Two new 2-(2-phenylethyl)chromones from Chinese eaglewood

Two new 2-(2-phenylethyl)chromones, (5S ^*,6R ^*,7S ^*)-5,6,7-trihydroxy-2-(3-hydroxy-4-methoxyphenethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one (1) and (5S ^*,6R ^*,7R ^*)-5,6,7-trihydroxy-2-(3-hydroxy-4-methoxyphenethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one (2), were isolated from the Chinese eaglewood of Aquilaria sinensis (Lour.) Gilg. Their structures were established by detailed MS and NMR spectroscopic analysis, as well as comparison with the literature data.     

中国沉香挥发油的化学成分与抗耐甲氧西林金葡菌活性

分析中国沉香的挥发油成分,并测试其抗耐甲氧西林金葡菌活性。采用水蒸气蒸馏法提取中国沉香挥发油进行GC/MS分析,峰面积归一化法计算各成分相对含量,采用NIST05和WILEY275L数据库匹配,以及将质谱图与文献数据进行对照的方法进行鉴定。采用滤纸片琼脂扩散法测试挥发油抗菌活性。挥发油对耐甲氧西林金葡菌显示强活性。共检测到66个色谱峰,其中30个化合物得到鉴定,占挥发油总量的59.80%。26个化合物被鉴定为倍半萜类化合物,占挥发油总量的54.26%。β-沉香呋喃（8.96%）,枯苏醇（7.82%）,（-）-jinkoh-eremol（5.04%）,沉香螺旋醇（4.53%）,白木香呋喃酸（4.09%）为主要的倍半萜。4个降倍半萜和其他一些倍半萜,如10-表-γ-桉叶油醇,α-沉香呋喃,epi-ligulyl oxide等为首次从中国沉香中检出。本文首次报道了中国沉香挥发油对耐甲氧西林金葡菌具有抗菌活性。     

New sesquiterpene and thiophene derivatives from Artemisia rupestris

Abstract

A new sesquiterpene, rupestrisin A (1), and three new thiophene derivatives, rupestrienes A–C (2–4), were isolated from Artemisia rupestris. Their structures were determined by analyses of MS and NMR spectroscopic data, and the absolute configuration of 1 was established by calculated ECD spectra using time-dependent density functional theory. In in vitro bioassays, compounds 1–4 showed inhibitory effects on LPS-stimulated NO production in BV-2 microglial cells with IC₅₀ values of 24.3, 20.3, 8.5, and 5.3 μM, respectively.     

A novel degraded sesquiterpene from the fresh stem of Aquilaria sinensis

A novel degraded sesquiterpene, named aquilarin B (1), together with two known compounds (2 and 3), was isolated from the EtOH extract of the fresh stem of Aquilaria sinensis (Lour.) Gilg. Their structures were elucidated by spectroscopic methods including 1D and 2D NMR (HMQC, ¹H–¹H COSY, HMBC, and ROESY). The cytotoxic activities of the three compounds against three human tumor cell lines K562, SMMC-7721, and SGC-7901 were evaluated, and compound 3 exhibited obvious cytotoxic activity.     

Two new sesquiterpene lactone glycosides from Artemisia frigida Willd.

The investigation of EtOAc-soluble fraction from the aerial parts of Artemisia frigida has led to the isolation of two new sesquiterpene lactone glycosides, named as artemofriginoside A and artemofriginoside B. Their structures were characterized as 3β-(β-d-glucopyranosyloxy)-8β-(p-hydroxyphenylacetyloxy)-4(15),10(14),11(13)-guaiatrien-1α,5β,6β,7αH-12,6-olide (1) and β-(β-d-glucopyranosyloxy)-8β-(2-hydroxy-3-methylbutanoyloxy)-4(15),10(14),11(13)-guaiatrien-1α,5β,6β,7αH-12,6-olide (2), on the basis of 1D and 2D NMR spectral analysis.     

Two new sesquiterpene glucosides from the leaves of Nicotiana tabacum

Two new sesquiterpene glycosides, 11R,12-dihydroxy-6(7)-spirovetiven-8-one-9-O-β-d-glucopyranoside (1) and rishitin M1-13-O-β-d-glucopyranoside (2), have been isolated from the leaves of Nicotiana tabacum. Their structures were established by spectroscopic methods including ¹H, ¹³C, and 2D NMR. The absolute configuration of the side chain in compound 1 was determined as R by NOESY and NOE difference spectra.     

Talaflavuterpenoid A,a new nardosinane-type sesquiterpene from Talaromyces flavus

Talaflavuterpenoid A (1), a new nardosinane-type sesquiterpene, was isolated from the wetland soil-derived fungus Talaromyces flavus BYD07-13, and its structure was elucidated on the basis of HR-MS, NMR, and X-ray diffraction analysis. The absolute configuration of 1 was established by comparing the experimental electronic circular dichroism (ECD) spectrum with the calculated ECD spectra. Its cytotoxic effects on five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480), and antimicrobial activity against Escherichia coli, Staphylococcus aureus, Candida albicans, and Aspergillus niger were evaluated. This is the first report of the presence of nardosinane-type sesquiterpene in Talaromyces sp.     

Two new guaiane sesquiterpene lactones from the aerial parts of Artemisia vulgaris

Abstract

Two new guaiane sesquiterpene lactones, vulgarolides A and B (1 and 2), were isolated from Artemisia vulgaris aerial parts using various chromatographic separations. The structure elucidation was performed by combination of spectroscopic experiments including 1D and 2D NMR, HR ESI MS, and CD. Their in vitro cytotoxic activities against five human cancer cell lines were also evaluated using SRB method.     

Two new sesquiterpene lactones from leaves of yacon,Smallanthus sonchifolius

The chemical constituents of 95% EtOH extract of yacon leaves were separated to yield two new sesquiterpene lactones, together with three known compounds. The two new compounds were characterized to be 8β-angeloyloxy-13-methoxyl-11, 13-dihydromelampolid-14-oic acid methyl ester (1) and 8β-(3-methylbut-2-enoyl) oxy-13-methoxyl-11, 13-dihydromelampolid-14-oic acid methyl ester (2) on the basis of NMR spectra, HR-MS and other spectroscopic methods. The cytotoxicity of compounds 1–5 were evaluated on human hepatoma cell Bel-7402 and all the compounds showed moderate cytotoxicity.     

大花八角果皮中两个新的倍半萜内酯类化合物

为了研究大花八角的化学成分, 通过硅胶柱色谱等方法进行化合物的分离纯化, 利用色谱和多种波谱技术鉴定化合物结构。从甲醇浸提物的二氯甲烷-乙酸乙酯 (1∶1) 部分和乙酸乙酯部分, 分离得到11个化合物, 其中2个新化合物, 分别命名为6-去氧新大八角素 (6-deoxyneomajucin, 1)、2-氧代-6-去氧新大八角素 (2-oxo-6-deoxyneomajucin, 2), 9个为已知化合物: 6-去氧伪莽草毒素 (3)、伪莽草毒素 (4)、莽草毒素 (5)、伪大八角素 (6)、原儿茶酸 (7)、莽草酸 (8)、莽草酸甲酯 (9)、β-谷甾醇 (10) 和胡萝卜苷 (11)。化合物1和2为新的大八角素型倍半萜内酯类化合物, 其余化合物均为首次从本植物中分离得到。     

Two new sesquiterpene lactones from the supercritical fluid extract of Centipeda minima

Two new sesquiterpene lactones, minimolides G (1) and H (2), were isolated from the supercritical fluid extract of Centipeda minima. Their structures were elucidated on the basis of extensive analyses of spectroscopic data including IR, HR-ESI-MS, 1D and 2D NMR. Compounds 1 and 2 displayed inhibitory activity against human nasopharyngeal cancer cell line (CNE) with IC₅₀ values of 61.4 and 28.7 μM, respectively.     

Two new sesquiterpene glycosides from Pogostemon cablin

Two new rearranged patchoulane sesquiterpene glycosides, 3α-hydroxypatchoulol 3-O-β-d-glucopyranoside (1) and 15-hydroxypatchoulol 15-O-β-d-glucopyranoside (2) together with rubusoside, a known diterpene glycoside, were isolated from the ethanol extract of the whole plant of Pogostemon cablin (Blanco) Benth. The structures of 1 and 2 were elucidated by spectroscopic analysis.     

Two new sesquiterpene polyol esters from the root barks of Celastrus angulatus

Angulatin F (1) and angulatin I (2), two new sesquiterpene polyol esters, were isolated from the root barks of Celastrus angulatus, together with six known compounds 1β,2β-diacetoxy-4α,6α-dihydroxy-8α-isobutanoyloxy-9β-benzoyloxy-15-(α-methyl) butanoyloxy-β-dihydroagrofuran (3), angulatin A (4), angulatin B (5), celangulatin E (6), 1β,2β,15-triacetoxy-4α,6α-dihydroxy-8α-isobutanoyloxy-9β-benzoyloxy-β-dihydroagrofuran (7), and celangulin I (8). The structures of 1 and 2 were elucidated as 1β,2β,6α,15-tetraacetoxy-4α-hydroxy-8β,9α-difuroyloxy-β-dihydroagrofuran and 1β,2β,6α,8β,15-pentaacetoxy-4α-hydroxy-9β-furoyloxy-β-dihydroagrofuran by spectroscopic means.     

A new picrotoxane-type sesquiterpene from Dendrobium findlayanum

A new picrotoxane-type sesquiterpene, findlayanin (1), was isolated from Dendrobium findlayanum with crystallinin (2). The structure of compound 1 was established to be (1R,2S,3R,4S,5R,6S,9R)-2,3,11,12-tetrahydroxypicrotoxan-12(15)-lactone by spectroscopic methods.     

A new sesquiterpene lactone from Elephantopus tomentosus

A new sesquiterpene lactone, named tomenphantopin H (1), together with two known germacranolides, 2β-methoxy-2-deethoxy-8-O-deacylphantomolin-8-O-tiglinate (2) and 2-deethoxy-2-hydroxyphantomolin (3), was isolated from the whole plant of Elephantopus tomentosus Linn. The new compound was completely elucidated using a combination of 1D and 2D NMR techniques (COSY, HMQC, and HMBC) and HR-ESI-MS analyses. All compounds exhibited antibacterial activity.     

A new eudesmane sesquiterpene glycosides from Liriope muscari

A new eudesmane sesquiterpene glycoside, ophiopogonoside B (1), along with five known compounds, ophiopogonoside A (2), ruscogenin-1-O-[β-d-glucopyranosyl (1 → 2)]-[β-d-xylopyranosyl (1 → 3)]-β-d-fucopyranoside (3), palmitic acid (4), palmitic acid glyceride (5), and β-sitosterol-d-glucopyranoside (6),was isolated from the tuberous roots of Liriope muscari (Decn.) Bailey (Liliaceae). Their structures were confirmed by 1D and 2D NMR spectroscopy. Among them, compounds 1, 2, 4, and 5 were the first reported from the genus Liriope. Ophiopogonoside B (1) showed moderate inhibitory activity to glycogen phosphorylase a.     

Cryptoporic acid S,a new drimane-type sesquiterpene ether of isocitric acid from the fruiting bodies of Cryptoporus volvatus

A new drimane-type sesquiterpene with an isocitric acid moiety, cryptoporic acid S (1), together with six known compounds, cryptoporic acid D (2), β-sitosterol (3), β-daucosterol (4), stigmast-4-en-3-one (5), ergosterol (6), and (22E,24R)-ergosta-7,22-diene-3β,5α,6β-triol (7), was isolated from the fruiting bodies of Cryptoporus volvatus. The structures of these compounds were established on the basis of UV, IR, MS, 1D and 2D NMR analysis. In the meanwhile, compounds 1 and 2 were evaluated for antioxidant activity using the methods of 2,2-diphenyl-1-picrylhydrazyl free radical scavenging activity (DPPH-RSA) and ferric reducing antioxidant power (FRAP) assay, and they exhibited moderate antioxidant activities.     

A new elemanolide sesquiterpene lactone from Elephantopus scaber

A new elemanolide sesquiterpene lactone, named elescaberin (1), together with two known compounds, namely, isodeoxyelephantopin (2) and deoxyelephantopin (3), was isolated from the whole plant of Elephantopus scaber. The structure of 1 was elucidated on the basis of spectroscopic analysis. All three compounds exhibited significant inhibitory activities against human SMMC-7721 liver cancer cells in vitro (IC₅₀ 8.18–14.08 μmol/l).     

Synthesis,characterization, molecular docking evaluation,antidepressant, and anti-Alzheimer effects of dibenzylidene ketone derivatives

Novel bioactive compounds as synthetic analogs of the potent herbal medicines can be optimized as potential drug candidates for various neurologic disorders. This study was performed to investigate the newly synthesized dibenzylidene ketone derivatives: (2E,6E)-2,6-dibenzylidene cyclohexanone (A1K1) and (1E,4E)-5-(2,3-dichlorophenyl)-1-(4-methoxyphenyl)-2-methylpenta-1,4-diene-3-one (A2K2) and evaluate its potential anti-Alzheimer's and anti-depressant properties. Both the derivatives are chemically characterized by using HNMR and CNMR techniques. Auto Dock Vina program was used to investigate ligand-protein affinity. Forced swim test, tail suspension test, open field test, Y-maze test, and Morris water maze test (MWM) models were employed to evaluate anti-depressant and anti-Alzheimer's activity of dibenzylidene ketone derivatives in mice. Both A1K1 and A2K2 showed high binding affinities against various proteins involved in depression and Alzheimer's mechanisms like monoamine oxidase B, acetylcholinesterase, norepinephrine transporter 2, serotonin transporter, dopamine receptor, serotonin receptor modulator, and beta-amyloid targets. A1K1 and A2K2 dose-dependently (0.1–1 mg/kg) decreased immobility time, while increased swimming and climbing time of mice in forced swim test (FST). A1K1 and A2K2 decreased animal immobility time in TST. In the open field test, both A1K1 and A2K2 increased the number of ambulations and rearings. A1K1 and A2K2 dose-dependently (0.5–1.0 mg/kg) increased spontaneous alternation behavior (%) and the number of entries of mice in Y-maze test. In the MWM test, A1K1 and A2K2 decreased escape latency time. Overall, both in-silico and in-vivo investigations of A1K1 and A2K2, report their therapeutic potential for antidepressant and anti-Alzheimer properties. Hence, these compounds possess potent neuroprotective properties and may be further evaluated for their therapeutic potential in various neurological disorders.     

温郁金中的新桉叶烷型倍半萜內酯

为了研究温郁金(Curcuma wenyujin Y.H. Chen et C. Ling)根茎中的倍半萜类成分，采用大孔树脂和反复硅胶柱色谱对温郁金干燥根茎的50%乙醇提取物进行分离纯化，得到8个倍半萜类化合物1～8；其化学结构通过多种波谱方法分别鉴定为温郁金内酯A(wenyujinlactone A，1)、neolitamone A (2)、zedoarondiol (3)、isozedoarondiol (4)、aerugidiol (5)、莪术醇(curcumol，6)、莪二酮(curdione，7)和(1R,10R)-epoxy-(-)-1,10-dihydrocurdine (8)。化合物1为新的桉叶烷型倍半萜内酯，化合物2～5为首次从该植物中分离得到。