Limonoid derivatives from Cedrelopsis grevei

Mulholland, Dulcie A.; Mahomed, Hamdani; Kotsos, Maria; Randrianarivelojosia, Milijaona; Lavaud, Catherine; Massiot, Georges

doi:10.1016/s0040-4020(99)00653-5

Cited by 30 publications

(26 citation statements)

References 5 publications

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“…NMR spectra were recorded on a Bruker AC 200 Fourier Transform spectrometer operating at 50.323 MHz for 13 C, equipped with a 10 mm (or 5 mm) probe; 200 mg (or 70 mg) of the oil in 2 ml (or 0.5 ml) CDCl 3 . Other parameters were as previously reported.…”

Section: Carbon-13 Nmrmentioning

confidence: 99%

Composition and chemical variability of the bark oil of Cedrelopsis grevei H. Baillon from Madagascar

Cavalli

Tomi

Bernardini

et al. 2003

Flavour & Fragrance J

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A commercial sample of Cedrelopsis grevei H. Baillon from Madagascar was repeatedly chromatographed and the combined analysis of all the fractions by GC, GC-MS and 13 C-NMR led to the identification of 114 components. The major constituents were (E)-β-caryophyllene (9.3%), α-copaene (7.7%), α-selinene (5.8%), δ-cadinene (4.9%), β-selinene (4.5%), α-humulene (3.3%) and β-bisabolene (2.8%). Analysis of five other commercial samples confirmed the pre-eminence of sesquiterpene hydrocarbons and exhibited a variation in the contents of the main components: ishwarane (1.0-17.4%), (E)-β-caryophyllene (1.3-12.5%), α-copaene (4.9-11.0%), β-elemene (0.2-9.6%) and α-selinene (1.1-9.4%).

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Section: Carbon-13 Nmrmentioning

confidence: 99%

Composition and chemical variability of the bark oil of Cedrelopsis grevei H. Baillon from Madagascar

Cavalli

Tomi

Bernardini

et al. 2003

Flavour & Fragrance J

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“…blood pressure; vasoconstriction CEDRELOPSIS GREVEI (CG) Baill (Meliaceae) is an endemic plant from the southern and western areas of Madagascar empirically used against pulmonary diseases such as cough, tuberculosis, and pneumonia. This plant is also used as an antiasthenic, anti-inflammatory, and antihypertensive drug (4, 5, 10).Different classes of compounds have been isolated from CG including chromones, coumarins, triterpenoids, limonoids, and polyphenols (9,13,20,27). These compounds are known to be biologically active and beneficial against different pathologies such as inflammation, cancer, and cardiovascular diseases (15,19).…”

mentioning

confidence: 99%

“…Different classes of compounds have been isolated from CG including chromones, coumarins, triterpenoids, limonoids, and polyphenols (9,13,20,27). These compounds are known to be biologically active and beneficial against different pathologies such as inflammation, cancer, and cardiovascular diseases (15,19).…”

mentioning

confidence: 99%

Cedrelopsis grevei induced hypotension and improved endothelial vasodilatation through an increase of Cu/Zn SOD protein expression

Ranaivo¹,

Rakotoarison²,

Tesse³

et al. 2004

American Journal of Physiology-Heart and Circulatory Physiology

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. Cedrelopsis grevei induced hypotension and improved endothelial vasodilatation through an increase of Cu/Zn SOD protein expression. Am J Physiol Heart Circ Physiol 286: H775-H781, 2004. First published November 6, 2003 10.1152/ajpheart.00584.2003.-This study was designed to investigate the cardiovascular consequences of oral administration of Cedrelopsis grevei (CG) in normotensive rats. Experiments were designed to investigate hemodynamic parameters in vivo as well as the consequences of CG treatment on the vasoconstriction response to norepinephrine and the vasorelaxant response to ACh ex vivo in isolated aortas and small mesenteric arteries (SMA). Treatment of male Wistar rats with 80 mg/kg CG for 4 wk induced a progressive decrease in systolic blood pressure. In the aorta, CG did not significantly alter the response to norepinephrine despite the participation of extraendothelial nitric oxide (NO)-induced hyporeactivity. In the SMA, contraction to norepinephrine was not modified by CG treatment even though it enhanced the participation of endothelial NO. Endothelium-dependent relaxation to ACh was increased in both the aorta and SMA from CG-treated rats. In the aorta from CG-treated rats, the mechanism involved superoxide dismutase (SOD)-and catalase-sensitive free radical production. The latter was associated with enhanced expression of Cu/Zn SOD and endothelial NO synthase. These results suggest that oral administration of CG produces a decrease in blood pressure in normotensive rats. This hemodynamic effect was associated with enhanced endothelium-dependent relaxation and an induction of Cu/Zn SOD and endothelial NO synthase expressions in the vessel wall. They also show subtle mechanisms that compensate for the increased participation of NO to maintain unchanged agonistinduced contractility. These data provide a pharmacological basis for the empirical use of CG against cardiovascular diseases. blood pressure; vasoconstriction CEDRELOPSIS GREVEI (CG) Baill (Meliaceae) is an endemic plant from the southern and western areas of Madagascar empirically used against pulmonary diseases such as cough, tuberculosis, and pneumonia. This plant is also used as an antiasthenic, anti-inflammatory, and antihypertensive drug (4, 5, 10).Different classes of compounds have been isolated from CG including chromones, coumarins, triterpenoids, limonoids, and polyphenols (9,13,20,27). These compounds are known to be biologically active and beneficial against different pathologies such as inflammation, cancer, and cardiovascular diseases (15,19). Among these compounds, the most active are the molecules from the class of polyphenols and coumarins. Indeed, they have been reported to scavenge reactive oxygen species (ROS), inhibit oxidation of low-density lipoprotein, prevent platelet aggregation, induce vasorelaxation, and interact with the nitric oxide (NO) pathway (1,2,14,16,22,23).Very recently, we reported that a crude extract of CG was able to induce relaxation of the rat aorta in both the presence or absence of functiona...

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“…Recently, some close structural relatives of the cneorins, the cedkathryns (4), were isolated from Cedrelopsis gracilis from Madagascar ( Figure 1). 4 In addition, some compounds that could result from rearrangements of the cneorins or the tricoccins, for example cedmilinol (5), have been isolated from Cedrelopsis grevei. 5 …”

Section: Introductionmentioning

confidence: 99%

Synthesis of DEFG ring system of cneorins

Koskinen¹,

Pihko²

2009

Arkivoc

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The cneorins have been isolated from the xerophytic shrub Cneorum pulverulentum, which is native to the Canary Islands. They are natural products containing a [4.3.1]propellane ring system (DEFG rings) as the northern part of the molecule and a 5,5-spiroketal unit and a butenolide moiety (A ring) as the southern part. The synthesis of the DEFG ring system of the cneorins is described. The key steps include: intramolecular cyclopropanation of a diazomalonate providing the EFG ring fragment and an anionic cyclization of a sulfone yielding the [4.3.1]propellane ring system.

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Limonoid derivatives from Cedrelopsis grevei

Cited by 30 publications

References 5 publications

Composition and chemical variability of the bark oil of Cedrelopsis grevei H. Baillon from Madagascar

Composition and chemical variability of the bark oil of Cedrelopsis grevei H. Baillon from Madagascar

Cedrelopsis grevei induced hypotension and improved endothelial vasodilatation through an increase of Cu/Zn SOD protein expression

Synthesis of DEFG ring system of cneorins

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