Structural revision of a Wnt/β-catenin modulator and confirmation of cannabielsoin constitution and configuration

被引：10

作者：

Monroe, Angelina Z. ^{[1
]}

Gordon, William H. ^{[1
]}

Wood, Jared S. ^{[1
]}

Martin, Gary E. ^{[2
]}

Morgan, Jeremy B. ^{[1
]}

Williamson, R. Thomas ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem & Biochem, Wilmington, NC 28409 USA

[2] Seton Hall Univ, Dept Chem, S Orange, NJ 07079 USA

来源：

CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 46期

基金：

美国国家科学基金会;

关键词：

3D STRUCTURE ELUCIDATION; RELATIVE CONFIGURATION; GUINEA-PIG; CANNABIDIOL; METABOLITE; CANNABINOIDS; COUPLINGS; CB1;

D O I：

10.1039/d1cc01971f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this report, we revise the structure for a previously reported synthetic product proposed to be the 1R,2S-cannabidiol epoxide and reassign it as cannabielsoin using anisotropic NMR and synthetic chemistry methods. These results provide a direct link to the first known biological target and function of cannabielsoin.

引用

页码：5658 / 5661

页数：4

共 50 条

[31] Establishing a "Ring-Size-Divergent" Synthetic Strategy: Synthesis, Structural Revision, and Absolute Configuration of Feroniellins
Nishikawa, Keisuke
Niwa, Toshiki
Nishikibe, Kento
Kumagai, Momochika
Morimoto, Yoshiki
CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (43) : 11045 - 11049
[32] Absolute Configuration of Oxabornyl Polyenes Prugosenes A1-A3 and Structural Revision of Prugosene A2
Lin, Fu-Long
Gao, Jia-Ling
Xu, Qian
Wang, Gao-Qian
Xiao, Liang-Yan
Dong, Lu
Tang, Wei
Lv, Jian-Ming
Chen, Guo-Dong
Wang, Ying
Yin, Zhi-Nan
Lu, Li-Gong
Hu, Dan
Gao, Hao
JOURNAL OF NATURAL PRODUCTS, 2024, 87 (05): : 1338 - 1346
[33] Structural Basis of the Interaction between Human Axin2 and SIAH1 in the Wnt/β-Catenin Signaling Pathway
Chen, Lianqi
Liu, Yan-Ping
Tian, Li-Fei
Li, Mingzhou
Yang, Shuyu
Wang, Song
Xu, Wenqing
Yan, Xiao-Xue
BIOMOLECULES, 2023, 13 (04)
[34] Structural Maintenance of Chromosome Protein 4 Promotes the Progression of Cardia Adenocarcinoma via Regulation of the Wnt/β-catenin Signaling Pathway
Zhu, Mengqi
Zhang, Xinxin
Gao, Kaiji
Zhang, Lingmei
Feng, Xiaojia
Wang, Hui
Li, Jing
Jia, Jianguang
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2024, 27 (04) : 611 - 620
[35] Redefining canonical Wnt/b-catenin signaling in hepatic stellate cells as a critical modulator for fibrosis in models of alcohol- associated liver disease
Rutt, L.
Mccullough, R.
ALCOHOL, 2024, 121
[36] STIMULATION OF OROBANCHE-CRENATA SEED-GERMINATION BY (+)-STRIGOL AND STRUCTURAL ANALOGS DEPENDENCE ON CONSTITUTION AND CONFIGURATION OF THE GERMINATION STIMULANTS
BERGMANN, C
WEGMANN, K
FRISCHMUTH, K
SAMSON, E
KRANZ, A
WEIGELT, D
KOLL, P
WELZEL, P
JOURNAL OF PLANT PHYSIOLOGY, 1993, 142 (03) : 338 - 342
[37] E7386, a Wnt/ß-catenin signaling modulator, suppresses the differentiation of regulatory T cells in combination with lenvatinib plus anti-PD-1 antibody
Shen, Jialing
Ishida, Ryoga
Kume, Masahiko
Kimura, Takayuki
Adachi, Yusuke
Kato, Yu
CANCER RESEARCH, 2024, 84 (06)
[38] Biochemical and structural characterization of NuMA/b-catenin complexes involved in Wnt3adependent self-renewal
Mazzinelli, E.
Bordi, M.
Viscomi, M. T.
Scilla, F.
Lajolo, C.
Panatta, E.
Cecconi, F.
Nocca, G.
FEBS OPEN BIO, 2024, 14 : 309 - 309
[39] Biochemical and structural characterization of NuMA/b-catenin complexes involved in Wnt3adependent self-renewal
Castagna, F.
Eli, S.
Ghezzi, P.
Tomaiuolo, M.
Rizzelli, F.
Monzani, S.
Ciossani, G.
Scietti, L.
Mapelli, M.
FEBS OPEN BIO, 2024, 14 : 309 - 309
[40] Pin1 plays a critical role in Wnt3a-induced osteoblast differentiation through structural modification of β-catenin
Shin, Hea-rim
Lee, Taegyung
Cho, Young-Dan
Yoon, Won-Joon
Woo, Kyung Mi
Baek, Jeong-Hwa
Ryoo, Hyun-Mo
JOURNAL OF BONE AND MINERAL RESEARCH, 2013, 28

← 1 2 3 4 5 →