A new ent-labdane diterpenoid lactone from Andrographis paniculata

A new ent-labdane diterpenoid lactone was isolated from Andrographis paniculata.Its structure was identified on the basis of spectral data including 2D NMR.

A new ent-labdane diterpenoid from Andrographis paniculata

新 ent-labdane diterpenoid， 19-O- 尾 - d-glucopyranosyl-ent-labda-8 (17 ) ，和六已知的 ent-labdane diterpenoids， 13-dien-15,16,19-triol 从 Andrographis paniculata 的天线部分被孤立。新混合物的结构被阐明由广泛光谱分析。

Insight of Natural Compounds Halimane Diterpenoids against Mycobacterium tuberculosis: Virtual Screening, DFT, Drug-Likeness, and Molecular Dynamics Approach

In the purpose to design novel antituberculosis (anti-TB) drugs agents against Mycobacterium tuberculosis (Mtb), we have built a molecular library around 42 Halimane Diterpenoids isolated from natural sources. Two Mtb enzymes drug targets (Mtb Mycothiol S-transferase and Mtb Homoserine transacetylase) have been adopted. The pharmacological potential was investigated through molecular docking, molecular dynamics simulation, density functional theory (gas phase and water) and ADMET analysis. Our results indicate that (2R,5R,6S)-1,2,3,4,5,6,7,8-octahydro-5-((E)-5-hydroxy-3-methylpent-3-enyl)-1,1,5,6-tetramethylnaphtha-lene-2-ol (compound 20) has displays higher docking score with each of the selected drug targets. In addition, this molecule exhibits a satisfactory drug potential activity and a good chemical reactivity. Its improved kinetic stability in the Mtb Mycothiol S-transferase enzyme reflects its suitability as a novel inhibitor of Mtb growth. This molecule has displayed a good absorption potential. Our results also show that its passive passage of the intestinal permeability barrier is more effective than that of first-line treatments (ethambutol, isoniazid). In the same way, this anti-TB druglikeness has shown to be able to cross the blood brain barrier.

A new ent-labdane eiterpenoid lactone from Andrographis paniculata

A new ent-labdane diterpenoid lactone with a new natural product was isolated from Andrographis paniculata. Their structures were elucidated on the basis of spectral evidences including 2D NMR.

醋乳香现代研究进展及质量标志物的预测

醋乳香是乳香Olibanum经醋炙法加工后的炮制品,炮制后可除去部分挥发油成分,消除其对胃黏膜的刺激性,同时能引药入经增强活血止痛、收敛生肌等功效。通过总结文献报道,从醋炙后化学成分与功效变化,刺激性研究,成分特有性、有效性、可测性,配伍环境及体内过程相关性等方面对醋乳香的质量标志物(Q-marker)进行预测分析,初步确定3-乙酰基-9,11-去氢-β-乳香酸、3-乙酰基-α-乳香酸、3-乙酰基-β-乳香酸、11-羰基-β-乳香酸、11-羰基-β-乙酰乳香酸5个三萜类成分和挥发油类成分乙酸辛酯为其可能的Q-marker,以期为醋乳香的全程质量评价、临床应用研究提供理论依据。

马醉木二萜成分及其乙酰胆碱酯酶抑制活性研究

为研究马醉木叶中的二萜成分及其乙酰胆碱酯酶抑制活性,该研究根据薄层色谱显色特征,使用硅胶、MCI和半制备高效液相等色谱技术对其进行分离与纯化,并通过波谱数据(NMR和MS)分析且结合文献报道数据进行对比,鉴定了所得化合物的结构,同时采用Ellman法首次对其乙酰胆碱酯酶抑制活性进行评价。结果表明:从马醉木叶中分离并鉴定了8个二萜化合物,分别是pierisformoside F(1)、3-epi-grayanotoxinⅩⅧ(2)、3-epi-grayanotoxin B(3)、asebotoxin-X(4)、pierisformosin B(5)、asebotoxinⅢ(6)、rhodojaponinⅢ(7)和pierisformosin C(8)。其中,化合物1为首次从该植物中分离得到,化合物8表现出乙酰胆碱酯酶抑制活性。综上表明,马醉木中含有丰富的二萜成分和活性成分。该研究结果丰富了马醉木的化学成分多样性,为其后续综合开发和利用提供了一定的理论依据,也为寻求更多的活性成分提供了借鉴。

新疆白喉乌头中4种生物碱的分离鉴定及含量测定

采用硅胶柱层析、硅胶柱色谱法等手段对白喉乌头的95%乙醇提取物中的化学成分进行了分离纯化,通过^(1)HNMR、^(13)CNMR对分离得到的4种生物碱的结构进行了鉴定,并采用HPLC法同时测定了其含量。结果表明,从白喉乌头的95%乙醇提取物中共分离得到4个二萜生物碱,分别鉴定为:8-去氧刺乌头碱、异刺乌头碱、高乌甲素、冉乌头碱,其中异刺乌头碱为首次从白喉乌头中分离得到;3批白喉乌头药材中8-去氧刺乌头碱、异刺乌头碱、高乌甲素、冉乌头碱的平均含量分别为0.026 mg·g^(-1)、0.124 mg·g^(-1)、1.143 mg·g^(-1)、0.561 mg·g^(-1),其中高乌甲素的含量最高。

苗药了哥王中瑞香烷二萜原酸酯类成分及其抗肿瘤活性研究

目的:研究苗药了哥王Wikstroemia indica(L.) C.A.Mey.中瑞香烷二萜原酸酯类成分及其抗肿瘤活性。方法:采用硅胶柱色谱、RP-C_(18)反相柱色谱、Sephadex LH-20葡聚糖凝胶柱色谱和半制备液相色谱等分离纯化技术获得了哥王中的瑞香烷二萜原酸酯类成分,再根据其理化性质和波谱数据鉴定各化合物的结构,并采用MTT法对化合物1、3、5进行抗肝癌HepG_(2)细胞株的活性评价。结果:从苗药了哥王中分离得到5个瑞香烷二萜原酸酯类化合物,分别鉴定为:6α,7α-dihydyoxyhuratoxin(1)、simplexin(2)、12β-acetoxyhuratoxin(3)、excoecafolin D(4)、pimelea factor P_(2)(5)。此类化合物对肝癌HepG_(2)细胞的增殖均有明显的抑制作用。结论:其中,化合物1为新化合物,化合物2~5为首次从该植物中分离得到,化合物3对肝癌HepG_2细胞增殖的抑制作用最佳,IC_(50)值为(5.75±0.15)μg/mL。

丹参二萜醌对顺铂的增效作用及抗肺癌相关机制研究

[目的]对活血化瘀代表药物丹参的有效成分丹参二萜醌(diterpenoid tanshinones,DT)抗肺癌进行研究,验证DT的抗肺癌效能以及其对顺铂的增效作用,并探寻DT抗肺癌的相关机制。[方法]构建A549肺癌BALB/c-nu裸鼠模型56只,根据腹腔注射及灌胃药物不同分为空白组、模型组、顺铂组、DT低剂量组、DT中剂量组、DT高剂量组、顺铂+DT高剂量组,测量并记录各组肿瘤直径,计算肿瘤体积和抑瘤率。采用免疫印迹法检测各组肿瘤组织血管内皮生长因子A(vascular endothelial growth factor A,VEGFA)、Ras、细胞周期蛋白依赖性激酶抑制剂1B(cyclin dependent kinase inhibitor 1B,CDKN1B)、Bcl-2关联X(Bcl-2 associated X,Bax)蛋白表达。采用实时荧光定量聚合酶链式反应(Real-time quantitative polymerase chain reaction,Real-time qPCR)分析维甲酸受体相关孤儿受体-γt(retinoic acid receptor-related orphan receptor-γt,ROR-γt)和转录因子叉头框蛋白P3(forkhead box protein P3,Foxp3)的变化。[结果]DT干预后的肺癌小鼠体质量上升,炎性细胞浸润好转,转移灶计数减少,瘤体积减小且抑瘤率升高,说明DT对肺癌移植瘤起到了较好的抑制作用。与空白组比较,模型组肿瘤组织中VEGFA、Ras蛋白表达水平显著升高(P<0.01),CDKN1B、Bax蛋白表达水平显著降低(P<0.01,P<0.05)。与模型组比较,顺铂组,DT低、中、高剂量组和顺铂+DT高剂量组肿瘤组织中VEGFA、Ras蛋白表达水平降低(P<0.01),CDKN1B、Bax蛋白表达水平升高(P<0.01,P<0.05),其中顺铂+DT高剂量组致癌基因表达降低和抑癌基因表达升高程度最为明显(P<0.01)。与顺铂组比较,顺铂+DT高剂量组VEGFA、Ras表达有所降低,CDKN1B、Bax表达有所升高,但差异无统计学意义(P>0.05)。DT剂量越高,致癌基因的表达水平越低,抑癌基因的表达水平越高,但差异无统计学意义(P>0.05)。Real-time qPCR显示,与空白组比较,模型组肿瘤组织中ROR-γt和Foxp3的表达水平显著升高(P<0.01)。与模型组比较,顺铂组,DT低、中、高剂量组和顺铂+DT高剂量组肿瘤组织中ROR-γt和Foxp3表达水平降低(P<0.01,P<0.05),其中顺铂+DT高剂量组ROR-γt和Foxp3表达下降最明显(P<0.01)。DT剂量越高,ROR-γt和Foxp3的表达水平越低,但差异无统计学意义(P>0.05)。[结论]DT具有较为可靠的抗肺癌效能,且这种效能具备剂量依赖性;DT与顺铂联用有增强顺铂抗肿瘤疗效的趋势。

半枝莲抗肝癌活性部位的化学成分研究

前期研究发现,半枝莲(Scutellaria barbata)全草醇提物的乙酸乙酯萃取部位经大孔吸附树脂处理,其70%乙醇洗脱部位具有较好的抗肝癌活性。为明确其活性成分,该研究采用硅胶柱色谱、Sephadex LH-20柱色谱、制备TLC、半制备液相色谱等对活性部位进行分离和纯化,运用多种波谱分析方法鉴定了单体化合物结构,并利用CCK-8法评价了所有单体化合物对人肝癌HepG2细胞体外增殖抑制活性,同时利用分子对接技术考察了活性最好的化合物与肝癌靶标的结合情况。结果表明:(1)从该活性部位共分离得到14个化合物,包括12个新克罗烷型二萜类化合物和2个黄酮类化合物,分别鉴定为scutefolide C(1)、6-乙酰氧基-7-烟酸酰氧基半枝莲碱G(2)、scutestrigillosin D(3)、scutehenanine D(4)、半枝莲碱A(5)、半枝莲碱B(6)、7-烟酸酰氧基半枝莲碱H(7)、半枝莲碱N(8)、半枝莲碱Y(9)、barbatin A(10)、barbatin B(11)、barbatin D(12)、5,7,6′-三羟基-2′-甲氧基黄酮醇(13)和5,8-二羟基-6,7-二甲氧基黄酮(14)。其中,化合物1-3、13、14为首次从该植物中分离得到。(2)活性测试结果显示,化合物4、7、10-12表现出较弱的HepG2细胞增殖抑制活性,化合物6的细胞增殖抑制活性和阳性对照(顺铂)活性接近,而化合物5表现出比顺铂更强的细胞增殖抑制活性。(3)分子对接结果显示,化合物5和化合物6与肝癌靶蛋白VEGF-2均具有良好的结合力。该研究结果不仅丰富了半枝莲的化学物质类群,也为进一步深入研究活性化合物抗肝癌的作用机制提供了参考。

丽江山荆子链状化学成分研究

目的:了解丽江山荆子Malus rockii干燥枝叶的化学成分。方法:采用硅胶、MCI、Sephadex LH-20等柱色谱对丽江山荆子干燥枝叶95%乙醇提取物进行分离纯化,依据理化性质和现代波谱分析技术进行结构鉴定。结果:从丽江山荆子干燥枝叶95%乙醇提取物中分离得到7个单体化合物,分别鉴定为反式植醇(1)、植物烯醛(2)、棕榈酸植酯(3)、1-十六烷酸甘油单酯(4)、9,12,13-三羟基-(10E,15Z)-十八碳二烯酸甲酯(5)、α-亚麻酸(6)、十八醇(7)。结论:所有化合物均为首次从丽江山荆子植物中分离得到,其中化合物1~6为首次从苹果属植物中分离得到。

中药蔓荆子的化学成分及药理作用研究进展

蔓荆子是我国用药历史悠久的传统中药。主要含有萜类、黄酮类、木脂素类、酚酸类、甾类、蒽醌类等化学成分;具有广泛的生物活性,包括解热镇痛、抗菌、抗炎、抗氧化、抗肿瘤、降血糖等,常用于治疗风热、感冒头痛、偏头痛等症状。本文将从化学成分和药理作用方面,对蔓荆子近年来研究进展进行综合归纳整理,为蔓荆子进一步开发应用提供参考。

Diterpenoids from the Roots of Agastache rugosa

从土藿香根中得到两个二萜化合物，藿香酚（２）及异藿香酚（３）。经光谱解析（ＩＲ，ＵＶ，ＨＲＭＳ及ＮＭＲ谱），确定它们的结构分别为１１，１４ｄｉｈｙｄｒｏｘｙ１２ｍｅｔｈｏｘｙ１９（４→３）ａｂｅｏａｂｉｅｔａ４，（１８），８，１１，１３ｔｅｔｒａｅｎ７ｏｎｅ（２）和１１，１４ｄｉｈｙｄｒｏｘｙ１２ｍｅｔｈｏｘｙ１９（４→３）ａｂｅｏａｂｉｅｔａ３，８，１１，１３ｔｅｔｒａｅｎ７ｏｎｅ（３）藿香酚（２）为一新的化合物，而异藿香酚（３）系首次从天然界分离得到，二者为一对异构体。

西湖凹陷西部斜坡带原油来源

原油来源分析是确定油气勘探方向的重要依据。利用有机地球化学分析手段,分析了西湖凹陷西部斜坡带原油和烃源岩特征,通过生物标志物谱图和生物标志物参数的对比,结合原油与烃源岩分布特征,确定了西湖凹陷西斜坡不同区原油的来源。结果表明:(1)研究区原油总体上富含指示陆源高等植物输入的生物标志物,但平北地区原油碳同位素重,二萜类丰富,规则甾烷以C29甾烷为主;平湖地区原油碳同位素较轻,二萜类含量较高,且具有较低的伽马蜡烷;黄岩-天台地区原油碳同位素轻,二萜类含量低,规则甾烷以C29甾烷为主,同时C27甾烷的含量也较高。(2)研究区发育煤系烃源岩(包括煤和炭质泥岩)和暗色泥岩两类烃源岩。煤系烃源岩富含来源于裸子植物的异海松烷类和蕨类植物的16β(H)-扁枝烷,从平北到黄岩-天台地区的煤系烃源岩中16β(H)-扁枝烷含量增加;暗色泥岩二萜类含量低,16β(H)-扁枝烷相对于降异海松烷占优势,且从平北到黄岩-天台地区暗色泥岩中C27甾烷、16β(H)-扁枝烷增加。(3)平北地区原油主要为煤系烃源岩贡献,平湖地区原油为煤系烃源岩和暗色泥岩混合贡献,且煤系烃源岩的贡献较大,黄岩-天台地区原油主要为暗色泥岩贡献。研究成果对深化西湖凹陷油源认识及油气勘探部署有一定的指导作用。

Antioxidant,lipid peroxidation inhibition and free radical scavenging efficacy of a diterpenoid compound sugiol isolated from Metasequoia glyptostroboides

Objective:To investigate the antioxidant enicacy of a biologically active dilerpenoid compound sugiol isolated from Metasequoia glyptostroboides(M.glyptostroboides)in various antioxidant models.Methods:An abietane type diterpenoid sugiol,isolated from ethyl acetate extract of M.glyptostroboides cones,was analyzed for its antioxidant efficacy as reducing power ability and lipid peroxidation inhibition as well as its ability to scavenge free radicals such as 1,1-diphenyl-2-picryl hydrazyl,nitric oxide,superoxide and hydroxyl radicals.Results:The sugiol showed significant and concentration-dependent antioxidant and free radical scavenging activities.Consequently,the sugiol exerted lipid peroxidation inhibitory effect by 76.3%as compared to a-tocopherol(80.13%)and butylaled hydroxyanisole(76.59%).In addition,the sugiol had significant scavenging activities of l,l-diphenyl-2-picryl hydrazyl,nitric oxide,superoxide and hydroxyl free radicals in a concentration-dependent manner by 78.83%,72.42%,72.99%and 85.04%,when compared to the standard compound ascorbic acid(81.69%,74.62%,73.00%and 73.79%)and a-tocopherol/butylated hydroxyanisole(84.09%,78.61%,74.45%and 70.02%),respectively.Conclusions:These findings justify the biological and traditional uses of M.glyptostroboides or its secondary metabolites as confirmed by its promising antioxidant efficacy.

Effects of radix curcumae-derived diterpenoid C on Helicobacter pylori-induced inflammation and nuclear factor kappa B signal pathways

AIM:To study effect of diterpenoid C extracted from radix curcumae on Helicobacter pylori(H.pylori)-infected inflammation,intestinal metaplasia,and nuclear factor kappa B(NF-κB)signaling pathway in vitro.METHODS:We used I-type H.pylori to infect human gastric epithelial gastric epithelium cell line(GES-1)cell lines,and then H.pylori-infected GES-1 cells were treated with radix curcumae(RC)-derived diterpenoid C of different concentrations(5,10,20μg/mL)and amoxicillin.The expression of p65,IκB kinase(IKK)αand IKKγproteins was detected with Western blotting,and the expression of interleukin(IL)-8,IL-6 and IL-4 was determined with enzyme-linked immunosorbent assay method.Data were analyzed using SPSS software ver18.0.For comparisons between groups of more than two unpaired values,one-way analysis of variance(ANOVA)was used.If an ANOVA F value was significant,post hoc comparisons were performed between groups.If results were not normally distributed,the Mann-Whitney U test was used to compare two groups of unpaired values,whereas for comparisons between groups of more than two unpaired values,the Kruskal-Wallis H test was used.Statistical significance was established at P<0.05.RESULTS:The MTT assay results revealed the inhibited rate of GES-1,and indicated that the IC5 of RCderived diterpenoid C and amoxicillin all were 5μg/mL for gastric GES-1 cells.The expression of IL-8 was significantly increased,especially at 12 h time point;and the expression of IL-4 was decreased in H.pyloriinfected GES-1 cells.After H.pylori-infected GES-1 cells were treated with RC-derived diterpenoid C of different concentrations and amoxicillin,the expression of IL-8was decreased at 12,24,48,72 h points(P<0.01),especially in high-concentration diterpenoid C(20μg/mL)group;and the expression of IL-4 was increased,especially in moderate and high-concentration diterpenoid C(10 and 20μg/mL)groups.RC-derived diterpenoid C had the inhibitory effects on H.pylori-induced p65 translocation from cytoplasm into cell nucleus,H.pylori-stimulant IkBαdegradation,the phosphorylation of p65 and IkBα,and the expression of IKKαand IKKβproteins.CONCLUSION:RC-derived diterpenoid C can block NF-κB signal pathway,effectively reducing the secretion of H.pylori-induced proinflammatory cytokine and increasing the secretion of anti-inflammatory cytokine.

New diterpenoid glucosides from Siegesbeckia pubescens

Five new diterpenoids isolated from Siegesbeckia pubescens, pubesides A similar toE, were established as ent-2 alpha ,15,16-trihydroxypimar-8(14)-en-2-O-beta -D-glucopyranoside (1), ent-15,16,19-trihydroxypimar-8(14)-en-19-O-beta -D-glucopyranoside (2), beta -D-glucopyranosyl-ent-15,16-dihydroxypimar-8(14)-en-19-oiclate (3), ent-2-oxo-15,16,19-trihydroxypimar-8(14)-en-19-O-beta -D-gluco-pyranoside (4), ent-2-oxo-15,16,19-trihydroxypimar-8(14)-en-19-O-beta -D-glucopyranoside-15,16-acetonide (5) by 1D and 2D NMR techniques.

New Diterpenoids from Coleus forskohlii

Two new diterpenoids, forskolin G and H were isolated from the chloroform extract of the roots of Coleus forskohlii, and based on spectroscopic data, their structures were identified as 1a-hydroxy-6b,7b-diacetoxy-8,13-epoxylabd-14-ene-11-one (1), and 1a,6b-diacetoxy-8,13-epoxy labd-14-ene-11-one (2), respectively.

The Diterpenoid Quinones from Coleus forskohlii

Two new diterpenoid quinones, colean S and T were isolated from the chloroform extract of the leaves of Coleus forskohlii, and based on spectroscopic data, their structures were identified as 1,4-phananthrenedione-4b,5,6,8a,9,10-hexahydro-3,9 beta ,10 alpha- tri-hydroxy-4b,7,8-trimethyl-2-propylene(2), respectively.

A new cassane diterpenoid lactone from the seed of Caesalpinia minax

A new cassane diterpenoid lactone was isolated from the seed of Caesalpinia minax. On the basis of spectral evidences, its structure was established as 12α-methoxyl, 5α, 14β-dihydroxy-1α, 6α, 7β-triacetoxycass-13（15）-en-16, 12-olide.