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Flavonoids from Camellia oleifera flower ameliorate type 2 diabetes mellitus by regulating the p53 pathway 油茶花中的黄酮类化合物通过调节 p53 通路改善 2 型糖尿病。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-18 DOI: 10.1016/j.fitote.2024.106267
Ruining Yu , Dier Shi , Qi Ru , Qiuping Chen , Jianfu Shen

Background

Camellia oleifera flower (COF) is rich in flavonoids and polyphenols, strongly preventing postprandial hyperglycemia and improving diabetes. However, research on the effective ingredients in COF extracts that have hypoglycemic effects is limited, and the mechanism by which COF extracts improve liver insulin resistance and glucose and lipid metabolism still needs to be clarified, requiring further investigation.

Aim

To systematically clarify the role of COF extracts in improving insulin resistance in diabetes mice and to explore their key targets and mechanisms in anti-type 2 diabetes (T2DM).

Materials and methods

Ultrafiltration combined with liquid chromatography-mass spectrometry (UPLC-Q-MS) was used to analyze α-glucosidase inhibitors in COF extracts qualitatively. Blood glucose, lipid, oxidative stress, and liver function indicators were detected in the db/db type 2 diabetes mouse model. Then, RNA-seq was used to identify differentially expressed mRNAs (DEGs) in the liver, screen for key genes and metabolic pathways, and validate the results' accuracy through qPCR experiments.

Results

17 α-glucosidase inhibitors were identified as flavonoids from COF. Through db/db type 2 diabetes mouse model, it was indicated that COF could significantly improve symptoms of hyperglycemia and hyperlipidemia, alleviate oxidative stress, and protect liver and pancreatic tissues by regulating key differential genes expressed, including Nek2, Cdk1, Ccnb1, and Ccnb2 via the p53 signaling pathway and ameliorate the insulin resistance effect.

Conclusion

This study demonstrated the anti-diabetic effect of COF, explored its potential hypoglycemic target, and provided data support for future T2DM prevention and drug treatment.
背景:油茶花(COF)富含黄酮类化合物和多酚类物质,可有效预防餐后高血糖,改善糖尿病。目的:系统阐明COF提取物在改善糖尿病小鼠胰岛素抵抗中的作用,探讨其在抗2型糖尿病(T2DM)中的关键靶点和机制:超滤结合液相色谱-质谱法(UPLC-Q-MS)定性分析 COF 提取物中的α-葡萄糖苷酶抑制剂。检测了 db/db 2 型糖尿病小鼠模型的血糖、血脂、氧化应激和肝功能指标。然后,利用 RNA-seq 鉴定肝脏中差异表达的 mRNA(DEGs),筛选关键基因和代谢通路,并通过 qPCR 实验验证结果的准确性:结果:从COF中鉴定出17种α-葡萄糖苷酶抑制剂为黄酮类化合物。通过 db/db 2 型糖尿病小鼠模型,表明 COF 可通过 p53 信号通路调节 Nek2、Cdk1、Ccnb1 和 Ccnb2 等关键差异基因的表达,显著改善高血糖和高脂血症症状,减轻氧化应激,保护肝脏和胰腺组织,并改善胰岛素抵抗效应:本研究证明了 COF 的抗糖尿病作用,探索了其潜在的降血糖靶点,为未来 T2DM 的预防和药物治疗提供了数据支持。
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引用次数: 0
Pulsatilla suppository prevents recurrent vulvovaginal candidiasis in a rat model via the TLR/MyD88/NLRP3 signaling pathway 白头翁栓通过TLR/MyD88/NLRP3信号通路预防大鼠模型中复发性外阴阴道念珠菌病。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-18 DOI: 10.1016/j.fitote.2024.106250
Hao Zhang , Can Li , Hui Wu , Ziyi Li , Daqiang Wu , Jing Shao , Tianming Wang , Changzhong Wang
Fungal infection caused by Candida albicans is a serious health problem, and as drug resistance worsens, new sources for therapeutic compounds are needed. Traditional Chinese medicine represents a wealth of such sources, and can be designed as suppositories for the treatment of recurrent vulvovaginal candidiasis (RVVC). This study aimed to develop a Pulsatilla suppository containing the n-butanol extract of Pulsatilla decoction (BEPD) to treat RVVC. A Pulsatilla suppository containing BEPD was prepared, and its performance, weight, drug content, dissolution time and percentage, stability, toxicology, and pharmacodynamics were evaluated. Biological compatibility tests and clinical evaluations were performed in female Sprague–Dawley rats. The Pulsatilla suppository melted completely within 30 min. In vitro anti-C. albicans activity, stability changes, and toxicology tests indicated stability and safety in the rats. Compared with RVVC model rats, high-dose BEPD suppository (40, 60 mg/kg) can significantly reduce the vaginal fungal load of rats, relieve neutrophil infiltration, reduce the content of TLR/MyD88 pathway-related proteins, and reduce the expression of inflammatory factors such as NLRP3, demonstrating the efficacy of the Pulsatilla suppository in RVVC.
由白色念珠菌引起的真菌感染是一个严重的健康问题,随着耐药性的加剧,我们需要新的治疗化合物来源。传统中药中蕴含着丰富的此类化合物,可设计成栓剂用于治疗复发性外阴阴道念珠菌病(RVVC)。本研究旨在开发一种含有正丁醇提取物(BEPD)的白头翁栓剂,用于治疗复发性外阴阴道念珠菌病。研究人员制备了含有 BEPD 的白头翁栓剂,并对其性能、重量、药物含量、溶解时间和百分比、稳定性、毒理学和药效学进行了评估。在雌性 Sprague-Dawley 大鼠身上进行了生物相容性测试和临床评估。白头翁栓剂在 30 分钟内完全融化。体外抗白球菌活性、稳定性变化和毒理学测试表明,该药物在大鼠体内具有稳定性和安全性。与 RVVC 模型大鼠相比,大剂量 BEPD 栓剂(40、60 毫克/千克)能显著减少大鼠阴道真菌负荷,缓解中性粒细胞浸润,降低 TLR/MyD88 通路相关蛋白的含量,减少 NLRP3 等炎症因子的表达,证明了白头翁栓剂对 RVVC 的疗效。
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引用次数: 0
Aculeaquamides B and C, two new paraherquamides from the co-culture of Aspergillus aculeatinus WHUF0198 and Penicillium sp. DM27 Aculeaquamides B 和 C,两种新的对位喹酰胺,来自黑曲霉 WHUF0198 和青霉 DM27 的共培养。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-18 DOI: 10.1016/j.fitote.2024.106251
Philomina Panin Edjah , Mao-Fang Lu , Wei-Chen Chen , Jun Wu , Yu-Ting Zhong , Mu Li , Qi Chen , Kong-Kai Zhu , Rui-Ying Yuan , Wei-Xin Tao , Ke-Jia Wu , You-Sheng Cai
Two new paraherquamides (PHQs) namely aculeaquamides B and C (1 and 2), along with four known PHQs (36), were isolated from the co-culture of marine fungus Aspergillus aculeatinus WHUF0198 and mangrove-associated fungus Penicillium sp. DM27. Compound 1 represents the first PHQ derivative featuring an uncommon 7/6/5/5/6/5 hexacyclic system. The structures of the isolated compounds were elucidated based on exhaustive NMR spectroscopy measurement and HRESIMS data. The absolute configurations of new compounds were determined by TDDFT-ECD calculations. Compound 3 demonstrated suppression of AngII-induced cardiac hypertrophy while exhibiting relatively low cardiomyocyte toxicity.
从海洋真菌Aspergillus aculeatinus WHUF0198和红树林相关真菌Penicillium sp.DM27的共培养物中分离出两种新的对位喹酰胺(PHQs),即aculeaquamides B和C(1和2),以及四种已知的PHQs(3-6)。化合物 1 是首个 PHQ 衍生物,具有不常见的 7/6/5/5/6/5 六环体系。根据详尽的核磁共振光谱测量和 HRESIMS 数据,阐明了分离化合物的结构。通过 TDDFT-ECD 计算确定了新化合物的绝对构型。化合物 3 抑制了 AngII 诱导的心脏肥大,同时表现出相对较低的心肌细胞毒性。
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引用次数: 0
Herbal drugs in chronic venous disease treatment: An update 慢性静脉疾病治疗中的草药:最新进展。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-16 DOI: 10.1016/j.fitote.2024.106256
Tímea Bencsik , Viktória Lilla Balázs , Ágnes Farkas , Eszter Csikós , Adrienn Horváth , Kamilla Ács , Marianna Kocsis , Martin Doseděl , Silvia Bittner Fialová , Szilvia Czigle , Milan Nagy , Jaroslav Tóth , Michele Protti , Laura Mercolini , Přemysl Mladěnka , József Szentpéteri , Györgyi Horváth
The prevalence of chronic venous disease (CVD) is relatively high, it affects 20–80 % of the population worldwide. CVD may affect any veins in the human body, however, the veins of the lower extremities are the most susceptible to this condition. Among therapeutic possibilities for CVD, mainly chronic venous insufficiency, some medicinal plants (Ruscus aculeatus L., Aesculus hippocastanum L., Centella asiatica (L.) Urb.) and their active compounds (ruscoside, aescin, asiaticoside) or close derivatives also have important places. This review describes shortly the updated knowledge on pathophysiology, clinical manifestations, evaluation, and diagnostics of CVD as well as treatment modalities. The primary focus of this review is on the existing knowledge about botanical medications for treating chronic venous disease (CVD). It covers the chemical makeup of these plant drugs, their pharmacological effects, results from clinical trials involving humans, and any associated safety concerns.
慢性静脉疾病(CVD)的发病率相对较高,全球有 20%-80% 的人患有这种疾病。慢性静脉疾病可能影响人体的任何静脉,但下肢静脉最容易受到影响。在治疗心血管疾病(主要是慢性静脉功能不全)的方法中,一些药用植物(Ruscus aculeatus L.、Aesculus hippocastanum L.、Centella asiatica (L.) Urb.)及其活性化合物(芦荟苷、天麻素、积雪草苷)或近似衍生物也占有重要地位。本综述简要介绍了有关心血管疾病的病理生理学、临床表现、评估和诊断以及治疗方法的最新知识。本综述的主要重点是有关治疗慢性静脉疾病(CVD)的植物药的现有知识。内容包括这些植物药物的化学成分、药理作用、人体临床试验结果以及相关的安全问题。
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引用次数: 0
Six new phenolic glycosides from the roots of Scrophularia ningpoensis 从宁波黄芩根中提取的六种新的酚苷。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-16 DOI: 10.1016/j.fitote.2024.106258
You-Chen Li , Peng Liu , Ying-Ying Su , Chang Xu , Meng Sun , Wei Zhang , Bin Liu
Six new phenolic glycosides (16) and thirteen known compounds (719) were isolated from the roots of Scrophularia ningpoensis. Their structures were determined through comprehensive analyses of the physicochemical properties and spectroscopic data (1D NMR, 2D NMR, and HR-ESI-MS). The anti-inflammatory potential of all compounds was evaluated by determining their ability to inhibit lipopolysaccharide (LPS) induced NO production in RAW 264.7 macrophage cells. In addition, the cytotoxicity of all compounds on HepG2, 4T1 and A549 cell lines was also evaluated.
从宁波黄芩的根中分离出了六种新的酚苷类化合物(1-6)和十三种已知化合物(7-19)。通过对理化性质和光谱数据(一维核磁共振、二维核磁共振和 HR-ESI-MS)的综合分析,确定了这些化合物的结构。通过测定所有化合物抑制 RAW 264.7 巨噬细胞中脂多糖(LPS)诱导的 NO 生成的能力,评估了它们的抗炎潜力。此外,还评估了所有化合物对 HepG2、4 T1 和 A549 细胞系的细胞毒性。
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引用次数: 0
Hermansones A and B: Bioactive naphthazarin congeners from the European crust fungus Hermanssonia centrifuga Hermansones A 和 B:欧洲结壳真菌 Hermanssonia centrifuga 中具有生物活性的萘甲萘嗪同系物。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-16 DOI: 10.1016/j.fitote.2024.106261
Winnie Chemutai Sum , Sherif S. Ebada , Jackson M. Muema , Harald Kellner , Attila Mándi , Tibor Kurtán , Marc Stadler
Two previously undescribed naphthazarins named hermansones A (1) and B (2), were isolated from the wood-decaying basidiomycete Hermanssonia centrifuga. The study presents the first report of natural products from the species. The structures of the secondary metabolites were elucidated through NMR spectroscopy and mass spectrometry. The absolute configuration of compound 1 was elucidated using TDDFT-ECD calculations. Hermansone B (2) demonstrated moderate inhibitory effects against Chikungunya virus at IC50 of 55.97 μM, without inducing notable cytotoxicity.
研究人员从木材腐朽基枝菌 Hermanssonia centrifuga 中分离出了两种以前未曾描述过的萘噻嗪类化合物,分别命名为 hermansones A (1) 和 B (2)。该研究首次报道了来自该物种的天然产物。通过核磁共振光谱和质谱分析,阐明了次级代谢产物的结构。通过 TDDFT-ECD 计算,阐明了化合物 1 的绝对构型。Hermansone B(2)对基孔肯雅病毒有中等程度的抑制作用,其 IC50 值为 55.97 μM,但不会引起明显的细胞毒性。
{"title":"Hermansones A and B: Bioactive naphthazarin congeners from the European crust fungus Hermanssonia centrifuga","authors":"Winnie Chemutai Sum ,&nbsp;Sherif S. Ebada ,&nbsp;Jackson M. Muema ,&nbsp;Harald Kellner ,&nbsp;Attila Mándi ,&nbsp;Tibor Kurtán ,&nbsp;Marc Stadler","doi":"10.1016/j.fitote.2024.106261","DOIUrl":"10.1016/j.fitote.2024.106261","url":null,"abstract":"<div><div>Two previously undescribed naphthazarins named hermansones A (<strong>1</strong>) and B (<strong>2</strong>), were isolated from the wood-decaying basidiomycete <em>Hermanssonia centrifuga</em>. The study presents the first report of natural products from the species. The structures of the secondary metabolites were elucidated through NMR spectroscopy and mass spectrometry. The absolute configuration of compound <strong>1</strong> was elucidated using TDDFT-ECD calculations. Hermansone B (<strong>2</strong>) demonstrated moderate inhibitory effects against Chikungunya virus at IC<sub>50</sub> of 55.97 μM, without inducing notable cytotoxicity.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"179 ","pages":"Article 106261"},"PeriodicalIF":2.5,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142461355","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Chemical structures of polyketides and alkaloids isolated from a culture of fungus Curvularia moringae 从 Curvularia moringae 真菌培养物中分离出的多酮类化合物和生物碱的化学结构。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-16 DOI: 10.1016/j.fitote.2024.106263
Takahiro Matsumoto , Miho Hamai , Yayako Inui , Tomoe Ohta , Tatsusada Yoshida , Naoto Kojima , Hayato Yoshikawa , Raku Kutose , Shiori Ando , Tetsushi Watanabe
Seven new polyketides [moringols I–VII (17)], a new alkaloid [moringamine I (8)], and seven known compounds (915) were isolated from the fungus Curvularia moringae JKYM-KR4. The planar chemical structures and relative configurations of the new compounds were elucidated by high-resolution mass spectrometry, 1D and 2D NMR spectroscopy, and DP4+ analysis using the calculated 13C NMR chemical shifts. For moringols I and II (1 and 2), the planar chemical structures and relative configurations were confirmed using X-ray crystallography. The absolute configurations of 16 and 8 were determined by ECD calculations. Among the isolated compounds, terpestacin (14) moderately inhibited the proliferation of HT-29 cells.
从真菌 Curvularia moringae JKYM-KR4 中分离出了七种新的多酮类化合物[moringols I-VII (1-7)]、一种新的生物碱[moringamine I (8)]和七种已知化合物(9-15)。新化合物的平面化学结构和相对构型是通过高分辨率质谱、一维和二维核磁共振光谱以及利用计算的 13C 核磁共振化学位移进行 DP4+ 分析而阐明的。对于吗啉醇 I 和 II(1 和 2),其平面化学结构和相对构型已通过 X 射线晶体学得到证实。1-6 和 8 的绝对构型是通过 ECD 计算确定的。在分离出的化合物中,松油醇(14)能中度抑制 HT-29 细胞的增殖。
{"title":"Chemical structures of polyketides and alkaloids isolated from a culture of fungus Curvularia moringae","authors":"Takahiro Matsumoto ,&nbsp;Miho Hamai ,&nbsp;Yayako Inui ,&nbsp;Tomoe Ohta ,&nbsp;Tatsusada Yoshida ,&nbsp;Naoto Kojima ,&nbsp;Hayato Yoshikawa ,&nbsp;Raku Kutose ,&nbsp;Shiori Ando ,&nbsp;Tetsushi Watanabe","doi":"10.1016/j.fitote.2024.106263","DOIUrl":"10.1016/j.fitote.2024.106263","url":null,"abstract":"<div><div>Seven new polyketides [moringols I–VII (<strong>1</strong>–<strong>7</strong>)], a new alkaloid [moringamine I (<strong>8</strong>)], and seven known compounds (<strong>9</strong>–<strong>15</strong>) were isolated from the fungus <em>Curvularia moringae</em> JKYM-KR4. The planar chemical structures and relative configurations of the new compounds were elucidated by high-resolution mass spectrometry, 1D and 2D NMR spectroscopy, and DP4+ analysis using the calculated <sup>13</sup>C NMR chemical shifts. For moringols I and II (<strong>1</strong> and <strong>2</strong>), the planar chemical structures and relative configurations were confirmed using X-ray crystallography. The absolute configurations of <strong>1</strong>–<strong>6</strong> and <strong>8</strong> were determined by ECD calculations. Among the isolated compounds, terpestacin (<strong>14</strong>) moderately inhibited the proliferation of HT-29 cells.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"179 ","pages":"Article 106263"},"PeriodicalIF":2.5,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142461351","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Polyphenols with anti-inflammatory activity isolated from the whole herbs of Delphinium forrestii var. Viride 从蕨类植物 Delphinium forrestii var. Viride 的全草中分离出的具有抗炎活性的多酚
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-15 DOI: 10.1016/j.fitote.2024.106259
Yang Xu , Zhiqi Zhang , Bin Liu , Dejuan Sun , Hua Li , Lixia Chen
Delphinium belongs to Ranunculaceae, which is widely distributed in Northwest China. In folk, this genus of plants has analgesic, anti-inflammatory, and insecticidal effects. By studying non-alkaloid components in the whole herbs of Delphinium forrestii, we obtained a total of 11 compounds (111), including five new (15) and six known polyphenols (611). On the basis of chemical evidences and spectral data analysis (UV, Optical rotation data, 1D/2D-NMR and HR-ESI-MS), the structures of new compounds were elucidated. The inhibitory effect of compounds 111 on lipopolysaccharide (LPS) induced NO production in RAW 264.7 cells was detected. Compounds 4 and 11 showed significant inhibitory effects. This study indicated the presence of compounds with good anti-inflammatory activity among non-alkaloid components in the whole herbs of Delphinium forrestii.
飞燕草属于毛茛科,广泛分布于中国西北地区。在民间,该属植物具有镇痛、消炎、杀虫等作用。通过对地肤子全草中非生物碱类成分的研究,我们共获得了 11 种化合物(1-11),其中包括 5 种新化合物(1-5)和 6 种已知的多酚类化合物(6-11)。根据化学证据和光谱数据分析(紫外光谱、旋光光谱、1D/2D-NMR 和 HR-ESI-MS),阐明了新化合物的结构。检测了化合物 1-11 对 RAW 264.7 细胞中脂多糖(LPS)诱导的 NO 生成的抑制作用。化合物 4 和 11 具有明显的抑制作用。这项研究表明,在苍术全草的非生物碱成分中,存在具有良好抗炎活性的化合物。
{"title":"Polyphenols with anti-inflammatory activity isolated from the whole herbs of Delphinium forrestii var. Viride","authors":"Yang Xu ,&nbsp;Zhiqi Zhang ,&nbsp;Bin Liu ,&nbsp;Dejuan Sun ,&nbsp;Hua Li ,&nbsp;Lixia Chen","doi":"10.1016/j.fitote.2024.106259","DOIUrl":"10.1016/j.fitote.2024.106259","url":null,"abstract":"<div><div><em>Delphinium</em> belongs to Ranunculaceae, which is widely distributed in Northwest China. In folk, this genus of plants has analgesic, anti-inflammatory, and insecticidal effects. By studying non-alkaloid components in the whole herbs of <em>Delphinium forrestii</em>, we obtained a total of 11 compounds (<strong>1</strong>−<strong>11</strong>), including five new (<strong>1</strong>–<strong>5</strong>) and six known polyphenols (<strong>6</strong>–<strong>11</strong>). On the basis of chemical evidences and spectral data analysis (UV, Optical rotation data, 1D/2D-NMR and HR-ESI-MS), the structures of new compounds were elucidated. The inhibitory effect of compounds <strong>1</strong>–<strong>11</strong> on lipopolysaccharide (LPS) induced NO production in RAW 264.7 cells was detected. Compounds <strong>4</strong> and <strong>11</strong> showed significant inhibitory effects. This study indicated the presence of compounds with good anti-inflammatory activity among non-alkaloid components in the whole herbs of <em>Delphinium forrestii</em>.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"179 ","pages":"Article 106259"},"PeriodicalIF":2.5,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142445992","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Sesquiterpenes from the fruits of Piper longum L. and their anti-inflammatory activity 胡椒果实中的倍半萜及其抗炎活性。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-15 DOI: 10.1016/j.fitote.2024.106260
Guanghui Gou , Nannan Xu , Hongliang Li , Jun Li , Haji Akber Aisa
The fruits of Piper longum are called long pepper, which are well-known culinary spice as well as traditional medicine. In present work, thirteen sesquiterpenes including four undescribed compounds were isolated from P. longum fruits. Compound 1 was a rare methylated bisabolane-type sesquiterpene. Compounds (−)-3 and (+)-3 were a pair of enantiomers of an uncommon humulane which were separated by chiral HPLC. The absolute configurations of compounds 13 were confirmed through the means of spectroscopic data analyses, 13C NMR calculations employing DP4+ probability analyses, and ECD calculations. Compounds 2 and 11 presented moderated inhibitory effect on the NO release in LPS-induced RAW264.7 cells with IC50 values of 30.65 ± 0.90 and 38.48 ± 2.42 μM, respectively. Above results enriched the chemical information of P. longum fruits, and meanwhile provided scientific evidences for the anti-inflammatory function of P. longum fruits.
胡椒(Piper longum)的果实被称为长辣椒,是著名的烹饪香料和传统药物。本研究从长胡椒果实中分离出 13 种倍半萜,其中包括 4 种未曾描述过的化合物。化合物 1 是一种罕见的甲基化双苯甲酸酯类倍半萜。化合物(-)-3和(+)-3是一对不常见的葎草烷对映体,通过手性高效液相色谱法进行了分离。化合物 1-3 的绝对构型通过光谱数据分析、采用 DP4+ 概率分析的 13C NMR 计算和 ECD 计算得到了确认。化合物 2 和 11 对 LPS 诱导的 RAW264.7 细胞中的 NO 释放具有适度的抑制作用,IC50 值分别为 30.65 ± 0.90 和 38.48 ± 2.42 μM。以上结果丰富了龙皮果的化学信息,同时为龙皮果的抗炎功能提供了科学依据。
{"title":"Sesquiterpenes from the fruits of Piper longum L. and their anti-inflammatory activity","authors":"Guanghui Gou ,&nbsp;Nannan Xu ,&nbsp;Hongliang Li ,&nbsp;Jun Li ,&nbsp;Haji Akber Aisa","doi":"10.1016/j.fitote.2024.106260","DOIUrl":"10.1016/j.fitote.2024.106260","url":null,"abstract":"<div><div>The fruits of <em>Piper longum</em> are called long pepper, which are well-known culinary spice as well as traditional medicine. In present work, thirteen sesquiterpenes including four undescribed compounds were isolated from <em>P. longum</em> fruits. Compound <strong>1</strong> was a rare methylated bisabolane-type sesquiterpene. Compounds (−)-<strong>3</strong> and (+)-<strong>3</strong> were a pair of enantiomers of an uncommon humulane which were separated by chiral HPLC. The absolute configurations of compounds <strong>1</strong>–<strong>3</strong> were confirmed through the means of spectroscopic data analyses, <sup>13</sup>C NMR calculations employing DP4+ probability analyses, and ECD calculations. Compounds <strong>2</strong> and <strong>11</strong> presented moderated inhibitory effect on the NO release in LPS-induced RAW264.7 cells with IC<sub>50</sub> values of 30.65 ± 0.90 and 38.48 ± 2.42 <em>μ</em>M, respectively. Above results enriched the chemical information of <em>P. longum</em> fruits, and meanwhile provided scientific evidences for the anti-inflammatory function of <em>P. longum</em> fruits.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"179 ","pages":"Article 106260"},"PeriodicalIF":2.5,"publicationDate":"2024-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142461363","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Chemical constituents from the rhizomes of Paris xuefengshanensis 巴黎雪峰山根茎中的化学成分。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-13 DOI: 10.1016/j.fitote.2024.106257
Ying-Li Yang , Xue Bai , Xing-Zhi Yang , Ji-Feng Luo , Xiao-Yan Duan , Dong-Bao Hu , Jun Yang , Yue-Hu Wang
Five new steroidal saponins, xuefengshanosides A–E; one new stilbene trimer, xuefengshansin; and 16 known compounds were isolated from the rhizomes of Paris xuefengshanensis (Melanthiaceae). The chemical structures of the compounds were elucidated by MS and NMR data analyses, ECD calculations, and acidic hydrolysis experiments. The cytotoxicity and antimicrobial activities of the selected compounds were evaluated. Ophiopogonin C′, paris saponin I, paris saponin H, and paris saponin VII showed the most inhibitory activity against five human cancer cell lines and one normal cell line. Xuefengshansin showed weak cytotoxic and antibacterial activities. Paris saponin I was the most active compound against the five tested fungal strains. This species contains structurally diverse compounds that exhibit significant anticancer and antimicrobial activities, suggesting its potential for future development and utilization.
研究人员从巴黎雪峰山(Melanthiaceae)的根茎中分离出了五种新的甾体皂甙(雪峰山苷 A-E)、一种新的链烯三聚体(雪峰山苷)和 16 种已知化合物。通过质谱和核磁共振数据分析、ECD计算和酸性水解实验,阐明了这些化合物的化学结构。对所选化合物的细胞毒性和抗菌活性进行了评估。麦冬皂苷 C'、对位皂苷 I、对位皂苷 H 和对位皂苷 VII 对五种人类癌细胞株和一种正常细胞株的抑制活性最强。雪峰山素的细胞毒性和抗菌活性较弱。巴黎皂苷 I 是对五种受测真菌菌株活性最强的化合物。该物种含有结构多样的化合物,具有显著的抗癌和抗菌活性,表明其具有未来开发和利用的潜力。
{"title":"Chemical constituents from the rhizomes of Paris xuefengshanensis","authors":"Ying-Li Yang ,&nbsp;Xue Bai ,&nbsp;Xing-Zhi Yang ,&nbsp;Ji-Feng Luo ,&nbsp;Xiao-Yan Duan ,&nbsp;Dong-Bao Hu ,&nbsp;Jun Yang ,&nbsp;Yue-Hu Wang","doi":"10.1016/j.fitote.2024.106257","DOIUrl":"10.1016/j.fitote.2024.106257","url":null,"abstract":"<div><div>Five new steroidal saponins, xuefengshanosides A–E; one new stilbene trimer, xuefengshansin; and 16 known compounds were isolated from the rhizomes of <em>Paris xuefengshanensis</em> (Melanthiaceae). The chemical structures of the compounds were elucidated by MS and NMR data analyses, ECD calculations, and acidic hydrolysis experiments. The cytotoxicity and antimicrobial activities of the selected compounds were evaluated. Ophiopogonin C′, paris saponin I, paris saponin H, and paris saponin VII showed the most inhibitory activity against five human cancer cell lines and one normal cell line. Xuefengshansin showed weak cytotoxic and antibacterial activities. Paris saponin I was the most active compound against the five tested fungal strains. This species contains structurally diverse compounds that exhibit significant anticancer and antimicrobial activities, suggesting its potential for future development and utilization.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":"179 ","pages":"Article 106257"},"PeriodicalIF":2.5,"publicationDate":"2024-10-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142461361","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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