Furofuran lignans of Artemisia genus: Isolation, biosynthesis and biological activity

Main Article Content

Jovana D. Ickovski
Jovana Lj. Pavlović
Milan N. Mitić
Ivan R. Palić
Danijela A. Kostić
Goran M. Petrović
Gordana S. Stojanović

Abstract

Since ancient times, medicinal plants and pharmacologically active products obtained from different natural sources play an important role in human health. Plants belonging to the genus Artemisia possess a great bio­logical potential and it is a well-studied genus in the fields such as systematics (including molecular phylogenetics) and genome organization. Many species of the genus (e.g., A. absinthium, A. annua, A. vulgaris, A. abro­tanum, A. arbo­res­cens) are widely exploited, because of their high economic value as medi­cines, food and ornamentals. Withal, in such a large genus, some hiatus must inevitably exist, concerning attainments and potentials that individual species possess. Most of the studies are focused on bioactivity and pharmacology of sesquiterpene lactones. Lignans are unjustly neglected, even though they as well exhibit a wide range of bioactivities. Motivated by that fact, we tried to consolidate findings on bioactive lignans accumulated through the years, with the logical perspectives on further work on isolation and identification of new bioactive lignans and the exploitation of lignans as substances of  potential pharmacological interest.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

Article Details

How to Cite
[1]
J. D. Ickovski, “Furofuran lignans of Artemisia genus: Isolation, biosynthesis and biological activity”, J. Serb. Chem. Soc., vol. 85, no. 5, pp. 575–600, May 2020.
Section
Review

References

J. Vallès, S. Garcia, O. Hidago, J. Martín, J. Pellicer, M. Sanz, T. Garnatje, in Advances in Botanical Research, Vol. 60, J. C. Kader, M. Delseny, Eds., Academic press, London, 2011, p. 349 (https://doi.org/10.1016/B978-0-12-385851-1.00015-9)

J. Martin, M. Torrel, J. Valles, Plant Biol. 4 (2001) 372 (https://dx.doi.org/10.1055/s-2001-16462)

J. Martin, M. Torrel, J. Valles, Plant Biol. 5 (2003) 85 (https://dx.doi.org/10.1055/s-2003-37979)

L. E. Watson, P. L. Bates, T. M. Evans, M. M. Unwin, J. R. Estes, BMC Evol. Biol. 2 (2002) 17 (https://dx.doi.org/10.1186/1471-2148-2-17)

E. D. McArthur, in Proceedings of Sagebrush steppe ecosystem symposium, Boise, ID, USA, 1999, 2000, p. 9 (https://www.fs.usda.gov/treesearch/pubs/30023)

K. Bremer, C. Humphries, Bull. Nat. Hist. Mus. 23 (1993) 71 (https://ia800506.us.archive.org/25/items/bulletinofnatura90natulond/bulletinofnatura90natulond.pdf)

D. J. Mabberley, Mabberleys Plant-Book: A Portable Dictionary of Plants, Their Classifications and Uses, Cambridge University Press, Cambridge, 2008, ISBN: 9781107115026

J. Pellicer, J. Vallès, A. A. Korobkov, T. Garnatje, Taxon 60 (2011) 691 (https://dx.doi.org/10.1002/tax.603006)

J. Vallès, M. Torrell, T. Garnatje, N. Garcia-Jacas, R. Vilatersana, A. Susanna, Plant Biol. 5 (2003) 274 (https://dx.doi.org/10.1055/s-2003-40790)

M. Sanz, R. Vilatersana, O. Hidalgo, N. Garcia-Jacas, A. Susanna, G. M. Schneeweiss, J. Vallès, Taxon 57 (2008) 66 (https://dx.doi.org/10.2307/25065949)

S. DAndrea, R. Caramiello, S. Ghignone, C. Siniscalco, Plant Biosyst. 137 (2003) 121 (https://dx.doi.org/10.1080/11263500312331351381)

M. Q. Hayat, M. Ashraf, M. A. Khan, G. Yasmin, N. Shaheen, S. Jabeen, Int. J. Agric. Biol. 11 (2009) 542 (http://www.fspublishers.org/published_papers/91324_..pdf)

C. Oberprieler, R. Vogt, L. E. Watson, in Flowering Plants. Eudicots: Asterales. The families and genera of vascular plants, Vol. 8, J. W. Kadereit, C. Jeffrey, Eds., Springer-

-Verlag, Berlin, 2007, p. 342 ISBN: 978-3-540-31051-8

G. D. Brown, Molecules 15 (2010) 7603 (https://dx.doi.org/10.3390/molecules15117603)

A. Rustaiyan, S. Masoudi, Phytochem. Lett. 4 (2011) 440 (https://dx.doi.org/10.1016/j.phytol.2011.07.003)

M. Soliman, Arch. Phytopathol. Plant Protect. 40 (2007) 128 (https://dx.doi.org/10.1080/03235400500355808)

P. Blagojević, N. Radulović, R. Palić, G. Stojanović, J. Agric. Food Chem. 54 (2006) 4780 (https://dx.doi.org/10.1021/jf060123o)

H. Q. Tang, J. Hu, L. Yang, R. X. Tan, Planta Med. 66 (2000) 391 (https://dx.doi.org/10.1055/s-2000-8538)

H. M. Kim, J. Y. Seo, K. H. Liu, J. S. Kim PloS One 9 (2014) e101486 (https://dx.doi.org/10.1371/journal.pone.0101486)

M. A. Foglio, P. C. Dias, M. A. Antonio, A. Possenti, R. A. F. Rodrigues, É. F. da Silva, V. L. G. Rehder, J. E. de Carvalho, Planta Med. 68 (2002) 515 (https://dx.doi.org/10.1055/s-2002-32570)

M. Sayyah, L. Nadjafnia, M. Kamalinejad, J. Ethnopharmacol. 94 (2004) 283 (https://dx.doi.org/10.1016/j.jep.2004.05.021)

G. A. R. A. Jaleel, H. M. I. Abdallah, N. E. L. S. Gomaa, Asian Pac. J. Trop. Biomed. 6 (2016) 44 (https://dx.doi.org/10.1016/j.apjtb.2015.10.005)

I. A. Graham, K. Besser, S. Blumer, C. A. Branigan, T. Czechowshi, L. Elias, I. Guterman, L. Harvey, P. G. Isaac, A. M. Khan, T. R. Larson, Y. Li, T. Pawson, T. Penfield, A. M. Rae, D. A. Rathbone, S. Reid, J. Ross, M. F. Smalwood, V. Sequra, T. Townsend, D. Vyas, T. Winzer, D. Bowles, Science 327 (2010) 328 (https://dx.doi.org/10.1126/science.1182612)

W. J. M. Lommen, E. Schenk, H. J. Bouwmeester, F. W. A. Verstappen, Planta Med. 72 (2006) 336 (https://dx.doi.org/10.1055/s-2005-916202)

J. H. Wiersema, B. León, World economic Plants: A Standard Reference, CRC Press, Boca Raton, FL, 1999 ISBN: 0-8493-2119-0

E. A. Brisibe, E. A. Uyoh, F. Brisibe, P. M. Magalhäes, J. F. S. Ferreira, Afr. J. Biotechnol. 7 (2008) 4884 (https://www.ajol.info/index.php/ajb/article/view/59696)

J. C. Laughlin, G. N. Heazlewood, B. M. Beattie, in Artemisia, 1st ed., C. W. Wright, Ed., Taylor & Francis, London, 2002 p. 127 ISBN: 0-203-34643-2

D. D. Zhai, H. Z. Jin, J. J. Zhong, Chin. Chem. Let. 21 (2010) 590 (https://dx.doi.org/10.1016/j.cclet.2010.01.034)

M. N. Binet, D. van Tuinen, N. Deprêtre, N. Koszela, C. Chambon, S. Gianinazzi, Mycorrhiza 21 (2011) 523 (https://dx.doi.org/10.1007/s00572-010-0354-y)

L. Bézanger-Beauquesne, M. Pinkas, M. Torck, F. Trotin, Plantes médicinales des régions tempérées 2nd ed., Maloine Publishers, Paris, 1990 ISBN: 2-224-02009-0

R. N. Kulkarni, in Artemisia, 1st ed., C. W. Wright, Ed., Taylor & Francis, London, 2002 p. 97 ISBN: 0-203-34643-2

M. Heinrich, in Artemisia, 1st ed., C. W. Wright, Ed., Taylor & Francis, London, 2002, p. 87 ISBN: 0-203-34643-2

P. Proksch, in Artemisia, 1st ed., C. W. Wright, Ed., Taylor & Francis, London, 2002, p. 81 ISBN: 0-203-34643-2

P. A. Linley, in Artemisia, 1st ed., C. W. Wright, Ed., Taylor & Francis, London, 2002, p. 112 ISBN: 0-203-34643-2

E. Hsu, Trans. R. Soc. Trop. Med. Hyg. 100 (2006) 505 (https://dx.doi.org/10.1016/j.trstmh.2005.09.020)

M. Willkox, J. Altern. Complement. Med. 15 (2009) 101 (https://dx.doi.org/10.1089/acm.2008.0327)

M. A. Bonet Galobart, X. J. Vallès, Plantes, remeis i cultura popular del Montseny: Etnobotànica duna reserva de la biosfera, Brau Edicions, Figueres, Museu de Granollers-Ciencies Naturals, Granollers, 2006 ISBN: 9788487790546

S. Sanmi, Chado: The Way of Tea. A Japanese Tea Masters Almanac, Tuttle Pubishing, Boston, MA, 2005 ISBN: 13:978-4629-0036-7

J. Cullen, in The European Garden Flora. A Manual for the Identification of Plants Cultivated in Europe, Both Out-of-Doors and Under Glass, Vol. 6, J. Cullen, J. C. M. Alexander, C. D. Brickell, J. R. Edmondson, P. S. Green, V. H. Heywood, P. M. Jorgenson, S. L. Jury, S. G. Knees, H. S. Maxwell, D. M. Miller, N. K. B. Robson, S. M. Walters, P. F. Yeo, Eds., Cambridge University Press, Cambridge, 2000, p. 601 ISBN: 0-521-42097-0

S. Garcia, T. Garnatje, J. D. Twibell, J. Vallès, Genome 49 (2006) 244 (https://dx.doi.org/10.1139/g05-105)

G. E. Schuman, G. S. Howard, J. Range. Manage. 31 (1978) 392 (https://dx.doi.org/10.2307/3897367)

J. F. Ferreira, D. L. Luthria, T. Sasaki, A. Heyerick, Molecules 15 (2010) 3135 (https://dx.doi.org/10.3390/molecules15053135)

S. J. Lee, H. Y. Chung, C. G. A. Maier, A. R. Wood, R. A. Dixon, T. J. Mabry, J. Agric. Food Chem. 46 (1998) 3325 (https://dx.doi.org/10.1021/jf9801264)

K. M. Valant-Vetschera, R. Fisher, E. Wollenweber, Biochem. Syst. Ecol. 31 (2003) 487 (https://dx.doi.org/10.1016/S0305-1978(02)00178-3)

A. R. Bilia, P. Melillo de Malghaes, M. C. Bergonzi, F. F. Vincieri, Phytomedicine 13 (2006) 487 (https://dx.doi.org/10.1016/j.phymed.2006.01.008)

A. Aberham, S. S. Cicek, P. Schneider, H. Stuppner, J. Agric. Food Chem. 58 (2010) 10817 (https://dx.doi.org/10.1021/jf1022059)

R. X. Tan, H. Lu, J. L. Wolfender, T. T. Yu, W. F. Zheng, L. Yang, S. Gafner, K. Hostettmann, Planta Med. 65 (1999) 64 (https://dx.doi.org/10.1055/s-1999-13965)

R. G. Kelsey, F. Shafizadek, Phytochemistry 18 (1979) 1591 (https://dx.doi.org/10.1016/0031-9422(79)80167-3)

N. S. Radulović, P. D. Blagojević, B. K. Zlatković, R. M. Palić, S. Afr. J. Chem. 62 (2009) 30 (http://www.scielo.org.za/scielo.php?script=sci_arttext&pid=S0379-43502009000100034)

N. S. Radulović, P. J. Randjelović, N. M. Stojanović, P. D. Blagojević, Z. Z. Stojanović-

-Radić, I. R. Ilić, V. B. Djordjević, Food Chem. Toxicol. 58 (2013) 37 (https://dx.doi.org/10.1016/j.fct.2013.04.016)

T. Efferth, A. Sauerbrey, A. Olbrich, E. Gebhart, P. Rauch, H. O. Weber, J. G. Henqstler, M. E. Halatsch, M. Volm, K. D. Tew, D. D. Ross, J. O. Funk, Mol. Pharmacol. 64 (2003) 382 (https://dx.doi.org/10.1124/mol.64.2.382)

Q. Li, P. J. Weina, W. K. Milhous, Curr. Drug Ther. 2 (2007) 210 (https://dx.doi.org/10.2174/157488507781695649)

E. Nibret, M. Wink, Phytomedicine 17 (2010) 369 (https://dx.doi.org/10.1016/j.phymed.2009.07.016)

Y. Tariku, A. Hymete, A. Hailu, J. Rohloff, Chem. Biodivers. 7 (2010) 1009 (https://dx.doi.org/10.1002/cbdv.200900375)

Y. Tariku, A. Hymete, A. Hailu, J. Rohloff, Chem. Biodivers. 8 (2011) 614 (https://dx.doi.org/10.1002/cbdv.201000331)

M. Chadwick, H. Trewin, F. Gawthrop, C. Wagstaff, Int. J. Mol. Sci. 14 (2013) 12780 (https://dx.doi.org/10.3390/ijms140612780)

R. Ortet, S. Prado, E. L. Regaldo, A. V. Frederick, J. Media, J. Mendiola, O. P. Thomas, J. Ethnopharmacol. 138 (2011) 637 (https://dx.doi.org/10.1016/j.jep.2011.09.039)

A. E. Vega, G. H. Wendel, A. O. Maria, L. Pelzer, J. Ethnopharmacol. 124 (2009) 653 (https://dx.doi.org/10.1016/j.jep.2009.04.051)

T. Guardia, A. O. Juarez, E. Guerreiro, J. Guzmán, L. Pelzer, J. Ethnopharmacol. 88 (2003) 195 (https://dx.doi.org/10.1016/S0378-8741(03)00211-3)

B. Ivanescu, A. Miron, A. Corciova, J. Anal. Methods Chem. 2015 (2015) 1 (http://dx.doi.org/10.1155/2015/247685)

C. Liu, Chin. Herb. Med. 9 (2017) 101 (https://dx.doi.org/10.1016/S1674-6384(17)60084-4)

H. Wagner, in The Biology and Chemistry of the Compositae, Vol. 2, V. H. Heywood, J. B. Harborne, B. L. Turner Eds., Academic Press, London, 1977, p. 412 ISBN: 0123468019

T. E. Shaikenov, S. M. Adekenov, N. N. Belyaev, G. K. Zakiryanova, in Arglabin. Its Structure, Properties and Usage, Economy Printing, Portsmouth, VA, 1997, p. 21 (https://www.researchgate.net/profile/Nikolai_Belyaev/publication/260283583_Mechanism_of_action_of_the_sesquiterpene_from_Artemisia_glabella_Arglabin_in_transformed_tumor_cells/links/00463530780bfcea34000000/Mechanism-of-action-of-the-sesquiterpene-from-Artemisia-glabella-Arglabin-in-transformed-tumor-cells.pdf.)

J. L. Rios, R. M. Giner, J. M. Prieto, New findings on the bioactivity of lignans, in Bio¬act¬ive Natural Products. Studies in Natural Products Chemistry, Vol. 26G, A. ur-Rahman, Ed., Elsevier Science, Amsterdam, 2002, p. 183 (https://dx.doi.org/10.1016/S1572-5995(02)80008-4)

H. Satake, E. Ono, J. Murata, J. Agric. Food Chem. 61 (2013) 11721 (https://dx.doi.org/10.1021/jf4007104)

A. Oliva, R. A. Moraes, S. B. Watson, S. O. Duke, F. E. Dayan, Pestic. Biochem. Phys. 72 (2002) 45 (https://dx.doi.org/10.1006/pest.2002.2582)

J. Harmatha, L. Dinan, Phytochem. Rev. 2 (2003) 321 (https://dx.doi.org/10.1023/B:PHYT.0000045494.98645.a3)

H. Nishiwaki, M. Kumamoto, Y. Shuto, S. Yamauchi, J. Agric. Food Chem. 59 (2011) 13089 (https://dx.doi.org/10.1021/jf203222w)

P. Carillo, C. Cozzolino, B. DAbrosca, F. Nacca, M. DellaGreca, A. Fiorentio, A. Fuggi, The Open Bioact. Compd. J. 3 (2010) 18 (https://dx.doi.org/10.2174/1874847301003010018)

N. M. Saarinen, A. Wärri, M. Airio, A. Smeds, S. Mäkelä, Mol. Nutr. Food Res. 51 (2007) 857 (https://dx.doi.org/10.1002/mnfr.200600240)

K. Buck, A. K. Zaineddin, A. Vrieling, J Linseisen, J. Chang-Claude, Am. J. Clin. Nutr. 92 (2010) 141 (https://dx.doi.org/10.3945/ajcn.2009.28573)

M. Gordaliza, M. A. Castro, J. M. del Corral, A. S. Feliciano, Curr. Pharm. Des. 6 (2000) 1811 (https://dx.doi.org/10.2174/1381612003398582)

P. A. S. Alphonse, R. E. Aluko, Discovery Phytomedicine 2 (2015) 12 (https://doi.org/10.15562/PHYTOMEDICINE.2015.24)

A. Bylund, N. Saarinen, J. X. Zhang, A. Bergh, A. Widmark, A. Johansson, E. Lundin, H. Adlercreutz, G. Hallmans, P Stattin, S. Makela, Exp. Biol. Med. 230 (2005) 217 (https://dx.doi.org/10.1177/153537020523000308)

G. L. Zhang, N. Li, Y. H. Wang, Y. T. Zheng, Z. Zhang, M. W. Wang, J. Nat. Prod. 70 (2007) 662 (https://dx.doi.org/10.1021/np0605236)

D. Nakano, C. Itoh, M. Takaoka, Y. Kiso, T. Tanaka, Y. Matsumura, Biol. Pharm. Bull. 25 (2002) 1247 ( https://dx.doi.org/10.1248/bpb.25.1247)

E. Tibiriçá, Cardiovasc. Drug Rev. 19 (2001) 313 (https://dx.doi.org/10.1111/j.1527-3466.2001.tb00073.x)

M. Saleem, H. J. Kim, M. S. Ali, Y. S. Lee, Nat. Prod. Rep. 22 (2005) 696 (https://dx.doi.org/10.1039/b514045p)

M. Azam, M. Ajitha, Phyllanthin, Int. J. Pharmacogn. Phytochem. Res. 9 (2017) 1081 (https://dx.doi.org/10.25258/phyto.v9i08.9615)

A. I. Smeds, P. C. Eklund, R. E. Sjöholm, S. M. Willför, S. Nishibe, T. Deyama, B. R. Holmbom, J. Agric. Food Chem. 55 (2007) 1337 (https://dx.doi.org/10.1021/jf0629134)

J. L. Peñalvo, S. M. Heinonen, A. M. Aura, H. Adlercreutz, J. Nutr. 135 (2005) 56 (https://dx.doi.org/10.1093/jn/135.5.1056)

J. Peterson, J. Dwayer, H. Adlercreutz, A. Scalbert, P. Jacques, M. L. McCullough, Nutr. Rev. 68 (2010) 571 (https://dx.doi.org/10.1111/j.1753-4887.2010.00319.x)

J. L. Peñalvo, K. M. Haajanen, N. Botting, H. Adlercreutz, J. Agric. Food Chem. 53 (2005) 9342 (https://dx.doi.org/10.1021/jf051488w)

H. Satake, T. Koyama, S. E. Bahabadi, E. Matsumoto, E. Ono, J. Murata, Metabolites 5 (2015) 270 (https://dx.doi.org/10.3390/metabo5020270)

T. Umezawa, Wood Res. 90 (2003) 27 (http://hdl.handle.net/2433/53098)

S. Suzuki, T. Umezawa, J. Wood Sci. 53 (2007) 273 (https://dx.doi.org/10.1007/s10086-007-0892-x)

J. L. Peñalvo, H. Adlercreutz, M. Uehara, A. Ristimaki, S. Watanabe, J. Agric. Food Chem. 56 (2008) 401 (https://dx.doi.org/10.1021/jf072695u)

N. Hata, Y. Hayashi, E. Ono, H. Satake, A. Kobayashi, T. Muranaka, A. Okazawa, Plant Biotechnol. 30 (2013) 1 (https://dx.doi.org/10.5511/plantbiotechnology.12.1021a)

F. A. Macías, A. López, R. M. Varela, A. Torres, J. M. G. Molinillo, J. Agric. Food Chem. 52 (2004) 6443 (https://dx.doi.org/10.1021/jf048945d)

S. J. Liu, Z. X. Liao, C. Liu, L. J. Ji, H. F. Sun, Fitoterapia 97 (2014) 43 (https://dx.doi.org/10.1016/j.fitote.2014.05.007)

H. Greger, Planta Med. 35 (1979) 84 ISSN: 0032-0943

H. Greger, Biochem. Syst. Ecol. 9 (1981) 165 (https://dx.doi.org/10.1016/0305-1978(81)90035-1)

R. Ortet, S. Prado, E. Mouray, O. P. Thomas, Phytochemistry 69 (2008) 2961 (https://dx.doi.org/10.1016/j.phytochem.2008.09.022)

N. J. Chi, Y. Liu, H. A. Aisa, Chem. Nat. Compd. 48 (2012) 666 (https://dx.doi.org/10.1007/s10600-012-0342-x)

J. A. Marco, J. F. Sanz-Cervera, V. Garcia-Lliso, J. Valles-Xirau, Phytochemistry 44 (1997) 1133 (https://dx.doi.org/10.1016/s0031-9422(96)00720-0)

R. X. Tan, H. Q. Tang, J. Hu, B. Shuai, Phytochemistry 49 (1998) 157 (https://dx.doi.org/10.1016/S0031-9422(97)00889-3)

C. M. Ma, N. Nakamura, B. S. Min, M. Hattori, Chem. Pharm. Bull. 49 (2001) 183 (https://dx.doi.org/10.1248/cpb.49.183)

Z. Z. He, J. F. Yan, Z. J. Song, F. Ye, X. Liao, S. L. Peng, L. S. Ding, J. Nat. Prod. 72 (2009) 1198 (https://dx.doi.org/10.1021/np800643n)

R. D. Haworth, Ann. Rep. Prog. Chem. 33 (1936) 266 (https://dx.doi.org/10.1039/AR9363300228)

J. Y. Pan, S. L. Chen, M. H. Yang, J. Wu, J. Sinkkonen, K. Zou, Nat. Prod. Rep. 26 (2009) 1251 (https://dx.doi.org/10.1039/b910940d)

R. Hatfield, W. Vermerris, Plant Physiol. 126 (2001) 1351 (https://dx.doi.org/10.1104/pp.126.4.1351)

R. Vanholme, B. Demedts, K. Morreel, J. Ralph, W. Boerjan, Plant Physiol. 153 (2010) 895 (https://dx.doi.org/10.1104/pp.110.155119)

W. Boerjan, J. Ralph, M. Baucher, Ann. Rev. Plant Biol. 54 (2003) 519 (https://dx.doi.org/10.1146/annurev.arplant.54.031902.134938)

T. Umezawa, T. Okunishi, M. Shimada, Wood Res. 84 (1997) 62 (http://hdl.handle.net/2433/53199)

T. Umezawa, T. Okunishi, M. Shimada, in Lignin and lignan biosynthesis. ACS symposium series, Vol. 697, N. G. Lewis, S. Sarkanen, Eds., The American Chemical Society, Washington, DC, 1998, p. 377 (https://dx.doi.org/10.1021/bk-1998-0697.ch024)

A. I. Smeds, P. C. Eklund, S. M. Willför, Food Chem. 134 (2012) 1991 (https://dx.doi.org/10.1016/j.foodchem.2012.03.133)

T. Umezawa, Phytochem. Rev. 2 (2003) 371 (https://dx.doi.org/10.1023/B:PHYT.0000045487.02836.32)

A. Tulake, Y. Jiang, P. F. Tu, J. Chin. Pharmaceut. Sci. 21 (2012) 360 (doi:10.5246/jcps.2012.04.050)

J. Chi, B. C. Li, B. T. Yang, M. Zhang, J. Chem. Soc. Pak. 38 (2016) 533 (https://inis.iaea.org/search/search.aspx?orig_q=RN:48009478)

L. M. Weaver, K. Herrmann, Trends Plant Sci. 2 (1997) 346 (https://dx.doi.org/10.1016/S1360-1385(97)84622-5)

K. M. Herrmann, L. M. Weaver, Annu. Rev. Plant Physiol. Plant Mol. Biol. 50 (1999) 473 (https://dx.doi.org/10.1146/annurev.arplant.50.1.473)

T. Vogt, Mol. Plant 3 (2010) 2 (https://dx.doi.org/10.1093/mp/ssp106)

A. A. Dar, N. Arumugam, Bioorg. Chem. 50 (2013) 1 (https://dx.doi.org/10.1016/j.bioorg.2013.06.009)

W. Vermeris, R. Nicholson, Phenolic compound biochemistry, Springer, Amsterdam, 2006 ISBN: 1402051638

R. B. Teponno, S. Kusari, M. Spiteller, Nat. Prod. Rep. 33 (2016) 1044 (https://dx.doi.org/10.1039/c6np00021e)

S. Kitagawa, S. Nishibe, R. Benecke, H. Thieme, Chem. Pharm. Bull. 36 (1988) 3667 (https://dx.doi.org/10.1248/cpb.36.3667)

T. Umezawa, L. B. Davin, E. Yamamoto, D. G. I. Kingston, N. G. Lewis, J. Chem. Soc. Chem. Commun. 20 (1990) 1405 (https://dx.doi.org/10.1039/c39900001405)

T. Umezawa, L. B. Davin, N. G. Lewis, J. Biol. Chem. 266 (1991) 10210 (http://www.jbc.org/content/266/16/10210.short)

D. M. Pereira, P. Valentao, J. A. Pereira, P. B. Andrade, Molecules 14 (2009) 2202 (https://dx.doi.org/10.3390/molecules14062202)

L. B. Davin, N. G. Lewis, Curr. Opin. Biotechnol. 16 (2005) 407 (https://dx.doi.org/10.1016/j.copbio.2005.06.011)

P. W. Paré, H. B. Wang, L. B. Davin, N. G. Lewis, Tetrahedron Lett. 35 (1994) 4731 (https://dx.doi.org/10.1016/S0040-4039(00)76953-X)

L. B. Davin, H. B. Wang, A. L. Crowell, D. L. Bedgar, D. M. Martin, S. Sarkanen, N. G. Lewis, Science 275 (1997) 362 (https://dx.doi.org/10.1126/science.275.5298.362)

Z. Q. Xia, M. A. Costa, J. Proctor, L. B. Davin, N. G. Lewis, Phytochemistry 55 (2000) 537 (https://dx.doi.org/10.1016/S0031-9422(00)00242-9)

T. Umezawa, S. K. Ragamustari, T. Nakatsubo, S. Wada, L. Li, M. Yamamura, N. Sakakibara, T. Hattori, S. Suzuki, V. L. Chiang, Plant Biotechnol. 30 (2013) 97 (https://dx.doi.org/10.5511/plantbiotechnology.12.1230a)

S. K. Ragamustari, M. Yamamura, E. Ono, T. Hattori, S. Suzuki, H. Suzuki, D. Shibata, T. Umezawa, Plant Biotechnol. 31 (2014) 257 (https://dx.doi.org/10.5511/plantbiotechnology.14.0722a)

L. Wang, S. Yu, C. Tong, Y. Zhao, Y. Liu, C. Song, Y. Zhang, X. Zhang, Y. Wang, W. Hua, D. Li, D. Li, F. Li, J. Yu, C. Xu, X. Han, S. Huang, S. Tai, J. Wang, X. Xu, Y. Li, Y. Liu, R. K. Varshey, J. Wang, X. Zhang, Genome Biol. 15 (2014) R39 (https://dx.doi.org/10.1186/gb-2014-15-2-r39)

G. Stojanović, T. Hashimoto, Y. Asakawa, R. Palić, Biochem. Syst. Ecol. 33 (2005) 207 (https://dx.doi.org/10.1016/j.bse.2004.07.004)

S. Willför, J. Hemming, M. Reunanen, B. Holmbom, Holzforschung 57 (2003) 359 (https://dx.doi.org/10.1515/HF.2003.054)

A. Koulman, R. Bos, M. Medarde, N. Pras, W. J. Quax, Planta Med. 67 (2001) 858 (https://dx.doi.org/10.1055/s-2001-18849)

N. Takaku, D. H. Choi, K. Mikame, T. Okunishi, S. Suzuki, H. Ohashi, T. Umezawa, M. Shimada, J. Wood Sci. 47 (2001) 476 (http://hdl.handle.net/2433/53139)

L. Opletal, H. Sovová, M. Bártlová, J. Chromatogr., B 812 (2004) 357 (https://dx.doi.org/10.1016/j.jchromb.2004.07.040)

F. Kawamura, S. Kawai, H. Ohashi, Phytochemistry 44 (1997) 1351 (https://dx.doi.org/10.1016/S0031-9422(96)00705-4)

F. Abe, T. Yamauchi, A. S. C. Wan, Chem. Pharm. Bull. 36 (1988) 795 (https://dx.doi.org/10.1248/cpb.36.795)

S. Willför, J. Hemming, M. Reunanen, C. Eckerman, B. Holmbom, Holzforschung 57 (2003) 27 (https://dx.doi.org/10.1515/HF.2003.005)

S. Willför, P. Eklund, R. Sjöholm, M. Reunanen, R. Sillanpää, S. von Schoultz, J. Hemming, L. Nisula, B. Holmbom, Holzforschung 59 (2005) 413 (https://dx.doi.org/10.1515/HF.2005.067)

S. M. Willför, M. O. Ahotupa, J. E. Hemming, M. H. T. Reunanen, P. C. Eklund, R. E. Sjöholm, C. S. E. Eckerman, S. P. Pohjamo, B. R. Holmbom, J. Agric. Food Chem. 51 (2003) 7600 (https://dx.doi.org/10.1021/jf030445h)

S. Willför, L. Nisula, J. Hemming, M. Reunanen, B. Holmbom, Holzforschung 58 (2004) 335 (https://dx.doi.org/10.1515/hf.2004.052)

S. Willför, L. Nisula, J. Hemming, M. Reunanen, B. Holmbom, Holzforschung 58 (2004) 650 (https://dx.doi.org/10.1515/HF.2004.119)

J. D. Ford, K. S. Huang, H. B. Wang, L. B. Davin, N. G. Lewis, J. Nat. Prod. 64 (2001) 1388 (https://doi.org/10.1021/np010367x)

A. Kamal-Eldin, N. Peerlkamp, P. Johnsson, R. Andersson, R. E. Andersson, L. N. Lundgren, P. Aman, Phytochemistry 58 (2001) 587 (https://dx.doi.org/10.1016/S0031-9422(01)00279-5)

W. Monthog, S. Pitchuanchom, N. Nuntasen, W. Pompimon, Am. J. Appl. Sci. 8 (2011) 1268 (https://dx.doi.org/10.3844/ajassp.2011.1268.1271)

Y. Y. Chen, F. R. Chang, Y. C. Wu, J. Nat. Prod. 89 (1996) 904 (https://dx.doi.org/10.1021/np960414z)

A. M. A. P. Fernandes, A. L. Prado, L. E. S. Barata, M. Q. Paulo, N. R. Azevedo, P. H. Ferri, Phytochem. Anal. 8 (1997) 8 (https://dx.doi.org/10.1002/(SICI)1099-1565(199701)8:1<18::AID-PCA330>3.0.CO;2-B)

T. R. Sharma, B. M. Singh, N. R. Sharma, R. S. Chauhan, J. Plant Biochem. Biotechnol. 9 (2000) 49 (https://dx.doi.org/10.1007/BF03263084)

J. K. Bastos, W. J. Kopycki, C. L. Burandt, N. P. D. Nanayakkara, J. D. McChesney, Phytochem. Anal. 6 (1995) 101 (https://dx.doi.org/10.1002/pca.2800060207)

S. Yamauchi, T. Ina, T. Kirikihira, T. Masuda, Biosci. Biotechnol. Biochem. 68 (2004) 183 (https://dx.doi.org/10.1271/bbb.68.183)

H. Adlercreutz, Environ. Health Perspect. 103 (1995) 103 (https://dx.doi.org/10.1289/ehp.95103s7103)

E. Fuss, Phytochem. Rev. 2 (2003) 307 (https://dx.doi.org/10.1023/B:PHYT.0000045500.56476.f5)

S. Heinonen, T. Nurmi, K. Liukkonen, K. Poutanen, K. Wähälä, T. Deyama, S. Nishibe, H. Adlercreutz, J. Agric. Food Chem. 49 (2001) 3178 (https://dx.doi.org/10.1021/jf010038a)

J. W. Lampe, C. Atkinson, M. A. Hullar, J. AOAC Int. 89 (2006) 1174 (https://www.ncbi.nlm.nih.gov/pubmed/16915861)

Z. Liu, N. M. Saarinen, L. U. Thompson, J. Nutr. 136 (2006) 906 (https://dx.doi.org/10.1093/jn/136.4.906)

S. O. Mueller, S. Simon, K. Chae, M. Metzler, K. S. Korach, Toxicol. Sci. 80 (2004) 4 (https://dx.doi.org/10.1093/toxsci/kfh147)

P. Penttinen, J. Jaehrling, A. Damdimopoulos, J. Inzunza, J. G. Lemmen, P. van der Saag, K. Pettersson, G. Gauglitz, S. Mäkelä, I. Pongratz, Endocrinology 148 (2007) 4875 (https://dx.doi.org/10.1210/en.2007-0289)

A. During, C. Debouche, T. Raas, Y. Larondelle, J. Nutr. 142 (2012) 1798 (https://dx.doi.org/10.3945/jn.112.162453)

J. S. Truan, J. M. Chen, L. U. Thompson, Nutr. Cancer 64 (2012) 65 (https://dx.doi.org/10.1080/01635581.2012.630165)

C. J. Lee, M. H. Lee, S. M. Yoo, K. I. Choi, J. H. Song, J. H. Jang, S. R. Oh, H. W. Ryu, H. S. Lee, Y. J. Surh, Y. Y. Cho, BMC Cancer 15 (2015) 576 (https://dx.doi.org/10.1186/s12885-015-1580-7)

G. R. Pettit, Y. Meng, R. P. Gearing, D. L. Herald, R. K. Pettit, D. L. Doubek, J. C. Chapuis, L. P. Tackett, J. Nat. Prod. 67 (2004) 214 (https://dx.doi.org/10.1021/np030125s)

E. J. D. Leon, D. A. Olmedo, P. N. Solıs, M. P. Gupta, M. C. Terencio, Planta Med. 68 (2002) 1128 (https://dx.doi.org/10.1055/s-2002-36355)

Y. S. Lee, B. Y. Cha, S. S. Choi, Y. Harada, B. K. Choi, T. Yonezawa, T. Teruya, K. Nagai, J. T. Woo, BioFactors 38 (2012) 300 (https://doi.org/10.1002/biof.1022)

M. F. Serra, B. L. Diaz, E. O. Barreto, A. P. B. Pereira, M. C. R. Lima, J. M. B. Barbosa-Filho, R. S. B. Cordeiro, M. A. Martins, P. M. R. D. Silva, Planta Med. 63 (1997) 207 (https://dx.doi.org/10.1055/s-2006-957654)

Y. Zhao, F. Li, J. Yang, X. An, M. Zhou, J. Chin. Med. Mater. 28 (2005) 123 (https://www.ncbi.nlm.nih.gov/pubmed/15981888)

T. Nikaido, T. Ohmoto, T. Kinoshita, U. Sankawa, S. Nishibe, S. Hisada, Chem. Pharm. Bull. 29 (1981) 3586 (https://dx.doi.org/10.1248/cpb.29.3586)

D. X. Li, M. Liu, X. J. Zhou, China J. Chin. Mater. Med. 40 (2015) 2843 (https://www.ncbi.nlm.nih.gov/pubmed/26666037)

A. M. Rimando, F. E. Dayan, J. R. Mikell, R. M. Moraes, Nat. Toxins 7 (1999) 39 (https://dx.doi.org/10.1002/(SICI)1522-7189(199902)7:1<39::AID-NT38>3.0.CO;2-2)

P. V. Bhiravamurty, R. D. Kanakala, E. V. Rao, K. V. Sastry, Curr. Sci. 48 (1979) 949 (http://agris.fao.org/agris-search/search.do?recordID=US201302112425)

T. J. Mabry, A. Ulubelen, J. Agric. Food Chem. 28 (1980) 188 (https://dx.doi.org/10.1021/jf60228a024)

K. Akimoto, Y. Kitagawa, T. Akamatsu, N. Hirose, M. Sugano, S. Shimizu, H. Yamada, Ann. Nutr. Metab. 37 (1993) 218 (https://dx.doi.org/10.1159/000177771)

M. Tada, Y. Ono, M. Nakai, M. Harada, H. Shibata, Y. Kiso, T. Ogata, Anal. Sci. 29 (2013) 89 (https://dx.doi.org/10.2116/analsci.29.89)

C. M. Liu, G. H. Zheng, Q. L. Ming, C. Chao, J. M. Sun, J. Agric. Food Chem. 61 (2013) 1146 (https://dx.doi.org/10.1021/jf304562b)

S. Sirato-Yasumoto, M. Katsuta, Y. Okuyama, Y. Takahashi, T. Ide, J. Agric. Food Chem. 49 (2001) 2647 (https://dx.doi.org/10.1021/jf001362t)

T. Miyawaki, H. Aono, Y. Toyoda-Ono, H. Maeda, Y. Kiso, K. Moriyama, J. Nutr. Sci Vitaminol. 55 (2009) 87 (https://dx.doi.org/10.3177/jnsv.55.87)

M. Nakai, M. Harada, K. Nakahara, K. Akimoto, H. Shibata, W. Miki, Y. Kiso, J. Agric. Food Chem. 51 (2003) 1666 (https://dx.doi.org/10.1021/jf0258961)

R. C. Roark, Econ. Bot. 1 (1947) 437 (https://dx.doi.org/10.1007/BF02858908)

H. L. Haller, F. B. LaForge, W. N. Sullivan, J. Org. Chem. 7 (1942) 185 (https://dx.doi.org/10.1021/jo01196a012)

H. L. Haller, F. B. LaForge, W. N. Sullivan, J. Econ. Entomol. 35 (1942) 247 (https://dx.doi.org/10.1093/jee/35.2.247)

H. L. Haller, E. R. McGovran, L. D. Goodhue, W. N. Sullivan, J. Org. Chem. 7 (1942) 183 (https://dx.doi.org/10.1021/jo01196a011)

J. E. Casida, J. Agric. Food Chem. 18 (1970) 753 (https://dx.doi.org/10.1021/jf60171a013)

S. Shimizu, K. Akimoto, Y. Shinmen, H. Kawashima, M. Sugano, H. Yamada, Lipids 26 (1991) 512 (https://dx.doi.org/10.1007/BF02536595)

T. Phitak, P. Pothacharoen, J. Settakorn, W. Poompimol, B. Caterson, P. Kongtawelert, Phytochemistry 80 (2012) 77 (https://dx.doi.org/10.1016/j.phytochem.2012.05.016)

M. J. Kato, A. Chu, L. B. Davin, N. G. Lewis, Phytochemistry 47 (1998) 583 (https://dx.doi.org/10.1016/S0031-9422(97)00727-9)

F. Hirata, K. Fujita, Y. Ishikura, K. Hosoda, T. Ishikawa, H. Nakamura, Atherosclerosis 122 (1996) 135 (https://dx.doi.org/10.1016/0021-9150(95)05769-2)

K. Yamashita, Y. Iizuka, T. Imai, M. Namiki, Lipids 30 (1995) 1019 (https://dx.doi.org/10.1007/BF02536287)

K. Yamashita, Y. Nohara, K. Katayama, M. Namiki, J. Nutr. 122 (1992) 2440 (https://dx.doi.org/10.1093/jn/122.12.2440)

A. Kamal-Eldin, D. Pettersson, L. A. Appelqvist, Lipids 30 (1995) 499 (https://dx.doi.org/10.1007/BF02537023)

W. D. MacRae, G. H. N. Towers, J. Ethnopharmacol. 12 (1984) 75 (https://dx.doi.org/10.1016/0378-8741(84)90087-4)

J. J. Chen, Y. L. Chang, C. M. Teng, I. S. Chen, Planta Med. 66 (2000) 251 (https://dx.doi.org/10.1055/s-2000-8562)

K. H. Lee, Z. Xiao, Phytochem. Rev. 2 (2003) 341 (https://dx.doi.org/10.1023/b:phyt.0000045495.59732.58)

H. C. Castro-Faria-Neto, P. T. Bozza, H. N. Cruz, C. L. M. Silva, F. A. Violante, J. M. Barbosa-Filho, G. Thomas, M. A. Martins, E. V. Tibiriçá, Planta Med. 61 (1995) 101 (https://dx.doi.org/10.1055/s-2006-958025)

H. C. Castro-Faria-Neto, M. A. Martins, P. M. R. Silva, P. T. Bozza, H. N. Cruz, M. de Queiroz-Paulo, M. A. C. Kaplan, R. S. B. Cordeiro, J. Lipid Mediat. 7 (1993) 1 (https://www.ncbi.nlm.nih.gov/pubmed/8358020)

M. Sugano, T. Inoue, K. Koba, K. Yoshida, N. Hirose, Y. Shinmen, K. Akimoto, T. Amachi, Anticancer Res. 54 (1990) 2669 (https://dx.doi.org/10.1080/00021369.1990.10870374)

N. Hirose, F. Doi, T. Ueki, K. Akazawa, K. Chijiiwa, M. Sugano, K. Akimoto, S. Shimizu, H. Yamada, Anticancer Res. 12 (1992) 1259 (https://www.ncbi.nlm.nih.gov/pubmed/1386971)

H. Ogawa, S. Sasagawa, T. Murakami, H. Yoshizumi, Clin. Exp. Pharmacol. Physiol. 22 (1995) 310 (https://dx.doi.org/10.1111/j.1440-1681.1995.tb02932.x)

N. Hirose, T. Inoue, K. Nishihara, M. Sugano, K. Akimoto, S. Shimizu, H. Yamada, J. Lipid Res. 32 (1991) 629 (https://www.ncbi.nlm.nih.gov/pubmed/1856608)

T. Ogawa, T. Makino, N. Hirose, M. Sugano, Carcinogenesis 15 (1994) 1663 (https://dx.doi.org/10.1093/carcin/15.8.1663)

J. Y. Gu, Y. Wakizono, A. Tsujita, B. O. Lim, M. Nonaka, K. Yamada, M. Sugano, Biosci. Biotechnol. Biochem. 59 (1995) 2198 (https://dx.doi.org/10.1271/bbb.59.2198)

Y. Kiso, BioFactors 21 (2004) 191 (https://dx.doi.org/10.1002/biof.552210139)

L. Ashakumary, I. Rouyer, Y. Takahashi, T. Ide, N. Fukuda, T. Aoyama, T. Hashimoto, M. Mizugaki, M. Sugano, Metabolism 48 (1999) 1303 (https://dx.doi.org/10.1016/S0026-0495(99)90272-X)

R. Christov, V. Bankova, I. Tsvetkova, A. Kujumgiev, A. D. Tejera, Fitoterapia 70 (1999) 89 (https://dx.doi.org/10.1016/s0367-326x(98)00044-6)

E. M. Suleimenov, F. M. Smagulova, R. B. Seidakhmetova, R. M. Aksartov, V. A. Raldugin, S. M. Adekenov, Chem. Nat. Compd. 43 (2007) 232 (https://dx.doi.org/10.1007/s10600-007-0090-5)

F. Kawamura, S. Ohara, A. Nishida, Holzforschung 58 (2004) 189 (https://dx.doi.org/10.1515/HF.2004.028)

W. D. MacRae, J. B. Hudson, G. H. N. Towers, Planta Med. 55 (1989) 531 (https://dx.doi.org/10.1055/s-2006-962087)

W. D. MacRae, G. H. N. Towers, Phytochemistry 23 (1984) 1207 (https://dx.doi.org/10.1016/S0031-9422(00)80428-8)

M. A. Ouyang, Y. S. Wein, Z. K. Zhang, Y. H. Kuo, J. Agric. Food Chem. 55 (2007) 6460 (https://dx.doi.org/10.1021/jf0709808)

P. Sartorelli, C. S. Carvalho, J. Q. Reimão, H. Lorenzi, A. G. Tempone, Planta Med. 76 (2010) 1454 (https://dx.doi.org/10.1055/s-0029-1240952).