32492-74-3Relevant academic research and scientific papers
Inhibitors of nitric oxide production from the bark of Myrica rubra: Structures of new biphenyl type diarylheptanoid glycosides and taraxerane type triterpene
Tao, Jing,Morikawa, Toshio,Toguchida, Iwao,Ando, Shin,Matsuda, Hisashi,Yoshikawa, Masayuki
, p. 4005 - 4012 (2002)
Three new biphenyl type diarylheptanoid glycosides, myricanol 11-O-β-D-glucopyranoside, myricanone 5-O-β-D-glucopyranoside, and neomyricanone 5-O-β-D-glucopyranoside, and a new taraxerane type triterpene, myricetrione, were isolated from the bark of Chinese Myrica rubra. Their structures were elucidated on the basis of chemical and physicochemical evidence. Biphenyl type diarylheptanoids, triterpene, and their polyphenols showed potent inhibitory effects on nitric oxide production in lipopolysaccharide-activated macrophages. Furthermore, diarylheptanoids, myricanol and myricanone, were found to inhibit induction of inducible nitric oxide synthase.
Synthesis, stereochemical analysis, and derivatization of myricanol provide new probes that promote autophagic Tau clearance
Martin, Mackenzie D.,Calcul, Laurent,Smith, Courtney,Jinwal, Umesh K.,Fontaine, Sarah N.,Darling, April,Seeley, Kent,Wojtas, Lukasz,Narayan, Malathi,Gestwicki, Jason E.,Smith, Garry R.,Reitz, Allen B.,Baker, Bill J.,Dickey, Chad A.
, p. 1099 - 1109 (2015/05/05)
We previously discovered that one specific scalemic preparation of myricanol (1), a constituent of Myrica cerifera (bayberry/southern wax myrtle) root bark, could lower the levels of the microtubule-associated protein tau (MAPT). The significance is that tau accumulates in a number of neurodegenerative diseases, the most common being Alzheimers disease (AD). Herein, a new synthetic route to prepare myricanol using a suitable boronic acid pinacol ester intermediate is reported. An X-ray crystal structure of the isolated myricanol (1) was obtained and showed a co-crystal consisting of (+)-aR,11S-myricanol (2) and (-)-aS,11R-myricanol (3) coformers. Surprisingly, 3, obtained from chiral separation from 1, reduced tau levels in both cultured cells and ex vivo brain slices from a mouse model of tauopathy at reasonable mid-to-low micromolar potency, whereas 2 did not. SILAC proteomics and cell assays revealed that 3 promoted tau degradation through an autophagic mechanism, which was in contrast to that of other tau-lowering compounds previously identified by our group. During the course of structure-activity relationship (SAR) development, we prepared compound 13 by acid-catalyzed dehydration of 1. 13 had undergone an unexpected structural rearrangement through the isomyricanol substitution pattern (e.g., 16), as verified by X-ray structural analysis. Compound 13 displayed robust tau-lowering activity, and, importantly, its enantiomers reduced tau levels similarly. Therefore, the semisynthetic analogue 13 provides a foundation for further development as a tau-lowering agent without its SAR being based on chirality.
MYRICANOL DERIVATIVES AND USES THEREOF FOR TREATMENT OF NEURODEGENERATIVE DISEASES
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Page/Page column 24, (2013/10/22)
The subject invention pertains to myricanol derivatives, therapeutic compositions, and methods for treatment of neurodegenerative diseases, in particular, neurodegenerative diseases associated with abnormal accumulation of protein tau.
Diarylheptanoid sulfates and related compounds from myrica rubra bark
Yoshimura, Morio,Yamakami, Saori,Amakura, Yoshiaki,Yoshida, Takashi
, p. 1798 - 1802 (2013/01/15)
Three new diarylheptanoids, myricanol 11-sulfate (1), juglanin B 11-sulfate (2), and myricanone 5-O-(6′-O-galloyl)glucoside (3), were isolated from the bark of Myrica rubra. Compounds 1 and 2 were characterized as diarylheptanoid sulfates on the basis of spectroscopic analyses. The antioxidative activities of the fractionated extracts and isolated compounds were estimated by the oxygen radical absorbance capacity (ORAC) and superoxide dismutase (SOD)-like activity assays. The major isolate, myricitrin (4), displayed a high ORAC value and moderate SOD-like activity (13 198 μmol TE (Trolox equivalent)/g and IC50 127.5 μg/mL, respectively), which might explain the potent antioxidative activity of this material.
Bioactive constituents of Chinese natural medicines. VII.1 Inhibitors of degranulation in RBL-2H3 cells and absolute stereostructures of three new diarylheptanoid glycosides from the bark of Myrica rubra
Matsuda, Hisashi,Morikawa, Toshio,Tao, Jing,Ueda, Kazuho,Yoshikawa, Masayuki
, p. 208 - 215 (2007/10/03)
Three new diarylheptanoid glycosides, named (+)-S-myricanol 5-O-β-D-glucopyranoside, myricanene A 5-O-α-L- arabinofuranosyl(1→6)-β-D-glucopyranoside, and myricanene B 5-O-α-L-arabinofuranosyl(1→6)-β-D-glucopyranoside, were isolated from the bark of Chines
Total Syntheses of the meta,meta-Bridged Biphenyls (+/-)-Myricanol and Myricanone, and of an Isomeric Biphenyl Ether, a 14-Oxametaparacyclophane
Whiting, Donald A.,Wood, Andrew F.
, p. 623 - 628 (2007/10/02)
The oxidative coupling of 1,7-bis(hydroxyphenyl)heptanoids (2a,b) has been investigated: C-C coupling to meta,meta-bridged biaryls was not observed, but with thallium tris(trifluoroacetate) C-O coupling occurred forming a 14-oxametaparacyclophane analogous to the natural phenols acerogenin-A and galeon.Intramolecular reductive coupling, using tetrakis(triphenylphosphine)nickel(0), of the bis-iodides (11a,b) derived from phenols (2a,b), leads, after deprotection, to the desired meta,meta-bridged biphenyls myricanone and (+/-)-myricanol, albeit in rather low yield.OO-Dimethylmyricanone and (+/-)-OO-dimethylmyricanol were similarly synthesized.Irradiation (254 nm) in alkaline ethanol of the bromides (11g,h) also induced aryl-aryl coupling to form dibenzylmyricanone and (+/-)-dibenzylmyricanol acetate respectively.
