13C-NMR-spektren einiger acridon-alkaloide

Bergenthal, Dieter; Mester, I.; Rózsa, Zs.; Reisch, J.

doi:10.1016/s0031-9422(00)90937-3

Cited by 35 publications

(23 citation statements)

References 15 publications

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“…The relatively strong upfield shifted C-4 signal at δ 104.8 in 13 C NMR spectrum for aromatic carbon fitted well with the earlier report [5]. The rest of the signals of 13 C NMR spectrum, when compared with the literature data, [5,30,33,34] supported that 1 is a 3-hydroxy-1,5,6-trimethoxy-9-acridone.…”

Section: Resultssupporting

confidence: 89%

Aromatase and glycosyl transferase inhibiting acridone alkaloids from fruits of Cameroonian Zanthoxylumspecies

Wouatsa

Misra

Kumar

et al. 2013

Chemistry Central Journal

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BackgroundZanthoxylum zanthoxyloides and Z. leprieurii fruits are commonly used in traditional system of medicine for diarrhea, pain, wound healing, etc. in Cameroon, Africa. Z. leprieurii fruits have been chemically studied for its bioactive compounds whereas the investigation on Z. zanthoxyloides fruits is lacking.ResultsAfter a detailed chemical analysis of the fruits of Z. leprieurii and Z. zanthoxyloides, a series of new acridone alkaloids, namely, 3-hydroxy-1,5,6-trimethoxy-9-acridone (1), 1,6-dihydroxy-3-methoxy-9-acridone (2), 3,4,5,7-tetrahydroxy-1-methoxy-10-methyl-9-acridone (3), 4-methoxyzanthacridone (8), 4-hydroxyzanthacridone (9), 4-hydroxyzanthacridone oxide (2,4’) (10) have been isolated. The known acridones which have been characterized are, helebelicine A (4), 1-hydroxy-3-methoxy-10-methyl-9-acridone (5), 1,3-dihydroxy-4-methoxy-10-methyl-9-acridone (6) and tegerrardin A (7). The in vitro antibacterial and cytotoxic screening of these acridones reveal that compound 3 has a moderate antibacterial activity (MIC 125 μg/mL) against Micrococcus luteus and Pseudomonas aeruginosa while compound 1 shows a moderate cytotoxic effect (IC50 of 86 μM) against WRL-68 (liver cancer cell line). Furthermore, the molecular modeling of these acridones predicted the structural basis for their mode of action and binding affinity for aromatase, quinone reductase and WAAG, a glycosyltransferase involved in bacterial lipopolysaccharide synthesis. Computational approaches, quantitative SAR and modeling studies predicted that acridones 1, 2, 3, 4, 9 and 10 were the inhibitors of glycosyltransferase while 1, 8, 9 and 10, the inhibitors of aromatase.ConclusionsA total of 10 acridones have been isolated out of which 6 are new (1, 2, 3, 8, 9 and 10). Alkaloids 8, 9 and 10, having novel tetracyclic acridone structure with new carbon skeleton, have now been named as zanthacridone. The quantitative SAR and molecular modeling studies suggested that the compounds 1, 9 and 10 are inhibitors of both aromatase and glycosyltransferase.

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Section: Resultssupporting

confidence: 89%

Aromatase and glycosyl transferase inhibiting acridone alkaloids from fruits of Cameroonian Zanthoxylumspecies

Wouatsa

Misra

Kumar

et al. 2013

Chemistry Central Journal

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“…The authors supported this finding with 1 H NMR chemical shifts of two primary O-acetyl groups (d 2.10 and 2.13) of diacetylated gravacridontriol. 13 C NMR data (Bergenthal et al, 1979) confirmed the glucosidic structure of gravacridondiol and -triol but were not suitable to prove the glucosidation site. Our NMR analysis, especially HMBC studies, of glucosides 1 and 2 led to revised structures of both glucosides with the glucose attached to the tertiary hydroxyl groups.…”

Section: Discussionmentioning

confidence: 94%

Specific accumulation and revised structures of acridone alkaloid glucosides in the tips of transformed roots of Ruta graveolens

2004

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“…16, No. 3A, 2005 methanol extract from leaves of A. rubra afforded two new compounds (1 and 2a) and known compounds ( Figure 1) arborinine (3), N-methyl-1-hydroxy-3-methoxyacridone (4), 5 skimmianine (5), 6 kokusagine (6), 7 isodutaduprine (7), 8 isoskimmianine (8), and isokokusagine (9), which were identified through comparison of their NMR spectral data with the literature.…”

Section: Resultsmentioning

confidence: 99%

“…was investigated. Thus, here we report the isolation, identification and characterization of two new substances (1 and 2a) and seven known compounds (3)(4)(5)(6)(7)(8)(9) from methanol extract of leaves of this plant, in addition to their trypanocidal activities.…”

Section: Introductionmentioning

confidence: 99%

New pyrone and quinoline alkaloid from Almeidea rubra and their trypanocidal activity

Ambrozin¹,

Mafezoli²,

Vieira³

et al. 2005

J. Braz. Chem. Soc.

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O estudo da fração acetato de etila do extrato metanólico das folhas de Almeidea rubra A. St.-Hil. (Rutaceae) permitiu o isolamento de duas substâncias inéditas: 4-metoxi-6-[2-(metilamino)fenil]-2H-piran-2-ona e acetato de rel-(7R,8R)-8-[(E)-3-hidroxi-3-metil-1-butenil]-4,8-dimetoxi-5,6,7,8-tetraidrofuro[2,3-b]quinolin-7-ila; e dos alcalóides arborinina, N-metil-1-hidroxi-3-metoxiacridona, esquimianina, cocusagina, isodutaduprina, isoesquimianina e isococusagina. Através da análise dos dados espectroscópicos foram estabelecidas as estruturas químicas das substâncias isoladas sendo que para os alcalóides inéditos tais dados são descritos pela primeira vez. Além disso, os ensaios bilógicos sobre as formas tripomastigotas do Trypanosoma cruzi das substâncias isoladas mostraram que elas possuem atividade tripanocida moderada.The investigation of the ethyl acetate fraction of methanol extract from leaves of Almeidea rubra A. St.-Hil. (Rutaceae) afforded two new compounds 4-methoxy-6-[2-(methylamino)phenyl]-2H-pyran-2-one and rel-(7R,8R)-8- [(E)-3-hydroxy-3-methyl-1-butenyl]-4,8-dimethoxy-5,6,7,8-tetrahydrofuro[2,3-b]quinoline-7-yl acetate, along with the known compounds arborinine, N-methyl-1-hydroxy-3-methoxyacridone, skimmianine, kokusagine, isodutaduprine, isoskimmianine, and isokokusagine. Their structures were established based on their spectral data, and for the new compounds these data are described herein. Additionally, these compounds were assayed on the tripomastigote forms of Trypanosoma cruzi showing moderate trypanocidal activity.

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13C-NMR-spektren einiger acridon-alkaloide

Cited by 35 publications

References 15 publications

Aromatase and glycosyl transferase inhibiting acridone alkaloids from fruits of Cameroonian Zanthoxylumspecies

Aromatase and glycosyl transferase inhibiting acridone alkaloids from fruits of Cameroonian Zanthoxylumspecies

Specific accumulation and revised structures of acridone alkaloid glucosides in the tips of transformed roots of Ruta graveolens

New pyrone and quinoline alkaloid from Almeidea rubra and their trypanocidal activity

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