Erinacine E

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Category Enzyme inhibitors
Catalog number BBF-00868
CAS
Molecular Weight 432.55
Molecular Formula C25H36O6

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Description

Erinacine E is a k opioid receptor agonist produced by Hericium ramosum CL24240.

Specification

Synonyms (-)-Erinacine E
IUPAC Name 9,12-dimethyl-6-propan-2-yl-14,16-dioxahexacyclo[16.3.1.04,12.05,9.013,21.015,20]docosa-1,5-diene-18,19,20,22-tetrol
Canonical SMILES CC(C)C1=C2C3CC=C4C5C(C3(CCC2(CC1)C)C)OC6C5(C(C(C4O)(CO6)O)O)O
InChI InChI=1S/C25H36O6/c1-12(2)13-7-8-22(3)9-10-23(4)15(16(13)22)6-5-14-17-19(23)31-21-25(17,29)20(27)24(28,11-30-21)18(14)26/h5,12,15,17-21,26-29H,6-11H2,1-4H3
InChI Key YUCYEVHMFBEBSC-UHFFFAOYSA-N

Properties

Appearance White Powder

Reference Reading

1. Enantioselective total syntheses of cyathane diterpenoids
Masahisa Nakada Chem Rec. 2014 Aug;14(4):641-62. doi: 10.1002/tcr.201402019. Epub 2014 Jul 28.
A Personal Account describing the enantioselective total syntheses of cyathane diterpenoids achieved in the Nakada group. A convergent approach to the cyathane scaffold, the [5-6-7] tricyclic carbon skeleton commonly found in cyathane diterpenoids, has been developed using the catalytic asymmetric intramolecular cyclopropanation (CAIMCP) and baker's yeast reduction. This approach has been successfully applied for the enantioselective total syntheses of (+)-allocyathin B2 , (-)-erinacine B, and (-)-erinacine E. The total synthesis of (-)-erinacine E has been achieved via the acyl group migratory intramolecular aldol reaction, which prevents the retro-aldol reaction and allows the construction of the strained structure. The highly efficient and stereoselective total syntheses of (-)-scabronines G, A, D, and (-)-episcabronine A have been achieved via the oxidative dearomatization/inverse electron demand Diels-Alder reaction cascade. Cascade reactions comprising three and five consecutive reactions were employed for the highly efficient total syntheses of (-)-scabronine A and (-)-episcabronine A, respectively.
2. Erinacine E as a kappa opioid receptor agonist and its new analogs from a basidiomycete, Hericium ramosum
T Saito, F Aoki, H Hirai, T Inagaki, Y Matsunaga, T Sakakibara, S Sakemi, Y Suzuki, S Watanabe, O Suga, T Sujaku, A A Smogowicz, S J Truesdell, J W Wong, A Nagahisa, Y Kojima, N Kojima J Antibiot (Tokyo). 1998 Nov;51(11):983-90. doi: 10.7164/antibiotics.51.983.
A kappa opioid receptor binding inhibitor was isolated from the fermentation broth of a basidiomycete, Hericium ramosum CL24240 and identified as erinacine E (1). Three analogs of 1 were produced by fermentation in other media and by microbial biotransformation. Of these compounds, 1 was shown to be the most potent binding inhibitor. Preliminary SAR studies of these compounds indicated that all functional groups and side chains were required for the activity. Compound 1 was a highly-selective binding inhibitor for the kappa opioid receptor: 0.8 microM (IC50) for kappa, >200 microM for mu, and >200 microM for delta opioid receptor. Compound 1 suppressed electrically-stimulated twitch responses of rabbit vas deferens with an ED50 of 14 microM. The suppression was recovered by adding a selective kappa opioid receptor antagonist nor-binaltorphimine, indicating that 1 is a kappa opioid receptor agonist.
3. Studies on inducers of nerve growth factor: synthesis of the cyathin core
D L Wright, C R Whitehead, E H Sessions, I Ghiviriga, D A Frey Org Lett. 1999 Nov 18;1(10):1535-8. doi: 10.1021/ol991032y.
[formula: see text] Compounds that induce the synthesis of nerve growth factor (NGF) are of interest as alternatives to the administration of the native peptide. We have initiated a program to study the NGF synthesis stimulating activity of the erinacine and scabronine diterpenes. Herein, we report an approach to the core cyathin system by sequential application of an oxidative coupling and [4 + 3] cycloaddition.

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