TY - JOUR
T1 - β-furfuryl-β-glucoside
T2 - An endogenous activator of higher plant UDP-glucose: (1 → 3)-β-glucan synthase
AU - Ohana, Patricia
AU - Delmer, Deborah P.
AU - Steffens, John C.
AU - Matthews, David E.
AU - Mayer, Raphael
AU - Benziman, Moshe
PY - 1991
Y1 - 1991
N2 - We have recently established the existence of endogenous activators of higher plant UDP-glucose: (1 → 3)-β-glucan synthase (Callaghan, T., Ross, P., Weinberger-Ohana, P., and Benziman, M. (1988) Plant Physiol. 86, 1099-1103). Here we report the purification and chemical analysis of the most abundant and specific compound, termed Activator I, isolated from Vigna radiata. This compound was extensively purified by a multistep procedure which yielded 0.1 mg of purified activator/g of fresh tissue. Enzyme digestion, neutral sugar analysis, GC/MS of permethylated derivatives, and NMR analysis of native Activator I indicated that the compound contains a single β-linked glucosyl residue. High resolution FAB-MS indicated an elemental composition of C11H16O7 (Mr = 260), with a calculated Mr of 98 for the aglycone. 13C, DEPT, and COSY NMR spectra showed that the aglycone molecule is an oxygen heterocycle of 5 carbons, consistent with a structure of β-furfuryl alcohol. Comparison of IR and GC/EI-MS spectra of authentic β-furfuryl alcohol with native aglycone confirmed the conclusion that Activator I is β-furfuryl-β-glucoside. Chemically synthesized β-furfuryl-β-glucoside has identical chemical properties and biological activity when compared with the purified endogenous activator (Ka = 50 μM).
AB - We have recently established the existence of endogenous activators of higher plant UDP-glucose: (1 → 3)-β-glucan synthase (Callaghan, T., Ross, P., Weinberger-Ohana, P., and Benziman, M. (1988) Plant Physiol. 86, 1099-1103). Here we report the purification and chemical analysis of the most abundant and specific compound, termed Activator I, isolated from Vigna radiata. This compound was extensively purified by a multistep procedure which yielded 0.1 mg of purified activator/g of fresh tissue. Enzyme digestion, neutral sugar analysis, GC/MS of permethylated derivatives, and NMR analysis of native Activator I indicated that the compound contains a single β-linked glucosyl residue. High resolution FAB-MS indicated an elemental composition of C11H16O7 (Mr = 260), with a calculated Mr of 98 for the aglycone. 13C, DEPT, and COSY NMR spectra showed that the aglycone molecule is an oxygen heterocycle of 5 carbons, consistent with a structure of β-furfuryl alcohol. Comparison of IR and GC/EI-MS spectra of authentic β-furfuryl alcohol with native aglycone confirmed the conclusion that Activator I is β-furfuryl-β-glucoside. Chemically synthesized β-furfuryl-β-glucoside has identical chemical properties and biological activity when compared with the purified endogenous activator (Ka = 50 μM).
UR - http://www.scopus.com/inward/record.url?scp=0025915518&partnerID=8YFLogxK
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C2 - 1830307
AN - SCOPUS:0025915518
SN - 0021-9258
VL - 266
SP - 13742
EP - 13745
JO - Journal of Biological Chemistry
JF - Journal of Biological Chemistry
IS - 21
ER -