Aristolactams and Alkamides of Aristolochia gigantea

Holzbach, Juliana Cristina; Lopes, Lucia Maria Xavier

doi:10.3390/molecules15129462

Cited by 38 publications

(19 citation statements)

References 33 publications

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“…1 H-NMR (DMSO- d 6 , 500 MHz) δ: 9.36 (-OH), 8.11 (1H, t, 5.0 Hz, -NH), 7.39 (2H, d, 8.5 Hz, H-2, 6), 7.30 (1H, d, 15.5 Hz, H-7), 7.01 (2H, d, 8.0 Hz, H-2′, 6′), 6.78 (2H, d, 8.5 Hz, H-3, 5), 6.67 (2H, d, 8.0 Hz, H-3′, 5′), 6.38 (1H, 15.5 Hz, H-8), 3.31 (2H, m, H-8′), 2.64 (2H, t, 7.5 Hz, H-7′). The 1 H- and 13 C-NMR ( Table 2 ) spectral data are consistent with published data [ 29 , 30 ].…”

Section: Methodssupporting

confidence: 89%

Phenolic Compounds and Antioxidant Activities of Liriope muscari

Cheng

Liu

et al. 2012

Molecules

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Five phenolic compounds, namely N-trans-coumaroyltyramine (1), N-trans-feruloyltyramine (2), N-trans-feruloyloctopamine (3), 5,7-dihydroxy-8-methoxyflavone (4) and (3S)3,5,4′-trihydroxy-7-methoxy-6-methylhomoisoflavanone (5), were isolated from the fibrous roots of Liriope muscari (Liliaceae). Compounds 2–5 were isolated for the first time from the Liriope genus. Their in vitro antioxidant activities were assessed by the DPPH and ABTS scavenging methods with microplate assays. The structure-activity relationships of compounds 1–3 are discussed.

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Section: Methodssupporting

confidence: 89%

Phenolic Compounds and Antioxidant Activities of Liriope muscari

Cheng

Liu

et al. 2012

Molecules

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“…By comparison of the experiments and reported spectroscopic data ([α] D , UV, IR, NMR, and MS), known compounds were identified as one apocarotenoid: blumenol A ( 7 ) [ 13 ], one benzenoid: amisbenzoic acid ( 8 ) [ 14 ], one chlorophyll: pheophytin a ( 9 ) [ 15 ], one coumarin: isofraxidin ( 10 ) [ 16 ], six lignans: (+)-eudesmin ( 11 ) [ 17 ], (+)-methylpiperitol ( 12 ) [ 18 ], (+)-pinoresinol ( 13 ) [ 19 ], (+)-syringaresinol ( 14 ) [ 20 ], (2 S ,5 S )-diveratryl-(3 R ,4 S )-dimethyltetrahydrofuran ( 15 ) [ 21 ], and (+)-galbelgin ( 16 ) [ 22 ], three sesquiterpenoids: β-eudesmol ( 17 ) [ 23 ], caryophyllene oxide ( 18 ), and clovane-2α,9β-diol ( 19 ) [ 24 ], and one steroid: β-sitosterol ( 20 ) [ 25 ].…”

Section: Resultsmentioning

confidence: 99%

Phytochemical Investigation and Anti-Inflammatory Activity of the Leaves of Machilus japonica var. kusanoi

Hwang

et al. 2020

Molecules

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In a series of anti-inflammatory screenings of lauraceous plants, the methanolic extract of the leaves of Machilus japonica var. kusanoi (Hayata) J.C. Liao showed potent inhibition on both superoxide anion generation and elastase release in human neutrophils. Bioassay-guided fractionation of the leaves of M. japonica var. kusanoi led to the isolation of twenty compounds, including six new butanolides, machinolides A–F (1–6), and fourteen known compounds (7–20). Their structures were characterized by 1D and 2D NMR, UV, IR, CD, and MS data. The absolute configuration of the new compounds were unambiguously confirmed by single-crystal X-ray diffraction analyses (1, 2, and 3) and Mosher’s method (4, 5, and 6). In addition, lignans, (+)-eudesmin (11), (+)-methylpiperitol (12), (+)-pinoresinol (13), and (+)-galbelgin (16) exhibited inhibitory effects on N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation in human neutrophils with IC50 values of 8.71 ± 0.74 μM, 2.23 ± 0.92 μM, 6.81 ± 1.07 μM, and 7.15 ± 2.26 μM, respectively. The results revealed the anti-inflammatory potentials of Formosan Machilus japonica var. kusanoi.

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“…A phytochemical study of the roots of A. cordigera led to isolation and structural identification of 19 known compounds: eupomatenoid-7 (1) [24] [30], zuihonin B (9) [24], calopiptin (10) [24], aristolochic acid I (11) [31], aristolochic acid IV (12) [32], sodium aristolochate I (13) [31], sodium aristolochate IV a (14) [31], magnoflorine (15) [33], N-trans-feruloyltyramine (16) [33], 5-hydroxy-1H-indole-3-carboxylic acid ethyl ester (17) [17], hyrtiosin B (18) [34], and hyrtiosulawesine (19) [19]. In addition, two new indole alkaloids, 3,4-dihydro-hyrtiosulawesine (20) and 6-O-(β-glu- 3 Hz, δ C 112.9) and four quaternary carbons (δ C 153.8, 130.9, 127.6, 113.0) characteristic of a keto-indole unity, which was similar to that observed for 19.…”

Section: Resultsmentioning

confidence: 99%

Chemical Composition, Antiprotozoal and Cytotoxic Activities of Indole Alkaloids and Benzofuran Neolignan of Aristolochia cordigera

et al. 2017

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This is a comparative study on the intraspecific chemical variability of species, collected in two different regions of Brazil, Biome Cerrado (semiarid) and Biome Amazônia (coastal). The use of GC-MS and statistical methods led to the identification of 56 compounds. A higher percentage of palmitone and germacrene-D in the hexanes extracts of the leaves of plants from these respective biomes was observed. Phytochemical studies on the extracts led to the isolation and identification of 19 known compounds, including lignans, neolignans, aristolochic acids, indole--carboline, and indole alkaloids. In addition, two new indole alkaloids, 3,4-dihydro-hyrtiosulawesine and 6--(-glucopyranosyl)hyrtiosulawesine, were isolated and a new neolignan, -eupomatenoid-7, was obtained in a mixture with its known isomer eupomatenoid-7. Their structures were determined by spectroscopic methods, mainly by 1D- and 2D-NMR. The occurrence of indole alkaloids is being described for the first time in the Aristolochiaceae family. Moreover, the susceptibility of intracellular amastigote and promastigote forms of to the alkaloids and eupomatenoid-7 were evaluated. This neolignan exhibited low activity against promastigotes (IC = 46 µM), while the alkaloids did not show inhibitory activity. The new alkaloid 6--(-glucopyranosyl)hyrtiosulawesine exhibited activity in the low micromolar range against , with an IC value of 5 µM and a selectivity index higher than 50.

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Aristolactams and Alkamides of Aristolochia gigantea

Cited by 38 publications

References 33 publications

Phenolic Compounds and Antioxidant Activities of Liriope muscari

Phenolic Compounds and Antioxidant Activities of Liriope muscari

Phytochemical Investigation and Anti-Inflammatory Activity of the Leaves of Machilus japonica var. kusanoi

Chemical Composition, Antiprotozoal and Cytotoxic Activities of Indole Alkaloids and Benzofuran Neolignan of Aristolochia cordigera

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