Gibbestatin B

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Category Antibiotics
Catalog number BBF-01244
CAS 89687-34-3
Molecular Weight 386.44
Molecular Formula C22H26O6

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Description

It is produced by the strain of Streptomyces sp. C39. Gibbestatin B inhibits the expression of α-amylase induced by gibberellin in De-embryoned rice and barley (IC50 is 25-50 ppm, IC100 is 100-200 ppm), and has no anti-bacterial, anti-yeast and anti-fungal effects at 100 ppm (MIC, agar dilution method using bouillon agar for bacteria and Sabouraud agar for yeast and fungi).

Specification

Synonyms Antibiotic 2-11-B
IUPAC Name 2-hydroxy-6-[(1E,3E,5S,7E)-5-[(1S)-1-methoxyethyl]-7-methyl-8-(3-methyloxiran-2-yl)-6-oxoocta-1,3,7-trienyl]benzoic acid
Canonical SMILES CC1C(O1)C=C(C)C(=O)C(C=CC=CC2=C(C(=CC=C2)O)C(=O)O)C(C)OC
InChI InChI=1S/C22H26O6/c1-13(12-19-15(3)28-19)21(24)17(14(2)27-4)10-6-5-8-16-9-7-11-18(23)20(16)22(25)26/h5-12,14-15,17,19,23H,1-4H3,(H,25,26)/b8-5+,10-6+,13-12+/t14-,15?,17-,19?/m0/s1
InChI Key WNSZZRDXVFFVPW-IDOQMONCSA-N

Properties

Appearance Yellow Powder
Boiling Point 617.4±55.0 °C (Predicted)
Melting Point >240 °C (dec.)
Density 1.247±0.06 g/cm3 (Predicted)
Solubility Soluble in Methanol, Ethanol

Reference Reading

1. Gibbestatin B inhibits the GA-induced expression of alpha-amylase expression in cereal seeds
K Hayashi, M Inoguchi, H Kondo, H Nozaki Phytochemistry. 2000 Sep;55(1):1-9. doi: 10.1016/s0031-9422(00)00204-1.
The expression of alpha-amylase in aleurone layers of barley is known to be induced by gibberellin A3 (GA). In the present study, gibbestatin B (GNB) was isolated from Streptomyces sp. C-39 as an inhibitor of the GA-induced expression of alpha-amylase in barley and rice, with IC50 values of 125 and 70 microM, respectively. GNB suppressed accumulation of GA-induced barley high-pI type B and rice RAmylA alpha-amylase transcripts. However, GNB showed no inhibitory activity on GUS expression in transgenic tobacco harboring the auxin-inducible par B promoter:: GUS fusion gene. The transcription of an abscisic acid (ABA)-inducible gene, HVA1, was unaffected by GNB. In addition, GNB prevented aleurone cells from cell death induced by GA. In tobacco and Arabidopsis plants, GNB suppressed the germination and retarded the growth of seedlings without toxicity. The growth of gai, spy and abi mutants was also retarded by GNB. Normal plants treated with GA-biosynthesis inhibitors and GA-defective and GA-signaling mutants normally have dwarf dark green leaves. However, dwarfed healthy green leaves were observed in normal plants treated with GNB. GA-induced stem elongation of plants was also detected in the presence of GNB. These analyses indicate that GNB inhibits the GA-induced expression of alpha-amylase by regulating one of the steps involved in ABA signaling, but not by acting as a weak ABA analog.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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