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Bioscience, Biotechnology, and Biochemistry Volume 65, 2001 - Issue 2
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Original Articles

Actinidic Acid, a New Triterpene Phytoalexin from Unripe Kiwi Fruit

El Hassane LAHLOUCREST, Japan Science and Technology Corporation(JST)
,
Nobuhiro HIRAICREST, Japan Science and Technology Corporation(JST);Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University
,
Tsunashi KAMOCREST, Japan Science and Technology Corporation(JST);Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University
,
Mitsuya TSUDADivision of Environmental Science and Technology, Graduate School of Agriculture, Kyoto University
&
Hajime OHIGASHIDivision of Applied Life Sciences, Graduate School of Agriculture, Kyoto University
Pages 480-483 | Received 30 Aug 2000, Accepted 24 Oct 2000, Published online: 22 May 2014

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  • 3) Kamo, T., Kato, N., Hirai, N., Tsuda, M., Fujioka, D., and Ohigashi, H., Phenylphenalenone-type phytoalexins from unripe bungulan banana fruit. Biosci. Biotechnol. Biochem., 62, 95-101 (1998).
  • 4) Kamo, T., Kato, N., Hirai, N., Tsuda, M., Fujioka, D., and Ohigashi, H., A biosynthetic intermediate of phytoalexins in banana fruits. Phytochemistry, 49, 1617-1621 (1998).
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  • 10) Spectral data for compound 1. [α]27 D + 104° (c 0.14, methanol); EIMS (70 eV, probe) m/z (rel. int.): 486 [M]+ (8), 468 (2), 450 (5), 278 (17), 246 (63), 201 (100), 189 (39), 173 (37), 149 (32), 119 (42); HR-EIMS m/z [M]+: calcd. for C30H46O5, 486.3345; found, 486.3330; and m/z [M-240]+: calcd. for C16H22O2, 246.1620; found, 246.1636; NMR δH (500 MHz, CD3OD): 0.73 (3H, s, H-24), 0.90 (3H, s, H-26), 1.04 (3H, d, J=6.4 Hz, H-29), 1.08 (3H, s, H-25), 1.22 (3H, s, H-27), 1.37-2.42 (19H, m, H-1, 5, 6, 7, 9, 11, 15, 16, 19, 21 and 22), 2.33 (1H, d, J=11.4 Hz, H-18), 3.30 (1H, d, J=11.1 Hz, H-23), 3.40 (1H, d, J=9.6 Hz, H-3), 3.54 (1H, d, J=11.1 Hz, H-23), 3.73 (1H, ddd, J=11.3, 9.6 and 4.5 Hz, H-2), 4.64 (1H, s, H-30), 4.69 (1H, s, H-30), 5.30 (1H, t, J=3.5 Hz, H-12); NMR δC (125 MHz, CD3OD): 14.0 (C-24), 16.9 (C-29), 17.8 (C-25), 18.0 (C-26), 19.2 (C-6), 24.1 (C-27), 24.6 (C-11), 25.6 (C-16), 29.4 (C-15), 33.6 (C-7), 33.7 (C-21), 38.8 (C-22), 39.1 (C-19), 40.7 (C-8), 40.8 (C-1), 43.6 (C-14), 44.2 (C-4), 48.1 (C-10), 48.3 (C-5), 49.4 (C-9, overlapping with signals of the solvent), 49.7 (C-17), 56.9 (C-18), 66.5 (C-23), 69.8 (C-2), 78.3 (C-3), 105.0 (C-30), 126.7 (C-12), 140.0 (C-13), 155.0 (C-20), 182.1 (C-28).
  • 11) Spectral data for compound 1a. EIMS (70 eV, probe) m/z (rel. int.): 500 [M]+ (50), 482 (4), 464 (4), 260 (58), 247 (89), 201 (100), 187 (39); NMR δH (300 MHz, CDCl3): 0.75 (3H, s, H-24), 0.91 (3H, s, H-26), 0.99 (3H, d, J=5.5 Hz, H-29), 1.04 (3H, s, H-25), 1.13 (3H, s, H-27), 1.36-2.23 (19H, m, 1, 5, 6, 7, 9, 11, 15, 16, 19, 21 and 22), 2.28 (1H, br. s, H-18), 3.41 (1H, d, J=10.8 Hz, H-23), 3.48 (1H, d, J=9.4 Hz, H-3), 3.60 (3H, s, 28-O-Me), 3.70 (1H, d, J=10.8 Hz, H-23), 3.78 (1H, m, H-2), 4.64 (1H, s, H-30), 4.69 (1H, s, H-30), 5.29 (1H, t, J=3.5 Hz, H-12).
  • 12) Spectral data for compound 1b. EIMS (70 eV, probe) m/z (rel. int.): 626 [M]+ (49), 566 (18), 260 (28), 247 (100), 201 (56), 187 (31); NMR δH (300 MHz, CDCl3): 0.75 (3H, s, H-24), 0.89 (3H, s, H-26), 0.99 (3H, d, J=5.4 Hz, H-29), 1.10 (3H, s, H-25), 1.13 (3H, s, H-27), 1.38-2.31 (19H, m, 1, 5, 6, 7, 9, 11, 15, 16, 19, 21 and 22), 1.98 (3H, s, OAc), 2.02 (3H, s, OAc), 2.09 (3H, s, OAc), 2.33 (1H, br. s, H-18), 3.58 (1H, d, J=11.8 Hz, H-23), 3.60 (3H, s, 28-O-Me), 3.85 (1H, d, J=11.8 Hz, H-23), 4.64 (1H, s, H-30), 4.69 (1H, s, H-30), 5.08 (1H, d, J=10.3 Hz, H-3), 5.18 (1H, m, H-2), 5.29 (1H, t, J=3.7 Hz, H-12).
  • 13) Budzikiewicz, H., Wilson, J.M., and Djerassi, C., Mass spectrometry in structural and stereochemical problems. XXXII. Pentacyclic triterpenes. J. Am. Chem. Soc., 85, 3688-3699 (1963).
  • 14) Kojima, H., and Ogura, H., Configurational studies on hydroxy groups at C-2,3 and 23 or 24 of oleanene and ursene-type triterpenes by NMR spectroscopy. Phytochemistry, 28, 1703-1710 (1989).
  • 15) Tapondjou, A.L., Ngounou, N.F., Lontsi, D., Sondengam, B.L., Martin, M.-T., and Bodo, B., Pentacyclic triterpenes from Myrianthus liberecus. Pytochemistry, 40, 1761-1764 (1995).
  • 16) Kojima, H., and Ogura, H., Triterpenoids from Prunella vulgaris. Phytochemistry, 25, 729-733 (1986).
  • 17) Sashida, Y., Ogawa, K., Mori, N., and Yamanouchi, T., Triterpenoids from the fruit galls of Actinidia polygama. Phytochemistry, 31, 2801-2804 (1992).
  • 18) Kojima, H., Tominaga, H., Sato, S., and Ogura, H., Pentacyclic triterpenoids from Prunella vulgaris. Phytochemistry, 26, 1107-1111 (1987).
  • 19) Seto, T., Tanaka, T., Tanaka, O., and Naruhashi, N., β-Glucosyl esters of 19α-hydroxyursolic acid derivatives in leaves of Rubus species. Phytochemistry, 23, 2829-2834 (1984).
  • 20) Connolly, J.D., and Hill, R.A., “Dictionary of Terpenoids,” Vol. 2. Chapman and Hall, London (1991).
  • 21) Bailey, J.A., and Mansfield, J.W. eds., “Phytoalexins,” Blackie, London (1982).

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