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Unleashing the potential: further enhancing the impact of Natural Products and Bioprospecting 释放潜力:进一步加强天然产物和生物勘探的影响。
IF 4.8 3区 化学 Q1 CHEMISTRY, MEDICINAL Pub Date : 2023-08-17 DOI: 10.1007/s13659-023-00388-x
Ji-Kai Liu, Xiao-dong Luo, Ling Zhang, Ying Zhang
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引用次数: 0
Terpenes extracted from marine sponges with antioxidant activity: a systematic review 从海绵中提取具有抗氧化活性的萜烯类化合物的系统综述。
IF 4.8 3区 化学 Q1 CHEMISTRY, MEDICINAL Pub Date : 2023-08-09 DOI: 10.1007/s13659-023-00387-y
Cintia Cristina Santi Martignago, Beatriz Soares-Silva, Julia Risso Parisi, Lais Caroline Souza e Silva, Renata Neves Granito, Alessandra Mussi Ribeiro, Ana Cláudia Muniz Renno, Lorena Ramos Freitas de Sousa, Anna Caroline Campos Aguiar

Marine biodiversity has emerged as a very promising resource of bioactive compounds and secondary metabolites from different sea organisms. The sponge’s secondary metabolites demonstrated various bioactivities and potential pharmacological properties. This systematic review of the literature focuses on the advances achieved in the antioxidant potential of marine sponges in vitro. The review was performed in accordance with PRISMA guidelines. The main inclusion criterion for analysis was articles with identification of compounds from terpene classes that demonstrate antioxidant activity in vitro. Searching in three different databases, two hundred articles were selected. After screening abstracts, titles and evaluating for eligibility of manuscripts 14 articles were included. The most performed analyzes to detect antioxidant activity were scavenging activity 2,2-diphenyl-1-picrylhydrazyl (DPPH) and measurement of intracellular reactive oxygen species (ROS). It was possible to identify 17 compounds of the terpene class with pronounced antioxidant activity in vitro. Scientific evidence of the studies included in this review was accessed by the GRADE analysis. Terpenes play an important ecological role, moreover these molecules have a pharmaceutical and industrial application.

Graphical Abstract

海洋生物多样性已成为不同海洋生物的生物活性化合物和次生代谢物的一个非常有前途的资源。海绵的次生代谢物显示出多种生物活性和潜在的药理特性。本文系统地综述了海绵体外抗氧化潜力的研究进展。审查是按照PRISMA指南进行的。分析的主要纳入标准是具有体外抗氧化活性的萜类化合物鉴定的文章。在三个不同的数据库中检索,选择了200篇文章。在筛选摘要、标题和评估稿件的合格性后,纳入了14篇文章。检测抗氧化活性最常用的方法是清除2,2-二苯基-1-吡啶酰肼(DPPH)活性和测定细胞内活性氧(ROS)。在体外鉴定出17种具有明显抗氧化活性的萜烯类化合物。本综述中纳入的研究的科学证据通过GRADE分析获得。萜烯具有重要的生态作用,而且这些分子具有制药和工业应用。
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引用次数: 0
Four undescribed pyrethrins from seeds of Pyrethrum cinerariifolium and their aphidicidal activity 除虫菊种子中4种未描述的除虫菊酯及其杀虫活性
IF 4.7 3区 化学 Q1 Agricultural and Biological Sciences Pub Date : 2023-07-07 DOI: 10.1007/s13659-023-00385-0
Hao-Ran Zhou, Li-Wu Lin, Zhong-Rong Li, Xing-Rong Peng, Ming-Hua Qiu

Four undescribed pyrethrins C-F (14) as well as four known pyrethrins (58) were isolated from seeds of Pyrethrum cinerariifolium Trev. The structures of compounds 14 were elucidated by UV, HRESIMS, and NMR (1H and 13C NMR, 1H-1H COSY, HSQC, HMBC and ROESY), among which the stereostructure of compound 4 was determined by calculated ECD. Furthermore, compounds 14 were evaluated for their aphidicidal activities. The insecticidal assay results showed that 14 exhibited moderate aphidicidal activities at the concentration of 0.1 mg/mL with the 24 h mortality rates ranging from 10.58 to 52.98%. Among them, pyrethrin D (2) showed the highest aphidicidal activity, with the 24 h mortality rate of 52.98%, which was slightly lower than the positive control (pyrethrin II, 83.52%).

Graphical Abstract

从除虫菊种子中分离到4个未描述的除虫菊酯C-F(1-4)和4个已知的除虫菊酯(5-8)。化合物1 ~ 4的结构通过UV、HRESIMS和NMR (1H和13C NMR、1H-1H COSY、HSQC、HMBC和ROESY)进行了解析,其中化合物4的立体结构通过计算ECD进行了确定。此外,对化合物1 ~ 4的杀蚜活性进行了评价。杀虫试验结果表明,1 ~ 4在浓度为0.1 mg/mL时具有中等杀虫活性,24 h死亡率为10.58% ~ 52.98%。其中,除虫菊酯D(2)的杀虫活性最高,24 h死亡率为52.98%,略低于阳性对照(除虫菊酯II)的83.52%。图形抽象
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引用次数: 0
New halimane and clerodane diterpenoids from Croton cnidophyllus 巴豆刺叶属新盐烷和氯烷二萜
IF 4.7 3区 化学 Q1 Agricultural and Biological Sciences Pub Date : 2023-07-06 DOI: 10.1007/s13659-023-00386-z
Xun Wei, Jia-Luo Huang, Hua-Hua Gao, Fang-Yu Yuan, Gui-Hua Tang, Sheng Yin

Three new halimane furanoditerpenoids (13) and three new clerodane furanoditerpenoids (46), along with seven known terpenoids including four pimarane diterpenoids (710) and three norisoprenoids (1113) were isolated from the 95% EtOH extracts of the plants of Croton cnidophyllus. The 2D structures including absolute configuration of new furanoditerpenoids (16) were elucidated by analysis of their HRMS and NMR data as well as comparison of experimental and calculated ECD curves. Bioassay revealed that two compounds (8 and 9) possessed certain inhibitory effects against NO production stimulated by LPS, with IC50 values of 19.00 ± 1.76 and 21.61 ± 1.11 μM, respectively.

Graphical Abstract

从巴豆95% EtOH提取物中分离得到3个新的卤烷类呋喃二萜(1-3)和3个新的氯烷类呋喃二萜(4-6),以及4个已知的海玛烷类二萜(7-10)和3个异戊二萜(11-13)。通过对新呋喃二萜(1-6)的HRMS和NMR数据的分析,以及实验和计算ECD曲线的比较,确定了它们的二维结构,包括绝对构型。生物实验结果表明,化合物8和9对LPS刺激NO生成具有一定的抑制作用,IC50值分别为19.00±1.76 μM和21.61±1.11 μM。图形抽象
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引用次数: 0
Therapeutic effects of isoquercetin on ovariectomy-induced osteoporosis in mice 异槲皮素对小鼠卵巢切除所致骨质疏松症的治疗作用
IF 4.7 3区 化学 Q1 Agricultural and Biological Sciences Pub Date : 2023-06-08 DOI: 10.1007/s13659-023-00383-2
Mengjing Wu, Mengyu Qin, Xian Wang

Bone marrow mesenchymal stem cells (BMSCs) are non-hematopoietic multipotent stem cells capable of differentiating into mature cells. Isoquercetin, an extract from natural sources, has shown promise as a potential treatment for osteoporosis. To investigate the therapeutic effects of isoquercetin on osteoporosis, bone marrow mesenchymal stem cells (BMSCs) were cultured in vitro, and osteogenesis or adipogenesis was induced in the presence of isoquercetin for 14 days. We evaluated cell viability, osteogenic and adipogenic differentiation, as well as mRNA expression levels of Runx2, Alpl, and OCN in osteoblasts, and mRNA expression levels of Pparγ, Fabp4, and Cebpα in adipocytes. The results showed that isoquercetin dose-dependently increased cell viability and promoted osteogenic differentiation, as evidenced by Alizarin Red and alkaline phosphatase staining and mRNA expression levels of Runx2, Alpl, and OCN in osteoblasts (P < 0.05). In contrast, isoquercetin inhibited adipogenic differentiation and decreased the mRNA expression levels of Pparγ, Fabp4, and Cebpα in adipocytes (P < 0.05). In vivo, isoquercetin treatment increased bone quantity and density in an osteoporosis model mice group, as determined by μCT scanning and immunohistochemistry (P < 0.05). These findings suggest that isoquercetin may have therapeutic potential for osteoporosis by promoting the proliferation and differentiation of BMSCs towards osteoblasts while inhibiting adipogenic differentiation.

Graphical Abstract

骨髓间充质干细胞(BMSCs)是一种能够分化为成熟细胞的非造血多能干细胞。异槲皮素是一种天然提取物,有望成为治疗骨质疏松症的潜在药物。为了研究异槲皮素对骨质疏松症的治疗作用,体外培养骨髓间充质干细胞(BMSCs),并在异槲皮素存在下诱导成骨或脂肪形成14天。我们评估了细胞活力、成骨和脂肪分化,以及成骨细胞中Runx2、Alpl和OCN的mRNA表达水平,以及脂肪细胞中Pparγ、Fabp4和Cebpα的mRNA表达水平。结果显示,异槲皮素剂量依赖性地提高细胞活力,促进成骨分化,茜素红、碱性磷酸酶染色及成骨细胞Runx2、Alpl、OCN mRNA表达水平均证实了异槲皮素的作用(P < 0.05)。相反,异槲皮素抑制脂肪细胞成脂分化,降低脂肪细胞中Pparγ、Fabp4和Cebpα mRNA表达水平(P < 0.05)。在体内,异槲皮素处理增加了骨质疏松模型小鼠组的骨量和骨密度,通过μCT扫描和免疫组化(P < 0.05)。这些发现表明,异槲皮素可能通过促进骨髓间充质干细胞向成骨细胞的增殖和分化,同时抑制成脂分化,从而具有治疗骨质疏松症的潜力。图形抽象
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引用次数: 0
Effects of combined cannabidiol (CBD) and hops (Humulus lupulus) terpene extract treatment on RAW 264.7 macrophage viability and inflammatory markers 大麻二酚(CBD)和啤酒花(Humulus lupulus)萜烯提取物联合处理对RAW 264.7巨噬细胞活力和炎症标志物的影响
IF 4.7 3区 化学 Q1 Agricultural and Biological Sciences Pub Date : 2023-06-07 DOI: 10.1007/s13659-023-00382-3
Inga Dammann, Claudia Keil, Iris Hardewig, Elżbieta Skrzydlewska, Michał Biernacki, Hajo Haase

This study investigates the potential of cannabidiol (CBD), one major cannabinoid of the plant Cannabis sativa, alone and in combination with a terpene-enriched extract from Humulus lupulus (“Hops 1”), on the LPS-response of RAW 264.7 macrophages as an established in vitro model of inflammation. With the present study, we could support earlier findings of the anti-inflammatory potential of CBD, which showed a dose-dependent [0–5 µM] reduction in nitric oxide and tumor necrosis factor-alpha (TNF-α) released by LPS-stimulated RAW 264.7 macrophages. Moreover, we observed an additive anti-inflammatory effect after combined CBD [5 µM] and hops extract [40 µg/mL] treatment. The combination of CBD and Hops 1 showed effects in LPS-stimulated RAW 264.7 cells superior to the single substance treatments and akin to the control hydrocortisone. Furthermore, cellular CBD uptake increased dose-dependently in the presence of terpenes from Hops 1 extract. The anti-inflammatory effect of CBD and its cellular uptake positively correlated with terpene concentration, as indicated by comparison with a hemp extract containing both CBD and terpenes. These findings may contribute to the postulations for the so-called “entourage effect” between cannabinoids and terpenes and support the potential of CBD combined with phytomolecules from a non-cannabinoid source, such as hops, for the treatment of inflammatory diseases.

作为一种已建立的体外炎症模型,本研究探讨了大麻二酚(cannabidiol, CBD)作为植物大麻的主要大麻素之一,单独使用和与葎草(Humulus lupulus)富含萜烯的提取物(“Hops 1”)联合使用对RAW 264.7巨噬细胞lps反应的影响。通过本研究,我们可以支持早期关于CBD抗炎潜力的发现,该发现显示lps刺激的RAW 264.7巨噬细胞释放的一氧化氮和肿瘤坏死因子-α (TNF-α)呈剂量依赖性[0-5µM]降低。此外,我们还观察到CBD[5µM]和啤酒花提取物[40µg/mL]联合处理后的附加抗炎作用。CBD和啤酒花1联合使用对lps刺激的RAW 264.7细胞的影响优于单一物质处理,与对照氢化可的松相似。此外,在啤酒花1提取物中存在萜烯的情况下,细胞对CBD的摄取呈剂量依赖性增加。通过与同时含有CBD和萜烯的大麻提取物进行比较,发现CBD的抗炎作用及其细胞摄取与萜烯浓度呈正相关。这些发现可能有助于大麻素和萜烯之间所谓的“随行效应”的假设,并支持CBD与来自非大麻素来源的植物分子(如啤酒花)结合治疗炎症性疾病的潜力。
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引用次数: 1
Structural characterizations and α-glucosidase inhibitory activities of four Lepidium meyenii polysaccharides with different molecular weights 四种不同分子量麦冬多糖的结构特征及α-葡萄糖苷酶抑制活性
IF 4.7 3区 化学 Q1 Agricultural and Biological Sciences Pub Date : 2023-06-06 DOI: 10.1007/s13659-023-00384-1
Luan Wen, Zhou-Wei Wu, Li-Wu Lin, Abdulbaset Al-Romaima, Xing-Rong Peng, Ming-Hua Qiu

Four polysaccharides (MCPa, MCPb, MCPc, MCPd) were obtained from Lepidium meyenii Walp. Their structures were characterized by chemical and instrumental methods including total sugar, uronic acid and protein content determination, UV, IR and NMR spectroscopy, as well as monosaccharide composition determination and methylation analyses. Four polysaccharides were a group of glucans with different molecular weights ranging from 3.12 to 14.4 kDa, and shared a similar backbone chain consisting of (1→4)-glucose linkages with branches attached to C-3 and C-6. Furthermore, bioactivity assay showed that MCPs had concentration-dependent inhibitory activity on α-glucosidase. MCPb (Mw = 10.1 kDa) and MCPc (Mw = 5.62 kDa) with moderate molecular weights exhibited higher inhibitory activity compared with MCPa and MCPd.

Graphical Abstract

从枸杞中分离得到四种多糖(MCPa、MCPb、MCPc、MCPd)。通过化学和仪器方法对其结构进行了表征,包括总糖、醛酸和蛋白质含量测定、紫外、红外和核磁共振光谱、单糖组成测定和甲基化分析。4种多糖是一组分子量在3.12 ~ 14.4 kDa之间的葡聚糖,它们共享一个相似的主链,由(1→4)-葡萄糖键组成,分支分别连接C-3和C-6。此外,生物活性测定表明,MCPs对α-葡萄糖苷酶具有浓度依赖性的抑制活性。与MCPa和MCPd相比,中等分子量的MCPb (Mw = 10.1 kDa)和MCPc (Mw = 5.62 kDa)表现出更高的抑制活性。图形抽象
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引用次数: 1
New secondary metabolites with cytotoxicity from fungus Penicillium roqueforti 真菌盘古青霉具有细胞毒性的新次生代谢产物
IF 4.7 3区 化学 Q1 Agricultural and Biological Sciences Pub Date : 2023-06-01 DOI: 10.1007/s13659-023-00381-4
Shuyuan Mo, Ziming Zhao, Zi Ye, Zhihong Huang, Yaxin Zhang, Wanqi Yang, Jianping Wang, Zhengxi Hu, Yonghui Zhang

Two novel compounds including a cyclohelminthol type polyketide (namely oxaleimide K, 1) and a maleimide derivative (namely peniroquefortine A, 2), and a new natural product (namely 2-(acetylamino)-N-[(1E)-2-phenylethenyl]-acetamide, 3), together with four known compounds (47), were isolated and identified from fungus Penicillium roqueforti, which was separated from the root soil of Hypericum beanii N. Robson collected from the Shennongjia Forestry District, Hubei Province. Their structures including absolute configurations were mainly established by the NMR spectroscopy analyses and single-crystal X-ray diffraction experiment. Compound 1 represents the second example of a cyclohelminthol type polyketide, which features a rare 6/6/5/5 tetracyclic system and a branched aliphatic chain containing a terminal olefin (oct-1-en-3-yl) moiety, and compound 2 possesses an unprecedented carbon skeleton that is uniquely defined by a maleimide moiety linked to the respective 4-methylene-2-(3-methylbut-2-en-1-yl)-phenol and para-substituted aromatic moieties via the carbon-carbon bonds. Remarkably, the absolute configuration of a cyclohelminthol type polyketide as exemplified by compound 1 is determined by the single-crystal diffraction analysis for the first time, highlighting an E-configuration for the linkage of a succinimide moiety and a tetrahydrofuran moiety for 1 rather than a Z-configuration as previously reported in the biosynthesis study, which gives a new insight into the structural elucidation of this category of polyketides. Additionally, compound 1 exhibited significant cytotoxic activity against multiple tumor cells, especially against the Farage and SU-DHL-2 cells (IC50 < 20 µM, 48 h). Further mechanism study revealed that compound 1 significantly induced cell cycle arrest in Farage and SU-DHL-2 cells by causing abnormal ROS level and triggering oxidative stress.

Graphical Abstract

从湖北神农架林区毛豆金丝桃根土中分离得到环helminthol型聚酮(草酰亚胺K, 1)、马来酰亚胺衍生物(peniroquefortina, 2)、天然产物(2-(乙酰氨基)- n -[(1E)-2-苯基乙烯基]-乙酰胺,3)和4个已知化合物(4-7)。它们的结构包括绝对构型主要通过核磁共振分析和单晶x射线衍射实验确定。化合物1是环甲酚型聚酮的第二个例子,它具有罕见的6/6/5/5四环体系和含有末端烯烃(辛-1-烯-3-基)的支链脂肪链,化合物2具有前所未有的碳骨架,其独特的碳骨架是由马来酰亚胺片段通过碳-碳键连接到各自的4-亚甲基-2-(3-甲基-2-烯-1-基)-苯酚和对取代芳基组成。值得注意的是,以化合物1为例的环helminthol型聚酮的绝对构型首次通过单晶衍射分析确定,突出了1的琥珀酰亚胺片段和四氢呋喃片段的连接为e构型,而不是之前在生物合成研究中报道的z构型,这为该类聚酮的结构解析提供了新的见解。此外,化合物1对多种肿瘤细胞表现出明显的细胞毒活性,特别是对Farage和SU-DHL-2细胞(IC50 < 20µM, 48 h)。进一步的机制研究表明,化合物1通过引起ROS水平异常和引发氧化应激,显著诱导Farage和SU-DHL-2细胞周期阻滞。图形抽象
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引用次数: 1
Correction: Uncarialines A-E, new alkaloids from Uncaria rhynchophylla and their anticoagulant activity 更正:钩藤碱A-E,来自钩藤的新生物碱及其抗凝血活性
IF 4.7 3区 化学 Q1 Agricultural and Biological Sciences Pub Date : 2023-05-12 DOI: 10.1007/s13659-023-00378-z
Ke‑Pu Huang, Li‑Li Xu, Sheng Li, Yin‑Ling Wei, Lian Yang, Xiao‑Jiang Hao, Hong‑Ping He, Yu Zhang
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引用次数: 0
The medicinal chemistry of Urtica dioica L.: from preliminary evidence to clinical studies supporting its neuroprotective activity 荨麻疹的药物化学:从初步证据到支持其神经保护作用的临床研究
IF 4.7 3区 化学 Q1 Agricultural and Biological Sciences Pub Date : 2023-05-12 DOI: 10.1007/s13659-023-00380-5
Prabhakar Semwal, Abdur Rauf, Ahmed Olatunde, Pooja Singh, Mohamed Y. Zaky, Md. Mozahidul Islam, Anees Ahmed Khalil, Abdullah S. M. Aljohani, Waleed Al Abdulmonem, Giovanni Ribaudo

Urtica dioica is a perennial herb from the family of Urticaceae that is commonly known as stinging nettle. This plant is widespread in Europe, Africa, America, and a part of Asia, as it adapts to different environments and climatic conditions. The leaves, stalk, and bark of U. dioica found applications in the field of nutrition, cosmetics, textile, pest control and pharmacology. In this connection, bioactive chemical constituents such as flavonoids, phenolic acids, amino acids, carotenoids, and fatty acids have been isolated from the plant. With this review, we aim at providing an updated and comprehensive overview of the contributions in literature reporting computational, in vitro, pre-clinical and clinical data supporting the therapeutic applications of U. dioica. Experimental evidence shows that U. dioica constituents and extracts can provide neuroprotective effects by acting through a combination of different molecular mechanisms, that are discussed in the review. These findings could lay the basis for the identification and design of more effective tools against neurodegenerative diseases.

Graphical Abstract

荨麻是荨麻科的多年生草本植物,通常被称为荨麻。这种植物广泛分布于欧洲、非洲、美洲和亚洲的部分地区,因为它能适应不同的环境和气候条件。薯蓣的叶、茎、皮在营养、化妆品、纺织、害虫防治和药理等方面都有广泛的应用。在这方面,生物活性化学成分,如黄酮类化合物、酚酸、氨基酸、类胡萝卜素和脂肪酸已经从植物中分离出来。在这篇综述中,我们的目标是提供一个最新的和全面的文献报告的贡献,计算,体外,临床前和临床数据支持杜鹃花的治疗应用。实验证据表明,薯蓣成分及其提取物可能通过多种分子机制的结合发挥神经保护作用,本文将对此进行讨论。这些发现可以为识别和设计更有效的治疗神经退行性疾病的工具奠定基础。图形抽象
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引用次数: 0
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Natural Products and Bioprospecting
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