title: Structure-Activity Relation of AMOR Sugar Molecule That Activates Pollen-Tubes for Ovular Guidance.
abstract: Successful fertilization in flowering plants depends on the precise directional growth control of pollen tube through the female pistil tissue toward the female gametophyte contained in the ovule for delivery of nonmotile sperm cells. Cys-rich peptides LUREs secreted from the synergid cells on either side of the egg cell act as ovular attractants of pollen tubes. Competency control by the pistil is crucial for the response of pollen tubes to these ovular attractants. We recently reported that ovular 4-O-methyl-glucuronosyl arabinogalactan (AMOR) induces competency of the pollen tube to respond to ovular attractant LURE peptides in Torenia fournieri. The beta isomer of the terminal disaccharide 4-O-methyl-glucuronosyl galactose was essential and sufficient for the competency induction. However, critical and noncritical structures in the disaccharide have not been dissected deeply. Herein, we report the synthesis of new AMOR analogs and the structure-activity relationships for AMOR activity in the presence of these synthesized analogs. Removal of 4-O-methyl group or -COOH from the glucuronosyl residue of the disaccharide dramatically reduces AMOR activity. The pyranose backbone of the second sugar of disaccharide is essential for the activity but not hydroxy groups. The role of beta isomer of the disaccharide 4-Me-GlcA-β(1,6)-Gal is very specific for competency control, as there was no difference in effect among the sugar analogs tested for pollen germination. This study represents the first structure-activity relationship study, to our knowledge, of a sugar molecule involved in plant reproduction, which opens a way for modification of the molecule without loss of activity.
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8601, Japan (J.J., S.S., K.I., T.H.).|Graduate School of Science, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8602, Japan (A.G.M., J.Y., K.I., T.H.); and.|JST ERATO, Higashiyama Live-Holonics Project, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8602, Japan (T.H.).
authors.forename: Jiao
authors.identifier: 0000-0003-3726-3798
authors.initials: J
authors.lastname: Jiao
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8601, Japan (J.J., S.S., K.I., T.H.).|Graduate School of Science, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8602, Japan (A.G.M., J.Y., K.I., T.H.); and.|JST ERATO, Higashiyama Live-Holonics Project, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8602, Japan (T.H.).
authors.forename: Akane G
authors.initials: AG
authors.lastname: Mizukami
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8601, Japan (J.J., S.S., K.I., T.H.).|Graduate School of Science, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8602, Japan (A.G.M., J.Y., K.I., T.H.); and.|JST ERATO, Higashiyama Live-Holonics Project, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8602, Japan (T.H.).
authors.forename: Subramanian
authors.identifier: 0000-0002-0398-2113
authors.initials: S
authors.lastname: Sankaranarayanan
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8601, Japan (J.J., S.S., K.I., T.H.).|Graduate School of Science, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8602, Japan (A.G.M., J.Y., K.I., T.H.); and.|JST ERATO, Higashiyama Live-Holonics Project, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8602, Japan (T.H.).
authors.forename: Junichiro
authors.initials: J
authors.lastname: Yamguchi
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8601, Japan (J.J., S.S., K.I., T.H.); higashi@bio.nagoya-u.ac.jp itami@chem.nagoya-u.ac.jp.|Graduate School of Science, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8602, Japan (A.G.M., J.Y., K.I., T.H.); and higashi@bio.nagoya-u.ac.jp itami@chem.nagoya-u.ac.jp.|JST ERATO, Higashiyama Live-Holonics Project, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8602, Japan (T.H.) higashi@bio.nagoya-u.ac.jp itami@chem.nagoya-u.ac.jp.
authors.forename: Kenichiro
authors.initials: K
authors.lastname: Itami
authors.affiliation: Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8601, Japan (J.J., S.S., K.I., T.H.); higashi@bio.nagoya-u.ac.jp itami@chem.nagoya-u.ac.jp.|Graduate School of Science, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8602, Japan (A.G.M., J.Y., K.I., T.H.); and higashi@bio.nagoya-u.ac.jp itami@chem.nagoya-u.ac.jp.|JST ERATO, Higashiyama Live-Holonics Project, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8602, Japan (T.H.) higashi@bio.nagoya-u.ac.jp itami@chem.nagoya-u.ac.jp.
authors.forename: Tetsuya
authors.identifier: 0000-0002-7346-360X
authors.initials: T
authors.lastname: Higashiyawma
mesh_terms: D004187:Disaccharides / Q000737:chemistry / Q000378:metabolism; D005685:Galactans / Q000737:chemistry* / Q000378:metabolism*; D018525:Germination; D006031:Glycosylation; D019686:Lamiaceae / Q000502:physiology*; D056771:Ovule / Q000502:physiology*; D053205:Pollen Tube / Q000502:physiology*; D013329:Structure-Activity Relationship
chemical_list: D004187:Disaccharides; D005685:Galactans; C074947:4-O-methyl-glucuronoarabinogalactan; C005653:arabinogalactan