The Clausena lansium genome provides new insights into alkaloid diversity and the evolution of the methyltransferase family

Wampee(Clausena lansium)is an important evergreen fruit tree native to southern China that has a long history of use for medicinal purposes.Here,a chromosome-level genome of C.lansium was constructed with a genome size of 282.9 Mb and scaffold N50 of 30.75 Mb.The assembled genome contains 48.70%repetitive elements and 24,381 protein-coding genes.Comparative genomic analysis showed that C.lansium diverged from Aurantioideae 15.91-24.95 million years ago.Additionally,some expansive and specific gene families related to methyltransferase activity and S-adenosylmethionine-dependent methyltransferase activity were also identified.Further analysis indicated that N-methyltransferase(NMT)is mainly involved in alkaloid biosynthesis and O-methyltransferase(OMT)participates in the regulation of coumarin accumulation in wampee.This suggested that wampee's richness in alkaloids and coumarins might be due to the gene expansions of NMT and OMT.The tandem repeat event was one of the major reasons for the NMT expansion.Hence,the reference genome of C.lansium will facilitate the identification of some useful medicinal compounds from wampee resources and reveal their biosynthetic pathways.

Coumarin and eugenol ameliorate LPS-induced inflammation in RAW 264.7 cells via modulating the NLRP3 inflammasome pathway

Objective:To investigate the underlying mechanism of anti-inflammatory action of coumarin and eugenol in lipopolysaccharide(LPS)-stimulated RAW 264.7 cells.Methods:RAW 264.7 cells were treated with 2.5μg/mL of LPS,50μM of coumarin,and 50μM eugenol for 24 h.The viability of the cells was assessed using MTT assay.The production of nitric oxide was determined using Griess reagent and DCFH-DA was used to measure the production of reactive oxygen species.The protein expression of NLRP3,IL-1β,NF-κB,and cyclooxygenase 2 was assessed using Western blot analysis.Results:Coumarin and eugenol showed anti-inflammatory effects against LPS-induced inflammatory response by ameliorating the expression of NLRP3 inflammasome and NF-κB,which further led to a subsequent reduction in IL-1β,nitric oxide,and reactive oxygen species.Conclusions:Coumarin and eugenol exert their anti-inflammatory activities by modulating the NLRP3 inflammasome pathway and NF-κB.These compounds may have promising therapeutic applications for the treatment of various inflammatory diseases.

禹白芷中香豆素成分的HPLC-MS/MS分析

The main constituents of the extract from Yubaizi (the roots of Angelica dahurica)were analyzed by HPLC-MS/MS method,and a total of six cumarins were unequivocally determined.The fragmentation patterns of the cumarins were found useful for their characterization,and the relative contents of the six compounds were also calculated.

Constituents of Chinese Drug Fangfeng, the Root of Saposhnikovia divaricata

从防风根的乙醇浸出物中分离鉴定出8个化合物。通过理化数据及光谱分析,分别鉴定为香柑内酯(Ⅰ),花椒毒内酯(Ⅱ),亥茅酚(Ⅲ),异紫花前胡内酯(Ⅳ),东茛菪内酯(Ⅴ),香草酸(Ⅵ),D-甘露醇(Ⅶ)和蔗糖(Ⅷ),其中Ⅳ与Ⅵ为首次自此植物中提得。

Two New Coumarins from the Roots of Aegle marmelos Xiu Wei Yang 1, Masao Hattori 2 and Tsuneo Namba 2

Two new coumarins, named marminal (13) and 7' O methylmarmin (15), along with nineteen known compounds: ( sitosteryl pentadecanoate (1), 4 methoxy 1 methyl 2 quinolone (2), aurapten (3), 4 sitosten 3 one (4), lupeol (5), imperatorin (6), xanthotoxin (7), dictamnine (8), (+) epoxyaurapten (9), ( sitosterol (10), ( fagarine (11), skimmianine (12), scoparone (14), umbelliferone (16), scopoletin (17), decursinol (18), marmesin (19), marmin (20), and integriquinolone (21) were isolated from the methanolic extract of the roots of Aegle marmelos Corr. (family Rutaceae).

Coumarin 6平面荧光太阳能聚光器的制备与性能分析

以PMMA作为基质材料,以Coumarin 6作为荧光物质,采用掺杂方式制备出平面荧光太阳能聚光器。制备得到的Coumarin 6平面荧光太阳能聚光器的几何尺寸分别为50 mm×50 mm×5 mm与100 mm×100 mm×5mm,将太阳能电池粘贴于聚光器的输出端,通过测试聚光器对太阳能电池输出功率的影响测定Coumarin 6平面荧光太阳能聚光器的聚光特性。而为了研究掺杂浓度对聚光器聚光特性的影响,制备了7种不同浓度的Coumarin 6平面荧光太阳能聚光器,并分别测试了其聚光特性,得出最优化的掺杂浓度。

Further Isolation of Coumarin from Angelica pubescence Maxim f. biserrata Shan et Yuan

Nine coumarin compounds were further isolated from Angelica pubescence. They were columbianedin (1), osthol (2), bergapten (3), isoimperaterin (4), meranzin hydrate (5), nodakenetin (6), marmesinin (7), columbianin (8) and angelidiol (9). Among them, 5～8 were isolated for the first time from this plant, 9 is a new natural product.

圆滑番荔枝树叶提取物的化学成分研究

目的对越南野生圆滑番荔枝(Annona glabra.L)叶的正己烷和氯仿提取部分的化学成分进行研究,找到新化合物。方法采用红外、质谱(GC-MS)、一维和二维核磁共振(1D,2D NMR)等方法进行结构分析。结果从越南野生圆滑番荔枝叶提取物中分离出四个化学成分,鉴定它们的结构分别为:β-sitosterol(1),β-sitosterol-3-O-β-D-glucopyranoside(2),6β-hydroxy-24-ethylcholest-4-en-3-one(3),and scopoletin(4)。结论其中化合物3和化合物4是圆滑番荔枝叶提取物的未知化学成分,在圆滑番荔枝植物番荔枝科中未见报道。

Quantitative and qualitative analysis of common peaks in chemical fingerprint of Yuanhu Zhitong tablet by HPLC-DAD–MS/MS

A quality control （QC） strategy for quantitative and qualitative analysis of “common peaks” in chemical fingerprint was proposed to analyze Yuanhu Zhitong tablet （YZT）, using high performance liquid chromatography with diode array detector and tandem mass spectrometry （HPLC-DAD-MS/MS）. The chromatographic separation was achieved on an Agilent Eclipse plus C18 column with a gradient elution using a mixture of 0.4‰ ammonium acetate aqueous （pH 6.0 adjusted with glacial acetic acid） and acetonitrile. In chemical fingerprint, 40 peaks were assigned as the “common peaks”. For quantification of “common peaks”, the detection wavelength was set at 254 nm, 270 nm, 280 nm and 345 nm, respectively. The method was validated and good results were obtained to simultaneously determine 10 analytes （protopine, jatrorrhizine, coptisine, palmatine, berberine, xanthotoxin, bergapten, tetrahydropalmatine, imperatorin and isoimperatorin）. For qualification of “common peaks”, 33 compounds including 10 quantitative analytes were identified or tentatively characterized using LC-MS/MS. These results demonstrated that the present approach may be a powerful and useful tool to tackle the complex quality issue of YZT.

Two New O-terpenoidal Coumarins, Excavacoumarin A and B from Clausena excavata

Two new O-terpenoidal coumarins named excavacoumarin A (2): B (3), and a known one 1 were isolated from the leaves of Clausena excavata Burm. f. (Rutaceae) collected in Xishuangbanna, Yunnan, Structure elucidation and unambiguous NMR assignments for the title compounds were carried out on the basis of 1D and 2D NMR experiments.

A Novel Dimeric Coumarin from Clausena lenis

A novel dimeric coumarin (1), a dimeric of seselin named diseselin A, was isolated from the aerial part of Clausena lenis. The structure was elucidated based on the MS, 1D and 2D NMR data.

Oxalic acid catalyzed solvent-free one pot synthesis of coumarins

Oxalic acid was found to be an efficient catalyst for Pechmann condensation, which includes the reaction between phenols and β-keto esters leading to formation of coumarin derivatives. The advantages of present methods are the use of cheap and easy available catalyst, solvent-free reaction conditions, better yields and shorter reaction time.

Three New Coumarins from Micromelum integerrimum

Three derivatives of micromelin, named hydramicromelins A-C (1-3), were isolated from the aerial part of Micromelum integerrimum (Buch.-Ham) Roem., respectively. Hydramicromelins A-C (1-3) were epimers which possessed the same plane structure and molecular formula. Their structures were elucidated based on MS and NMR data. The relative configurations of 1-3 were established by NOE analysis.

L-Proline as an efficient and reusable promoter for the synthesis of coumarins in ionic liquid

The effect of L-proline as a promoter on the condensation reaction of salicylaldehyde or its derivatives with ethyl acetoacetate in neutral ionic liquid [emim]BF4 was studied. All reactions were carried out under mild reaction conditions and achieved high yields. Moreover, the ionic liquid containing L-proline could be recycled and reused for several times without noticeably decreasing in productivity. The results show that the L-proline-[emim]BF4 system has a potential in contribution to the development of environmentally friendly and inexpensive processes in organic syntheses.

温和条件下丁二酰亚胺-N-磺酸催化合成双吲哚甲烷和香豆素衍生物(英文)

A mild and simple procedure is described for the synthesis of bis(indolyl)methane and coumarin derivatives using succinimide-N-sulfonic acid as an efficient,cheap,and reusable catalyst under mild conditions.

Anti-Alzheimer's disease potential of coumarins from Angelica decursiva and Artemisia capillaris and structure-activity analysis

Objective: To use structure-activity analysis to study the anti-Alzheimer's disease(anti-AD) activity of natural coumarins isolated from Angelica decursiva and Artemisia capillaries, along with one purchased coumarin(daphnetin). Methods: Umbelliferone, umbelliferone 6-carboxylic acid, scopoletin, isoscopoletin, 7-methoxy coumarin, scoparone, scopolin, and esculetin have been previously isolated; however 2'-isopropyl psoralene was isolated from Angelica decursiva for the first time to evaluate their inhibitory effects against acetylcholinesterase(ACh E), butyrylcholinesterase(BCh E), and β-site amyloid precursor protein cleaving enzyme 1(BACE1) enzyme activity. We scrutinized the potentials of coumarins as cholinesterase and BACE1 inhibitors via enzyme kinetics and molecular docking simulation. Results: Among the test compounds, umbelliferone 6-carboxylic acid, esculetin and daphnetin exhibited potent inhibitory activity against ACh E, BCh E and BACE1. Both esculetin and daphnetin have a catechol group and exhibit significant anti-AD activity against ACh E and BCh E. In contrast, presence of a sugar moiety and methoxylation markedly reduced the anti-AD activity of the coumarins investigated in this study. With respect to BACE1 inhibition, umbelliferone 6-carboxylic acid, esculetin and daphnetin contained carboxyl or catechol groups, which significantly contributed to their antiAD activities. To further investigate these results, we generated a 3D structure of BACE1 using Autodock 4.2 and simulated binding of umbelliferone 6-carboxylic acid, esculetin and daphnetin. Docking simulations showed that different residues of BACE1 interacted with hydroxyl and carboxylic groups, and the binding energies of umbelliferone 6-carboxylic acid, esculetin and daphnetin were negative(-4.58,-6.25 and-6.37 kcal/mol respectively). Conclusions: Taken together, our results suggest that umbelliferone 6-carboxylic acid, esculetin and daphnetin have anti-AD effects by inhibiting ACh E, BCh E and BACE1, which might be useful against AD.

Novel fluorescent chemosensor for Ag^+ based on coumarin fluorophore

A novel chemosensor 1 （CS1） bearing one coumarin and two carbodithioate groups was synthesized and its fluorescent sensing behavior toward metal ions was investigated. Ag^＋ addition to a CH3COCH3/H2O （3：7, v：v） solution of CS1 gave a significantly quenched fluorescence. Other ions including Pb^2＋, Zn^2＋, Cu^2＋, Ca^2＋, Cd^2＋, Co^2＋, Mg^2＋, Mn^2＋, Hg^2＋, Ag^＋, Ni^2＋ induced no or much smaller spectral changes. This constitutes an ON-OFF Ag^＋-selective fluorescent chemosensor.

Synthesis and Crystal Structure of 2-Amino- 3-ethoxycarbonyl-4-(4-chlorophenyl)-4H, 5H-pyrano-[3,2-c]-benzopyran-5-one

The title compound 2-amino-3-ethoxycarbonyl-4-(4-chlorophenyl)-4H,5H-pyrano- [3,2-c]-benzopyran-5-one (C21H16ClNO5, Mr = 397.80) has been synthesized and characterized by X-ray crystallography. It crystallizes in triclinic, space group P1 with a = 5.756(1), b = 10.099(1), c = 17.106(3) ? a = 80.49(1), b = 83.13(1), g = 80.07(1), V = 961.8(2) ?, Dc = 1.374 g/cm3, = 0.231 mm-1, Z = 2, F(000) = 412, the final R = 0.0369 and wR = 0.0947. In the molecule the pyran ring is of boat conformation. The intermolecular hydrogen bonds of NH…O(5)(x+2, y+1, z+1) and NH…Cl (x+1, y1, z) as well as intramolecular hydrogen bond NH…O(5) are found.

A new angelol-type coumarin glucoside from Angelica pubescens

A new angelol-type coumarin glucoside, 6-[（1R,2R）-1, 2-dihydroxy-3-β-D-glucosyloxy-3-methylbutyl]-7-methoxycoumarin, was isolated from the roots of Angelica pubescens. Its structure was elucidated on the basis of spectral analysis.

Defense responses of arbuscular mycorrhizal fungus-colonized poplar seedlings against gypsy moth larvae:a multiomics study

Arbuscular mycorrhizal(AM)fungi may help protect plants against herbivores;however,their use for the pest control of woody plants requires further study.Here,we investigated the effect of Glomus mosseae colonization on the interactions between gypsy moth larvae and Populus alba×P.berolinensis seedlings and deciphered the regulatory mechanisms underlying the mycorrhizal-induced resistance in the leaves of mycorrhizal poplar using RNA-seq and nontargeted metabolomics.The resistance assay showed that AM fungus inoculation protected poplar seedlings against gypsy moth larvae,as evidenced by the decreased larval growth and reduced larval survival.A transcriptome analysis revealed that differentially expressed genes(DEGs)were involved in jasmonic acid biosynthesis(lipoxygenase,hydroperoxide dehydratase,and allene oxide cyclase)and signal transduction(jasmonate-ZIM domain and transcription factor MYC2)and identified the genes that were upregulated in mycorrhizal seedlings.Except for chalcone synthase and anthocyanidin synthase,which were downregulated in mycorrhizal seedlings,all DEGs related to flavonoid biosynthesis were upregulated,including 4-coumarate-CoA ligase,chalcone isomerase,flavanone 3-hydroxylase,flavonol synthase,and leucoanthocyanidin reductase.The metabolome analysis showed that several metabolites with insecticidal properties,including coumarin,stachydrine,artocarpin,norizalpinin,abietic acid,6-formylumbelliferone,and vanillic acid,were significantly accumulated in the mycorrhizal seedlings.These findings suggest the potential of mycorrhiza-induced resistance for use in pest management of woody plants and demonstrate that the priming of JA-dependent responses in poplar seedlings contributes to mycorrhiza-induced resistance to insect pests.