Terreulactone D

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Category Enzyme inhibitors
Catalog number BBF-03108
CAS
Molecular Weight 556.60
Molecular Formula C30H36O10

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Description

Tetracycline D is an acetylcholinesterase (AchE, EC3. 1.1.7) inhibitor produced by Aspergillus terreus. It has a strong inhibition of AchE activity with IC50 of 0.42 µmol/L.

Specification

IUPAC Name (1S,2S,7R,10R)-1,7-dihydroxy-5-methoxy-2,6,6,10-tetramethyl-14-(3,4,5-trimethoxyphenyl)-11,15-dioxatetracyclo[8.8.0.02,7.012,17]octadeca-4,12(17),13-triene-3,16-dione
Canonical SMILES CC1(C(=CC(=O)C2(C1(CCC3(C2(CC4=C(O3)C=C(OC4=O)C5=CC(=C(C(=C5)OC)OC)OC)O)C)O)C)OC)C
InChI InChI=1S/C30H36O10/c1-26(2)23(37-7)14-22(31)28(4)29(26,33)10-9-27(3)30(28,34)15-17-19(40-27)13-18(39-25(17)32)16-11-20(35-5)24(38-8)21(12-16)36-6/h11-14,33-34H,9-10,15H2,1-8H3/t27-,28+,29-,30-/m1/s1
InChI Key AENKBRFCOPMCEQ-GOGZTAQTSA-N

Properties

Appearance White Powder
Boiling Point 723.5±60.0°C at 760 mmHg
Density 1.4±0.1 g/cm3

Reference Reading

1. Bioactive α-pyrone meroterpenoids from mangrove endophytic fungus Penicillium sp
Bo Ding, Zhiyuan Wang, Xishan Huang, Yayue Liu, Wenrui Chen, Zhigang She Nat Prod Res. 2016 Dec;30(24):2805-2812. doi: 10.1080/14786419.2016.1164702. Epub 2016 Apr 11.
Five α-pyrone meroterpenoids, including one new 3-epiarigsugacin E (1) and four known compounds, arisugacin D (2), arisugacin B (3), territrem C (4) and terreulactone C (5) were obtained from the marine fungus Penicillium sp. SK5GW1L. Their structures were identified by MS and NMR experiments, and the absolute configuration of compound 1 was further confirmed by low temperature (150 K) single crystal X-ray diffraction with Cu Kα radiation. Compounds 3, 4 and 5 showed strong inhibitory activities against acetylcholinesterase (AchE) with IC50 values of 3.03, 0.23 and 0.028 μM, respectively.

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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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