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Article ; Online: Total Synthesis of the Racemate of Laurolitsine.

Cao, Mingyu / Wang, Yiming / Zhang, Yong / Zhang, Caiyun / Chen, Niangen / Zhang, Xiaopo

2024 Volume 29, Issue 3

Abstract: The total synthesis of laurolitsine was achieved for the first time. This reaction was accomplished in 14 steps with a 2.3% yield (this was calculated using 3-hydroxy-4-methoxybenzaldehyde as the starting material) starting from two simple materials, 3- ... ...

Abstract	The total synthesis of laurolitsine was achieved for the first time. This reaction was accomplished in 14 steps with a 2.3% yield (this was calculated using 3-hydroxy-4-methoxybenzaldehyde as the starting material) starting from two simple materials, 3-hydroxy-4-methoxybenzaldehyde and 2-(3-hydroxy-4-methoxyphenyl)acetic acid, and the longest linear sequence consisted of 11 steps. The key steps included an electrophilic addition reaction in which a nitro group was reduced to an amino group using lithium tetrahydroaluminum and a Pd-catalyzed direct biaryl coupling reaction. In this paper, many of the experimental steps were optimized, and an innovative postprocessing method in which 2-(3-(benzyloxy)-4-methoxyphenyl)ethanamine is salted with oxalic acid was proposed.
Language	English
Publishing date	2024-02-05
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules29030745
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Zs.MO 81: Show issues

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Article: Gut fungi differentially response to the antipyretic (heat-clearing) and diaphoretic (exterior-releasing) traditional Chinese medicines in

Yang, Yanan / Lu, Weiying / Zhang, Xiaopo / Wu, Chongming

Frontiers in pharmacology

2022 Volume 13, Page(s) 1032919

Abstract: Antipyretic (heat-clearing) and diaphoretic (exterior-releasing) drugs are two main groups of traditional Chinese medicines (TCMs) possessing anti-microbes and anti-inflammation effects, with the former mainly through clearing pyrogens while the latter ... ...

Abstract	Antipyretic (heat-clearing) and diaphoretic (exterior-releasing) drugs are two main groups of traditional Chinese medicines (TCMs) possessing anti-microbes and anti-inflammation effects, with the former mainly through clearing pyrogens while the latter through promoting diaphoresis. Although anti-microorganism is a common action of these two kinds of TCMs, their difference in antimicrobial spectrums and their interactions when combinedly used remain unclear. Herein, we prepared aqueous extracts from
Language	English
Publishing date	2022-11-18
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2587355-6
ISSN	1663-9812
ISSN	1663-9812
DOI	10.3389/fphar.2022.1032919
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Article ; Online: Discovery of Cadinane-Type Sesquiterpenoids from the Infected Stems of

Chen, Deli / Xu, Xudong / Yang, Yun / Meng, Hui / Xu, Minghui / Dong, Lin / Ma, Guoxu / Zhang, Xiaopo

Journal of agricultural and food chemistry

2024 Volume 72, Issue 8, Page(s) 4089–4099

Abstract: Ten new cadinane-type sesquiterpenoids, named hibisceusins I-R ( ...

Abstract	Ten new cadinane-type sesquiterpenoids, named hibisceusins I-R (
MeSH term(s)	Fungicides, Industrial/pharmacology ; Hibiscus/chemistry ; Molecular Structure ; Sesquiterpenes/chemistry ; Polycyclic Sesquiterpenes ; Quaternary Ammonium Compounds
Chemical Substances	cadinane ; HK 27 (54627-48-4) ; Fungicides, Industrial ; Sesquiterpenes ; Polycyclic Sesquiterpenes ; Quaternary Ammonium Compounds
Language	English
Publishing date	2024-02-14
Publishing country	United States
Document type	Journal Article
ZDB-ID	241619-0
ISSN	1520-5118 ; 0021-8561
ISSN (online)	1520-5118
ISSN	0021-8561
DOI	10.1021/acs.jafc.3c08508
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Zs.A 1172: Show issues

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Article: Two new aporphine alkaloids with glucose consumption increasing activity from Cassytha filiformis

Huang, Zibao / Cao, Mingyu / Wang, Ruiqi / Zhang, Yong / Zhang, Xiaopo / Dong, Lin / Zhang, Caiyun

Phytochemical Society of Europe Phytochemistry letters. 2022 Oct., v. 51

2022

Abstract: Two new aporphine alkaloids, named precassythine (1) and (+)− 6S-ocotecine-N-oxide (2), were isolated from Cassytha filiformis. The new structures were elucidated by applying various spectroscopic techniques, including 1D-, ²D NMR and HRESIMS. The ... ...

Abstract	Two new aporphine alkaloids, named precassythine (1) and (+)− 6S-ocotecine-N-oxide (2), were isolated from Cassytha filiformis. The new structures were elucidated by applying various spectroscopic techniques, including 1D-, ²D NMR and HRESIMS. The absolute configurations of 1 and 2 were determined by calculated electronic circular dichroism (ECD). Both compounds were evaluated for their effects on glucose consumption on HL-7702 cells at different concentrations. The results showed that the two new compounds significantly increased glucose consumption.
Keywords	Cassytha filiformis ; circular dichroism spectroscopy ; glucose ; plant biochemistry
Language	English
Dates of publication	2022-10
Size	p. 23-27.
Publishing place	Elsevier Ltd
Document type	Article
ISSN	1874-3900
DOI	10.1016/j.phytol.2022.06.013
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Article ; Online: A new labdane diterpenoid from Scoparia dulcis improving pancreatic function against islets cell apoptotic by Bax/Bcl-2/Caspase-3 pathway.

Dong, Lin / Chen, Mimi / Huang, Zibao / Tan, Yinfeng / Zhang, Caiyun / Zhang, Shouwen / Zhang, Yong / Zhang, Xiaopo

Journal of ethnopharmacology

2023 Volume 322, Page(s) 117571

Abstract: Ethnopharmacological relevance: Scoparia dulcis has been identified as a significant ethnopharmacological substance in the Li, Zhuang, and Dai ethnic groups of China. Traditional medicine use S. dulcis to treat numerous illnesses, most notably diabetes. ...

Abstract	Ethnopharmacological relevance: Scoparia dulcis has been identified as a significant ethnopharmacological substance in the Li, Zhuang, and Dai ethnic groups of China. Traditional medicine use S. dulcis to treat numerous illnesses, most notably diabetes. The considerable antidiabetic properties of this herbal remedy have been established by several clinical investigations and animal experiments. The islet is the intended target of S. dulcis, although the cause of its activity and mechanism for diabetes treatment is unclear. The diterpenoids from S. dulcis have been shown in the literature to have significant hypoglycemic efficacy and to protect islet cells in vitro. Diterpenoids may be the components of this herbal remedy that preserve islets, but further research is needed. Aim of the study: This study was projected to investigate the new diterpenoid scoparicol E from S. dulcis and examined its islet-protective effect and the potential mechanism both in vitro and in vivo. Methods: The structure of the novel diterpenoid scoparicol E was clarified by employing a wide range of spectroscopic methods. Using CCK-8 tests, cytotoxicity and antiapoptotic activity of scoparicol E were detected. Serum biochemical analysis and pathologic examination were performed to study the protective effect of scoparicol E against islet damage. The specific mechanism of action of scoparicol E was investigated through the mitochondrial membrane potential, Annexin V-FITC flow cytometry, and western blotting. Results: Scoparicol E reduced MLD-STZ-induced hyperglycemia in mice and increased insulin and islet apoptosis. Scoparicol E effectively suppressed the Bax/Bcl-2/Caspase-3 pathway, according to the in vivo western blot investigation. Scoparicol E showed significant antiapoptotic action in vitro. We also showed that scoparicol E might prevent islet cells from dying by inhibiting the Bax/Bcl-2/Caspase-3 pathway. The Annexin V-FITC flow cytometry results revealed that MIN6 cell apoptosis was considerably decreased following scoparicol E intervention, showing anti-islet cell apoptosis action. Furthermore, the Caspase-3-mediated apoptosis pathway depends on cytochrome c and the potential of the mitochondrial membrane. Scoparicol E prevented the release of cytochrome c, restored the mitochondrial membrane potential, and prevented MIN6 cell apoptosis. Conclusion: We demonstrated the new diterpenoid scoparicol E could protect islet cells apoptosis by modulating the Bax/Bcl-2/Caspase-3 pathway.
MeSH term(s)	Mice ; Animals ; Caspase 3/metabolism ; bcl-2-Associated X Protein/metabolism ; Scoparia/metabolism ; Cytochromes c/metabolism ; Proto-Oncogene Proteins c-bcl-2/metabolism ; Islets of Langerhans ; Apoptosis ; Diabetes Mellitus/metabolism ; Diterpenes/pharmacology ; Diterpenes/metabolism
Chemical Substances	Caspase 3 (EC 3.4.22.-) ; bcl-2-Associated X Protein ; Cytochromes c (9007-43-6) ; Proto-Oncogene Proteins c-bcl-2 ; Diterpenes
Language	English
Publishing date	2023-12-15
Publishing country	Ireland
Document type	Journal Article
ZDB-ID	134511-4
ISSN	1872-7573 ; 0378-8741
ISSN (online)	1872-7573
ISSN	0378-8741
DOI	10.1016/j.jep.2023.117571
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Zs.A 1494: Show issues

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Article ; Online: Traditional Chinese medicines (TCMs) with varied meridians (Gui-Jing) differentially alleviate the adverse impact of Coptis chinensis on gut microbiota.

Yang, Yanan / Su, Wenquan / Zang, Chenchen / Tan, Yinfeng / Zhang, Yong / Zhou, Zhi / Lu, Weiying / Wu, Shengxian / Zhang, Xiaopo / Wu, Chongming

Journal of ethnopharmacology

2023 Volume 307, Page(s) 116256

Abstract: Ethnopharmacological relevance: The meridian (GuiJing) theory is a unique theory of traditional Chinese medicine (TCM) which has been guiding the clinical practice of TCM for thousands of years, but physiological foundation of TCM's meridian remains to ... ...

Abstract	Ethnopharmacological relevance: The meridian (GuiJing) theory is a unique theory of traditional Chinese medicine (TCM) which has been guiding the clinical practice of TCM for thousands of years, but physiological foundation of TCM's meridian remains to be clarified. Recent investigations have marked gut microbiota as a key mediator for the pharmacological effects of various TCMs. However, most studies focus on the response of gut microbes to a single drug or formula, the interactive effects of different drugs on gut microbiota are scarcely investigated. Aim of the study: In this work, we evaluated the co-regulatory effects of different TCMs on gut microbiota when they were individually combined with Coptis chinensis (HL), and assessed the relationship between gut microbiota and the GuiJing of TCMs. Materials and methods: Normal C57BL/6 mice were gavaged with HL extract for 14 days to disrupt the gut microbial community. Simultaneously, animals were treated with different TCMs which all possess antimicrobial activity but belong to different meridians. The gut microbiota was analyzed by full-length 16S rRNA gene amplicon sequencing to get a thorough bacterial profile at the species level. Results: Administration of HL dramatically disrupted the gut microbiota and decreased the alpha diversity. Co-administration of different TCMs alleviated the adverse impact of HL on gut microbiota in a meridian-dependent manner. TCMs belonging to Shaoyin meridian moderately shifted the gut microbiota, while TCMs belonging to Taiyin and especially Jueyin meridians remarkably recovered the gut microbial community to the normal status. Decreased Firmicutes (Clostridia and Bacilli) and Actinobacteria (Bifidobacteriales) and increased Proteobacteria (Enterobacteriaceae) were main features of HL-induced gut dysbiosis. TCMs belonging to Shaoyin, Taiyin and Jueyin meridians gradually reversed the abundance of these bacteria to their normal levels. Simultaneously, the promoting effect of HL on beneficial bacteria such as Akkermansia muciniphila and Blautia coccoides was substantially preserved when co-administration of these TCMs, suggesting that co-treatment with these TCMs may reduce the toxicity of HL without deteriorating its beneficial effects. Conclusion: Combination of special TCMs may alleviate the adverse effect of HL on gut microbiota while preserving its beneficial actions. Gut microbiota may be a potential biological indicator of the meridian of TCMs.
MeSH term(s)	Animals ; Mice ; Medicine, Chinese Traditional ; Meridians ; Gastrointestinal Microbiome ; Drugs, Chinese Herbal/pharmacology ; Coptis chinensis ; RNA, Ribosomal, 16S ; Mice, Inbred C57BL ; Bacteria
Chemical Substances	Drugs, Chinese Herbal ; RNA, Ribosomal, 16S
Language	English
Publishing date	2023-02-13
Publishing country	Ireland
Document type	Journal Article
ZDB-ID	134511-4
ISSN	1872-7573 ; 0378-8741
ISSN (online)	1872-7573
ISSN	0378-8741
DOI	10.1016/j.jep.2023.116256
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Zs.A 1494: Show issues

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Article ; Online: Follicular Fluid-Derived Small Extracellular Vesicles Alleviate DHEA-Induced Granulosa Cell Apoptosis by Delivering LINC00092.

Zhou, Zhi / Zhang, Yong / Zhang, Xiaopo / Zhang, Juan / Yi, Guohui / Wan, Bangbei / Li, Yejuan / Lu, Hui / Tan, Can / Lu, Weiying

Reproductive sciences (Thousand Oaks, Calif.)

2023 Volume 30, Issue 10, Page(s) 3092–3102

Abstract: Polycystic ovary syndrome (PCOS) is a perplexing condition in females of reproductive age. Dysplasia of ovarian granulosa cell (GC) is implicated in PCOS. Follicular fluid (FF)-extracellular vesicles (Evs) are important in cell-cell communication during ... ...

Abstract	Polycystic ovary syndrome (PCOS) is a perplexing condition in females of reproductive age. Dysplasia of ovarian granulosa cell (GC) is implicated in PCOS. Follicular fluid (FF)-extracellular vesicles (Evs) are important in cell-cell communication during follicular development. The current study elaborated on the function and mechanism of FF-Evs in the viability and apoptosis of GC cells in PCOS development. Human GC cells KGN were treated with dehydroepiandrosterone (DHEA) to mimic a PCOS-like condition in vitro, which were further co-cultured with the FF-derived Evs (FF-Evs). The FF-Evs treatment significantly reduced DHEA-induced apoptosis of KGN cells while promoting cell viability and migration. The lncRNA microarray analysis showed that FF-Evs mainly deliver LINC00092 into the KGN cells. Knockdown of LINC00092 negated the protective effect of FF-Evs against DHEA-induced damage on KGN cells. Moreover, by performing bioinformatics analyses and biotin-labeled RNA pull-down assay, we found that LINC00092 could bind to the RNA binding protein LIN28B and inhibit its binding to pre-microRNA-18-5p, which allowed biogenesis of pre-miR-18-5p and increased the expression of miR-18b-5p, a miRNA with known alleviating role in PCOS by suppressing the PTEN mRNA. Collectively, the present work demonstrates that FF-Evs can alleviate DHEA-induced GC damage by delivering LINC00092.
MeSH term(s)	Female ; Humans ; Polycystic Ovary Syndrome/metabolism ; Follicular Fluid/metabolism ; MicroRNAs/metabolism ; Granulosa Cells/metabolism ; Apoptosis ; Dehydroepiandrosterone/pharmacology ; Extracellular Vesicles/metabolism ; Cell Proliferation
Chemical Substances	MicroRNAs ; Dehydroepiandrosterone (459AG36T1B) ; MIRN18 microRNA, human
Language	English
Publishing date	2023-05-15
Publishing country	United States
Document type	Journal Article
ZDB-ID	2276411-2
ISSN	1933-7205 ; 1933-7191
ISSN (online)	1933-7205
ISSN	1933-7191
DOI	10.1007/s43032-023-01251-7
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Article ; Online: LINC00092 derived from follicular fluid alleviated the symptoms of PCOS through inactivation of phosphatase and tensin homolog by recruiting KDM5A.

Zhou, Zhi / Zhang, Xiaopo / Yi, Guohui / Zhang, Yong / Zhang, Juan / Tan, Can / Wan, Bangbei / Li, Yejuan / Lu, Hui / Lu, Weiying

Reproductive biology

2023 Volume 23, Issue 2, Page(s) 100764

Abstract: Mounting literatures suggest that follicular fluid-derived exosomes (FF-Evs) influence the progression of progression of polycystic ovary syndrome (PCOS). The present study was designed to dissect the underlying mechanisms by which FF-Evs affect the PCOS. ...

Abstract	Mounting literatures suggest that follicular fluid-derived exosomes (FF-Evs) influence the progression of progression of polycystic ovary syndrome (PCOS). The present study was designed to dissect the underlying mechanisms by which FF-Evs affect the PCOS. A rat model of PCOS was established using Letrozole induction. After treatment with FF-Evs, rats were examined for alterations in hormones, blood glucose, and lipid levels in serum, oestrus cycle, pathology in the ovaries, and apoptosis of ovarian cells. The functional rescue assays were performed to analyze the impact of long non-coding RNA 00092 (LINC00092) on PCOS rats. The cis-regulatory elements involved in the regulation of phosphatase and tensin homolog (PTEN) expression were analyzed using bioinformatic analysis, followed by verification of the mechanism. FF-Evs treatment ameliorated Letrozole-induced enhancement of weight, insulin resistance, dyslipidemia, and LH/FSH ratio, reduction of luteal cells, granulosa cells, and healthy follicles, prolonged oestrus, oestrous cycle arrest, ovarian tissue fibrosis, and ovarian cell apoptosis in rats, which were counteracted by treatment with shRNA targeting LINC00092. Regarding the mechanism, FF-Evs augmented LINC00092 expression in rats. LINC00092 bound to lysine demethylase 5 A (KDM5A), and KDM5A facilitated the demethylation of H3K4me3 to restrain the transcriptional activity of PTEN. Taken together, FF-Evs delivered LINC00092 repressed the transcriptional activity of PTEN by binding to KDM5A to enhance demethylation of H3K4me3, thereby reducing apoptosis in ovarian cells and alleviating PCOS symptoms.
MeSH term(s)	Animals ; Female ; Rats ; Follicular Fluid/metabolism ; Letrozole/metabolism ; Polycystic Ovary Syndrome/metabolism ; Retinoblastoma-Binding Protein 2/metabolism ; RNA, Long Noncoding/genetics ; RNA, Long Noncoding/metabolism ; Tensins/metabolism
Chemical Substances	KDM5A protein, human (EC 1.14.11.-) ; Letrozole (7LKK855W8I) ; Retinoblastoma-Binding Protein 2 (EC 1.14.11.27) ; RNA, Long Noncoding ; Tensins ; Pten protein, rat (EC 3.1.3.67)
Language	English
Publishing date	2023-04-19
Publishing country	Poland
Document type	Journal Article
ZDB-ID	2189316-0
ISSN	2300-732X ; 1642-431X
ISSN (online)	2300-732X
ISSN	1642-431X
DOI	10.1016/j.repbio.2023.100764
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Zs.A 6095: Show issues

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Article ; Online: The long non-coding RNA BBOX1 antisense RNA 1 is upregulated in polycystic ovary syndrome (PCOS) and suppresses the role of microRNA-19b in the proliferation of ovarian granulose cells : Short title: BBOX1 antisense RNA 1 in cell proliferation.

Zhou, Zhi / Zhang, Yong / Tan, Can / Zhang, Juan / Yi, Guohui / Wang, Bangbei / Li, Yejuan / Lu, Hui / Lu, Weiying / Zhang, Xiaopo

BMC women's health

2023 Volume 23, Issue 1, Page(s) 508

Abstract: Background: MicroRNA-19b (miR-19b) has been reported to be downregulated in polycystic ovary syndrome (PCOS), while its upstream regulators are unclear. We speculated that miR-19b could potentially form a binding relationship with BBOX1 antisense RNA 1 ( ...

Abstract	Background: MicroRNA-19b (miR-19b) has been reported to be downregulated in polycystic ovary syndrome (PCOS), while its upstream regulators are unclear. We speculated that miR-19b could potentially form a binding relationship with BBOX1 antisense RNA 1 (BBOX1-AS1), a long non-coding RNA recognized for its critical role in ovarian cancer. Subsequently, we investigated into their interaction in PCOS. Methods: The expression of miR-19b and BBOX1-AS1 in follicular fluid from both control women (n = 80) and women with PCOS (n = 80) was detected by RT-qPCR. Correlations were analyzed with Pearson' correlation coefficient. The binding of miR-19b to the wild-type (-wt) ad mutant (-mut) BBOX1-AS1 was determined by RNA-RNA pulldown assay. Their interactions were detected by overexpression assay. Bromodeoxyuridine (BrdU) assay was applied for proliferation analysis. Results: BBOX1-AS1 was highly upregulated, while miR-19b was downregulated in PCOS. There was no close correlation across PCOS and the control samples. Consistently, they did not regulate the expression of each other in granulosa cells. However, BBOX1-AS1-wt, but not BBOX1-AS1-mut, could directly interact with miR-19b. BBOX1-AS1 suppressed the role of miR-19b in inhibiting granulosa cell proliferation. Conclusion: BBOX1-AS1 is highly upregulated in PCOS, and it may serve as an endogenous competing RNA for miR-19b to suppress its role in inhibiting granulosa cell proliferation. Our study suggested the role of BBOX1-AS1 as a potential target to treat PCOS.
MeSH term(s)	Female ; Humans ; Cell Proliferation ; Granulosa Cells ; MicroRNAs/genetics ; Polycystic Ovary Syndrome/genetics ; RNA, Long Noncoding/genetics
Chemical Substances	granulose (54577-56-9) ; MicroRNAs ; RNA, Long Noncoding ; BBOX1 protein, human (EC 1.14.11.1)
Language	English
Publishing date	2023-09-21
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2050444-5
ISSN	1472-6874 ; 1472-6874
ISSN (online)	1472-6874
ISSN	1472-6874
DOI	10.1186/s12905-023-02632-5
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Article ; Online: New aphidicolane diterpenoids with glucose consumption promoting and cell viability enhancing activities from Scoparia dulcis.

Dong, Lin / Chen, Mimi / Huang, Zibao / Cao, Mingyu / Zhang, Yong / Sun, Wanying / Liu, Chenpeng / Zhang, Caiyun / Zhang, Shouwen / Zhang, Xiaopo

Fitoterapia

2023 Volume 166, Page(s) 105438

Abstract: Two new aphidicolane diterpenoids, termed Scopadulinol A (1) and B (2), were obtained from whole plants of Scoparia dulcis. Their structures were elucidated by applying various spectroscopic techniques, including 1D- and 2D-NMR and HR-ESI-MS. The ... ...

Abstract	Two new aphidicolane diterpenoids, termed Scopadulinol A (1) and B (2), were obtained from whole plants of Scoparia dulcis. Their structures were elucidated by applying various spectroscopic techniques, including 1D- and 2D-NMR and HR-ESI-MS. The absolute configurations of 1 and 2 were determined by applying the calculated electronic circular dichroism (ECD). In addition, both compounds were tested for their effects on glucose consumption in HL-7702 cells and on palmitic acid (PA) induced viability in MIN6 cells at different concentrations. The results showed that they significantly promoted glucose consumption and attenuated the PA-induced decrease of cell viability. Additionally, 2 was tested to determine whether it could activate AMP-activated protein kinase (AMPK), but it showed no such effect at the tested dosage. These results indicated that the new compounds might promote glucose consumption through other pathways but not by activating AMPK. Collectively, we highlighted the isolation of two new aphidicolane diterpenoids from S. dulcis and found that they could promote glucose consumption and attenuate PA-induced decrease of cell viability.
MeSH term(s)	Glucose ; Scoparia/chemistry ; Cell Survival ; AMP-Activated Protein Kinases ; Molecular Structure ; Diterpenes/pharmacology ; Diterpenes/chemistry
Chemical Substances	Glucose (IY9XDZ35W2) ; AMP-Activated Protein Kinases (EC 2.7.11.31) ; Diterpenes
Language	English
Publishing date	2023-01-27
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	412385-2
ISSN	1873-6971 ; 0367-326X
ISSN (online)	1873-6971
ISSN	0367-326X
DOI	10.1016/j.fitote.2023.105438
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