Six new dimeric 2-(2-phenylethyl)chromones ( 1 - 6 ) were successfully isolated from the ethanol extract of agarwood of Aquilaria filaria from Philippines under HPLC-MS guidance. Compounds 1 - 6 are all dimers formed by linking 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone and flindersia 2-(2-phenylethyl)chromone via a single ether bond, and the linkage site (C5-O-C8 '' ) of compound 2 is extremely rare. A variety of spectroscopic methods were used to ascertain their structures, including extensive 1D and 2D NMR spectroscopic analysis, HRESIMS, and comparison with literature. The in vitro tyrosinase inhibitory and anti-inflammatory activities of each isolate were assessed. Among these compounds, compound 2 had a tyrosinase inhibition effect with an IC 50 value of 27.71 +/- 2.60 mu M, and compound 4 exhibited moderate inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells with an IC 50 value of 35.40 +/- 1.04 mu M.
Two unprecedented 2-(2-phenethyl)chromone dimers, aquicrassones A and B (1 and 2), were isolated by HPLCMS guided method from the ethanol extract of red soil agarwood originating from Aquilaria crassna in Vietnam. Their structures were unambiguously elucidated by analysis of HR-ESI-MS, 1D and 2D NMR, CD data and by comparison with literature data. Compounds 1 and 2 were evaluated for their inhibition effect on nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells. Compound 2 displayed anti-inflammatory activity with an IC50 value of 20.36 +/- 0.41 mu M.
Two unprecedented 2-(2-phenylethyl)chromone derivatives, (R)-2-[2-hydroxy-2-(3-hydroxy-4-methoxyphenyl) ethyl]chromone (1) and (R)-1-hydroxy-5-(4-hydroxyphenyl)-1-phenylpentane-3-one (2), with one known compound were isolated from cultivated "Qi-Nan" agarwood of Aquilaria sinensis. Their structures were elucidated by analysis of 1D and 2D NMR as well as HRESIMS. TDDFT-ECD calculation was used to determine the absolute configuration. At 50 mu M, compounds 1 and 3 exhibited significant neuroprotective effect, enhancing the cell vitality of human neuroblastoma SH-SY5Y cells induced by H2O2 to 73.24 +/- 0.43% and 74.71 +/- 5.24%, respectively.
目的 研究栽培奇楠沉香Aquilariae Lignum Resinatum的化学成分及其抗炎活性.方法 采用硅胶、Sephadex LH-20凝胶等多种柱色谱分离技术分离化合物,并通过质谱、核磁共振等现代波谱学方法鉴定其结构,采用Griess法测试化合物的抗炎活性.结果 从栽培奇楠沉香的乙醇提取物中分离得到17个化合物,分别为2-[(4-甲氧基苯甲酰氧基)甲基]色酮(1)、2-(2-苯乙基)色酮(2)、2-[2-(3-羟基-4-甲氧基苯)乙基]色酮(3)、2-[2-(3-甲氧基-4-羟基苯)乙基]色酮(4)、2-[2-(4-甲氧基苯)乙基]色酮(5)、2-[2-(2-羟基苯)乙基]色酮(6)、2-[2-(4-羟基苯)乙基]色酮(7)、6-羟基-2-[2-(3-羟基-4-甲氧基苯)乙基]色酮(8)、6-甲氧基-2-[2-(4-甲氧基苯)乙基)]色酮(9)、(R)-2-[2-羟基-2-(4-羟基苯)乙基]色酮(10)、(S)-2-[2-羟基-2-(4-羟基苯)乙基]色酮(11)、4-羟基苯甲酸甲酯(12)、4-丙烯基苯甲醚(13)、7β-H-9(10)-烯-11,12-环氧-8-氧艾里莫芬烷(14)、(5S,7S,9S,10S)-(-)-9-羟基-芹子烷-3,11-二烯-14-醛(15)、β-榄香烯-9β-醇(16)、角鲨烯(17).结论 化合物1为新化合物,化合物16首次在沉香中发现.体外抗炎活性测试结果表明,化合物8具有抑制脂多糖诱导小鼠单核巨噬细胞RAW264.7产生 NO 的活性,半数抑制浓度(median inhibition concentration,IC50)值为(27.81±2.34)μmol/L.
Agarwood 'Qi-Nan' is commonly regarded as the highest quality agarwood, and has been highly valued for its fragrance. With the increasing amount of cultivated agarwood 'Qi-Nan' in recent years, evaluation of the aroma compounds was drawn attention. Therefore, the volatile compounds in three cultivated 'Qi-Nan' agarwood samples were extracted by simultaneous distillation-extraction (SDE) and analysed by GC-O-MS, combined with aroma extract dilution analysis (AEDA). A total of 70 volatile compounds were identified from three samples, in which sesquiterpenes and aromatics were characterized as key aroma-active components. Nine compounds were considered as common aroma-active volatiles in these three essential oils according to their flavour dilution (FD) activity and relative flavour activity (RFA) value, and among them, dihydro-beta-agarofuran and 4-methoxy-benzaldehyde were the most important aroma-active compounds. Additionally, three 'Qi-Nan' agarwood samples showed different aroma specificity. TD agarwood was characterized by sweet sandalwood odour due to the dominant aroma-active compound of beta-Santalol. WS agarwood was distinguished by its woody odour because alpha-kessyl acetate was its primary aroma. HQ agarwood was featured by woody, spicy and balsamic odour on account of its main aroma compounds of agarospirol and beta-elemene.
Purpose:Our previous study in 2009 concluded that glutamine may shorten the length of hospital stay(LOS)in patients with severe burns.Recent large-scale studies have suggested a decline in the effec-tiveness of glutamine in treating patients with severe burns over the last decade.Therefore,we con-ducted this systematic review and meta-analysis to update the status of glutamine uses in patients with severe burns. Methods:We retrieved related literature prior to December 2022 from the PubMed,Web of Science,Cochrane Library,Embase,SinoMed,Wanfang,and CNKI databases.Terms such as glutamine,enteral and burn were linked for searching.Adults patients with severe burns were included and non-randomized controlled trials were excluded.Data from studies that compared enteral glutamine for severe burns with a control group were extracted.The primary outcomes of mortality and infectious morbidities were pooled and analyzed.The modified Jadad scale and Cochrane collaboration's tool were used to assess the risk of bias in RCTs,and the Review Manager 5.4 was used to pool and analyze the data. Results:Six randomized controlled trials involving 1398 patients were included in the analysis.There were no significant differences in overall mortality(risk ratio(RR)=0.37;95%confidence interval(CI):0.06-2.37;p=0.300)or infectious morbidities(RR=0.73;95%CI:0.41-1.31;p=0.290).The incidence of multiple organ dysfunction syndrome was similar between the 2 groups(RR=0.27;95%CI:0.03-2.24;p=0.220).The LOS(mean difference(MD)=-8.97;95%CI:-15.22 to-2.71;p=0.005)and LOS/total burn surface area(MD=-0.27;95%CI:-0.54 to 0.00;p=0.050)decreased in the enteral glutamine group.The incidence of wound infection was significantly reduced(RR=0.42;95%CI:0.16-1.06;p=0.070). Conclusion:Compared to the control group,enteral glutamine administration may not improve the mortality,although it may be associated with a shorter LOS,a lower LOS/total burn surface area ratio,and may reduce the risk of wound infection in patients with severe burns.
Most of the breast cancers are estrogen receptor-positive recurring with a steady rate of up to 20 years dysregulating the normal cell cycle. Dinaciclib is still in clinical trials and considered as a research drug against such cancers targeting CDK2. The major goal of this study was to identify the potential inhibitors of CDK-2 present in Moringa oleifera for treating hormonal receptor positive breast cancers. For this purpose, in silico techniques; molecular docking, MM-GBSA and molecular dynamics simulations were employed to screen Moringa oleifera compounds and their anticancer potential was determined against CDK-2 protein targets. Among 36 compounds of Moringa oleifera reported in literature, chlorogenic acid (1), quercetin (2), ellagic acid (3), niazirin (4), and kaempferol (5) showed good affinity with the target. The interaction of the compounds was visualized using PYMOL software. The profiles of absorption, distribution, metabolism, excretion (ADME) and toxicity were determined using SWISS and ProTox II webservers. The MTT assay was performed in-vitro using MCF-7 cancer cell lines to validate the anticancer potential of Moringa oleifera leaf extract. MTT assay results revealed no significant change in proliferation of Mcf-7 cells following 24 h treatment with fraction A (petroleum ether). However, significant antiproliferative effect was observed at 200 µg/mL dose of fraction B (ethyl acetate) and cell viability was reduced to 40%. In conclusion, the data suggested that all the compounds with highest negative docking score than the reference could be the potential candidates for cyclin dependent kinase-2 (CDK-2) inhibition while ellagic acid, chlorogenic acid and quercetin being the most stable and potent inhibitors to treat estrogen receptor positive breast cancer targeting CDK-2. Moreover, the data suggested that further investigation is required to determine the optimum dose for significant antiproliferative effects using in-vivo models to validate our findings of in-silico analysis.
Nine new sesquiterpenoids (1–9) were isolated from ethyl ether extract of agarwood originated from Aquilaria sp., including three novel sesquiterpenoids (1–3) derived from zizaane, together with six zizaane-type sesquiterpenoids (4–9). All structures were unambiguously elucidated based on 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of sesquiterpenoids was determined by comparison of the experimental and computed ECD spectra. In vitro anti-inflammatory assessment showed that compound 9 exhibited inhibition of NO production in LPS-stimulated RAW264.7 cells with an IC50 value of 62.22 ± 1.27 μM.
Three phenolic compounds (±1 and 2) including a pair of new enantiomers were isolated from the sclerotia of Inonotus obliquus. Their structures were assigned by extensive spectroscopic analyses. All the compounds were evaluated for the neuroprotective activity against oxidative damage on human neuroblastoma SH-SY5Y cells induced by H2O2. Compound 2 showed remarkable neuroprotective effect and significantly improved the cell viability of SH-SY5Y cells treated by H2O2.
Four new dimeric 2-(2-phenylethyl)chromones (1–4) were isolated from the agarwood of Aquilaria crassna in Laos. All structures were determined based on extensive spectroscopic methods including IR, UV, 1D and 2D NMR, ECD, and HRMS. The structures of compounds 1–3 were characterized by two C-O-C linkages between the two chromone moieties, while compound 4 featured one C-O-C linkage and one CC bond connecting with two chromone moieties. Compounds 1 and 3 showed weak cytotoxicity against human hepatocellular carcinoma BEL-7402 cell line with IC50 values of 44.68 and 42.10 μΜ.
为分析海南不同产地辣木叶的成分差异,选取海南万泉、博鳌、文昌、澄迈和东方产辣木叶进行总黄酮和挥发性成分分析.结果表明,以澄迈和万泉产地辣木叶的总黄酮含量最高,分别达到4.14%和4.04%,文昌产地辣木叶含量最低(2.12%).通过GC-MS分析,从海南辣木叶中共鉴定了59个成分,主要包括酚类、酸类、糖苷类、烷烃类、酯类和醇类及其他类成分,其主要共有成分为2,2'-亚甲基双-(4-甲基-6-叔丁基苯酚)、棕桐酸、地芰普内酯和丙三醇.同时也发现不同产地辣木叶的成分存在差异,其中,万泉产的辣木叶中的糖苷类、酯类和醇类成分含量比较丰富,其特异性成分主要为乙酸异丙酯和二氢猕猴桃内酯;博鳌产的辣木叶中的糖苷类和酚类含量比较丰富,其特异性成分主要为2,6,10,14-四甲基-十六烷;文昌产的辣木叶中的烷烃类和醇类和酸类成分含量比较丰富,其特异性成分主要为2-己基-1-十二烷醇、2-己基-1-癸醇和二十八烷醇;澄迈产的辣木叶中的烷烃类和酚类成分含量比较丰富,其特异成分主要为二十二烷和二十七烷;东方产的辣木叶中的糖苷类含量比较丰富,其特异性成分为2-甲氧基-1,3-二氧戊环和3-乙基-4-甲基-吡咯-2,5-二酮.而且,文昌和澄迈产的辣木叶没有检测到4-(α-L-鼠李糖氧基)苯基乙腈,东方产地的辣木叶没检测到烷烃类成分.研究结果初步表明,海南5个不同产地辣木叶中化学成分存在相似性和差异性,为不同产地辣木叶的质量评价提供参考.
综合运用多种柱色谱技术从越南红土沉香乙醇提取物中分离得到13个化合物,经过现代波谱学技术鉴定其结构为:7-甲氧基-2-[2-(4-甲氧基苯基)乙基]色酮(1),6-甲氧基-2-(2-苯乙基)色酮(2),6,7-二甲氧基-2-(2-苯乙基)色酮(3),6-甲氧基-2-[2-(4-甲氧基苯基)乙基]色酮(4),6-甲氧基-2-[2-(3-甲氧基苯基)乙基」色酮(5),5-羟基-6-甲氧基-2-[2-(4-甲氧基苯基)乙基]色酮(6),6,8-二羟基-2-(2-苯乙基)色酮(7),(1β,3α,4αβ,5β,8aα)-4a,5-dimethyl-3-(prop-l-en-2-yl)octahydronaphthalene-1,8a(1H)-diol(8),rel-(4S,5R,7R,8R,11R)-eremophil-9-en-12,8-olide(9),cyclodebneyol(10),柯拉斯那酸甲酯(11),白木香醇(12)和4-表-15-羟基菖蒲螺烯酮(13).其中,化合物1为新天然产物,所有化合物均为首次从红土沉香中分离得到.以上化合物的抗炎活性测试结果表明,化合物3、8和13具有一定的抗炎活性,IC50值分别为81.23±2.83、39.55±3.75和72.63±2.87 μmol·L-1.
为进一步研究国产人工打洞法所结沉香中的化学成分,本研究采用硅胶柱色谱、Sephadex LH-20、半制备高效液相等色谱方法从其乙酸乙酯萃取物中分离纯化得到2个单体化合物.根据核磁共振(NMR)、质谱(MS)等波谱数据分别鉴定为2-(2-苯乙基)色酮二聚体(+)-3′,3′′′-dihydroxy-4′,4′′′-dimethoxyaquisinenone G(1)和aquilasinenone F(2),其中化合物1为新化合物.抗氧化活性测试结果表明,化合物1和2都对DPPH自由基具有一定的清除能力,其中化合物2的IC50值为(64.6±1.6)mol/L,阳性对照为L(+)-抗坏血酸.
Two new 2-(2-phenethyl)chromone derivatives were isolated from agarwood of Aquilaria walla, including a dimeric 2-(2-phenethyl)chromone (1) and a flavonoid-2-(2-phenethyl)chromone (2). Their structures were established based on spectroscopic methods including HRESIMS, 1D, and 2D NMR. Compounds 1 and 2 showed cytotoxic activity against five human cancer cell lines with IC50 values ranging from 4.96?44.34 ?M.
采用水蒸气蒸馏法提取奇楠沉香精油,其得率为0.30%.通过气相色谱-质谱联用方法分析测定奇楠沉香精油中的化学成分,并通过峰面积归一法确定各化学成分的相对含量.同时对13种香气特征成分进行了描述,主要为倍半萜类化合物.本研究从奇楠沉香精油中分离鉴定出35个化合物,占精油总相对含量的92.19%,主要由倍半萜类(31个)、2-(2-苯乙基)色酮类(1个)以及芳香性化合物(3个)组成,其中倍半萜类化合物含量最高,达到总相对含量的90.28%.奇楠沉香精油中含有的倍半萜类成分主要有艾里莫芬烷型、愈创木烷型、桉烷型、沉香螺旋烷型、沉香呋喃型和杜松烷型6种类型,相对含量分别为41.84%、18.42%、12.30%、1.97%、1.88%和0.50%.
Organic material (OM) applied to cropland not only enhances soil fertility but also profoundly affects soil nitrogen cycling. However, little is known about the relative contributions of soil ammonia-oxidizing archaea (AOA) and bacteria (AOB) to nitrous oxide (N2O) production during ammonia oxidation in response to the additions of diverse types of OMs in the tropical soil for vegetable production. Herein, the soils were sampled from a tropical vegetable field subjected to 4-year consecutive amendments of straw or manure. All the soils were amended with ammonium sulfate ((NH4)2SO4, applied at a dose of 150 mg N kg−1) and incubated aerobically for four weeks under 50% water holding capacity. 1-octyne or acetylene inhibition technique was used to differentiate the relative contributions of AOA and AOB to N2O production. Results showed that AOA dominated N2O production in soil managements of unfertilized control (CK), chemical fertilization (NPK), and NPK with straw (NPKS), whereas AOB contributed more in soil under NPK with manure (NPKM). Straw addition stimulated AOA-dependent N2O production by 94.8% despite the decreased AOA-amoA abundance. Moreover, manure incorporation triggered both AOA- and AOB-dependent N2O production by 147.2% and 233.7%, respectively, accompanied with increased AOA and AOB abundances. Those stimulating effects were stronger for AOB, owing to its sensitivity to the alleviated soil acidification and decreased soil C/N ratio. Our findings highlight the stimulated N2O emissions during ammonia oxidation by historical OM amendments in tropical vegetable soil, with the magnitude of those priming effects dependent on the types of OM, and appropriate measures need to be taken to counter this challenge in tropical agriculture ecosystems.
对柬埔寨野生柯拉斯那(Aquilaria crassna)沉香的化学成分和生物活性进行研究.实验采用多种柱色谱法对该沉香进行分离纯化;通过现代波普技术结合化合物理化性质对所得单体化合物进行结构鉴定,从柬埔寨野生柯拉斯那沉香共分离出12个化合物,分别鉴定为7α-H-9 (10)-ene-11,12-epoxy-8-oxoeremophilane(1)、7β-H-9(10)-ene-11,12-epoxy-8-oxoeremophilane(2)、neopetasane(eremophila-9,11-dien-8-one)(3)、jinkoh-eremol(4)、(rel)-4β,5β,7β-eremophil-9-en-12,8β-olide(5)、诺卡酮(6)、11-hydroxy-valenc-1 (10)-en-2-one (7)、(7S,9S,10S)-(+)-9-hydroxy-selina-4,11-dien-14-al (8)、5-羟基-2-[2-(4-甲氧基苯)乙烯基]色酮(9)、5-羟基-6甲氧基-2-(2-苯乙基)色酮(10)、6-甲氧基-2-(2-苯乙基)色酮(11)、5-羟基-6甲氧基-2-[2-(4-甲氧基苯)乙基]色酮(12).其中化合物1~8为倍半萜类化合物,化合物9为2-(2-苯乙烯基)色酮类化合物,化合物10~12为2-(2-苯乙基)色酮类化合物.且化合物2~11均是首次从柯拉斯那沉香分离.采用Ellman比色法对单体化合物进行乙酰胆碱酯酶抑制活性的测定,活性测定结果表明化合物1~3和12具有乙酰胆碱酯酶抑制活性.
基于核磁共振氢谱-PCA-SVM回归方法,建立稀奶油中掺假植脂奶油的快速定量方法。核磁共振氢谱数据经分段积分、归一化等数据预处理后,利用PCA进行数据降维,采用交叉验证的方法对SVM中的参数进行优化,然后使用最优参数建立稀奶油中掺假植脂奶油比例的定量校准模型。将校正结果与PLS和SVM算法比较,并将所建立的3个模型用于测试集样本的预测。结果表明:基于PCA-SVM算法定量模型的RMSECV为3. 69,RMSEP为5. 87,训练集和测试集的R2分别为0. 987 5和0. 974 3,模型的稳定性、准确性以及模型的预测能力均优于PLS、SVM算法,且运行速度明显快于SVM算法。研究所建立的PCA-SVM模型表现出较好的模型稳定性和预测精度,结合核磁共振氢谱技术可以快速、准确地测定稀奶油中掺假植脂奶油含量,为规范市场上奶油蛋糕等烘焙制品的质量监管提供技术支持。
Five new sesquiterpenoids (1-5), together with a known compound 6 was isolated from ethyl ether extract of agarwood. Their structures were elucidated on the basis of spectroscopic techniques (UV, IR, MS, 1D and 2D NMR), as well as by comparison with literature data. Compound 5 exhibited inhibitory activity against acetylcholinesterase with inhibition ratio of 48.33 +/- 0.17% at the concentration of 50 mu g/mL.
Abstract Backgroud Aquilaria sinensis (Lour.) Spreng is one of the important plant resources involved in the production of agarwood in China. The agarwood resin collected from wounded Aquilaria trees has been used in Asia for aromatic or medicinal purposes from ancient times, although the mechanism underlying the formation of agarwood still remains poorly understood owing to a lack of accurate and high-quality genetic information. Findings We report the genomic architecture of A. sinensis by using an integrated strategy combining Nanopore, Illumina, and Hi-C sequencing. The final genome was ∼726.5 Mb in size, which reached a high level of continuity and a contig N50 of 1.1 Mb. We combined Hi-C data with the genome assembly to generate chromosome-level scaffolds. Eight super-scaffolds corresponding to the 8 chromosomes were assembled to a final size of 716.6 Mb, with a scaffold N50 of 88.78 Mb using 1,862 contigs. BUSCO evaluation reveals that the genome completeness reached 95.27%. The repeat sequences accounted for 59.13%, and 29,203 protein-coding genes were annotated in the genome. According to phylogenetic analysis using single-copy orthologous genes, we found that A. sinensis is closely related to Gossypium hirsutum and Theobroma cacao from the Malvales order, and A. sinensis diverged from their common ancestor ∼53.18–84.37 million years ago. Conclusions Here, we present the first chromosome-level genome assembly and gene annotation of A. sinensis. This study should contribute to valuable genetic resources for further research on the agarwood formation mechanism, genome-assisted improvement, and conservation biology of Aquilaria species.