- STRESS COMPOUNDS IN THE LEAVES OF NICOTIANA UNDULATA INDUCED BY TMV INOCULATION
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In leaves of Nicotiana undulata inoculated with TVM, 19 sesquiterpenoids were detected as stress compounds.Among them, dehydrocarissone, capsidiol 3-acetate, aubergenone, 4-epi-aubergenone, trans-dihydrocarissone, 1,2-dehydro-α-cyperone and 3-epi-3-hydroxysolavetivone are novel tobacco stress compounds.Key Word Index - Nicotiana undulata; Solanaceae; tobacco; sesquiterpenoid; stress compounds.
- Uegaki, Reiko,Kubo, Susumu,Fujimori, Takane
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p. 365 - 368
(2007/10/02)
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- Stress metabolites of Solanum melongena: biosynthetic studies and isolation of auberganol and α- and β-eudesmol
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Attempts to clarify the biosynthetic origin of the eggplant stress metabolite aubergenone (1) by incorporation of label from sodium acetate were frustrated by low yields and enrichment levels.However, the presence of deuterium in the biosynthetically significant 5-position was demonstrated by 2Hmr for the closely related auberganol (5) and α- and β-eudesmol (10 and 11), suggesting that these compounds, and hence also 1, are normal eudesmanes and not the products of a possible double rearrangement.Deuterium was also incorporated into the expected positions of 9-oxonerolidol (12), 9-oxynerolidol (13), and lubimin (4).Inco rporation of label from acetate could be determined satisfactorily only for 13 and its allylic isomer 14, corresponding with expectations.This is the first report of 5 as a natural product and of 10, 11, and the 10-epimer of 4 as eggplant stress metabolites.
- Stoessl, Albert,Stothers, J. B.
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- The chemistry of thujone. VII. Thujone as a chiral synthon for the preparation of sesquiterpenes. Synthesis of β-elemol
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An efficient synthesis of β-elemol (4) from thujone (1) is described.The key intermediate 3 is readily prepared and described in previous studies within the syntheses of (+)-carissone (2).
- Kutney, James P.,Singh, Ashok K.
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p. 1111 - 1114
(2007/10/02)
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- Synthesis of Aubergenone, a Sesquiterpenoid Phytoalexin from Diseased Eggplants
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The synthesis of aubergenone, a stress metabolite isolated from diseased eggplants, from α-cyperone, which implies revision of the assigned structure to the metabolite, is described.
- Murai, Akio,Abiko, Atsushi,Ono, Mitsunori,Masamune, Tadashi
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p. 1191 - 1194
(2007/10/02)
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