Note Iridoid Glucosides, Phenylpropanoid Derivatives and Flavanoids from Bartsia alpina

Cuendet, Muriel; Potterat, Olivier; Hostettmann, Kurt

doi:10.1076/phbi.37.4.318.5808

Cited by 6 publications

(7 citation statements)

References 10 publications

(11 reference statements)

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“…Compounds 3, 4 and 6 were tested for antioxidant activity in previous reports [23,44]. Although no DPPH scavenging activity was found for these compounds, interestingly, through a β-carotene bleaching assay [23], compound 6 was Despite the similar chemical structures of 3 and 4, differences in their biological activities have been reported before. Compounds 4, 1 and 3, isolated from M. arvense, were reported to display antiprotozoal effects on different species, showing a certain degree of species-specificity [24].…”

Section: Resultsmentioning

confidence: 96%

“…Optical rotation allowed us to unequivocally identify the stereochemistry of the compounds by comparing with the values of the natural iridoids, which is a well-established family of natural products among which absolute stereochemistry was previously reported by chiroptical methods and X Ray [20,21]. Compounds 1 [16] and 2-6 were previously isolated from B. trixago [17,22] and other iridoidcontaining plants [23][24][25][26][27][28][29][30]. The allelopathic effects of compounds 1-6 were assayed at 100 µg/mL on O. cumana radicles (Figure 3).…”

Section: Resultsmentioning

confidence: 99%

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Iridoid Glycosides Isolated from Bellardia trixago Identified as Inhibitors of Orobanche cumana Radicle Growth

Soriano

Siciliano

Fernández‐Aparicio

et al. 2022

Toxins

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Orobanche cumana is an obligate holoparasitic plant with noxious effects in sunflower crops. Bellardia trixago is a facultative hemiparasitic plant that infects ruderal plants without noxious significance in agriculture and is known to produce a wide spectrum of bioactive metabolites. The objective of this study was to evaluate the allelopathic effects of B. trixago on the growth of O. cumana seedlings. Three different extracts using solvents of increasing polarity (n-hexane, dichloromethane and ethyl acetate) were prepared from the flowers, aerial green organs and roots of two populations, a white-flowered and a yellow-flowered population of B. trixago, both collected in southern Spain. Each extract was studied using allelopathic screenings on O. cumana which resulted in the identification of allelopathic activity of the ethyl acetate extracts against Orobanche radicles. Five iridoid glycosides were isolated together with benzoic acid from the ethyl acetate extract of aerial green organs by bio-guided purification. These compounds were identified as bartsioside, melampyroside, mussaenoside, gardoside methyl ester and aucubin. Among them, melampyroside was found to be the most abundant constituent in the extract (44.3% w/w), as well as the most phytotoxic iridoid on O. cumana radicle, showing a 72.6% inhibition of radicle growth. This activity of melampyroside was significantly high when compared with the inhibitory activity of benzoic acid (25.9%), a phenolic acid with known allelopathic activity against weeds. The ecotoxicological profile of melampyroside was evaluated using organisms representing different trophic levels of the aquatic and terrestrial ecosystems, namely producers (green freshwater algae Raphidocelis subcapitata and macrophyte Lepidium sativum), consumers (water flea Daphnia magna and nematode Caenorhabditis elegans) and decomposers (bacterium Aliivibrio fischeri). The ecotoxicity of melampyroside differed significantly depending on the test organism showing the highest toxicity to daphnia, nematodes and bacteria, and a lower toxicity to algae and macrophytes. The findings of the present study may provide useful information for the generation of green alternatives to synthetic herbicides for the control of O. cumana.

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Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

confidence: 99%

Iridoid Glycosides Isolated from Bellardia trixago Identified as Inhibitors of Orobanche cumana Radicle Growth

Soriano

Siciliano

Fernández‐Aparicio

et al. 2022

Toxins

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“…Three iridoid glucosides, two phenylpropanoid derivatives and one flavonoid have been isolated from the methanolic whole plant extract of B. alpina ; some of these compounds have radical scavenging activity against DPPH or antioxidant activity against beta‐carotene on TLC bioassay (Cuendet et al . 1999).…”

Section: Structure and Physiologymentioning

confidence: 99%

Bartsia alpina L.

Taylor

Rumsey

2003

Journal of Ecology

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“…The second classes are used in modern industry and medicine. Iridoids compose a class of natural compounds which have various biological activities such as antiviral [2], anti-allergic, anti-anaphylactic, analgesic [3], antioxidant [4,5], antimicrobial, antirheumatic, laxative, hypotensive, sedative, antitumor [2,6], immunostimulant [7,9], antimicrobial [10,11] and hepatotoxic [13][14][15]. Others show radical scavenging activity against DPPH, antioxidant activity against β-carotene [12] and significant inhibition of UVB-induced: Activator Protein-1 activity in cell culture [16,17].…”

Section: Introductionmentioning

confidence: 99%

Studies of Trans- and Cis-Xylomollin Molecular Structures Using Molecular Dynamics Simulations

Mahboub

2012

ILCPA

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The present work describes the comparative study of the trans- and the cis-xylomollin structures. We have determined the two bridgehead H5 and H9 configurations using simulation calculations for both trans- and cis- distereoisomers. Molecular Dynamic (MD) simulations of the trans- and cis- xylomollin were performed with an efficient program. The geometries, interaction energies, bonds, angles, and the Van der Waals (VDW) interactions were carried out in solution and gas phases. This comparative study shows that the trans-xylomollin acquires the high configuration energy under the AMBER field using MD method. This molecule reaches its high stable configuration state in solution environment. Our MD simulation results are goods and in agreement with those of literature.

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Note Iridoid Glucosides, Phenylpropanoid Derivatives and Flavanoids from Bartsia alpina

Abstract: ABSTRACT

Cited by 6 publications

References 10 publications

Iridoid Glycosides Isolated from Bellardia trixago Identified as Inhibitors of Orobanche cumana Radicle Growth

Iridoid Glycosides Isolated from Bellardia trixago Identified as Inhibitors of Orobanche cumana Radicle Growth

Bartsia alpina L.

Studies of Trans- and Cis-Xylomollin Molecular Structures Using Molecular Dynamics Simulations

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