Structural characterization of isoprenylated flavonoids from Kushen by electrospray ionization multistage tandem mass spectrometry

Journal of Mass Spectrometry

Volumn 43, Issue 10, 2008, Pages 1421-1431

  Zhang, Yufeng ^a   Zhang, Peng ^a   Cheng, Yiyu ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

ESI MSn; Isoprenylated chalcones; Isoprenylated flavanols; Isoprenylated flavanones; Kushen

Indexed keywords

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ION SOURCES; IONIZATION; IONIZATION OF LIQUIDS; IONS; MASS SPECTROMETERS; MASS SPECTROMETRY; METHANOL; SPECTROMETERS; SPECTROMETRY; SPECTRUM ANALYSIS; TURBULENT FLOW;

ESI-MSN; ISOPRENYLATED CHALCONES; ISOPRENYLATED FLAVANOLS; ISOPRENYLATED FLAVANONES; KUSHEN;

ELECTROSPRAY IONIZATION;

CHALCONE DERIVATIVE; FLAVANOL DERIVATIVE; FLAVANONE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERIZATION; ISOPRENYLATION; KUSHEN; MEDICINAL PLANT; NEGATIVE ION ELECTROSPRAY; POSITIVE ION ELECTROSPRAY; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY;

CHALCONES; FLAVONES; FLAVONOIDS; INDICATORS AND REAGENTS; PRENYLATION; REFERENCE STANDARDS; SOPHORA; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

EID: 55249096255     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1423     Document Type: Article

References (34)

1. National Commission of Chinese Pharmacopoeia. Pharmacopoeia of the People's Republic of China, vol. 1. Chemical Industry Press: Beijing, 2000; 161.
2. Zhang JT, Wang W, Duan ZH. Progress of research and application of Matrine-type alkaloids. Progress in Modern Biomedicine 2007; 7: 451.
3. Zhao P, Zhang YJ, Yamamoto H, Yang CR. Recent advance on the chemistry, bioactivity and biosynthesis of prenylated flavonoids from Sophora flavecens. Natural Product Research and Development 2004; 16: 172.
4. Zhang YF, Kinginsun. Combined references for research and development of new drug in China, DXY.CN, http://db.dxy.cn/cgi-bin/qiye.pl?ym= %bf%e0%b2%ce&sq=0&mh=check [Accessed in March 16, 2008].
5. Sun M, Han J, Duan J, Cui Y, Wang T, Zhang W, Liu W, Hong J, Yao M, Xiong S, Yan X. Novel antitumor activities of Kushen flavonoids in vitro and in vivo. Phytotherapy Research 2007; 21: 269.
6. Han J, Sun M, Cui Y, Wang T, Zhang W, Guo M, Zhou Y, Liu W, Zhang M, Duan J, Xiong S, Yao M, Yan X. Kushen flavonoids induce apoptosis in tumor cells by inhibition of NF-kB activation and multiple receptor tyrosine kinase activities. Phytotherapy Research 2007; 21: 262.
7. Ding P, Chen D, Bastow KF, Nyarko AK, Wang X, Lee KH. Cytotoxic isoprenylated flavonoids from the roots of Sophora flavescens. Helvetica Chimica Acta 2004; 87: 2574.
8. Kang TH, Jeong SJ, Ko WG, Kim NY, Lee BH, Inagaki M, Miyamoto T, Higuchi R, Kim YC. Cytotoxic lavandulyl flavanones from Sophora flavescens. Journal of Natural Products 2000; 63: 680.
9. Yamamoto H, Senda M, Inoue K. Flavanone 8-dimethylallyl transferase in Sophora flavescens cell suspension cultures. Phytochemistry 2000; 54: 649.
10. Ko WG, Kang TH, Kim NY, Lee SJ, Kim YC, Ko GI, Ryu SY, Lee BH. Lavandulylflavonoids: a new class of in vitro apoptogenic agents from Sophora flavescens. Toxicology In Vitro 2000; 14: 429.
11. Liu PF, Cheng AQ, Deng TS, DU JM, Hou XL. The content and distribution of total flavonoids in Kushen. Chinese Traditional Patent Medicine 2007; 29: 596.
12. Zhang L, Min S, Wang S. Quantitative determination of isokurarinone in Kushen by HPLC. Chinese Journal of Pharmaceutical Analysis 2004; 24: 199.
13. Bai Y, Guo MQ, Song FR, Liu ZQ, Liu SY. Studies on flavonoids from Sophora flavescens Ait using ESI-MSn. Chemical Journal of Chinese Universities 2004; 25: 284.
14. Zhang L, Xu L, Xiao SS, Liao QF, Li Q, Liang J, Chen XH, Bi KS. Characterization of flavonoids in the extract of Sophora flavescens Ait. by high-performance liquid chromatography coupled with diode-array detector and electrospray ionization mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis 2007; 44: 1019.
15. Hatayama K, Komatsu M. Studies on the constituents of Sophora species. V. Constituents of the root of Sophora angustifolia Sieb et Zucc.(2). Chemical and Pharmaceutical Bulletin 1971; 19: 2126.
16. Yan XQ, Cui YM. Preparation and application of kurarinone and its derivatives and analogs in anti-cancer drug development, CN patent 200410030938.4., Oct 5, 2005.
17. Kyogoku K, Hatayama K, Komatsu M. Constituents of a Chinese crude drug Kushen (the root of Sophora flavescens). Isolation of five new flavonoids and formononetin. Chemical and Pharmaceutical Bulletin 1973; 21: 2733.
18. Kang SS, Kim JS, Son KH, Chang HW, Kim HP. A new prenylated flavanone from the roots of Sophora flavescens. Fitoterapia 2000; 71: 511.
19. Zhao Y-Y, Wang B, Lei L-M, Guo M-J, Zhang R-Y, Huang L-R, Yi Y-Y, Lou Z-C. Studies on the constituents of the flavonoids from the roots of Sophora flavescens Ait. Acta Botanica Sinica 1993; 35: 304.
20. Wu LJ, Miyase T, Ueno A, Kuroyanagi M, Noro T, Fukushima S. Studies on the constituents of Sophora flavescens Ait. III. Yakugaku Zasshi 1985; 105: 736.
21. Wu LJ, Miyase T, Ueno A, Kuroyanagi M, Noro T, Fukushima S, Sasaki S. Studies on the constituents of Sophora flavescens Ait. IV. Yakugaku Zasshi 1985; 105: 1034.
22. Komatsu M, Tomimori T, Hatayama K, Mikuriya N. Studies on the constituents of Sophora species. IV. Constituents of the root of Sophora angustifolia Sieb. et Zucc. Yakugaku Zasshi 1970; 90: 463.
23. Shimokoriyama M. Interconversion of chalcones and flavanones of a phloroglucinol-type structure. Journal of the American Chemical Society 1957; 79: 4199.
24. Stevens JF, Ivancic M, Hsu VL, Deinzer ML. Prenylflavonoids from Humulus lupulus. Phytochemistry 1997; 44: 1575.
25. Zhang Y, Shi Q, Shi P, Zhang W, Cheng Y. Characterization of isoquinoline alkaloids, diterpenoids and steroids in the Chinese herb Jin-Guo-Lan (Tinospora sagittata and Tinospora capillipes) by high-performance liquid chromatography/electrospray ionization with multistage mass spectrometry. Rapid Communications in Mass Spectrometry 2006; 20: 2328.
26. Takayama M, Fukai T, Ichikawa K, Nomura T. Identification of prenylated flavonoids using fast atom bombardment mass spectrometry. Rapid Communications in Mass Spectrometry 1991; 5: 67.
27. da Costa CT, Dalluge JJ, Welch MJ, Coxon B, Margolis SA, Horton D. Characterization of prenylated xanthones and flavanones by liquid chromatography/atmospheric pressure chemical ionization mass spectrometry. Journal of Mass Spectrometry 2000; 35: 540.
28. Takayama M, Fukai T, Hano Y, Nomura T. Mass spectrometry of prenylated flavonoids. Heterocycles (Sendai) 1992; 33: 405.
29. Hvattum E, Ekeberg D. Study of the collision-induced radical cleavage of flavonoid glycosides using negative electrospray ionization tandem quadrupole mass spectrometry. Journal of Mass Spectrometry 2003; 38: 43.
30. Fabre N, Rustan I, de Hoffmann E, Quetin-Leclercq J. Determination of flavone, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry. Journal of the American Society for Mass Spectrometry 2001; 12: 707.
31. Cheng C, Gross ML. Applications and mechanisms of charge-remote fragmentation. Mass Spectrometry Reviews 2000; 19: 398.
32. Zhang J, Brodbelt JS. Gas-phase hydrogen/deuterium exchange and conformations of deprotonated flavonoids and gas-phase acidities of flavonoids. Journal of the American Society for Mass Spectrometry 2004; 126: 5906.
33. Holmes JL, Aubry C, Mayer PM. Assigning Structures to Ions in Mass Spectrometry. Taylor &Francis Group: Boca Raton, London, New York, 2006.
34. Wang HY, Zhang X, Guo YL, Tang QH, Lu L. Using tandem mass spectrometry to predict chemical transformations of 2-pyrimidinyloxy-N-arylbenzyl amine derivatives in solution. Journal of the American Society for Mass Spectrometry 2006; 17: 253.