Apiin

{{chembox | Name = Apiin | Reference= | ImageFile = Apiin.svg | ImageSize = 270px | ImageName = Apigenin | IUPACName = 4′,5-Dihydroxy-7-[3-C-(hydroxymethyl)-β- D -erythrofuranosyl-(1→2)-β- D -glucopyranosyloxy]flavone | SystematicName = 7-{[(2S,3R,4S,5S,6R)-2-{[(2S,3R,4R)-3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | OtherNames = Apioside Apigenin-7-apioglucoside Apigenin-7-O-apioglucoside |Section1= |Section2= | Section7= }} Apiin is a natural flavonoid, a diglycoside of the flavone apigenin found in the winter-hardy plants parsley and celery, and in banana leaf. The glycoside moiety at carbon-7 of apigenin, O-β-D-apiofuranosyl(→)2-β-D-glucosyl, is carried by several other flavones in parsley plant and seed. The sugar apiose possibly play a role in winter hardiness of celery, duckweed and parsley.

{{chembox | Name = Apiin | Reference= | ImageFile = Apiin.svg | ImageSize = 270px | ImageName = Apigenin | IUPACName = 4′,5-Dihydroxy-7-[3-C-(hydroxymethyl)-β- D -erythrofuranosyl-(1→2)-β- D -glucopyranosyloxy]flavone | SystematicName = 7-{[(2S,3R,4S,5S,6R)-2-{[(2S,3R,4R)-3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | OtherNames = Apioside Apigenin-7-apioglucoside Apigenin-7-O-apioglucoside |Section1= |Section2= | Section7= }} Apiin is a natural flavonoid, a diglycoside of the flavone apigenin found in the winter-hardy plants parsley and celery, and in banana leaf. The glycoside moiety at carbon-7 of apigenin, O-β-D-apiofuranosyl(→)2-β-D-glucosyl, is carried by several other flavones in parsley plant and seed. The sugar apiose possibly play a role in winter hardiness of celery, duckweed and parsley. ==Biosynthesis== Apiin is a diglycoside of the flavone, apigenin. Its biosynthesis in plants involves a sequence of enzymes, with chalcone synthase being the one that forms the ring system of the natural product naringenin. Naringenin is then oxidised to apigenin: Next, the enzyme flavone 7-O-beta-glucosyltransferase transfers a glucose sugar fragment from UDP-glucose, giving apigetrin, with uridine diphosphate (UDP) as byproduct: Finally, apigetrin is converted to apiin when a second apiose sugar is added by the enzyme flavone apiosyltransferase:

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