Gossypol: phytoalexin of cotton

Tian, Xiu; Ruan, Ju-Xin; Huang, Jinquan; Fang, Xin; Mao, Ying‐Bo; Wang, Ling-Jian; Chen, Xiao‐Ya; Yang, Changqing

doi:10.1007/s11427-016-5003-z

Cited by 51 publications

(26 citation statements)

References 81 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Gossypol, the best ligand found so far, is a phytoalexin abundantly present in cotton, one of the main host plants of H. armigera (Rajapakse and Walter, 2007 ). Gossypol contents of 0.4–2% have been reported, depending on tissue and developmental stage (Cai et al, 2004 ; Tian et al, 2016 ).…”

Section: Resultsmentioning

confidence: 99%

Niemann-Pick C2 Proteins: A New Function for an Old Family

et al. 2018

View full text Add to dashboard Cite

Niemann-Pick proteins type C2 (NPC2) are carriers of cholesterol in vertebrates, with a single member in each species. The high sequence conservation between mammals and across vertebrates is related to their common function. In contrast, NPC2 proteins in arthropods have undergone extensive duplication and differentiation, probably under environmental pressure, and are likely to have different functions. Recent studies have suggested that in arthropods these proteins might act as carriers for semiochemicals and other hydrophobic compounds. In this study we focused on the function of a specific NPC2 gene in the moth Helicoverpa armigera (HarmNPC2-1). This protein binds several flavonoids with micromolar dissociation constants. The best ligand was gossypol, present in cotton, one of the main host plants for H. armigera. Western blot revealed the presence of HarmNPC2-1 in different parts of the body, including the antennae, proboscis, and abdomen. In the antennae, in situ hybridization experiments produced strong staining in auxiliary cells at the base of sensilla trichodea, basiconica, coeloconica, and chaetica. Immunocytochemistry confirmed the expression of the protein in sensilla chaetica. Our results support a role of semiochemical carriers for NPC2 proteins in insects and indicate such proteins as new targets for insecticide-free pest population control.

show abstract

Section: Resultsmentioning

confidence: 99%

Niemann-Pick C2 Proteins: A New Function for an Old Family

et al. 2018

View full text Add to dashboard Cite

show abstract

“…conferring atropselectivity to the oxidative coupling of hemigossypol (Effenberger et al, 2015). This reaction constitutes the final step in the biosynthesis of the sesquiterpenoid dimer gossypol, an important natural product and defense compound in cotton plants (Wagner et al, 2012;Tian et al, 2016). These findings indicate that the role of DIRs is not restricted to lignan biosynthesis but extends to entirely different biosynthetic pathways in plant secondary metabolism.…”

mentioning

confidence: 90%

Dirigent Protein Mode of Action Revealed by the Crystal Structure of AtDIR6

et al. 2016

View full text Add to dashboard Cite

Dirigent proteins impart stereoselectivity to phenoxy radical coupling reactions in plants and, thus, play an essential role in the biosynthesis of biologically active natural products. This includes the regioselective and enantioselective coupling and subsequent cyclization of two coniferyl alcohol radicals to pinoresinol as the committed step of lignan biosynthesis. The reaction is controlled by dirigent proteins, which, depending on the species and protein, direct the reaction to either (+)-or (2)-pinoresinol. We present the crystal structure of the (2)-pinoresinol forming DIRIGENT PROTEIN6 (AtDIR6) from Arabidopsis (Arabidopsis thaliana) with data to 1.4 Å resolution. The structure shows AtDIR6 as an eight-stranded antiparallel b-barrel that forms a trimer with spatially well-separated cavities for substrate binding. The binding cavities are two lobed, exhibiting two opposing pockets, each lined with a set of hydrophilic and potentially catalytic residues, including essential aspartic acids. These residues are conserved between (+) and (2)-pinoresinol-forming DIRs and required for activity. The structure supports a model in which two substrate radicals bind to each of the DIR monomers. With the aromatic rings fixed in the two pockets, the propionyl side chains face each other for radical-radical coupling, and stereoselectivity is determined by the exact positioning of the side chains. Extensive mutational analysis supports a previously unrecognized function for DIRs in catalyzing the cyclization of the bis-quinone methide reaction intermediate to yield (+)-or (2)-pinoresinol.

show abstract

“…18 Gossypol and derivatives play important roles in defense against the pests and pathogens due to their cytotoxicity. 19 Studies in mammals, including humans, have shown that the members of the CYP1, CYP2, CYP3 and CYP4 subfamilies are involved in detoxification of xenobiotic compounds such as drugs, environmental pollutants, many natural products and ethanol. 2 This current research demonstrated that these four plant allelochemicals can regulate the expression of three newly identified members of the CYP6 subfamily.…”

Section: Discussionmentioning

confidence: 99%