SYNTHESIS AND EVALUATION OF THE PHYTOTOXIC ACTIVITY OF α-SANTONIN DERIVATIVES

被引：18

作者：

Alvarenga, Elson S. ^{[1
]}

Barbosa, Luiz C. A. ^{[1
]}

Saliba, William A. ^{[1
]}

Arantes, Francisco F. P. ^{[1
]}

Demuner, Antonio J. ^{[1
]}

Silva, Antonio A. ^{[2
]}

机构：

[1] Univ Fed Vicosa, Dept Quim, BR-36570000 Vicosa, MG, Brazil

[2] Univ Fed Vicosa, Dept Fitotecnia, BR-36570000 Vicosa, MG, Brazil

来源：

QUIMICA NOVA | 2009年 / 32卷 / 02期

关键词：

alpha-santonin; photochemistry; herbicide; GROWTH REGULATORY ACTIVITY; SESQUITERPENE LACTONES; PHOTOCHEMICAL TRANSFORMATIONS; GLAUCOLIDE-B; ALLELOCHEMICALS; LUMISANTONIN; ACID; ANALOGS;

D O I：

10.1590/S0100-40422009000200025

中图分类号：

O6 [化学];

学科分类号：

070301 [无机化学];

摘要：

Mixtures of alpha-Santonin and various solvents were irradiated by either high or low pressure mercury lamps. The photochemical reactions afforded lumisantonin (11) (76% in acetonitrile), (3S,3aS,9bS)-3,6,6-trimethyl-3,3a,4,5-tetrahydronafto[1,2-b]furan-2,7(6H,9bH)dione (12) (100% in acetonitrile), 10 alpha-acetoxy-3-oxo-1,7 alpha H, 6,11 beta H-guaia-4-en-6,12-olide (8) (26% in acetic acid), 10 alpha-hydroxy-3-oxo-1,7 alpha H,6,11 beta H-guaia-4-en-6,12-olide (10) (32%) and (E)-3-((3S,3aS,7aS)-3-methyl-2-oxo-6-(propan-2-ylidene)hexahydrobenzofuran-7-(7aH)-ylidene) propanoic acid (9) (44%) (in water/acetic acid 1: 1, v/v). Lactone 12 was also prepared by irradiation of lumisantonin in diethyl ether. Lactones 8 and 10 were converted, respectively, into the 10 alpha-acetoxy-3 beta-hydroxy-1,7 alpha H, 6,11 beta H-guaia-4-en-6,12-olide (13) (87%) and 3 beta,10 alpha-dihydroxy-1,7 alpha H, 6,11 beta H-guaia-4-en-6,12-olide (14) (75%) by sodium borohydride reduction. The effects of the compounds on the development of radicle of Sorghum bicolor and Cucumis sativus were evaluated.

引用

页码：401 / 406

页数：6

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