5,7-Dihydroxy-3,6-Dimethoxy-3′,4′-Methylendioxyflavone

Tjahjandarie, Tjitjik Srie; Saputri, Ratih Dewi; Hasanah, U.; Rachmadiarti, Fida; Tanjung, Mulyadi

doi:10.3390/m1007

Cited by 4 publications

(3 citation statements)

References 11 publications

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“…The dichloromethane (CH 2 Cl 2 ) extract of the root bark of Erythrina lysistemon yielded 24 phenolic compounds, including 17 pterocarpans, two isoflavanones, one flavanone, two isoflavans, one 2-arylbenzofuran, and an isoflava-3-ene. Fifteen compounds, erybraedin A (1), 22 erythrabyssin II (2), 23 phaseollidin (3), 24 phaseollin (4), 25 eryzerin C (5), 26 eriotrichin B (bidwillon A) (6), 22 erybraedin B (10), 27 eryvarin L vignafuran (15), 28,29 eryvarin K ( 16), 29 eryvarin H (17), 29 eryvarin C (18), 30 orientanol E (21), 31 eryvarin D (22), 30 8-methoxyneorautenol (23), 32 and abyssinone V 4′-Omethyl ether (24) 33 have been reported previously, while nine pterocarpans (7−9, 11 −14, 19, and 20) are reported here for the first time (Figure 1). The structures of the known compounds were confirmed by comparison of their physical and spectroscopic data with those reported in the literature as referenced above.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Antiangiogenic Pterocarpan and Flavonoid Constituents of Erythrina lysistemon

et al. 2023

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The roots of Erythrina lysistemon, growing in Egypt, yielded 24 flavonoid compounds, including 17 pterocarpans, two isoflavanones, one flavanone, two isoflavans, one 2-arylbenzofuran, and an isoflava-3-ene. Nine pterocarpans have not been reported previously (7–9, 11–14, 19, and 20), and 11 are reported here for the first time from this species. Structures were established using HRESIMS, NMR, and circular dichroism techniques. Selected compounds were tested for their ability to block the growth of human retinal endothelial cells and antiangiogenic activity in vitro. The isoflavonoids 5 and 6, and the pterocarpans 1, 2, 4, 20, and 22 demonstrated selective antiproliferative activities on endothelial cells compared to a nonendothelial cell type, with concentration-dependent antiangiogenic effects in vitro against HRECs, a cell type relevant to neovascular eye diseases.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Antiangiogenic Pterocarpan and Flavonoid Constituents of Erythrina lysistemon

et al. 2023

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“…The 1 H NMR spectra of blank liposomes (Lipo-Blank) and liposomes loaded with PQ (Lipo-PQ), CQ (Lipo-CQ), and both drugs (Lipo-PQCQ) were analyzed using a JEOL 400 ECA spectrophotometer (JEOL, Tokyo, Japan) at 400 MHz 53 . Approximately 5 mg of freeze-dried samples were dissolved in CDCL 3 to produce a concentration of 10 mg/ml with the data integration subsequently analyzed by computer using JEOL Delta v5.04.…”

Section: Methodsmentioning

confidence: 99%

Interactions of primaquine and chloroquine with PEGylated phosphatidylcholine liposomes

Miatmoko

Nurjannah

Nehru

et al. 2021

Sci Rep

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This study aimed to analyze the interaction of primaquine (PQ), chloroquine (CQ), and liposomes to support the design of optimal liposomal delivery for hepatic stage malaria infectious disease. The liposomes were composed of hydrogenated soybean phosphatidylcholine, cholesterol, and distearoyl-sn-glycero-3-phosphoethanolamine-N-(methoxy[polyethyleneglycol]-2000), prepared by thin film method, then evaluated for physicochemical and spectrospic characteristics. The calcein release was further evaluated to determine the effect of drug co-loading on liposomal membrane integrity. The results showed that loading PQ and CQ into liposomes produced changes in the infrared spectra of the diester phosphate and carbonyl ester located in the polar part of the phospholipid, in addition to the alkyl group (CH2) in the nonpolar portion. Moreover, the thermogram revealed the loss of the endothermic peak of liposomes dually loaded with PQ and CQ at 186.6 °C, which is identical to that of the phospholipid. However, no crystallinity changes were detected through powder X-ray diffraction analysis. Moreover, PQ, with either single or dual loading, produced the higher calcein release profiles from the liposomes than that of CQ. The dual loading of PQ and CQ tends to interact with the polar head group of the phosphatidylcholine bilayer membrane resulted in an increase in water permeability of the liposomes.

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“…Rutaceae are known for their extremely diverse secondary metabolites that include many alkaloids derived from anthranilic acid, limonoids, coumarins, and acetophenones. Melicope species are proven to be producers of many interesting secondary metabolites including polymethoxylated flavonoids, furanocoumarins, acetophenones and quinolone alkaloids [ 9 , 10 , 11 , 12 , 13 , 14 ]. Moreover, several Melicope species are used in traditional and modern medicine [ 15 , 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

New Acetophenones and Chromenes from the Leaves of Melicope barbigera A. Gray

Bandolik

Kassack

et al. 2021

Molecules

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The dichloromethane extract from leaves of Melicope barbigera (Rutaceae), endemic to the Hawaiian island of Kaua’i, yielded four new and three previously known acetophenones and 2H-chromenes, all found for the first time in M. barbigera. The structures of the new compounds obtained from the dichloromethane extract after purification by chromatographic methods were unambiguously elucidated by spectroscopic analyses including 1D/2D NMR spectroscopy and HRESIMS. The absolute configuration was determined by modified Mosher’s method. Compounds 2, 4 and the mixture of 6 and 7 exhibited moderate cytotoxic activities against the human ovarian cancer cell line A2780 with IC50 values of 30.0 and 75.7 µM for 2 and 4, respectively, in a nuclear shrinkage cytotoxicity assay.

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5,7-Dihydroxy-3,6-Dimethoxy-3′,4′-Methylendioxyflavone

Abstract: A new flavonoid derivative, namely 5,7-dihydroxy-3,6-dimethoxy-3′,4′-methylenedioxyflavone (1), was isolated from the leaves of Melicope glabra (Blume) T.G. Hartley. The structure of 1 was elucidated based on their UV, IR, HRESIMS, and 1D and 2D NMR spectral data.

Cited by 4 publications

References 11 publications

Antiangiogenic Pterocarpan and Flavonoid Constituents of Erythrina lysistemon

Antiangiogenic Pterocarpan and Flavonoid Constituents of Erythrina lysistemon

Interactions of primaquine and chloroquine with PEGylated phosphatidylcholine liposomes

New Acetophenones and Chromenes from the Leaves of Melicope barbigera A. Gray

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5,7-Dihydroxy-3,6-Dimethoxy-3′,4′-Methylendioxyflavone

Abstract: A new flavonoid derivative, namely 5,7-dihydroxy-3,6-dimethoxy-3′,4′-methylenedioxyflavone (1), was isolated from the leaves of Melicope glabra (Blume) T.G. Hartley. The structure of 1 was elucidated based on their UV, IR, HRESIMS, and 1D and 2D NMR spectral data.

Cited by 4 publications

References 11 publications

Antiangiogenic Pterocarpan and Flavonoid Constituents of Erythrina lysistemon

Antiangiogenic Pterocarpan and Flavonoid Constituents of Erythrina lysistemon

Interactions of primaquine and chloroquine with PEGylated﻿ phosphatidylcholine liposomes

New Acetophenones and Chromenes from the Leaves of Melicope barbigera A. Gray

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Product

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Interactions of primaquine and chloroquine with PEGylated phosphatidylcholine liposomes