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A novel diphenylbutenoid-type compound from the rhizomes of Zingiber montanum (J.Koenig) Link ex A.Dietr. (Zingiberaceae) Zingiber montanum (J.Koenig) Link ex A.Dietr.(真菌纲)根茎中的一种新型二苯基丁烯类化合物。
IF 1.9 3区 化学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-09-16 DOI: 10.1080/14786419.2023.2230343
From the EtOAc-soluble extract of the rhizomes of Zingiber montanum (J.Koenig) Link ex A.Dietr., a novel diphenylbutenoid, montadinin A (1) and a previously unreported phenylbutenoid compound, 1-(3,4-dimethoxyphenyl)but-3-en-2-ol (7), in natural source were isolated. Additionally, seven known phenylbutenoids were also identified. The structures of all compounds were elucidated through NMR spectroscopic interpretation. Compounds cis-3-(3,4-dimethoxyphenyl)-4-[(E)-3,4-dimethoxystyryl]cyclohex-1-ene (2), cis-4-[(E)-3,4-dimethoxystyryl]-3-(2,4,5-trimethoxyphenyl)cyclohex-1-ene (3), trans-3-(3,4,-dimethoxyphenyl)-4-[(E)-2,4,5-trimethoxystyryl]cyclohex-1-ene (5), and cis-3-(3,4-dimethoxyphenyl)-4-[(Z)-2,4,5-trimethoxylstyryl]cyclohex-1-ene (6) showed weak cytotoxicity against HepG2 cells with IC50 values of 122.9, 127.3, 257.5, and 168.5 µM, respectively.
从蒙脱宁(Zingiber montanum (J.Koenig) Link ex A.Dietr.)根茎的乙酸乙酯可溶性提取物中分离出了一种新的二苯基类丁烯化合物蒙脱宁 A(1)和一种以前未报道过的天然来源的苯丁烯化合物 1-(3,4-二甲氧基苯基)丁-3-烯-2-醇(7)。此外,还发现了七种已知的苯丁烯化合物。所有化合物的结构都通过核磁共振光谱分析得到了阐明。化合物顺式-3-(3,4-二甲氧基苯基)-4-[(E)-3,4-二甲氧基苯乙烯基]环己-1-烯(2)、顺式-4-[(E)-3,4-二甲氧基苯乙烯基]-3-(2,4,5-三甲氧基苯基)环己-1-烯(3)、反式-3-(3,4,-二甲氧基苯基)-4-[(E)-2、反式-3-(3,4,-二甲氧基苯基)-4-[(E)-2,4,5-三甲氧基苯乙烯基]环己-1-烯 (5)和顺式-3-(3,4-二甲氧基苯基)-4-[(Z)-2,4,5-三甲氧基苯乙烯基]环己-1-烯 (6)对 HepG2 细胞表现出微弱的细胞毒性,IC50 值分别为 122.9、127.3、257.5 和 168.5 µM。
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引用次数: 0
Two new lignan glycosides from Acanthus ilicifoliusL. with their NO inhibition and cytotoxic activity Acanthus ilicifoliusL.的两种新木脂素苷及其 NO 抑制和细胞毒活性。
IF 1.9 3区 化学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-09-16 DOI: 10.1080/14786419.2023.2218009
A phytochemical investigation of the methanolic extract of aerial parts of the Acanthus ilicifolius led to the isolation of two new lignan glycosides, acaniliciosides A and B (1 and 2), together with ten known compounds (3-12). The structures of isolated compounds were elucidated based on HR-ESI-MS, 1D and 2D NMR spectroscopic data. The absolute configurations of two new compounds were established by CD spectra. With the exception of compound 12, other compounds inhibited NO production in LPS activated RAW264.7 cells with IC50 values of 2.14-28.18 µM, as potent as that of the positive control of NG-monomethyl-L-arginine acetate (L-NMMA, IC50 of 32.50 µM). In addition, compounds 5-8 showed cytotoxic effects against SK-LU-1 and HepG2 cell lines with the IC50 values ranging from 16.48 to 76.40 μM compared to the positive control (ellipticine) with the IC50 values ranging from 1.23 to 1.46 μM.
通过对刺桐(Acanthus ilicifolius)气生部分甲醇提取物进行植物化学研究,分离出了两种新的木质素苷--刺桐苷 A 和 B(1 和 2),以及十种已知化合物(3-12)。根据 HR-ESI-MS、一维和二维核磁共振光谱数据,阐明了分离化合物的结构。通过 CD 光谱确定了两种新化合物的绝对构型。除化合物 12 外,其他化合物都能抑制 LPS 激活的 RAW264.7 细胞产生 NO,其 IC50 值为 2.14-28.18 µM,与阳性对照 NG-单甲基-L-精氨酸醋酸酯(L-NMMA,IC50 为 32.50 µM)的抑制效果相当。此外,化合物 5-8 对 SK-LU-1 和 HepG2 细胞株具有细胞毒性作用,其 IC50 值介于 16.48 至 76.40 μM 之间,而阳性对照(鞣花碱)的 IC50 值介于 1.23 至 1.46 μM 之间。
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引用次数: 0
Isolation of Arbortristoside-A from Nyctanthes arbor-tristis seeds and its structural validation by X-ray crystallographic analysis 从 Nyctanthes arbor-tristis 种子中分离出 Arbortristoside-A,并通过 X 射线晶体学分析验证其结构。
IF 1.9 3区 化学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-09-16 DOI: 10.1080/14786419.2023.2228985
Aiming at confirming the chemical structure, herein, we report the crystal structure of Arbortristoside-A, isolated from the seeds of Nyctanthes arbor-tristis Linn. and investigated by single crystal X-ray crystallographic analysis. The unambiguously established structure of Arbortristoside-A not only addresses previously reported structural flaws but also encourages its chemical, computational, and physiological studies as a lead drug candidate of pharmaceutical significance.
为了确认其化学结构,我们在本文中报告了树皮苷-A 的晶体结构,该结构是从 Nyctanthes arbor-tristis Linn.的种子中分离出来的,并通过单晶 X 射线晶体分析进行了研究。明确确定的 Arbortristoside-A 结构不仅解决了之前报道的结构缺陷,还促进了其化学、计算和生理学研究,使其成为具有重要药用价值的候选先导药物。
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引用次数: 0
One new 12, 8-guaianolide sesquiterpene lactone with antihyperglycemic activity from the roots of Cichorium intybus 从 Cichorium intybus 的根中提取出一种具有降血糖活性的新 12,8-guaianolide 倍半萜内酯。
IF 1.9 3区 化学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-09-16 DOI: 10.1080/14786419.2023.2230606
Three 12, 8-guaianolide sesquiterpene lactones, including a new compound intybusin F (1), and a new natural product cichoriolide I (2), along with six known 12, 6-guaianolide compounds (49) were isolated from the roots of Cichorium intybus L. Their structures were determined by extensive spectroscopic analysis. The absolute configurations of new compounds were elucidated based on analysis of the experimental and calculated electronic circular dichroism spectra. Compounds 1, 2, 4, 7, 8 showed significant effects on facilitating the glucose uptake in oleic acid plus high glucose-stimulated HepG2 cells at 50 μM. In addition, compounds 1, 2, 3, 6, 7 exhibited obvious inhibitory effects against NO production, of them, compounds 1, 2, 7 can significantly decrease the secretion of inflammatory cytokines (TNF-α, IL-6 and COX-2) levels in this hyperglycemic HepG2 cell model.
从 Cichorium intybus L 的根中分离出了三种 12,8-guaianolide 倍半萜内酯,包括一种新化合物 intybusin F(1)和一种新天然产物 cichoriolide I(2),以及六种已知的 12,6-guaianolide 化合物(4-9)。根据对实验和计算电子圆二色光谱的分析,阐明了新化合物的绝对构型。化合物 1、2、4、7、8 在 50 μM 的浓度下对油酸加高葡萄糖刺激的 HepG2 细胞的葡萄糖摄取有显著的促进作用。此外,化合物 1、2、3、6、7 对 NO 的产生有明显的抑制作用,其中化合物 1、2、7 能显著降低高血糖 HepG2 细胞模型中炎性细胞因子(TNF-α、IL-6 和 COX-2)的分泌水平。
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引用次数: 0
Angelica sylvestris L. (Apiaceae) of the Isle of Skye (Scotland): chemical composition of essential oil from the aerial flowering parts 斯凯岛(苏格兰)的当归(Angelica sylvestris L., Apiaceae):气生花部分精油的化学成分。
IF 1.9 3区 化学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-09-16 DOI: 10.1080/14786419.2023.2215906
Angelica is a large genus of plants belonging to the Apiaceae family that includes about 100 species of biennial or perennial herbs. Several species of this genus are extensively used in various traditional medicines and, despite their content in toxic furanocoumarins, also as food. In this study, the chemical composition of the essential oil (EO) from aerial flowering parts of Angelica sylvestris L., a plant distributed in Europe, North and Central Asia, collected in the Isle of Skey (Scotland), was analyzed by GC and GC-MS. No one report has been previously published on this accession. The result showed the presence of a large quantity of monoterpene hydrocarbons with limonene (51.89%), by far, as the most abundant component. Other metabolites present in lesser quantity were β-pinene (4.61%), α-pinene (3.54%), and thymol (3.33%). Considerations with respect to all the other EOs of A. sylvestris taxa, studied so far, were carried out.
当归是繖形花科的一大属植物,包括约 100 种二年生或多年生草本植物。该属的一些物种被广泛用于各种传统药物,尽管它们含有有毒的呋喃香豆素,但也被用作食物。本研究采用气相色谱(GC)和气相色谱-质谱(GC-MS)分析了当归(Angelica sylvestris L.,一种分布于欧洲、北亚和中亚的植物,在苏格兰斯基岛采集)气生花部分精油(EO)的化学成分。此前还没有关于该品种的报告。结果表明,该植物含有大量单萜烃,其中柠檬烯(51.89%)是含量最高的成分。其他含量较少的代谢物有 β-蒎烯(4.61%)、α-蒎烯(3.54%)和百里酚(3.33%)。对迄今为止研究过的所有其他鸢尾属植物的环氧乙烷进行了考虑。
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引用次数: 0
Three new furanones from endophytic fungus Hypoxylon vinosopulvinatum DYR-1-7 from Cinnamomum cassia with their antifungal activity 来自肉桂内生真菌 Hypoxylon vinosopulvinatum DYR-1-7 的三种新呋喃酮及其抗真菌活性。
IF 1.9 3区 化学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-09-16 DOI: 10.1080/14786419.2023.2218530
Hypoxylon vinosopulvinatum DYR-1-7 is a endophytic fungus isolated from the Cinnamomum cassia Presl and has an inhibitory effect on Lasiodiplodia pseudotheobromae. Three new furanones, hypoxylonone A-C (1-3), as well as three known compounds (4-6), were isolated from an EtOAc extract of H. vinosopulvinatum DYR-1-7. The structures were determined by spectroscopic data analysis using UV, IR, 1D-, 2D-NMR and HR-ESI-MS. The absolute configurations of 1-3 were elucidated by electronic circular dichroism (ECD) analyses. In the antifungal bioassay, Hypoxylonone B and C exhibited strong inhibitory effects on L. pseudotheobromae with IC50 value at the concentration of 1.01 and 2.40 μg/mL, respectively. Compound 6 showed medium antifungal activity with IC50 value at the concentration of 10.67 μg/mL on Fusarium oxysporum. Compounds 3 and 4 displayed medium antifungul effects on Candida albicans.
Hypoxylon vinosopulvinatum DYR-1-7 是一种从 Cinnamomum cassia Presl 分离出来的内生真菌,对 Lasiodiplodia pseudotheobromae 有抑制作用。从 H. vinosopulvinatum DYR-1-7 的乙酸乙酯提取物中分离出了三种新的呋喃酮,即次黄酮 A-C(1-3)以及三种已知化合物(4-6)。利用紫外光谱、红外光谱、1D-、2D-NMR 和 HR-ESI-MS 进行光谱数据分析,确定了这些化合物的结构。通过电子圆二色性(ECD)分析,阐明了 1-3 的绝对构型。在抗真菌生物测定中,次磺隆酮 B 和 C 对 L. pseudotheobromae 具有很强的抑制作用,IC50 值分别为 1.01 和 2.40 μg/mL。化合物 6 显示出中等的抗真菌活性,其对 Fusarium oxysporum 的 IC50 值为 10.67 μg/mL。化合物 3 和 4 对白色念珠菌的抗真菌效果中等。
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引用次数: 0
Flavonoids from Pistacia chinensis subsp. integerrima with leishmanicidal activity: computational and experimental evidence 具有利什曼杀虫活性的Pistacia chinensis亚种黄酮类化合物:计算和实验证据。
IF 1.9 3区 化学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-09-16 DOI: 10.1080/14786419.2023.2228459
Pistacia chinensis subsp. integerrima is a valuable medicinal plant as its parts and extracts found application for treating diarrhea, fever, liver disorders, asthma, and inflammation. In this study, we report the leishmanicidal activity of sakuranetin, spinacetin, and patuletin extracted from P. chinensis. The tested compounds revealed a strong anti-leishmanial activity in vitro against Leishmania major showing IC50 values of 7.98 ± 0.16 µM, 9.23 ± 0.23 µM 11.09 ± 0.87 µM for sakuranetin, spinacetin, and patuletin, respectively. Moreover, to explore the potential mechanism(s) by which the compounds may act, computational docking studies were performed against dihydrofolate reductase and pteridine reductase, showing that the flavonoids could target these two key enzymes to exploit their leishmanicidal activity. In accordance with in vitro results, patuletin was highlighted as the most promising compound of the set, and binding energy values of −6.72 and −6.74 kcal/mol were computed for the two proteins, respectively.
Pistacia chinensis subsp. integerrima 是一种珍贵的药用植物,其部分和提取物可用于治疗腹泻、发烧、肝脏疾病、哮喘和炎症。在这项研究中,我们报告了从楷属植物中提取的 sakuranetin、spinacetin 和 patuletin 的杀利什曼活性。所测试的化合物在体外对利什曼原虫具有很强的抗利什曼活性,其 IC50 值分别为 7.98 ± 0.16 µM、9.23 ± 0.23 µM 11.09 ± 0.87 µM。此外,为了探索这些化合物的潜在作用机制,还针对二氢叶酸还原酶和蝶啶还原酶进行了计算对接研究,结果表明黄酮类化合物可以针对这两种关键酶来发挥其杀利什曼活性。根据体外实验结果,帕图莱廷被认为是这组化合物中最有潜力的化合物,计算得出这两种蛋白质的结合能值分别为-6.72和-6.74 kcal/mol。
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引用次数: 0
The chemical composition of the aerial parts essential oil of Phagnalon sinaicum collected in the Negev Desert (Israel) 在内盖夫沙漠(以色列)采集的 Phagnalon sinaicum 气生部分精油的化学成分。
IF 1.9 3区 化学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-09-16 DOI: 10.1080/14786419.2023.2230342
The genus Phagnalon Cass. (Asteraceae) is widely distributed from Macaronesia in the West to the Himalayas in the East, from South France and Nord Italy to Ethiopia and Arabian Peninsula. Species of this genus have been used in folk medicine of many countries as medicinal herbs and they are also used such as food. The extracts and the essential oils (EOs) of these plants have reported antimicrobial, antioxidant, antidiabetic, antitumor, etc. properties and they have different biological applications. Phagnalon sinaicum Bornm. and Kneuck. is a very rare plant native of Middle East. It grows primarily in the desert or dry scrubland biome. Its EO, never previously investigated, was analysed by GC-MS. The EO was very rich in oxygenated monoterpenes, with artemisia ketone (20.40%), α-thujone (19.36%), and santolina alcohol (13.29%) as main constituent. Some considerations with respect to all the other EOs of Phagnalon taxa studied so far were carried out.
Phagnalon Cass.属(菊科(菊科)广泛分布于从西部的马卡罗内西亚到东部的喜马拉雅山,从法国南部和意大利北部到埃塞俄比亚和阿拉伯半岛。该属植物在许多国家的民间医药中被用作药材,也被用作食品。据报道,这些植物的提取物和精油(EOs)具有抗菌、抗氧化、抗糖尿病、抗肿瘤等特性,并有不同的生物学应用。Phagnalon sinaicum Bornm.它主要生长在沙漠或干燥的灌木丛生物群落中。以前从未对它的环氧乙烷进行过研究,我们对其进行了气相色谱-质谱(GC-MS)分析。其环氧乙烷富含含氧单萜烯,主要成分为青蒿酮(20.40%)、α-��酮(19.36%)和山茱萸醇(13.29%)。对迄今为止研究过的所有其他法桐类群的环氧乙烷进行了一些考虑。
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引用次数: 0
Synthesis, antifungal activity, and 3d-QSAR study of L-carvone-based pyrazole-oxime ester compounds 基于 L-香芹酮的吡唑-肟酯化合物的合成、抗真菌活性和 3d-QSAR 研究
IF 2.2 3区 化学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-09-16 DOI: 10.1080/14786419.2024.2405016
Xinyan Liu, Wengui Duan, Guishan Lin, Baoyu Li, Yucheng Cui, Zhaolei Zhang, Maofang Yang
Natural products can provide versatile substructures with potential bioactivity and biocompatibility for exploring bioactive compounds. Herein, to explore novel natural product-derived antifungal a...
天然产物可提供具有潜在生物活性和生物相容性的多功能亚结构,用于探索生物活性化合物。在此,为了探索新型天然产物衍生的抗真菌...
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引用次数: 0
Isoryanodane diterpene derivatives from Barringtonia macrocarpa 来自 Barringtonia macrocarpa 的异龙脑二萜衍生物。
IF 1.9 3区 化学 Q3 CHEMISTRY, APPLIED Pub Date : 2024-09-16 DOI: 10.1080/14786419.2023.2217467
From the MeOH residue of Barringtonia macrocarpa branches and leaves, one new isoryanodane diterpene, barringisol (1), and two new isoryanodane diterpene glucosides, barringisosides A and B (2 and 3), were obtained using various chromatographic isolations. The structural characterization was confirmed by spectroscopic methods including 1D, 2D NMR and HR-ESI-QTOF-MS. This is the first isolation of isoryanodane diterpene derivatives from Barringtonia species. Moreover, the in vitro cytotoxicity of 13 on three human cancer cell lines (HepG2, LNCaP and MCF7) was also accessed using SRB assays.
通过不同的色谱分离方法,从 Barringtonia macrocarpa 枝叶的 MeOH 残留物中获得了一种新的异杨烷二萜--barringisol(1)和两种新的异杨烷二萜葡萄糖苷--barringisosides A 和 B(2 和 3)。通过光谱方法(包括一维、二维核磁共振和 HR-ESI-QTOF-MS)确认了其结构特征。这是首次从巴林藤属植物中分离出异紫罗兰烷二萜衍生物。此外,还利用 SRB 检测法研究了 1-3 对三种人类癌细胞株(HepG2、LNCaP 和 MCF7)的体外细胞毒性。
{"title":"Isoryanodane diterpene derivatives from Barringtonia macrocarpa","authors":"","doi":"10.1080/14786419.2023.2217467","DOIUrl":"10.1080/14786419.2023.2217467","url":null,"abstract":"<div><div>From the MeOH residue of <em>Barringtonia macrocarpa</em> branches and leaves, one new isoryanodane diterpene, barringisol (<strong>1</strong>), and two new isoryanodane diterpene glucosides, barringisosides A and B (<strong>2</strong> and <strong>3</strong>), were obtained using various chromatographic isolations. The structural characterization was confirmed by spectroscopic methods including 1D, 2D NMR and HR-ESI-QTOF-MS. This is the first isolation of isoryanodane diterpene derivatives from <em>Barringtonia</em> species. Moreover, the <em>in vitro</em> cytotoxicity of <strong>1</strong>−<strong>3</strong> on three human cancer cell lines (HepG2, LNCaP and MCF7) was also accessed using SRB assays.</div></div>","PeriodicalId":18990,"journal":{"name":"Natural Product Research","volume":null,"pages":null},"PeriodicalIF":1.9,"publicationDate":"2024-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"9540654","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","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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Natural Product Research
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