A cytotoxic sesquiterpene alkaloid from the South China Sea gorgonian Subergorgia suberosa

A new sesquiterpene alkaloid, 6-(9'-purine-6',8'-diolyl)-2beta-suberosanone (1), together with three known sesquiterpenes, suberosenol A (2), subergorgic acid (3), and subergorgiol (4), was isolated from the EtOH/CH2Cl2 extracts of the South China Sea gorgonian Subergorgia suberosa. The structure of 1 was determined through spectroscopic methods. Compound 1 showed moderate cytotoxicity against the human breast carcinoma MDA-MB-231 cell line with an IC50 of 8.87 microg/mL.     

穗花蛇菰的化学成分研究

目的：研究穗花蛇菰的化学成分。方法：采用硅胶柱色谱和反相制备色谱对化合物进行分离纯化,应用IR,NMR,MS等波谱法进行结构鉴定。结果：从穗花蛇菰中分离得到8个化合物,分别为蛇菰素A(1),蛇菰素B(2),β-香树脂醇乙酸酯(3),Monogynol A(4),羽扇豆酮(5),咖啡酸乙酯(6),儿茶素(7),1-O-(E)-caffeoyl-3-O-galloyl-β-D-glucopyranose(8)。结论：所有化合物均为首次从该植物中分得,其中化合物4为首次从该属植物中分得。     

草泽泻三萜类化学成分的研究

目的:研究草泽泻三萜类化学成分。方法:利用硅胶柱色谱和HPLC色谱进行分离纯化,运用NMR,MS,IR等光谱手段进行结构鉴定。结果:分离得到了5个原萜烷型四环三萜类化合物,分别为:16,23-氧化泽泻醇B(1),11-去氧泽泻醇C(2),泽泻醇F(3),16β-甲氧基泽泻醇B单乙酯(4),16β-羟基泽泻醇B单乙酯(5)。结论:所有化合物均为首次从该植物中分离得到。     

Determination of the absolute configurations of natural products via density functional theory calculations of optical rotation, electronic circular dichroism, and vibrational circular dichroism: the cytotoxic sesquiterpene natural products quadrone, suberosenone, suberosanone, and suberosenol A acetate

The determination of the absolute configurations (ACs) of chiral molecules using the chiroptical techniques of optical rotation (OR), electronic circular dichroism (ECD), and vibrational circular dichroism (VCD) has been revolutionized by the development of density functional theory (DFT) methods for the prediction of these properties. Here, we demonstrate the significance of these advances for the stereochemical characterization of natural products. Time-dependent DFT (TDDFT) calculations of the specific rotations, [alpha](D), of four cytotoxic natural products, quadrone (1), suberosenone (2), suberosanone (3), and suberosenol A acetate (4), are used to assign their ACs. TDDFT calculations of the ECD of 1 are used to assign its AC. The VCD spectrum of 1 is reported and also used, together with DFT calculations, to assign its AC. The ACs of 1 derived from its [alpha](D), ECD, and VCD are identical and in agreement with the AC previously determined via total synthesis. The previously undetermined ACs of 2-4, derived from their [alpha](D) values, have absolute configurations of their tricyclic cores identical to that of 1. Further studies of the ACs of these molecules using ECD and, especially, VCD are recommended to establish more definitively this finding. Our studies of the OR, ECD, and VCD of quadrone are the first to utilize DFT calculations of all three properties for the determination of the AC of a chiral natural product molecule.     

Chemical constituents of the ascomycete Daldinia concentrica

Four compounds, daldinone A (1), daldinone B (2), daldiniapyrone (4-methoxy-5-carbomethoxy-6-pentyl-2H-pyran-2-one, 3), and daldinialanone (22R-hydroxylanosta-7,9(11),24-trien-3-one, 4), were isolated from an ethyl acetate extract of fruit bodies of Daldinia concentrica collected in Europe. In addition, 11 known compounds, 4:5:4':5'-tetrahydroxy-1:1'-binaphthyl (5), 3,4,5-trihydroxy-1-tetralone (6), (+)-orthosporin (7), curuilignan D (8), (22E)-cholesta-4,6,8(14),22-tetraen-3-one (9), 3beta,22-dihydroxylanosta-7,9(11),24-triene (10), concentricol (11), concentricol B (12), concentricol C (13), concentricol D (14), and phenochalasin B (15), were obtained. The structures of the new compounds were elucidated by 2D NMR, MS, IR, and UV spectra and by X-ray crystallographic analysis. The absolute configurations of 1 and 4 were determined by CD spectroscopy and the modified Mosher's method, respectively. The chemotaxonomic relevance of the compounds obtained in this investigation is discussed.     

Chaetocochins A-C, epipolythiodioxopiperazines from Chaetomium cochliodes

Three new epipolythiodioxopiperazines, chaetocochins A (1), B (2), and C (3), along with dethio-tetra (methylthio) chetomin (4) and chetomin (5), were isolated from the ethyl acetate extract of the solid-state fermented rice culture of the fungus Chaetomium cochliodes. Their structures were elucidated on the basis of spectroscopic analysis. Compounds 1, 3, and 4 exhibited significant cytotoxicity in vitro against cancer cell lines Bre-04, Lu-04, and N-04.     

小蓟三萜类化合物成分的研究

对小蓟乙醇提取物中显示细胞毒活性的石油醚萃取部位进行化学成分的系统研究。运用正反相硅胶、凝胶、反相高效液相等色谱方法进行分离;应用NMR和MS等波谱学方法,并结合文献对照确定化合物结构。从小蓟乙醇提取物的石油醚萃取部位分离得到12个三萜类化合物,分别鉴定为羽扇豆醇乙酸酯(1),羽扇豆醇(2),羽扇豆酮(3),β-香树酯醇(4),伪蒲公英甾醇(5),伪蒲公英甾醇乙酸酯(6),蒲公英甾醇乙酸酯(7),marsformoxide B(8),α-香树酯酮(9),β-香树酯酮(10),蒲公英甾酮(11),伪蒲公英甾酮(12)。化合物3,5,7～12为首次从蓟属植物中分离得到。     

高效液相色谱法同时测定黄芪赤风胶囊中芍药苷、升麻素苷等9种成分的含量

 目的 建立HPLC同时测定黄芪赤风胶囊中9种成分的含量。方法 采用Waters Symmetry Shield RP₁₈（4.6 mm×150 mm,5 μm）色谱柱;以甲醇（A）-水溶液（B）为流动相进行梯度洗脱（0～15 min,5%A→20%A;15～55 min,20%A→35%A;55～100 min,35%A→85%A）,流速1.0 mL·min^-1;检测波长：230 nm（0～25 min,芍药苷）,254 nm（25～100 min,毛蕊异黄酮苷等）;柱温35 ℃。结果 芍药苷、升麻素苷、毛蕊异黄酮苷、升麻素、5-O-甲基维斯阿米醇苷、芒柄花苷、亥茅酚苷、毛蕊异黄酮、芒柄花素的线性范围分别为1.51～15.10,0.047～0.94,2.192～10.960,0.052 2～1.044,0.041 4～0.828,1.56～7.80,0.042 2～0.844,0.149～0.744和0.110～0.552 μg（r≥0.999 0）;平均回收率（n=6）分别为99.48%（RSD=2.59%）,103.15%（RSD=1.69%）,102.77%（RSD=1.56%）,99.27%（RSD=2.72%）,101.99%（RSD=2.36%）,102.25%（RSD=2.10%）,101.49%（RSD=3.00%）,100.45%（RSD=1.76%）和97.49%（RSD=2.03%）。结论 所建立的方法快速、准确、专属性强、精密度好,可用于黄芪赤风胶囊的质量控制。     

Cytotoxic sesquiterpene lactones from Pseudoelephantopus spicatus

Five new sesquiterpene lactones, spicatolides D-H (1-5), along with four known compounds, pitocarphin D (6), 8 alpha-acetoxy-10 alpha-hydroxy-13-O-methylhirsutinolide (7), spicatolide A (8), and 13-O-methylvernojalcanolide 8-O-acetate (9), were isolated from an ethyl acetate extract of the aerial parts of Pseudoelephantopus spicatus. The structures of the new compounds were elucidated on the basis of spectroscopic data interpretation. All of the compounds isolated were evaluated for their cytotoxic effects against five human cancer cell lines. Compounds 1, 3, and 4 showed cytotoxicity (IC50 < 5 micro g/mL) against the Hep3B and MCF-7 cancer cell lines.     

蒙古蒲公英的化学成分研究

目的:研究蒙古蒲公英Taraxacum mongolicum的化学成分。方法:采用色谱法分离化学成分,波谱法鉴定其结构。结果:从蒙古蒲公英全草中分离并鉴定了44个化合物,包括16个黄酮类衍生物(1~16),15个酚酸类化合物(17~31),1个香豆素类化合物(32),2个木脂素类化合物(33~34),4个倍半萜(35~38),3个三萜类化合物(39~41),1个长链脂肪酸类化合物(42),2个甾体类化合物(43~44)。结论:其中化合物14,15,34,35为新化合物,分别命名为:isoetin-7-O-β-D-glucopyranosyl-2′-O-α-L-arabinopyranoside(14),isoetin-7-O-β-D-glucopyranosyl-2′-O-α-D-glucopyranoside(15),蒙古蒲公英素A(6,9,10-trihydroxy-benzoxanthene-1,2-dicarboxylic acid,mongolicuminA,34),蒙古蒲公英素B(11-hydroxy-2-oxo-guaia-1(10),3,5-trien-8,12-lactone,mongolicumin B,35);化合物1,3,6~13,20~22,30,31为首次从本属植物中分离得到,化合物18,23~29,32,37~42为首次从该种植物中分离得到。     

祁门红茶抗氧化有效成分的研究

祁门红茶有较强的抗芥花子油氧化的活性.从祁门红茶乙酸乙酯部位,使用硅胶柱层析,结合Sephadex LH-20柱层析方法,分离得到了四个抗氧化有效成分,分别为茶黄素(Theaflavin,TF1)、茶黄素A(Theaflavin-3-galate,TF2A)、茶黄素B(Theaflavin-3'-gallate,TF2B)和茶黄素双没食子酸酯(Theaflavin digallate,TF3).     

毛白杨化学成分研究

目的:对毛白杨雄株干皮进行化学成分的分离鉴定。方法:毛白杨的新鲜干皮用甲醇提取,所得浸膏用水混悬后依次用石油醚、醋酸乙酯、正丁醇萃取,对醋酸乙酯和正丁醇部分采用各种柱色谱进行分离纯化,根据理化性质并通过波谱数据的解析进行结构鉴定。结果:从醋酸乙酯和正丁醇部分获得12个化合物,分别鉴定为苯甲酸(1),胡萝卜苷(2),苯甲酰水杨苷(3),鼠李柠檬素(4),樱花素(5),7-O-甲基香橙素(6),异大齿杨苷A(7),siebolside B(8),樱花苷(9),micranthoside(10),α-D-葡萄糖(11),蔗糖(12)。结论:化合物4～12为首次从该植物中分离得到,其中化合物10为首次从该属植物中得到。     

��Ұͩ���㶹���໯ѧ�ɷֵ��о�

??OBJECTIVE To study the coumarins from Mallotus conspurcatus. METHODS The ethyl acetate part of 75% ethanol extracts from Mallotus conspurcatus was isolated. The compounds were isolated and purified with column chromatography, and their structures were elucidated on the basis of ¹H-NMR, ¹³C-NMR and ESI-MS data. RESULTS Twelve coumarins were determined to be malloapelin A (1), 5??-demethyl aquillochin (2), aquillochin (3), cleomiscosin B (4), 6-hydroxy-7-methoxy-coumarin (5), braylin (6), aegelinol (7), bergapten (8), isofraxidin (9), fraxidin (10), grevillone (11), and fraxetin (12). CONCLUSION Compounds 6-12 are isolated from this genus for the first time.     

Anti-influenza virus polyketides from the acid-tolerant fungus Penicillium purpurogenum JS03-21

Fractionation of the ethyl acetate extract of an acid-tolerant fungus, Penicillium purpurogenum JS03-21, resulted in the isolation of six new compounds, purpurquinones A-C (1-3), purpuresters A and B (4 and 5), and 2,6,7-trihydroxy-3-methylnaphthalene-1,4-dione (6), together with three known compounds, TAN-931 (7), (-)-mitorubrin (8), and orsellinic acid. The structures of 1-6 were elucidated primarily by NMR experiments. The absolute configurations of 1-4 were assigned on the basis of CD and NOESY data. Compounds 2-4 and 7 exhibited significant antiviral activity against H1N1, with IC50 values of 61.3, 64.0, 85.3, and 58.6 μM, respectively.     

Cytotoxic alkaloids and antibiotic nordammarane triterpenoids from the marine-derived fungus Aspergillus sydowi

Three new diketopiperazine alkaloids, 6-methoxyspirotryprostatin B (1), 18-oxotryprostatin A (2), and 14-hydroxyterezine D (3), with an oxaspiro[4.4]lactam moiety, 14-norpseurotin A (4), and the 29-nordammarane triterpenoid 6beta,16beta-diacetoxy-25-hydroxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid (5), as well as 12 known compounds (6- 17), were isolated from the ethyl acetate extract of a marine-derived fungal strain, Aspergillus sydowi PFW1-13. The structures of compounds 1- 5 were elucidated by comprehensive spectroscopic analysis. Compounds 1- 3 exhibit weak cytotoxicity against A-549 cells, with IC 50 values of 8.29, 1.28, and 7.31 microM, respectively. Compound 1 also shows slight cytotoxicity against HL-60 cells, with an IC 50 value of 9.71 microM. Compounds 4 and 5 display significant antimicrobial activities against Escherichia coli, Bacillus subtilis, and Micrococcus lysoleikticus with MICs of 3.74, 14.97, and 7.49 microM and 10.65, 5.33, and 10.65 microM, respectively.     

New bromoterpenes from the red alga Laurencia luzonensis.

Extraction of a sample of Laurencia luzonensis collected off the coast of Kudaka Island, Okinawa, yielded the known sesquiterpenes palisol (1), palisadin B (2), palisadin A (3), pacifigorgiol (4), and aplysistatin (5), together with five new bromosesquiterpenes, isopalisol (6), luzonensol (7), luzonensol acetate (8), luzonensin (9), and (3Z,6E)-1-bromo-2-hydroxy-3,7,11-trimethyldodeca-3,6,10-triene (10). In addition, a new bromoditerpene of unusual structure, 3-bromobarekoxide (11), possessing a seven-membered ring fused to trans-decalin, was isolated.     

Sesquiterpenoid derivatives from Gonospermum elegans and their cytotoxic activity for HL-60 human promyelocytic cells

Four new compounds, a sesquiterpene, eleganodiol (1), and three sesquiterpene lactones, eleganolactone A (2), eleganolactone B (3), and elegain (4), were isolated from Gonospermum elegans along with 16 known compounds. The structures of 1, 2, and 4 were determined on the basis of MS and NMR studies of their acetate derivatives (1a, 2a, 4a). The structure of the acetate derivative (3a) of 3 was determined on the basis of spectroscopic data interpretation and by single-crystal X-ray diffraction. Compounds 2a and 3a were used to study their biological activities on the HL-60 human promyelocytic leukemia cell line. These compounds induced morphological changes and internucleosomal DNA fragmentation characteristic of apoptotic cell death.     

Immunosuppressive decalin derivatives from red yeast rice

Five new decalin derivatives (1-5), together with two known compounds (6 and 7), were isolated from the ethyl acetate extract of red yeast rice. Their structures were elucidated by means of NMR and mass spectroscopic analyses. Monascusic lactone A (1) is the first reported naturally occurring decalin derivative possessing a spiro lactone at the C-1 position. The immunosuppressive effects of all these isolates (1-7) on human T cell proliferation were investigated, and all, especially monascusic acids B (2), C (3), D (4), and A (6) and heptaketide (7), suppressed human T cell proliferation in a dose-dependent manner from 10 to 100 μM. This is the first report on the immunosuppressive activity of decalin derivatives.     

Antimycobacterial compounds from Piper sanctum

Bioassay-guided chromatographic separation of the antimycobacterial extract of the leaves of Piper sanctum afforded 14 new compounds, identified as 2-oxo-12-(3',4'-methylenedioxyphenyl)dodecane (1), 2-oxo-14-(3',4'-methylenedioxyphenyl)tetradecane (2), 2-oxo-16-(3',4'-methylenedioxyphenyl)hexadecane (3), 2-oxo-18-(3',4'-methylenedioxyphenyl)octadecane (4), 2-oxo-14-(3',4'-methylenedioxyphenyl)-trans-13-tetradecene (5), 2-oxo-16-(3',4'-methylenedioxyphenyl)-trans-15-hexadecene (6), 2-oxo-18-(3',4'-methylenedioxyphenyl)-trans-17-octadecene (7), 2-oxo-16-phenyl-trans-3-hexadecene (8), methyl [6-(10-phenyldecanyl)tetrahydropyran-2-yl]acetate (9), methyl 2-(6-tridecyltetrahydro-2H-pyran-2-yl)acetate (10), methyl 2-(5-tetradecyltetrahydro-2-furanyl)acetate (11), 2-oxo-14-(3',4'-methylenedioxyphenyl)-trans-3-tetradecene (12), 2-oxo-16-(3',4'-methylenedioxyphenyl)-trans-3-hexadecene (13), and 2-oxo-16-phenyl-3-hexadecane (14). In addition, p-eugenol (15), methyleugenol (16), Z-piperolide (17), demethoxyyangonin (18), 5,6-dehydro-7,8-dihydromethysticin (19), cepharanone B (20), piperolactam A (21), cepharadione B (22), N-trans-feruloyltyramine (23), and N-trans-(p-coumaroyl)tyramine (24) were obtained from the anti-TBC stem extract of the plant. GC-MS and HPLC analyses of the essential oils of the leaves and stem revealed that safrol (25) was the major component of the oils. Compounds 2, 3, 6, 18-21, and 24 inhibited the growth of Mycobacterium tuberculosis when tested by the MABA assay, with MIC values ranging from 4 to 64 microg/mL.     

蒙古鸦葱抗肿瘤三萜类成分研究

 目的 系统研究蒙古鸦葱的抗肿瘤活性成分。方法 使用硅胶H、Sephadex LH-20、ODS和HPLC分离、纯化,根据理化性质和光谱分析鉴定化合物的结构。采用MTT法和SRB法进行活性跟踪和单体化合物的抗肿瘤活性筛选。结果 分离鉴定了15个三萜类化合物,分别为羽扇豆醇(1)、白桦脂醇(2)、白桦脂酸(3)、乙酰羽扇豆醇(4)、23Z-3β-acetoxyeupha-7, 23-diene-25-ol(5)、达玛二烯醇乙酸酯 (6)、齐墩果烷乙酸酯(7)、蒲公英甾醇(8)、蒲公英甾醇乙酸酯(9)、伪蒲公英甾醇(10)、伪蒲公英甾醇乙酸酯(11)、α-乙酰香树脂醇(12)、达玛-24-烯-3β-十四酰氧基-20S-醇(13)、大戟烷-8,24-二烯-3-醇乙酸酯(14)和multiflorenyl acetate (15)。结论 1～15均为首次从蒙古鸦葱中分离得到,其中2,3,5～15为首次从该属中分离得到。药理实验表明,在50 mg·L-1质量浓度下,化合物1～5对人肺癌细胞A-549、14对人肝癌细胞株Bel-7402显示有意义的细胞毒活性。