Distinct photoacidity of honokiol from magnolol

Journal of Fluorescence

Volumn 21, Issue 1, 2011, Pages 265-273

  Li, Hongmei ^a   Wang, Xianfeng ^a   Hu, Yuzhu ^a,b  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b Box 41 ^*  (China)

Author keywords

Geometry configuration; Honokiol; Magnolol; Photoacidity; Substitution effect

Indexed keywords

ELECTRON EFFECT; FLUORESCENCE CHARACTERISTICS; HONOKIOL; MAGNOLOL; PH DEPENDENCE; PHOTOACIDITY; SUBSTITUTION EFFECT; TIME-RESOLVED SPECTROSCOPY;

LASER SPECTROSCOPY;

GEOMETRY;

ACID; BIPHENYL DERIVATIVE; HONOKIOL; LIGNAN; MAGNOLOL;

ARTICLE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; PHOTOCHEMISTRY; SPECTROFLUOROMETRY;

ACIDS; BIPHENYL COMPOUNDS; HYDROGEN-ION CONCENTRATION; LIGNANS; MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; SPECTROMETRY, FLUORESCENCE;

EID: 79951515137     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-010-0714-1     Document Type: Article

References (30)

1. H Haraguchi H Ishikawa N Shirataki, et al. 1997 Antiperoxidative activity of neolignans from Magnolia obovata J Pharm Pharmacol 49 2 209 212 1:CAS:528:DyaK2sXitFemtb0%3D 9055197 (Pubitemid 27096118)
2. S Dikalov T Losik JL Arbiser 2008 Honokiol is a potent scavenger of superoxide and peroxyl radicals Biochem Pharmacol 76 589 596 1:CAS:528:DC%2BD1cXhtVSitbfO 18640101
3. J Park J Lee E Jung, et al. 2004 In vitro antibacterial and anti-inflammatory effects of honokiol and magnolol against Propionibacterium sp Eur J Pharmacol 496 123 189 195 1:CAS:528:DC%2BD2cXmt1OnsLY%3D 15288590 (Pubitemid 39024332)
4. JP Wang TF Ho LC Chang, et al. 1995 Anti-inflammatory effect of magnolol, isolated from Magnolia officinalis, on A23187-induced pleurisy in mice J Pharm Pharmacol 47 857 860 1:CAS:528:DyaK2MXpvFWgtLw%3D 8583356
5. CH Ko HH Chen YR Lin, et al. 2003 Inhibition of smooth muscle contraction by magnolol and honokiol in porcine trachea Planta Med 69 6 532 536 1:CAS:528:DC%2BD3sXlsFGis7k%3D 12865972
6. X Bai F Cerimele M Ushio-Fukai, et al. 2003 Honokiol, a small molecular weight product, inhibits angiogenesis in Vitro and tumor growth in Vivo J Bio Chem 278 37 35501 35507 1:CAS:528:DC%2BD3sXntVajsrY%3D (Pubitemid 37102321)
7. F Chen T Wang Y-F Wu, et al. 2004 Honokiol: a potent chemotherapy candidate for human colorectal carcinoma World J Gastroenterol 10 23 3459 3463 1:CAS:528:DC%2BD2cXhtFCht7nM 15526365 (Pubitemid 39549546)
8. L Li W Han Y Gu, et al. 2007 Honokiol induces a necrotic cell death through the mitochondrial permeability transition pore Cancer Res 67 10 4894 4903 1:CAS:528:DC%2BD2sXltl2gsb8%3D 17510419 (Pubitemid 46910198)
9. Y Fukuyama K Nakade Y Minoshima, et al. 2002 Neurotrophic activity of honokiol on the cultures of fetal rat cortical neurons Bioorg Med Chem Lett 12 1163 1166 1:CAS:528:DC%2BD38XisFWgtr4%3D 11934579 (Pubitemid 34270554)
10. MJ Fullmer RC Haltiwanger N Troupe, et al. 1994 Honokiol Acta Cryst C50 1966 1967 1:CAS:528:DyaK2MXivVyntL4%3D
11. 2 J Chinese Chem Soc 30 215 221
12. RB Mikkelsen C Asher T Hicks 1985 Extracellular pH, transmembrane distribution and cytotoxicity of chlorambucil Biochem Pharmacol 34 2531 2534 1:CAS:528:DyaL2MXkvVWgu7Y%3D 4015693 (Pubitemid 15063090)
13. BP Mahoney N Raghunand B Baggett, et al. 2003 Tumor acidity, ion trapping and chemotherapeutics: I. Acid pH affects the distribution of chemotherapeutic agents in vitro Biochem Pharmacol 66 1207 1218 1:CAS:528:DC%2BD3sXnsVams7k%3D 14505800 (Pubitemid 37130296)
14. 2a, mTHPP and mTHPC Photochem Photobiol 74 246 252 11547562
15. JP Chen S Wu 2004 Acid/base-treated activated carbons: characterization of functional groups and metal adsorptive properties Langmuir 20 2233 2242 1:CAS:528:DC%2BD2cXht1aitr0%3D 15835676
16. HS Gutowsky A Saika 1953 Dissociation, chemical exchange, and the proton magnetic resonance in some aqueous electrolytes J Chem Phys 21 1688 1694 1:CAS:528:DyaG2cXmtFaq
17. E Grunwald A Loewenstein 1957 Application of nuclear magnetic resonance to the study of acid-base equilibria J Chem Phys 27 641 642 1:CAS:528: DyaG1cXks1yj
18. 1H NMR titration Talanta 62 819 825 18969368
19. N Agmon 2005 Elementary steps in excited-state proton transfer J Phys Chem A 109 13 35 1:CAS:528:DC%2BD2cXhtVyltrnE 16839085 (Pubitemid 40121017)
20. LG Arnaut SJ Formosinho 1993 Excited-state proton transfer reactions I. Fundamentals and intermolecular reactions J Photochem Photobiol A: Chem 75 1 20 1:CAS:528:DyaK2cXhs1aqtrs%3D
21. HM Li YQ Wang ZY Yan, et al. 2007 Proton transfer of magnolol in ground and excited states J Photochem Photobiol A: Chemistry 186 202 211 1:CAS:528:DC%2BD2sXht1Git7Y%3D
22. EL Wehry LB Rogers 1965 Application of linear free energy relations to electronically excited states of monosubstituted phenols J Am Chem Soc 87 4234 4238 1:CAS:528:DyaF2MXkvVSjtb4%3D
23. SG Schulman WR Vincent WJM Underberg 1981 Acidity of cyanophenols in the S1 and T1 states: the influence of substituent orientation J Phys Chem 85 4068 4071 1:CAS:528:DyaL38XlslOj
24. G Granucci JT Hynes P Millié, et al. 2000 A theoretical investigation of excited-State acidity of phenol and cyanophenols J Am Chem Soc 122 12243 12253 1:CAS:528:DC%2BD3cXot1SgsLw%3D (Pubitemid 32062262)
25. HE Zimmerman 1998 Meta, ortho effect in organic photochemistry: mechanistic and exploratory organic photochemistry J Phys Chem A 102 5616 5621 1:CAS:528:DyaK1cXksVaitbo%3D (Pubitemid 128611454)
26. N Agmon W Retting C Groth 2002 Electronic determinants of photoacidity in cyanonaphthols J Am Chem Soc 124 1089 1096 1:CAS:528:DC%2BD38XlsVClsA%3D%3D 11829618 (Pubitemid 34130994)
27. Kieffer F, Rumpf P (1954) C R Acad Sci, Paris 238:360, 700
28. JW Bridges PJ Creaven RT Williams 1965 The fluorescence of some biphenyl derivatives Biochem J 96 872 878 1:CAS:528:DyaF2MXksVSisb4%3D 5862424
29. S Kothainayaki M Swaminathan 1997 A study of solvatochromism and proton transfer kinetics of 2, 2′-dihydroxybiphenyl J Photochem Photobiol A 102 217 221 1:CAS:528:DyaK2sXivFyqsr0%3D (Pubitemid 127163355)
30. EM Crompton FD Lewis 2004 Positional effects of the hydroxy substituent on the photochemical and photophysical behavior of 3- and 4-hydroxystilbene Photochem Photobiol Sci 3 660 668 1:CAS:528:DC%2BD2cXltlynu7c%3D 15239001 (Pubitemid 39139936)