Stipanovic Robert D, Lopez Juan D, Dowd Michael K, Puckhaber Lorraine S, Duke Sara E
USDA-ARS, Southern Plains Agricultural Research Center, College Station, TX, USA.
J Chem Ecol. 2006 May;32(5):959-68. doi: 10.1007/s10886-006-9052-9. Epub 2006 May 19.
Gossypol is a sesquiterpene that occurs naturally in seed and other parts of the cotton plant. Because of restricted rotation around the binaphthyl bond, it occurs naturally as enantiomeric mixtures with (+)-gossypol to (-)-gossypol ratios that vary between 97:3 and 31:69. Commercial cotton varieties (Gossypium hirsutum) normally exhibit an approximate 3:2 ratio. (+)-Gossypol is significantly less toxic than (-)-gossypol to nonruminant animals; thus, cottonseed containing high levels of (+)-gossypol might be safely fed to nonruminants. Gossypol, however, is an important component in the cotton plant's defense against insect herbivores, but it is not known how cotton plants that exhibit high levels of (+)-gossypol in the foliage might be affected by insect herbivory. To address this question, 1-d-old Helicoverpa zea larvae were fed diets with 0.16, 0.20, and 0.24% racemic, (+)-, and (-)-gossypol. Larval pupal weights, days-to-pupation, and survival were adversely affected by all gossypol diets compared with the control diet. Statistical differences were determined by comparing the compounds among themselves at the three levels and between the three compounds at the same level. When the compounds were compared among themselves, no large differences were observed in pupal weights or in days-to-pupation among any of the diets. Among the three compounds, at the 0.16% level, the diet containing racemic gossypol was the most effective at reducing survival. At the 0.20 and 0.24% levels of racemic (+)- and (-)-gossypol, survival was not statistically different. The overall results indicate that (+)-gossypol is as inhibitory to H. zea larvae as racemic or (-)-gossypol, and thus, cotton plants containing predominantly the (+)-enantiomer in foliage may maintain significant defense against insect herbivory.
棉酚是一种倍半萜烯,天然存在于棉花植株的种子及其他部位。由于联萘键周围的旋转受限,它以对映体混合物的形式天然存在,(+)-棉酚与(-)-棉酚的比例在97:3至31:69之间变化。商业棉花品种(陆地棉)通常呈现约3:2的比例。(+)-棉酚对非反刍动物的毒性明显低于(-)-棉酚;因此,含有高水平(+)-棉酚的棉籽或许可以安全地喂给非反刍动物。然而,棉酚是棉花植株抵御食草昆虫的重要成分,但尚不清楚叶片中含有高水平(+)-棉酚的棉花植株会如何受到食草昆虫的影响。为解决这个问题,给1日龄的棉铃虫幼虫喂食含有0.16%、0.20%和0.24%外消旋、(+)-和(-)-棉酚的饲料。与对照饲料相比,所有含棉酚的饲料对幼虫化蛹重量、化蛹天数和存活率均产生了不利影响。通过比较三种水平下各化合物之间以及同一水平下三种化合物之间的差异来确定统计学差异。当各化合物相互比较时,在任何一种饲料的化蛹重量或化蛹天数方面均未观察到显著差异。在三种化合物中,在0.16%的水平下,含有外消旋棉酚的饲料在降低存活率方面最为有效。在外消旋(+)-和(-)-棉酚含量为0.20%和0.24%的水平下,则存活率在统计学上无差异。总体结果表明,(+)-棉酚对棉铃虫幼虫的抑制作用与外消旋或(-)-棉酚相同,因此,叶片中主要含有(+)-对映体的棉花植株可能对食草昆虫保持显著的防御能力。