Abstract
An analysis is given of literature information on the liquid column chromatography of coumarins for 1983–1990. Questions of the classification of the methods used, the choice of the optimum detection regime, and the conditions of chromatographic separation are discussed. The relationship between the structures of coumarins and their chromatographic behavior is considered. Conditions for the separation, isolation, and analysis of coumarins in various materials are given.
Similar content being viewed by others
Literature cited
R. D. H. Murray, J. Mendez, and S. A. Brown, The Natural Coumarins, Occurrence, Chemistry, and Biochemistry, Wiley, New York (1982).
I. Asenov and R. Gevrenova, Farmatsiya (Bulg.), No. 2, 40–56 (1990).
S. C. Basa, Phytochemistry,27, No. 7, 1933–1941 (1988).
R. A. Hill, Fortschr. Chem. Org. Naturst.,49, 1–78 (1986).
L. Janodar, Farmaceuticky Obzor.,54, No. 3, 129–141 (1985).
A. Henschen et al., High Performance Liquid Chromatography in Biochemistry, VCH, Weinheim (1985).
P. Bhandori and R. P. Rastogi, J. Sci. Ind. Res.,42, No. 7, 383–400 (1983).
O. A. Grigor'ev, A. A. Khabarov, and G. A. Drozd, “Methods of analysis and chemical properties of coumarins. Part 2. Chromatographic and volumetric methods of analysis,” (1987), Dep. VINITI [Paper deposited in the All-Union Institute of Scientific and Technical Information], No. 1903-V87.
J. M. Fremy and T. Carion, Analysis,12, No. 3, 103–112 (1984).
V. Betina, J. Chromatogr.,477, No. 2, 187–233 (1989).
T. M. Scott, J. Assoc. Offic. Anal. Chem.,72, No. 1, 75–80 (1989).
T. M. Swager and J. H. Cardellina, Phytochemistry,24, No. 4, 805–813 (1985).
K. Ogihara, K. Munesada, T. Yamamitsu, and T. Suga, Phytochemistry,28, No. 4, 1061–1067 (1989).
G. Szabo, H. Greger, and O. Hoter, Phytochemistry,24, No. 3, 537–541 (1985).
J. Jakupovic, R. Boener, and S. Schuster, Phytochemistry,26, No. 4, 1069–1075 (1987).
G. Appendino, S. Togliapietra, P. Gariboldi, G. M. Nano, and V. Picci, Phytochemistry,27, No. 11, 3619–3624 (1988).
F. Imai, T. Kinashita, and U. Sankawa, Chem. Pharm. Bull.,37, No. 2, 358–362 (1989).
J. H. Henke, Lab. Prax.,10, No. 6, 668–679 (1986).
B. Sledzinska, B. Makuch, Z. Majer, H. Snopen, and Y. Ostapzuk, Polish Patent No. 253, 758 (1989).
R. Aquino, M. D'Agostino, F. De Simone, and C. Rizza, Phytochemistry,27, No. 6, 1827–1830 (1988).
O. Ceska, S. K. Chaudhary, P. Warrington, M. J. Ashwood-Smith, G. W. Bushell, and G. A. Poulton, Phytochemistry,27, No. 7, 2083–2087 (1988).
B. A. Bidlingmeyer, Preparative Liquid Chromatography, Elsevier, Amsterdam, (1987).
B. R. Baric, A. K. Dey, and A. Chatterjee, Phytochemistry,22, No. 10, 2273–2275 (1983).
T. Sh. Wu, M. J. Lion, and Ch. Sh. Kuon, Phytochemistry,28, No. 1, 293–294 (1989).
T. Sh. Wu, M. J. Lion, and T. T. Jong, Phytochemistry,28, No. 10, 2873–2874 (1989).
V. Kumar, J. Reisch, and D. B. M. Wickremaratne, Phytochemistry,26, No. 2, 511–514 (1987).
G. C. Zogg, Sz. Nyiredy, and O. Sticher, Chromatographia,27, Nos. 11–12, 592–595 (1989).
K. Hunter, J. Chromatogr.,270, 267–276 (1983).
K. Hunter, J. Chromatogr.,270, 277–283 (1983).
E. R. DiPaolo, M. O. Hamburger, H. Stoeckli-Evans, C. Roggers, and K. Hostettmann, Helv. Chim. Acta,72, No. 7, 1455–1462 (1989).
C. Zdero, F. Bohlmann, and H. M. Niemeyer, Phytochemistry,27, 2953–2959 (1988).
C. Zdero, F. Bohlmann, and R. M. King, Phytochemistry,25, No. 12, 2873–2882 (1986).
G. Giammona, L. Camanda, O. Listro, and S. Palazzo, Boll. Chim. Farm.,128, No. 7–8, 225–228 (1989).
M. A. Dubois, M. Wiener, and H. Wagner, Phytochemistry,29, No. 10, 3369–3371 (1990).
B. C. Van Wagenen, J. Huddleston, and J. H. Cardellina, J. Nat. Prod.,51, No. 1, 136–141 (1988).
M. Bittner, J. Jakupovic, F. Bohlmann, and M. Silva, Phytochemistry,28, No. 7, 1887–1890 (1989).
J. A. Marco, Phytochemistry,28, No. 11, 3121–3126 (1989).
G. C. Zogg, Sz. Nyiredy, and O. Sticher, J. Liquid Chromatogr.,12, No. 11, 2031–2042 (1989).
G. C. Zogg, Sz. Nyiredy, and O. Sticher, J. Liquid Chromatogr.,12, No. 11, 2049–2065 (1989).
S. Nyiredy, K. Dollenbach-Toelke, G. C. Zogg, and O. Sticher, J. Chromatogr.,499, 453–462 (1990).
K. Glowniak, E. Soczewinski, and T. Wawrzynowicz, Chem. Anal. (Warsaw),32, No. 5, 797–811 (1987).
M. Hamburger, H. Stoeckli-Evans, and K. Hostettmann, Helv. Chim. Acta,67, No. 7, 1729–1733 (1984).
D. V. Banthorpe and G. D. Brown, Phytochemistry,28, No. 11, 3003–3007 (1989).
D. McHale, P. P. Khopnaz, and J. B. Sheridan, Phytochemistry,26, No. 9, 2547–2549 (1987).
C. A. J. Erdelmeier and O. Sticher, Planta Med., No. 5, 407–409 (1985).
D. Ashkenazy, J. Friedman, Y. Koshman, Planta Med.,47, No. 4, 218–220 (1983).
F. Speckenbach, GIT-Suppl.,33, 69–78 (1989).
T. Wawrzynowicz, M. Waksmundzka-Hainas, and M. L. Bieganowska, Chromatographia,28, No. 3–4, 161–166 (1989).
J. Fitos and M. Simonyi, J. Chromatogr.,450, No. 2, 217–220 (1988).
J. Szinai, M. Simonyi, J. Fitos, Zs. Tegyey, and A. Maguar, Eur. J. Drug Metab. Pharmacokinet.,15, No. 2, 103–107 (1990).
J. W. Wainer and Ya-Qin Chu, J. Chromatogr.,455, 316–322 (1988).
U. Völker and J. X. De Vries, Arch. Pharmacol.,339, 117 (1989).
J. Hermansson, TRAC: Trends Anal. Chem.,8, No. 7, 251–259 (1989).
P. V. Kuznetsov, I. V. Fedorov, and V. V. Shkarenda, New Drugs from Plants of Siberia and the Far East: Abstracts of Lectures at an All-Union Conference [in Russian], Tomsk, Vol. 2 (1989), pp. 89–90.
P. V. Kuznetsov, V. V. Shkarenda, and I. V. Fedorov, Abstracts of Lectures at a Scientific and Practical Conference on Reserves for the Improvement of the Drug Supplied to the Population of the RSFR and of a Plenum of the All-Russian Society of Pharmacists, March 12, 1991. Section III [in Russian], Vladimir (1991), pp. 40–41.
I. B. Barsegyan, S. S. Barsegyan, I. V. Fedorov, V. V. Shkarenda, and A. V. Mahlev, Scientific and Practical Conference, Kemerovo, June 5–6, 1990 [in Russian], Kemerovo (1990), p. 29.
V. V. Shkarenda, Abstracts of Lectures of an Interuniversity Scientific and Practical Conference on Questions of Theoretical and Clinical Medicine, April 24–26, 1991 [in Russian], Kemerovo (1991), pp. 49–50.
P. V. Kuznetsov, V. V. Shkarenda, and O. V. Suptelova, Abstracts of Lectures at a Scientific and Practical Conference on the Present State and Prospects of the Development of Pharmacy in Siberia and the Far East, Tomsk, September 3–5, 1991 [in Russian], Tomsk, Part 1 (1991), pp. 148–149.
V. V. Shkarenda, Sixth Conference of Young Scientists on Human Health in Siberia, Krasnoyarsk, October 29-November 2, 1990 [in Russian], Krasnoyarsk (1990), [in Russian], Krasnoyarsk (1990), pp. 139–140.
P. V. Kuznetsov and V. V. Shkarenda, Khim.-Farm. Zh.,25, No. 4, 72–75 (1991).
P. V. Kuznetsov and V. V. Shkarenda, Khim. Prir. Soedin., No. 4, 475 (1991).
M. Bittner, J. Jacupovic, F. Bohlmann, M. Grenz, and M. Silva, Phytochemistry,27, No. 10, 3263–3266 (1988).
C. Zdero, F. Bohlmann, and H. M. Niemeyer, Phytochemistry,27, No. 6, 1821–1825 (1988).
O. Ceska, S. Choudhary, P. Warrington, G. Poulton, and M. Ashwood-Smith, Experientia,42, Nos. 11–12, 1302–1304 (1986).
L. R. C. Locar and S. Delben, Phytochemistry,27, No. 4, 1073–1077 (1988).
F. Kurasaki, Y. Kizawa, and A. Nishi, Eur. J. Biochem.,185, No. 1, 85–89 (1989).
M. Fernanda, M. Borges, and M. Pinto, J. Liquid Chromatogr.,12, No. 12, 2345–2354 (1989).
Y. F. Hallock, J. Clardy, D. S. Kenfield, and G. Strobel, Phytochemistry,27, No. 10, 3123–3125 (1988).
A. E. Desjardins, G. F. Spencer, and R. D. Plattner, Phytochemistry,28, No. 11, 2963–2965 (1989).
E. Moran, R. O'Kennedy, and R. D. Thernes, J. Chromatogr. Biomed. Appl.,416, No. 1, 165–169 (1987).
D. C. Mays, S. G. Hecht, S. E. Unger, Ch. M. Pacula, J. M. Climie, D. E. Sharp, and N. Gerber, Drug Metab. Disposit: Biol. Fate Chem.,15, No. 3, 318–328 (1987).
Y. W. J. Wong and P. J. Davis, J. Chromatogr.,469, 281–291 (1989).
V. P. A. Frank, M. C. Winn, and J. G. A. Hassing, J. Chromatogr. Biomed., Appl.,487, No. 2, 489–495 (1989).
J. D. Rizzo and P. J. Davis, J. Pharm. Sci.,78, No. 3, 183–189 (1989).
S. K. Pratt, M. J. Winn, and R. K. Park, J. Pharm. Pharmacol.,41, No. 11, 743–746 (1989).
H. H. W. Thijssen, L. G. Baars, and M. J. Reijnders, J. Chromatogr. Biomed. Appl.,274, 231–238 (1983).
P. M. Ueland, G. Karalheim, P. E. Lonning, and S. Kvinnsland, Ther. Drug. Monit.,7, No. 3, 320–335 (1985).
J. M. Steyn and V. D. Merve, J. Chromatogr. Biomed. Appl.,378, 254–260 (1986).
F. Susanto, S. Humfeld, H. Reinauer, and R. Meschig, Chromatographia,21, No. 8, 443–446 (1986).
D. C. Spink, K. M. Aldaus, and L. S. Kaminsky, Anal. Biochem.,177, No. 2, 307–313 (1989).
L. M. Stolk, R. Derunter, A. Saadawi, A. H. Siddiqui, and R. H. Cormane, J. Chromatogr. Biomed. Appl.,423, 383–386 (1987).
B. Maupas, C. Fenech, and F. Guyon, Analusis,17, No. 8, 468–472 (1989).
M. Arman and F. Jamali, J. Chromatogr. Biomed. Appl.,272, No. 2, 406–410 (1983).
J. X. De Vries, J. Harenberg, E. Walter, R. Zimmermann, and M. Simon, J. Chromatogr. Biomed. Appl.,231, No. 1, 83–92 (1982).
E. Bingler-Timeus and H. Becker, Sci. Pharm.,S1, No. 2, 503–505 (1983).
E. S. Moore, J. Assoc. Offic. Anal. Chem.,70, No. 5, 834–836 (1987).
A. I. Grizodub, V. P. Georgievskii, M. G. Levin, N. P. Khavanskaya, N. N. Asmolova, Proceedings of the Second Congress of Georgian Pharmacists, Tbilisi, December 15–18, 1987 [in Russian], Tbilisi (1987), pp. 193–196.
H. G. Eigendorf, G. Möschwitzer, and R. Budde, Die Pharmazie,44, No. 9, 645–646 (1989).
F. O. Müller, J. M. Steyn, H. K. L. Hundt, and H. G. Luus, S. Afr. Med. J.,74, No. 11, 566–567 (1988).
K. Van de Castelle, H. Geiger, and Ch. F. Van Sumere, J. Chromatogr.,258, 111–124 (1983).
A. Carisano and G. Della Tarre, J. Chromatogr.,355, 340–344 (1986).
A. Simonella, L. Torreti, C. Filipponi, A. Falgiani, and L. Ambrosii, J. High Resolut. Chromatogr. Chromatogr. Commun.,10, No. 11, 626–628 (1987).
M. F. Morin, N. Merlet, M. Dore, and J. C. Lechevin, Analysis,17, No. 9, 526–531 (1989).
V. Lander, M. Wörner, Ch. Kirchenmayer, H. Wintoch, and P. Schreir, Z. Lebensm.-Untersuch. Forsch.,190, No. 5, 410–413 (1990).
N. Bradburn, K. Jewers, B. D. Jones, and J. J. Tomlins, Chromatographia,28, Nos. 11–12, 541–544 (1989).
K. Hunter, E. A. Sharp, and A. Newton, J. Chromatogr.,435, 83–95 (1988).
P. J. Schoenmakers, Optimization of Chromatographic Selectivity, Elsevier, Amsterdam (1986).
K. Glowniak, T. Wawrzynowicz, and E. Soczewinski, Chromatography 85: Proceedings of the Budapest Chromatography Conference, June 11–14, 1985, Budapest (1986), pp. 251–261.
E. Katz, Quantitative Analysis Using Chromatographic Techniques, Wiley, New York (1987).
M. E. Perel'son, Yu. N. Sheinker, and A. A. Savina, Spectra and Structures of Coumarins, Chromones, and Xanthones [in Russian], Meditsina, Moscow (1975).
R. Duren and H. A. Diehl, J. Chromatogr.,445, No. 1, 49–58 (1988).
H. J. Thompson and S. A. Brown, J. Chromatogr.,314, 323–336 (1984).
Sz. Nyiredy, K. Dollenbach-Toelke, and O. Sticher, J. Liquid Chromatogr.,12, Nos. 1–2, 95–116 (1989).
Y. Motano, T. Okuyma, and S. Shibata, Planta Med.,52, No. 2, 135–138 (1986).
H. Vuorela, K. Dollenbach-Toelke, and Sz. Nyiredy, Planta Med.,55, No. 2, 181–184 (1989).
J. Sakakibara, T. Okyama, and S. Shibata, Planta Med.,50, No. 2, 117–120 (1984).
C. Kawasaki, T. Okyama, and S. Shibata, Planta Med.,50, No. 6, 492–496 (1984).
R. G. Enriquez, M. L. Romero, L. S. Escobar, P. Joseph-Natan, and W. F. Reynolds, J. Chromatogr.,287, No. 1, 209–214 (1984).
G. Parasi, J. A. Baugloni, and F. Mascia, Bull. Soc. Natur. Napoli,95, 155–159 (1986).
A. Shibukawa, T. Nakagawa, M. Miyake, and H. Tanaka, Chem. Pharm. Bull.,36, No. 5, 1930–1933 (1988).
J. D. Rizzo and P. J. Davis, Xenobiotica,18, No. 12, 1425–1437 (1988).
H. H. W. Thijssen and L. G. M. Baars, J. Pharmacol. Exp. Ther.,243, No. 3, 1082–1088 (1987).
Huang Junxiong, Huanjing Huaxue (Environ. Chem.),3, No. 5, 65–69 (1984).
A. W. Ascher, J. Chromatogr.,447, No. 1, 272–276 (1988).
J. L. Peuch, P. Rabier, and M. Moutounet, J. Chromatogr.,457, 431–436 (1988).
D. Strack, J. Heilemann, V. Wray, and H. Dires, Phytochemistry,28, No. 8, 2071–2078 (1989).
K. Sagara, T. Oshima, and T. Yoshida, J. Chromatogr.409, 365–370 (1987).
J. M. Anderson and W. B. Pedersen, J. Chromatogr.,259, 131–139 (1983).
H. Schultz and G. Albroscheit, J. Chromatogr.,442, 353–361 (1988).
R. V. Tamma, G. C. Miller, and R. Everett, J. Chromatogr.,322, 236–239 (1985).
P. Pietta, E. Manera, P. Ceva, J. Chromatogr.,404, 279–281 (1987).
H. Wagner, B. Geyer, and Y. Kiso, Planta Med.,52, No. 5, 370–374 (1986).
U. Völker and J. X. De Vries, Arch. Pharmacol.,339, 117 (1989).
C. A. J. Erdelmeier, B. Meier, and o. sticher, J. Chromatogr.,346, 456 (1984).
M. Tod, M. Prevot, M. Poulton, R. Farinotti, J. Chalom, G. Mahuzier, Anal. Chim. Acta,223, 309–317 (1989).
K. S. Khetwal and R. P. Pathak, Pap. Pittsburg Conf. Expos. Anal. Chem. Appl. Spectrosc., New Orleans, La., February 25–March 1, 1985, pp. 1, 57.
G. Sontag, E. N. Frank, and A. Nikiforov, Z. Anal. Chem.,314, No. 6, 572–576 (1983).
T. Sone, M. Isobe, E. Takabatake, N. Ozawa, and T. Watabe, J. Pharmacobio-Dyn.,12, No. 3, 149–158 (1989).
L. S. Teslov, L. N. Koretskaya, and G. I. Tsareva, Khim. Prir. Soedin., No. 3, 387 (1983).
J. A. Marco, O. Barbera, and J. Sanchez-Parareda, J. Nat. Prod.,50, No. 4, 774–775 (1987).
B. A. Klyashchitskii, I. V. Mezhova, and V. I. Shvets, Usp. Biol. Khim.,27, 187–220 (1986).
S. K. Chaudhary, O. Ceska, and C. Tetu, Planta Med.,52, No. 6, 462–464 (1986).
E. H. Oertli, R. C. Beier, G. W. Ivie, L. D. Rowe, Phytochemistry,23, No. 2, 439–441 (1984).
E. Lemmich and L. Gylle, Phytochemistry,27, No. 11, 3688–3689 (1988).
M. Bittner, J. Jakupovic, F. Bohlmann, and M. Silva, Phytochemistry,27, No. 12, 3845–3847 (1988).
O. Ceska, S. K. Chaudhary, and P. J. Warrington, Phytochemistry,26, No. 1, 165–169 (1987).
K. Sagara, T. Oshima, and S. Sakamoto, J. Chromatogr.,398, 448–454 (1987).
J. Kopesky, J. Toman, D. Saman, L. Bartova, L. Novotny, and J. Harmatha, Ceskoslowenska Farmacie,39, No. 3, 130–132 (1989).
R. D. Thompson and T. J. Hoffmann, J. Chromatogr.,438, 369–382 (1988).
K. Glowniak and M. L. Bieganowska, J. Liquid Chromatogr.,8, No. 16, 2927–2947 (1985).
O. Trakou, S. Thilinos, and C. Harvala, Plant. Med. Phytother.,22, No. 4, 261–266 (1988).
J. L. Peuch and M. Moutounet, J. Assoc. Offic. Anal. Chen.,71, No. 3, 512–514 (1988).
K. Knobloch and J. Prochazka, in: Paper Chromatography, I. M. Hais and K. Macek (eds.), Academic Press, New York, 3rd Ed. (1962) [Russian translation from the Czech], Mir, Moscow (1962), pp. 326–329.
D. Treutter, J. Chromatogr.,436, 490–494 (1988).
F. Yugi, G. Mingyuan, and Z. Youjie, J. Cent. China Norm. Univ.,22, No. 4, 452–454 (1988).
N. Le-Van, Phytochemistry,23, No. 5, 1204–1205 (1984).
H. H. W. Thijssenn, L. G. M. Baars, and G. M. J. Jonssen, Drug. Metab. Disposit., Biol. Fate Chem.,16, No. 5, 744–748 (1988).
T. Suortti, A. von Wright, and A. Koskinen, Phytochemistry,22, No. 12, 2873–2874 (1983).
A. S. Sidhu, J. M. Kennedy, and S. Deelbe, J. Chromatogr.,391, 233–242 (1987).
T. A. Van Beek and A. Blaakmeer, J. Chromatogr.,464, 375–386 (1986).
M. Sharmon, A. L. Patey, and J. Gilbert, J. Chromatogr.,474, 457–461 (1989).
P. Chambon, S. D. Dano, R. Chambon, and A. Geahchan, J. Chromatogr.259, 372–374 (1983).
R. W. Beaver, in: 197th ACS National Meeting, Dallas, Texas, April 9–14 (1984), Abstracts of Papers, American Chemical Society, Washington, D.C. (1989), p. 8.
M. L. Bieganowska and K. Glowniak, Chromatographia,25, No. 2, 111–116 (1988).
H. Vuorela and P. Lehtonen, J. Liquid Chromatogr.,12, Nos. 1–2 221–234 (1989).
T. A. Asahara, J. Sakakibara, and T. Okuyama, Planta Med.,50, No. 6, 488–492 (1984).
M. R. Berenbaum and A. R. Zangerl, Phytochemistry,25, No. 3, 659–661 (1986).
M. R. Berenbaum, A. R. Zangerl, and J. K. Natao, Phytochemistry,23, No. 8, 1809–1810 (1984).
R. C. Beier and E. H. Oertli, Phytochemistry,22, No. 11, 2595–2597 (1983).
R. C. Beier, G. W. Ivie, E. H. Oertli, and D. L. Hobt, Food-Chem. Toxicol.,21, 163 (1989).
K. Baba, M. Taniguti, Y. Yoneda, and M. Kazawa, Phytochemistry,29, No. 1, 247–249 (1990).
C. Pettersson and C. Giolli, J. Chromatogr.,398, 247–254 (1987).
A. Hallberg, R. Isaksson, A. R. Martin, and J. Sandström. J. Am. Chem. Soc.,111, No. 12, 4387–4392 (1989).
Eisuko Isohata, Masatake Toyoda, and Yukio Saito, Bull. Nat. Inst. Hyg. Sci., No. 107, 128–132 (1989).
M. Gazdag, G. Szepesi, and L. Huszar, J. Chromatogr.,371, 227 (1986).
A. Cepeda-Saez, P. Prognon, G. Mahuzier, and J. Blais, Anal. Chim. Acta,211, Nos. 1–2, 333–337 (1988).
J. Blais, P. Prognon, and G. Mahuzier, J. Photochem. Photobiol.,2, No. 4, 455–456 (1988).
D. W. Armstrong, C.-D. Chang, and H. Lee, J. Chromatogr.,539, No. 1, 83–91 (1991).
N. Thuaud, B. Sebille, A. Dertani, and G. Lelievre, J. Chromatogr.,503, No. 2, 453–458 (1990).
B. R. Baric, A. K. Dey, and A. Chatterjee, Phytochemistry,22, No. 10, 2273–2275 (1983).
L. R. Snyder, J. Chromatogr. Sci.,16, 223 (1978).
P. Härmälä, H. Vuorela, R. Hinkkanen, and R. Hiltunen, Finnish Chemical Congress, Helsinki, November 7–9 (1989), Kemia-Kemi16, No. 10B, 1078 (1990).
P. Härmälä, H. Vuorela, P. Lehtonen, and R. Hultunen, J. Chromatogr.,507, 367–380 (1990).
Additional information
Kemerov State Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 155–172, March–April, 1992.
Rights and permissions
About this article
Cite this article
Shkarenda, V.V., Kuznetsov, P.V. Current state of the liquid column chromatography of coumarins. Chem Nat Compd 28, 131–145 (1992). https://doi.org/10.1007/BF00630161
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00630161