Biovalorization of Friedelane Triterpenes Derived from Cork Processing Industry Byproducts
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- 作者：Cristina Moiteiro ; Maria Joã ; o Marcelo Curto ; Nagla Mohamed ; Marí ; a Bailé ; n ; Rafael Martí ; nez-Dí ; az ; and Azucena Gonzá ; lez-Coloma
- 刊名：Journal of Agricultural and Food Chemistry
- 出版年：2006
- 出版时间：May 17, 2006
- 年：2006
- 卷：54
- 期：10
- 页码：3566 - 3571
- 全文大小：80K
- 年卷期：v.54,no.10(May 17, 2006)
- ISSN：1520-5118
文摘
Here, we describe the synthesis, bioactivity screening, and structure-activity relationships of varioussynthetic triterpenoids prepared from the cork processing byproducts friedelin (1) and 3-hydroxyfriedel-3-en-2-one (2) via oxidative procedures. The synthesis of compounds 2
-trimethylsiloxyfriedelan-3-one (17), friedelin-2,3-lactone (18), friedelin-3-oxime (19), and friedelin-3,4-lactam (20) is alsodescribed. We have studied the insecticidal and phytotoxic potential of these compounds, theirselective cytotoxic effects on insect and mammalian cells, and their antiparasitic effects. Structuralmodifications of the A-ring of friedelin (1) improved its insecticidal activity with derivatives 5, 2,3-secofriedelan-2-al-3-oic acid (6), its acetylated derivative 6a, 3
- and 3-hydroxyfriedelane (9 and10), 3-hydroxyfriedel-2-one (11), 4-hydroxyfriedel-3-one (16), the acetylated 10a, 3,4-secofriedelan-4-oxo-3-oic-acid (14), lactone 18, and the oxime 19 being stronger insecticides than the parentcompound. Methyl-3-nor-2,4-secofriedelan-4-oxo-2-oic acid (12) and its acetylated derivative 12a alsoshowed insecticidal activity in contrast to their inactive parent compound 2. The postingestive effectsand cytotoxicity of these compounds suggest a multifaceted insecticidal mode of action. Thesestructural modifications did not result in better phytotoxic agents than the parent compounds exceptfor lactam 20 and yielded several moderately active antiparasite derivatives (seco acids 6, 12, 14,and 4 -hydroxyfriedel-3-one 16) with cytotoxic effects on mammalian cells.Keywords: Quercus suber; cork smoker wash solids; triterpene friedelanes; Spodoptera littoralis;Lactuca sativa; Trypanosoma cruzi; Leishmania infantum; antifeedant; phytotoxic; antiparasitic
-trimethylsiloxyfriedelan-3-one (17), friedelin-2,3-lactone (18), friedelin-3-oxime (19), and friedelin-3,4-lactam (20) is alsodescribed. We have studied the insecticidal and phytotoxic potential of these compounds, theirselective cytotoxic effects on insect and mammalian cells, and their antiparasitic effects. Structuralmodifications of the A-ring of friedelin (1) improved its insecticidal activity with derivatives 5, 2,3-secofriedelan-2-al-3-oic acid (6), its acetylated derivative 6a, 3- and 3-hydroxyfriedelane (9 and10), 3-hydroxyfriedel-2-one (11), 4-hydroxyfriedel-3-one (16), the acetylated 10a, 3,4-secofriedelan-4-oxo-3-oic-acid (14), lactone 18, and the oxime 19 being stronger insecticides than the parentcompound. Methyl-3-nor-2,4-secofriedelan-4-oxo-2-oic acid (12) and its acetylated derivative 12a alsoshowed insecticidal activity in contrast to their inactive parent compound 2. The postingestive effectsand cytotoxicity of these compounds suggest a multifaceted insecticidal mode of action. Thesestructural modifications did not result in better phytotoxic agents than the parent compounds exceptfor lactam 20 and yielded several moderately active antiparasite derivatives (seco acids 6, 12, 14,and 4 -hydroxyfriedel-3-one 16) with cytotoxic effects on mammalian cells.Keywords: Quercus suber; cork smoker wash solids; triterpene friedelanes; Spodoptera littoralis;Lactuca sativa; Trypanosoma cruzi; Leishmania infantum; antifeedant; phytotoxic; antiparasitic