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Agricultural and Biological Chemistry Volume 52, 1988 - Issue 12
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Organic Chemistry

Structure of a New Opine, Mikimopine, in Hairy Root Induced by Agrobacterium rhizogenes

Akira IsogaiDepartment of Agricultural Chemistry, The University of Tokyo, Bunkyo-ku, Tokyo113, Japan
,
Naoyuki FukuchiDepartment of Agricultural Chemistry, The University of Tokyo, Bunkyo-ku, Tokyo113, Japan
,
Miki HayashiGene Experimental Center, University of Tsukuba, Ibaraki305, Japan
,
Hiroshi KamadaGene Experimental Center, University of Tsukuba, Ibaraki305, Japan
,
Hiroshi haradaGene Experimental Center, University of Tsukuba, Ibaraki305, Japan
&
Akinori SuzukiDepartment of Agricultural Chemistry, The University of Tokyo, Bunkyo-ku, Tokyo113, Japan
Pages 3235-3237 | Received 06 Sep 1988, Published online: 09 Sep 2014

References and Notes

  • J. B. Ellis and P. J. Murphy, Mol Gen. Gent., 181, 36 (1981).
  • A. Petit, C. David, G. A. Dahl, J. G. Ellis, P. Guyon, F. Casse-Delbart and J. Tempé, Mol. Gen. Gent., 190, 204 (1983).
  • H. Kamada et al., in preparation.
  • A. Petit, A. Berkaloff and J. Tempé, Mol. Gen. Genet., 202, 388 (1986).
  • A. Bax and M. F. Summers, J. Am. Chem. Soc., 108, 2093 (1986).
  • 3. FABMS: m/z 294; δH (ppm in D2O): 2.37 (1H, ddd, J=10, 12, 13 Hz), 2.65 (1H, dd, J=10, 17 Hz), 2.84 (1H, dd, J=9, 13Hz), 2.96 (1H, ddd, J=9, 12, 17Hz), 3.17 (1H, dd, J=8, 18Hz), 3.32 (1H, dd, J=1, 18 Hz), 3.70 (3H, s), 3.86 (3H, s), 5.50 (1H, dd, J=1, 8Hz) and 8.77 (1H, s).
  • K. M. Smith, “Comprehensive Organic Chemistry,” Vol. 4, ed. by D. Barton and W. D. Ollis, Pergamon Press, Oxford, 1979, p. 374.
  • A. Pictet and T. Spengler, Ber, 44, 2030 (1911).
  • 4. δH (ppm in D2O): 1.9-2.6 (4H, m), 2.79 (1H, dd, J=12, 16Hz), 3.16 (1H, dd, J=6, 16Hz), 3.96 (1H, dd, J=6, 12Hz), 7.80 (1H, s); [α]D: -41° (c = 2.92, H2O).
  • 5. δH (ppm in D2O): 2.2-2.8 (4H, m), 2.91 (1H, dd, J=6, 16Hz), 3.13 (1H, dd, J=10, 16Hz), 4.42 (1H, dd, J =6, 10 Hz), 8.65 (1H, s).
  • E. Davioud, A. Pettit, M. E. Tate, M. H. Ryder and J. Tempé, Phytochemistry, 27, 2429 (1988).
  • According to a personal communication from J. Tempé, cucumopine was proved to be an epimer of mikimopine and to correspond to 4 just before submitting of this paper. We thank him for presenting these physicochemical data before publication.

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