New Quinoline Alkaloids from the Leaves and Stems of Orixa japonica,Orijanone, Isopteleflorine and 3'-O-Methylorixine

Orixa japonica (Rutaceae) is a shrub widely distributed in Japan, and has been found to contain various quinoline alkaloids.

We investigated the alkaloidal constituents of O. japonica, and four quinoline alkaloids were isolated and characterized. Three of these alkaloids are new natural products.     

A water drop-shaped slingshot in plants: geometry and mechanics in the explosive seed dispersal of Orixa japonica (Rutaceae)

Background and AimsIn angiosperms, many species disperse their seeds autonomously by rapid movement of the pericarp. The fruits of these species often have long rod- or long plate-shaped pericarps, which are suitable for ejecting seeds during fruit dehiscence by bending or coiling. However, here we show that fruit with a completely different shape can also rely on pericarp movement to disperse seeds explosively, as in Orixa japonica.MethodsFruit morphology was observed by hard tissue sectioning, scanning electron microscopy and micro-computed tomography, and the seed dispersal process was analysed using a high-speed camera. Comparisons were made of the geometric characteristics of pericarps before and after fruit dehiscence, and the mechanical process of pericarp movement was simulated with the aid of the finite element model.Key ResultsDuring fruit dehydration, the water drop-shaped endocarp of O. japonica with sandwich structure produced two-way bending deformation and cracking, and its width increased more than three-fold before opening. Meanwhile the same shaped exocarp with uniform structure could only produce small passive deformation under relatively large external forces. The endocarp forced the exocarp to open by hygroscopic movement before seed launching, and the exocarp provided the acceleration for seed launching through a reaction force.ConclusionsTwo layers of water drop-shaped pericarp in O. japonica form a structure similar to a slingshot, which launches the seed at high speed during fruit dehiscence. The results suggest that plants with explosive seed dispersal appear to have a wide variety of fruit morphology, and through a combination of different external shapes and internal structures, they are able to move rapidly using many sophisticated mechanisms.     

Five New Alkaloids from the Roots of Sophora flavescens

Five new quinolizidine alkaloids, including three sparteine‐type alkaloids ( 1  –  3 ) and two cytisine‐type alkaloids ( 4 and 5 ), along with four known ones, were isolated from the roots of Sophora flavescens. Their structures were determined by extensive spectroscopic techniques including IR, UV, NMR, and HR‐ESI‐MS. All the compounds were evaluated for their antibacterial activities against Staphylococcus aureus and Escherichia coli.     

阿朴菲类生物碱生物活性研究进展

综述了近年来阿朴菲类生物碱生物活性研究进展,包括肾上腺素受体作用活性、离子通道作用活性、抗血清素活性、细胞毒性、抗氧化活性、抗血小板聚集活性、神经系统活性、免疫调节活性、抗病毒活性以及其他活性等十个方面,并对其构效关系进行了初步分析。     

翅果油树叶片中总生物碱抗氧化活性研究

采用80%乙醇浸提翅果油树叶片中总生物碱,硅胶柱层析纯化,并用碘量法测定翅果油树叶片中总生物碱对猪油抗氧化性能的影响,用番红花红O-Mn2 -H2O2光度法测定其对羟基自由基的清除效果,用NBT光还原法测定其对超氧阴离子的清除效果.结果表明:翅果油树叶片总生物碱可有效延缓猪油的脂质过氧化反应,对猪油氧化的抑制效果显著高于同浓度的维生素C;其具有较强的清除羟基自由基和超氧阴离子的能力,EC50值分别为0.236g/L和0.101g/L,当浓度为1g/L时,其对羟基自由基和超氧阴离子的清除率可达96.04%和90.05%,显著高于同浓度的维生素C.     

Four New Diterpenoid Alkaloids from the Roots of Aconitum carmichaelii

Aconitum carmichaelii Debeaux is a widely used traditional Chinese medicine and an important source of clinical drugs, of which the parent and lateral roots are known as ‘Chuanwu’ and ‘Fuzi’, respectively. Four new C₁₉‐diterpenoid alkaloids, carmichasines A – D ( 1 – 4 ), were isolated from the roots of Aconitum carmichaelii, together with twelve known compounds ( 5 – 16 ). Their structures were elucidated via spectroscopic analyses, including HR‐ESI‐MS, IR, and NMR. Carmichasine A ( 1 ) is the first natural C₁₉‐diterpenoid alkaloid possessing a cyano group. Most of the diterpenoid alkaloids isolated were C₁₉‐category, which might provide further clues for understanding the chemotaxonomic significance of this plant. The cytotoxicity of the new compounds was also investigated against several human cancer cell lines, including MCF‐7, HCT116, A549, and 786‐0, and none of them showed considerable cytotoxic activity.     

Screening for Endophytic Fungi with Antitumour and Antifungal Activities from Chinese Medicinal Plants

Summary One hundred and thirty endophytic fungi isolated from 12 Chinese traditional medicinal plants collected at Yuanmou county and Dawei Mountain, Yunnan province, southwest China, were tested for antitumour and antifungal activities by MTT assay on human gastric tumour cell line BGC-823 and the growth inhibition test against 7 phytopathogenic fungi. The results showed that fermentation broths from 9.2% of the isolates exhibited antitumour activity and 30% exhibited antifungal activity, moreover, some of them exhibited broad-spectrum antifungal activity. The active isolates were identified to 32 taxa. The results indicate that the endophytic fungi of Chinese traditional medicinal plants are promising sources of novel bioactive compounds.     

Matrine-Type Alkaloids from the Seeds of Sophora alopecuroides and Their Potential Anti-inflammatory Activities

Three new matrine-type alkaloids, 8β-hydroxyoxysophoridine ( 1 ), 9β-hydroxysophoridine ( 2 ), 9β-hydroxyisosophocarpine ( 3 ), together with one known analog, 11,12-dehydromatrine ( 4 ), were isolated from the seeds of Sophora alopecuroides L. The structures of new compounds were elucidated using extensive spectroscopic techniques including the experimental and calculated ECD data. The anti-inflammatory activities of all the isolates on NO production in RAW 264.7 cells stimulated by lipopolysaccharide were evaluated. Among them, 8β-hydroxyoxysophoridine ( 1 ) showed a significant inhibitory effect with an IC₅₀ value of 18.26 μM.     

Aaptolines A and B,Two New Quinoline Alkaloids from the Marine Sponge Aaptos aaptos

Two new quinoline alkaloids, aaptolines A and B, were isolated from the marine sponge Aaptos aaptos. Their structures were determined by HR‐ESI‐MS data, NMR analysis, and X‐ray crystallography. Structurally, aaptoline A is characterized as having a quinoline skeleton fused with a 1,4‐dioxane motif at the C(7)?C(8) position, whereas aaptoline B possessed an intriguing 1H‐pyrrolo[2,3‐g]quinoline moiety. The cytotoxic assay of these compounds showed no cytotoxicity towards HepG2, A549, and PC9 cancer cell lines and had IC₅₀ values greater than 20 μm .     

杜仲内生真菌的抑菌活性筛选

以金黄色葡萄球菌、枯草芽孢杆菌、大肠杆菌为测试菌种。对杜仲(Eucommia ulmoides Oliv.)根、茎、叶中分离出的20株内生真菌及其次生代谢物进行抗菌活性筛选。结果表明：有15个菌株至少对1种实验细菌具有抑菌活性,19株的代谢产物至少对1种实验细菌具有抑菌活性,其中有3株内生真菌及其次生代谢产物对测试病原细菌均有较强抑制作用。     

迷迭香酸对几种植物病原真菌的抗菌活性*

研究了迷迭香酸对不同植物病原真菌菌丝生长和孢子萌发的抑制活性。试验结果表明,迷迭香酸对供试的8种植物病原真菌菌丝生长均有抑制作用,其中对番茄灰霉病菌、芒果灰斑病菌、柑桔青霉和梨黑斑病菌抑制作用较强,EC50分别为615．04μg/mL、698．23μg/mL、714．50μg/mL和809．10μg/mL;对杉木猝倒病菌和苹果树腐烂病菌抑制作用次之,EC50分别为1039．92μg／mL和1044．72μg/mL;对松枯梢病菌和种实霉烂病菌的抑制作用较弱,EC50分别为1256．90μg/mL和1270．87μg/mL。迷迭香酸对供试的6种植物病原真菌孢子萌发也有明显的抑制作用,EC50大致在400～700μg/mL范围,其中对梨黑斑病菌孢子萌发抑制作用最强,EC50为395．37μg/mL。     

海南粗榧内生真菌抗肿瘤抗菌活性的筛选

对72株海南粗榧(Cephalotaxus hainanensis Li)内生真菌进行了抗肿瘤和抗菌活性筛选。结果显示, 有9株内生真菌至少对一种指示瘤株具有细胞毒活性, 5株内生真菌对金黄色葡萄球菌有较强的抑菌活性, 1株内生真菌对辣椒疫霉有抑制作用。这表明海南粗榧内生真菌是寻找有价值的生物活性成分的潜在资源, 其生物活性成分值得进一步研究。     

青蒿内生真菌的抗肿瘤抗氧化活性

采用MTT法和DPPH法,分别测定已分离得到的68株贵州青蒿内生真菌乙酸乙酯粗提物的肿瘤细胞生长抑制率和DPPH自由基清除率。试验共筛选获得12株活性内生真菌,根据其形态特征进行鉴定,分别隶属于子囊菌亚门(Ascomycotina)的链格孢属(Alternaria)、刺盘孢属(Colletotrichum)、拟盘多毛孢属(Pestalotiopsis)和拟茎点霉属(Phomopsis);其中,有8株内生真菌至少对1种指示瘤株具有细胞毒活性,占总菌株数的11.8%;5株内生真菌具有不同程度的清除DPPH自由基活性,占总菌株数的7.4%;1株内生真菌同时具有细胞毒活性和抗氧化活性。     

木本曼陀罗内生真菌抗菌活性的筛选研究

从木本曼陀罗植物内生真菌中筛选高效抗菌活性的菌株。选择与人类和植物相关的36株病原微生物,分别对分离自木本曼陀罗(Datura arborea L.)植物的内生真菌77株进行了发酵代谢产物的抗菌活性筛选研究。结果显示:对细菌病原菌、皮肤致病真菌、植物致病真菌有抑制作用的内生真菌分别有24,9,17株,其中5株内生真菌对10种以上的供试病原菌有明显的抑制作用,活性最好的1株对20种病原菌有较强抑制活性,最大抑菌圈直径达48mm。这说明木本曼陀罗植物内生真菌抗菌能力较强,抗菌谱较广。     

Synthesis,Antimicrobial Activities,and Molecular Docking Studies of Dihydrotriazine Derivatives Bearing a Quinoline Moiety

In this article, three series of dihydrotriazine derivatives bearing a quinoline moiety ( 5a , 5b , 8a – 8c , and 9a – 9m ) have been designed, synthesized, and evaluated as antibacterial agents. Compounds 8a – 8c were found to be the most potent of all of the compounds tested with an MIC value of 1 μg/mL against several Gram‐positive (S. aureus 4220 and MRSA CCARM 3506) and Gram‐negative (E. coli 1924) strains of bacteria. In addition, 3‐[4‐amino‐6‐(phenethylamino)‐2,5‐dihydro‐1,3,5‐triazin‐2‐yl)‐6‐[(3‐chlorobenzyl)oxy]quinolin‐2‐ol ( 8a ) showed potent inhibitory activity (MIC=2 μg/mL) against Pseudomonas aeruginosa 2742, indicating that its antibacterial spectrum is similar to those of the positive controls gatifloxacin and moxifloxacin. Structure‐activity relationships (SAR) analyses and docking studies implicated the dihydrotriazine group in increasing the antimicrobial potency of the quinoline compounds. In vitro enzyme study implied that compound 8a also displayed DHFR inhibition.     

云南12种药用植物内生真菌分离及抗肿瘤活性菌株筛选

从马尾树、断肠草和白花蛇舌草等十二种云南药用植物中共分离到内生真菌263株,以卤虫模型对其中130株进行了抗肿瘤活性筛选,结果表明,有56.9%的菌株LD50≥4,39.2%的菌株LD50≥8,25.4%的菌株LD50≥16。以人胃癌细胞株BGC-823对LD50≥16的高活性菌株进行MTT法复筛,结果表明,有12株菌显示了细胞毒活性,抑制率从39.24%到100%不等。进一步研究表明,菌株D126和MT13对人白血病细胞株K562显示了较强的细胞毒活性,IC50分别为1∶438和1∶919。在12种植物中,小桐子的抗肿瘤活性菌株比率最高,为37.5%,其次为曼陀罗,为25.0%,而乌头、木瓜红、大花八角和重楼中未分离到抗肿瘤活性菌株。经鉴定,抗肿瘤活性菌株分属于12个分类单元     

26个川茶花品种亲缘关系的ISSR分析

采用ISSR分子标记,对重庆南山植物园中26个品种的川茶花古树进行了ISSR遗传多样性分析。选用14条扩增带型清晰且重复性好的引物共获得166条谱带,其中140条呈多态性,多态性比例(PPB)为84.34％。根据Nei-Li遗传相似性系数在0.708处,UPGMA结果将26个品种分为5个类群,在0.726处可进一步分为10个亚类群;26个川茶花品种的遗传相似性系数介于0.615和0.913之间,平均值为0.704,表明品种间亲缘关系较近。其中牡丹茶与花牡丹之间遗传相似性系数最大,为0.913,表明牡丹茶可能为花牡丹的芽变品种。川渝地区山茶古树资源丰富,但在古树的保护上也面临诸多问题,建议采取相应的措施加以保护。     

三种水生植物内生真菌多样性及其抗真菌活性

从华凤仙(Impatiens chinensis L.)、问荆(Equisetum arvense L.)和轮叶狐尾藻(Myriophyllum verticillatum L.) 3种植物中共分离到内生真菌155株。经鉴定, 它们分属于26个不同的分类单元。以杨桃炭疽菌(Colletotrichum gloeosporioides)、香蕉疫霉(Phytophthora nicotianae)和腐皮镰刀菌(Fusarium solani)等6种植物病原真菌为指示菌, 对3种水生植物内生真菌代谢产物进行抗菌活性研究。结果表明, 有37株内生真菌(占分离菌株总数的23.9%)显示出对一种或多种病原菌的抑菌活性。来自华凤仙、问荆和轮叶狐尾藻的抗菌活性菌株比例分别为29.2%、13.9%及37.1%, 都远低于已报道的陆生植物内生真菌中活性菌株的比例。抗菌活性菌株主要分布于枝孢属(Cladosporium)、木霉属(Trichoderma)和地霉属(Geotrichum)等5个属中。     

Antifungal Activities of Four Fatty Acids against Plant Pathogenic Fungi

The effect of the fatty acids linolenic acid, linoleic acid, erucic acid and oleic acid on the growth of the plant pathogenic fungi Rhizoctonia solani, Pythium ultimum, Pyrenophora avenae and Crinipellis perniciosa were examined in in vitro studies. Linolenic and linoleic acids exhibited activity against all of the fungi. However, whereas linolenic acid reduced mycelial growth of R. solani and C. perniciosa at 100 microM, the concentration had to be increased to 1000 microM before any effect on mycelial growth of P. ultimum and P. avenae was observed. Linoleic acid only reduced mycelial growth of R. solani, P. ultimum and P. avenae at 1000 microM, but led to a significant reduction in growth of C. perniciosa at 100 microM. In contrast, oleic acid had no significant effect on growth of R. solani or P. avenae, but gave significant reductions in mycelial growth of P. ultimum at 100 microM and reduced growth of C. perniciosa significantly at 1000 microM. All of the fatty acids reduced biomass production by all of the fungi significantly in liquid culture when added to the media at 100 microM. Erucic acid had no effect on fungal growth at any concentration examined. The antifungal activities exhibited by linolenic, linoleic and oleic acids may be useful in the search for alternative approaches to controlling important plant pathogens, such as those examined in this study.     

Microjaponin,A New Dihydroagarofuranoid Sesquiterpene from the Stem of Microtropis japonica with Antituberculosis Activity

A new dihydroagarofuran‐based sesquiterpene, microjaponin ( 1 ), was isolated from the stem of Microtropis japonica. Its structure was determined by in‐depth spectroscopic and mass‐spectrometric analyses. Microjaponin ( 1 ) exhibited potent in vitro antituberculosis activity, with an MIC value of 12.5 μg/ml against Mycobacterium tuberculosis H₃₇Rv.