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The analysis of raw and processed Polygonatum kingianum saponins and stimulatory mechanism in Caenorhabditis elegans 分析生何首乌皂甙和加工何首乌皂甙对秀丽隐杆线虫的刺激机制
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-05 DOI: 10.1016/j.fitote.2024.106242
Polygonati Rhizoma, a Chinese medicine often used in the clinic, can irritate the tongue and throat, so it must be processed before use. Polygonati Rhizoma contains a variety of chemical components, with saponins being one of the main active ingredients. Saponins can be highly irritating to human mocous membranes and have toxicity. In this study, total saponins were extracted from raw and processed Polygonati Rhizoma and detected by UPLC-Q-TOF-MS to identify their constituents. A total of 46 saponins were detected in TSRPR(total saponins of raw Polygonati Rhizoma), TSSPR(total saponins of steamed Polygonati Rhizoma) and TSWPR(total saponins of Polygonati Rhizoma steamed in wine). Of these, 9 compounds that were present in TSRPR were not detected in TSSPR and TSWPR. C.elegans was used as a model animal to study the neurotoxic effect and its mechanisms. TSRPR was found to have neurotoxic effects on C.elegans, but TSSPR and TSWPR had no adverse effects on the nematodes. The disappearance of the irritant effect of raw Polygonati Rhizoma after processing might be related to the changes in the composition of saponins, and the main reason might be the structural transformation of saponins. In particular, the sugar chains of some highly irritating saponins may have been removed or highly irritating saponins isomerized into weakly irritating saponins. The mechanisms of neurotoxic effects on C.elegans may include upregulation of ced-3 and egl-1 expression to promote apoptosis, damage to GABAergic and cholinergic neurons, downregulation of the GABA transmitter receptor genes ggr-1 and gab-1, and a decrease in glutamate levels that impairs nerve signal transmission.
何首乌是临床常用的中药,会刺激舌头和咽喉,因此使用前必须加工。何首乌含有多种化学成分,其中皂甙是主要活性成分之一。皂苷对人的口腔黏膜有很强的刺激性,并具有毒性。本研究从未加工和加工过的黄精中提取了总皂苷,并通过 UPLC-Q-TOF-MS 进行检测,以确定其中的成分。在 TSRPR(生何首乌总皂苷)、TSSPR(蒸何首乌总皂苷)和 TSWPR(酒蒸何首乌总皂苷)中共检测到 46 种皂苷。其中,TSRPR 中的 9 种化合物在 TSSPR 和 TSWPR 中均未检测到。研究人员使用秀丽隐杆线虫作为模型动物,研究其神经毒性作用及其机制。结果发现,TSRPR 对线虫有神经毒性作用,但 TSSPR 和 TSWPR 对线虫没有不良影响。加工后的生何首乌刺激作用消失可能与皂苷成分的变化有关,主要原因可能是皂苷的结构转变。特别是一些高刺激性皂苷的糖链可能已被去除,或高刺激性皂苷异构化为弱刺激性皂苷。对秀丽隐杆线虫的神经毒性作用机制可能包括上调 ced-3 和 egl-1 的表达以促进细胞凋亡、损伤 GABA 能神经元和胆碱能神经元、下调 GABA 递质受体基因 ggr-1 和 gab-1,以及降低谷氨酸水平以损害神经信号传递。
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引用次数: 0
Germacrane-type sesquiterpenes from Artemisia atrovirens and their anti-inflammatory activity 青蒿中的胚芽烷类倍半萜及其抗炎活性。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-01 DOI: 10.1016/j.fitote.2024.106241
Artemisia plants are well-known for their abundant sesquiterpene compounds, which encompass various structural types and exhibit a range of biological activities. In this study, a systematic investigation of Artemisia atrovirens revealed the presence of germacrane-type sesquiterpenes for the first time. This included the discovery of 10 new compounds and three known analogues, among which were two rare dimeric germacrane-type compounds. Their structures were fully characterized through a comprehensive analysis involving MS, IR, 1D- and 2D-NMR spectroscopic data, single crystal X-ray diffraction, density functional theory (DFT) NMR calculations, and time-dependent DFT electronic circular dichroism (TDDFT ECD) calculations. Furthermore, all isolated compounds were evaluated for their anti-inflammatory activity in LPS-stimulated RAW 264.7 murine macrophages. Compound 10 demonstrated a potent inhibitory effect on NO production, with an IC50 value of 4.01 ± 0.09 μM. This study highlights the diverse chemical repertoire of Artemisia species and underscores their potential in drug discovery and development.
蒿属植物以其丰富的倍半萜化合物而闻名,这些化合物具有多种结构类型,并表现出一系列生物活性。在这项研究中,对青蒿的系统研究首次发现了胚芽蒿类倍半萜化合物。研究发现了 10 种新化合物和 3 种已知类似物,其中包括两种罕见的二聚胚芽萜类化合物。通过涉及质谱、红外光谱、一维和二维核磁共振光谱数据、单晶 X 射线衍射、密度泛函理论(DFT)核磁共振计算和时间相关 DFT 电子圆二色性(TDDFT ECD)计算的综合分析,对这些化合物的结构进行了全面鉴定。此外,还评估了所有分离化合物在 LPS 刺激的 RAW 264.7 鼠巨噬细胞中的抗炎活性。化合物 10 对 NO 的产生具有强效抑制作用,其 IC50 值为 4.01 ± 0.09 μM。这项研究凸显了青蒿物种多样的化学成分,并强调了它们在药物发现和开发方面的潜力。
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引用次数: 0
Six new sesquineolignans from the stems of Akebia quinate and their diacylglycerol acyltransferase activity 琥珀酸赤萍茎中的六种新芝麻素及其二酰甘油酰基转移酶活性。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-09-30 DOI: 10.1016/j.fitote.2024.106221
Six new sesquineolignans (1–6), have been isolated and elucidated from the stems of Akebia quinate together with five known analogues (7–11). Their structures were elucidated on the basis of comprehensive analysis of UV, IR, NMR, HRESIMS and CD spectroscopy experiments. All the isolates were evaluated for in vitro inhibitory activity against DGAT1 and DGAT2. Among them, compounds 1–11 were found to exhibit selective inhibitory activity on DGAT1 with IC50 values ranging from 60.4 ± 1.3 to 84.6 ± 1.3 μM. Besides, the potential binding sites of 1 were predicted by molecular docking.
研究人员从喹乙酸鹰嘴豆(Akebia quinate)的茎中分离并阐明了六种新的芝麻木脂素(1-6)以及五种已知的类似物(7-11)。它们的结构是在紫外光谱、红外光谱、核磁共振、HRESIMS 和 CD 光谱实验综合分析的基础上阐明的。评估了所有分离物对 DGAT1 和 DGAT2 的体外抑制活性。其中,化合物 1-11 对 DGAT1 具有选择性抑制活性,其 IC50 值为 60.4 ± 1.3 至 84.6 ± 1.3 μM。此外,还通过分子对接预测了 1 的潜在结合位点。
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引用次数: 0
Alkaloids in Cancer therapy: Targeting the tumor microenvironment and metastasis signaling pathways 癌症治疗中的生物碱:针对肿瘤微环境和转移信号通路。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-09-27 DOI: 10.1016/j.fitote.2024.106222
The use of phytomedicine in cancer therapy is a growing field of research that takes use of the medicinal properties of plant-derived compounds. Under the domain of cancer therapy and management, alkaloids, a prominent group of natural compounds, have showed significant potential. Alkaloids often affect a wide range of essential cellular mechanisms involved in cancer progression. These multi-targeting capabilities, can give significant advantages to alkaloids in overcoming resistance mechanisms. For example, berberine, an alkaloid found in Berberis species, is widely reported to induce apoptosis by activating caspases and regulating apoptotic pathways. Notably, alkaloids like as quinine have showed promise in inhibiting the formation of new blood vessels required for tumor growth. In addition, alkaloids have shown anti-proliferative and anticancer properties mostly via modulating key signaling pathways involved in metastasis, including those regulating epithelial-mesenchymal transition. This work provides a comprehensive overview of naturally occurring alkaloids that exhibit anticancer properties, with a specific emphasis on their underlying molecular mechanisms of action. Furthermore, many methods to modify previously reported difficult physicochemical properties using nanocarriers in order to enhance its systemic bioavailability have been discussed as well. This study also includes information on newly discovered alkaloids that are now being studied in clinical trials for their potential use in cancer treatment. Further, we have also briefly mentioned on the application of high-throughput screening and molecular dynamics simulation for acceleration on the identification of potent alkaloids based compounds to target and treat cancer.
在癌症治疗中使用植物药是一个不断发展的研究领域,它利用了植物衍生化合物的药用特性。在癌症治疗和管理领域,生物碱作为一类重要的天然化合物,显示出巨大的潜力。生物碱通常会影响癌症发展过程中的多种基本细胞机制。使用这种多靶点方法可能会使生物碱在克服抗药性机制方面具有显著优势。例如,小檗中的生物碱小檗碱可通过激活 Caspases 和调节凋亡途径诱导细胞凋亡。值得注意的是,奎宁等生物碱有望抑制肿瘤生长所需的新血管的形成。此外,生物碱还具有抗增殖和抗癌特性,主要是通过调节参与转移的关键信号通路,包括调节上皮-间质转化的信号通路。本研究全面概述了具有抗癌特性的天然生物碱,并特别强调了其潜在的分子作用机制。此外,还讨论了许多利用纳米载体改变以前报道过的难以使用的理化特性的方法,以提高其全身生物利用度。本研究还介绍了新发现的生物碱,这些生物碱目前正在进行临床试验研究,以确定其在癌症治疗中的潜在用途。此外,我们还简要介绍了高通量筛选和分子动力学模拟在加速鉴定强效生物碱化合物以靶向治疗癌症方面的应用。
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引用次数: 0
Chemical composition and antifungal efficacy of Tunisian Prunus armeniaca L. kernels with formulation of an antidermatophyte cream based on kernel powder 以核仁粉末为基础配制的抗皮肤癣菌霜中的突尼斯杨梅核仁的化学成分和抗真菌功效。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-09-26 DOI: 10.1016/j.fitote.2024.106223
The biological activities of plant products are extremely correlated to the constituents present in each derivate. The present research aims to obtain by gas chromatography, the chemical profile of Prunus armeniaca L. kernel volatile fractions. The evaluation of the in vitro antifungal activities of the sterilized powder and volatile fractions of the plant P. armeniaca L. kernels was performed. Diffusion in a solid medium and broth microdilution methods were applied on fungi with medical importance (dermatophytes, yeasts and Aspergillus spp.). P. armeniaca L. powder based antidermatphyte cream has been formulated. Hydro-distillation generated two volatile fractions (VF1 and VF2) and chromatographic analysis showed the presence of three compounds for VF1 (98.7 % benzaldehyde, 1.0 % benzyl alcohol and 0.3 % 1,8-cineole) and two compounds for VF2 (90.3 % benzaldehyde and 9.3 % benzyl alcohol). The 2.5 % to 5 % concentrations in powder showed antifungal activities against dermatophytic strains. 1.25 to 2 mg/mL concentrations in volatile fractions were efficient against yeast strains, with a better efficiency for the VF1. The creams formulated were stable, cosmetically attractive with satisfactory pH, viscosity and spread ability. Prunus armeniaca L. kernel powders and the cream derived from them exhibit potent antifungal activities. This work presents a simple, ecological and economical means of formulating antifungal active substances and valorizing natural products.
植物产品的生物活性与每种衍生物中的成分密切相关。本研究旨在通过气相色谱法获得杏核挥发性馏分的化学特征。研究人员还对杏仁的灭菌粉末和挥发性馏分的体外抗真菌活性进行了评估。对具有重要医学价值的真菌(皮癣菌、酵母菌和曲霉菌属)采用了固体培养基扩散法和肉汤微量稀释法。已配制出基于 P. armeniaca L. 粉末的抗皮肤病霜。水蒸馏产生了两种挥发性馏分(VF1 和 VF2),色谱分析显示 VF1 含有三种化合物(98.7 % 苯甲醛、1.0 % 苯甲醇和 0.3 % 1,8-蒎烯),VF2 含有两种化合物(90.3 % 苯甲醛和 9.3 % 苯甲醇)。粉末中 2.5 % 至 5 % 的浓度显示了对皮癣菌株的抗真菌活性。挥发性馏分中 1.25 至 2 毫克/毫升的浓度对酵母菌株有效,其中 VF1 的效率更高。配制的膏霜稳定、美观,具有令人满意的 pH 值、粘度和涂抹能力。杏核粉及其制成的膏霜具有很强的抗真菌活性。这项研究提出了一种简单、生态和经济的方法来配制抗真菌活性物质,实现天然产品的价值化。
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引用次数: 0
Meroterpenoids with anti-triple negative breast cancer and antimicrobial activities from Arnebia euchroma Arnebia euchroma 中具有抗三阴性乳腺癌和抗菌活性的 Meroterpenoids。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-09-26 DOI: 10.1016/j.fitote.2024.106234
Two new meroterpenoids, arneuchrols A and B (1 and 2), together with twelve known analogs (314) were isolated from the root of Arnebia euchroma. The structures of 1 and 2 including their absolute configurations were elucidated by NMR, HRESIMS, and DFT calculation of their NMR and ECD data. The structure of pseudoshikonin I, firstly isolated from Lithospermi radix was revised as shikonofuran E (4). Anti-triple negative breast cancer (anti-TNBC) and antimicrobial activities of the isolated compounds were tested. Compounds 3, 4, 6, 7, 9, 10, and 13 exhibited potent inhibitory activity against TNBC (MDA-MB-231 cells) with IC50 values in the range of 0.18–4.58 μM. Compound 10 displayed antifungal activity against five plant pathogenic fungi with MIC values in the range of 6.25–25 μg/mL. Compound 9 exhibited antibacterial activity against Micrococcus lysodeikticus with MIC value of 12.5 μg/mL.
从 Arnebia euchroma 的根中分离出了两种新的 meroterpenoids,arneuchrols A 和 B(1 和 2),以及 12 种已知的类似物(3-14)。通过核磁共振、HRESIMS 以及对其核磁共振和 ECD 数据进行 DFT 计算,阐明了 1 和 2 的结构及其绝对构型。首次从Lithospermi radix中分离出的假莽草素I的结构被修正为莽草呋喃E (4)。对分离出的化合物进行了抗三阴性乳腺癌(anti-TNBC)和抗菌活性测试。化合物 3、4、6、7、9、10 和 13 对 TNBC(MDA-MB-231 细胞)具有很强的抑制活性,IC50 值在 0.18-4.58 μM 之间。化合物 10 对五种植物致病真菌具有抗真菌活性,MIC 值在 6.25-25 μg/mL 之间。化合物 9 对溶血微球菌具有抗菌活性,MIC 值为 12.5 μg/mL。
{"title":"Meroterpenoids with anti-triple negative breast cancer and antimicrobial activities from Arnebia euchroma","authors":"","doi":"10.1016/j.fitote.2024.106234","DOIUrl":"10.1016/j.fitote.2024.106234","url":null,"abstract":"<div><div>Two new meroterpenoids, arneuchrols A and B (<strong>1</strong> and <strong>2</strong>), together with twelve known analogs (<strong>3</strong>–<strong>14</strong>) were isolated from the root of <em>Arnebia euchroma</em>. The structures of <strong>1</strong> and <strong>2</strong> including their absolute configurations were elucidated by NMR, HRESIMS, and DFT calculation of their NMR and ECD data. The structure of pseudoshikonin I, firstly isolated from <em>Lithospermi radix</em> was revised as shikonofuran E (<strong>4</strong>). Anti-triple negative breast cancer (anti-TNBC) and antimicrobial activities of the isolated compounds were tested. Compounds <strong>3</strong>, <strong>4</strong>, <strong>6</strong>, <strong>7</strong>, <strong>9</strong>, <strong>10</strong>, and <strong>13</strong> exhibited potent inhibitory activity against TNBC (MDA-MB-231 cells) with IC<sub>50</sub> values in the range of 0.18–4.58 μM. Compound <strong>10</strong> displayed antifungal activity against five plant pathogenic fungi with MIC values in the range of 6.25–25 μg/mL. Compound <strong>9</strong> exhibited antibacterial activity against <em>Micrococcus lysodeikticus</em> with MIC value of 12.5 μg/mL.</div></div>","PeriodicalId":12147,"journal":{"name":"Fitoterapia","volume":null,"pages":null},"PeriodicalIF":2.5,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142344335","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
The structure elucidation, anti-aging and hypoglycemic effects of an O-acetyl mannoglucan from the bulbs of Lanzhou lily 兰州百合鳞茎中一种 O-乙酰甘露聚糖的结构阐释、抗衰老和降血糖作用。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-09-25 DOI: 10.1016/j.fitote.2024.106240
An O-acetyl mannoglucan (BHP-1) from Lanzhou lily bulbs was structurally elucidated using partial acid hydrolysis, GC–MS, and 2D NMR techniques (COSY, NOESY, HSQC and HMBC) built on prior research, revealing a backbone of -α-D-(1 → 4)-Glcp-β-D-(1 → 4)-Manp- with the most potential side chains -α-D-(1 → 4)-Glcp-β-D-(1 → 4)-Manp-α-D-(1 → 4)-Glcp-α-D-(1 → Glcp- and -α-D-(1 → 4)-Glcp-β-D-(1 → 4)-Manp-α-D-(1 → Glcp-, attached to O-2 and O-3 of glucose and mannose residues, and featuring O-acetyl groups at O-2 or O-3 position of mannose. The terminal residue was α-D-(1 → Glcp. BHP-1 demonstrated anti-aging and hypoglycemic effects, as assessed by C. elegans model and glycolytic enzyme effect in vitro, respectively. The results showed that BHP-1 dose-dependently prolonged lifespan of C. elegans by 33 % at 4 mg/mL under normal conditions, with greater extensions under thermal and oxidative stress (50 % and 80 % increases, respectively, p < 0.05), which were attributed to enhanced antioxidant enzymes (SOD and CAT) and lowered MDA levels of C. elegans. Additionally, BHP-1 exhibited remarkable inhibition on α-glucosidase (93 %) and moderate inhibition on α-amylase (53 %) at 4 mg/mL, with competitive inhibition of α-glucosidase and mixed non-competitive inhibition of α-amylase, respectively. These potential effects might be linked to BHP-1's diverse sugar linkages, higher content of Glc, and certain O-acetyl contents.
在先前研究的基础上,利用部分酸水解、气相色谱-质谱和二维核磁共振技术(COSY、NOESY、HSQC 和 HMBC),对兰州百合球茎中的一种 O-乙酰甘露聚糖(BHP-1)进行了结构阐释、揭示了-α-D-(1 → 4)-Glcp-β-D-(1 → 4)-Manp- 的骨架,其最具潜力的侧链是-α-D-(1 → 4)-Glcp-β-D-(1 → 4)-Manp-α-D-(1 → 4)-Glcp-α-D-(1 → Glcp- 和-α-D-(1 → 4)-Glcp-β-D-(1 → 4)-Manp-α-D-(1 → Glcp-、连接到葡萄糖和甘露糖残基的 O-2 和 O-3,并在甘露糖的 O-2 或 O-3 位具有 O-乙酰基。末端残基为 α-D-(1 → Glcp)。BHP-1具有抗衰老和降血糖的作用,分别通过秀丽隐杆线虫模型和体外糖酵解作用进行评估。结果表明,在正常条件下,4 毫克/毫升的 BHP-1 可使 elegans 的寿命延长 33%,而在热应激和氧化应激条件下,BHP-1 可使 elegans 的寿命延长更多(分别延长 50% 和 80%,p<0.05)。
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引用次数: 0
The synthesis and bioactivity of apigenin derivatives 芹菜素衍生物的合成和生物活性。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-09-25 DOI: 10.1016/j.fitote.2024.106228

Background

Apigenin, a naturally occurring compound with a flavone core structure, is known for its diverse bioactivities, including anti-inflammation, anti-toxicant, anti-cancer and so on. There has been significant interest in the medicinal chemistry community. To address these challenges, researchers have developed various derivatives of apigenin to address challenges such as poor water-solubility and low intestinal absorption, aiming to enhance the pharmacological activities and pharmacokinetic properties of this compound.

Objective

In recent years, there has been a proliferation of apigenin derivatives with enhanced bioactivity. However, there is a lack of comprehensive reviews on the function-based modification of these derivatives. In this paper, we provide an overview of the apigenin derivatives with varying bioactivities and explored their structure activity relationships. And the functions of different groups of apigenin derivatives were also analyzed.

Conclusion

This review summarized the current achievements that could provide some clues for further study of apigenin-based drugs.
背景:芹菜素是一种以黄酮为核心结构的天然化合物,具有抗炎、抗毒、抗癌等多种生物活性。这引起了药物化学界的极大兴趣。针对芹菜素水溶性差、肠道吸收率低等难题,研究人员开发了多种芹菜素衍生物,旨在提高该化合物的药理活性和药代动力学特性:近年来,生物活性更强的芹菜素衍生物层出不穷。目的:近年来,具有增强生物活性的芹菜素衍生物层出不穷,但缺乏对这些衍生物进行基于功能修饰的全面综述。本文概述了具有不同生物活性的芹菜素衍生物,并探讨了它们的结构活性关系。结论:本综述总结了目前所取得的成就,可为进一步研究芹菜苷类药物提供一些线索。
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引用次数: 0
Modification of natural compounds through biotransformation process by microorganisms and their pharmacological properties 微生物通过生物转化过程改变天然化合物及其药理特性。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-09-24 DOI: 10.1016/j.fitote.2024.106227
The biotransformation of natural compounds by fungal microorganisms is a complex biochemical process. Tandem whole-cell biotransformation offers a promising, alternative, and cost-effective method for modifying of bioactive novel compounds. This approach is particularly beneficial for structurally complex natural products that are difficult to be synthesized through traditional synthetic methods. Biotransformation also provides significant regio- and stereoselectivity, making it a valuable tool for the chemical modification of natural compounds. By utilizing microbial conversion reactions, the biological activity and structural diversity of natural products can be enhanced. In this review, we have summarized 282 novel metabolites resulting from microbial transformation by various microorganisms. We discussed the chemical structures and pharmacological properties of these novel biotransformation products. The review would assist scientists working in the fields of biotechnology, organic chemistry, medicinal chemistry, and pharmacology.
真菌微生物对天然化合物的生物转化是一个复杂的生化过程。串联全细胞生物转化为改造具有生物活性的新型化合物提供了一种前景广阔、可供选择且具有成本效益的方法。这种方法尤其适用于难以通过全化学合成方法合成的结构复杂的天然产品。生物转化还具有显著的区域和立体选择性,使其成为天然化合物化学修饰的重要工具。利用微生物转化反应,可以提高天然产物的生物活性和结构多样性。在这篇综述中,我们总结了各种微生物通过微生物转化产生的 282 种新型代谢物。我们讨论了这些新型生物转化产物的化学结构和药理特性。本综述旨在为生物技术、有机化学、药物化学和药理学领域的科学家提供帮助。
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引用次数: 0
Bioactive polyketides and tryptophol alkaloids from the endophytic fungus Botryosphaeria dothidea LE-07 of Chinese tulip tree 中国郁金香树内生真菌 Botryosphaeria dothidea LE-07 的生物活性多酮和色醇生物碱
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-09-24 DOI: 10.1016/j.fitote.2024.106229
Two new tetraketide-derived phenol rhamnosides [botryrhamnosides A (1) and B (2)] and a new rhamnosylated tryptophol alkaloid (botryrhamnoside C, 3), along with seven related known compounds (410) were isolated from the solid culture of Botryosphaeria dothidea LE-07, an endophytic fungus residing in the leaves of the rare medicinal plant Chinese tulip tree (Liriodendron chinense). Their structures with the absolute configurations were determined by a combination of spectroscopy methods, comparing specific rotations, electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. Compounds 1 and 2 are rare tetraketide-derived resorcinols incorporating a l-rhamnose moiety, while 3 represents the first example of rhamnose-bound tryptophol derivatives produced by microorganisms. These metabolites were evaluated in vitro for their antimicrobial and anti-neuroinflammation activities. The rhamnosylated derivatives 15 displayed potent antibacterial activity against Escherichia coli, with MIC values in the range of 8–16 μg/mL. Compound 2 attenuated neuroinflammation in lipopolysaccharide (LPS)-induced BV-2 microglial cells, by decreasing the level of pro-inflammatory mediators [nitric oxide (NO), tumor necrosis factor-α (TNF-α), and interleukin 6 (IL-6)] and down-regulating the mRNA expression of inducible nitric oxide synthase (iNOS). In addition, compound 8 exhibited remarkable inhibitory effect against the ATP-citrate lyase (ACL), an emerging drug target for hyperlipidemia and related glycolipid metabolic disorders, with an IC50 value of 5.32 μM.
研究人员从寄生在珍稀药用植物中国郁金香树(Liriodendron chinense)叶片中的内生真菌 Botryosphaeria dothidea LE-07 的固体培养物中分离出了两种新的四酮类苯酚鼠李糖苷(botryrhamnosides A (1) 和 B (2))和一种新的鼠李糖基化色酚生物碱(botryrhamnoside C, 3),以及七种相关的已知化合物(4-10)。它们的绝对构型结构是通过光谱学方法、比较特定旋转、电子圆二色性(ECD)计算和单晶 X 射线衍射分析相结合确定的。化合物 1 和 2 是罕见的含有鼠李糖分子的四酮衍生间苯二酚,而化合物 3 则是微生物产生的鼠李糖结合色醇衍生物的第一个实例。对这些代谢物的抗菌和抗神经炎症活性进行了体外评估。鼠李糖基化衍生物 1-5 对大肠杆菌具有很强的抗菌活性,MIC 值在 8-16 μg/mL 之间。化合物 2 通过降低促炎介质[一氧化氮(NO)、肿瘤坏死因子-α(TNF-α)和白细胞介素 6(IL-6)]的水平以及下调诱导型一氧化氮合酶(iNOS)的 mRNA 表达,减轻了脂多糖(LPS)诱导的 BV-2 小胶质细胞的神经炎症。此外,化合物 8 对高脂血症和相关糖脂代谢紊乱的新兴药物靶点 ATP 柠檬酸酶(ACL)具有显著的抑制作用,IC50 值为 5.32 μM。
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引用次数: 0
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