Polycyclic polyprenylated acylphloroglucinols with acetylcholinesterase inhibitory activities from Hypericum perforatum

Lou, Hua‐Yong; Yi, Ping; Hu, Zhan-Xing; Li, Yanan; Zeng, Yan-Rong; Gu, Wei; Huang, Liejun; Yuan, Chun‐Mao; Hao, Xiao‐Jiang

doi:10.1016/j.fitote.2020.104550

Cited by 20 publications

(12 citation statements)

References 27 publications

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“…Other miscellenous compounds ( Table S4 ) have equally shown interesting acetylcho-linesterase and butyrylcholinesterase inhibitory activities [ 96 , 97 , 98 , 99 , 100 , 101 , 102 , 103 , 104 , 105 , 106 , 107 , 108 , 109 , 110 , 111 , 112 , 113 , 114 , 115 , 116 ].…”

Section: Discussionmentioning

confidence: 99%

Non-Alkaloid Cholinesterase Inhibitory Compounds from Natural Sources

et al. 2021

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Alzheimer’s disease (AD) is a severe neurodegenerative disorder of different brain regions accompanied by distresses and affecting more than 25 million people in the world. This progressive brain deterioration affects the central nervous system and has negative impacts on a patient’s daily activities such as memory impairment. The most important challenge concerning AD is the development of new drugs for long-term treatment or prevention, with lesser side effects and greater efficiency as cholinesterases inhibitors and the ability to remove amyloid-beta(Aβ) deposits and other related AD neuropathologies. Natural sources provide promising alternatives to synthetic cholinesterase inhibitors and many have been reported for alkaloids while neglecting other classes with potential cholinesterase inhibition. This review summarizes information about the therapeutic potential of small natural molecules from medicinal herbs, belonging to terpenoids, coumarins, and phenolic compounds, and others, which have gained special attention due to their specific modes of action and their advantages of low toxicity and high efficiency in the treatment of AD. Some show superior drug-like features in comparison to synthetic cholinesterase inhibitors. We expect that the listed phytoconstituents in this review will serve as promising tools and chemical scaffolds for the discovery of new potent therapeutic leads for the amelioration and treatment of Alzheimer’s disease.

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Section: Discussionmentioning

confidence: 99%

Non-Alkaloid Cholinesterase Inhibitory Compounds from Natural Sources

et al. 2021

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“…that of being linked by C-7'; (iii) the mixtures of (+)-6 /(-)-6 and (+)-8/(-)-8 showed stronger AChE inhibitory activities than (+)-6, (-)-6, (+)-8, or (-)-8. Compared with structurally diverse acylphloroglucinol-like compounds reported from various plants[30][31][32][33][34], acylphloroglucinols and the mixture of 10 and 11 isolated from E. robusta fruits displayed more potential AChE inhibitory effects. With regard to acylphloroglucinol derivatives obtained from species of Myrtaceae, apart from polymethylated phloroglucinol meroterpenoids (PPMs) isolated from…”

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confidence: 90%

Acylphloroglucinols with acetylcholinesterase inhibitory effects from the fruits of Eucalyptus robusta

Liu

Feng

et al. 2020

Bioorganic Chemistry

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Eleven new acylphloroglucinols, including seven new formylated phloroglucinol-monoterpene meroterpenoids, eucalyprobusals A-F (1-6), one monomeric acylphloroglucinol, eucalyprobusone B (7), and four dimeric acylphloroglucinols, eucalyprobusones C-F (8-11) were purified from the fruits of Eucalyptus robusta. The establishment of the structures of 1-11 was achieved by a combination of NMR and HRESIMS data analyses, electron circular dichroism (ECD), and single-crystal X-ray diffraction. Compounds 6, 8, and an inseparable mixture of 10 and 11 were found to be potent AChE inhibitors with IC50 values of 3.22 ± 0.36, 3.82 ± 0.22, and 2.55 ± 0.28 μΜ, respectively. Possible interaction sites of 6, 8, 10, and 11 with AChE were investigated by means of molecular docking studies, and the results revealed that AChE residues Asn87, Ser125, Thr83, Tyr133, Tyr124, Tyr337, and Tyr341 played crucial roles in the observed activity of the aforementioned compounds.

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“…The AChE inhibitory activities of the isolated compounds were assayed by a modified Ellman’s method [ 6 , 23 ]. Compounds and positive control were dissolved in 1% DMSO.…”

Section: Methodsmentioning

confidence: 99%

Discovery of Three New Monoterpenoid Indole Alkaloids from the Leaves of Gardneria multiflora and Their Vasorelaxant and AChE Inhibitory Activities

Zhang

Chen

et al. 2021

Molecules

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Three novel monoterpenoid indole alkaloids gardflorine A (1), gardflorine B (2), and gardflorine C (3) were isolated from the leaves of Gardneria multiflora. Their structures, including absolute configurations, were established on the basis of spectroscopic methods (MS, UV, IR, 1D and 2D NMR) and circular dichroism experiments. All the compounds were evaluated for their vasorelaxant and acetylcholinesterase (AChE) inhibitory activities. Compound 1 exhibited potent vasorelaxant activity, with an EC50 value of 8.7 μM, and compounds 2 and 3 showed moderate acetylcholinesterase (AChE) inhibitory activities, with IC50 values of 26.8 and 29.2 μM, respectively.

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Polycyclic polyprenylated acylphloroglucinols with acetylcholinesterase inhibitory activities from Hypericum perforatum

Cited by 20 publications

References 27 publications

Non-Alkaloid Cholinesterase Inhibitory Compounds from Natural Sources

Non-Alkaloid Cholinesterase Inhibitory Compounds from Natural Sources

Acylphloroglucinols with acetylcholinesterase inhibitory effects from the fruits of Eucalyptus robusta

Discovery of Three New Monoterpenoid Indole Alkaloids from the Leaves of Gardneria multiflora and Their Vasorelaxant and AChE Inhibitory Activities

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