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Hydroxymethylation hydroxylation of 1,3-diarylpropene through a catalytic diastereoselective Prins reaction: cyclization logic and access to brazilin core 通过催化非对映选择性 Prins 反应对 1,3-二芳基丙烯进行羟甲基化:环化逻辑和获得巴西苷核。
IF 4.8 3区 化学 Q1 CHEMISTRY, MEDICINAL Pub Date : 2024-05-14 DOI: 10.1007/s13659-024-00450-2
Xin-Ting Hu, Qing-Yan Cheng, Yan-Ping Chen, Kun Li, Cai-Xian Yan, Dashan Li, Li-Dong Shao

A catalytic diastereoselective Prins reaction for hydroxymethylation and hydroxylation of 1,3-diarylpropene was successfully utilized to prepare various 1,3-dioxanes 7 in 14–88% yields. Take advantage of the synthetic intermediate 7h, the key B/C rings in brazilin core could be constructed by the sequential of Friedel–Crafts/Ullmann-Ma rather than Ullmann-Ma/Friedel–Crafts reactions.

Graphical Abstract

利用催化非对映选择性 Prins 反应对 1,3-二芳基丙烯进行羟甲基化和羟基化反应,成功制备了各种 1,3-二氧杂环 7,收率为 14-88%。利用合成中间体 7h 的优势,可以通过 Friedel-Crafts/Ullmann-Ma 而不是 Ullmann-Ma/Friedel-Crafts 反应顺序构建巴西苷核中的关键 B/C 环。
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引用次数: 0
Natural-derived acetophenones: chemistry and pharmacological activities 天然萃取的苯乙酮:化学和药理活性。
IF 4.8 3区 化学 Q1 CHEMISTRY, MEDICINAL Pub Date : 2024-05-10 DOI: 10.1007/s13659-024-00447-x
Hamid Ahmadpourmir, Homayoun Attar, Javad Asili, Vahid Soheili, Seyedeh Faezeh Taghizadeh, Abolfazl Shakeri

Acetophenones are naturally occurring phenolic compounds which have found in over 24 plant families and also fungi strains. They are exist in both free or glycosides form in nature. The biological activities of these compounds have been assayed and reported including cytotoxicity, antimicrobial, antimalarial, antioxidant and antityrosinase activities. Herein, we review the chemistry and biological activity of natural acetophenone derivatives that have been isolated and identified until January 2024. Taken together, it was reported 252 acetophenone derivatives in which the genera Melicope (69) and Acronychia (44) were the principal species as producers of acetophenones.

Graphical Abstract

乙酰苯酮类化合物是天然存在的酚类化合物,在超过 24 个植物科和真菌菌株中都有发现。它们在自然界中以游离或苷的形式存在。这些化合物的生物活性已得到检测和报告,包括细胞毒性、抗菌、抗疟、抗氧化和抗酪氨酸酶活性。在此,我们回顾了截至 2024 年 1 月已分离和鉴定的天然苯乙酮衍生物的化学性质和生物活性。总计报告了 252 种苯乙酮衍生物,其中 Melicope 属(69 种)和 Acronychia 属(44 种)是产生苯乙酮的主要物种。
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引用次数: 0
Unveiling the molecular mechanisms: dietary phytosterols as guardians against cardiovascular diseases 揭示分子机制:膳食植物固醇是心血管疾病的守护者。
IF 4.8 3区 化学 Q1 CHEMISTRY, MEDICINAL Pub Date : 2024-05-09 DOI: 10.1007/s13659-024-00451-1
Nasreddine El Omari, Saad Bakrim, Asaad Khalid, Ashraf N. Abdalla, Mohamed A. M. Iesa, Kawtar El Kadri, Siah Ying Tang, Bey Hing Goh, Abdelhakim Bouyahya

Until recently, the main pharmaceuticals used to control cholesterol and prevent cardiovascular disease (CVD) were statin-related drugs, known for their historical side effects. Therefore, there is growing interest in exploring alternatives, such as nutritional and dietary components, that could play a central role in CVD prevention. This review aims to provide a comprehensive understanding of how natural phytosterols found in various diets combat CVDs. We begin with a description of the overall approach, then we explore in detail the different direct and indirect mechanisms that contribute to reducing cardiovascular incidents. Phytosterols, including stigmasterol, β-sitosterol, ergosterol, and fucosterol, emerge as promising molecules within nutritional systems for protection against CVDs due to their beneficial effects at different levels through direct or indirect cellular, subcellular, and molecular mechanisms. Specifically, the mentioned phytosterols exhibit the ability to diminish the generation of various radicals, including hydroperoxides and hydrogen peroxide. They also promote the activation of antioxidant enzymes such as superoxide dismutase, catalase, and glutathione, while inhibiting lipid peroxidation through the activation of Nrf2 and Nrf2/heme oxygenase-1 (HO-1) signaling pathways. Additionally, they demonstrate a significant inhibitory capacity in the generation of pro-inflammatory cytokines, thus playing a crucial role in regulating the inflammatory/immune response by inhibiting the expression of proteins involved in cellular signaling pathways such as JAK3/STAT3 and NF-κB. Moreover, phytosterols play a key role in reducing cholesterol absorption and improving the lipid profile. These compounds can be used as dietary supplements or included in specific diets to aid control cholesterol levels, particularly in individuals suffering from hypercholesterolemia.

Graphical Abstract

直到最近,用于控制胆固醇和预防心血管疾病(CVD)的主要药物都是他汀类药物,这些药物以其历史性的副作用而闻名。因此,人们越来越有兴趣探索可在心血管疾病预防中发挥核心作用的替代品,如营养和膳食成分。本综述旨在全面介绍各种膳食中的天然植物甾醇如何防治心血管疾病。我们首先描述了整体方法,然后详细探讨了有助于减少心血管疾病的不同直接和间接机制。植物甾醇(包括黑甾醇、β-谷甾醇、麦角甾醇和褐藻甾醇)通过直接或间接的细胞、亚细胞和分子机制在不同水平上产生有益影响,因此成为营养系统中很有希望预防心血管疾病的分子。具体来说,上述植物甾醇能够减少各种自由基的生成,包括氢过氧化物和过氧化氢。它们还能促进超氧化物歧化酶、过氧化氢酶和谷胱甘肽等抗氧化酶的活化,同时通过激活 Nrf2 和 Nrf2/血红素加氧酶-1(HO-1)信号通路抑制脂质过氧化。此外,植物固醇还能显著抑制促炎细胞因子的生成,从而通过抑制参与细胞信号通路(如 JAK3/STAT3 和 NF-κB)的蛋白质的表达,在调节炎症/免疫反应方面发挥重要作用。此外,植物甾醇在减少胆固醇吸收和改善血脂状况方面发挥着关键作用。这些化合物可用作膳食补充剂或纳入特定的饮食中,以帮助控制胆固醇水平,尤其是对于患有高胆固醇血症的人。
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引用次数: 0
Antiviral and anti-inflammatory activities of chemical constituents from twigs of Mosla chinensis Maxim Mosla chinensis Maxim 树枝中化学成分的抗病毒和抗炎活性
IF 4.8 3区 化学 Q1 CHEMISTRY, MEDICINAL Pub Date : 2024-05-01 DOI: 10.1007/s13659-024-00448-w
Shi-Yan Feng, Na Jiang, Jia-Ying Yang, Lin-Yao Yang, Jiang-Chao Du, Xuan-Qin Chen, Dan Liu, Rong-Tao Li, Jin-Dong Zhong

Seven undescribed compounds, including three flavones (1–3), one phenylpropanoid (19), three monoaromatic hydrocarbons (27–29), were isolated from the twigs of Mosla chinensis Maxim together with twenty-eight known compounds. The structures were characterized by HRESIMS, 1D and 2D NMR, and ECD spectroscopic techniques. Compound 20 displayed the most significant activity against A/WSN/33/2009 (H1N1) virus (IC50 = 20.47 μM) compared to the positive control oseltamivir (IC50 = 6.85 µM). Further research on the anti-influenza mechanism showed that compound 20 could bind to H1N1 virus surface antigen HA1 and inhibit the early attachment stage of the virus. Furthermore, compounds 9, 22, 23, and 25 displayed moderate inhibitory effects on the NO expression in LPS inducing Raw 264.7 cells with IC50 values of 22.78, 20.47, 27.66, and 30.14 µM, respectively.

Graphical Abstract

从 Mosla chinensis Maxim 的树枝中分离出了 7 种未曾描述过的化合物,包括 3 种黄酮类化合物(1-3)、1 种苯丙类化合物(19)、3 种单芳烃类化合物(27-29),以及 28 种已知化合物。通过 HRESIMS、1D 和 2D NMR 以及 ECD 光谱技术对这些化合物的结构进行了表征。与阳性对照奥司他韦(IC50 = 6.85 µM)相比,化合物 20 对 A/WSN/33/2009 (H1N1) 病毒具有最显著的活性(IC50 = 20.47 µM)。对抗流感机理的进一步研究表明,化合物 20 能与 H1N1 病毒表面抗原 HA1 结合,抑制病毒的早期附着阶段。此外,化合物 9、22、23 和 25 对 LPS 诱导的 Raw 264.7 细胞中的 NO 表达有中度抑制作用,IC50 值分别为 22.78、20.47、27.66 和 30.14 µM。
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引用次数: 0
Scutellarin ameliorates diabetic nephropathy via TGF-β1 signaling pathway 黄芩苷通过 TGF-β1 信号通路改善糖尿病肾病
IF 4.8 3区 化学 Q1 CHEMISTRY, MEDICINAL Pub Date : 2024-04-24 DOI: 10.1007/s13659-024-00446-y
Bangrui Huang, Rui Han, Hong Tan, Wenzhuo Zhu, Yang Li, Fakun Jiang, Chun Xie, Zundan Ren, Rou Shi

Breviscapine, a natural flavonoid mixture derived from the traditional Chinese herb Erigeron breviscapus (Vant.) Hand-Mazz, has demonstrated a promising potential in improving diabetic nephropathy (DN). However, the specific active constituent(s) responsible for its therapeutic effects and the underlying pharmacological mechanisms remain unclear. In this study, we aimed to investigate the impact of scutellarin, a constituent of breviscapine, on streptozotocin-induced diabetic nephropathy and elucidate its pharmacological mechanism(s). Our findings demonstrate that scutellarin effectively ameliorates various features of DN in vivo, including proteinuria, glomerular expansion, mesangial matrix accumulation, renal fibrosis, and podocyte injury. Mechanistically, scutellarin appears to exert its beneficial effects through modulation of the transforming growth factor-β1 (TGF-β1) signaling pathway, as well as its interaction with the extracellular signal-regulated kinase (Erk) and Wnt/β-catenin pathways.

Graphical Abstract

蒲公英是一种天然黄酮类混合物,提取自传统中草药麦冬(Erigeron breviscapus (Vant.) Hand-Mazz),在改善糖尿病肾病(DN)方面具有良好的潜力。然而,导致其治疗效果的特定活性成分及其药理机制仍不清楚。在这项研究中,我们旨在研究黄芩苷(breviscapine 的一种成分)对链脲佐菌素诱导的糖尿病肾病的影响,并阐明其药理机制。我们的研究结果表明,黄芩苷能有效改善体内糖尿病肾病的各种特征,包括蛋白尿、肾小球扩张、系膜基质堆积、肾脏纤维化和荚膜细胞损伤。从机理上讲,黄芩苷似乎是通过调节转化生长因子-β1(TGF-β1)信号通路及其与细胞外信号调节激酶(Erk)和Wnt/β-catenin通路的相互作用来发挥其有益作用的。
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引用次数: 0
Natural compounds proposed for the management of non-alcoholic fatty liver disease 建议用于治疗非酒精性脂肪肝的天然化合物。
IF 4.8 3区 化学 Q1 CHEMISTRY, MEDICINAL Pub Date : 2024-04-01 DOI: 10.1007/s13659-024-00445-z
Théodora Merenda, Florian Juszczak, Elisabeth Ferier, Pierre Duez, Stéphanie Patris, Anne-Émilie Declèves, Amandine Nachtergael

Although non-alcoholic fatty liver disease (NAFLD) presents as an intricate condition characterized by a growing prevalence, the often-recommended lifestyle interventions mostly lack high-level evidence of efficacy and there are currently no effective drugs proposed for this indication. The present review delves into NAFLD pathology, its diverse underlying physiopathological mechanisms and the available in vitro, in vivo, and clinical evidence regarding the use of natural compounds for its management, through three pivotal targets (oxidative stress, cellular inflammation, and insulin resistance). The promising perspectives that natural compounds offer for NAFLD management underscore the need for additional clinical and lifestyle intervention trials. Encouraging further research will contribute to establishing more robust evidence and practical recommendations tailored to patients with varying NAFLD grades.

Graphical Abstract

尽管非酒精性脂肪肝(NAFLD)是一种复杂的疾病,其特点是发病率越来越高,但人们经常推荐的生活方式干预措施大多缺乏高水平的疗效证据,目前也没有针对这一适应症的有效药物。本综述通过三个关键靶点(氧化应激、细胞炎症和胰岛素抵抗),深入探讨了非酒精性脂肪肝的病理、其各种潜在的生理病理机制,以及有关使用天然化合物治疗非酒精性脂肪肝的现有体外、体内和临床证据。天然化合物为非酒精性脂肪肝的治疗提供了广阔的前景,强调了进行更多临床和生活方式干预试验的必要性。鼓励开展进一步的研究,将有助于为非酒精性脂肪肝不同等级的患者提供更有力的证据和实用的建议。
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引用次数: 0
Compounds from Agathis dammara exert hypoglycaemic activity by enhancing glucose uptake: lignans, terpenes and others Agathis dammara 中的化合物通过增强葡萄糖摄取发挥降血糖作用:木酚素、萜烯等。
IF 4.8 3区 化学 Q1 CHEMISTRY, MEDICINAL Pub Date : 2024-03-22 DOI: 10.1007/s13659-024-00440-4
Zhe-Wei Yu, Bang-Ping Cai, Su-Zhi Xie, Yi Zhang, Wen-Hui Wang, Shun-Zhi Liu, Yan-Lin Bin, Qi Chen, Mei-Juan Fang, Rong Qi, Ming-Yu Li, Ying-Kun Qiu

In this study, two new kaurane diterpenes (16, 17), together with 12 lignans (1–12), a triterpene (15), and two other compounds (13, 14) were isolated from the woods of Agathis dammara. The structure of the new compound was determined by HR ESIMS and 1D/2D NMR spectroscopy, and its absolute configuration was determined by electronic circular dichroism (ECD) exciton chirality method. Compounds 5, 11, 14 exhibit significant hypoglycaemic activity in zebrafish, and their mechanism of action is to enhance glucose uptake in zebrafish.

Graphical Abstract

本研究从 Agathis dammara 树林中分离出了两种新的贝壳杉烷二萜(16、17)以及 12 种木脂素(1-12)、一种三萜(15)和两种其他化合物(13、14)。利用 HR ESIMS 和一维/二维核磁共振光谱测定了新化合物的结构,并利用电子圆二色性(ECD)激子手性法测定了其绝对构型。化合物 5、11 和 14 在斑马鱼体内表现出显著的降血糖活性,其作用机制是增强斑马鱼的葡萄糖摄取。
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引用次数: 0
Gastrodinol derivatives and prenylated flavones from the flower branch of Gastrodia elata 从天麻花枝中提取的天麻素衍生物和炔化黄酮类化合物
IF 4.8 3区 化学 Q1 CHEMISTRY, MEDICINAL Pub Date : 2024-03-20 DOI: 10.1007/s13659-024-00430-6
Shi-Hui Qin, Zhi-Lan Li, Liu Yang, Jiang-Miao Hu

Based on the research progress and traditional usage with whole herbal of the TCM "Tianma", chemical studies herein on the flower branch of Gastrodia elata were carried out in-depth and got 13 compounds including the gastrodinols (1–4), the flavonoid morins (5–8, 11–12), together with the specialist mulberrofurans (9, 13) and gastrodiamide (10) for the first time from the species. The antibacterial and cholinesterase inhibitory activities were then evaluated and the results showed that compounds 5, 11, 12, 13 have good activity against anti-methicillin-resistant Staphylococcus aureus, and compounds 9, 13 had good acetylcholinesterase inhibitory activity. All these results provide new chemical composition for better understanding the traditional application of "Tianma" and for exploring new pharmacological ingredients.

Graphical Abstract

根据天麻的研究进展和天麻全草的传统用法,本文对天麻花枝进行了深入的化学研究,首次从天麻中获得了13个化合物,包括天麻素(1-4)、黄酮类吗啉(5-8,11-12)以及专科木鳖子呋喃(9,13)和天麻二酰胺(10)。结果表明,化合物 5、11、12 和 13 对抗耐甲氧西林金黄色葡萄球菌具有良好的活性,化合物 9 和 13 具有良好的乙酰胆碱酯酶抑制活性。所有这些结果为更好地了解 "天麻 "的传统应用和探索新的药理成分提供了新的化学成分。 图文摘要
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引用次数: 0
Which is the optimal choice for neonates’ formula or breast milk? 新生儿配方奶粉和母乳哪个更好?
IF 4.8 3区 化学 Q1 CHEMISTRY, MEDICINAL Pub Date : 2024-03-15 DOI: 10.1007/s13659-024-00444-0
Yueqi Hu, Xing Wu, Li Zhou, Jikai Liu

The incidence of prematurity has been increasing since the twenty-first century. Premature neonates are extremely vulnerable and require a rich supply of nutrients, including carbohydrates, proteins, docosahexaenoic acid (DHA), arachidonic acid (ARA) and others. Typical breast milk serves as the primary source for infants under six months old to provide these nutrients. However, depending on the individual needs of preterm infants, a more diverse and intricate range of nutrients may be necessary. This paper provides a comprehensive review of the current research progress on the physical and chemical properties, biological activity, function, and structure of breast milk, as well as explores the relationship between the main components of milk globular membrane and infant growth. Additionally, compare the nutritional composition of milk from different mammals and newborn milk powder, providing a comprehensive understanding of the differences in milk composition and detailed reference for meeting daily nutritional needs during lactation.

Graphical Abstract

自二十一世纪以来,早产儿的发病率不断上升。早产新生儿极其脆弱,需要丰富的营养物质,包括碳水化合物、蛋白质、二十二碳六烯酸(DHA)、花生四烯酸(ARA)等。一般母乳是为 6 个月以下婴儿提供这些营养素的主要来源。然而,根据早产儿的不同需求,可能需要更多样、更复杂的营养素。本文全面回顾了目前有关母乳的理化性质、生物活性、功能和结构的研究进展,并探讨了母乳球膜的主要成分与婴儿生长之间的关系。此外,还比较了不同哺乳动物的乳汁和新生儿奶粉的营养成分,为人们全面了解乳汁成分的差异,满足哺乳期日常营养需求提供了详细的参考。
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引用次数: 0
3α-Hydroxybufadienolides in Bufo gallbladders: structural insights and biotransformation 蟾蜍胆中的 3α-Hydroxybufadienolides: 结构见解和生物转化。
IF 4.8 3区 化学 Q1 CHEMISTRY, MEDICINAL Pub Date : 2024-03-04 DOI: 10.1007/s13659-024-00442-2
Li-Jun Ruan, Zhi-Jun Song, Ren-Wang Jiang

Bufadienolides, naturally occurring steroids primarily found in toads, have garnered attention for their pharmacological properties and ecological significance. In this study, we isolated and identified 21 bufadienolides from the gallbladders of Bufo gargarizans, comprising four new compounds and 17 known ones. Notably, the predominance of 15 bufadienolides with a 3α-OH configuration in toad bile differs significantly from the 3β-OH bufadienolides found in venom secreted by toad glands. Moreover, our investigation into the biotransformation of 3β-OH and 3α-OH bufadienolides in the liver and kidney tissues of toads revealed an irreversible conversion from 3β-OH to 3α-OH bufadienolides, suggesting a crucial role in toad self-detoxification. These findings provide valuable insights into the structural diversity of bufadienolides and advance our understanding of their medical and ecological significance.

Graphical Abstract

蟾蜍内酯(Bufadienolides)是主要存在于蟾蜍体内的天然类固醇,因其药理特性和生态学意义而备受关注。在这项研究中,我们从蟾蜍的胆囊中分离并鉴定了 21 种 bufadienolides,其中包括 4 种新化合物和 17 种已知化合物。值得注意的是,蟾蜍胆汁中主要含有 15 种 3α-OH 构型的布法迪内酯,这与蟾蜍腺体分泌的毒液中发现的 3β-OH 布法迪内酯有很大不同。此外,我们对 3β-OH 和 3α-OH 布法二烯醇内酯在蟾蜍肝脏和肾脏组织中的生物转化进行了研究,结果发现,3β-OH 布法二烯醇内酯向 3α-OH 布法二烯醇内酯的转化是不可逆的,这表明布法二烯醇内酯在蟾蜍的自我解毒过程中起着至关重要的作用。这些发现为我们了解布法迪烯醇内酯的结构多样性提供了宝贵的视角,并加深了我们对其医疗和生态意义的理解。
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引用次数: 0
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Natural Products and Bioprospecting
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