Displaying publications 1 - 20 of 100 in total

  1. Saad JM, Soepadamo E, Fang XP, McLaughlin JL, Fanwick PE
    J Nat Prod, 1991 11 1;54(6):1681-3.
    PMID: 1812217
    The known lignan (-)-grandisin [1] has been isolated from Cryptocarya crassinervia by using the brine shrimp lethality test to direct the isolation; its structure and relative stereochemistry have been determined by ir, 1H nmr, ms, and X-ray crystallography as an all-trans alpha, alpha'-diaryl-beta, beta'-dimethyltetrahydrofuran. Compound 1 is not significantly cytotoxic in our panel of human tumor cells.
  2. Fu X, Sévenet T, Remy F, Païs M, Hamid A, Hadi A, et al.
    J Nat Prod, 1993 Jul;56(7):1153-63.
    PMID: 8377019
    Four complex flavanones, kurziflavolactones A [2], B [3], C [4], and D [5] and a complex chalcone 6 with an unprecedented carbon side chain on the flavanone or chalcone A ring have been isolated from a Malaysian plant, Cryptocarya kurzii (Lauraceae). Their structures were determined by extensive spectroscopic analysis, especially 2D nmr experiments. Compounds 3 and 6 showed slight cytotoxicity against KB cells, with IC50 values of 4 and 15 micrograms/ml, respectively. A biosynthetic pathway for the formation of these compounds is suggested.
  3. Lichius JJ, Thoison O, Montagnac A, Païs M, Guéritte-Voegelein F, Sévenet T, et al.
    J Nat Prod, 1994 Jul;57(7):1012-6.
    PMID: 7964782
    Bioassay-guided fractionation of the extracts of Zieridium pseudobtusifolium and Acronychia porteri led to the isolation of 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone [1], which showed activity against (KB) human nasopharyngeal carcinoma cells (IC50 0.04 micrograms/ml) and inhibited tubulin assembly into microtubules (IC50 12 microM). Two other known flavonols, digicitrin [2] and 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone [5], were also isolated together with three new ones, 3-O-demethyldigicitrin [3], 3,5,3'-trihydroxy-6,7,8,4'-tetramethoxyflavone [4], and 3,5-dihydroxy-6,7,8,3',4'-pentamethoxyflavone [6]. All of these flavonols showed cytotoxic activity against KB cells.
  4. Alias Y, Awang K, Hadi AH, Thoison O, Sévenet T, Païs M
    J Nat Prod, 1995 Aug;58(8):1160-6.
    PMID: 7595585
    Bioassay-guided fractionation of an ethyl acetate extract of Fissistigma lanuginosum led to the isolation of the known chalcone pedicin [1], which inhibited tubulin assembly into microtubules (IC50 value of 300 microM). From the same EtOAc fraction, two new condensed chalcones, fissistin [2] and isofissistin [3], which showed cytotoxicity against KB cells, were also obtained, together with the inactive dihydropedicin [4] and 6,7-dimethoxy-5,8-dihydroxyflavone [5]. In addition, the aminoquinones 6, 8, and 9 were isolated from the alkaloid extract. These compounds were artifacts, prepared by treatment of 1, 4, and 2, respectively, with NH4OH. The structures of the new compounds were elucidated by spectral methods, especially 2D nmr.
  5. Mok SL, Yoganathan K, Lim TM, Kam TS
    J Nat Prod, 1998 Mar;61(3):328-32.
    PMID: 9544563
    Intravenous injection of the aspidofractinine alkaloid, kopsingine (1, 0.2-10.0 mg/kg) from Kopsia teoi, produced dose-related decreases in the mean arterial blood pressure and heart rate in anesthetized spontaneously hypertensive rats, which were similar to those seen in normotensive controls. Minor modifications in the molecular structure of kopsingine, as in kopsaporine (2, the 12-demethoxy derivative of kopsingine) and 14,15-dihydrokopsingine (4), did not significantly alter the hypotensive responses, whereas a more drastic change in the structure, as in the heptacyclic kopsidine A (3) and the 3-to-17 oxo-bridged compound 5, resulted in an increase in blood pressure. The antihypertensive effects of kopsingine (1) and its congeners (2 and 4) along with the pressor effects produced by the heptacyclic oxo-bridged compounds (5 and 3) could be ascribed to central as well as peripheral actions.
  6. Kam TS, Sim KM, Koyano T, Toyoshima M, Hayashi M, Komiyama K
    J Nat Prod, 1998 Nov;61(11):1332-6.
    PMID: 9834146
    The EtOH extract of the leaves of Holarrhena curtisii yielded five new steroidal alkaloids: 17-epi-holacurtine (3), 17-epi-N-demethylholacurtine (4), holacurtinol (5), 3alpha-amino-14beta-hydroxypregnan-20-one (7), and 15alpha-hydroxyholamine (8), in addition to the known compounds, holacurtine (1), N-demethylholacurtine (2), and holamine (6). All eight compounds showed significant cytotoxic and leishmanicidal activities.
  7. Mohamad K, Martin MT, Najdar H, Gaspard C, Sévenet T, Awang K, et al.
    J Nat Prod, 1999 Jun;62(6):868-72.
    PMID: 10395505
    Nine 3,4-secoapotirucallanes, argentinic acids A-I, were isolated from the bark of Aglaia argentea and transformed to their methyl esters 1-9. The structures were determined by spectral and chemical means. Compounds 1-8 showed moderate cytotoxic activity against KB cells (IC50 1.0-3.5 microg/mL).
  8. Permana D, Lajis NH, Othman AG, Ali AM, Aimi N, Kitajima M, et al.
    J Nat Prod, 1999 Oct;62(10):1430-1.
    PMID: 10543909
    A new anthraquinone, 2-hydroxymethyl-10-hydroxy-1,4-anthraquinone (1), was isolated from Hedyotis herbacea along with three other known derivatives: 1,4-dihydroxy-2-hydroxymethylanthraquinone (2); 2, 3-dimethoxy-9-hydroxy-1,4-anthraquinone; and 1,4-dihydroxy-2, 3-dimethoxyanthraquinone. The structure of 1 was determined based on analysis of its spectroscopic data.
  9. Yoshikawa K, Tao S, Arihara S
    J Nat Prod, 2000 Apr;63(4):540-2.
    PMID: 10785436
    The stem of Stephanotis floribunda afforded a new cyclic pentapeptide stephanotic acid (1), possessing a novel 6-(leucin-3'-yl) tryptophan skeleton. The structure of 1 was assigned on the basis of extensive NMR experiments and a chemical reaction and shown to be closely related to the bicyclic octapeptide moroidin (3), a toxin from Laportea moroides.
  10. Xu YJ, Wu XH, Tan BK, Lai YH, Vittal JJ, Imiyabir Z, et al.
    J Nat Prod, 2000 Apr;63(4):473-6.
    PMID: 10785416
    Leaf extracts of the Malaysian plant Aglaia laxiflora provided two cytotoxic compounds, a new rocaglaol rhamnoside (1), a known rocaglaol (2), new (but inactive) flavonol-cinnamaminopyrrolidine adducts (3-6), and their probable biosynthetic precursors (7 and trimethoxyflavonol). All structures were elucidated primarily by 2D NMR spectroscopy. The structure and stereochemistry of aglaxiflorin A (3) were confirmed by single-crystal X-ray crystallography.
  11. Roux D, Hadi HA, Thoret S, Guénard D, Thoison O, Païs M, et al.
    J Nat Prod, 2000 Aug;63(8):1070-6.
    PMID: 10978200
    Microtubule disassembly inhibitory properties have been established for the known polyisoprenylated benzophenones xanthochymol (1a) and guttiferone E (1b). The compounds were isolated from the fruits of Garcinia pyrifera collected in Malaysia. A structure-activity relationship study, including natural and semisynthetic derivatives, delineated some structural features necessary for the interaction with tubulin within this compound class.
  12. Xu J, Harrison LJ, Vittal JJ, Xu YJ, Goh SH
    J Nat Prod, 2000 Aug;63(8):1062-5.
    PMID: 10978198
    Leaf extracts of Callicarpa pentandra provided four new clerodane-type diterpenoids (1-4), of which 1, 2, and 4 have ring-A-contracted structures. Their structures and stereochemistry were established by spectral data interpretation, and for 3 also by single-crystal X-ray diffraction.
  13. Xu YJ, Chiang PY, Lai YH, Vittal JJ, Wu XH, Tan BK, et al.
    J Nat Prod, 2000 Oct;63(10):1361-3.
    PMID: 11076552
    Leaf extracts of Garcinia parvifolia provided relatively high yields of four novel, cytotoxic prenylated depsidones. The structures were determined mainly by detailed NMR spectral analysis and X-ray crystallography.
  14. Suzuki M, Daitoh M, Vairappan CS, Abe T, Masuda M
    J Nat Prod, 2001 May;64(5):597-602.
    PMID: 11374951
    In connection with our chemotaxonomic studies of Malaysian species of the red algal genus Laurencia, the chemical composition of Laurencia pannosa Zanardini was examined. Two halogenated sesquiterpenoids, named pannosanol (1) and pannosane (2), have been isolated along with a halogenated C15-acetogenin, (3Z)-chlorofucin (3). The structures of these compounds were determined from their spectroscopic data (IR, 1H NMR, 13C NMR, 2D NMR, and MS). Pannosanol and pannosane are novel halometabolites with an unusual rearranged chamigrane framework. Antibacterial activities of these metabolites against marine bacteria are also described.
  15. Ling SK, Tanaka T, Kouno I
    J Nat Prod, 2001 Jun;64(6):796-8.
    PMID: 11421747
    A new iridoid glucoside with an ether linkage between C-3 and C-10 and a novel nonglycosidic iridoid with an ether linkage between C-3 and C-6 and a lactonic linkage at C-1, named macrophylloside (1) and macrophyllide (2), respectively, were isolated from the leaves of Rothmannia macrophylla, along with six known iridoids. Their structures were established by NMR and MS spectroscopies.
  16. Permana D, Lajis NH, Mackeen MM, Ali AM, Aimi N, Kitajima M, et al.
    J Nat Prod, 2001 Jul;64(7):976-9.
    PMID: 11473441
    Two new prenylated compounds, the benzoquinone atrovirinone (1) and the depsidone atrovirisidone (2), were isolated from the roots of Garcinia atroviridis. Their structures were determined on the basis of the analysis of spectroscopic data. While compound 2 showed some cytotoxicity against HeLa cells, both compounds 1 and 2 were only mildly inhibitory toward Bacillus cereus and Staphylococcus aureus.
  17. Xu YJ, Lai YH, Imiyabir Z, Goh SH
    J Nat Prod, 2001 Sep;64(9):1191-5.
    PMID: 11575954
    Nine new xanthones, parvixanthones A-I (1-9), isolated from the dried bark of Garcinia parvifolia, were found to have a common 1,3,6,7-oxygenated pattern for their xanthone nucleus, but various oxygenated isoprenyl or geranyl substituent groups. The structures were determined by spectroscopic methods.
  18. Ling SK, Tanaka T, Kouno I
    J Nat Prod, 2002 Feb;65(2):131-5.
    PMID: 11858743
    Methanolic extracts of the leaves, stems, and roots of Phyllagathis rotundifolia collected in Malaysia yielded seven galloylated cyanogenic glucosides based on prunasin, with six of these being new compounds, prunasin 2',6'-di-O-gallate (3), prunasin 3',6'-di-O-gallate (4), prunasin 4',6'-di-O-gallate (5), prunasin 2',3',6'-tri-O-gallate (6), prunasin 3',4',6'-tri-O-gallate (7), and prunasin 2',3',4',6'-tetra-O-gallate (8). Also obtained was a new alkyl glycoside, oct-1-en-3-yl alpha-arabinofuranosyl-(1-->6)-beta-glucopyranoside (9). For compounds 3-8, the galloyl groups were individually linked to the sugar moieties via ester bonds. All new structures were established on the basis of NMR and MS spectroscopic studies. In addition, prunasin (1), gallic acid and its methyl ester, beta-glucogallin, 3,6-di-O-galloyl-D-glucose, 1,2,3,6-tetra-O-galloyl-beta-D-glucose, strictinin, 6-O-galloyl-2,3-O-(S)-hexahydroxydiphenoyl-D-glucose, praecoxin B, and pterocarinin C were isolated and identified. The isolation of 1 and its galloyl derivatives (3-8) from a Melastomataceous plant are described for the first time.
  19. Ling SK, Komorita A, Tanaka T, Fujioka T, Mihashi K, Kouno I
    J Nat Prod, 2002 May;65(5):656-60.
    PMID: 12027736
    Six new sulfur-containing bis-iridoid glucosides, saprosmosides A-F (1-6), were isolated from the leaves of Saprosma scortechinii. From the stems of this same plant, two new iridoid glucosides, 3,4-dihydro-3-methoxypaederoside (8) and 10-O-benzoyldeacetylasperulosidic acid (12), were isolated. Their structures were elucidated by means of chemical, NMR, and mass spectroscopic methods. Additionally, 11 known iridoid glucosides were isolated and characterized as deacetylasperuloside, asperuloside, paederoside (7), deacetylasperulosidic acid (9), scandoside, asperulosidic acid, 10-acetylscandoside, paederosidic acid (10), 6-epi-paederosidic acid (11), methylpaederosidate, and monotropein. The structures of the new bis-iridoid glucosides were formed by intermolecular esterification between the glucose and carboxyl groups of three monomeric iridoid glucosides (7, 9, and 10).
  20. Kam TS, Sim KM
    J Nat Prod, 2002 May;65(5):669-72.
    PMID: 12027738
    Five new indole alkaloids of the ibogan type (1-5), in addition to 12 other known iboga alkaloids, were obtained from the leaf and stem-bark extract of the Malayan species Tabernaemontana corymbosa, viz., 19(S)-hydroxyibogamine (1), 19-epi-isovoacristine (2), isovoacryptine (3), 3R/S-ethoxyheyneanine (4), and 3R/S-ethoxy-19-epi-heyneanine (5). The structures were determined using NMR and MS analysis and comparison with known related compounds.
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