Yokonolide A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02981 |
| CAS | |
| Molecular Weight | 886.16 |
| Molecular Formula | C47H83NO14 |
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Description
It is produced by the strain of Streptomyces diastatochromogenes B59. It can inhibit the signal transduction of thaliphin.
Specification
| Synonyms | (1S,4E,6R,6'R,7S,8R,9R,10R,11S,12S,16E,18S,19S,21S,23R,25R)-6,7,9,11,19-Pentahydroxy-6'-[(2R)-2-hydroxybutyl]-18-[(2S)-3-hydroxy-2-methylpropyl]-6,8,12,25-tetramethyl-3-oxo-3',4',5',6'-tetrahydrospiro[2,22-dioxabicyclo[19.3.1]pentacosa-4,16-diene-23,2'-pyran]-10-yl 2,4,6-trideoxy-4-(dimethylamino)-alpha-L-lyxo-hexopyranoside |
| IUPAC Name | (1S,4E,6R,6'R,7S,8R,9R,10R,11S,12S,16E,18S,19S,21S,23R,25R)-10-[(2S,4S,5S,6S)-5-(dimethylamino)-4-hydroxy-6-methyloxan-2-yl]oxy-6,7,9,11,19-pentahydroxy-6'-[(2R)-2-hydroxybutyl]-18-[(2S)-3-hydroxy-2-methylpropyl]-6,8,12,25-tetramethylspiro[2,22-dioxabicyclo[19.3.1]pentacosa-4,16-diene-23,2'-oxane]-3-one |
| Canonical SMILES | CCC(CC1CCCC2(O1)CC3C(C(O2)CC(C(C=CCCCC(C(C(C(C(C(C(C=CC(=O)O3)(C)O)O)C)O)OC4CC(C(C(O4)C)N(C)C)O)O)C)CC(C)CO)O)C)O |
| InChI | InChI=1S/C47H83NO14/c1-10-33(50)22-34-17-14-19-47(61-34)25-38-29(4)37(62-47)23-35(51)32(21-27(2)26-49)16-13-11-12-15-28(3)42(54)44(60-40-24-36(52)41(48(8)9)31(6)58-40)43(55)30(5)45(56)46(7,57)20-18-39(53)59-38/h13,16,18,20,27-38,40-45,49-52,54-57H,10-12,14-15,17,19,21-26H2,1-9H3/b16-13+,20-18+/t27-,28-,29+,30+,31-,32+,33+,34+,35-,36-,37-,38-,40-,41+,42-,43+,44+,45-,46+,47+/m0/s1 |
| InChI Key | FDTRCZDJIYMYRH-KZTVNNGNSA-N |
Properties
| Appearance | White Powder |
| Boiling Point | 983.8±65.0°C at 760 mmHg |
| Melting Point | 117°C |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Chloroform |
Reference Reading
1. Yokonolide A, a new inhibitor of auxin signal transduction, from Streptomyces diastatochromogenes B59
K Hayashi, K Ogino, Y Oono, H Uchimiya, H Nozaki J Antibiot (Tokyo). 2001 Jul;54(7):573-81. doi: 10.7164/antibiotics.54.573.
Bio-probes that inhibit the action of auxin are useful tools for the study of auxin signaling. To screen for specific inhibitors of auxin signaling, we used an Arabidopsis transgenic line harboring the auxin-inducible promoter derived from PS-IAA4/5 and the reporter gene, GUS (beta-glucuronidase). In this transgenic plant, the exogenous auxin specifically enhanced the expression of the GUS reporter gene. A novel 22-membered spiroketal-macrolide, yokonolide A (1), and related previously known compound, A82548A (2), were isolated from Streptomyces diastatochromogenes B59 as inhibitors of auxin inducible gene expression. The absolute structure of I was determined by detailed spectral analyses and chemical derivatization. 1 and 2 completely inhibited the auxin-induced transcription of the reporter gene at 5 and 1 microm, respectively. In contrast, 1 and 2 did not affect the translation of GUS reporter transcripts. In addition, 1 and 2 did not inhibit the gibberellin-induced alpha-amylase expression at 100 microM in barley aleurone cells. These results suggest that 1 and 2 specifically inhibit auxin signaling leading to auxin-mediated gene expression.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
