trans and cis conformers of N-methylacetamide. J Mol Struct (Thoechem) 546:183–193CrossRef
    Kim SY, Choi YH, Huh H, Kim J, Kim YC, Lee HS (1997a) New antihepatotoxic cerebroside from Lycium chinense fruits. J Nat Prod 60:274–276CrossRef PubMed
    Kim SY, Kim HP, Huh H, Kim YC (1997b) Antihepatotoxic zeaxanthins from the fruits of Lycium chinense. Arch Pharmacal Res 20:529–532CrossRef
    Lin CC, Chuang SC, Lin JM, Yang JJ (1997) Evaluation of the antiinflammatory hepatoprotective and antioxidant activities of Lycium chinense from Taiwan. Phytomedicine 4:213–220CrossRef PubMed
    Liu JH, Yang QC, Mak TCW, Wong HNC (2000) Highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles: a formal total synthesis of lukianol A. J Org Chem 65:3587–3595CrossRef PubMed
    Liu WY, Zhang WD, Chen H, Gu ZB, Li TZ, Zhou YJ (2003) Pyrrole alkaloids from Bolbostemma paniculatum. J Asian Nat Prod Res 5:159–163CrossRef PubMed
    Park MJ, Kim SR, Huh H, Jung JH, Kim YC (1994) Betaine attenuates glutamate-induced neurotoxicity in primary cultured brain cells. Arch Pharmacal Res 17:343–347CrossRef
    Ragno R, Marshall GR, Di Santo R, Costi R, Massa S, Rompei R, Artico M (2000) Antimycobacterial pyrroles: synthesis, anti-Mycobacterium tuberculosis activity and QSAR studies. Bioorg Med Chem 8:1423–1432CrossRef PubMed
    Tressl R, Nittka C, Kersten E, Rewicki DJ (1995) Formation of isoleucine-specific Maillard products from [1-13C]-d -glucose and [1-13C]-D-fructose. J Agric Food Chem 43:1163–1169CrossRef
    Youn UJ, Kil YS, Nam JW, Lee YJ, Kim J, Lee D, Lee JH, Seo EK (2013) New pyrrole alkaloids with bulky N-alkyl side chains containing stereogenic centers from Lycium chinense. Helv Chim Acta 96:1482–1487CrossRef
  • 作者单位:Ui Joung Youn (1)
    Joo Yun Lee (2)
    Yun-Seo Kil (1)
    Ah-Reum Han (1)
    Chong Hak Chae (2)
    Shi Yong Ryu (2)
    Eun-Kyoung Seo (1)

    1. Graduate School of Pharmaceutical Sciences, College of Pharmacy, Ewha Womans University, Seoul, 120-750, Korea
    2. Drug Discovery Platform Technology Team, Korea Research Institute of Chemical Technology, Daejeon, 305-600, Korea
  • 刊物主题:Pharmacy; Pharmacology/Toxicology;
  • 出版者:Springer Netherlands
  • ISSN:1976-3786
文摘
Three new minor pyrrole alkaloids, 3-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]pentanedioic acid (1), (2R)-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]-1-methoxy-1-oxobutanoic acid (2), and methyl (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-4-methylpentanoate (3) were isolated from the fruits of Lycium chinense Miller (Solanaceae), along with the known compound, methyl (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-3-(phenyl)propanoate (4). The structures of 1–4 were elucidated by analysis of their 1D- and 2D-NMR and HRMS data. The absolute configurations of 2–4, possessing a stereogenic center in each structure, were determined by comparison of their experimental electronic circular dichroism (ECD) with those of calculated ECD values.

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