Nitro derivatives and other constituents of Aristolochia melastoma

Nogueira, Cláudio Rodrigo; Lopes, Lucia Maria Xavier

doi:10.1590/s0100-40422012000400024

Cited by 7 publications

(5 citation statements)

References 15 publications

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“…Metabolites B–G were identified as quercetin 3- O -rutinoside, kaempferol 3- O -gentiobioside, kaempferol 3- O -robinobioside, kaempferol 3- O -rutinoside, isorhamnetin 3- O -robinobioside and isorhamnetin 3- O -rutinoside, respectively ( Figures 3B–G ). The observed chemical shifts accorded with those of values reported in the literature ( Demırezer et al, 2006 ; Güvenalp et al, 2006 ; Nogueira and Lopes, 2012 ; Duong et al, 2017 ; Viet Thanh et al, 2018 ; Supplementary Table S3 ). Each molecular formula and the MS/MS fragments are summarized in Supplementary Table S2 .…”

Section: Resultssupporting

confidence: 88%

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Molecular Basis Underlying Common Cutworm Resistance of the Primitive Soybean Landrace Peking

et al. 2020

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The common cutworm (CCW; Spodoptera litura ) is one of the major insect pests of soybean in Asia and Oceania. Although quantitative trail loci related to CCW resistance have been introduced into leading soybean cultivars, these do not exhibit sufficient resistance against CCW. Thus, understanding the genetic and metabolic resistance mechanisms of CCW as well as integrating other new resistance genes are required. In this study, we focused on a primitive soybean landrace, Peking, which has retained resistances to various pests. We found a resistance to CCW in Peking by the detached-leaf feeding assay, and subsequently determined the genetic and metabolic basis of the resistance mechanism using chromosome segment substitution lines (CSSLs) of Peking. Several characteristic metabolites for Peking were identified by the metabolomic approach using liquid chromatography/mass spectrometry combined with a principle component analysis. The structure of seven metabolites were determined by nuclear magnetic resonance (NMR) analysis. The genomic segments of Peking on chromosome 06 (Chr06) and Chr20 had a clear association with these metabolites. Moreover, a line possessing a Peking genomic segment on Chr20 inhibited growth of the CCW. The genetic factors and the metabolites on Chr20 in Peking will be useful for understanding mechanisms underlying CCW resistance and breeding resistant soybean cultivars.

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Section: Resultssupporting

confidence: 88%

“…Among the domestication-related traits, changes in the secondary metabolites are known to occur in 66% of crops (Meyer et al, 2012). For example, toxic or bitter compounds have decreased along with changes in the pigmentation of fruits or seeds.…”

Section: Introductionmentioning

confidence: 99%

Molecular Basis Underlying Common Cutworm Resistance of the Primitive Soybean Landrace Peking

et al. 2020

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“… 18 , 33 The nitroethyl-containing phenolic glycoside 11 has been found previously in plants from the Menispermaceae, 34 Ranunculaceae, 32 and Aristolochiaceae families. 35 Interestingly, these families all produce strikingly similar alkaloid profiles to Papaver in terms of benzylisoquinolines and their downstream biosynthetic products (e.g., aporphines and/or protoberberines). 36 , 37 4-(2-Nitroethyl)phenol, a presumed biosynthetic precursor of 11 , is produced from tyrosine in response to osmotic stress in cell cultures of Eschscholzia californica (Papaveraceae).…”

Section: Results and Discussionmentioning

confidence: 97%

Spatial Distribution and Stability of Cholinesterase Inhibitory Protoberberine Alkaloids from Papaver setiferum

et al. 2021

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During a research program to identify new cholinesterase inhibitors of natural origin, two new 7,8-didehydroprotoberberine alkaloids ( 1 and 2 ) and nine known compounds ( 3 – 11 ) were isolated from the capsules of the common ornamental poppy, Papaver setiferum (previously P. pseudo-orientale ). Despite their reported instability, the 7,8-didehydroprotoberberines isolated herein appeared relatively stable, particularly as their trifluoroacetic acid salts. The spatial distributions of the isolated alkaloids were also analyzed using desorption electrospray ionization imaging mass spectrometry. The alkaloids were localized predominantly within the walls and vascular bundles of the capsules, with the highest relative abundances occurring in the lower half of the capsules toward the peduncle. The relative abundances of the alkaloids were also compared across plant development stages. Although most alkaloids did not show clear patterns in their concentration across development stages, the concentration of suspected oxidation products clearly spiked upon plant death. Finally, all isolated natural products were screened for inhibitory activities against a panel of cholinesterases, from both human and animal sources. These studies identified several competitive inhibitors of cholinesterases with potency in the low micromolar range ( 1 – 4 , 6 , 7 ), offering new lead compounds for the development of cholinesterase inhibitory drugs.

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“…The FDAE antioxidant potential observed can be attributed partly to the presence of tannins, and mainly to the high total phenolic content, since quantitative phytochemical analyses revealed the content of these compounds in FDAE as 0.02 ± 0.01 and 52.67 ± 0.13 mg/g, respectively. These values are in conformity with what was expected for an Aristolochia sp., provided that species belonging to this genus are rich sources of flavonoids, particularly diglycosides, and other phenolic chemical constituents, mainly phenylethyl and phenanthrene derivatives, phenylpropanoids, lignoids, alkamides, and alkaloids (LOPES et al, 2001;NOGUEIRA & LOPES, 2012).…”

Section: Resultsmentioning

confidence: 99%

Toxicological properties of an aqueous extract of Aristolochia triangularis leaves, using the brine shrimp lethality and Allium cepa bioassays

et al. 2019

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The aqueous extract of Aristolochia triangularis leaves showed activity against Artemia salina larvae, with an LD50 of 370.6 µg/mL. In experiments with Allium cepa seeds, the extract caused a 51.26% reduction in the germination index, inhibited mean root growth, and was cytotoxic at concentrations of 668 and 2,000 µg/mL. Its antioxidant activity was additionally assessed in this research and the ferric reducing antioxidant power value was found to be 391.2 µM/g. Such health-beneficial property can be attributed partly to the total phenolic content, spectrophotometrically determined as 52.67 mg/g. The occurrence of cytotoxicity suggested caution when consuming teas from A. triangularis leaves for medicinal purposes, and equally reveals the need for further studies to investigate their adverse effects.

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Nitro derivatives and other constituents of Aristolochia melastoma

Cited by 7 publications

References 15 publications

Molecular Basis Underlying Common Cutworm Resistance of the Primitive Soybean Landrace Peking

Molecular Basis Underlying Common Cutworm Resistance of the Primitive Soybean Landrace Peking

Spatial Distribution and Stability of Cholinesterase Inhibitory Protoberberine Alkaloids from Papaver setiferum

Toxicological properties of an aqueous extract of Aristolochia triangularis leaves, using the brine shrimp lethality and Allium cepa bioassays

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