Cuevaene B

Cuevaene B

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Category Bioactive by-products
Catalog number BBF-01090
CAS 274684-11-6
Molecular Weight 388.41
Molecular Formula C21H24O7

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Description

It is produced by the strain of Streptomyces sp. HKI 0180. It has a moderate level of activity against gram-positive bacteria, Its MIC against Staphylococcus aureus and Bacillus subtilis is greater than 50 μg/mL.

Specification

IUPAC Name (2E,4Z,6E)-7-[2-hydroxy-3-(2,4,5-trihydroxyphenyl)cyclohex-2-en-1-yl]-4-methoxy-6-methylhepta-2,4,6-trienoic acid
Canonical SMILES CC(=CC1CCCC(=C1O)C2=CC(=C(C=C2O)O)O)C=C(C=CC(=O)O)OC
InChI InChI=1S/C21H24O7/c1-12(9-14(28-2)6-7-20(25)26)8-13-4-3-5-15(21(13)27)16-10-18(23)19(24)11-17(16)22/h6-11,13,22-24,27H,3-5H2,1-2H3,(H,25,26)/b7-6+,12-8+,14-9-
InChI Key WKLFGCOQAHCWHB-PINZUCEXSA-N

Properties

Appearance Waxy Matter
Antibiotic Activity Spectrum Gram-positive bacteria
Solubility Soluble in Methanol

Reference Reading

1. Cuevaenes C-E: Three new triene carboxylic derivatives from Streptomyces sp. LZ35ΔgdmAI
Jing-Jing Deng, Chun-Hua Lu, Yao-Yao Li, Shan-Ren Li, Yue-Mao Shen Beilstein J Org Chem. 2014 Apr 15;10:858-862. doi: 10.3762/bjoc.10.82. eCollection 2014.
Two pairs of geometrical isomers - cuevaenes A (1) and C (3) as well as cuevaenes D (4) and E (5) - and cuevaene B (2) were isolated from gdmAI-disrupted Streptomyces sp. LZ35. The constitution of cuevaene C (3) was found to be identical to cuevaene A (1) by means of NMR spectroscopy and high resolution mass spectrometry. However, the relative configurations of the triene side chain moieties were determined to be different. It was established on the basis of spectroscopic data that cuevaenes D (4) and E (5) are amides and geometrical isomers. Cuevaenes A-C (1-3) displayed moderate activity against Gram-positive bacteria (e.g., Bacillus subtilis strain ATCC 11060) and modest activity against fungi (e.g., Fusarium verticillioides strain S68 and Rhizoctonia solani strain GXE4). However, cuevaenes D (4) and E (5) showed no inhibitory activity against any of the tested microbes.

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* 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

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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