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1.
Investigation of extracts of Fissistigma balansae and Fissistigma oldhamii resulted in the isolation of 11 aristolactams-stigmalactam (1), piperolactam A (2), piperolactam C (3), aristolactam AII (4), aristolactam AIIIa (5), aristolactam BII (6), aristolactam BIII (7), aristolactam FII (8), goniothalactam (9), enterocarpam I (10), and velutinam (11)-as well as two dioxoaporphines, noraristolodione (12) and norcepharadione B (13). The new compound 1 was identified by spectral data interpretation. Compounds 1-13 were subjected to antiplatelet aggregation testing. 相似文献
2.
Torres-Valencia JM Chávez-Ríos OE Cerda-García-Rojas CM Burgueño-Tapia E Joseph-Nathan P 《Journal of natural products》2008,71(11):1956-1960
Chemical investigations of Prionosciadium thapsoides roots led to the isolation of the new dihydrofurochromones (S)-(+)-4'-O-angeloyl-5-O-methylvisamminol (1) and (S)-(+)-4'-O-senecioyl-5-O-methylvisamminol (2), together with the known coumarins jatamansin, buchtormin, isopteryxin, isosamidin, psoralen, and bergapten. The structures of 1 and 2 were determined by 1D and 2D NMR experiments, and their absolute configuration was established by chemical correlation with (+)-5-O-methylvisamminol (3), whose structure was secured by single-crystal X-ray diffraction analysis and its absolute configuration was established as S by vibrational circular dichroism spectroscopy in comparison to DFT B3LYP/DGDZVP calculations. 相似文献
3.
Four new diterpenoids with the briarane skeleton, (-)-4-deacetyljunceellolide D (2), (+)-11alpha, 20alpha-epoxyjunceellolide D (3), (-)-11alpha, 20alpha-epoxy-4-deacetyljunceellolide D (4), and (-)-11alpha, 20alpha-epoxy-4-deacetoxyjunceellolide D (5), (+)-junceellolide A (6) [the antipodal derivative of the known (-)-junceellolide A], along with three known briaranes, (-)-junceellolide D (1), (-)-junceellin (7), and (-)-praelolide (8), were isolated from the Indonesian gorgonian Junceella fragilis. The structures of the new compounds were established on the basis of extensive NMR studies and by comparison with the spectral data from other briarane compounds. The absolute configurations for four of the compounds were determined by the modified Mosher method and by unambiguous chemical interconversions. 相似文献
4.
Hernández-Hernández JD Román-Marín LU Cerda-García-Rojas CM Joseph-Nathan P 《Journal of natural products》2005,68(11):1598-1602
The stems of Bursera suntui afforded two new verticillane derivatives, (1S,3Z,7E,11S,12S)-(+)-verticilla-3,7-dien-12,20-diol (1) and (1S,3Z,7E,11S,12S)-(+)-verticilla-3,7-dien-12,20-diol 20-acetate (2), together with (1S,3E,7E,11R)-(+)-verticilla-3,7,12(18)-triene (3), (1R,3E,7E,11R,12Z)-(+)-verticilla-3,7,12-triene (4), (1R,7E,11Z)-(-)-verticilla-4(20),7,11-triene (5), and (1S,3E,7E,11S,12S)-(+)-verticilla-3,7-dien-12-ol (6). Compounds 3 and 4 are new enantiomerically pure natural products whose racemic mixtures, derived from synthetic approaches toward the taxane skeleton, were obtained previously. The stems of Bursera kerberi afforded the new (1S,3E,7E,11S,12R)-(+)-verticilla-3,7-dien-12-ol (7) together with 3-5. This is the first time that verticillane derivatives have been isolated from the genus Bursera. Their structures and stereochemistry were elucidated by 1D and 2D NMR data, including COSY, NOESY, HSQC, and HMBC experiments, while the absolute configuration was determined by comparison of the optical rotatory dispersion data with that of recently revised (1S,3E,7E,11S,12S)-(+)-verticilla-3,7-dien-12-ol (6), obtained from Sciadopitys verticillata, and those of (1R,3E,7E,11R,12R)-(-)-verticilla-3,7-dien-12-ol (8) and (1R,3E,7E,11R,12S)-(-)-verticilla-3,7-dien-12-ol (9), isolated from the liverwort Jackiella javanica. The conformational preferences of 1-7 were studied by molecular mechanics modeling employing the Monte Carlo protocol. 相似文献
5.
Acuña UM Figueroa M Kavalier A Jancovski N Basile MJ Kennelly EJ 《Journal of natural products》2010,73(11):1775-1779
Two new polyisoprenylated benzophenones, 32-hydroxy-ent-guttiferone M (1) and 6-epi-guttiferone J (2), along with seven known compounds, 6-epi-clusianone (3), guttiferone A (4), xanthochymol (5), guttiferone E (6), isoxanthochymol (7), (+)-volkensiflavone (8), and (+)-morelloflavone (9), were identified from the seeds and rinds of Rheedia edulis. Compounds 1-3 and 5-9 have been isolated and identified from this species for the first time. The structures of the new compounds were elucidated mainly by analysis of their 1D and 2D NMR spectroscopic data, and their absolute configurations were determined by comparison of their experimental optical rotation and electronic circular dichroism measurements with those values predicted by DFT calculations. Compound 1 showed significant antioxidant activity in both DPPH and ABTS free radical scavenging assays, whereas compound 2 was inactive. 相似文献
6.
Two aristololactam analogues were isolated from the extract of Saururus cernuus. One of these was the known aristololactam BII [1] (cepharanone B) and the other new, named sauristolactam [2], was shown to be the lactam of 10-aminomethyl-3-hydroxy-4-methoxyphenanthrene-1-carboxylic acid. Here we detail the first reported occurrence of compounds of the aristolactam group in the genus Saururus. 相似文献
7.
Seven new cadinane sesquiterpenes, (-)-(1R,6S,7S,10R)-1-hydroxycadinan-3-en-5-one (1), (+)-(1R,5S,6R,7S, 10R)-cadinan-3-ene-1,5-diol (2), (+)-(1R,5R,6R,7S,10R)-cadinan-3-ene-1,5-diol (3), (+)-(1R,5S,6R,7S,10R)-cadinan-4(11)-ene-1,5-diol (4), (+)-(1R,5R,6R,7R,10R)-cadinan-4(11)-ene-1,5,12-triol (5), (-)-(1R,4R,5S,6R,7S, 10R)-cadinan-1,4,5-triol (6), and (-)-(1R,6R,7S,10R)-11-oxocadinan-4-en-1-ol (7), together with nine known compounds were isolated from the brown alga Dictyopteris divaricata. The structures of the new natural products, as well as their absolute configuration, were established by means of spectroscopic data including IR, HRMS, 1D and 2D NMR, single-crystal X-ray diffraction, and CD. All compounds were inactive against several human cancer cell lines including lung adenocarcinoma (A549), stomach cancer (BGC-823), breast cancer (MCF-7), hepatoma (Bel7402), and colon cancer (HCT-8) cell lines. 相似文献
8.
Abdel-Halim OB Morikawa T Ando S Matsuda H Yoshikawa M 《Journal of natural products》2004,67(7):1119-1124
The 80% aqueous methanolic extract from the bulbs of Crinum yemense showed a potent inhibitory effect on nitric oxide production in lipopolysaccharide-activated macrophages. Three new crinine-type alkaloids, yemenines A (1), B (2), and C (3), were isolated from the herbal extract together with six known alkaloids. The absolute configurations of 1-3 were determined on the basis of chemical and physicochemical evidence. The effects of the isolated alkaloids on nitric oxide production in lipopolysaccharide-activated macrophages were examined, and several alkaloids, e.g. 1, (+)-bulbispermine (6), (+)-crinamine (7), (+)-6-hydroxycrinamine (8), and (-)-lycorine (9), showed inhibitory effects on nitric oxide production and induction of inducible nitric oxide synthase. 相似文献
9.
Minor sesquiterpenes with new carbon skeletons from the brown alga Dictyopteris divaricata 总被引:1,自引:0,他引:1
Song F Xu X Li S Wang S Zhao J Yang Y Fan X Shi J He L 《Journal of natural products》2006,69(9):1261-1266
Five minor sesquiterpenes (1-5) with two novel carbon skeletons, together with a minor new oplopane sesquiterpene (6), have been isolated from the brown alga Dictyopteris divaricata. By means of spectroscopic data including IR, HRMS, 1D and 2D NMR, and CD, their structures including absolute configurations were assigned as (+)-(1R,5S,6S,9R)-3-acetyl-1-hydroxy-6-isopropyl-9-methylbicyclo[4.3.0]non-3-ene (1), (+)-(1R,3S,4S,5R,6S,9R)-3-acetyl-1,4-dihydroxy-6-isopropyl-9-methylbicyclo[4.3.0]nonane (2), (+)-(1R,3R,4R,5R,6S,9R)-3-acetyl-1,4-dihydroxy-6-isopropyl-9-methylbicyclo[4.3.0]nonane (3), (+)-(1S,2R,6S,9R)-1-hydroxy-2-(1-hydroxyethyl)-6-isopropyl-9-methylbicyclo[4.3.0]non-4-en-3-one (4), (-)-(5S,6R,9S)-2-acetyl-5-hydroxy-6-isopropyl-9-methylbicyclo[4.3.0]non-1-en-3-one (5), and (-)-(1S,6S,9R)-4-acetyl-1-hydroxy-6-isopropyl-9-methylbicyclo[4.3.0]non-4-en-3-one (6). Biogenetically, the carbon skeletons of 1-6 may be derived from the co-occurring cadinane skeleton by different ring contraction rearrangements. Compounds 1-6 were inactive (IC(50) > 10 mug/mL) against several human cancer cell lines. 相似文献
10.
Widelski J Melliou E Fokialakis N Magiatis P Glowniak K Chinou I 《Journal of natural products》2005,68(11):1637-1641
Eight new coumarins were isolated from the fruits of Seseli devenyense Simonkai. Their structures were established from NMR and mass data and their absolute configurations from chemical degradation correlation reactions. The new structures are the decanoic and dodecanoic esters of (+)-lomatin (3, 4), the decanoates of (+)-cis-khellactone at positions 4' (5) and 3' (6) as well as the 2'S epimer of 8-(2,3-dihydroxy-3-methylbutyl)-7-hydroxychromen-2-one (7) named devenyol, its two O-monoglucosides at positions 3' and 7 named devenyosides A (8) and B (9), and the corresponding 3'- and 7-O-diglucoside named devenyoside C (10). This plant is an interesting example of stereochemical diversity based on biodiversity given that other members of the Apiaceae family produce exclusively the 2'R epimers of compounds 7-9. 相似文献
11.
A new meroditerpene, (+)-isojaspic acid (1), along with two known meroditerpenes, cacospongin D (2) and jaspaquinol (3), have been isolated from a marine sponge Cacospongia. Comprehensive taxonomic identification distinguished this Cacospongia apart from morphologically similar Psammocinia. The absolute stereochemistry of 1 was elucidated on the basis of extensive 1D and 2D NMR techniques and analysis of the optical rotation versus (+)-zonarol (8), (+)-isozonarol (9), (-)-dactylosponol (10), and (+)-hyatellaquinone (11). Furthermore, bioactivity evaluation showed that the meroditerpenes isolated significantly inhibited Staphylococcus epidermidis. 相似文献
12.
El Sayed KA Yousaf M Hamann MT Avery MA Kelly M Wipf P 《Journal of natural products》2002,65(11):1547-1553
Microbial and chemical transformation studies of the marine sesquiterpene phenols (S)-(+)-curcuphenol (1) and (S)-(+)-curcudiol (2), isolated from the Jamaican sponge Didiscus oxeata, were accomplished. Preparative-scale fermentation of 1 with Kluyveromyces marxianus var. lactis (ATCC 2628) has resulted in the isolation of six new metabolites: (S)-(+)-15-hydroxycurcuphenol (3), (S)-(+)-12-hydroxycurcuphenol (4), (S)-(+)-12,15-dihydroxycurcuphenol (5), (S)-(+)-15-hydroxycurcuphenol-12-al (6), (S)-(+)-12-carboxy-10,11-dihydrocurcuphenol (7), and (S)-(+)-12-hydroxy-10,11-dihydrocurcuphenol (8). Fourteen-days incubation of 1 with Aspergillus alliaceus (NRRL 315) afforded the new compounds (S)-(+)-10beta-hydroxycurcudiol (9), (S)-(+)-curcudiol-10-one (10), and (S)-(+)-4-[1-(2-hydroxy-4-methyl)phenyl)]pentanoic acid (11). Rhizopus arrhizus (ATCC 11145) and Rhodotorula glutinus (ATCC 15125) afforded (S)-curcuphenol-1alpha-D-glucopyranoside (12) and (S)-curcudiol-1alpha-D-glucopyranoside (13) when incubated for 6 and 8 days with 1 and 2, respectively. The absolute configuration of C(10) and C(11) of metabolites 7-9 was established by optical rotation computations. Reaction of 1 with NaNO(2) and HCl afforded (S)-(+)-4-nitrocurcuphenol (14) and (S)-(+)-2-nitrocurcuphenol (15) in a 2:1 ratio. Acylation of 1 and 2 with isonicotinoyl chloride afforded the expected esters (S)-(+)-curcuphenol-1-O-isonicotinate (16) and (S)-(+)-curcudiol-1-O-isonicotinate (17), respectively. Curcuphenol (1) shows potent antimicrobial activity against Candida albicans, Cryptococcus neoformans, methicillin-resistant Staphylococcus aureus, and S. aureus with MIC and MFC/MBC ranges of 7.5-25 and 12.5-50 microg/mL, respectively. Compounds 1 and 3 also display in vitro antimalarial activity against Palsmodium falciparium (D6 clone) with MIC values of 3600 and 3800 ng/mL, respectively (selectivity index >1.3). Both compounds were also active against P. falciparium (W2 clone) with MIC values of 1800 (S.I. >2.6) and 2900 (S.I. >1.6) ng/mL, respectively. Compound 14 shows anti-hepatitis B virus activity with an EC(50) of 61 microg/mL. 相似文献
13.
Two new 2,6-disubstituted piperidine alkaloids andrachcinine (1) and andrachcinidine (5) have been isolated from Andrachne aspera along with andrachamine and andrachcine (2). The absolute configurations of 1, 2, and 5 were established. (+)-Allosedridine and the new alkaloids (-)-8-epi-8-ethylnorlobelol I (4) and (-)-8-epihalosaline (7) were also identified as constituents of A. aspera. Structures were determined by MS and NMR techniques and by chemical conversions. 相似文献
14.
Two new bisbenzylisoquinoline alkaloids, (+)-coccuorbiculatine A (2) and (+)-10-hydroxyisotrilobine (3), two new amidic aporphines, a mixture of (+)-laurelliptinhexadecan-1-one (6) and (+)-laurelliptinoctadecan-1-one (7), and one new protoberberine (-)-4-methoxy-13,14-dihydrooxypalmatine (8) have been isolated from the stems of Taiwanese Cocculus orbiculatus. The structures were established on the basis of extensive analysis of spectroscopic data and by comparison with known related metabolites. Cytotoxicity of the isolated compounds was examined toward HepG2, Hep3B, MCF-7, and MDA-MB-231 cancer cell lines. Alkaloids 1 and (-)-sinococuline (9) showed significant inhibitory activity against the target cell lines. 相似文献
15.
Yokoyama R Huang JM Hosoda A Kino K Yang CS Fukuyama Y 《Journal of natural products》2003,66(6):799-803
A methanol extract of the pericarps of Illicium minwanense afforded seven new seco-prezizaane-type sesquiterpenes (2-8) and a new abietane-type diterpene (9), together with six previously known compounds (1 and 10-14). The structures of the new compounds, (1S)- and (1R)-minwanenone (2 and 3), 1alpha-hydroxy-6-deoxypseudoanisatin (4), (2S)-hydroxy-6-deoxypseudoanisatin (5), 3-oxopseudoanisatin (6), (3S,6R)-4,7-epoxy-6-deoxypseudoanisatin (7), 7-O-methylpseudomajucin (8), and (+)-8,11,13,15-abietatetraene (9), were elucidated by spectroscopic data analysis and chemical transformations. The absolute configurations of 1 and 5 were established by X-ray crystallographic analysis of their p-bromobenzoyl derivatives. 相似文献
16.
Chen M Gan L Lin S Wang X Li L Li Y Zhu C Wang Y Jiang B Jiang J Yang Y Shi J 《Journal of natural products》2012,75(6):1167-1176
Seventeen new alkaloids (1-17) and 14 known analogues have been isolated from an aqueous extract of the root of Isatis indigotica. The structures and absolute configurations of these compounds were determined by extensive spectroscopic data analysis, including 2D NMR, single-crystal X-ray crystallography using anomalous scattering of Cu Kα radiation, and electronic circular dichroism spectra calculations based on the quantum-mechanical time-dependent density functional theory. Compounds 1, 2, and 3 are the first examples of natural products with unique linkages between a molecule of 2-(4-methoxy-1H-indol-3-yl)acetonitrile and 2-(1H-indol-3-yl)acetonitrile, 2-(4-methoxy-1H-indol-3-yl)acetonitrile, and 4-hydroxyphenylethane, respectively. Compounds (-)-4 and (+)-4 represent the first natural products with the pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline skeleton. Some structural assignments for the new alkaloids suggest that the assignments made for certain previously reported alkaloids require revision. Compounds 1-3 and arvelexin (18) show antiviral activity against the influenza virus A/Hanfang/359/95 (H3N2), with IC(50) values of 3.70-12.35 μM, and 17 inhibits Coxsackie virus B3 replication with an IC(50) of 6.87 μM. 相似文献
17.
The roots of Bulbinella floribunda have been analyzed for the phenolic constituents, resulting in the isolation of five new phenylanthraquinone glycosides, named bulbinelonesides A-E (1-5), along with two known phenylanthraquinones, (+)-M-knipholone (6) and (+)-M-isoknipholone (7). The structures of the new compounds were determined on the basis of extensive spectroscopic analysis, including 2D NMR, and the results of enzymatic hydrolysis. Although the new compounds 3-5, whose absolute stereochemistry of the unsymmetric biaryl moiety was determined to be P by the CD spectrum, did not show apparent cytotoxicity against cultured HSC-2 tumor cells and HPC normal cells, the new compounds 1 and 2, as well as the known compounds 6 and 7, whose biaryl bond was assigned as M, exhibited a tumor-specific cytotoxicity against HSC-2 cells comparable to or slightly weaker than etoposide, used as a positive control. 相似文献
18.
Davis RA 《Journal of natural products》2005,68(5):769-772
Chemical investigations of the terrestrial microfungus Xylaria sp. have afforded the new natural product (-)-xylariamide A (1). The gross structure of 1 was determined by interpretation of 1D and 2D NMR, UV, IR, and MS data. Confirmation of the structure and the absolute stereochemistry of 1 were determined by the total synthesis of (+)-xylariamide A (2). Synthetic 2 was produced by N,O-bis(trimethylsilyl)acetamide-induced coupling of 3-chloro-L-tyrosine (3) with (E)-but-2-enedioic acid 2,5-dioxo-pyrrolidin-1-yl ester methyl ester (4). Optical rotation comparison of 1 with 2 indicated that the natural product (1) contained 3-chloro-D-tyrosine. Both enantiomers of xylariamide A were tested in a brine shrimp lethality assay, and only the natural product (1) showed toxicity. 相似文献
19.
Kim TH Ito H Hatano T Hasegawa T Akiba A Machiguchi T Yoshida T 《Journal of natural products》2005,68(12):1805-1808
Six new bisabolane-type (1-3) and santalane-type (4-6) sesquiterpenoids, together with (+)-alpha-nuciferol, (+)-citronellol, and geraniol, were isolated from the heartwood of Santalum album of Indian origin. Their structures, including two bisabolol diastereomers (1, 2), were established on the basis of spectroscopic data interpretation. 相似文献
20.
Song F Xu X Li S Wang S Zhao J Cao P Yang Y Fan X Shi J He L Lü Y 《Journal of natural products》2005,68(9):1309-1313
Three bisnorsesquiterpenes (1-3) with novel carbon skeletons and a norsesquiterpene (4) have been isolated from the brown alga Dictyopteris divaricata. By means of spectroscopic data including IR, HRMS, 1D and 2D NMR techniques, single-crystal X-ray diffraction, and CD, their structures including absolute configurations were proposed as (+)-(1R,6S,9R)-1-hydroxyl-6-isopropyl-9-methylbicyclo[4.3.0]non-4-en-3-one (1), (-)-(1S,6S,9R)-1-hydroxyl-6-isopropyl-9-methylbicyclo[4.3.0] non-4-en-3-one (2), (+)-(5S,6R,9S)-5-hydroxyl-6-isopropyl-9-methylbicyclo[4.3.0]non-1-en-3-one (3), and (-)-(1R,7S,10R)-1-hydroxy-11-norcadinan-5-en-4-one (4). Biogenetically, the carbon skeleton of 1-3 may be derived from the co-occurring cadinane skeleton by ring contraction and loss of two carbon units, and compound 4 from the oxidation of cadinane derivatives. Compounds 1-4 were inactive (IC50 > 10 microg/mL) against several human cancer cell lines including lung adenocarcinoma (A549), stomach cancer (BGC-823), breast cancer (MCF-7), hepatoma (Bel7402), and colon cancer (HCT-8) cell lines. 相似文献