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Solanapyrone analogues from endophytic Nigrospora sphaerica MZW-A associated with the endangered conifer Pinus wangii 与濒危针叶树 Pinus wangii 相关的 Nigrospora sphaerica MZW-A 内生菌中的茄碱类似物。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-23 DOI: 10.1016/j.fitote.2024.106275
Mengran Wang , Haowei Chen , Lihong Yan , Jingtao Chen , Lu Gan , Zhichun Shen , Juan Xiong , Jinfeng Hu , Jiyang Li
Eight previously undescribed solanapyrone analogues, sphasolanapyrones A–H (18), together with four structurally related known compounds (912) were obtained from the solid fermentation of Nigrospora sphaerica MZW-A, an endophytic fungus isolated from the fresh branches of the endangered conifer Pinus wangii. This study represents the first investigation on the secondary metabolites of endophytic fungus associated with this precious plant. The structures and absolute configurations of compounds 18 were elucidated by extensive spectroscopic analysis and electronic circular dichroism (ECD) calculations. 1 and 2 are first examples of 3,4-vic diol solanapyrone analogues, whereas 7 and 8 are rare 17-nor-solanapyrones. Among these isolates, 3, 4, 5, and 11 showed weak inhibitory against Staphylococcus aureus. In addition, compound 5 displayed weak cytotoxic effects against several tumor cell lines.
本研究从 Nigrospora sphaerica MZW-A 的固体发酵产物中获得了 8 种以前未曾描述过的茄并吡喃酮类似物--sphasolanapyrones A-H (1-8),以及 4 种结构相关的已知化合物(9-12),Nigrospora sphaerica MZW-A 是一种从濒危针叶树 Pinus wangii 的新鲜枝条中分离出来的内生真菌。这项研究是首次对与这种珍贵植物相关的内生真菌的次级代谢产物进行研究。通过大量光谱分析和电子圆二色性(ECD)计算,阐明了 1-8 号化合物的结构和绝对构型。1 和 2 是 3,4-vic 二醇茄并吡喃酮类似物的第一个例子,而 7 和 8 则是罕见的 17-去甲茄并吡喃酮。在这些分离物中,3、4、5 和 11 对金黄色葡萄球菌有微弱的抑制作用。此外,化合物 5 对几种肿瘤细胞株有微弱的细胞毒性作用。
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引用次数: 0
Two new abietane diterpenoids from Caryopteris trichosphaera Caryopteris trichosphaera 中的两种新的abietane diterpenoids。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-23 DOI: 10.1016/j.fitote.2024.106269
Qing-Yu Lu , Zhao-Jie Wang , Li-Yu Bai , Wen-Biao Zu , Zhong-Shun Zhou , Yan-Yan Zhu , Xing-Chao He , Yun-Li Zhao , Xiao-Dong Luo
Two new abietane diterpenoids, cartrisine A (1) and cartrisine B (2) were isolated from Caryopteris trichosphaera. Their structures were elucidated based on HR-ESI-MS and NMR spectral data. Compound 2 exhibited moderate antibacterial bioactivity against MRSA and VRE, and showed a strong synergistic effect with market antibiotics against MRSA and VRE.
从 Caryopteris trichosphaera 中分离出了两种新的abietane二萜类化合物,即 cartrisine A (1) 和 cartrisine B (2)。根据 HR-ESI-MS 和 NMR 光谱数据阐明了它们的结构。化合物 2 对 MRSA 和 VRE 具有中等程度的抗菌生物活性,并与市场上的抗生素对 MRSA 和 VRE 具有较强的协同作用。
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引用次数: 0
A novel normonoterpene glycoside and a new benzophenone derivative from Hypericum cerastioides and their in vitro cytotoxic activities 来自贯叶连翘的一种新的常萜苷和一种新的二苯甲酮衍生物及其体外细胞毒性活性。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-23 DOI: 10.1016/j.fitote.2024.106276
Rima Konya Konuk , Başak Aru , Ceren Öztürk , Hasan Kırmızıbekmez
Phytochemical investigations on the aerial parts of Hypericum cerastioides led to the isolation and identification of a novel normonoterpene (1) and a previously undescribed benzophenone glycoside (3) along with eleven known secondary metabolites (2, 413). Their structures were deduced based on extensive 1D and 2D NMR analyses as well as HRESIMS. Compound 1 is a rare type of normonoterpene derivative with eight carbon atoms. The chemotaxonomic significance of the isolates was also discussed. Compounds were evaluated for their in vitro cytotoxic activities against SW480, A375, DU145 and MCF7 cancer cell lines using doxorubicin as a reference drug. Compounds 1 and 7 demonstrated weak cytotoxicity.
通过对贯叶连翘(Hypericum cerastioides)气生部分的植物化学研究,分离并鉴定出了一种新型常萜类化合物(1)和一种之前未曾描述过的二苯甲酮苷(3),以及 11 种已知的次级代谢产物(2、4-13)。根据大量的一维和二维核磁共振分析以及 HRESIMS,推断出了它们的结构。化合物 1 是一种罕见的具有八个碳原子的正茂萜烯衍生物。此外,还讨论了分离物的化学分类学意义。以多柔比星为参照药物,评估了化合物对 SW480、A375、DU145 和 MCF7 癌细胞株的体外细胞毒性活性。化合物 1 和 7 的细胞毒性较弱。
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引用次数: 0
Talarmalnoids A–F: Fusicoccane diterpenoids from an arthropod-derived endophytic fungus Talaromyces malicola Talarmalnoids A-F: Fusicoccane diterpenoids from an arthropod-derived endophytic fungus Talaromyces malicola.
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-23 DOI: 10.1016/j.fitote.2024.106262
Chen-yu Yang , Ke-liang Chen , Yang Liu, Xing-bao Jia, Cheng Yi, Yu-wei Niu, Ya-nan Tian, Yun-bao Liu
The metabolites from the endophytic fungus Talaromyces malicola hosted in the gastrointestinal tract of the arthropods Armadillidium vulgare were investigated, and six undescribed fusicoccane diterpenoids, talarmalnoids A–F (16), along with three known analogs were isolated. Talarmalnoid C (3) was an unprecedented fusicoccane diterpenoid with two sugar units, i.e., 6-O-methyl-α-d-glucose and α-d-glucose. Talarmalnoids D and E (4 and 5) were fusicoccane-type diterpenoids with unusual seven-membered rings attached at the C-3′ and C-4′ positions. Their structures and absolute configurations were identified by NMR, HRESIMS analyses, X-ray single crystal diffraction, GC–MS, ECD analyses, 13C NMR calculations, and DP4+ probability analyses. Bioassay results showed that talarmalnoid B (2) exhibited significant inhibitory activities against the LPS-inducted production of NO in RAW 264.7 cells, with IC50 value of 0.83 μM.
研究人员对寄生在节肢动物犰狳胃肠道中的内生真菌 Talaromyces malicola 的代谢物进行了调查,并分离出了六种未曾描述过的 fusicoccane 二萜,即 Talarmalnoids A-F(1-6),以及三种已知的类似物。Talarmalnoids C(3)是一种前所未有的含有两个糖单位(即 6-O-甲基-α-d-葡萄糖和α-d-葡萄糖)的草杉烷二萜类化合物。Talarmalnoids D 和 E(4 和 5)是在 C-3' 和 C-4' 位置上连接有不寻常的七元环的 fusicoccane 型二萜类化合物。通过核磁共振、HRESIMS 分析、X 射线单晶衍射、气相色谱-质谱、ECD 分析、13C 核磁共振计算和 DP4+ 概率分析,确定了它们的结构和绝对构型。生物测定结果表明,talarmalnoid B (2) 对 RAW 264.7 细胞在 LPS 诱导下产生的 NO 具有显著的抑制活性,IC50 值为 0.83 μM。
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引用次数: 0
New chalcone derivatives containing morpholine-thiadiazole: Design, synthesis and evaluation of against tobacco mosaic virus 含有吗啉-噻二唑的新查尔酮衍生物:针对烟草花叶病毒的设计、合成和评估。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-22 DOI: 10.1016/j.fitote.2024.106272
Wei Zeng, Zhiling Sun, Yufang Zhang, Yuzhi Hu, Qing Zhou, Yujiao Qiu, Jieyu Li, Wei Xue
Twenty chalcone derivatives containing morpholine-thiadiazole were designed and synthesized from the natural product chalcone. The bioactivity test results indicate that some compounds exhibit good antiviral activity against tobacco mosaic virus (TMV). In particular, the EC50 values for the curative and protective activity of S14 against TMV were 91.8 and 130.6 μg/mL, which was better than that of the antiviral agent ningnanmycin (NNM, 237.8, 220.6 μg/mL). The results of preliminary mechanism study indicated that S14 had strong binding capacity and affinity to tobacco mosaic virus coat protein (TMV-CP). In the chlorophyll content assay, the chlorophyll content of tobacco leaves increased significantly after the action of S14, so that it can enhance the photosynthetic capacity of plants. In addition, the results of malondialdehyde (MDA) content assay also indicated that S14 could improve the disease resistance of tobacco.
从天然产物查尔酮中设计并合成了 20 个含有吗啉-噻二唑的查尔酮衍生物。生物活性测试结果表明,一些化合物对烟草花叶病毒(TMV)具有良好的抗病毒活性。其中,S14 对 TMV 的治疗活性和保护活性的 EC50 值分别为 91.8 和 130.6 μg/mL,优于抗病毒药物宁南霉素(NNM,237.8、220.6 μg/mL)。初步机理研究结果表明,S14 与烟草花叶病毒衣壳蛋白(TMV-CP)具有很强的结合能力和亲和力。在叶绿素含量测定中,S14 作用后烟草叶片的叶绿素含量显著增加,因此它能增强植物的光合能力。此外,丙二醛(MDA)含量测定结果也表明,S14 能提高烟草的抗病性。
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引用次数: 0
Triterpenoids from the rhizomes and roots of Gentiana scabra Bge. and their cytotoxic activities Gentiana scabra Bge.根茎和根中的三萜类化合物及其细胞毒活性。及其细胞毒性活性。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-22 DOI: 10.1016/j.fitote.2024.106268
Guan-Ke Liu , Bing-Yang Zhang , Zheng Niu , Jia-Qi Chen , Chun-Yu Fan , Xin-Yue Deng , Fan-Qing Ye , Shi-Jie Cao , Ning Kang , Tie Yao , Feng Qiu
Phytochemical investigation on the rhizomes and roots of Gentiana scabra (Gentianaceae) led to the isolation of five new triterpenoids (15), together with seven known ones (612). The structures and absolute configurations of the new compounds were elucidated by spectroscopic data interpretation, ECD calculation and X-ray crystallographic analysis. Noticeably, compound 4 was an uncommon 3,4-seco-pentacyclic triterpenoid in natural products. The in vitro cytotoxic activities of all isolates against human cancer cell lines (HepG2, Hep3B, HCT116, and U87) were measured using MTT assay. Among them, compounds 29, 11, and 12 exhibited anti-proliferative effects against these tumor cell lines.
通过对龙胆科植物 Gentiana scabra 的根茎和根部进行植物化学研究,分离出了五种新的三萜类化合物(1-5)以及七种已知的三萜类化合物(6-12)。通过光谱数据解读、ECD 计算和 X 射线晶体学分析,阐明了新化合物的结构和绝对构型。值得注意的是,化合物 4 是天然产物中不常见的 3,4-共五环三萜类化合物。所有分离物对人癌细胞株(HepG2、Hep3B、HCT116 和 U87)的体外细胞毒性活性均采用 MTT 法进行了测定。其中,化合物 2-9、11 和 12 对这些肿瘤细胞株具有抗增殖作用。
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引用次数: 0
The medicinal plant Peucedanum japonicum Thunberg: A review of traditional use, phytochemistry, and pharmacology 药用植物 Peucedanum japonicum Thunberg:传统用途、植物化学和药理学综述。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-21 DOI: 10.1016/j.fitote.2024.106270
Tran Quang Hai , Nguyen Thi Huong , Ninh The Son
Peucedanum japonicum (the family Umbelliferae) is a perennial herbaceous plant with various crucial traditional values for coughs, colds, headaches, and inflammatory responses. For drug developments, the current research aims to offer an overview of the previous results in the three main aspects of traditional use, phytochemistry, pharmacological values, and molecular mechanisms regarding this medicinal species. By chromatographic analysis and separation, more than 120 isolated compounds have been obtained. Khellactone-type coumarins and phenolic compounds are the primary phytochemical classes with some coumarins, such as calipteryxin, praerutorin A, and pteryxin, being the main metabolites. Pharmacological activities of P. japonicum constituents included anticancer, antioxidative, antimicrobial, antiviral, antiplatelet, and tyrosine inhibitory activities, especially anti-inflammation and anti-obesity. It is worth mentioning that the obtained constituents joined to protect the neurons, bone, and urine systems, and exerted vasorelaxant. In general, the underlying mechanism of anti-inflammatory action can be explained by mitogen-activated protein kinase/nuclear factor-kappa B (MAPK/NF-κB) signaling pathway, whereas anti-obesity activity is deduced from regulating lipid metabolism-related genes. It also noted that pteryxin is the most active compound, but the clinical studies and synthesis of new derivatives containing enhanced medicinal values have been still limited, which should be improved.
Peucedanum japonicum(伞形科)是一种多年生草本植物,具有治疗咳嗽、感冒、头痛和炎症反应的各种重要传统价值。为了开发药物,目前的研究旨在从传统用途、植物化学、药理价值和分子机制三个主要方面概述有关该药用植物的以往成果。通过色谱分析和分离,共分离出 120 多种化合物。主要的植物化学成分为黄柏酮类香豆素和酚类化合物,其中一些香豆素类化合物,如萼片香豆素、praerutorin A 和 pteryxin 是主要的代谢产物。日本鸦胆子成分的药理活性包括抗癌、抗氧化、抗菌、抗病毒、抗血小板和酪氨酸抑制活性,尤其是抗炎和抗肥胖活性。值得一提的是,所获得的成分还能保护神经元、骨骼和尿液系统,并起到舒张血管的作用。一般来说,抗炎作用的基本机制可通过丝裂原活化蛋白激酶/核因子-卡巴B(MAPK/NF-κB)信号通路来解释,而抗肥胖活性则可通过调节脂质代谢相关基因来推导。研究还指出,翼苷是活性最高的化合物,但临床研究和合成药用价值更高的新衍生物仍然有限,有待改进。
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引用次数: 0
A strategic review of STAT3 signaling inhibition by phytochemicals for cancer prevention and treatment: Advances and insights 植物化学物质抑制 STAT3 信号以预防和治疗癌症的战略综述:最新进展。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-20 DOI: 10.1016/j.fitote.2024.106265
Suryaa Manoharan, Ekambaram Perumal
Cancer remains a significant global health concern. The dysregulation of signaling networks in tumor cells greatly affects their functions. This review intends to explore phytochemicals possessing potent anticancer properties that specifically target the STAT3 signaling pathway, elucidating strategies and emphasizing their potential as promising candidates for cancer therapy. The review comprehensively examines various STAT3 inhibitors designed to disrupt the signaling cascade, including those targeting upstream activation, SH2 domain phosphorylation, DNA binding domain (DBD), N-terminal domain (NTD), nuclear translocation, and enhancing endogenous STAT3 negative regulators. A literature review was conducted to identify phytochemicals with anticancer activity targeting the STAT3 signaling pathway. Popular research databases such as Google Scholar, PubMed, Science Direct, Scopus, Web of Science, and ResearchGate were searched from the years 1989 - 2023 based on the keywords “Cancer”, “STAT3”, “Phytochemicals”, “Phytochemicals targeting STAT3 signaling”, “upstream activation of STAT3”, “SH2 domain of STAT3”, “DBD of STAT3”, “NTD of STAT3, “endogenous negative regulators of STAT3”, or “nuclear translocation of STAT3”, and their combinations. A total of 264 relevant studies were selected and analyzed based on the mechanisms of action and the efficacy of the phytocompounds. The majority of the discussed phytochemicals primarily focus on inhibiting upstream activation of STAT3. Additionally, flavonoid and terpenoid compounds exhibit multifaceted effects by targeting one or more checkpoints within the STAT3 pathway. Analysis reveals that phytochemicals targeting upstream activation predominantly belong to the classes of flavonoids and terpenoids, which hold significant promise as effective anticancer therapeutics. Future research in this field can be directed towards exploring and developing these scrutinized classes of phytochemicals to achieve desired therapeutic outcomes in cancer treatment.
癌症仍然是全球关注的重大健康问题。肿瘤细胞信号网络的失调极大地影响了它们的功能。本综述旨在探讨专门针对 STAT3 信号通路、具有强效抗癌特性的植物化学物质,阐明相关策略,并强调它们作为癌症疗法候选药物的潜力。综述全面研究了各种旨在破坏信号级联的 STAT3 抑制剂,包括针对上游激活、SH2 结构域磷酸化、DNA 结合结构域(DBD)、N 端结构域(NTD)、核转位以及增强内源性 STAT3 负调控因子的抑制剂。为了确定针对 STAT3 信号通路具有抗癌活性的植物化学物质,我们进行了文献综述。根据关键词 "癌症"、"STAT3"、"植物化学物"、"靶向 STAT3 信号转导的植物化学物"、"STAT3 的上游激活"、"STAT3 的 SH2 结构域"、"STAT3 的 DBD"、"STAT3 的 NTD"、"STAT3 的内源性负调控因子 "或 "STAT3 的核转位 "及其组合,检索了 1989 - 2023 年期间的谷歌学者、PubMed、Science Direct、Scopus、Web of Science 和 ResearchGate 等热门研究数据库。根据植物化合物的作用机制和功效,对 264 项相关研究进行了筛选和分析。所讨论的大多数植物化学物质主要侧重于抑制 STAT3 的上游激活。此外,还有几种化合物通过靶向 STAT3 通路中的一个或多个检查点而表现出多方面的作用。分析表明,针对上游激活的植物化学物质主要属于萜类和黄酮类。针对 STAT3 上游激活的植物化学物质,尤其是萜类和黄酮类植物化学物质,有望成为有效的抗癌疗法。该领域未来的研究方向可以是进一步探索和开发这些经过仔细研究的植物化学物质类别,以在癌症治疗中取得理想的治疗效果。
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引用次数: 0
Bioactive constituents from Clerodendrum trichotomum and their α-glucosidase inhibitory and PPAR-γ agonist activities 毛蕊花的生物活性成分及其α-葡萄糖苷酶抑制剂和 PPAR-γ 激动剂活性。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-20 DOI: 10.1016/j.fitote.2024.106266
Yingbo Yang , Qian Zhang , Jia Wang , Haijun Hu , Meng Wang , Zhengtao Wang , Zhuzhen Han , Ying Xiao , Li Yang
Three new neoclerodane diterpenoids (1–3), two new steroids (4–5), one new monoterpene (6), one new derivative of benzaldehyde (7) and one new iridoid glycoside (8), along with 19 known phenolic compounds, were isolated from Clerodendrum trichotomum. Their structures were established by a combination of detailed spectroscopic analyses (1D and 2D NMR) and high resolution electrospray ionization mass spectroscopy (HRESIMS). The isolated compounds were screened on α-glucosidase inhibitory and the peroxisome proliferator-activated receptor gamma (PPAR-γ) agonist activities, and the results showed that three phenylethanoid glycosides, verbascoside (9), leucosceptoside a (10), and isoacteoside (13), and two flavonoids, apigenin (22) and luteolin (26) showed potent inhibitory effects against α-glucosidase, with IC50 values in the range from 15 to 700 μM. In addition, four flavonoids apigenin 7-O-β-D-glucuronide (19), apigenin (22), luteolin (26), and quercetin (27) exhibited significant PPAR-γ agonistic activities with EC50 values in the range 2.3–24.9 μM.
从三疣小檗中分离出了三种新的新蛇床子二萜(1-3)、两种新的甾体(4-5)、一种新的单萜(6)、一种新的苯甲醛衍生物(7)和一种新的鸢尾甙(8),以及 19 种已知的酚类化合物。通过详细的光谱分析(一维和二维核磁共振)和高分辨率电喷雾离子化质谱(HRESIMS),确定了这些化合物的结构。对分离出的化合物进行了α-葡萄糖苷酶抑制活性和过氧化物酶体增殖激活受体γ(PPAR-γ)激动活性的筛选,结果表明三种苯乙醇苷类化合物具有抑制α-葡萄糖苷酶和过氧化物酶体增殖激活受体γ(PPAR-γ)激动活性、马鞭草苷(9)、白果苷 a(10)和异内酯苷(13)以及芹菜素(22)和木犀草素(26)这两种黄酮类化合物对α-葡萄糖苷酶具有强效抑制作用,IC50 值在 15 到 700 μM 之间。此外,四种黄酮类化合物芹菜素 7-O-β-D-葡萄糖醛酸(19)、芹菜素(22)、木犀草素(26)和槲皮素(27)显示出显著的 PPAR-γ 激动活性,其 EC50 值在 2.3-24.9 μM 之间。
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引用次数: 0
Six new prenylated flavonoids from Dodonaea viscosa with anti-Zika virus activity 具有抗寨卡病毒活性的六种来自 Dodonaea viscosa 的新前基黄酮类化合物。
IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL Pub Date : 2024-10-18 DOI: 10.1016/j.fitote.2024.106264
Wen-Hui Pang , Bin-Bao Wang , Yong-Xiang Huang , Xue-Mei Zhou , Xue-Wen Wu , Muhammad Aurang Zeb , Rui-Han Zhang , Ning Huang , Xiao-Li Li , Chang-Bo Zheng , Wei-Lie Xiao
Six new prenylated flavonoids, named visconaeas A-F (1–6), and eleven known isopentenyl flavonoids (7–17) were isolated from Dodonaea viscosa (L.) Jacq. The structures of the separated compounds were determined through comprehensive spectral analysis and quantum chemical calculations. These compounds were tested for their anti-Zika virus and cytotoxicity activities. The results indicated that compound 4 showed low cytotoxicity and strong anti-Zika virus potential with EC50 16.34 μM.
从 Dodonaea viscosa (L.) Jacq 分离出六种新的前烯基黄酮类化合物,命名为 visconaeas A-F(1-6),以及十一种已知的异戊烯基黄酮类化合物(7-17)。通过综合光谱分析和量子化学计算,确定了分离出的化合物的结构。对这些化合物进行了抗寨卡病毒和细胞毒性活性测试。结果表明,化合物 4 显示出较低的细胞毒性和较强的抗寨卡病毒潜力,EC50 为 16.34 μM。
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