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Fulltext Neonaucline, a new indole alkaloid from the leaves of Ochreinauclea maingayii (Hook. f.) Ridsd. (Rubiaceae)

Muktar MR, Osman N, Awang K, Hazni H, Qureshi AK, Hadi AH, et al.

Molecules, 2011 Dec 28;17(1):267-74.

PMID: 22205092 DOI: 10.3390/molecules17010267

A new indole alkaloid; neonaucline (1), along with six known compounds-Cadamine (2), naucledine (3), harmane, benzamide, cinnamide and blumenol A-were isolated from the leaves of Ochreinauclea maingayii (Rubiaceae). In addition to that of compound 1, (13)C-NMR data of cadamine (2) and naucledine (3) were also reported. Structural elucidations of these alkaloids were performed using spectroscopic methods especially 1D- and 2D-NMR, IR, UV and LCMS-IT-TOF. The excellent vasorelaxant activity on isolated rat aorta was observed for the alkaloids 1-3 after injection of each sample at 1 × 10(-5) M.

Matched MeSH terms: Vasodilator Agents/isolation & purification

Fulltext Naucline, a new indole alkaloid from the bark of Nauclea officinalis

Liew SY, Mukhtar MR, Hadi AH, Awang K, Mustafa MR, Zaima K, et al.

Molecules, 2012 Apr 02;17(4):4028-36.

PMID: 22469596 DOI: 10.3390/molecules17044028

A new indole alkaloid, naucline (1) together with four known alkaloids, angustine (2), angustidine (3), nauclefine (4) and naucletine (5), were isolated from the bark of Nauclea officinalis. The structures of all isolated compounds were elucidated with various spectroscopic methods such as 1D- and 2D- NMR, IR, UV and LCMS-IT-TOF. In addition to that of alkaloid 1, the complete 13C-NMR data of naucletine (5) were also reported. Naucline (1) showed a moderate vasorelaxant activity (90% relaxation at 1 × 10(-5) M) whereas, angustine (2), nauclefine (4), and naucletine (5) showed potent vasorelaxant activity (more than 90% relaxation at 1 × 10(-5) M) on an isolated rat aorta.

Matched MeSH terms: Vasodilator Agents/isolation & purification

Vasorelaxation induced by common edible tropical plant extracts in isolated rat aorta and mesenteric vascular bed

Runnie I, Salleh MN, Mohamed S, Head RJ, Abeywardena MY

J Ethnopharmacol, 2004 Jun;92(2-3):311-6.

PMID: 15138017

In this study, the vasodilatory actions of nine edible tropical plant extracts were investigated. Ipomoea batatas (sweet potato leaf), Piper betle (betel leaf), Anacardium occidentale (cashew leaf), Gynandropsis gynandra (maman leaf), Carica papaya (papaya leaf), and Mentha arvensis (mint leaf) extracts exhibited more than 50% relaxing effect on aortic ring preparations, while Piper betle and Cymbopogon citratus (lemongrass stalk) showed comparable vasorelaxation on isolated perfused mesenteric artery preparation. The vascular effect on the aortic ring preparations were mainly endothelium-dependent, and mediated by nitric oxide (NO) as supported by the inhibition of action in the presence of N(omega)-nitro-L-arginine (NOLA), an nitric oxide synthase (NOS) inhibitor, or by the removal of endothelium. In contrast, vasodilatory actions in resistance vessels (perfused mesenteric vascular beds) appear to involve several biochemical mediators, including NO, prostanoids, and endothelium-dependent hyperpolarizing factors (EDHFs). Total phenolic contents and antioxidant capacities varied among different extracts and found to be independent of vascular relaxation effects. This study demonstrates that many edible plants common in Asian diets to possess potential health benefits, affording protection at the vascular endothelium level.

Matched MeSH terms: Vasodilator Agents/isolation & purification

Calofolic acids A-F, chromanones from the bark of Calophyllum scriblitifolium with vasorelaxation activity

Nugroho AE, Sasaki T, Kaneda T, Hadi AHA, Morita H

Bioorg Med Chem Lett, 2017 May 15;27(10):2124-2128.

PMID: 28389148 DOI: 10.1016/j.bmcl.2017.03.071

Vasorelaxation activity guided separation of the methanol extract of Calophyllum scriblitifolium bark led to the isolation of 6 chromanones (calofolic acids A-F, 1-6). Their structures were elucidated by 1D and 2D NMR spectroscopy, and their absolute configurations were investigated by a combination of CD spectroscopy and DFT calculation. All isolated chromanones showed dose-dependent vasorelaxation activity on isolated rat aorta.

Matched MeSH terms: Vasodilator Agents/isolation & purification

Fulltext Vasorelaxant properties of Vernonia amygdalina ethanol extract and its possible mechanism

Ch'ng YS, Loh YC, Tan CS, Ahmad M, Asmawi MZ, Wan Omar WM, et al.

Pharm Biol, 2017 Dec;55(1):2083-2094.

PMID: 28832263 DOI: 10.1080/13880209.2017.1357735

CONTEXT: Vernonia amygdalina Del. (VA) (Asteraceae) is commonly used to treat hypertension in Malaysia.

OBJECTIVE: This study investigates the vasorelaxant mechanism of VA ethanol extract (VAE) and analyzes its tri-step FTIR spectroscopy fingerprint.

MATERIALS AND METHODS: Dried VA leaves were extracted with ethanol through maceration and concentrated using rotary evaporator before freeze-dried. The vasorelaxant activity and the underlying mechanisms of VAE using the cumulative concentration (0.01-2.55 mg/mL at 20-min intervals) were evaluated on aortic rings isolated from Sprague Dawley rats in the presence of antagonists.

RESULTS: The tri-step FTIR spectroscopy showed that VAE contains alkaloids, flavonoids, and saponins. VAE caused the relaxation of pre-contracted aortic rings in the presence and absence of endothelium with EC50 of 0.057 ± 0.006 and 0.430 ± 0.196 mg/mL, respectively. In the presence of Nω-nitro-l-arginine methyl ester (EC50 0.971 ± 0.459 mg/mL), methylene blue (EC50 1.203 ± 0.426 mg/mL), indomethacin (EC50 2.128 ± 1.218 mg/mL), atropine (EC50 0.470 ± 0.325 mg/mL), and propranolol (EC50 0.314 ± 0.032 mg/mL), relaxation stimulated by VAE was significantly reduced. VAE acted on potassium channels, with its vasorelaxation effects significantly reduced by tetraethylammonium, 4-aminopyridine, barium chloride, and glibenclamide (EC50 0.548 ± 0.184, 0.158 ± 0.012, 0.847 ± 0.342, and 0.304 ± 0.075 mg/mL, respectively). VAE was also found to be active in reducing Ca2+ released from the sarcoplasmic reticulum and blocking calcium channels.

CONCLUSIONS: The vasorelaxation effect of VAE involves upregulation of NO/cGMP and PGI2 signalling pathways, and modulation of calcium/potassium channels, and muscarinic and β2-adrenergic receptor levels.

Matched MeSH terms: Vasodilator Agents/isolation & purification

Hispidacine, an unusual 8,4'-oxyneolignan-alkaloid with vasorelaxant activity, and hispiloscine, an antiproliferative phenanthroindolizidine alkaloid, from Ficus hispida Linn

Yap VA, Loong BJ, Ting KN, Loh SH, Yong KT, Low YY, et al.

Phytochemistry, 2015 Jan;109:96-102.

PMID: 25468714 DOI: 10.1016/j.phytochem.2014.10.032

Hispidacine, an 8,4'-oxyneolignan featuring incorporation of an unusual 2-hydroxyethylamine moiety at C-7, and hispiloscine, a phenanthroindolizidine alkaloid, were isolated from the stem-bark and leaves of the Malaysian Ficus hispida Linn. Their structures were established by spectroscopic analysis. Hispidacine induced a moderate vasorelaxant activity in rat isolated aorta, while hispiloscine showed appreciable antiproliferative activities against MDA-MB-231, MCF-7, A549, HCT-116 and MRC-5 cell lines.

Matched MeSH terms: Vasodilator Agents/isolation & purification

Oppositinines A and B: new vasorelaxant beta-carboline alkaloids from Neisosperma oppositifolia

Ahmad K, Thomas NF, Hadi AH, Mukhtar MR, Mohamad K, Nafiah MA, et al.

Chem Pharm Bull (Tokyo), 2010 Aug;58(8):1085-7.

PMID: 20686264

A phytochemical study on the bark of Neisosperma oppositifolia (Apocynaceae) yielded two new beta-carboline indole alkaloids, oppositinines A (1) and B (2), together with five known alkaloids, isoreserpiline, isocarapanaubine, vobasine, 10-methoxydihydrocorynantheol-N-oxide, and ochropposinine oxindole. Structural elucidation of 1 and 2 was performed using 2D NMR methods. Oppositinines A (1) and B (2) showed potent vasorelaxant effects on the rat aorta.

Matched MeSH terms: Vasodilator Agents/isolation & purification

Vasodilator effect of Phlomis bracteosa constituents is mediated through dual endothelium-dependent and endothelium-independent pathways

Khan AU, Ullah R, Khan A, Mustafa MR, Hussain J, Murugan DD, et al.

Clin Exp Hypertens, 2012;34(2):132-9.

PMID: 21967029 DOI: 10.3109/10641963.2011.601383

This study describes the vasorelaxant potential of some pure compounds isolated from Phlomis bracteosa L. marrubiin, phlomeoic acid, and two new constituents labeled as RA and RB. In rat thoracic aortic rings denuded of endothelium, marrubiin, phlomeoic acid, RA, and RB caused relaxation of high K(+) (80 mM) and phenylephrine (1 μM)-induced contractions at the concentration range of 1.0-1000 μg/mL. Marrubiin, phlomeoic acid, RA, and RB concentration dependently (3.0-10 μg/mL) shifted the Ca(++) curves to the right obtained in Ca(++)-free medium. The vasodilator effect of marrubiin, phlomeoic acid, RA, and RB was partially blocked by N(ω)-nitro-L-arginine methyl ester in endothelium-intact aorta preparations. These results reveal that P. bracteosa constituents: marrubiin, phlomeoic acid, RA, and RB exhibit vasodilator action occurred via a combination of endothelium-independent Ca(++) antagonism and endothelium-dependent N(ω)-nitro-L-arginine methyl ester-sensitive nitric oxide-modulating mechanism.

Matched MeSH terms: Vasodilator Agents/isolation & purification

Bisnicalaterines B and C, atropisomeric bisindole alkaloids from Hunteria zeylanica, showing vasorelaxant activity

Hirasawa Y, Hara M, Nugroho AE, Sugai M, Zaima K, Kawahara N, et al.

J Org Chem, 2010 Jun 18;75(12):4218-23.

PMID: 20469917 DOI: 10.1021/jo1006762

Two new bisindole alkaloids, bisnicalaterines B and C (1 and 2) consisting of an eburnane and a corynanthe type of skeletons, were isolated from the bark of Hunteria zeylanica. Their absolute structures were determined by combination of NMR, CD, and computational methods, and each of them was shown to be in an atropisomeric relationship. Bisnicalaterines B and C (1 and 2) showed potent vasorelaxant activity on isolated rat aorta.

Matched MeSH terms: Vasodilator Agents/isolation & purification

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