共查询到20条相似文献,搜索用时 15 毫秒
1.
Nicotra VE Ramacciotti NS Gil RR Oberti JC Feresin GE Guerrero CA Baggio RF Garland MT Burton G 《Journal of natural products》2006,69(5):783-789
Twelve new withanolides were isolated from the aerial part of Jaborosa rotacea: five had a spiranoid delta-lactone (1-5); one contained a 26,12-delta-lactone and a C-12-C-23 bond (6); five corresponded to trechonolide-type withanolides with configuration at C-23 opposite of those previously isolated (7, 8, 10-12); two of these have an additional oxido-bridge between C-21 and C-24; finally a withanolide with a hemiketal ring formed between a 21-hydroxyl and a 12-ketone (13) and the closely related jaborosalactone R were also isolated. New compounds were fully characterized by a combination of spectroscopic methods (1D and 2D NMR and MS). The structures of the spiranoid withanolide and of the epimer of trechonolide A were confirmed by X-ray diffraction studies. Compounds 4, 5, 6, and 8 showed selective phytotoxicity toward monocotyledoneous and dicotyledoneous species. 相似文献
2.
Cirigliano AM Veleiro AS Misico RI Tettamanzi MC Oberti JC Burton G 《Journal of natural products》2007,70(10):1644-1646
Six new trechonolide type withanolides (compounds 1- 6), together with trechonolide A, jaborotetrol, and 12- O-methyl jaborosotetrol, were isolated from the aerial parts of Jaborosa laciniata. The structures were elucidated on the basis of spectroscopic methods (1D and 2D NMR, MS). 相似文献
3.
Two new withanolides were isolated and characterized from the aerial parts of Jaborosa kurtzii, namely, jaborosalactone 43 (1), with a spiranoid delta-lactone at C-22, and jaborosalactone 44 (2), a 12-oxowithanolide, which may function as a biosynthetic precursor to 1. These new compounds were fully characterized by a combination of spectroscopic methods. Compound 1 showed selective phytotoxicity toward a dicotyledon species, Lactuca sativa (lettuce). 相似文献
4.
Six new withanolides (1-6) were isolated from the aerial parts of Jaborosa bergii plants and characterized by spectroscopic methods (1D and 2D NMR, MS). Five of the new compounds presented a novel norbornane-type structure in ring D of the steroid nucleus (1-5), resulting from a carbon-carbon bond between C-15 and C-21. The sixth withanolide isolated was the 5alpha-chloro-6beta-hydroxy analogue (6) of 2,3-dehydrojaborosalactol M (7), previously isolated from this plant. Compound 1 showed selective phytotoxicity toward monocotiledoneous and dicotiledoneous species. 相似文献
5.
Hsieh PW Huang ZY Chen JH Chang FR Wu CC Yang YL Chiang MY Yen MH Chen SL Yen HF Lübken T Hung WC Wu YC 《Journal of natural products》2007,70(5):747-753
Fifteen new withanolides (1-8, 11-17) and two known withanolides, withanolide D (9) and 17alpha-hydroxywithanolide D (10), were isolated from the stems, roots, and leaves of Tubocapsicum anomalum using bioassay-directed fractionation. The structures were determined by spectroscopic and chemical methods, and the absolute configurations were established by CD analysis and by the Mosher ester method. The structure of 1 and 3 were further confirmed by X-ray crystallographic analysis. Compounds 1, 4-6, 8-10, and 13 showed significant cytotoxic activity against Hep G2, Hep 3B, A-549, MDA-MB-231, MCF-7, and MRC-5 cell lines. 相似文献
6.
Pérez-Castorena AL Oropeza RF Vazquez AR Martínez M Maldonado E 《Journal of natural products》2006,69(7):1029-1033
Aerial parts of Physalis coztomatl afforded a new labdane diterpene, physacoztomatin (1), and five new withanolides, physacoztolides A-E (5-9). Six known compounds were also isolated. The structures of the new compounds were established after analyses of their spectroscopic data and by means of chemical transformations. X-ray diffraction analyses of 15-dehydrophysacoztomatin (2) and 5 confirmed the structures of 1 and 5. Labd-13(E)-ene-8alpha,15-diol (4) and physacoztomatin (1) represent the first labdane diterpenes isolated from the genus Physalis. 相似文献
7.
Chemical investigation of a methanol extract of the flowers of Datura metel has led to the isolation of 10 new withanolides, withametelins I-P (1-8), 1,10-seco-withametelin B (9), and 12beta-hydroxy-1,10-seco-withametelin B (10), together with seven known withanolides. The structures of 1-10 were elucidated by means of spectroscopic methods, and the absolute stereochemistry of 1 was confirmed by single-crystal X-ray analysis. Compounds 1, 3, 4, and 6 exhibited cytotoxic activities against A549 (lung), BGC-823 (gastric), and K562 (leukemia) cancer cell lines, with IC50 values ranging from 0.05 to 3.5 microM. 相似文献
8.
J A Bravo B M Sauvain A Gimenez T E Balanza L Serani O Laprévote G Massiot C Lavaud 《Journal of natural products》2001,64(6):720-725
Two new withanolide glycosides, (20R,22R)-O-(3)-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl-1 alpha,12 beta-diacetoxy-20-hydroxywitha-5,24-dienolide (3) and (20R,22R)-O-(3)-beta-D-xylopyranosyl(1-->3)-[beta-D-xylopyranosyl(1-->4)]-beta-D-glucopyranosyl-1 alpha-acetoxy-12 beta,20-dihydroxywitha-5,24-dienolide (4), were isolated from the leaves and root of Dunalia brachyacantha. Their aglycones, (20R,22R)-1 alpha,12 beta-diacetoxy-3 beta,20-dihydroxywitha-5,24-dienolide (or 1 alpha,12 beta-diacetyldunawithagenine) and (20R,22R)-1 alpha-acetoxy-3 beta,12 beta,20-trihydroxywitha-5,24-dienolide (or 1 alpha-acetyl-12 beta-hydroxydunawithagenine), are novel. The known 18-acetoxywithanolide D (1) and 18-acetoxy-5,6-deoxy-5-withenolide D (2) were also isolated from the leaves. These last two compounds were shown to be responsible for the trypanocidal, leishmanicidal, and bactericidal activities manifested by the crude ethanolic extract. The structures were deduced from spectroscopic data and on the basis of chemical evidence. 相似文献
9.
Mareggiani G Picollo MI Zerba E Burton G Tettamanzi MC Benedetti-Doctorovich MO Veleiro AS 《Journal of natural products》2000,63(8):1113-1116
The antifeedant effect of several salpichrolides on larvae of Musca domestica was investigated. Three naturally occurring compounds, salpichrolide A (1), salpichrolide C (2), and salpichrolide G (3), previously isolated from Salpichroa origanifolia, and two known (4, 6) and three new (5, 7, 8) synthetic analogues were tested. The maximal effect on development was observed for salpichrolide A (1), while salpichrolide G (3) was the most toxic. The content of the salpichrolides in S. origanifolia was monitored by HPLC during plant development, reaching a maximum during summer. 相似文献
10.
Misico RI Song LL Veleiro AS Cirigliano AM Tettamanzi MC Burton G Bonetto GM Nicotra VE Silva GL Gil RR Oberti JC Kinghorn AD Pezzuto JM 《Journal of natural products》2002,65(5):677-680
Thirty-seven naturally occurring withanolides (1-37), previously isolated in our laboratories, were evaluated for their potential to induce quinone reductase with cultured murine hepatoma cells (Hepa 1c1c7). Spiranoid (29, 32) and 18-functionalized withanolides (2-5, 7-9, 24) were found to be potent inducers of the enzyme, while 5alpha-substituted derivatives exhibited weak activity. Preliminary studies were performed with compound 29 to evaluate enzyme-inducing capacity in multiple organ sites of BALB/c mice. Significant induction was observed in liver and colon, but not in lung, stomach, or mammary gland. 相似文献
11.
Chao CH Chou KJ Wen ZH Wang GH Wu YC Dai CF Sheu JH 《Journal of natural products》2011,74(5):1132-1141
Six new withanolides, paraminabeolides A-F (1-6), along with five known compounds, minabeolides-1, -2, -4, -5, and -8 (7-11), were isolated from a Formosan soft coral, Paraminabea acronocephala. The structures of these compounds were elucidated by extensive spectroscopic analysis and chemical transformation. The absolute configuration of 4 was determined by the application of Mosher's method. Compounds 1 and 7 were cytotoxic toward Hep G2 cancer cells. Compounds 1-4 and 7-10 were found to significantly inhibit the accumulation of the pro-inflammatory iNOS protein. Compounds 7-10 also could effectively reduce the expression of COX-2 protein. 相似文献
12.
Seven new withanolides (1-7) were isolated from the aerial parts of Jaborosa caulescens var. caulescens and Jaborosa caulescens var. bipinnatifida. Three of the new compounds are related to jaborosalactones R, S, and T with a delta-lactone side chain and a hemiketal (or ketal) ring formed between a 21-hydroxyl and a 12-ketone (1-3). Compounds 4-7 are trechonolide-type withanolides with a gamma-lactone side chain and a hemiketal (or ketal) ring formed between a 22-hydroxyl and a 12-ketone. Compounds 4 and 5 also contain a hydroxyl group at C-21. Compounds 1, 2, and 7 showed selective phytotoxicity toward monocotyledonous and dicotyledonous species. 相似文献
13.
Damu AG Kuo PC Su CR Kuo TH Chen TH Bastow KF Lee KH Wu TS 《Journal of natural products》2007,70(7):1146-1152
Phytochemical investigation of Physalis angulata was initiated following primary biological screening. Fractionation of CHCl3 and n-BuOH solubles of the MeOH extract from the whole plant was guided by in vitro cytotoxic activity assay using cultured HONE-1 and NUGC cells and led to the isolation of seven new withanolides, withangulatins B-H (1-7), and a new minor physalin, physalin W (8), along with 14 known compounds, including physaprun A, withaphysanolide, dihydrowithanolide E, physanolide A, withaphysalin A, and physalins B, D, F, G, I, J, T, U, and V. New compounds (1-8) were fully characterized by a combination of spectroscopic methods (1D and 2D NMR and MS) and the relative stereochemical assignments based on NOESY correlations and analysis of coupling constants. Biological evaluation of these compounds against a panel of human cancer cell lines showed broad cytotoxic activity. Withangulatin B (1) and physalins D (10) and F (11) displayed potent cytotoxic activity against a panel of human cancer cell lines with EC50 values ranging from 0.2 to 1.6 microg/mL. Structure-activity relationship analysis indicated that withanolides and physalins with 4beta-hydroxy-2-en-1-one and 5beta,6beta-epoxy moieties are potential cytotoxic agents. 相似文献
14.
Naturally occurring beta-triketones, isoleptospermone [3, 5-hydroxy-4-(2-methyl-1-oxopentyl)-2,2,6, 6-tetramethyl-4-cyclohexene-1,3-dione) from Leptospermum scoparium] and papuanone [6, 5-hydroxy-4-(1-oxohexyl)-2,2,6, 6-tetramethyl-4-cyclohexene-1,3-dione from Corymbia dallachiana], have been synthesized. Full spectral data are reported for the first time. The 13C NMR spectra of 3, 6, and the other triketones flavesone (2), leptospermone (4), and grandiflorone (5) found in Myrtaceous plants are fully assigned. 相似文献
15.
Abdel-Kader MS Bahler BD Malone S Werkhoven MC Wisse JH Neddermann KM Bursuker I Kingston DG 《Journal of natural products》2000,63(11):1461-1464
Bioassay-guided fractionation of the MeOH extract of Swartzia schomburgkii using the engineered yeast strains 1138, 1140, and 1353 as the bioassay tool resulted in the isolation of five active (2, 4-7) and three inactive (1, 3, 8) saponins. Saponins 4 and 6 are previously unreported. The structures of all of the saponins were established based on 1D and 2D NMR spectral analysis, on acid and alkaline hydrolysis followed by TLC and GC-MS, and by comparison with literature data for known compounds. Three of the isolated compounds (4-6) showed weak cytotoxicity against the M-109 cell line. 相似文献
16.
Chaturvedula VS Norris A Miller JS Ratovoson F Andriantsiferana R Rasamison VE Kingston DG 《Journal of natural products》2006,69(2):287-289
Bioassay-directed fractionation of ethanol extracts of the roots and leaves of the plant Cassipourea madagascariensis resulted in the isolation of the two new terpenoids cassipourol (1) and cassipouryl acetate (2) in addition to the three known compounds, 3beta,30-dihydroxylup-20(29)-ene (3), 30-hydroxylup-20(29)-en-3-one (4), and combretol (5). The structures of the two new compounds were established on the basis of 1D and 2D NMR spectroscopic data and chemical conversion. All the isolated compounds were tested against the A2780 human ovarian cancer cell line; the two diterpenes (1 and 2) showed moderate cytotoxic activity, while the three known compounds (3-5) were weakly active. 相似文献
17.
Three colossolactones (colossolactone E, colossolactone B and 23-hydroxycolossolactone E) were isolated and characterized from an n-hexane:dichloromethane (2:7) extract of Ganoderma colossum using chromatographic techniques. The antimicrobial activity of the three compounds was then tested against Gram-positive and Gram-negative bacteria. The activity was evaluated by the thin-layer chromatography agar overlay method. The results showed that colossolactone E and 23-hydroxycolossolactone E were active against Bacillus subtilis and Pseudomonas syringae. Colossolactone B was not active against the bacteria. Their structures were elucidated by spectroscopic methods. Potency of the compounds against bacteria tested supports the use of this mushroom in therapeutic medicine. 相似文献
18.
Seo Y Hoch J Abdel-Kader M Malone S Derveld I Adams H Werkhoven MC Wisse JH Mamber SW Dalton JM Kingston DG 《Journal of natural products》2002,65(2):170-174
Bioassay-guided fractionation of the MeOH extract of Acacia tenuifolia using the engineered yeast strains 1138, 1140, 1353, and Sc7 as the bioassay tool resulted in the isolation of the three new saponins 3, 5, and 6 and the three known saponins 1, 2, and 4. The structures of the new compounds were established on the basis of HRMS, 1D and 2D NMR spectral data on the intact saponins, and GC-MS analyses of the sugars. Compounds 1,2 and 5,6 showed cytotoxicity against mammalian cell lines. 相似文献
19.
Cao S Schilling JK Miller JS Andriantsiferana R Rasamison VE Kingston DG 《Journal of natural products》2004,67(3):454-456
Bioassay-guided fractionation of methanolic extracts of Mundulea chapelieri resulted in the isolation of two new flavonoids, isomundulinol (1) and 3-deoxy-MS-II (2), in addition to the eight known flavonoids 8-(3,3-dimethylallyl)-5,7-dimethoxyflavanone, MS-II, mundulinol, mundulone, munetone, rotenolone, rotenone, and tephrosin, and one known sesquiterpenoid, 8alpha-acetoxyelemol. The structures of the new flavonoids 1 and 2 were determined by 1D and 2D NMR experiments. All the isolated compounds were tested for cytotoxicity against the A2780 human ovarian cancer cell line; rotenolone and rotenone were the most potent compounds isolated, with IC(50) values of 0.5 and 0.7 microg/mL, respectively. 相似文献
20.
Cytotoxic sesquiterpene lactones from Vernonia pachyclada from the Madagascar rainforest 总被引:1,自引:0,他引:1
Williams RB Norris A Slebodnick C Merola J Miller JS Andriantsiferana R Rasamison VE Kingston DG 《Journal of natural products》2005,68(9):1371-1374
Bioassay-guided fractionation of the cytotoxic leaf extract of Vernonia pachyclada Baker led to the isolation of three new sesquiterpene lactones, designated glaucolides K-M (1-3). The structures of the new compounds were determined using 1D and 2D NMR spectroscopy, and the structure and stereochemistry of 1 were confirmed by single-crystal X-ray diffraction. Compound 3 showed moderate activity in the A2780 human ovarian cancer cell line, with an IC50 of 3.3 microM. 相似文献