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Chemical Constituents from the Seeds of Amorpha fruticosa and Their Chemotaxonomic Significance

DOI: 10.4236/oalib.1102740, PP. 1-7

Subject Areas: Plant Science

Keywords: Amorpha fruticosa, Rotenoid, Isoflavone, Chemotaxonomy

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Abstract

Seventeen compounds, including six rotenoids (1-6), seven isoflavones (7-13), one stilbene (14) and three benzoic acid derivatives (15-17) were isolated from the seeds of Amorpha fruticosa. Their structures were elucidated by spectroscopic methods and by comparison of their reported spectral data. Among them, compound 4 was firstly purified as a natural product, compounds 5, 8 - 12 and 15 - 17 were isolated from the genus Amorpha for the first time, and compound 17 was obtained from the Fabaceae family initially. The presence of these compounds suggests that genus Amorpha and Dalbergia may have very close chemotaxonomic relationship, and shows the relationship between this plant and other species from the Fabaceae family.

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Wu, X. , Liao, H. , Wu, K. and Cui, L. (2016). Chemical Constituents from the Seeds of Amorpha fruticosa and Their Chemotaxonomic Significance. Open Access Library Journal, 3, e2740. doi: http://dx.doi.org/10.4236/oalib.1102740.

References

[1]  Straub, S.C.K. and Doyle, J.J. (2014) Molecular Phylogenetics of Amorpha (Fabaceae): An Evaluation of Monophyly, Species Relationships, and Polyploid Origins. Molecular Phylogenetics Evolution, 76, 49-66.
http://dx.doi.org/10.1016/j.ympev.2014.02.025
[2]  Chinese P.U. (1997) A Dictionary of Chinese Materal Medica. 3th Edition, Chinese Science and Technology Press of Medicine, Beijing.
[3]  Zhao, H.K. (1982) A Dictionary of the Families and Genera of Chinese Seed Plants. 2th Edition, Science Publishing House, Beijing.
[4]  Mitscher, L.A., Park, Y.H., Alshamma, A., Hudson, P.B. and Haas, T. (1981) Amorfrutin-A and Amorfrutin-B, Bibenzyl Anti-microbial Agents from Amorpha fruticosa. Phytochemistry, 20, 781-785.
http://dx.doi.org/10.1016/0031-9422(81)85174-6
[5]  Somleva, T. and Ognyanov, I. (1985) New Rotenoidsin Amorpha fruticosa Fruits. Planta Medica, 51, 219-221.
http://dx.doi.org/10.1055/s-2007-969462
[6]  Rozsa, Z., Hohmann, J., Szendrei, K., Reisch, J. and Mester, I. (1982) Amoritin, Amorisin, and Amorilin-3 New Prenylated Flavanones from Amorpha fruticosa L. Heterocycles, 19, 1793-1796.
http://dx.doi.org/10.3987/R-1982-10-1793
[7]  Lee, H.J., Lee, O.K., Kwon, Y.H., Choi, D.H., Kang, H.Y., Lee, H.Y., Paik, K.H. and Lee, H.J. (2006) Isoflavone Glycosides from the Bark of Amorpha fruticosa. Chemistry of Natural Compounds, 42, 415-418.
http://dx.doi.org/10.1007/s10600-006-0169-4
[8]  Kemal, M., Khalil, S.K.W., Rao, N.G.S. and Woolsey, N.F. (1979) Isolation and Identification of a Cannabinoid-Like Compound from Amorpha Species. Journal of Natural Products, 42, 463-468.
http://dx.doi.org/10.1021/np50005a004
[9]  Kasymov, A.U., Kondrate.Es, Rashkes, Y.V. and Abubakir, N.K. (1970) Amorphigenol-Beta-D-Glycopyransid from Amorpha. Khimiya Prirodnykh Soedinenii, 6, 192-195.
[10]  Mitscher, L.A., Gollapudi, S.R., Drake, S. and Oburn, D.S. (1985) Amorphastilbol, an Antimicrobial Agent from Amorpha nana. Phytochemistry, 24, 1481-1483.
http://dx.doi.org/10.1016/S0031-9422(00)81048-1
[11]  Wu, X., Liao, H.B., Li, G.Q., Liu, Y., Cui, L., Wu, K.F., Zhu, X.H. and Zeng, X.B. (2015) Cytotoxic Rotenoid Glycosides from the Seeds of Amorpha fruticosa. Fitoterapia, 100, 75-80.
http://dx.doi.org/10.1016/j.fitote.2014.11.015
[12]  Konoshima, T., Terada, H., Kokumai, M., Kozuka, M., Tokuda, H., Estes, J.R., Li, L.P., Wang, H.K. and Lee, K.H. (1993) Studies on Inhibitors of Skin Tumor Promotion. 12. Rotenoids from Amorpha fruticosa. Journal of Natural Products, 56, 843-848.
http://dx.doi.org/10.1021/np50096a006
[13]  Kalra, A.J., Krishnamurti, M. and Nath, M. (1977) Chemical Investigation of Indian Yam Beans (Pachyrrhizus- Erosus)-Isolation and Structures of 2 New Rotenoids and a New Isoflavanone, Erosenone. Indian Journal of Chemistry Section B Organic Chemistry Including Medicinal Chemistry, 15, 1084-1086.
[14]  Shibata, H. and Shimizu, S. (1978) Amorphaquinone, a New Isoflavanquinone from Amorpha fruticosa L. Heterocycles, 10, 85-86.
http://dx.doi.org/10.3987/S-1978-01-0085
[15]  Choi, C.W., Choi, Y.H., Cha, M.-R., Yoo, D.S., Kim, Y.S., Yon, G.H., Hong, K.S., Kim, Y.H. and Ryu, S.Y. (2010) Yeast Alpha-Glucosidase Inhibition by Isoflavones from Plants of Leguminosae as an in Vitro Alternative to Acarbose. Journal of Agricultural Food Chemistry, 58, 9988-9993.
http://dx.doi.org/10.1021/jf101926j
[16]  Biegasiewicz, K.F., St Denis, J.D., Carroll, V.M. and Priefer, R. (2010) An Efficient Synthesis of Daidzein, Dimethyldaidzein, and Isoformononetin. Tetrahedron Letters, 51, 4408-4410.
http://dx.doi.org/10.1016/j.tetlet.2010.06.078
[17]  Lee, C., Lee, J.W., Jin, Q., Jang, D.S., Lee, S.J., Lee, D., Hong, J.T., Kim, Y., Lee, M.K. and Hwang, B.Y. (2013) Inhibitory Constituents of the Heartwood of Dalbergia odorifera on Nitric Oxide Production in RAW 264.7 Macrophages. Bioorganic Medicinal Chemistry Letters, 23, 4263-4266.
http://dx.doi.org/10.1016/j.bmcl.2013.04.032
[18]  Nagarajan, N.S., Sethuraman, M.G., Manoj, C.N. and Rao, R.P. (2006) Dalsympathetin—A New Isoflavone Gentiobioside from Dalbergia sympathetica (Dennst.). Natural Product Research, 20, 195-200.
http://dx.doi.org/10.1080/14786410500046513
[19]  Dixit, P., Chillara, R., Khedgikar, V., Gautam, J., Kushwaha, P., Kumar, A., Singh, D., Trivedi, R. and Maurya, R. (2012) Constituents of Dalbergia sissoo Roxb. Leaves with Osteogenic Activity. Bioorganic Medicinal Chemistry Letters, 22, 890-897.
http://dx.doi.org/10.1016/j.bmcl.2011.12.036
[20]  Abe, F., Donnelly, D.M.X., Moretti, C. and Polonsky, J. (1985) Isoflavanoid Constituents from Dalbergia monetaria. Phytochemistry, 24, 1071-1076.
http://dx.doi.org/10.1016/S0031-9422(00)83185-4
[21]  Innocent, E. (2012) A New Isoflavone glycoside from Dalbergia vacciniifolia (Fabaceae). Scientia Pharmaceutica, 80, 469-474.
http://dx.doi.org/10.3797/scipharm.1112-23
[22]  De Groot, J.C., Weidner, C., Krausze, J., Kawamoto, K., Schroeder, F.C., Sauer, S. and Buessow, K. (2013) Structural Characterization of Amorfrutins Bound to the Peroxisome Proliferator-Activated Receptor Gamma. Journal of Medicine Chemistry, 56, 1535-1543.
http://dx.doi.org/10.1021/jm3013272
[23]  Ma, J., Yang, H., Basile, M.J. and Kennelly, E.J. (2004) Analysis of Polyphenolic Antioxidants from the Fruits of Three Pouteria Species by Selected Ion Monitoring Liquid Chromatography-Mass Spectrometry. Journal of Agricultural Food Chemistry, 52, 5873-5878.
http://dx.doi.org/10.1021/jf049950k
[24]  Chaubal, R., Mujumdar, A.M., Misar, A. and Deshpande, N.R. (2005) Isolation of Phenolic Compounds from Acacia Nilotica with Topical Antiinflammatory Activity. Asian Journal of Chemistry, 17, 1595-1599.
[25]  Liu, S.P., Tian, W., Xue, Y.H., Zeng, W., Kong, Y.S. and Qiu, M. (2013) Method for Extracting Antioxidant from Myricaria Laxiflora, and Applications Thereof. Faming Zhuanli Shenqing, Patent No. CN 103301102 A 20130918.
[26]  Crombie, L., Dewick, P.M. and Whiting, D.A. (1973) Biosynthesis of Rotenoids-Chalcone, Isoflavone, and Rotenoid Stages in Formation of Amorphigenin by Amorpha fruticosa Seedlings. Journal of the Chemical Society Perkin Transactions, 1, 1285-1294.
http://dx.doi.org/10.1039/p19730001285
[27]  Van Heerden, F.R., Brandt, E.V. and Roux, D.G. (1980) Synthesis of the Pyranoisoflavonoid, Heminitidulan-Isofla- vanoidand Rotenoid Glycosides from the Bark of Dalbergia nitidula Welw Ex Bak. Journal of the Chemical Society Perkin Transactions, 1, 2463-2469.
http://dx.doi.org/10.1039/p19800002463
[28]  Parthasa, M.R., Seshadri, T.R. and Varma, R.S. (1974) Minor Isoflavonoid Glycosides of Stem Bark of Dalbergia paniculata Isolation of a New C-Glycoside. Current Science (India), 43, 74-75.
[29]  De Eknamkul, W., Umehara, K., Monthakantirat, O., Toth, R., Frecer, V., Knapic, L., Braiuca, P., Noguchi, H. andMiertus, S. (2011) QSAR Study of Natural Estrogen-Like Isoflavonoids and Diphenolics from Thai Medicinal Plants. Journal of Molecular Graphics Modelling, 29, 784-794.
http://dx.doi.org/10.1016/j.jmgm.2011.01.001
[30]  Khan, I.A., Avery, M.A., Burandt, C.L., Goins, D.K., Mikell, J.R., Nash, T.E., Azadegan, A. and Walker, L.A. (2000) Antigiardial Activity of Isoflavones from Dalbergia frutescens Bark. Journal of Natural Products, 63, 1414-1416.
http://dx.doi.org/10.1021/np000010d
[31]  Deabreumatos, F.J., Gottlieb, O.R. and Souzaandrade, C.H. (1975) Flavonoids from Dalbergia ecastophyllum. Phytochemistry, 14, 825-826.
http://dx.doi.org/10.1016/0031-9422(75)83053-6
[32]  Donnelly, D.M., Thompson, J.C., Whalley, W.B. and Ahmad, S. (1973) Dalbergia Species Part 9. Phytochemical Examination of Dalbergia stevensonii Stand. Journal of the Chemical Society Perkin Transactions, 1, 1737-1745.
http://dx.doi.org/10.1039/p19730001737
[33]  De Abreu, M., Gottlieb, O.R., Ollis, W.D. and Souza Andrade, C.H. (1970) The Chemistry of Brazilian Leguminosae-D Part 24 the Flavanoids of Dalbergia ecastophylla-D. Boletim Do INPA Pesquisas Florestais, 1-5.
[34]  Liu, R.X., Ye, M., Guo, H.Z., Bi, K.S. and Guo, D.A. (2005) Liquid Chromatography/Electrospray Ionization Mass Spectrometry for the Characterization of Twenty-Three Flavonoids in the Extract of Dalbergia odorifera. Rapid Communicationsin Mass Spectrometry, 19, 1557-1565.
http://dx.doi.org/10.1002/rcm.1936
[35]  Sarg, T., Ateya, A.M., Abdel-Ghani, A., Badr, W. and Shams, G. (1999) Phytochemical and Pharmacological Studies of Dalbergia sissoo Growing in Egypt. Pharmaceutical Biology, 37, 54-62.
http://dx.doi.org/10.1076/phbi.37.1.54.6310
[36]  Narayanan, V. and Nagarajan, N.S. (1988) Isoflavone Galactosides from Dalbergia spinosa. Phytochemistry, 27, 2364- 2365.
http://dx.doi.org/10.1016/0031-9422(88)80167-5
[37]  Umehara, K., Nemoto, K., Matsushita, A., Terada, E., Monthakantirat, O., De-Eknamkul, W., Miyase, T., Warashina, T., Degawa, M. and Noguchi, H. (2009) Flavonoids from the Heartwood of the Thai Medicinal Plant Dalbergia parviflora and Their Effects on Estrogenic-Responsive Human Breast Cancer Cells. Journal of Natural Products, 72, 2163-2168.
http://dx.doi.org/10.1021/np900676y
[38]  Ha, H.G., Kim, J.S., Kim, J.S., Lee, J.H. and Song, G.Y. (2002) Repub Korean Kongkae Taeho Kongbo. KR 2002091404 A 20021206.
[39]  Chin, Y.W., Mdee, L.K., Mbwambo, Z.H., Mi, Q., Chai, H.B., Cragg, G.M., Swanson, S.M. and Kinghorn, A.D. (2006) Prenylated Flavonoids from the Root Bark of Berchemia Discolor, a Tanzanian Medicinal Plant. Journal of Natural Products, 69, 1649-1652.
http://dx.doi.org/10.1021/np060418w
[40]  Latorre, A.O., Borghi, G.A., Lopes, P.L., Higa, K.C., Lopes, L.M.X., Maiorka, P.C., Gorniak, S.L. and Haraguchi, M. (2011) First Report on Rotenoids as Neurotoxic Principles of Seeds from Aeschynomene indica (Leguminosae). Journal Animal Veterinary Advances, 10, 26-29.
http://dx.doi.org/10.3923/javaa.2011.291.294
[41]  Dagne, E., Yenesew, A. and Waterman, P.G. (1989) Flavonoids and Isoflavonoids from Tephrosia fulvinervis and Tephrosia pentaphylla. Phytochemistry, 28, 3207-3210.
http://dx.doi.org/10.1016/0031-9422(89)80308-5
[42]  Jeon, K.S., Na, H.J., Kim, Y.M. and Kwon, H.J. (2005) Antiangiogenic Activity of 4-0-Methylgallic Acid from Canavalia Gladiata, a Dietary Legume. Biochemical Biophysical Research Communication, 330, 1268-1274.
http://dx.doi.org/10.1016/j.bbrc.2005.03.109

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