Journal of Natural Medicines最新文献

英文中文

Correction: Preparation and pharmaceutical properties of Hangeshashinto oral ointment and its safety and efficacy in Syrian hamsters with 5-fluorouracil-induced oral mucositis 更正：Hangeshashinto口服软膏的制备、药理特性及其对5-氟尿嘧啶诱发的叙利亚仓鼠口腔黏膜炎的安全性和有效性。

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-04-02 DOI: 10.1007/s11418-024-01806-1

Takashi Ogihara, Masato Kagawa, Rintarou Yamanaka, Satoshi Imai, Kotaro Itohara, Daiki Hira, Shunsaku Nakagawa, Atsushi Yonezawa, Michiho Ito, Takayuki Nakagawa, Tomohiro Terada, Kazuo Matsubara

引用次数: 0

Bajitianwan formula extract ameliorates bone loss induced by iron overload via activating RAGE/PI3K/AKT pathway based on network pharmacology and transcriptomic analysis 基于网络药理学和转录组学分析，八吉田湾配方提取物通过激活RAGE/PI3K/AKT通路，改善铁超载引起的骨质流失。

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-03-26 DOI: 10.1007/s11418-024-01779-1

Weifan Xu, Tao Jiang, Luying Ding, Yiping Jiang, Lichao Zhang, Tianshuang Xia, Hailiang Xin

Osteoporosis (OP) is closely related to iron overload. Bajitianwan (BJTW) is a traditional Chinese medicine formulation used for treating senile diseases such as dementia and osteoporosis. Modern pharmacological researches have found that BJTW has beneficial effect on bone loss and memory impairment in aging rats. This paper aimed to explore the role and mechanism of BJTW in ameliorating iron overload-induced bone loss. Furthermore, BJTW effectively improved the bone micro-structure of the femur in mice, and altered bone metabolism biomarkers alkaline phosphatase (ALP) and osteocalcin (OCN) in serum, as well as oxidative indexes superoxide dismutase (SOD), catalase (CAT), glutathione reductase (GR) glutathione (GSH) and malondialdehyde (MDA) in liver. As for network pharmacology, 73 components collected from BJTW regulated 99 common targets merged in the BJTW and OP. The results of RNA-seq indicated that there were 418 potential targets in BJTW low dose group (BJTW-L) and 347 potential targets in BJTW high dose group (BJTW-H). Intriguingly, both PI3K-AKT signaling pathway and the AGEs-RAGE signaling pathway were contained in the KEGG pathways enrichment results of network pharmacology and transcriptomics, which were considered as the potential mechanism. Additionally, we verified that BJTW regulated the expression of related proteins in RAGE/PI3K-AKT pathways in MC3T3-E1 cells. In summary, BJTW has potent effect on protecting against iron overload-induced OP, and its mechanism may be related to the activation of the RAGE/PI3K-AKT signaling pathways.

Graphic abstract

骨质疏松症（OP）与铁超载密切相关。八味天丸是一种用于治疗老年痴呆和骨质疏松症等老年性疾病的传统中药配方。现代药理研究发现，八味天丸对衰老大鼠的骨质疏松和记忆力减退有一定疗效。本文旨在探讨 BJTW 在改善铁超载引起的骨质流失中的作用和机制。此外，BJTW还能有效改善小鼠股骨的骨微结构，改变血清中骨代谢生物标志物碱性磷酸酶（ALP）和骨钙素（OCN），以及肝脏中氧化指标超氧化物歧化酶（SOD）、过氧化氢酶（CAT）、谷胱甘肽还原酶（GR）、谷胱甘肽（GSH）和丙二醛（MDA）。在网络药理学方面，从 BJTW 中收集的 73 个成分调控了 BJTW 和 OP 中合并的 99 个共同靶标。RNA-seq结果显示，BJTW低剂量组（BJTW-L）有418个潜在靶点，BJTW高剂量组（BJTW-H）有347个潜在靶点。有趣的是，PI3K-AKT 信号通路和 AGEs-RAGE 信号通路都包含在网络药理学和转录组学的 KEGG 通路富集结果中，被认为是潜在的机制。此外，我们还验证了BJTW能调节MC3T3-E1细胞中RAGE/PI3K-AKT通路相关蛋白的表达。综上所述，BJTW 对铁超载诱导的 OP 具有有效的保护作用，其机制可能与激活 RAGE/PI3K-AKT 信号通路有关。

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引用次数: 0

Alliaxylines A–E: five new mexicanolides from the stem barks of Dysoxylum alliaceum (Blume) Blume ex A.Juss Alliaxylines A-E: Five new mexicanolides from the stem barks of Dysoxylum alliaceum (Blume) Blume ex A.Juss.

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-03-22 DOI: 10.1007/s11418-024-01794-2

Sandra Amalia Riyadi, Al Arofatus Naini, Tri Mayanti, Ronny Lesmana, Mohamad Nurul Azmi, Sofa Fajriah, Siriporn Jungsuttiwong, Unang Supratman

A total of five new mexicanolides (1–5), namely alliaxylines A–E, together with two known limonoids 6 and 7, were isolated and identified from Dysoxylum alliaceum (Blume) Blume ex. A.Juss. (Meliaceae). The structures of these compounds were elucidated based on extensive spectroscopic analyses, including HR-ESI–MS, UV, IR, 1D, and 2D NMR, as well as theoretical stimulation of NMR shifts with the DP4 + algorithm. Consequently, this study aimed to examine cytotoxic activities of these compounds against MCF-7 and A549 cell lines. The results implied that compound 2 was the most potent against the two tested cells, with IC₅₀ values of 34.95 ± 0.21 and 44.39 ± 1.03 µM.

Graphical Abstract

从 Dysoxylum alliaceum (Blume) Blume ex.A.Juss.(Meliaceae）中分离并鉴定了这些化合物。这些化合物的结构是通过广泛的光谱分析（包括 HR-ESI-MS、UV、IR、1D 和 2D NMR）以及使用 DP4 + 算法对 NMR 移位进行理论推导而阐明的。因此，本研究旨在考察这些化合物对 MCF-7 和 A549 细胞株的细胞毒性活性。结果表明，化合物 2 对两种受测细胞的毒性最强，IC50 值分别为 34.95 ± 0.21 和 44.39 ± 1.03 µM。

引用次数: 0

A new 3,4-seco-isopimarane and three new isopimarane diterpenoids from Kaempferia champasakensis collected from Vietnam and their cytotoxic activities 从越南采集的Kaempferia champasakensis中发现的一种新的3,4-seco-isopimarane和三种新的isopimarane二萜类化合物及其细胞毒性活性。

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-03-22 DOI: 10.1007/s11418-024-01789-z

Kiep Minh Do, Shotaro Hoshino, Takeshi Kodama, Hien Minh Nguyen, Son Van Le, Naotaka Ikumi, Hiroyasu Onaka, Hiroyuki Morita

A phytochemical investigation of Kaempferia champasakensis rhizomes led to the isolation of a new 3,4-seco-isopimarane diterpene, kaempferiol A (1), and three new isopimarane diterpenes, kaempferiols B–D (2–4), together with six known isopimarane diterpenes (5–10). The structures of 1–4 were elucidated by extensive spectroscopic analyses, including HR-ESI–MS, UV, IR, and 1D and 2D NMR. The absolute configurations of 1, 3, and 4 were determined by ECD calculations, while that of 2 was established using the modified Mosher method. All isolated compounds were tested for cytotoxicity against three human cancer cell lines, lung cancer (A549), cervical cancer (HeLa), and breast cancer (MCF-7). Among them, 6 and 7 showed moderate cytotoxic activities against the three tested cell lines, with IC₅₀ values ranging from 38.04 to 27.77 μM, respectively.

Graphical abstract

通过对山奈根茎进行植物化学研究，分离出了一种新的 3,4-seco-isopimarane（山奈酚）二萜，即山奈酚 A（1）和三种新的异山奈酚二萜，即山奈酚 B-D（2-4），以及六种已知的异山奈酚二萜（5-10）。通过广泛的光谱分析，包括 HR-ESI-MS、紫外光谱、红外光谱以及一维和二维核磁共振，阐明了 1-4 的结构。1、3 和 4 的绝对构型是通过 ECD 计算确定的，而 2 的绝对构型则是通过改进的 Mosher 方法确定的。所有分离出的化合物都对三种人类癌细胞系（肺癌（A549）、宫颈癌（HeLa）和乳腺癌（MCF-7））进行了细胞毒性测试。其中，6 号和 7 号化合物对三种受试细胞株具有中等程度的细胞毒性活性，IC50 值分别为 38.04 至 27.77 μM。

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引用次数: 0

Non-enzymatic reactions in biogenesis of fungal natural products 真菌天然产物生物生成过程中的非酶反应。

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-03-22 DOI: 10.1007/s11418-024-01797-z

Shinji Kishimoto

Fungi have long been regarded as abundant sources of natural products (NPs) exhibiting significant biological activities. Decades of studies on the biosynthesis of fungal NPs revealed that most of the biosynthetic steps are catalyzed by sophisticated enzymes encoded in biosynthetic gene clusters, whereas some reactions proceed without enzymes. These non-enzymatic reactions complicate biosynthetic analysis of NPs and play important roles in diversifying the structure of the products. Therefore, knowledge on the non-enzymatic reactions is important for elucidating the biosynthetic mechanism. This review focuses on non-enzymatic reactions we recently encountered during biosynthetic studies of four types of NPs (viridicatins, Sch210972, lentopeptins, and lentofuranine).

Graphical abstract

长期以来，真菌一直被认为是具有重要生物活性的天然产物（NPs）的丰富来源。几十年来对真菌 NPs 生物合成的研究表明，大多数生物合成步骤是由生物合成基因簇中编码的复杂酶催化的，而有些反应则是在没有酶的情况下进行的。这些非酶反应使 NPs 的生物合成分析变得复杂，并对产品结构的多样化起着重要作用。因此，了解非酶反应对于阐明生物合成机制非常重要。本综述重点介绍我们最近在四种 NPs（病毒素、Sch210972、扁桃肽和扁桃呋喃碱）的生物合成研究中遇到的非酶反应。

引用次数: 0

Inhibitory effects of senkyuchachosan on SARS-CoV-2 papain-like protease activity in vitro 参久草散对体外 SARS-CoV-2 木瓜蛋白酶样蛋白酶活性的抑制作用

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-03-21 DOI: 10.1007/s11418-024-01788-0

Yuka Kiba, Takashi Tanikawa, Tsuyoshi Hayashi, Takami Yokogawa, Aiko Sano, Ryuichiro Suzuki, Masashi Kitamura

Papain-like protease (PLpro) enzyme plays a vital role in viral replication as it breaks down polyproteins and disrupts the host's immune response. There are few reports on Kampo formulas that focus on PLpro activity. In this study, we evaluated the inhibitory effects of senkyuchachosan, a traditional Japanese medicine, on PLpro of SARS-CoV-2, the virus responsible for causing COVID-19. We purified the PLpro enzyme and conducted in vitro enzymatic assays using specific substrates. Among the nine crude drugs present in senkyuchachosan, four (Cyperi Rhizoma, Schizonepetae Spica, Menthae Herba, and Camelliae sinensis Folium [CsF]) strongly inhibited PLpro activity. CsF, derived from Camellia sinensis (green tea), contains polyphenols, including catechins and tannins. To confirm that the PLpro inhibitory effects of senkyuchachosan predominantly stem from tannins, the tannins were removed from the decoction using polyvinylpolypyrrolidone (PVPP). The inhibitory effect of senkyuchachosan on PLpro activity was reduced by the removal of PVPP. In addition, the tannin fraction obtained from the CsF extracts showed significant PLpro inhibitory effects. These findings lay the groundwork for the potential development of therapeutic agents that target SARS-CoV-2 infection by intervening in proteolytic cleavage of the virus.

木瓜蛋白酶（Papain-like protease，PLpro）在病毒复制过程中起着至关重要的作用，因为它能分解多聚蛋白，破坏宿主的免疫反应。很少有关于康普配方的报告关注木瓜蛋白酶的活性。在本研究中，我们评估了日本传统药物仙草散对 SARS-CoV-2（引起 COVID-19 的病毒）的 PLpro 的抑制作用。我们纯化了 PLpro 酶，并使用特定底物进行了体外酶学试验。在仙草散中的九种粗制药物中，有四种（香附、五味子、薄荷和山茶叶 [CsF]）能强烈抑制 PLpro 的活性。CsF 提取自山茶（绿茶），含有儿茶素和单宁等多酚类物质。为了证实仙草茶散对 PLpro 的抑制作用主要来自单宁酸，我们使用聚乙烯基吡咯烷酮（PVPP）去除煎煮液中的单宁酸。去除 PVPP 后，仙草茶散对 PLpro 活性的抑制作用减弱。此外，从 CsF 提取物中获得的单宁酸部分对 PLpro 有显著的抑制作用。这些发现为通过干预病毒的蛋白水解作用来开发针对 SARS-CoV-2 感染的治疗药物奠定了基础。

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引用次数: 0

Recent trends in ginseng research 人参研究的最新趋势。

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-03-21 DOI: 10.1007/s11418-024-01792-4

Honoka Ito, Michiho Ito

Ginseng, the dried root of Panax ginseng, contains ginsenosides and has long been used in Korea, China, and Japan to treat various symptoms. Many studies on the utility of ginseng have been conducted and in this paper we investigate recent trends in ginseng research. P. ginseng studies were collected from scientific databases (PubMed, Web of Science, and SciFinderⁿ) using the keywords “Panax ginseng C.A. Meyer”, “ginsenosides”, “genetic diversity”, “biosynthesis”, “cultivation”, and “pharmacology”. We identified 1208 studies up to and including September 2023: 549 studies on pharmacology, 262 studies on chemical components, 131 studies on molecular biology, 58 studies on cultivation, 71 studies on tissue culture, 28 studies on clinical trials, 123 reviews, and 49 studies in other fields. Many researchers focused on the characteristic ginseng component ginsenoside to elucidate the mechanism of ginseng’s pharmacological action, the relationship between component patterns and cultivation areas and conditions, and gene expression.

Graphical abstract

人参是三七的干燥根茎，含有人参皂苷，长期以来一直被韩国、中国和日本用于治疗各种症状。有关人参功效的研究很多，本文将探讨人参研究的最新趋势。我们以 "Panax ginseng C.A. Meyer"、"ginsenosides"、"genetic diversity"、"biosynthesis"、"cultation "和 "pharmacology "为关键词，从科学数据库（PubMed、Web of Science和SciFindern）中收集了有关人参的研究。截至 2023 年 9 月（含 2023 年 9 月），我们共检索到 1208 项研究：其中药理学研究 549 项，化学成分研究 262 项，分子生物学研究 131 项，栽培研究 58 项，组织培养研究 71 项，临床试验研究 28 项，综述研究 123 项，其他领域研究 49 项。许多研究人员关注人参的特征成分人参皂苷，以阐明人参的药理作用机制、成分模式与栽培地区和条件的关系以及基因表达。

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引用次数: 0

Photoreaction products of extract from the fruiting bodies of Polyozellus multiplex 多子藻子实体提取物的光反应产物。

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-03-21 DOI: 10.1007/s11418-024-01790-6

Hayato Otsuka, Keiyo Nakai, Emi Shimizu, Takamasa Yamaguchi, Mitsuhisa Yamano, Hiroaki Sasaki, Kiyotaka Koyama, Kaoru Kinoshita

Photochemical reactions are powerful tools for synthesizing organic molecules. The input of energy provided by light offers a means to produce strained and unique molecules that cannot be assembled using thermal protocols, allowing for the production of immense molecular complexity in a single chemical step. Furthermore, unlike thermal reactions, photochemical reactions do not require active reagents such as acids, bases, metals, or enzymes. Photochemical reactions play a central role in green chemistry. This article reports the isolation and structure determination of four new compounds (1–4) from the photoreaction products of the Polyozellus multiplex MeOH ext. The structures of the new compounds were elucidated using MS, IR, comprehensive NMR measurements and microED. The four compounds were formed by deacetylation of polyozellin, the main secondary metabolite of P. multiplex, and addition of singlet oxygen generated by sunlight. To develop drugs for treating Alzheimer’s disease (AD) on the basis of the amyloid cascade hypothesis, the compounds (1–4) obtained by photoreaction were evaluated for BACE1 inhibitory activity. The hydrolysates (5 and 6) of polyozellin, the main secondary metabolites of P. multiplex, were also evaluated. The photoreaction products (3 and 4) and hydrolysates (5 and 6) of polyozellin showed BACE1 inhibitory activity (IC₅₀: 2.2, 16.4, 23.3, and 5.3 μM, respectively).

Graphical abstract

光化学反应是合成有机分子的强大工具。光能提供的能量可以产生热反应无法合成的独特分子，从而在单一化学步骤中产生复杂的分子。此外，与热反应不同，光化学反应不需要酸、碱、金属或酶等活性试剂。光化学反应在绿色化学中发挥着核心作用。本文报告了从 Polyozellus multiplex MeOH ext 的光反应产物中分离和测定四种新化合物（1-4）的结构。这四种化合物是由多孔菌的主要次级代谢产物多孔菌素脱乙酰基并加入阳光产生的单线态氧而形成的。为了在淀粉样蛋白级联假说的基础上开发治疗阿尔茨海默病（AD）的药物，对通过光反应获得的化合物（1-4）进行了 BACE1 抑制活性评估。此外，还评估了多浆果藻的主要次级代谢产物多浆果藻素的水解物（5 和 6）。光反应产物（3 和 4）和多浆菌素的水解产物（5 和 6）显示出 BACE1 抑制活性（IC50 分别为 2.2、16.4、23.3 和 5.3 μM）。

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引用次数: 0

Resultant compound from sublimation test for Gentianae Radix in Japanese Pharmacopoeia was 5-(hydroxymethyl)furfural 日本药典》中龙胆草升华试验的结果化合物为 5-（羟甲基）糠醛

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-03-19 DOI: 10.1007/s11418-024-01802-5

Atsushi Tsuge, Yuto Goto, Sayaka Masada, Michiho Ito

Gentianae Radix, an herbal medicine, has been used as a gastrointestinal drug in Japan. In the Japanese Pharmacopoeia 18th Revision, the sublimation test is specified as an identification test for Gentianae Radix. The compound obtained in this sublimation test was believed to be gentisin, a xanthone family compound. However, the compound we identified using liquid chromatography-high-resolution mass spectrometry (LC-HRMS) and ¹H- and ¹³C-NMR was 5-(hydroxymethyl)furfural (5-HMF). The same compound was found to be a sublimate of Gentianae Scabrae Radix and Gentianae Macrophyllae Radix, belonging to the same genus as Gentianae Radix. These results indicate the necessity to revise the identification test for Gentianae Radix to a more unique method.

Graphical abstract

龙胆草是一种草药，在日本一直被用作胃肠道药物。在《日本药典》第 18 版中，升华试验被规定为龙胆草的鉴定试验。在升华试验中获得的化合物被认为是龙胆素，一种黄酮类化合物。然而，我们使用液相色谱-高分辨质谱法（LC-HRMS）以及 1H- 和 13C-NMR 鉴定出的化合物是 5-（羟甲基）糠醛（5-HMF）。该化合物是龙胆草（Gentianae Scabrae Radix）和龙胆草（Gentianae Macrophyllae Radix）的升华产物，与龙胆草同属。这些结果表明，有必要将龙胆草的鉴定试验修改为一种更独特的方法。

引用次数: 0

The protective effects of Ninjin’yoeito against liver steatosis/fibrosis in a non-alcoholic steatohepatitis model mouse 万年青对非酒精性脂肪性肝炎模型小鼠肝脏脂肪变性/纤维化的保护作用

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines

Pub Date : 2024-03-18 DOI: 10.1007/s11418-024-01786-2

Kyohei Takano, Marisa Kaneda, Yayoi Aoki, Nina Fujita, Shigeki Chiba, Seiwa Michihara, Li-Kun Han, Ryuji Takahashi

Non-alcoholic steatohepatitis (NASH) is a progressive fibrotic form of non-alcoholic fatty liver disease. Liver fibrosis leads to liver cancer and cirrhosis, and drug therapy for NASH remains lacking. Ninjin’yoeito (NYT) has shown antifibrotic effects in a model of liver fibrosis without steatosis but has not been studied for NASH. Therefore, we evaluated the efficacy of NYT in mice fed a choline-deficient, L-amino acid-defined, high-fat diet (CDAHFD) as a NASH model. Compared with the normal diet group, mice fed CDAHFD showed decreased body weight and increased white adipose tissue, liver weight, and triglyceride content in the liver. Furthermore, a substantial increase in the hepatic concentration of hydroxyproline, expression of α-smooth muscle actin (α-SMA), and transforming growth factor-β was observed in CDAHFD-fed mice. Masson’s trichrome and Picro-Sirius red staining revealed a remarkable increase in collagen fiber compared with the normal diet group. Compared with mice that received CDAHFD alone, those supplemented with NYT exhibited reduced hepatic triglyceride and hydroxyproline levels and α-SMA expression. Additionally, compared with the group fed CDAHFD alone, the stained liver tissues of NYT-treated mice exhibited a reduction in Masson’s trichrome- and Picro-Sirius red-positive areas. Locomotor activity was significantly reduced in the CDAHFD-fed group compared with the normal diet group. In the NYT-treated group, the CDAHFD-induced decrease in locomotor activity was significantly suppressed. The findings indicate that NYT inhibited fatty and fibrotic changes in the livers of NASH mice and alleviated the decrease in locomotor activity. Therefore, NYT may serve as a novel therapeutic approach for NASH.

Graphical abstract

摘要非酒精性脂肪性肝炎（NASH）是非酒精性脂肪肝的一种进行性纤维化形式。肝纤维化会导致肝癌和肝硬化，但目前仍缺乏治疗非酒精性脂肪性肝炎的药物。Ninjin'yoeito（NYT）在无脂肪变性的肝纤维化模型中显示出抗纤维化作用，但尚未对 NASH 进行研究。因此，我们以胆碱缺乏、L-氨基酸定义的高脂饮食（CDAHFD）作为 NASH 模型，评估了 NYT 对小鼠的疗效。与正常饮食组相比，喂食CDAHFD的小鼠体重下降，白色脂肪组织、肝脏重量和肝脏中甘油三酯含量增加。此外，CDAHFD组小鼠肝脏中的羟脯氨酸浓度、α-平滑肌肌动蛋白（α-SMA）和转化生长因子-β的表达均显著增加。与正常饮食组相比，Masson 三色和 Picro-Sirius 红染色显示胶原纤维显著增加。与仅摄入 CDAHFD 的小鼠相比，补充 NYT 的小鼠肝甘油三酯和羟脯氨酸水平以及 α-SMA 表达均有所降低。此外，与单独喂食 CDAHFD 的小鼠相比，经 NYT 处理的小鼠肝脏组织的马森氏三色染色和比色红阳性区域有所减少。与正常饮食组相比，喂食CDAHFD组小鼠的运动活动明显减少。在NYT处理组中，CDAHFD引起的运动活性下降被明显抑制。研究结果表明，NYT抑制了NASH小鼠肝脏的脂肪和纤维化变化，并缓解了小鼠运动能力的下降。因此，NYT可作为治疗NASH的一种新方法。图表摘要

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