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Combining the Strengths of MS and NMR in Biochemometrics: A Case Study on Buddleja officinalis. 在生物化学计量学中结合 MS 和 NMR 的优势:百日草案例研究。
IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Pub Date : 2024-11-06 DOI: 10.1021/acs.jnatprod.4c00847
Andreas Wasilewicz, Alexander Areesanan, Benjamin Kirchweger, Sven Nicolay, Eva Waltenberger, Mehdi A Beniddir, Carsten Gründemann, Judith M Rollinger, Ulrike Grienke

Biochemometrics has emerged as promising strategy for the targeted identification of bioactive constituents from natural sources. It is based on the correlation of bioactivity data with chemical data to reveal constituents contributing to activity. Providing complementary data and structural information, MS- and NMR-based biochemometric approaches have both been separately applied in the past. The herein presented study is dedicated to the evaluation of a combined MS- and NMR-based biochemometric workflow for the unambiguous identification of bioactives. As an example, a flower extract of Buddleja officinalis Maxim. was selected to unravel bioactive constituents in the context of dry eye disease pathology. While NMR-based biochemometrics relies on heterocovariance analysis (HetCA) of 1H NMR spectra using the previously established ELINA approach, a biochemometric molecular network was generated for the MS-based approach. Both analyses were performed in parallel and were ultimately combined to increase their power to identify the bioactive constituents from the complex mixture. As a result, phenylethanoid glycosides and triterpene saponins were discovered as main contributors for the antioxidant and cytotoxic effects of the extract. This article illustrates the advantages, opportunities, and limitations of MS and NMR in the context of biochemometrics.

生物化学计量学已成为从天然资源中有针对性地鉴定生物活性成分的一种有前途的策略。它基于生物活性数据与化学数据的相关性,以揭示促成活性的成分。基于 MS 和 NMR 的生物化学计量方法可提供互补数据和结构信息,在过去已被分别应用。本文介绍的研究致力于对基于 MS 和 NMR 的生物化学计量工作流程进行评估,以明确鉴定生物活性成分。例如,研究人员选择了百日草花提取物来揭示干眼症病理学中的生物活性成分。基于 NMR 的生物化学计量学依赖于使用先前建立的 ELINA 方法对 1H NMR 光谱进行异方差分析 (HetCA),而基于 MS 的方法则生成了生物化学计量学分子网络。两种分析同时进行,并最终结合在一起,以提高从复杂混合物中鉴定生物活性成分的能力。结果发现,苯乙醇苷和三萜皂甙是提取物抗氧化和细胞毒性作用的主要成分。本文说明了 MS 和 NMR 在生物化学计量学方面的优势、机遇和局限性。
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引用次数: 0
Structurally Diverse Duclauxins from a Coral-Derived Talaromyces sp. and Insight into Determining the Configuration at C-1 of Heptacyclic Duclauxins by 1H NMR. 来自珊瑚衍生的塔拉酵母菌的结构多样的杜鹃花素,以及通过 1H NMR 确定七环杜鹃花素 C-1 构型的启示。
IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Pub Date : 2024-11-04 DOI: 10.1021/acs.jnatprod.4c00709
Hanxiao Zeng, Yaxing Wang, Chenyang Wang, Yahui Huang, Shuang Lin, Jiangchun Wei, Weiguang Sun, Fei Cao, Yonghui Zhang, Zhengxi Hu

A chemical investigation of the coral-derived fungus Talaromyces sp. TJ403-AL05 led to the isolation of 18 duclauxin analogues (1-18), 14 of which, taladuxins A-N (1-14), are new and consist of the first example of duclauxin fused with one 1,6-dioxaspiro[4.5]decan-2-one moiety (1), as well as its biosynthetic product (2), and 12 6/6/6/5/6/6/6 heptacyclic derivatives (3-14). Comprehensive spectroscopic analyses, electronic circular dichroism (ECD) calculations, DP4+ probability analyses, single-crystal X-ray diffraction, and vibrational circular dichroism (VCD) calculations were employed to characterize their structures and revise the published structure of verruculosin B. An efficient 1H NMR method was established to discriminate 1R and 1S configurations at C-1 of 6/6/6/5/6/6/6 heptacyclic duclauxins according to chemical shift differences of diastereotopic methylene H2-11 or H2-12 (ΔδH-11 or ΔδH-12). Compounds 4, 7-8, 13-15, and 18 exhibited moderate inhibition of Arabidopsis thaliana 4-hydroxyphenylpyruvate dioxygenase (AtHPPD), with IC50 values ranging from 17.1 to 71.3 μM.

通过对珊瑚源真菌 Talaromyces sp. TJ403-AL05 进行化学研究,分离出了 18 种杜冷丁类似物 (1-18),其中 14 种为 taladuxins A-N (1-14),它们都是新化合物,包括第一个融合了一个 1,6-dioxaspiro[4.5]癸烷-2-酮分子(1)及其生物合成产物(2),以及 12 种 6/6/6/5/6/6 七环衍生物(3-14)。研究人员通过综合光谱分析、电子圆二色性(ECD)计算、DP4+概率分析、单晶 X 射线衍射和振动圆二色性(VCD)计算,确定了这些衍生物的结构特征,并修正了已公布的verruculosin B 的结构。根据非对映同位素亚甲基 H2-11 或 H2-12(ΔδH-11 或 ΔδH-12)的化学位移差异,建立了一种高效的 1H NMR 方法来区分 6/6/6/5/6/6 七环杜仲苷 C-1 的 1R 和 1S 构型。化合物 4、7-8、13-15 和 18 对拟南芥 4-羟基苯丙酮酸二加氧酶(AtHPPD)有中等程度的抑制作用,IC50 值在 17.1 到 71.3 μM 之间。
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引用次数: 0
Doubly Homologated Tyrosine-Containing Peptides from the Cyanobacterium Microcystis aeruginosa NIES-4285 and Their Biosynthesis. 来自铜绿微囊藻 NIES-4285 蓝藻的双同源含酪氨酸肽及其生物合成。
IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Pub Date : 2024-10-30 DOI: 10.1021/acs.jnatprod.4c00972
Chin-Soon Phan, Zhengyi Ling, Jakia Jerin Mehjabin, Kenichi Matsuda, Nurcahyo Iman Prakoso, Taiki Umezawa, Toshiyuki Wakimoto, Tatsufumi Okino

Chemical investigation of the cyanobacterium Microcystis aeruginosa NIES-4285 led to the isolation of six new natural products, microginins 705 (1), 719 (2), 733A (3), 733B (4), and 733C (5), and anabaenopeptin 885 (7), and three known compounds, anabaenopeptins 871 (6), B (8), and F (9). Planar structures and absolute configurations for 1-7 were determined by 2D NMR, HRMS, and Marfey's analyses. Microginin 733C (5), and anabaenopeptins 871 (6) and 885 (7) contained a unique residue of 2-amino-5-(4-hydroxyphenyl)pentanoic acid (Ahppa): doubly homologated tyrosine (di-hTyr). The biosynthetic origin of this nonproteinogenic amino acid di-hTyr was investigated, and it was found that MaHphABCDE are involved in the production of di-hTyr. In addition, biochemical characterization of aminotransferase MaHphE showed that it is a promiscuous enzyme. This result expanded the biocatalytic toolbox for amino acid homologation.

通过对铜绿微囊藻 NIES-4285 进行化学研究,分离出了六种新的天然产物:微精素 705 (1)、719 (2)、733A (3)、733B (4) 和 733C (5),以及anabaenopeptin 885 (7),以及三种已知化合物:anabaenopeptins 871 (6)、B (8) 和 F (9)。通过二维 NMR、HRMS 和 Marfey 分析确定了 1-7 的平面结构和绝对构型。小精氨酸 733C (5)以及安纳本肽 871 (6) 和 885 (7) 含有一个独特的 2-氨基-5-(4-羟基苯基)戊酸(Ahppa)残基:双同源酪氨酸(di-hTyr)。研究人员对这种非蛋白源氨基酸 di-hTyr 的生物合成来源进行了调查,发现 MaHphABCDE 参与了 di-hTyr 的生成。此外,对转氨酶 MaHphE 的生化鉴定表明,它是一种杂合酶。这一结果扩大了氨基酸同源的生物催化工具箱。
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引用次数: 0
Natural Products with Potential for the Treatment of Pain: Global Evidence from the NAPRALERT Database. 具有治疗疼痛潜力的天然产品:来自 NAPRALERT 数据库的全球证据。
IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Pub Date : 2024-10-29 DOI: 10.1021/acs.jnatprod.4c00439
James G Graham, Jonathan Bisson, Guy H Harris, Zaijie Jim Wang, Donald P Waller, Guido F Pauli

Natural products (NPs) continue to inform the discovery and development of a diversity of drugs, both marketed and investigational. Pain, one of the most common of human experiences and profound challenges in medicine and biology, has emerged at the core of an urgent societal problem, in the United States and globally. The present study employs a retrospective analysis of an extensive set of published literature curated in the NAPRALERT database to identify NPs with experimental evidence of bioactivity supporting the selection and prioritization of NP leads with promise in pain management. The NAPRALERT pain data set currently documents >38,000 pain-relevant experiments reported in >1,750 distinct journals. The evidence presented here was annotated from >10,000 distinct scientific publications identifying NP extracts and isolates with experimental biological data indicating positive mitigation of pain, inflammation, and/or modulation of nociceptive signaling targets. Correlation of ethnomedical uses with experimental data represents a value-added approach to the selection and prioritization of leads. Dissemination of this unique NP/pain data set, with experimental data and information applicable to basic, translational, and clinical science stakeholders alike, furnishes practical evidence in support of a rational selection of NPs for directed pain research. A large portion of the NAPRALERT pain-relevant data set, along with a set of query tools designed to assist user-directed selection and prioritization of leads, are presented as Supporting Information in order to mitigate the limitations inherent in presenting such a large data set in (print) format. To support user efforts, this report involves explication of NAPRALERT data organization and the articulation of rational approaches to user-guided selection of evidence-based NP leads.

天然产品(NPs)继续为市场上和研究中的多种药物的发现和开发提供信息。疼痛是人类最常见的经历之一,也是医学和生物学的深刻挑战,在美国和全球已成为一个紧迫的社会问题的核心。本研究对 NAPRALERT 数据库中整理的大量已发表文献进行了回顾性分析,以确定具有生物活性实验证据的 NPs,支持选择和优先考虑有望用于疼痛治疗的 NP 先导药物。NAPRALERT 疼痛数据集目前记录了超过 38,000 项与疼痛相关的实验,这些实验在超过 1,750 种不同期刊上进行了报道。这里介绍的证据是从超过 10,000 篇不同的科学出版物中注释出来的,这些出版物确定了具有实验生物数据的 NP 提取物和分离物,这些数据表明它们对减轻疼痛、炎症和/或调节痛觉信号靶点有积极作用。民族医学用途与实验数据的相关性代表了一种选择和优先考虑线索的增值方法。传播这套独特的 NP/疼痛数据集,以及适用于基础、转化和临床科学利益相关者的实验数据和信息,可为合理选择 NP 用于定向疼痛研究提供实用证据。NAPRALERT 疼痛相关数据集的很大一部分,以及一套旨在帮助用户指导选择和优先排序线索的查询工具,都作为佐证信息提供,以减少以(印刷)格式提供如此庞大的数据集所固有的局限性。为了支持用户的工作,本报告阐述了 NAPRALERT 的数据组织,并阐明了用户指导选择循证 NP 线索的合理方法。
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引用次数: 0
Divergent Total Synthesis of Isoflavone Natural Products and Their Potential as Therapeutic Agents for TTR Amyloidosis. 异黄酮天然产品的不同全合成及其作为 TTR 淀粉样变性治疗剂的潜力。
IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Pub Date : 2024-10-27 DOI: 10.1021/acs.jnatprod.4c00812
Nguyen Ngoc Thanh Luan, Takuya Okada, Takeshi Yokoyama, Mie Suzuki, Yuko Nabeshima, Mineyuki Mizuguchi, Naoki Toyooka

We have achieved the divergent total synthesis of nine isoflavone natural products 1-9 starting from commercially available 2,4,6-trihydroxyacetophenone as a starting material. The isoflavone skeleton of 1-9 was constructed by the Suzuki-Miyaura coupling reaction as the key reaction. Investigation of the potential of 1-9 as therapeutic agents for transthyretin (TTR) amyloidosis revealed that millexatin F (3) showed the best efficacy in ex vivo competitive binding experiments and thioflavin-T fluorescence studies. Therefore, millexatin F (3) is promising as a seed compound for a novel TTR amyloidosis therapeutic agent.

我们以市售的 2,4,6-三羟基苯乙酮为起始原料,实现了九种异黄酮天然产物 1-9 的发散全合成。1-9 的异黄酮骨架是通过关键的铃木-宫浦偶联反应构建的。对 1-9 作为治疗转甲状腺素(TTR)淀粉样变性病的潜在药物的研究表明,在体内外竞争性结合实验和硫黄素-T 荧光研究中,米力铂 F (3) 的疗效最好。因此,millexatin F (3) 有希望成为新型 TTR 淀粉样变性治疗药物的种子化合物。
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引用次数: 0
Revisiting the Cyclocephagenols via Astragalus condensatus: Structural Insights and Configurational Revision. 通过黄芪重新审视环黄芪醇:结构见解和构型修正。
IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Pub Date : 2024-10-26 DOI: 10.1021/acs.jnatprod.4c00751
Fadime Aydoğan, Pankaj Pandey, Frank R Fronczek, Daneel Ferreira, Ikhlas A Khan, Zulfiqar Ali, Amar G Chittiboyina

The phytochemical investigation of the MeOH extract of Astragalus condensatus roots led to the discovery of a new tetrahydropyran cycloartane-type triterpenoid, astracondensatol A (1), alongside six known cyclocephagenol derivatives (2, 3, 20, 32, 35, and 36). Elucidation of their structures involved 1D and 2D-NMR spectroscopy and mass data analysis. Upon comparing NMR spectroscopic data with prior literature, several carbon shift anomalies, particularly at C-24, prompted a reevaluation using quantum chemical calculations, resulting in the revision of the 24S to 24R absolute configuration for compound 2 and 38 other reported cyclocephagenol-type triterpenoids. X-ray crystallography data further supported the analysis in establishing the absolute configuration of compound 2. Ambiguous NOE correlations and publication bias could have played a significant role in miss-assigning the C-24 absolute configuration in tetrahydropyran cycloartane-type triterpenoids.

通过对黄芪根的 MeOH 提取物进行植物化学研究,发现了一种新的四氢吡喃环安坦类三萜类化合物 astracondensatol A(1),以及六种已知的环黄芪醇衍生物(2、3、20、32、35 和 36)。对它们的结构的阐明涉及一维和二维核磁共振光谱以及质量数据分析。将核磁共振光谱数据与之前的文献进行比较后,发现了几个碳位移异常点,尤其是 C-24 碳位移异常点,这促使我们使用量子化学计算方法对其进行了重新评估,从而将化合物 2 和其他 38 种已报道的环石竹烯醇型三萜类化合物的绝对构型从 24S 修改为 24R。X 射线晶体学数据进一步支持了确定化合物 2 绝对构型的分析。不明确的 NOE 相关性和出版偏差可能在错误指定四氢吡喃环安坦类三萜化合物的 C-24 绝对构型方面起了重要作用。
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引用次数: 0
Comprehensive Cell Biological Investigation of Cytochalasin B Derivatives with Distinct Activities on the Actin Network. 对肌动蛋白网络具有不同活性的细胞分裂素 B 衍生物进行全面的细胞生物学研究。
IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Pub Date : 2024-10-25 Epub Date: 2024-10-11 DOI: 10.1021/acs.jnatprod.4c00676
Mervic D Kagho, Katharina Schmidt, Christopher Lambert, Thomas Kaufmann, Lili Jia, Jan Faix, Klemens Rottner, Marc Stadler, Theresia Stradal, Philipp Klahn

In search of a more comprehensive structure-activity relationship (SAR) regarding the inhibitory effect of cytochalasin B (2) on actin polymerization, a virtual docking of 2 onto monomeric actin was conducted. This led to the identification of potentially important functional groups of 2 (i.e., the NH group of the isoindolone core (N-2) and the hydroxy groups at C-7 and C-20) involved in interactions with the residual amino acids of the binding pocket of actin. Chemical modifications of 2 at positions C-7, N-2, and C-20 led to derivatives 3-6, which were analyzed for their bioactivities. Compounds 3-5 exhibited reduced or no cytotoxicity in murine L929 fibroblasts compared to that of 2. Moreover, short- and long-term treatments of human osteosarcoma cells (U-2OS) with 3-6 affected the actin network to a variable extent, partially accompanied by the induction of multinucleation. Derivatives displaying acetylation at C-20 and N-2 were subjected to slow intracellular conversion to highly cytotoxic 2. Together, this study highlights the importance of the hydroxy group at C-7 and the NH function at N-2 for the potency of 2 on the inhibition of actin polymerization.

为了就细胞松弛素 B(2)对肌动蛋白聚合的抑制作用寻求更全面的结构-活性关系(SAR),我们对 2 与单体肌动蛋白进行了虚拟对接。结果发现了 2 的潜在重要官能团(即异吲哚酮核心的 NH 基团(N-2)以及 C-7 和 C-20 位置的羟基),这些官能团参与了与肌动蛋白结合袋残余氨基酸的相互作用。对 2 的 C-7、N-2 和 C-20 位进行化学修饰后,得到了衍生物 3-6,并对其生物活性进行了分析。此外,用 3-6 对人骨肉瘤细胞(U-2OS)进行短期和长期处理时,肌动蛋白网络会受到不同程度的影响,部分影响还伴随着多核诱导。在 C-20 和 N-2 处显示乙酰化的衍生物会在细胞内缓慢转化为具有高度细胞毒性的 2。总之,这项研究强调了 C-7 处的羟基和 N-2 处的 NH 功能对 2 抑制肌动蛋白聚合的效力的重要性。
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引用次数: 0
Immunosuppressive Breviane Spiroditerpenoids from Penicillium bialowiezense Isolated from a Medicinal Plant. 从一种药用植物中分离出的青霉 Bialowiezense 中提取的具有免疫抑制作用的 Breviane 疏螺旋体。
IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Pub Date : 2024-10-25 Epub Date: 2024-10-09 DOI: 10.1021/acs.jnatprod.4c00782
Shu-Shuai Chen, Yuan Gao, Li Chen, Xiao Tong, Pei-Qian Wu, Yi Huang, Shi-Jun He, Jian-Min Yue, Bin Zhou

Breviane spiroditerpenoids are a small group of structurally interesting and complex meroterpenoids. This work focused on an endophytic fungus Penicillium bialowiezense ZBWPQ-27 that was isolated from a medicinal plant Euphorbia neriifolia, leading to the isolation of 15 breviane spiroditerpenoids with four types of polycyclic systems (1-6 and 9-17), and two new carotane sesquiterpenoids (7 and 8). The structures including absolute configurations of the new compounds 1-8 were elucidated by spectroscopic data analysis and electronic circular dichroism (ECD) calculations. In addition, the misassigned NMR data of several resonances of the 5-methyl-TAL motif (E ring) in those of known brevianes (9-15) were corrected by spectroscopic data analysis. Biological tests revealed that brevianes with the type A ring system (6/6/6/5/6) showed moderate to significant immunosuppressive activities, and compound 11 displayed the most potent inhibitory activities against concanavalin A (ConA)-induced T cell proliferation (IC50 4.1 ± 0.2 μM) and lipopolysaccharide (LPS)-induced B cell proliferation (IC50 4.6 ± 0.2 μM), with good SI values of 28 ± 2 and 25 ± 4, respectively.

Breviane spiroditerpenoids 是一小群结构有趣而复杂的 meroterpenoids。这项研究的重点是从药用植物大戟(Euphorbia neriifolia)中分离出的一种内生真菌青霉菌(Penicillium bialowiezense ZBWPQ-27)中分离出了 15 种含有四种多环系统的布雷维恩螺二萜类化合物(1-6 和 9-17),以及两种新的胡萝卜烷倍半萜类化合物(7 和 8)。通过光谱数据分析和电子圆二色性(ECD)计算,阐明了新化合物 1-8 的结构(包括绝对构型)。此外,还通过光谱数据分析纠正了已知囟素化合物(9-15)中 5-甲基-TAL(E 环)图案的几个共振的错误核磁共振数据。生物测试表明,具有 A 型环系统(6/6/6/5/6)的囟素具有中等至显著的免疫抑制活性,其中化合物 11 对金刚烷胺(ConA)诱导的 T 细胞增殖(IC50 4.1 ± 0.2 μM)和脂多糖(LPS)诱导的 B 细胞增殖(IC50 4.6 ± 0.2 μM)具有最强的抑制活性,其良好 SI 值分别为 28 ± 2 和 25 ± 4。
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引用次数: 0
Total Synthesis and Structural Reassignment of the Molt-Inhibiting Marine Alkaloid Erebusinone. 蜕皮抑制性海洋生物碱依瑞布西酮的全合成与结构重定。
IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Pub Date : 2024-10-25 Epub Date: 2024-10-04 DOI: 10.1021/acs.jnatprod.4c00973
Louisa Tham, Brodie W Bulcock, Samuele Sala, Gareth L Nealon, Gavin R Flematti, Stephen A Moggach, Matthew J Piggott

The marine alkaloid erebusinone is a secondary metabolite isolated from the Antarctic sponge Isodictya erinacea. Initial biological assays have shown that erebusinone increases amphipod mortality, probably by inhibition of the biosynthesis of molting hormone (ecdysone). Herein, we report the first total synthesis of the proposed structure of erebusinone and a structural revision.

海洋生物碱艾布西酮是从南极海绵 Isodictya erinacea 中分离出来的一种次级代谢物。初步的生物学实验表明,艾瑞布西酮可能通过抑制蜕皮激素(蜕皮激素)的生物合成来增加片脚类动物的死亡率。在此,我们首次报告了艾瑞布西酮拟议结构的全合成和结构修订。
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引用次数: 0
Maydisens, Sesterterpenoids with Anti-MDR Activity from Bipolaris maydis. Maydisens, Sesterterpenoids with Anti-MDR Activity from Bipolaris maydis.
IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL Pub Date : 2024-10-25 Epub Date: 2024-10-02 DOI: 10.1021/acs.jnatprod.4c00658
Yong Shen, Nanjin Ding, Lianghu Gu, Mengru Yu, Qin Li, Weiguang Sun, Chunmei Chen, Yonghui Zhang, Hucheng Zhu

Fourteen previously undescribed sesterterpenoids (1-14) were isolated from Bipolaris maydis. Their structures with absolute configurations were elucidated by NMR, HRESIMS, DP4+ calculations, ECD calculations, single-crystal X-ray diffraction analyses, and the modified Mosher's method. Compounds 1-5 possess an uncommon 5/11 bicyclic ring system identified from B. maydis for the first time. Compounds 6-14 have a 5/8/5 tricyclic ring system, and these compounds both possess carbonyl groups in ring A. Compound 10 showed significant reversal of paclitaxel resistance in cancer cells.

从 Bipolaris maydis 中分离出了 14 种以前未曾描述过的酯类化合物(1-14)。通过核磁共振、HRESIMS、DP4+ 计算、ECD 计算、单晶 X 射线衍射分析和改进的 Mosher 方法,阐明了它们的绝对构型结构。化合物 1-5 具有不常见的 5/11 双环系统,这是首次从 B. maydis 中发现。化合物 10 显著逆转了癌细胞对紫杉醇的耐药性。
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引用次数: 0
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Journal of Natural Products
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