Search results for "DISCOVERY"
showing 10 items of 4119 documents
Bisbenzyltetrahydroisoquinolines, a New Class of Inhibitors of the Mitochondrial Respiratory Chain Complex I
2004
Four bisbenzyltetrahydroisoquinoline alkaloids (-)-medelline, (+)-antioquine, (+)-aromoline, and (+)-obamegine were isolated from the fruits of Xylopia columbiana. These compounds, the previously isolated alkaloids (+)-thaligrisine and (+)-isotetrandrine, as well as their O-acetylated derivatives were assayed on submitochondrial particles from beef heart as inhibitors of the mammalian respiratory chain. The results revealed that these alkaloids act as selective inhibitors of mitochondrial complex I in a 0.15 - 4.71 microM range. O-Acetylation, which increases their lipophilicity, considerably increased the inhibitory potency.
Cytotoxic Isomalabaricane Triterpenes from the Marine Sponge Rhabdastrella globostellata
2006
Fourteen isomalabaricane triterpenes were isolated from the marine sponge Rhabdastrella globostellata. In addition to the known compounds globostellatic acids A (1) and D (4) and stelliferin riboside (13), 11 of the compounds were new natural products, which included globostelletin (3), eight new globostellatic acid congeners, F to M (2, 5-11), and two new stelliferin ribosides (12 and 14). The isolated compounds were tested against three different cancer cell lines, L5178Y (mouse lymphoma), HeLa (human cervix carcinoma), and PC-12 (rat pheochromocytoma). The isomalabaricane derivatives were found to be selectively active toward the mouse lymphoma cell line L5178Y. The structures were deter…
Three New Triterpene Saponins from Two Species of Carpolobia
2002
Three new acetylated triterpene saponins 1-3 were isolated from the roots of Carpolobia alba and C. lutea. Their structures were established mainly by 2D NMR techniques as 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-galactopyranosyl-(1-->4)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl)-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-galactopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->3)]-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl)-beta-D-fucopyranosyl ester, and 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-xylopyranosyl-(1-->4)-[beta-D-apiofuranosyl…
Glandulosides A-D, triterpene saponins from Acanthophyllum glandulosum.
2004
Four novel triterpenoid saponins, glandulosides A (1), B (2), C (3), and D (4), together with two known saponins (5 and 6) have been isolated from the roots of Acanthophyllum glandulosum. Their structures were elucidated using a combination of homo- and heteronuclear 2D NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FABMS. The new compounds were characterized as 23-O-beta-D-galactopyranosylgypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[beta-d-galactopyranosyl-(1-->6)]-beta-D-galactopyranoside (1), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-l-rhamn…
Antiproliferative Oleanane Saponins from Meryta denhamii
2008
Eight new oleanane saponins (1- 8) together with four know saponins (9-12) were isolated from the aerial parts of Meryta denhamii. Their structures were elucidated by 1D and 2D NMR experiments including 1D TOCSY, DQF-COSY, ROESY, HSQC, and HMBC spectroscopy, as well as ESIMS analysis. The antiproliferative activity of all compounds was evaluated using three murine and human cancer cell lines: J774.A1, HEK-293, and WEHI-164.
Two Triterpene Saponins from Achyranthes bidentata.
2001
Bidentatoside II (1) and chikusetsusaponin V methyl ester (2) are two further triterpene saponins isolated from the roots of Achyranthes bidentata. Chemical and homo and heteronuclear two-dimensional (2D) NMR techniques have led to the structural elucidation of 1 which is a new seco-glycoside of oleanolic acid and the full 1H- and 13C-NMR assignments of 2. These compounds did not show any potentiation of the in vitro cytotoxicity of cisplatin in the HT 29 human colon cancer cell line.
Dihydroisocoumarins, Naphthalenes, and Further Polyketides from Aloe vera and A. plicatilis: Isolation, Identification and Their 5-LOX/COX-1 Inhibiti…
2021
The present study aims at the isolation and identification of diverse phenolic polyketides from Aloe vera (L.) Burm.f. and Aloe plicatilis (L.) Miller and includes their 5-LOX/COX-1 inhibiting potency. After initial Sephadex-LH20 gel filtration and combined silica gel 60- and RP18-CC, three dihydroisocoumarins (nonaketides), four 5-methyl-8-C-glucosylchromones (heptaketides) from A. vera, and two hexaketide-naphthalenes from A. plicatilis have been isolated by means of HSCCC. The structures of all polyketides were elucidated by ESI-MS and 2D 1H/13C-NMR (HMQC, HMBC) techniques. The analytical/preparative separation of 3R-feralolide, 3′-O-β-d-glucopyranosyl- and the new 6-O-β-d-glucopyranosyl…
Water-soluble isoindolo[2,1-a]quinoxalin-6-imines: In vitro antiproliferative activity and molecular mechanism(s) of action
2015
Abstract Water-soluble isoindoloquinoxalin (IIQ) imines and the corresponding acetates were conveniently prepared from the key intermediates 2-(2′-aminophenyl)-2H-isoindole-1-carbonitriles obtained by a Strecker reaction between substituted 1,2-dicarbaldehydes and 1,2-phenylenediamines. Both series were screened by the National Cancer Institute (Bethesda, MD) and showed potent antiproliferative activity against a panel of 60 human tumor cell lines. Several of the novel compounds showed GI50 values at a nanomolar level on the majority of the tested cell lines. Among IIQ derivatives, methoxy substituents at positions 3 and 8 or/and 9 were especially effective in impairing cell cycle progressi…
Cytotoxic activity of some natural and syntetic sesquiterpene lactones
2006
Several natural and synthetic sesquiterpene lactones with different skeletons were tested and found to be active against nine cancer cell lines. Elemane (4), heliangolane (5) and their hydroxy analogues 9 and 10, all containing an α,β-unsaturated aldehyde substituent, were the most potent compounds.
Dual Substituent Parameter Modeling of Theoretical, NMR and IR Spectral Data of 5-Substituted Indole-2,3-diones
2002
Correlations of AM1 and PM3 theoretical data, 13C-NMR substituent chemical shifts (13C-SCS) and IR carbonyl group wave numbers [ν(C3â•ÂO)] were studied using dual substituent parameter (DSP) models for 5-substituted indole-2,3-diones. For the C7 atom a reverse substituent effect attributed to extended À-polarization was observed. On the other hand, the DSP approaches for the C3 atom showed normal substituent effects with some contribution of reverse effect supported strongly by 13C-SCS correlations. In the ν(C3â•ÂO) and p(C3â•ÂO) DSP correlations the field effect contribution predominates over the resonance effect, which justifies the using of earlier suggested vibrational cou…