Biosynthesis of cyanogenic glucosides in Phaseolus lunatus and the evolution of oxime-based defenses
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Biosynthesis of cyanogenic glucosides in Phaseolus lunatus and the evolution of oxime-based defenses. / Lai, Daniela; Maimann, Alexandra B.; Macea, Eliana; Ocampo, Cesar H.; Cardona, Gustavo; Picmanova, Martina; Darbani, Behrooz; Olsen, Carl Erik; Debouck, Daniel; Raatz, Bodo; Moller, Birger Lindberg; Rook, Fred.
In: Plant Direct, Vol. 4, No. 8, 00244, 2020.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Biosynthesis of cyanogenic glucosides in Phaseolus lunatus and the evolution of oxime-based defenses
AU - Lai, Daniela
AU - Maimann, Alexandra B.
AU - Macea, Eliana
AU - Ocampo, Cesar H.
AU - Cardona, Gustavo
AU - Picmanova, Martina
AU - Darbani, Behrooz
AU - Olsen, Carl Erik
AU - Debouck, Daniel
AU - Raatz, Bodo
AU - Moller, Birger Lindberg
AU - Rook, Fred
PY - 2020
Y1 - 2020
N2 - Lima bean,Phaseolus lunatus, is a crop legume that produces the cyanogenic glucosides linamarin and lotaustralin. In the legumesLotus japonicusandTrifolium repens, the biosynthesis of these two alpha-hydroxynitrile glucosides involves cytochrome P450 enzymes of the CYP79 and CYP736 families and a UDP-glucosyltransferase. Here, we identify CYP79D71 as the first enzyme of the pathway inP. lunatus, producing oximes from valine and isoleucine. A second CYP79 family member, CYP79D72, was shown to catalyze the formation of leucine-derived oximes, which act as volatile defense compounds inPhaseolusspp. The organization of the biosynthetic genes for cyanogenic glucosides in a gene cluster aided their identification inL. japonicus. In the available genome sequence ofP. vulgaris, the gene orthologous toCYP79D71is adjacent to a member of theCYP83family. AlthoughP. vulgarisis not cyanogenic, it does produce oximes as volatile defense compounds. We cloned the genes encoding two CYP83s (CYP83E46 and CYP83E47) and a UDP-glucosyltransferase (UGT85K31) fromP. lunatus, and these genes combined form a complete biosynthetic pathway for linamarin and lotaustralin in Lima bean. Within the genusPhaseolus, the occurrence of linamarin and lotaustralin as functional chemical defense compounds appears restricted to species belonging to the closely related Polystachios and Lunatus groups. A preexisting ability to produce volatile oximes and nitriles likely facilitated evolution of cyanogenesis within thePhaseolusgenus.
AB - Lima bean,Phaseolus lunatus, is a crop legume that produces the cyanogenic glucosides linamarin and lotaustralin. In the legumesLotus japonicusandTrifolium repens, the biosynthesis of these two alpha-hydroxynitrile glucosides involves cytochrome P450 enzymes of the CYP79 and CYP736 families and a UDP-glucosyltransferase. Here, we identify CYP79D71 as the first enzyme of the pathway inP. lunatus, producing oximes from valine and isoleucine. A second CYP79 family member, CYP79D72, was shown to catalyze the formation of leucine-derived oximes, which act as volatile defense compounds inPhaseolusspp. The organization of the biosynthetic genes for cyanogenic glucosides in a gene cluster aided their identification inL. japonicus. In the available genome sequence ofP. vulgaris, the gene orthologous toCYP79D71is adjacent to a member of theCYP83family. AlthoughP. vulgarisis not cyanogenic, it does produce oximes as volatile defense compounds. We cloned the genes encoding two CYP83s (CYP83E46 and CYP83E47) and a UDP-glucosyltransferase (UGT85K31) fromP. lunatus, and these genes combined form a complete biosynthetic pathway for linamarin and lotaustralin in Lima bean. Within the genusPhaseolus, the occurrence of linamarin and lotaustralin as functional chemical defense compounds appears restricted to species belonging to the closely related Polystachios and Lunatus groups. A preexisting ability to produce volatile oximes and nitriles likely facilitated evolution of cyanogenesis within thePhaseolusgenus.
KW - chemical defense
KW - cyanogenic glucosides
KW - cytochrome P450
KW - Phaseolus lunatus
KW - SORGHUM-BICOLOR
KW - CYTOCHROME-P450 ENZYMES
KW - HYDROXYNITRILE GLUCOSIDES
KW - LOTUS-JAPONICUS
KW - GENE CLUSTERS
KW - EXPRESSION
KW - LINAMARIN
KW - DHURRIN
KW - LOTAUSTRALIN
KW - LEGUMINOSAE
U2 - 10.1002/pld3.244
DO - 10.1002/pld3.244
M3 - Journal article
C2 - 32775954
VL - 4
JO - Plant Direct
JF - Plant Direct
SN - 2475-4455
IS - 8
M1 - 00244
ER -
ID: 249479069