2005
DOI: 10.1055/s-2005-837784
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New Aromatic Compounds from the Marine MangroveBruguiera gymnorrhiza

Abstract: The phytochemical investigation of the stem of Bruguiera gymnorrhiza yielded five new aromatic compounds (1-5), of which the bruguierols A - C (1-3) represent a new structural skeleton in natural product chemistry. All structures have been determined by NMR spectroscopic studies. Among them, 3 showed moderate activity against Gram-positive and Gram-negative bacteria including mycobacteria and resistant strains (MICs 12.5 microg/mL).

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Cited by 44 publications
(47 citation statements)
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“…(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) 3-Alkylisochromans are quite rare as natural products; the known derivatives include (3S)-6-hydroxy-8-methoxy-3,5-dimethylisochroman, [5] the anticoccidial arohynapene, [6] the toxic 8-hydroxy-6-methoxy-3,7-dimethylisochroman, [7] and the antibacterial bruguierol C. [8] Moreover, the isolated 1-hydroxy-3-heptylisochroman derivative CJ-12,373 was reported to have topoisomerase II inhibitor activity. [9] The absolute configurations of these isochroman derivatives have not been determined or are only tentatively proposed on the basis of biogenetic origin.…”
Section: Introductionmentioning
confidence: 99%
“…(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) 3-Alkylisochromans are quite rare as natural products; the known derivatives include (3S)-6-hydroxy-8-methoxy-3,5-dimethylisochroman, [5] the anticoccidial arohynapene, [6] the toxic 8-hydroxy-6-methoxy-3,7-dimethylisochroman, [7] and the antibacterial bruguierol C. [8] Moreover, the isolated 1-hydroxy-3-heptylisochroman derivative CJ-12,373 was reported to have topoisomerase II inhibitor activity. [9] The absolute configurations of these isochroman derivatives have not been determined or are only tentatively proposed on the basis of biogenetic origin.…”
Section: Introductionmentioning
confidence: 99%
“…[16][17][18][19][20][21] Structurally complex molecules possessing oxa-and azabicyclo[3.2.1]octane skeletons have been rapidly and efficiently generated by [5+2] cycloadditions of 3-oxidopyrylium 22,23 and 3-oxidopyridinium dipoles. 24 Although synthetically very powerful, these methods can be problematic.…”
Section: Introductionmentioning
confidence: 99%
“…an ABX system of an aromatic ring, and multiplets corresponding to H [2][3][4][5][6] Table 1). The DQFCOSY, HMQC and HMBC data ( , and 61.8 (t, C-5Љ) were consistent with a C-1 substituted arabinofuranose.…”
mentioning
confidence: 99%