Xue-Ge Pan , Xin-Xin Li , Cong-Yuan Xia , Wei-Feng Yin , Kang Ding , Guo-Yan Zuo , Man-Ni Wang , Wei-Ku Zhang , Jun He , Jie-Kun Xu
{"title":"从贯叶连翘中提取的具有抗抑郁活性的新的多环多烯酰化酰基氯葡萄糖醇","authors":"Xue-Ge Pan , Xin-Xin Li , Cong-Yuan Xia , Wei-Feng Yin , Kang Ding , Guo-Yan Zuo , Man-Ni Wang , Wei-Ku Zhang , Jun He , Jie-Kun Xu","doi":"10.1016/j.bioorg.2024.107657","DOIUrl":null,"url":null,"abstract":"<div><p>Six new polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperidiones A-F (<strong>1</strong>–<strong>6</strong>), were obtained from <em>Hypericum perforatum</em> L. Their structures were characterized via extensive spectroscopic analyses, the circular dichroism data of the <em>in situ</em> formed [Mo<sub>2</sub>(OCOCH<sub>3</sub>)<sub>4</sub>] complexes, the nuclear magnetic resonance calculation with DP4 <sup>+</sup> probability analysis, and the calculated electronic circular dichroism (ECD) spectra. Compounds <strong>1</strong>–<strong>6</strong> are bicyclic polyprenylated acylphloroglucinols with a major bicyclo[3.3.1]nonane-2,4,9-trione skeleton. Notably, compound <strong>1</strong> is a rare PPAP with a hydroperoxy group, and a plausible biosynthetic pathway for <strong>1</strong> was proposed. Compounds <strong>4</strong> and <strong>6</strong> exhibited significant neuroprotective effects under 10 μM against corticosterone (CORT)-injured SH-SY5Y cells. Furthermore, compound <strong>4</strong> demonstrated a noteworthy antidepressant effect at the dose of 5 mg/kg in the tail suspension test (TST) of mice, which was equivalent to 5 mg/kg of fluoxetine. And it potentially exerted an antidepressant effect through the hypothalamic–pituitary–adrenal (HPA) axis.</p></div>","PeriodicalId":257,"journal":{"name":"Bioorganic Chemistry","volume":"151 ","pages":"Article 107657"},"PeriodicalIF":4.5000,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"New polycyclic polyprenylated acylphloroglucinols with antidepressant activities from Hypericum perforatum L.\",\"authors\":\"Xue-Ge Pan , Xin-Xin Li , Cong-Yuan Xia , Wei-Feng Yin , Kang Ding , Guo-Yan Zuo , Man-Ni Wang , Wei-Ku Zhang , Jun He , Jie-Kun Xu\",\"doi\":\"10.1016/j.bioorg.2024.107657\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Six new polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperidiones A-F (<strong>1</strong>–<strong>6</strong>), were obtained from <em>Hypericum perforatum</em> L. Their structures were characterized via extensive spectroscopic analyses, the circular dichroism data of the <em>in situ</em> formed [Mo<sub>2</sub>(OCOCH<sub>3</sub>)<sub>4</sub>] complexes, the nuclear magnetic resonance calculation with DP4 <sup>+</sup> probability analysis, and the calculated electronic circular dichroism (ECD) spectra. Compounds <strong>1</strong>–<strong>6</strong> are bicyclic polyprenylated acylphloroglucinols with a major bicyclo[3.3.1]nonane-2,4,9-trione skeleton. Notably, compound <strong>1</strong> is a rare PPAP with a hydroperoxy group, and a plausible biosynthetic pathway for <strong>1</strong> was proposed. Compounds <strong>4</strong> and <strong>6</strong> exhibited significant neuroprotective effects under 10 μM against corticosterone (CORT)-injured SH-SY5Y cells. Furthermore, compound <strong>4</strong> demonstrated a noteworthy antidepressant effect at the dose of 5 mg/kg in the tail suspension test (TST) of mice, which was equivalent to 5 mg/kg of fluoxetine. And it potentially exerted an antidepressant effect through the hypothalamic–pituitary–adrenal (HPA) axis.</p></div>\",\"PeriodicalId\":257,\"journal\":{\"name\":\"Bioorganic Chemistry\",\"volume\":\"151 \",\"pages\":\"Article 107657\"},\"PeriodicalIF\":4.5000,\"publicationDate\":\"2024-07-16\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Bioorganic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0045206824005625\",\"RegionNum\":2,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Bioorganic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0045206824005625","RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
New polycyclic polyprenylated acylphloroglucinols with antidepressant activities from Hypericum perforatum L.
Six new polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperidiones A-F (1–6), were obtained from Hypericum perforatum L. Their structures were characterized via extensive spectroscopic analyses, the circular dichroism data of the in situ formed [Mo2(OCOCH3)4] complexes, the nuclear magnetic resonance calculation with DP4 + probability analysis, and the calculated electronic circular dichroism (ECD) spectra. Compounds 1–6 are bicyclic polyprenylated acylphloroglucinols with a major bicyclo[3.3.1]nonane-2,4,9-trione skeleton. Notably, compound 1 is a rare PPAP with a hydroperoxy group, and a plausible biosynthetic pathway for 1 was proposed. Compounds 4 and 6 exhibited significant neuroprotective effects under 10 μM against corticosterone (CORT)-injured SH-SY5Y cells. Furthermore, compound 4 demonstrated a noteworthy antidepressant effect at the dose of 5 mg/kg in the tail suspension test (TST) of mice, which was equivalent to 5 mg/kg of fluoxetine. And it potentially exerted an antidepressant effect through the hypothalamic–pituitary–adrenal (HPA) axis.
期刊介绍：
Bioorganic Chemistry publishes research that addresses biological questions at the molecular level, using organic chemistry and principles of physical organic chemistry. The scope of the journal covers a range of topics at the organic chemistry-biology interface, including: enzyme catalysis, biotransformation and enzyme inhibition; nucleic acids chemistry; medicinal chemistry; natural product chemistry, natural product synthesis and natural product biosynthesis; antimicrobial agents; lipid and peptide chemistry; biophysical chemistry; biological probes; bio-orthogonal chemistry and biomimetic chemistry.
For manuscripts dealing with synthetic bioactive compounds, the Journal requires that the molecular target of the compounds described must be known, and must be demonstrated experimentally in the manuscript. For studies involving natural products, if the molecular target is unknown, some data beyond simple cell-based toxicity studies to provide insight into the mechanism of action is required. Studies supported by molecular docking are welcome, but must be supported by experimental data. The Journal does not consider manuscripts that are purely theoretical or computational in nature.
The Journal publishes regular articles, short communications and reviews. Reviews are normally invited by Editors or Editorial Board members. Authors of unsolicited reviews should first contact an Editor or Editorial Board member to determine whether the proposed article is within the scope of the Journal.
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