- Identification of a Novel TRPM8 Agonist from Nutmeg: A Promising Cooling Compound
-
The transient receptor potential melastatin 8 (TRPM8) ion channel is the primary receptor for innocuous cold stimuli (8′-7-ethoxy-4-hydroxy-3,3′,5′-trimethoxy-8-O-4′-neolignan (1) with an EC50 of 0.332 μM, which was isolated from a well-known spice, nutmeg (Myristica fragrans Houtt.). Structure activity relationships are also disclosed, showing that the 7-d-menthoxy derivative is the most potent agonist (EC50 = 11 nM). The combination of 1 and l-(-)-menthol has an additive effect, suggesting that neolignan compounds interact with TRPM8 at different sites from those of l-(-)-menthol.
- Shirai, Tomohiro,Kumihashi, Kentaro,Sakasai, Mitsuyoshi,Kusuoku, Hiroshi,Shibuya, Yusuke,Ohuchi, Atsushi
-
p. 715 - 719
(2017/07/22)
-
- Asymmetric synthesis of the natural erythro-(1R,2S)-8-O-4′-neolignan myrislignan
-
An efficient and practical asymmetric synthesis of erythro-(1R,2S)-8-O- 4′-neolignan myrislignan was achieved by using vanillin and pyrogallic acid as the starting materials. Two key steps are involved: preparation of an enantiopure threo alcohol of predictable stereochemistry by dihydroxylation with AD-mix-β, and inversion of the absolute configuration from the threo to the erythro isomer using a Mitsunobu reaction. The route illustrates a new methodology for the synthesis of erythro-8-O-4′-neolignan. Graphical abstract: [Figure not available: see fulltext.]
- Xia,Wang, Wei
-
-