Journal of Natural Medicines最新文献_第6页

Chemical profile and biological activities of Lysiphyllum binatum (Blanco) de Wit Lysiphyllum binatum (Blanco) de Wit 的化学成分和生物活性。

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-09-25 DOI: 10.1007/s11418-024-01844-9

Surasak Kheawchaum, Sanit Thongnest, Jutatip Boonsombat, Paratchata Batsomboon, Chulabhorn Mahidol, Hunsa Prawat, Somsak Ruchirawat

Lysiphyllum binatum (Blanco) de Wit in the Fabaceae family, despite its traditional medicinal uses, has not been the subject of prior scientific inquiry into its chemical and biological profile. The dichloromethane and MeOH extracts of its roots exhibited notably similar antioxidant activity, while the dichloromethane extract of the vine stems showed aromatase inhibition. This study aimed to identify the bioactive components responsible for these activities. Chemical investigation of the roots led to the isolation of six new metabolites, named lysiphans A–F (1–6), along with eight known compounds (7–14). The vine stem yielded lysiphan C (3) and compound 7, as well as five known isolates (15–19). The structures of these metabolites were determined through NMR spectral analysis, HRESIMS, quantum chemical calculations of NMR and ECD spectra, and Mosher’s modifications to establish their absolute configurations. The biogenetic relationships between the new compounds were proposed. Several of the isolates were evaluated for their antioxidant, anti-aromatase, and cytotoxic properties. Lysiphan B (2) exhibited significant antioxidant activity, with an IC₅₀ value of 28.8 ± 0.4 μM in the diphenyl picrylhydrazyl radical (DPPH) assay, 3.5 ± 0.2 μM in the xanthine/xanthine oxidase (XXO) assay, and 1.5 ± 0.0 ORAC units in oxygen radical absorbance capacity (ORAC) assay. Additionally, compounds 12, 13, and 16 exhibited very strong aromatase inhibitory activity with IC₅₀ values of 0.3 ± 0.2, 4.7 ± 0.1, and 0.9 ± 0.2 µM, respectively. Compound 16 also demonstrated strong ORAC activity of 1.9 ± 0.1 ORAC units.

豆科植物 Lysiphyllum binatum (Blanco) de Wit 尽管具有传统的药用价值，但科学界此前尚未对其化学和生物特性进行研究。其根部的二氯甲烷和甲醇提取物显示出明显相似的抗氧化活性，而藤茎的二氯甲烷提取物则显示出芳香化酶抑制作用。这项研究的目的是确定产生这些活性的生物活性成分。通过对根部进行化学研究，分离出了六种新的代谢物，命名为莱西潘 A-F（1-6），以及八种已知化合物（7-14）。在藤本植物的茎中发现了来苏番 C（3）和化合物 7，以及五种已知的分离物（15-19）。这些代谢物的结构是通过核磁共振光谱分析、HRESIMS、核磁共振和 ECD 光谱的量子化学计算以及 Mosher 修正来确定其绝对构型的。提出了新化合物之间的生物遗传学关系。对几种分离物的抗氧化、抗芳香化酶和细胞毒性特性进行了评估。Lysiphan B（2）具有显著的抗氧化活性，在二苯基吡啶肼自由基（DPPH）测定中的 IC50 值为 28.8 ± 0.4 μM，在黄嘌呤/黄嘌呤氧化酶（XXO）测定中的 IC50 值为 3.5 ± 0.2 μM，在氧自由基吸收能力（ORAC）测定中的 IC50 值为 1.5 ± 0.0 ORAC 单位。此外，化合物 12、13 和 16 表现出极强的芳香化酶抑制活性，IC50 值分别为 0.3 ± 0.2、4.7 ± 0.1 和 0.9 ± 0.2 µM。化合物 16 还具有很强的 ORAC 活性，达到 1.9 ± 0.1 ORAC 单位。

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引用次数: 0

Azamollugin, a mollugin derivative, has inhibitory activity on MyD88- and TRIF-dependent pathways 棉隆素衍生物 Azamollugin 对 MyD88 和 TRIF 依赖性通路具有抑制活性

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-09-16 DOI: 10.1007/s11418-024-01842-x

Yuki Nakajima, Hitomi Nishino, Kazunori Takahashi, Alfarius Eko Nugroho, Yusuke Hirasawa, Toshio Kaneda, Hiroshi Morita

Previously, we reported that azamollugin, an aza-derivative of mollugin, exhibited potent inhibitory activity on NO production in LPS-stimulated RAW 264.7 cells. Further investigations in this study revealed that azamollugin not only suppressed iNOS gene expression regulated by NF-κB, but also inhibited LPS-induced IFN-β expression, which is known to be regulated by IRF3. Azamollugin exhibited an inhibitory activity on LPS-induced IRAK1 activation, suggesting inhibitory effect on the MyD88-dependent pathway. Furthermore, azamollugin inhibited LPS-induced phosphorylation of IRF3 and its upstream factor, TBK1/IKKε, suggesting an inhibitory effect on the TRIF-dependent pathway via TLR4. In addition, azamollugin also suppressed poly(I:C)-induced phosphorylation of TBK1 and IRF3, suggesting an inhibitory effect on the TRIF-dependent pathway via TLR3. These results suggest that azamollugin has inhibitory activity against both the MyD88-dependent and TRIF-dependent pathways, respectively.

摘要以前，我们曾报道过棉隆素的杂环衍生物偶氮棉隆素对LPS刺激的RAW 264.7细胞中NO的产生具有强效抑制活性。本研究的进一步研究发现，氮杂毛蕊花素不仅能抑制受 NF-κB 调控的 iNOS 基因表达，还能抑制 LPS 诱导的 IFN-β 表达，而 IFN-β 是由 IRF3 调控的。棉隆素对 LPS 诱导的 IRAK1 激活有抑制作用，这表明它对 MyD88 依赖性途径有抑制作用。此外，氮卓谷蛋白还能抑制 LPS 诱导的 IRF3 及其上游因子 TBK1/IKKε 的磷酸化，这表明氮卓谷蛋白对通过 TLR4 的 TRIF 依赖性途径有抑制作用。此外，氮杂毛蕊花素还抑制了聚(I:C)诱导的TBK1和IRF3的磷酸化，这表明氮杂毛蕊花素通过TLR3对TRIF依赖性途径有抑制作用。这些结果表明，氮杂毛蕊花素分别对MyD88依赖性途径和TRIF依赖性途径具有抑制活性。图文摘要

引用次数: 0

Macrocyclizing-thioesterases in bacterial non-ribosomal peptide biosynthesis 细菌非核糖体肽生物合成中的大环化硫酯酶。

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-08-30 DOI: 10.1007/s11418-024-01841-y

Kenichi Matsuda

Macrocyclization of peptides reduces conformational flexibilities, potentially leading to improved drug-like properties. However, side reactions such as epimerization and oligomerization often pose synthetic challenges. Peptide-cyclizing biocatalysts in the biosynthesis of non-ribosomal peptides (NRPs) have remarkable potentials as chemoenzymatic tools to facilitate more straightforward access to complex macrocycles. This review highlights the biocatalytic potentials of NRP cyclases, especially those of cis-acting thioesterases, the most general cyclizing machinery in NRP biosynthesis. Growing insights into penicillin-binding protein-type thioesterases, a relatively new group of trans-acting thioesterases, are also summarized.

Graphical abstract

肽的大环化降低了构象的灵活性，有可能带来更好的类药物特性。然而，副反应（如外嵌化和寡聚化）往往给合成带来挑战。在非核糖体肽（NRP）的生物合成过程中，肽环化生物催化剂作为化学酶工具具有显著的潜力，可以更直接地获得复杂的大环。本综述重点介绍了 NRP 环化酶的生物催化潜力，尤其是顺式作用硫酯酶的潜力，硫酯酶是 NRP 生物合成中最常见的环化机制。此外，还概述了对青霉素结合蛋白型硫酯酶这一相对较新的反式硫酯酶组的深入了解。

引用次数: 0

High-resolution X-ray computed tomography for identifying herbal medicines was as effective as microscopic examination 高分辨率 X 射线计算机断层扫描技术在鉴别草药方面与显微镜检查同样有效。

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-08-29 DOI: 10.1007/s11418-024-01840-z

Hiroko Tokumoto, Nahoko Uchiyama, Michiho Ito

Microscopic examination is one of the important identification methods for crude drug test described in the 18th Japanese Pharmacopoeia. This method is useful for identification because it can be used for small amounts of samples regardless of their storage conditions; however, this method requires a lot of technical skill in sectioning intricate and/or small samples and is time-consuming. High-resolution X-ray computed tomography (HRXCT) is a novel method for observing the internal morphology of materials. Previously, we used HRXCT to visualize the internal morphology of the Ephedra Herb, obtaining observations that closely match those obtained via microscopic examination. HRXCT employs a low-energy X-ray source and the permeation distance of the X-rays is very short. Therefore, HRXCT can be used for elucidating the morphology of small herbal medicines. In this study, Artemisia Capillaris Flower (capitulum with a diameter of approximately 2 mm) and Plantago Seed (seeds with a length of approximately 2 mm) were examined. The results showed that HRXCT examination was sufficient to illustrate the internal independent organs of Artemisia Capillaris Flower and that their inflorescences remained intact. When observing Plantago Seed, the internal morphology of more than one seed can be depicted simultaneously. Therefore, observation using HRXCT was easy, simple, and effective to illustrate the internal morphology of herbal medicines, which is typically time-consuming and requires advanced microscopy skills.

Graphical Abstract

显微镜检查是《第 18 版日本药典》中描述的粗制药物测试的重要鉴定方法之一。这种方法适用于少量样品，不受其储存条件的限制，因此对鉴定非常有用；但是，这种方法在对复杂和/或少量样品进行切片时需要大量的技术技能，而且耗时较长。高分辨率 X 射线计算机断层扫描（HRXCT）是一种观察材料内部形态的新方法。此前，我们使用 HRXCT 观察了麻黄草的内部形态，观察结果与显微镜检查结果非常接近。HRXCT 采用低能量 X 射线源，X 射线的穿透距离非常短。因此，HRXCT 可用于阐明小药材的形态。本研究对茵陈蒿花（蒴果直径约 2 毫米）和车前子种子（种子长度约 2 毫米）进行了检测。结果表明，HRXCT 检查足以说明茵陈蒿花的内部独立器官及其花序保持完整。在观察车前子种子时，可以同时描绘多个种子的内部形态。因此，使用 HRXCT 观察说明中药材的内部形态既方便又简单有效，而这通常是费时且需要高级显微技术的。

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引用次数: 0

Isolation of new indole alkaloid triglucoside from the aqueous extract of Uncaria rhynchophylla 从麒麟菜的水提取物中分离出新的吲哚生物碱三葡萄糖苷。

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-08-22 DOI: 10.1007/s11418-024-01836-9

Yuta Koseki, Hiroaki Nishimura, Ryuji Asano, Katsuyuki Aoki, Li Shiyu, Ryosuke Sugiyama, Mami Yamazaki

Uncaria rhynchophylla (Miq.) Miq. (Rubiaceae) is widely used as a botanical raw material for traditional Japanese and Chinese medicines. However, not all of its potentially bioactive constituents have been isolated and characterized. Herein, one new indole alkaloid triglucoside (1), nine known alkaloids (2–10) and thirteen known non-alkaloids (11–23) were isolated from the aqueous extract of Uncaria rhynchophylla hook and structurally characterized ¹H and ¹³C NMR and high-resolution electrospray ionization mass spectrometry. The absolute configurations of isolated compounds (1, 2 and 3) were determined by the X-ray diffraction analysis of their single crystals obtained using a micro-drop crystallization technique. This technique allows single crystals to be obtained from samples as small as 50 µg, thus providing detailed structural information even on minor constituents and enabling the accurate quality monitoring of botanical raw materials more accurately.

Graphical abstract

Uncaria rhynchophylla (Miq.) Miq.(茜草科）被广泛用作日本和中国传统药物的植物原料。然而，并非所有潜在的生物活性成分都已被分离和鉴定。本文从钩吻的水提取物中分离出一种新的吲哚生物碱三葡萄糖苷（1）、九种已知生物碱（2-10）和十三种已知非生物碱（11-23），并用 1H 和 13C NMR 以及高分辨率电喷雾离子化质谱进行了结构表征。分离出的化合物（1、2 和 3）的绝对构型是通过采用微滴结晶技术获得的单晶的 X 射线衍射分析确定的。该技术可从小至 50 微克的样品中获得单晶体，从而提供详细的结构信息，即使是次要成分也不例外，从而能够更准确地对植物原材料进行精确的质量监测。

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引用次数: 0

Eleven new glycosidic acid methyl esters from the crude resin glycoside fraction of Ipomoea alba seeds 从白花苕子种子粗树脂苷部分中提取的 11 种新苷酸甲酯。

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-08-19 DOI: 10.1007/s11418-024-01838-7

Nodoka Misuda, Hirotaka Nishikawa, Shin Yasuda, Hiroyuki Miyashita, Hitoshi Yoshimitsu, Ryota Tsuchihashi, Masafumi Okawa, Junei Kinjo, Masateru Ono

Resin glycosides are characteristic of plants of the Convolvulaceae family and are well-known purgative ingredients in crude drugs, such as Rhizoma Jalapae, Orizaba Jalapa Tuber, and Pharbitidis Semen, which are used in traditional medicine and derived from plants belonging to this family. Isolated resin glycosides have demonstrated diverse biological activities, including antibacterial, ionophoric, anti-inflammatory, antiviral, and multidrug-resistance-modulating properties, as well as cytotoxicity against cancer cells. These compounds consist of hydroxyl fatty acid oligoglycosides (glycosidic acids), with portions of the saccharide moieties acylated with some organic acids to form the core structure. This study investigated the glycosidic acid components of a crude resin glycoside fraction obtained from a methanolic extract of Ipomoea alba L. seeds (Convolvulaceae). Eleven new glycosidic acid methyl esters and one known methyl ester were isolated from a glycosidic acid fraction treated with trimethylsilyldiazomethane in hexane. Their structures were determined using acidic hydrolysis and electrospray ionization-time of fight mass spectrometry and NMR spectral analyses. These compounds are penta-, tetra-, or triglycosides, with methyl 11S-hydroxytetradecanoate or methyl 11S-hydroxyhexadecanoate as the aglycone. Although d-quinovose and l-rhamnose are common monosaccharide components, the remaining monosaccharides are d-glucose, d-xylose, or d-fucose. The crude resin glycoside fraction showed non-negligible cytotoxicity against HL-60 human promyelocytic leukemia cells.

Graphical abstract

树脂苷是旋花科（Convolvulaceae）植物的特征，也是粗制药物中著名的清热解毒成分，如 Rhizoma Jalapae、Orizaba Jalapa Tuber 和 Pharbitidis Semen。分离出的树脂苷具有多种生物活性，包括抗菌、离子渗透、消炎、抗病毒和调节多种药物耐药性的特性，以及对癌细胞的细胞毒性。这些化合物由羟基脂肪酸低聚糖苷（糖苷酸）组成，部分糖基与一些有机酸酰化形成核心结构。本研究调查了从白花苕子（旋花科）种子甲醇提取物中获得的粗树脂苷部分中的苷酸成分。在正己烷中用三甲基硅基二氮甲烷处理的苷酸馏分中分离出了 11 种新的苷酸甲酯和 1 种已知的甲酯。利用酸性水解、电喷雾电离时间质谱法和核磁共振光谱分析确定了它们的结构。这些化合物都是以 11S-hydroxytetradecanoate 甲酯或 11S-hydroxyhexadecanoate 甲酯为苷元的五元苷、四元苷或三元苷。虽然 D-奎诺糖和 L-鼠李糖是常见的单糖成分，但其余单糖为 D-葡萄糖、D-木糖或 D-岩藻糖。粗树脂苷部分对 HL-60 人类早幼粒细胞白血病细胞具有不可忽视的细胞毒性。

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引用次数: 0

Isolation of C-29 oxygenated oleanane triterpenoids and a (+)-muurolene type sesquiterpenoid from the fruiting bodies of Fuscoporia torulosa and their bioactivities 从 Fuscoporia torulosa 子实体中分离出 C-29 含氧齐墩果烷三萜类化合物和一种 (+)-muurolene 型倍半萜类化合物及其生物活性。

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-08-10 DOI: 10.1007/s11418-024-01832-z

Tatsuro Yoneyama, Chian Chen, Yoshihiro Ichimura, Katsuyuki Nakashima, Hiromichi Kenmoku, Hiroshi Imagawa, Akemi Umeyama, Masaaki Noji

Basidiomycetes with a wide variety of skeletons of secondary metabolites can be expected to be the source of new interesting biological compounds. During our research on basidiomycetes, two new C-29 oxygenated oleanane-type triterpenes (1 and 2) and torulosacid (3), a muurolene type sesquiterpenoid with a five-membered ether ring along with nine known compounds (4–12), were isolated from the MeOH extract of the fruiting bodies of Fuscoporia torulosa. The structures of 1–3 were determined by NMR and HREIMS analysis. Further studies on the stereochemistry of 3 were conducted using X-ray crystallographic analysis and comparison of experimental and calculated ECD spectra. In the antimicrobial assay of isolates, 1, 7, and 9 showed growth inhibitory activity against methicillin-resistant Staphylococcus aureus and other gram-positive strains. Isolation of oleanane type triterpenes from fungi including basidiomycetes, is a unique report that could lead to further isolation of new compounds and the discovery of unique biosynthetic enzymes.

Graphical abstract

基枝菌具有多种次级代谢产物骨架，有望成为新的有趣生物化合物的来源。在对基生真菌的研究过程中，我们从 Fuscoporia torulosa 子实体的 MeOH 提取物中分离出了两种新的 C-29 含氧齐墩果烷型三萜类化合物（1 和 2）和 torulosacid（3），后者是一种具有五元醚环的室烯类倍半萜化合物，以及九种已知化合物（4-12）。通过核磁共振和 HREIMS 分析确定了 1-3 的结构。利用 X 射线晶体学分析以及实验和计算的 ECD 光谱比较，对 3 的立体化学结构进行了进一步研究。在对分离物进行的抗菌试验中，1、7 和 9 对耐甲氧西林金黄色葡萄球菌和其他革兰氏阳性菌株具有生长抑制活性。从真菌（包括基枝真菌）中分离出齐墩果烷型三萜类化合物是一项独特的研究成果，可进一步分离出新的化合物并发现独特的生物合成酶。

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引用次数: 0

Formohyperins G–L, polycyclic prenylated benzoylphloroglucinols from the flowers of Hypericum formosanum Formohyperins G-L，来自金丝桃花的多环前酰化苯甲酰氯葡萄糖醇。

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-08-10 DOI: 10.1007/s11418-024-01839-6

Rena Takizawa, Yusei Shimomoto, Daisuke Tsuji, Kiyoshi Imabayashi, Kohji Itoh, Reiko Akagi, Yoshiki Kashiwada, Naonobu Tanaka

Phytochemical study on the flowers of Hypericum formosanum Maxim. (Hypericaceae) led to the isolation of formohyperins G–L (1–6), whose structures were assigned by detailed spectroscopic analysis. Formohyperins G–L (1–6) are new benzoylphloroglucinols substituted by a C₁₀ unit, a prenyl group, and a methyl group. Formohyperins G–J (1–4) possess a 6/6/6-tricyclic structure, while formohyperins K (5) and L (6) have a unique 6/6/5/4-tetracyclic structure consisting of cyclohexadienone, dihydropyrane, cyclopentane, and cyclobutane rings. The absolute configurations of 1–6 were deduced by analysis of the ECD spectra. Formohyperins G–J (1–4) and L (6) were found to show potent inhibitory activities against IL-1β release from LPS-treated murine microglial cells with EC₅₀ values of 5.0, 10.9, 6.3, 10.8, and 13.7 µM, respectively, without cytotoxicity. 6-O-Methylformohyperins G (1a) and I (3a) also exhibited the inhibitory activities with EC₅₀ values of 4.7 and 2.7 µM, respectively, although they were cytotoxic against microglial cells.

Graphical abstract

对金丝桃（Hypericaceae）花进行的植物化学研究分离出了金丝桃素 G-L（1-6），并通过详细的光谱分析确定了其结构。(金丝桃科植物）的植物化学研究中分离出了金丝桃素 G-L（1-6），并通过详细的光谱分析确定了其结构。Formohyperins G-L (1-6) 是由一个 C10 单元、一个链烯基和一个甲基取代的新的苯甲酰氯葡萄糖醇。福尔马林 G-J（1-4）具有 6/6/6 三环结构，而福尔马林 K（5）和 L（6）则具有独特的 6/6/5/4 四环结构，由环己二烯酮、二氢吡喃、环戊烷和环丁烷环组成。通过分析 ECD 光谱推断出了 1-6 的绝对构型。研究发现，福莫西汀 G-J（1-4）和 L（6）对经 LPS 处理的小鼠小胶质细胞的 IL-1β 释放具有强效抑制作用，EC50 值分别为 5.0、10.9、6.3、10.8 和 13.7 µM，且无细胞毒性。6-O-Methylformohyperins G (1a) 和 I (3a) 也具有抑制活性，EC50 值分别为 4.7 和 2.7 µM，但它们对小胶质细胞具有细胞毒性。

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引用次数: 0

Screening and identification of reactive metabolic compounds of Cortex Periplocae based on glutathione capture-mass spectrometry 基于谷胱甘肽捕获-质谱法筛选和鉴定Cortex Periplocae的活性代谢化合物。

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-08-05 DOI: 10.1007/s11418-024-01835-w

Guantong Yu, Ruirui Wang, Xiaomei Liu, Yuhong Li, Lin Li, Xiaoming Wang, Yuhong Huang, Guixiang Pan

As a traditional Chinese medicine (TCM), Cortex Periplocae (CP) has a wide range of pharmacological effects, as well as toxic side effects. The main toxic components of it are cardiac glycosides, which tend to cause cardiotoxicity. Currently, it has also been reported in studies to cause hepatotoxicity, but it is not clear whether the hepatotoxicity is related to the toxicity caused by the reactive metabolites. This study aims to investigate the target components of CP that generate reactive metabolic toxicity. The fluorescent probe method was used to detect glutathione (GSH)-trapped reactive metabolites in a co-incubation system of CP extract with rat liver microsomes. Identification of GSH conjugates was performed by LC–MS/MS and that of the possible precursor components that produce reactive metabolites was conducted by UPLC–Q-TOF/MS. Cell viability assays were performed on HepG2 and L02 cells to determine the cytotoxicity of the target components. The findings of our study demonstrate that the extract derived from CP has the ability to generate metabolites that exhaust the intracellular GSH levels, resulting in the formation of GSH conjugates and subsequent cytotoxic effects. Through the utilization of the UPLC–Q-TOF/MS technique, we were able to accurately determine the molecular weight of the precursor compound in CP to be 355.1023. The primary evidence to determining the GSH conjugetes relies on the appearance of characteristic product ions resulting from central neutral loss (CNL) scanning of 129 Da and product scanning of m/z 660 in the positive MS/MS spectrum. Through analysis, it was ultimately ascertained that the presence of chlorogenic acid (CGA) and its isomers, namely neochlorogenic acid (NCGA) and cryptochlorogenic acid (CCGA), could lead to the production of GSH conjugates, resulting in cytotoxicity at elevated levels. Taking these findings into consideration, the underlying cause for the potential hepatotoxicity of CP was initially determined.

Graphical abstract

作为一种传统中药，陈皮具有广泛的药理作用和毒副作用。其主要毒性成分是强心苷，容易引起心脏毒性。目前，也有研究报告称其会引起肝脏毒性，但尚不清楚肝脏毒性是否与活性代谢物引起的毒性有关。本研究旨在探究产生反应性代谢毒性的氯化石蜡靶成分。采用荧光探针法检测氯化石蜡提取物与大鼠肝脏微粒体共孵育体系中被谷胱甘肽（GSH）捕获的活性代谢物。通过 LC-MS/MS 鉴定了谷胱甘肽共轭物，并通过 UPLC-Q-TOF/MS 鉴定了产生活性代谢物的可能前体成分。对 HepG2 和 L02 细胞进行了细胞活力测定，以确定目标成分的细胞毒性。我们的研究结果表明，从氯化石蜡中提取的萃取物能够产生代谢物，耗尽细胞内的 GSH 水平，形成 GSH 共轭物，从而产生细胞毒性作用。通过使用 UPLC-Q-TOF/MS 技术，我们能够准确地确定氯化石蜡中的前体化合物的分子量为 355.1023。确定 GSH 共轭物的主要证据是，在 MS/MS 正谱中，出现了中心中性损失（CNL）扫描 129 Da 和产物扫描 m/z 660 的特征产物离子。通过分析，最终确定绿原酸（CGA）及其异构体（即新绿原酸（NCGA）和隐绿原酸（CCGA））的存在可导致产生 GSH 共轭物，从而在浓度升高时产生细胞毒性。考虑到这些发现，我们初步确定了氯化石蜡潜在肝毒性的根本原因。

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引用次数: 0

Study on the chemical composition and anti-fungi activities of anthraquinones and its glycosides from Rumex japonicus Houtt. 日本鲁梅克斯（Rumex japonicus Houtt.

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-08-05 DOI: 10.1007/s11418-024-01834-x

He Sun, Dandan Xiao, Xue Li, Tong Sun, Fanying Meng, Xinting Shao, Yuling Ding, Yong Li

Fungi, such as Trichophyton rubrum (T. rubrum) and Microsporum canis Bodin Anamorph (M. canis Bodin Anamorph) are the main pathogens of dermatophysis. According to ancient books records, Rumex japonicus Houtt. (RJH) has a miraculous effect on the treatment of dermatophysis. To reveal the anti-fungi (T. rubrum and M. canis Bodin Anamorph) components and its mechanism of the Rumex japonicus Houtt. The vinegar extraction and alcohol precipitation, HPLC and nuclear magnetic resonance spectroscopy (NMR) were employed for analyzing the chemical compositions of RJH; in vitro anti-fungal experiment was investigated including test the minimum inhibitory concentration (MIC) and the minimum fungicidal concentration (MFC), spore germination rate, nucleic acid, protein leakage rate, biofilm structure, and the mechanism of anti-fungal and anti-fungal biofilms in RJH. Seven anthraquinones and their glycoside compounds were obtained in this study respectively, such as chrysophanol, physcion, aloe-emodin, emodin, rhein, emodin-8-O-β-D-glucoside and chrysophanol-8-O-β-D-glucoside. In vitro anti-fungal experiment results showed that RJH extracts have good anti-fungal activity for dermatophytic fungi. Among them, the MIC of the rhein, emodin and aloe-emodin against T. rubrum are 1.9 µg/ml, 3.9 µg/ml and 15.6 µg/ml, respectively; the MIC of emodin and aloe-emodin against M. canis Bodin Anamorph are 7.8 µg/ml and 62.5 µg/ml, respectively. In addition, its active components can inhibit fungal spore germination and the formation of bud tube, change cell membrane permeability, prevent hyphal growth, destroy biofilm structure, and down-regulate the expression of agglutinin-like sequence family 1 of the adhesion phase of biofilm growth. The study shows that RJH play a fungicidal role.

Graphic abstract

真菌，如红毛癣菌（T. rubrum）和犬小孢子菌（M. canis Bodin Anamorph）是皮炎的主要病原体。根据古书记载，Rumex japonicus Houtt.(Rumex japonicus Houtt.为了揭示 Rumex japonicus Houtt.采用醋提取和醇沉法、高效液相色谱法和核磁共振波谱法分析了日本留兰香的化学成分；研究了日本留兰香的体外抗真菌实验，包括测试最小抑菌浓度（MIC）和最小杀菌浓度（MFC）、孢子萌发率、核酸、蛋白质泄漏率、生物膜结构以及日本留兰香抗真菌和抗真菌生物膜的机理。本研究获得了七种蒽醌类化合物及其苷类化合物，分别为菊花酚、大黄素、芦荟大黄素、大黄素、大黄素-8-O-β-D-葡萄糖苷和菊花酚-8-O-β-D-葡萄糖苷。体外抗真菌实验结果表明，RJH 提取物对皮癣真菌具有良好的抗真菌活性。其中，流苏碱、大黄素和芦荟大黄素对红念珠菌的 MIC 分别为 1.9 µg/ml、3.9 µg/ml 和 15.6 µg/ml；大黄素和芦荟大黄素对犬毛癣菌的 MIC 分别为 7.8 µg/ml 和 62.5 µg/ml。此外，其活性成分还能抑制真菌孢子萌发和芽管形成，改变细胞膜通透性，阻止菌丝生长，破坏生物膜结构，下调生物膜生长粘附期凝集素样序列家族 1 的表达。研究表明，RJH 具有杀菌作用。

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