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141 results on '"Wang, Yong‐Heng"'

11. Discovery of a Potent Antiosteoporotic Drug Molecular Scaffold Derived from Angelica sinensisand Its Bioinspired Total Synthesis

Author

Zou, Jian, Qiu, Zuo-Cheng, Yu, Qiang-Qiang, Wu, Jia-Ming, Wang, Yong-Heng, Shi, Ke-Da, Li, Yi-Fang, He, Rong-Rong, Qin, Ling, Yao, Xin-Sheng, Wang, Xin-Luan, and Gao, Hao

Abstract

Angelica sinensis, commonly known as Dong Quai in Europe and America and as Dang-gui in China, is a medicinal plant widely utilized for the prevention and treatment of osteoporosis. In this study, we report the discovery of a new category of phthalide from Angelica sinensis, namely falcarinphthalides A and B (1and 2), which contains two fragments, (3R,8S)-falcarindiol (3) and (Z)-ligustilide (4). Falcarinphthalides A and B (1and 2) represent two unprecedented carbon skeletons of phthalide in natural products, and their antiosteoporotic activities were evaluated. The structures of 1and 2, including their absolute configurations, were established using extensive analysis of NMR spectra, chemical derivatization, and ECD/VCD calculations. Based on LC-HR-ESI-MS analysis and DFT calculations, a production mechanism for 1and 2involving enzyme-catalyzed Diels−Alder/retro-Diels−Alder reactions was proposed. Falcarinphthalide A (1), the most promising lead compound, exhibits potent in vitro antiosteoporotic activity by inhibiting NF-κB and c-Fos signaling-mediated osteoclastogenesis. Moreover, the bioinspired gram-scale total synthesis of 1, guided by intensive DFT study, has paved the way for further biological investigation. The discovery and gram-scale total synthesis of falcarinphthalide A (1) provide a compelling lead compound and a novel molecular scaffold for treating osteoporosis and other metabolic bone diseases.

Published
2024
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15. Oxidative aromatization mechanism of ligustilide.

Author

Zhuang, Yu-Qing, Zou, Jian, Zhang, Sheng-Yuan, Wu, Jia-Ming, Long, Liang, Chen, Xian-Bo, Chen, Guo-Dong, Hu, Dan, Wang, Yong-Heng, and Gao, Hao

Subjects
AROMATIZATION, REACTIVE oxygen species, CHEMICAL reactions, PHTHALIDES
Abstract

The aromatization mechanisms of ligustilide (1), a versatile monomeric phthalide, were investigated. DFT calculations combined with control experiments prove that the aromatization could result from direct oxidation by triplet oxygen in mild conditions with no catalyst, which is generally thought to be difficult. Moreover, it is predicted that the aromatization could rapidly clear away the harmful-to-organism singlet oxygen, which may be relevant to the general antioxidation activity of phthalides, providing a new point of view to understand the bioactivity from chemical reaction. [ABSTRACT FROM AUTHOR]

Published
2023
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23. Biotransformation of α-asarone by Alternaria longipes CGMCC 3.2875

Author

Chen Guodong, Gao Hao, Wang Yong-Heng, Dan Hu, Zhou Zheng-Qun, Li Ning, Zhao Huan, Zou Jian, Yao Xin-sheng, and Zhang Shuai

Subjects
Quantum chemical, Molecular Structure, Stereochemistry, Alternaria longipes, Positive control, Alternaria, Allylbenzene Derivatives, General Medicine, Anisoles, Lignans, NMR spectra database, chemistry.chemical_compound, Complementary and alternative medicine, Biotransformation, chemistry, Magnosalicin, Drug Discovery, Asarone
Abstract

Biotransformation of α-asarone by Alternaria longipes CGMCC 3.2875 yielded two pairs of new neolignans, (+) (7S, 8S, 7′S, 8′R) iso-magnosalicin ( 1a )/(−) (7R, 8R, 7'R, 8′S) iso-magnosalicin ( 1b ) and (+) (7R, 8R, 7′S, 8'R) magnosalicin ( 2a )/(−) (7S, 8S, 7′R, 8'S) magnosalicin ( 2b ), and four known metabolites, (±) acoraminol A ( 3 ), (±) acoraminol B ( 4 ), asaraldehyde ( 5 ), and 2, 4, 5-trimethoxybenzoic acid ( 6 ). Their structures, including absolute configurations, were determined by extensive analysis of NMR spectra, X-ray crystallography, and quantum chemical ECD calculations. The cytotoxic activity and Aβ42 aggregation inhibitory activity of all the compounds were evaluated. Compound 2 displayed significant anti-Aβ42 aggregation activity with an inhibitory rate of 60.81% (the positive control EGCG: 69.17%). In addition, the biotransformation pathway of α-asarone by Alternaria longipes CGMCC 3.2875 was proposed.

Published
2021

43. Metal‐catalyzed alkyne oxidation/CH functionalization: Effects of oxidant, temperature, and metal catalyst on chemoselectivity.

Author

Wang, Yong‐Heng, Wu, An‐An, Tan, Kai, and Lu, Xin

Subjects
*GOLD catalyst activity, *INTERMOLECULAR interactions, *METAL catalysts, *CHEMOSELECTIVITY, *DENSITY functional theory, *TEMPERATURE effect, *METAL carbenes
Abstract

Gold‐catalyzed intermolecular alkyne oxidation has attracted much synthetic attention, but mostly suffering undesired over‐oxidation. Recent experiments demonstrated that over‐oxidation could be dramatically suppressed in zinc(II)‐catalyzed intermolecular alkyne oxidation/CH functionalization. By means of first‐principle density functional theory calculations, we explored the mechanism of the M‐catalyzed intermolecular alkyne oxidations (M = Zn(OTf)2 and Au+PR3) as well as the effects of oxidants, temperature, and metal catalysts on chemoselectivity, in an effort to disclose the origin of the extraordinary chemoselectivity pertaining to zinc catalysis. Our calculations indicate that the Zn‐catalyzed intermolecular alkyne oxidation/CH functionalization proceeds by a Friedel–Crafts alkylation mechanism rather than metal carbene insertion mechanism. The chemoselectivity of CH functionalization against over‐oxidation in Zn catalysis, in comparison with gold catalysis, can be jointly controlled by four factors: (1) the use of less nucleophilic N‐oxide, (2) the enhanced electrophilicity and carbocationic nature of the carbenic site in the α‐oxo metal carbenoid intermediate, (3) enhanced steric repulsion to incoming oxidant exerted by bulky ancillary ligand in the close nearby of the carbenic site to disfavor intermolecular over‐oxidation and (4) the large negative value of activation entropy in the intermolecular over‐oxidation pathway, that jointly give rise to lower activation free energy for the intramolecular cyclization/CH functionalization pathway than for the intermolecular over‐oxidation pathway. © 2018 Wiley Periodicals, Inc. The mechanism of zinc(II)‐catalyzed alkyne oxidation/CH functionalization was investigated theoretically and the related factors that affect the chemoselectivity between CH functionalization and over‐oxidation were disclosed computationally. [ABSTRACT FROM AUTHOR]

Published
2019
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