triterpenoids

三萜类化合物
  • 文章类型: Journal Article
    葫芦素是天然产物的三萜生物活性成分,特别是在葫芦科植物家族中。葫芦属(南瓜)种子中葫芦素的存在很少被研究。在这项工作中,葫芦素B的含量,D,和来自三个葫芦的种子油中的E(葫芦,西葫芦,和最大南瓜Linn)进行了研究。根据ICH指南,开发并验证了一种基于HPLC-DAD的分析方法,用于检测和定量种子油中的这三种葫芦素。该方法线性良好,准确度,和同时定量葫芦素B的精确度,D,和E使用C.moschata种子油作为参考。当应用于C.pepo和C.maxima种子油时,对葫芦素B和D进行了定量,但程度较低。这是第一份简单的报告,可重复,和可重现的分析工具,用于鉴定葫芦属的油籽中的葫芦素。
    Cucurbitacins are triterpene bioactive constituents of natural products, particularly in the Cucurbitaceae plant family. The presence of cucurbitacins in seeds of the Cucurbita genus (pumpkin) has been only little studied. In this work, the content of cucurbitacins B, D, and E in seed oils from three cucurbits (Cucurbita moschata Duch, Cucurbita pepo Linn, and Cucurbita maxima Linn) was studied. An analytical method based on HPLC-DAD for the detection and quantification of these three cucurbitacins in seed oils was developed and validated according to ICH guidelines. The method showed good linearity, accuracy, and precision for the simultaneous quantification of cucurbitacins B, D, and E using C.moschata seed oil as a reference. When applied to C.pepo and C.maxima seed oils, cucurbitacin B and D were quantified but to a lesser extent. This is the first report of a simple, repeatable, and reproducible analytical tool to identify cucurbitacins in oilseeds from Cucurbita spp.
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  • 文章类型: Journal Article
    足细胞损伤是糖尿病肾病(DKD)和肥胖相关性肾小球病(ORG)的常见病理机制。我们先前的研究证实,桦褐孔菌(IO)改善了DKD大鼠的足细胞损伤。目前的研究探索了药理作用,IO对ORG小鼠的相关机制及可能的活性成分。
    首先,通过超高效液相色谱-串联质谱分析(UPLC-Q-TOF-MS)与网络药理学相结合,构建人蛋白-蛋白相互作用机制,这导致发现了IO对抗ORG的关键机制。然后,通过高脂饮食和生化测定建立ORG小鼠,组织病理学,采用Westernblot方法探讨IO对肥胖及足细胞损伤的影响。最后,基于网络药理学的发现通过免疫组织化学得到证实.通过UPLC-Q-TOF-MS分析小鼠血浆中吸收的IO的组成,并使用分子对接来预测可能的活性化合物。
    网络药理学结果提示IO通过调节TNF信号减轻ORG的炎症反应。20周的体内实验证实,IO改善肾小球肥大,电镜下足细胞损伤,肾nephrin,突触素,肿瘤坏死因子-α和白细胞介素-6的表达采用免疫印迹和免疫组织化学染色。ORG的其他指标,如体重,肾脏重量,血清总胆固醇,IO干预也改善了肝脏甘油三酯。组分分析显示,三萜,包括异萜烯F和三甲烯醇酸,可能是药效学基础。
    基于UPLC-Q-TOF-MS分析的研究,网络药理学和体内实验表明,IO通过调节TNF信号改善ORG小鼠足细胞损伤。三萜类化合物被预测为作用成分。
    UNASSIGNED: Podocyte injury is a common pathologic mechanism in diabetic kidney disease (DKD) and obesity-related glomerulopathy (ORG). Our previous study confirmed that Inonotus obliquus (IO) improved podocyte injury on DKD rats. The current study explored the pharmacological effects, related mechanisms and possible active components of IO on ORG mice.
    UNASSIGNED: Firstly, by combining ultra-high performance liquid chromatography tandem mass spectrometry analysis (UPLC-Q-TOF-MS) with network pharmacology to construct the human protein-protein interaction mechanism and enrich the pathway, which led to discover the crucial mechanism of IO against ORG. Then, ORG mice were established by high-fat diet and biochemical assays, histopathology, and Western blot were used to explore the effects of IO on obesity and podocyte injury. Finally, network pharmacology-based findings were confirmed by immunohistochemistry. The compositions of IO absorbed in mice plasma were analyzed by UPLC-Q-TOF-MS and molecular docking was used to predict the possible active compounds.
    UNASSIGNED: The network pharmacology result suggested that IO alleviated the inflammatory response of ORG by modulating TNF signal. The 20-week in vivo experiment confirmed that IO improved glomerular hypertrophy, podocyte injury under electron microscopy, renal nephrin, synaptopodin, TNF-α and IL-6 expressions with Western blotting and immunohistochemical staining. Other indicators of ORG such as body weight, kidney weight, serum total cholesterol, liver triglyceride also improved by IO intervention. The components analysis showed that triterpenoids, including inoterpene F and trametenolic acid, might be the pharmacodynamic basis.
    UNASSIGNED: The research based on UPLC-Q-TOF-MS analysis, network pharmacology and in vivo experiment suggested that the amelioration of IO on podocyte injury in ORG mice via its modulation on TNF signal. Triterpenoids were predicated as acting components.
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  • 文章类型: Journal Article
    Chaga蘑菇(Inonotusobilequus)是一种致病性真菌,主要生长在桦树物种(BetulapendulaRoth和B.pubescensEhrh。),并传统上被用作抗癌药物。这项研究旨在比较两种Betulaspp上生长的chagas的化学成分和细胞毒性。在各种癌细胞系上。冻干的提取物含有三萜inotodiol,羊毛甾醇桦木醇,和桦木树种上生长的conks的典型桦木酸。通过磺基罗丹明B测定法评估了生长在白桦和毛竹芽孢杆菌80%乙醇提取物上的chaga对31种人类癌细胞系的细胞毒性活性。Chaga提取物对所有检查的癌细胞系显示中等活性;它没有导致高细胞毒性(IC50≤20µg/mL)。在HepG2和CAL-62细胞系上观察到了chaga(生长在B.pendula上)提取物和在HepG2细胞系上观察到了最强的抑制作用,IC50值为37.71、43.30和49.99μg/mL,分别。来自B.pendula的chaga提取物对所研究的大多数癌细胞系的作用强于B.pubescens提取物,这可以归因于B.pendula提取物中的inotdiol含量较高。这项研究强调了Chaga作为具有选择性抗癌特性的生物活性化合物来源的潜力。据我们所知,这项研究是对寄生在毛竹上的斜生菌化学成分的首次研究。
    Chaga mushroom (Inonotus obliquus) is a pathogenic fungus that grows mostly on birch species (Betula pendula Roth and B. pubescens Ehrh.) and has traditionally been used as an anticancer medicine. This study aimed to compare the chemical composition and cytotoxic activity of chagas growing on both Betula spp. on various cancer cell lines. The freeze-dried extracts contained triterpenes inotodiol, lanosterol betulin, and betulinic acid typical to conks growing on Betula species. The cytotoxic activity of chaga growing on Betula pendula and B. pubescens 80% ethanolic extracts against 31 human cancer cell lines was evaluated by a sulforhodamine B assay. Chaga extract showed moderate activity against all cancer cell lines examined; it did not result in high cytotoxicity (IC50 ≤ 20 µg/mL). The strongest inhibitions were observed with chaga (growing on B. pendula) extract on the HepG2 and CAL-62 cell line and with chaga (from B. pubescens) extract on the HepG2 cell line, with IC50 values of 37.71, 43.30, and 49.99 μg/mL, respectively. The chaga extracts from B. pendula exert somewhat stronger effects on most cancer cell lines studied than B. pubescens extracts, which can be attributed to a higher content of inotodiol in B. pendula extracts. This study highlights the potential of chaga as a source of bioactive compounds with selective anticancer properties. To the best of our knowledge, this study is the first investigation of the chemical composition of I. obliquus parasitizing on B. pubescens.
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  • 文章类型: Journal Article
    这项研究的目的是在糖尿病实验模型中评估三萜类化合物对糖尿病肾病发展的影响。为此,使用了脱水橄榄油(DDOO),将其效果与橄榄油(DOO)进行比较。DDOO的三萜含量高于DOO,但醇多酚含量相同。形成四个研究组(n=10只动物/组):健康大鼠,糖尿病对照大鼠(DR),和DRs用0.5mL/kg/天的DOO或DDOO口服治疗两个月。DRs显示肾功能受损(蛋白尿,血清肌酐升高,肾肌酐清除率降低)和形态(肾小球体积和肾小球硬化)。这些改变与全身和肾组织氧化应激增加和前列环素产生减少相关。DDOO给药显著降低了肾损伤的所有变量,以及全身和肾脏的氧化应激,比DOO产生的影响更大。总之,富含三萜的橄榄油可以预防实验性糖尿病的肾脏损害。
    The aim of this study was to assess the effect of triterpenoids on the development of diabetic nephropathy in an experimental model of diabetes mellitus. For this purpose, a destoned and dehydrated olive oil (DDOO) was used, comparing its effects to a destoned olive oil (DOO). DDOO had a higher triterpenoid content than DOO but an equal content of alcoholic polyphenols. Four study groups (n = 10 animals/group) were formed: healthy rats, diabetic control rats (DRs), and DRs treated orally with 0.5 mL/kg/day of DOO or DDOO for two months. DRs showed impaired renal function (proteinuria, increased serum creatinine, decreased renal creatinine clearance) and morphology (glomerular volume and glomerulosclerosis). These alterations correlated with increased systemic and renal tissue oxidative stress and decreased prostacyclin production. DDOO administration significantly reduced all variables of renal damage, as well as systemic and renal oxidative stress, to a greater extent than the effect produced by DOO. In conclusion, triterpenoid-rich olive oil may prevent kidney damage in experimental diabetes mellitus.
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  • 文章类型: Journal Article
    熊果酸(UA)及其衍生物由于其广泛的药理活性而引起了广泛的关注。UA是在多种植物中发现的五环三萜类化合物,比如苹果,迷迭香,百里香,等。,它具有一系列的药理特性。研究人员通过结构修饰合成了UA的各种衍生物,以增强其潜在的药理特性。各种体外和体内研究表明,UA及其衍生物具有多种生物活性,比如抗癌,抗真菌药,抗糖尿病药,抗氧化剂,抗菌,抗炎和抗病毒特性。这篇综述文章对UA及其衍生物的生物活性进行了综述,以显示其在治疗不同疾病中有用的有价值的治疗特性,主要关注相关的结构-活动关系(SARs),潜在的分子靶标/途径,和行动模式。
    Ursolic acid (UA) and its derivatives have garnered significant attention due to their extensive pharmacological activity. UA is a pentacyclic triterpenoid found in a variety of plants, such as apples, rosemary, thyme, etc., and it possesses a range of pharmacological properties. Researchers have synthesized various derivatives of UA through structural modifications to enhance its potential pharmacological properties. Various in vitro and in vivo studies have indicated that UA and its derivatives possess diverse biological activities, such as anticancer, antifungal, antidiabetic, antioxidant, antibacterial, anti-inflammatory and antiviral properties. This review article provides a review of the biological activities of UA and its derivatives to show their valuable therapeutic properties useful in the treatment of different diseases, mainly focusing on the relevant structure-activity relationships (SARs), the underlying molecular targets/pathways, and modes of action.
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  • 文章类型: Journal Article
    七子花的花蕾和叶/小枝的全面植物化学研究,一种原产于中国的栽培观赏植物,被归类为“脆弱”,导致分离出45种结构多样的化合物,其中包括18种苯丙素(1-4,7-20),11个五环三萜(5,6,21-29),八种环烯醚萜苷(30-37),三种奎尼酸衍生物(38-40),和一些杂项组件(41-45)。其中,(+)-α-中间醇(1),(+)-茶酚A(2),和(-)-假性木脂素A(3)代表以前未报道的对映体木脂素,而(+)-7'(R)-羟基木脂素(4)是一种未描述的天然木脂素。庚酸A(5)和B(6)是未描述的24-nor-urs-28-酸衍生物。它们的化学结构通过2D-NMR确定,由特定旋转和圆二色性光谱的证据补充。鉴于七株的系统位置存在不确定性,综合分类学(ITA),一种用来定义有争议物种的方法,是应用的。化学分类学,ITA的一个重要方面,变得重要。通过采用层次聚类分析(HCA)和同步模式分析方法,基于H.mucioides和其他两种卷叶菜科植物的花蕾的主要专门天然产物的分类学检查(即,金银花和Abelia×grandiflora)可以增强对七叶的系统放置的了解。此外,化合物39和40对ATP-柠檬酸裂解酶(ACL)表现出显著的抑制活性,IC50值为0.11和1.10μM,分别。总之,医学特性的发现和完善的系统分类可以为旨在减轻物种多样性损失同时解决人类疾病的保护工作奠定坚实的基础。
    A comprehensive phytochemical investigation of the flower buds and leaves/twigs of Heptacodium miconioides, a cultivated ornamental plant native to China and categorized as \'vulnerable\', has led to the isolation of 45 structurally diverse compounds, which comprise 18 phenylpropanoids (1-4, 7-20), 11 pentacyclic triterpenoids (5, 6, 21-29), eight secoiridoid glycosides (30-37), three quinic acid derivatives (38-40), and a few miscellaneous components (41-45). Among them, (+)-α-intermedianol (1), (+)-holophyllol A (2), and (-)-pseudolarkaemin A (3) represent previously unreported enantiomeric lignans, while (+)-7\'(R)-hydroxymatairesinol (4) is an undescribed naturally occurring lignan. Heptacoacids A (5) and B (6) are undescribed 24-nor-urs-28-oic acid derivatives. Their chemical structures were determined by 2D-NMR, supplemented by evidence from specific rotations and circular dichroism spectra. Given the uncertainty surrounding the systematic position of Heptacodium, integrative taxonomy (ITA), a method utilized to define contentious species, is applied. Chemotaxonomy, a vital aspect of ITA, becomes significant. By employing hierarchical clustering analysis (HCA) and syntenic pattern analysis methods, a taxonomic examination based on the major specialized natural products from the flower buds of H. miconioides and two other Caprifoliaceae plants (i.e., Lonicera japonica and Abelia × grandiflora) could offer enhanced understanding of the systematic placement of Heptacodium. Additionally, compounds 39 and 40 displayed remarkable inhibitory activities against ATP-citrate lyase (ACL), with IC50 values of 0.11 and 1.10 μM, respectively. In summary, the discovery of medical properties and refining systematic classification can establish a sturdy groundwork for conservation efforts aimed at mitigating species diversity loss while addressing human diseases.
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  • 文章类型: Journal Article
    人参,亚洲传统草药的基石,它的治疗潜力引起了极大的关注。其药理作用的核心是人参皂苷,主要的活性代谢物,其中许多属于达玛烷型,并共享原人参二醇作为常见前体。从人参中提取原人参二醇和人参皂苷的挑战是由于它们在根中的低浓度。新兴的解决方案涉及利用采用基因工程酵母的微生物细胞工厂。这里,通过实验设计优化了发酵条件,在简单的摇瓶培养中实现1.2g/L原人参二醇。将优化的设置外推至复杂的人参皂苷,像化合物K,实现了7.3倍(0.22g/L)的滴度提高。我们适应性强的发酵条件能够生产高价值产品,如可持续的三萜类合成。通过合成生物学,微生物工程,和配方研究,我们为人参生物活性化合物的可扩展和可持续生产铺平了道路。
    Ginseng, a cornerstone of traditional herbal medicine in Asia, garnered significant attention for its therapeutic potential. Central to its pharmacological effects are ginsenosides, the primary active metabolites, many of which fall within the dammarane-type and share protopanaxadiol as a common precursor. Challenges in extracting protopanaxadiol and ginsenosides from ginseng arise due to their low concentrations in the roots. Emerging solutions involve leveraging microbial cell factories employing genetically engineered yeasts. Here, we optimized the fermentation conditions via the Design of Experiment, realizing 1.2 g/L protopanaxadiol in simple shake flask cultivations. Extrapolating the optimized setup to complex ginsenosides, like compound K, achieved 7.3-fold (0.22 g/L) titer improvements. Our adaptable fermentation conditions enable the production of high-value products, such as sustainable triterpenoids synthesis. Through synthetic biology, microbial engineering, and formulation studies, we pave the way for a scalable and sustainable production of bioactive compounds from ginseng.
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  • 文章类型: Journal Article
    桃(Prunuspersica)对昆虫攻击的防御反应涉及基因表达和代谢产物的变化。刺入/吸吮昆虫,如青桃蚜虫,通过获取韧皮部营养造成直接损害,通过传播植物病毒造成间接损害。为了研究桃树对蚜虫的反应,对绿桃蚜虫具有不同敏感性的两种基因型的叶片转录组和代谢组(GPA,对Myzuspersicae)进行了研究。感染桃叶的转录组分析显示出两种不同的反应模式。蚜虫侵染的对蚜虫易感桃植株的基因表达与对照植株较为相似,而与对照植物相比,被蚜虫感染的抗蚜虫桃植物的基因表达显示出强烈诱导的基因表达变化。此外,防御相关途径中的基因转录本,包括植物-病原体相互作用,MAPK信号,和几种代谢途径,在蚜虫侵染后更强烈地富集。非靶向次生代谢产物分析证实,蚜虫治疗在抗蚜虫的桃子中引起的变化要大于对蚜虫易感的桃子。与转录组改变一致,九种三萜类化合物在抗蚜虫桃中表现出极显着的GPA诱导积累,而三萜丰度在蚜虫易感桃中主要保持不变或未检测到。此外,某些类型的转录因子(包括WRKYs,ERF,NAC,等。)在抗蚜虫桃中的GPA侵染后,而在对蚜虫易感的桃中则没有引起。蚜虫摄食依赖性转录组和代谢物谱为了解桃子对蚜虫侵染反应的分子机制奠定了基础。这些结果表明,特殊的三萜类化合物和相应的途径转录物的积累可能在桃GPA抗性中起关键作用。
    The defense response of peach (Prunus persica) to insect attack involves changes in gene expression and metabolites. Piercing/sucking insects such as green peach aphid cause direct damage by obtaining phloem nutrients and indirect damage by spreading plant viruses. To investigate the response of peach trees to aphids, the leaf transcriptome and metabolome of two genotypes with different sensitivities to green peach aphid (GPA, Myzus persicae) were studied. The transcriptome analysis of infected peach leaves showed two different response patterns. The gene expression of aphid-susceptible peach plants infected by aphids was more similar to that of the control plants, while the gene expression of aphid-resistant peach plants infected by aphids showed strongly induced changes in gene expression compared with the response in the control plants. Furthermore, gene transcripts in defense-related pathways, including plant-pathogen interaction, MAPK signaling, and several metabolic pathways, were more strongly enriched upon aphid infestation. Untargeted secondary metabolite profiling confirmed that aphid treatment induced larger changes in aphid-resistant peaches than in aphid-susceptible peaches. Consistent with transcriptomic alterations, nine triterpenoids showed extremely significant GPA-induced accumulation in aphid-resistant peaches, whereas triterpenoid abundance remained predominantly unchanged or undetected in aphid- susceptible peaches. Furthermore, some types of transcription factors (including WRKYs, ERFs, NACs, etc.) were more strongly induced upon GPA infestation in aphid-resistant peaches but not in aphid-susceptible peaches. Aphid feeding-dependent transcriptome and metabolite profiles provide the foundation for understanding the molecular mechanisms underlying the response of peach to aphid infestation. These results suggested that accumulation of specialized triterpenoids and the corresponding pathway transcripts may play a key role in peach GPA resistance.
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  • 文章类型: Journal Article
    12-α-氟-3β-羟基-布尔-28,13β-醇甲醇半隔离物的X射线晶体结构数据,2C30H47FO3·CH3OH,(1),和12-α-氟-3β-羟基-taraxer-28,14β-内酯甲醇半隔离物,2C30H47FO3·CH3OH,(2),被描述。在甲基C-27从C-14向C-13转移1,2-之后,使用SelectfluroTM对齐墩果酸进行氟内酯化,得到了六元δ-内酯(1)和不寻常的七元γ-内酯(2)的混合物。
    The X-ray crystal structure data of 12-α-fluoro-3β-hy-droxy-olean-28,13β-olide methanol hemisolvate, 2C30H47FO3·CH3OH, (1), and 12-α-fluoro-3β-hy-droxy-taraxer-28,14β-olide methanol hemisolvate, 2C30H47FO3·CH3OH, (2), are described. The fluoro-lactonization of oleanolic acid using SelectfluorTM yielded a mixture of the six-membered δ-lactone (1) and the unusual seven-membered γ-lactone (2) following a 1,2-shift of methyl C-27 from C-14 to C-13.
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  • 文章类型: Journal Article
    灵芝(柯蒂斯)P.喀斯特。(G.灵芝)是一种真菌,这也是一种在中国用于“智慧成长”的传统中药。灵芝三萜类化合物(GLTs)是主要活性成分之一。基于阿尔茨海默病(AD)的早期干预策略以及肠道菌群紊乱和代谢产物与AD的密不可分,本研究旨在借助网络药理学,探讨GLTs通过微生物群-肠-脑轴保护AD的机制。在这项研究中,LC-MS/MS用于鉴定GLTs的主要活性成分。使用网络药理学来预测潜在的靶标,并用Caco-2细胞模型进行验证。D-半乳糖用于诱导大鼠慢发型AD。利用基于GC-MS的代谢组学方法结合16SrRNA测序技术进行微生物群-肠道代谢组学分析,以揭示GLTs在AD保护中的潜在机制。作为结果,通过干预给药,GLTs对大鼠显示出针对AD的保护作用。这些机制与GLTs干扰肠道微生物群和代谢物的平衡密不可分。涉及的主要粪便代谢产物是短链脂肪酸和芳香族氨基酸代谢产物。
    Ganoderma lucidum (Curtis) P. Karst.(G. lucidum) is a kind of fungi, which also a traditional Chinese medicine used for \"wisdom growth\" in China. Triterpenoids from G. lucidum (GLTs) are one of the main active ingredients. Based on the strategy of early intervention on Alzheimer\'s disease (AD) and the inextricable association between disordered gut microbiota and metabolites with AD, this study aimed to explore the mechanisms of GLTs in the protection against AD via microbiota-gut-brain axis with the aid of network pharmacology. In this study, LC-MS/MS was used to identify the main active ingredients of GLTs. Network pharmacology was used to predict the potential target and validated with Caco-2 cell model. D-galactose was used to induce the slow-onset AD on rats. Metabolomics methods basing on GC-MS combined with 16S rRNA sequencing technology was used to carry out microbiota-gut-metabolomics analysis in order to reveal the potential mechanisms of GLTs in the protection of AD. As results, GLTs showed a protection against AD effect on rats by intervening administration. The mechanisms were inextricably linked to GLTs interference with the balance of gut microbiota and metabolites. The main fecal metabolites involved were short-chain fatty acids and aromatic amino acid metabolites.
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