Cinnamoyltyramine derivatives and other constituents from Sparattanthelium tupiniquinorum (Hernandiaceae)

Pereira, Cynara A.B.; Oliveira, Fernando M. de; Conserva, Lúcia M.; Lemos, Rosângela P. Lyra; Andrade, Eloísa Helena A.

doi:10.1016/j.bse.2007.03.014

Cited by 5 publications

(3 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compounds 2 − 7 represent only a fraction of the naturally occurring cinnamoylphenethylamines, but one or more of them have been reported in the following families: Alliaceae , Amaranthaceae − , Anacardiaceae , Annonaceae , Aristolochiaceae , Cannabidaceae , Chenopodiaceae , Convolvulaceae , Euphobiaceae , Flacourtiaceae , Fumariaceae , Hernandiaceae , Lauraceae , Leguminosae , Liliaceae , Magnoliaceae , Malvaceae , Menispermaceae , Monimiaceae , Nyctagenaceae , Papaveraceae , Piperaceae , Plumbaginaceae , Polygonaceae , Portulacaceae , Ruscaceae , Rutaceae , Solanaceae ,, , Ulmaceae , Vitaceae , and Zygophyllaceae .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Quantitation of Six Phenolic Amides inAmaranthusspp.

Pedersen¹,

Steffensen²,

Christophersen³

et al. 2010

J. Agric. Food Chem.

View full text Add to dashboard Cite

Cinnamoylphenethylamines are phenolic amides in which cinnamic acid provides the acid moiety and phenethylamine the amine moiety. Single ion monitoring (SIM) in LC-MS was performed on amaranth leaf extracts. Masses corresponding to sets of regioisomers, including previously reported compounds, were examined. Six peaks were detected and their corresponding standards synthesized for a quantitative LC-MS/MS investigation of cinnamoylphenethylamines in amaranth. Four cinnamoylphenethylamines (caffeoyltyramine, feruloyldopamine, sinapoyltyramine, and p-coumaroyltyramine) are reported in the Amaranthaceae for the first time; also, one rare compound, feruloyl-4-O-methyldopamine, appeared to be quite common in the genus Amaranthus. Feruloyldopamine showed moderate antifungal activity toward an isolate of Fusarium culmorum. Our LC-MS approach, in conjunction with the straightforward synthesis, provides a simple, reliable way of quantitatively investigating cinnamoylphenethylamines in plants. Concentrations of cinnamoylphenethylamines vary widely: feruloyltyramine was present in quantities of 5.26 to 114.31 microg/g and feruloyldopamine in quantities of 0.16 to 10.27 microg/g, depending on the plant sample.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis and Quantitation of Six Phenolic Amides inAmaranthusspp.

Pedersen¹,

Steffensen²,

Christophersen³

et al. 2010

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…N - trans -sinapoyltyramine (NTST, 52 , Figure 4 ), NCFT, NTFT and NTCT were isolated together with 23 known compounds from the bark stems of Polyalthia longifolia var. pendula [ 40 ], while NTFT and NTCT were also isolated from Sparattanthelium tupiniquinorum (Hernandiaceae) collected in Brazil [ 42 , 43 ].…”

Section: Structure and Biological Activity Of Cinnamoyltyramine Alkylamides And Of Co-metabolites Isolated From The Same Natural Sourcesmentioning

confidence: 99%

Natural Bioactive Cinnamoyltyramine Alkylamides and Co-Metabolites

Evidente

Masi

2021

Biomolecules

View full text Add to dashboard Cite

Natural products are a vital source for agriculture, medicine, cosmetic and other fields. Among them alkylamides are a broad and expanding group found in at least 33 plant families. Frequently, they possess a simple carbon skeleton architecture but show broad structural variability and important properties such as immunomodulatory, antimicrobial, antiviral, larvicidal, insecticidal and antioxidant properties, amongst others. Despite to these several and promising biological activities, up to today, only two reviews have been published on natural alkylamides. One focuses on their potential pharmacology application and their distribution in the plant kingdom and the other one on the bioactive alkylamides specifically found in Annona spp. The present review is focused on the plant bioactive cinnamoyltyramine alkylamides, which are subject of several works reported in the literature. Furthermore, the co-metabolites isolated from the same natural sources and their biological activities are also reported.

show abstract

“…Dactylicapnos torulosa trans-266 (Rucker et al, 1994) Hernandiaceae Sparattanthelium tupiniquinorum trans-264, trans-266 (Pereira et al, 2007) Lauraceae Actinodaphne longifolia trans-266, trans-273 (Tanaka et al, 1989) Leguminosae Mucuna birdwoodiana trans-266 (Goda et al, 1987)…”

Section: Fumariaceaementioning

confidence: 99%

Natural Alkamides: Pharmacology, Chemistry and Distribution

Rios¹

2012

Drug Discovery Research in Pharmacognosy

View full text Add to dashboard Cite

Alkamides are a broad and expanding group of bioactive natural compounds found in at least 33 plant families. Despite the relatively simple molecular architecture of alkamides (fig. 1), these natural products show broad structural variability and an important range of biological activities, such as immunomodulatory, antimicrobial, antiviral, larvicidal, insecticidal, diuretic, pungent, analgesic, cannabimimetic and antioxidant activities. Additionally, alkamides are involved in the potentiation of antibiotics and the inhibition of prostaglandin biosynthesis, RNA synthesis and the arachidonic acid metabolism, among others. Many plant species containing alkamides have been used in traditional medicine by different civilizations around the world. Many of the plants containing these natural products have been used in the treatment of toothaches and sore throats (Rios-Chavez et al., 2003). These compounds are present in different organs of the plant, such as roots (Heliopsis longipes, Echinaceae purpurea, Achillea wilhelmsii, Acmella oppositifolia, Asiasarum heterotropoide, Cissampelos glaberrima, etc.), leaves and stems (Aristolochia gehrtii, Phyllanthus fraternus, Amaranthus hypochondriacus, Achyranthes ferruginea, etc.), the pericarpium (Zanthoxylum piperitum and Piper spp.), the placenta of Capsicum spp., the fruits of Piper longum, the flowers of Spilanthes acmella, the seeds of the Piper species and tubers of Lepidium meyenii. It is believed that alkamides act as plant growth regulators, promoting or inhibiting the growth and formation of roots in a dose-dependent manner and showing a positive effect in plant biomass production (Campos-Cuevas, et al., 2008). Structurally, natural alkamides commonly have an aliphatic, cyclic or aromatic amine residue, and a C8 to C18 saturated or unsaturated chain (including double or triple bonds, or both) acid, which can also be aromatic. The nature of the acid (carbon chain lengths, unsaturation level, stereochemistry, etc.) and the amine residues are characteristic of each family and genus of plants such that these characteristics serve as chemotaxonomic criteria (fig. 1). Because the nitrogen atom of alkamides is not part of a heterocyclic ring, these compounds are classified as protoalkaloids or pseudoalkaloids.

show abstract

Cinnamoyltyramine derivatives and other constituents from Sparattanthelium tupiniquinorum (Hernandiaceae)

Cited by 5 publications

References 17 publications

Synthesis and Quantitation of Six Phenolic Amides inAmaranthusspp.

Synthesis and Quantitation of Six Phenolic Amides inAmaranthusspp.

Natural Bioactive Cinnamoyltyramine Alkylamides and Co-Metabolites

Natural Alkamides: Pharmacology, Chemistry and Distribution

Contact Info

Product

Resources

About