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.
Cite this paper
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.
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
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
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
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
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.
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
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
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
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
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
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
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
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
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.
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.
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
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
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.
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
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
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.
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
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
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
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
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