Synthesis of anacardic acids, 6-[8(Z),11(Z)-pentadecadienyl]salicylic acid and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid

11-Chloro-3-methoxy-2-undecenal was synthesized from 8-bromooctanol, and an annelation reaction with this aldehyde and ethyl acetoacetate proceeded to give the ethyl 6-(8-chlorooctyl)salicylate. Ethyl 6-(8-chlorooctyl)salicylate was converted to ethyl 6-(7-formylheptyl)-2-methoxybenzoate through the iodide after protection of the phenolic hydroxyl group. Finally, the Wittig reaction with the aldehyde and triphenylphosphonium iodides in the presence of BuLi gave the methoxybenzoates, and then treatments of these methoxybenzoates with BBr3 in CH2Cl2 and 10% NaOH in ethanol gave 6-18(Z),11(Z)-pentadecadienyllsalicylic acid (anacardic acid 3) and 6-[8(Z),11(Z),14-pentadecatrienyl]salicylic acid (anacardic acid 4) which were isolated from plants of the anacardiaceae.     

Lignans and Triterpenes from the Root of Pseuderanthemum carruthersii var. atropurpureum

Two new lignans, pseuderesinol (1), pseuderanoside (2) and a new triterpene, pseuderanic acid (3) were isolated from the dried root of Pseuderanthemum carruthersii (SEEM.) GUILL. var. atropurpureum (BULL.) FOSB. (Acanthaceae), together with ten known compounds, including five lignans, (+)-eudesmin (4), (+)-magnolin (5), (+)-syringaresinol (6), (+)-episyringaresinol (7), (+)-1-hydroxysyringaresinol (8) and five triterpenes, squalene (9), oleanolic acid (10), lupeol (11), betulin (12), betulinic acid (13). Their chemical structures were elucidated by 1D- and 2D-NMR, computational quantum chemistry, as well as high resolution-electrospray ionization (HR-ESI)-MS spectroscopic analysis. The acetylcholinesterase inhibition and cytotoxic activities against HeLa and MCF-7 cancer cell lines were evaluated on some purified compounds at the concentration of 100?μg/mL. Pseuderesinol (1) and magnolin (5) exhibited moderate cytotoxic activities against the MCF-7 cancer cell line.     

Cytotoxic phenylpropanoids and a new triterpene, turformosinic acid, from Turpinia formosana Nakai

One new phenylpropanoid, turformosin A (1), and one new triterpene, turformosinic acid (2), together with 16 known compounds, were isolated from the stems of Turpinia formosana Nakai. All structures were elucidated on the basis of spectroscopic analysis, including 1D- and 2D-NMR techniques and MS analysis. Selected isolated compounds were evaluated for in vitro cytotoxicity against four human cancer cell lines and antioxidant scavenging effects on DPPH. (-)-(7'S,8'S)-threo-carolignan X (3) exhibited cytotoxicity against Hep2, WiDr, Daoy, and MCF-7 cell lines with ED(50) values of 3.60, 4.45, 6.07, and 13.7 μg/mL, respectively. Turformosin A (1), (-)-(7'S,8'S)- threo-carolignan X (3), methoxyhydroquinone-4-β-D-glucopyranoside (5), and methoxy-hydroquinone-1-β-D-glucopyranoside (6), exhibited similar anti-oxidative activity. Hep2 cells treated with 10 μg/mL of 3 showed elevation of sub-G1 population (from 20% at 8 h to 60% at 48 h), and activation of caspase-9/caspase-3/PARP cascade. Compound 3 induced intrinsic apoptotic pathway in Hep2 cells with dose and time dependence (10 μg/mL for 8 h).     

A new lignan from Oxytropis myriophylla

The 70% alcohol extract of Oxytropis myriophylla (PALL.) DC. (Leguminosae) exhibited high radical scavenging activity (IC(50) value: 88.0?μg?mL(-1) and 86.7?μg?mL(-1)) on 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radical scavenging assays. Further chemical investigation led the isolation of one new lignan, namely myriophylloside G (1), together with three known compounds. Their structural elucidations of all the compounds were based on extensive spectroscopic methods, including HRESIMS and 2D NMR experiments (HSQC, HMBC and (1)H-(1)HCOSY) and by comparison with reference values.     

Cytotoxic compounds from the leaves of Gaillardia aristata Pursh. growing in Egypt

Ten compounds, neopulchellin (1), 6α- hydroxyneopulchellin (2), β-sitosterol-3-O-β-D-glucoside (3), apigenin (4), quercitin (5), eupafolin (6), kaempferol-3-methoxy-7-O-α-L-rhamnoside (7), apigenin-7-O-β-D-glucopyranoside (8), α-amyrin (9) and β-sitosterol (10), were isolated from the leaves of Gaillardia aristata by applying bioassay guided fractionation. The cytotoxicity was traced against two human cancer cell lines (breast (MCF7) and colon (HCT116)). The highest cytotoxicity was revealed by compounds 1 and 2 (isolated from chloroform extract); with IC(50) values of 0.43, 0.32?μg?mL(-1) against MCF7 and 0.46, 0.34?μg?mL(-1) against HCT116, respectively. Compounds 9 and 10 (isolated from the n-hexane extract) exhibited lower IC(50) values of 3.05, 2.35?μg?mL(-1) against MCF7 and 3.05, 2.35?μg?mL(-1) against HCT116, respectively, while compounds 4-7 obtained from the ethyl acetate extract revealed the lowest cytotoxicity. Identification of the aforementioned compounds was carried out on the basis of their physico-chemical properties and spectral analysis (UV, EI/MS, 1D and 2D).     

Antimicrobial sesquiterpenoids from Laurus nobilis L

Activity-guided fractionations of leaf extracts from Laurus nobilis L. led to the isolation of a known sesquiterpene lactone, deacetyl laurenobiolide (1). Compound 1 showed antimicrobial activity against periopathic pathogens (Actinomyces viscosus, Porphyromonas gingivalis, Prevotella intermedia and Actinobacillus actinomycetemcomitans), opportunistic Gram-positive bacteria (Staphylococcus aureus and Streptococcus pyogenes) and fungi (Candida albicans, Cryptococcus neoformans and Aspergillus fumigatus). Furthermore, acetylation and cyclisation of deacetyl laurenobiolide (1) yielded laurenobiolide (2) and a new compound, (5S,6R,7S,8S,10R)-6,8-dihydroxyeudesma-4(15),11(13)-dien-12-oic acid 12,8-lactone (3), respectively. Compounds 2 and 3 also showed antimicrobial activities. All compounds 1-3 demonstrated growth inhibitory effects with minimum inhibitory concentrations ranging from 31 to 1000?μg?mL(-1). This is the first report of compounds 1-3 showing antimicrobial activities.     

Simultaneous estimation of hydroxychavicol and chlorogenic acid from Piper betel L. through RP-HPLC

A RP-HPLC method was developed (λ (max)?=?280) to quantify hydroxychavicol and chlorogenic acid in Piper betel Linn. The method was validated for linearity, limit of detection (LOD?=?3:1σ/S), limit of quantification (LOQ?=?10:1σ/S), precision, accuracy and ruggedness. The response was linear with good correlation between concentration and mean peak area through a coefficient of determinants (r (2)) of 0.9940, y?=?1.98e?+?004x?+?5.19e?+?004 and 0.9945, y?=?2.76e?+?004x?+?1.40e?+?005 with LOD 1.6?μg?mL(-1), 1.0?μg?mL(-1) and LOQ 5.0?μg?mL(-1) and 3.0?μg?mL(-1), respectively, for hydroxychavicol (28.56% w/w) and chlorogenic acid (0.40% w/w). The %RSD of precision and recovery of hydroxychavicol and chlorogenic acid were <2.0%. The proposed method was simple, accurate, specific, precise and reproducible.     

Antioxidant and anti-nitric oxide components from Quercus glauca

From the ethanolic extract of Quercus glauca, two new lignans, (+)-5'-methoxyisolariciresinol-9'-O-α-L-rhamnopyranoside (1) and (7R,8S)-dihydrodehydrodiconiferyl alcohol 4-β-D-xyloside (2), along with fourteen known compounds including four lignanoids (3-6), five triterpenoids (7-11), two flavonoids (12, 13), two aromatics (14, 15), and one steroid (16) were isolated. The structures of the new compounds were elucidated on the basis of spectroscopic analysis. Moreover, compounds 9 and 14 strongly inhibited nitric oxide (NO) production with IC50 values of 8.25 and 14.04?μM, respectively, and compounds 1, 4-6, 14, and 15 showed moderate antioxidant activities.     

宽叶秦岭藤根部的化学成分

通过正相和反相硅胶柱层析从宽叶秦岭藤根部乙醇提取物中分离纯化得到19个化合物,经波谱分析并结合化学方法鉴定了其结构,其中4个为新化合物,它们分别是3,5-二羟基二十烷酸羽扇豆醇酯(3),2-羟甲基-5-甲氧基苯基-O-β-D-吡喃葡萄糖甙(11),Δ5-孕甾烯-3β,20(S)-二醇-20-O-β-D-吡喃葡萄糖基(1→6)-β-D-吡喃葡萄糖甙(18,秦岭藤甙C)和Δ5-孕甾烯-3β,20(S)-二醇-3-O-β-D-吡喃葡萄糖基-20-O-β-D-吡喃葡萄糖基(1→6)-β-D-吡喃葡萄糖甙(19,秦岭藤甙D).     

Benzophenanthridine alkaloids from the roots of Thalictrum microgynum Lecoy.ex Oliv

A new benzophenanthridine alkaloid, 2,3,9-trimethoxy-7,8-methylenedioxy-5-methylbenzo[c]-6(5H) phenanthridone (2) and a benzophenanthridine alkaloid first found from natural sources, 2,3-dimethoxy-7,8- methylenedioxy-5-methylbenzo[c]-6(5H)- phenanthridone (1) together with two known benzophenanthridine alkaloids, Dihydrosanguinarine (3) and Dihydrochelilutine (4) were isolated from the roots of Thalictrum microgynum Lecoy.ex Oliv. The structures of 1 and 2 were elucidated using various spectroscopic techniques including HRESIMS and 1?D and 2?D NMR. Antibacterial activity of these compounds were tested. Compound 1, 3 and 4 showed antibacterial activity against Staphylococcus aureus with MIC values of 50, 100, 25?μg/mL, respectively.     

Studies on the constituents of Cimicifuga foetida collected in Guizhou Province and their cytotoxic activities

Two new triterpenoids and a chromone glycoside, namely, 24-epi-cimigenol-3-one (1), foetinoside (2), cimifugin-4'-O-[6″-feruloyl]-β-D-glucopyranoside (3), together with 18 known compounds, were isolated from the rhizomes of Cimicifuga foetida L. collected in Guizhou Province, China. All of the compounds were identified by spectroscopic methods, as well as chemical methods. In the in vitro cytotoxicity evaluation of these compounds against 5 human cancer cell lines, cimigenol (8) exerted the most potent cytotoxic activity against SMMC-7721 (7.87?μM) and A-549 (12.16 μM), while cimiacerin B (9) also showed obvious cytotoxicity against the A-549 cell line, with an IC(50) value of 16.77?μM.     

Two new aromatic polyketides from a deep-sea fungus Penicillium sp. SCSIO 06720

Abstract

Two new compounds, 5-[2-hydroxypropane-1-yl]-2,6-dimethlbenzene-1,3-diol (1) and coniochaetone L (2), together with 19 known compounds (3–21), were isolated from a deep-sea fungus, Penicillium sp. SCSIO 06720. Their structures and absolute configurations were elucidated by detailed NMR, MS spectroscopic analyses, chiral-phase HPLC analysis, and electronic circular dichroism spectra. All the isolated compounds (1–21) were tested for their antibacterial and HIV latency-reversal activities. Among these compounds, compound 16 showed moderate antibacterial activities against Staphylococcus aureus ATCC 29213 and Methicillin-Resistant Staphylococcus Aureus-shh-1 with MIC values of 10.4?±?3.7?μg/mL and 46.9?±?29.7?μg/mL, respectively, which were comparable to that of the positive control ampicillin with MIC values of 0.5?±?0.4?μg/mL and 2.7?±?0.9?μg/mL, respectively.     

A New Sphingolipid and Furanocoumarins with Antimicrobial Activity from <i>Ficus exasperata</i>

From the methanol extract of the stem bark of Ficus exasperata, a new sphingolipid named Ficusamide, (2S,3S,4R,11E)-2-[(2',3'-dihydroxyhexacosanoylamino)]-11-octadecene-1,3,4-triol (1), along with three known furanocoumarins, (S)-(－) oxypeucedanin hydrate (2), (R)-(+) oxypeucedanin hydrate (3), bergapten (5-methoxypsoralen) and six other known compounds, were isolated. Their structures were characterized basing on spectroscopic methods and chemical evidence. Compounds (1-3) were analyzed for their antimicrobial activity. Ficusamide (1) showed wick activity (minimal inhibitory concentration (MIC)=312.5?μg/mL) against Escherichia coli, while the furanocoumarins (2) and (3) showed significant activity (MIC=9.76?μg/mL) against Bacillus cereus, Candida albicans and Microsporum audouinii.     

Two new alkylanacardic acids, ozorcardic A and B, from Ozoroa pulcherrima

Two new alkylanacardic acids, ozorcardic A (1) and B (2), along with the known and related metabolite anacardic acid (3), were isolated from Ozoroa pulcherrima. The structures of the new compounds were elucidated by detailed spectroscopic and spectrometric analysis.     

Triterpenoid saponins from Ilex mamillata C.Y. Wu ex C.J. Tseng

Two new triterpenoid saponins, ilemaminosides A and B (1 and 2) along with six known saponins (3-8) were isolated from 70% ethanolic extract of the leaves of Ilex mamillata C.Y. Wu ex C.J. Tseng. The new saponins were characterised as 3-O-α-L-arabinopyranosyl-ilexgenin B (1) and 3-O-β-D-glucopyranosyl-(1?→?3)-α-L-arabinopyranosyl-ilexgenin B (2). The structures of compounds 1 and 2 were elucidated on the basis of the chemical and spectroscopic methods, and the structures of known compounds were identified by comparison of their spectroscopic data with those reported in the literature. The compounds showed inhibitory activities in anti-inflammatory assay in?vitro with IC(50) values in the range 25.37-38.33?μg?mL(-1).     

New benzoyl glucosides and cytotoxic pterosin sesquiterpenes from Pteris ensiformis Burm

Three new compounds: 2R,3R-pterosin L 3-O-beta-D-glucopyranoside (1), beta-D-xylopyranosyl(1-->2)-7-O-benzoyl-beta-D-glucopyranoside (2) and 4-O-benzoyl-beta-D-xylo-pyranosyl(1-->2)-7-O-benzoyl-beta-D-glucopyranoside (3), together with nine known compounds, were isolated from the ethyl acetate extract of Pteris ensiformis. 5-[2-Hydroxyethylidene]-2(5H)-furanone (4), which had been synthesized, was isolated from natural sources for the first time. The structures of all isolated compounds were determined on the basis of mass and spectroscopic evidence. Compound 1 and pterosin B (5) show cytotoxicity against HL 60 cells (human leukemia) with the IC(50) values of 3.7 and 8.7 microg/mL, respectively.     

基于子空间夹角判据监测阿司匹林合成体系中的水杨酸和阿司匹林

利用水杨酸、阿司匹林、乙酸酐和乙酸的多波长紫外光谱作为本底光谱库和样本光谱库,建立一种基于子空间夹角判据的快速定量分析阿司匹林合成体系中水杨酸和阿司匹林的方法。水杨酸、阿司匹林质量浓度范围分别在1.16～34.684,9.84～188.928μg/mL内,所测得水杨酸和阿司匹林检验集的R分别为0.999 7和0.999 1,RMSE分别为0.509 5,2.624 0μg/mL,效果优于普通波峰点最小二乘法和偏最小二乘法。水杨酸和阿司匹林的加标回收率在94.01%～106.44%之间,测定结果的相对标准偏差分别为3.45%和4.80%(n=7)。该方法可用于监测阿司匹林合成体系中的水杨酸和阿司匹林。     

A new furanocoumarin from the mangrove endophytic fungus Penicillium sp. (ZH16)

A new furanocoumarin, 5-methyl-8-(3-methylbut-2-enyl) furanocoumarin (1), together with seven known compounds, sterequinone C (2), cyclo(6,7-en-Pro-L-Phe) (3), bergapten, scopoletin, umbelliferone, 1,7-dihydroxyxanthone and 3,5-dimethoxybiphenyl, was isolated from the mangrove endophytic fungus, Penicillium sp. ZH16 obtained from the South China Sea. Their structures were determined by analysis of spectroscopic data. Compound 1 exhibited cytotoxicity against KB and KB(V)200 cells in?vitro with IC(50) values 5 and 10?μg?mL(-1), respectively.     

A novel chemiluminescent method for the determination of salicylic acid in bactericidal solutions

A new flow-injection procedure has been developed for the determination of salicylic acid based on the enhancement of the chemiluminescence from the cerium(IV)-Tween 20 reaction by salicylic acid in acidic medium. The method is simple, selective and sensitive with a detection limit of 2.5x10(-9) g mL(-1). It is applicable to the determination of salicylic acid in the concentration range of 4.0x10(-9)-1.1x10(-6) g mL(-1). The relative standard deviation (RSD) is 0.85% for 4.0x10(-7) g mL(-1) salicylic acid (n=11). The method has been successfully applied to the determination of salicylic acid in bactericidal solutions. Furthermore, it is suggested that light emission from cerium(IV)-Tween 20 reaction is probably because of the formation of singlet oxygen 1O2* and the emitter is excited oxygen molecular pairs O2(1delta(g))O2(1sigma(g)-).     

Four new isoflavonoids from the stem bark of Erythrina variegata

Bioassay-directed fractionation of the stem bark extract of Erythrina variegata L. has resulted in the isolation of three new isoflavones: 5,4'-dihydroxy-8-(3,3-dimethylallyl)-2'-methoxyisopropylfurano[4,5:6,7]isoflavone (1), 5,7,4'-trihydroxy-6-(3,3-dimethylallyloxiranylmethyl)isoflavone (2), 5,4'-dihydroxy-8-(3,3-dimethylallyl)-2'-hydroxymethyl-2'-methylpyrano[5,6:6,7]isoflavone (3) and a new isoflavanone, 5,4'-dihydroxy-2'-methoxy-8-(3,3-dimethylallyl)-2',2'-dimethylpyrano[5,6:6,7]isoflavanone (4) together with seven known compounds, euchrenone b10 (5), isoerysenegalensein E (6), wighteone (7), laburnetin (8), lupiwighteone (9), erythrodiol (10), and oleanolic acid (11). The structures were determined on the basis of spectroscopic analyses and chemical evidence. The effect of these compounds on the proliferation of rat osteogenic sarcoma (UMR106) is also reported.