Acetylzeorin

Acetylzeorin

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Acetylzeorin
Category Others
Catalog number BBF-05344
CAS
Molecular Weight 486.77
Molecular Formula C32H54O3

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Specification

Synonyms 6α-Acetoxyhopane-22-ol; Lesdainin
IUPAC Name (3S,5aR,5bR,7R,11aR,13bS)-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethylicosahydro-1H-cyclopenta[a]chrysen-7-yl acetate

Properties

Appearance Needles
Melting Point 221-226°C
Solubility Soluble in Acetone

Reference Reading

1. Cytokinin metabolism in Narcissus bulbs: chilling promotes acetylation of zeatin riboside
David S Letham, Noel G Smith, David A Willcocks Funct Plant Biol. 2003 Jul;30(5):525-532. doi: 10.1071/FP02097.
The levels of the cytokinins zeatin, dihydrozeatin and N6-(isopent-2-enyl)adenine and the corresponding 9-ribosides were determined in whole Narcissus pseudonarcissus L. bulbs after onset of summer dormancy, and after storage of the dormant bulbs at 4 or 15°C under moist conditions. The cytokinin level was increased at both temperatures; the dominant cytokinin at 15°C was zeatin riboside but at 4°C the free base, zeatin, was the principal cytokinin. The metabolism of 3H-labelled zeatin, zeatin riboside and 6-benzylaminopurine was studied in scales and base plates excised from bulbs previously held at 4 or 15°C. The chilling treatment promoted conversion of [3H]zeatin riboside to O-acetylzeatin riboside (an unusual cytokinin metabolite) in the excised base plate and inhibited 9-riboside formation from 6-benzylaminopurine. Chilling also promoted formation of O-acetylzeatin riboside from [3H]zeatin in excised scale tissue. Endogenous O-acetylzeatin and O-acetylzeatin riboside were concentrated in the base plate. Relative to zeatin riboside, O-acetylzeatin riboside was degraded to adenosine and related compounds less rapidly in the leaf cluster. Since acetylation of the zeatin side chain enhances activity in cytokinin bioassays, O-acetylzeatin riboside may play a role in leaf development following chilling of Narcissus bulbs.
2. Movement to bark and metabolism of xylem cytokinins in stems of Lupinus angustifolius
Ren Zhang, David S Letham, David A Willcocks Phytochemistry. 2002 Jul;60(5):483-8. doi: 10.1016/s0031-9422(02)00085-7.
Following uptake of [(3)H]zeatin riboside and [(3)H]dihydrozeatin riboside by girdled lupin (Lupinus angustifolius L.) stems via the transpiration stream, rapid lateral movement of the radioactivity from xylem to bark was observed. Short-term studies with intact stems, and other studies with excised stem tissues, revealed that the ribosides and/or the corresponding nucleotides were the cytokinin forms which actually moved into the bark tissues. Relative to cytokinin metabolism in xylem plus pith, metabolism in bark was both more rapid and more complex. Riboside cleavage and formation of the O-acetylzeatin and O-acetyldihydrozeatin ribosides and nucleotides were almost completely confined to bark tissues. Exogenous (3)H-labelled O-acetylzeatin riboside was converted to zeatin riboside in bark tissue, but the presence of the acetyl group suppressed degradation to adenine metabolites. The sequestration and modification of xylem cytokinins by stem tissues probably contributes significantly to the cytokinin status of the shoot. New cytokinins identified by mass spectrometry in lupin were: O-acetyldihydrozeatin 9-riboside, a metabolite of exogenous dihydrozeatin riboside in stem bark; O-methylzeatin nucleotide and O-methyldihydrozeatin 9-riboside, metabolites of endogenous cytokinins in stem bark; O-methylzeatin nucleotide and O-methylzeatin 9-riboside, metabolites of exogenous zeatin riboside in excised pod walls.

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