Polycyclic phloroglucinols as PTP1B inhibitors from Hypericum longistylum: Structures, PTP1B inhibitory activities, and interactions with PTP1B

Xiangrong Cao, Xueyuan Yang, Peixia Wang, Yue Liang, Feng Liu, Muhetaer Tuerhong, Da Qing Jin, Jing Xu, Dongho Lee, Yasushi Ohizumi, Yuanqiang Guo

Research output: Contribution to journalArticle

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Abstract

Protein tyrosine phosphatase 1B (PTP1B) has been regarded as a target for the research and development of new drugs to treat type II diabetes and PTP1B inhibitors are potential lead compounds for this type of new drugs. A phytochemical investigation to obtain new PTP1B inhibitors resulted in the isolation of four new phloroglucinols, longistyliones A–D (1–4) from the aerial parts of Hypericum longistylum. The structures of 1–4 were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analysis, and the absolute configurations of these compounds were established by comparing their experimental electronic circular dichroism (ECD) spectra with those calculated by the time-dependent density functional theory method. Compounds 1–4 possess a rare polycyclic phloroglucinol skeleton. The following biological evaluation revealed that all of the compounds showed PTP1B inhibitory effects. The further molecular docking studies indicated the strong interactions between these bioactive compounds with the PTP1B protein, which revealed the possible mechanism of PTP1B inhibition of bioactive compounds. All of the results implied that these compounds are potentially useful for the treatment of type II diabetes.

Original languageEnglish
Pages (from-to)139-148
Number of pages10
JournalBioorganic Chemistry
Volume75
DOIs
Publication statusPublished - 2017 Dec 1

Fingerprint

Non-Receptor Type 1 Protein Tyrosine Phosphatase
Phloroglucinol
Hypericum
Medical problems
Type 2 Diabetes Mellitus
Lead compounds
Phytochemicals
Circular Dichroism
Skeleton
Pharmaceutical Preparations
Density functional theory
Nuclear magnetic resonance
Antennas
Research

Keywords

  • ECD
  • Hypericum longistylum
  • Molecular docking
  • Polycyclic phloroglucinol
  • PTP1B inhibitors

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

Cite this

Polycyclic phloroglucinols as PTP1B inhibitors from Hypericum longistylum : Structures, PTP1B inhibitory activities, and interactions with PTP1B. / Cao, Xiangrong; Yang, Xueyuan; Wang, Peixia; Liang, Yue; Liu, Feng; Tuerhong, Muhetaer; Jin, Da Qing; Xu, Jing; Lee, Dongho; Ohizumi, Yasushi; Guo, Yuanqiang.

In: Bioorganic Chemistry, Vol. 75, 01.12.2017, p. 139-148.

Research output: Contribution to journalArticle

Cao, Xiangrong ; Yang, Xueyuan ; Wang, Peixia ; Liang, Yue ; Liu, Feng ; Tuerhong, Muhetaer ; Jin, Da Qing ; Xu, Jing ; Lee, Dongho ; Ohizumi, Yasushi ; Guo, Yuanqiang. / Polycyclic phloroglucinols as PTP1B inhibitors from Hypericum longistylum : Structures, PTP1B inhibitory activities, and interactions with PTP1B. In: Bioorganic Chemistry. 2017 ; Vol. 75. pp. 139-148.
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