Triterpenoids in lipophilic leaf and stem coatings

Wollenweber, Eckhard; Doerr, Marion; Siems, Karsten; Faure, Robert; Bombarda, Isabelle; Gaydou, Émile M.

doi:10.1016/s0305-1978(98)00070-2

Cited by 18 publications

(16 citation statements)

References 5 publications

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“…They have been reported for their antiinflammatory (Altavilla et al, 2008;De-Melo et al, 2005), antinociceptive, antioxidant (Bonina et al, 2000;Thuong et al, 2007), hepatoprotective, and antitumor effects (Camargo et al, 2002;Jung et al, 2008;Kang et al, 2000;Torres et al, 2003). Phenolic acids and flavonoids (Korul'kin, 2001;Mulinacci et al, 1995;Stevens et al, 1994;Wolbis, 1987Wolbis, , 1989a, coumarins (Wolbis & Krolikowska, 1988;Zaitsev et al, 1983), terpenes (He et al, 1998;Wollenweber et al, 1999), and alkaloids (Colau & Hootele, 1983;Kim et al, 1996) have been isolated from Sedum species.…”

Section: Introductionmentioning

confidence: 99%

Compounds fromSedum caeruleumwith antioxidant, anticholinesterase, and antibacterial activities

Bensouici

Kabouche

Karioti

et al. 2015

Pharmaceutical Biology

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Context: This is the first study on the phytochemistry, antioxidant, anticholinesterase, and antibacterial activities of Sedum caeruleum L. (Crassulaceae). Objective: The objective of this study is to isolate the secondary metabolites and determine the antioxidant, anticholinesterase, and antibacterial activities of S. caeruleum. Materials and methods: Six compounds (1-6) were isolated from the extracts of S. caeruleum and elucidated using UV, 1D-, 2D-NMR, and MS techniques. Antioxidant activity was investigated using DPPH , CUPRAC, and ferrous-ions chelating assays. Anticholinesterase activity was determined against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes using the Ellman method. Antibacterial activity was performed according to disc diffusion and minimum inhibitory concentration (MIC) methods. Results: Isolated compounds were elucidated as ursolic acid (1), daucosterol (2), b-sitosterol-3-O-b-D-galactopyranoside (3), apigenin (4), apigetrin (5), and apiin (6). The butanol extract exhibited highest antioxidant activity in all tests (IC 50 value: 28.35 ± 1.22 mg/mL in DPPH assay, IC 50 value: 40.83 ± 2.24 mg/L in metal chelating activity, and IC 50 value: 23.52 ± 0.44 mg/L in CUPRAC), and the highest BChE inhibitory activity (IC 50 value: 36.89 ± 0.15 mg/L). Moreover, the chloroform extract mildly inhibited (MIC value: 80 mg/mL) the growth of all the tested bacterial strains. Discussion and conclusion: Ursolic acid (1), daucosterol (2), b-sitosterol-3-O-b-D-galactopyranoside (3), apigenin (4), apigetrin (5), and apiin (6) were isolated from Sedum caeruleum for the first time. In addition, a correlation was observed between antioxidant and anticholinesterase activities of bioactive ingredients of this plant.

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Section: Introductionmentioning

confidence: 99%

Compounds fromSedum caeruleumwith antioxidant, anticholinesterase, and antibacterial activities

Bensouici

Kabouche

Karioti

et al. 2015

Pharmaceutical Biology

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“…2007), a group of secondary metabolites derived from squalene and thus characterized by structures containing 30 carbon atoms. The cuticular triterpenoid fraction of most plant species is dominated by lupeol, α ‐amyrin and/or β ‐amyrin (Hemmers, Gülz & Marner 1988; Wollenweber et al. 1999; Guhling et al.…”

Section: Introductionmentioning

confidence: 99%

Development of the cuticular wax during growth of Kalanchoe daigremontiana (Hamet et Perr. de la Bathie) leaves

Maarseveen

Han

Jetter

2008

Plant Cell & Environment

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The goal of the present study was to monitor cuticular wax accumulation during leaf development of Kalanchoe daigremontiana. Leaves expanded linearly until they were 40-60 d old. Wax coverages of leaves on the third node increased steadily during initial leaf development, from 6.5 mg·cm -2 on day 22 to 15.3 mg·cm -2 on day 53, and then levelled off. Triterpenoids dominated the wax mixture throughout leaf development, but decreased from 74 to 40-45% in mature leaves, while very long-chain fatty acid (VLCFA) derivatives increased from 19 to 39-44%. The major VLCFA derivatives were alkanes, accompanied by fatty acids, primary alcohols, aldehydes and alkyl esters. In all compound classes, either C34 or C33 homologs predominated during leaf development. Eight different triterpenoids were identified, with glutinol constituting 70% of the fraction, and friedelin (20%) and germanicol (10%) as further major components of the young leaf wax. The glutinol percentage decreased, while the relative amounts of epifriedelanol and glutanol increased during development. Various leaf pairs upwards from the third node showed similar growth patterns and developmental time courses of cuticular wax amounts and composition. Based on these surface chemical analyses, the relative activities of biosynthetic pathways leading to various wax components can be assessed.

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“…The structures of the five known compounds were identified as R-amyrin palmitate (3), β-amyrin palmitate (4), β-amyrin acetate (5), lupeyl acetate (6), and lupeol (7), by comparison of their spectral data with values reported in the literature. [9][10][11] In this paper we report the structure elucidation of the two new triterpene fatty esters, kairatenyl palmitate (1) and hopenyl palmitate (2). Kairatenyl palmitate (1) was obtained as a colorless viscous liquid and was shown to have the molecular formula C 46 H 80 O 2 by HRFABMS, 13 C NMR, and DEPT spectra; this composition indicated seven degrees of unsaturation.…”

mentioning

confidence: 99%

Two New Triterpene Esters from the Twigs of Brachylaena ramiflora from the Madagascar Rainforest

Chaturvedula¹,

Schilling²,

Miller³

et al. 2002

J. Nat. Prod.

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Bioassay-guided fractionation of a CH(2)Cl(2)/MeOH extract of the small twigs of Brachylaena ramiflora var. ramiflora resulted in the isolation of the two new triterpene esters 1 and 2 and five known triterpenoids, alpha-amyrin palmitate (3), beta-amyrin palmitate (4), beta-amyrin acetate (5), lupeyl acetate (6), and lupeol (7). The structures of the two new compounds were established as kairatenyl palmitate (1) and hopenyl palmitate (2) on the basis of 1D and 2D NMR spectroscopic data interpretation and chemical conversions. All the isolated compounds showed weak cytotoxicity against the A2780 human ovarian cancer cell line.

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Triterpenoids in lipophilic leaf and stem coatings

Cited by 18 publications

References 5 publications

Compounds fromSedum caeruleumwith antioxidant, anticholinesterase, and antibacterial activities

Compounds fromSedum caeruleumwith antioxidant, anticholinesterase, and antibacterial activities

Development of the cuticular wax during growth of Kalanchoe daigremontiana (Hamet et Perr. de la Bathie) leaves

Two New Triterpene Esters from the Twigs of Brachylaena ramiflora from the Madagascar Rainforest

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