Literature DB >> 16739016

Effect of racemic and (+)- and (-)-gossypol on the survival and development of Helicoverpa zea larvae.

Robert D Stipanovic1, Juan D Lopez, Michael K Dowd, Lorraine S Puckhaber, Sara E Duke.   

Abstract

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.

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Year:  2006        PMID: 16739016     DOI: 10.1007/s10886-006-9052-9

Source DB:  PubMed          Journal:  J Chem Ecol        ISSN: 0098-0331            Impact factor:   2.626


  14 in total

1.  On the botanical distribution of chiral forms of gossypol.

Authors:  J W Jaroszewski; T Strøm-Hansen; S H Hansen; O Thastrup; H Kofod
Journal:  Planta Med       Date:  1992-10       Impact factor: 3.352

2.  Relative toxicity of gossypol enantiomers in broilers.

Authors:  M M Lordelo; A J Davis; M C Calhoun; M K Dowd; N M Dale
Journal:  Poult Sci       Date:  2005-09       Impact factor: 3.352

3.  Biochemical correlates of the antitumor and antimitochondrial properties of gossypol enantiomers.

Authors:  C C Benz; M A Keniry; J M Ford; A J Townsend; F W Cox; S Palayoor; S A Matlin; W N Hait; K H Cowan
Journal:  Mol Pharmacol       Date:  1990-06       Impact factor: 4.436

4.  Comparative anti-fertility effects of gossypol enantiomers in male hamsters.

Authors:  M C Lindberg; R H Naqvi; S A Matlin; R H Zhou; G Bialy; R P Blye
Journal:  Int J Androl       Date:  1987-08

5.  Stereo-specific cytotoxic effects of gossypol enantiomers and gossypolone in tumour cell lines.

Authors:  M D Shelley; L Hartley; R G Fish; P Groundwater; J J Morgan; D Mort; M Mason; A Evans
Journal:  Cancer Lett       Date:  1999-01-29       Impact factor: 8.679

6.  Cottonseed with a high (+)- to (-)-gossypol enantiomer ratio favorable to broiler production.

Authors:  C A Bailey; R D Stipanovic; M S Ziehr; A U Haq; M Sattar; L F Kubena; H L Kim; R de M Vieira
Journal:  J Agric Food Chem       Date:  2000-11       Impact factor: 5.279

7.  Inhibitory effects of gossypol on corticosteroid 11-beta-hydroxysteroid dehydrogenase from guinea pig kidney: a possible mechanism for causing hypokalemia.

Authors:  G W Sang; B Lorenzo; M M Reidenberg
Journal:  J Steroid Biochem Mol Biol       Date:  1991-08       Impact factor: 4.292

8.  Preparation of enantiomeric gossypol by crystallization.

Authors:  Michael K Dowd
Journal:  Chirality       Date:  2003-06       Impact factor: 2.437

9.  (-)-Gossypol: an active male antifertility agent.

Authors:  S A Matlin; R Zhou; G Bialy; R P Blye; R H Naqvi; M C Lindberg
Journal:  Contraception       Date:  1985-02       Impact factor: 3.375

10.  [The effects of optical isomers of gossypol on Sertoli cells in vitro].

Authors:  H Li; X He
Journal:  Zhongguo Yi Xue Ke Xue Yuan Xue Bao       Date:  1993-04
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  18 in total

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Authors:  Quan Sun; Yingfan Cai; Yongfang Xie; Jianchuan Mo; Youlu Yuan; Yuzhen Shi; Shengwei Li; Huaizhong Jiang; Zheng Pan; Yunling Gao; Min Chen; Xiaohong He
Journal:  Mol Biol Rep       Date:  2009-11-04       Impact factor: 2.316

2.  Sesquiterpene lactone stereochemistry influences herbivore resistance and plant fitness in the field.

Authors:  Jeffrey R Ahern; Kenneth D Whitney
Journal:  Ann Bot       Date:  2013-12-30       Impact factor: 4.357

3.  Interaction of Ferulic Acid with Glutathione S-Transferase and Carboxylesterase Genes in the Brown Planthopper, Nilaparvata lugens.

Authors:  Jun Yang; Xiao-Qin Sun; Shu-Ying Yan; Wen-Jun Pan; Mao-Xin Zhang; Qing-Nian Cai
Journal:  J Chem Ecol       Date:  2017-06-24       Impact factor: 2.626

4.  Synergistic interactions between Cry1Ac and natural cotton defenses limit survival of Cry1Ac-resistant Helicoverpa zea (Lepidoptera: Noctuidae) on Bt cotton.

Authors:  Konasale J Anilkumar; Sakuntala Sivasupramaniam; Graham Head; Robert Orth; Edzard Van Santen; William J Moar
Journal:  J Chem Ecol       Date:  2009-07-09       Impact factor: 2.626

5.  Cotton plants expressing CYP6AE14 double-stranded RNA show enhanced resistance to bollworms.

Authors:  Ying-Bo Mao; Xiao-Yuan Tao; Xue-Yi Xue; Ling-Jian Wang; Xiao-Ya Chen
Journal:  Transgenic Res       Date:  2010-10-17       Impact factor: 2.788

6.  Transcriptional responses underlying the hormetic and detrimental effects of the plant secondary metabolite gossypol on the generalist herbivore Helicoverpa armigera.

Authors:  Maria de la Paz Celorio-Mancera; Seung-Joon Ahn; Heiko Vogel; David G Heckel
Journal:  BMC Genomics       Date:  2011-11-23       Impact factor: 3.969

7.  Gossypol Inhibits Electron Transport and Stimulates ROS Generation in Yarrowia lipolytica Mitochondria.

Authors:  Anna Yu Arinbasarova; Alexander G Medentsev; Vladimir I Krupyanko
Journal:  Open Biochem J       Date:  2012-03-19

8.  Gene Expression Correlation Analysis Reveals MYC-NAC Regulatory Network in Cotton Pigment Gland Development.

Authors:  Hailiang Cheng; Xiaoxu Feng; Dongyun Zuo; Youping Zhang; Qiaolian Wang; Limin Lv; Chaofeng Wu; Shuyan Li; Yuanli Dai; Da Qu; Man He; Shang Liu; Guoli Song
Journal:  Int J Mol Sci       Date:  2021-05-08       Impact factor: 5.923

9.  Increased long-flight activity triggered in beet armyworm by larval feeding on diet containing Cry1Ac protoxin.

Authors:  Xing Fu Jiang; Jian Chen; Lei Zhang; Thomas W Sappington; Li Zhi Luo
Journal:  PLoS One       Date:  2013-05-13       Impact factor: 3.240

10.  Population genetic structure of the cotton bollworm Helicoverpa armigera (Hübner) (Lepidoptera: Noctuidae) in India as inferred from EPIC-PCR DNA markers.

Authors:  Gajanan Tryambak Behere; Wee Tek Tay; Derek Alan Russell; Keshav Raj Kranthi; Philip Batterham
Journal:  PLoS One       Date:  2013-01-11       Impact factor: 3.240

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