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Terreulactone C

Name: Terreulactone C
Brand: BOC Sciences
Rating: 5 (1 reviews)

* Please be kindly noted products are not for therapeutic use. We do not sell to patients.

Category	Enzyme inhibitors
Catalog number	BBF-03107
CAS
Molecular Weight	468.54
Molecular Formula	C27H32O7

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Tetracycline C is an acetylcholinesterase (AchE, EC3. 1.1.7) inhibitor produced by Aspergillus terreus. It has a strong inhibition of AchE activity with IC50 of 0.06 µmol/L.

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IUPAC Name	(1S,2S,7S,10R)-1,7-dihydroxy-14-(4-methoxyphenyl)-2,6,6,10-tetramethyl-11,15-dioxatetracyclo[8.8.0.02,7.012,17]octadeca-12(17),13-diene-5,16-dione
Canonical SMILES	CC1(C(=O)CCC2(C1(CCC3(C2(CC4=C(O3)C=C(OC4=O)C5=CC=C(C=C5)OC)O)C)O)C)C
InChI	InChI=1S/C27H32O7/c1-23(2)21(28)10-11-24(3)26(23,30)13-12-25(4)27(24,31)15-18-20(34-25)14-19(33-22(18)29)16-6-8-17(32-5)9-7-16/h6-9,14,30-31H,10-13,15H2,1-5H3/t24-,25+,26+,27-/m0/s1
InChI Key	ARZWKYJFXLHKCZ-YAOOYPAMSA-N

Appearance	White Powder
Boiling Point	642.2±55.0°C at 760 mmHg
Density	1.3±0.1 g/cm3

1. Studies directed toward the synthesis of terreulactone A: rapid construction of the A, B, C rings

Haibo Liu, Dionicio R Siegel, Samuel J Danishefsky Org Lett. 2006 Feb 2;8(3):423-5. doi: 10.1021/ol052618p.

[structure: see text]. An efficient, rapid synthesis of the A, B, C rings of terreulactone A is described. Key steps in the synthesis include a diastereoselective benzylic acid rearrangement to create the desired quaternary center at C2 and a mild bromolactonization to assemble the lactonic ring A.

2. 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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