Niazirin

An antitumor promoter from Moringa oleifera Lam.[Pubmed:10209341]

Mutat Res. 1999 Apr 6;440(2):181-8.

In the course of studies on the isolation of bioactive compounds from Philippine plants, the seeds of Moringa oleifera Lam. were examined and from the ethanol extract were isolated the new O-ethyl-4-(alpha-L-rhamnosyloxy)benzyl carbamate (1) together with seven known compounds, 4(alpha-L-rhamnosyloxy)-benzyl isothiocyanate (2), niazimicin (3), Niazirin (4), beta-sitosterol (5), glycerol-1-(9-octadecanoate) (6), 3-O-(6'-O-oleoyl-beta-D-glucopyranosyl)-beta-sitosterol (7), and beta-sitosterol-3-O-beta-D-glucopyranoside (8). Four of the isolates (2, 3, 7, and 8), which were obtained in relatively good yields, were tested for their potential antitumor promoting activity using an in vitro assay which tested their inhibitory effects on Epstein-Barr virus-early antigen (EBV-EA) activation in Raji cells induced by the tumor promoter, 12-O-tetradecanoyl-phorbol-13-acetate (TPA). All the tested compounds showed inhibitory activity against EBV-EA activation, with compounds 2, 3 and 8 having shown very significant activities. Based on the in vitro results, niazimicin (3) was further subjected to in vivo test and found to have potent antitumor promoting activity in the two-stage carcinogenesis in mouse skin using 7,12-dimethylbenz(a)anthracene (DMBA) as initiator and TPA as tumor promoter. From these results, niazimicin (3) is proposed to be a potent chemo-preventive agent in chemical carcinogenesis.

Isolation and structure elucidation of new nitrile and mustard oil glycosides from Moringa oleifera and their effect on blood pressure.[Pubmed:7798960]

J Nat Prod. 1994 Sep;57(9):1256-61.

Bioassay-guided analysis of an EtOH extract of Moringa oleifera leaves showing hypotensive activity led to the isolation of two nitrile glycosides, Niazirin [1] and Niazirinin [2], and three mustard oil glycosides, 4-[(4'-O-acetyl-alpha-L-rhamnosyloxy)benzyl]isothiocyanate [4], niaziminin A, and niaziminin B. Glycoside 2 is a new compound. Niaziminins A and B have previously been obtained from the left extract as a mixture, while compound 4 is new from this source. Structural determination was accomplished by means of spectroscopic methods including appropriate 2D nmr experiments and chemical reactions. This is the first report of the isolation of nitriles, an isothiocyanate, and thiocarbamates from the same plant species. Isothiocyanate 4 and the thiocarbamate glycosides niaziminin A and B showed hypotensive activity while nitrile glycosides 1 and 2 were found to be inactive in this regard.

Effects of 2-azafluorenones on phosphatidyl-inositol specific phospholipase C activation in c6 glioma cells.[Pubmed:22559734]

Chin J Physiol. 2012 Apr 30;55(2):101-7.

The purpose of this study was to determine the effects of an extract from Moringa oleifera (MO) on the development of monocrotaline (MCT)-induced pulmonary hypertension (PH) in Wistar rats. An ethanol extraction was performed on dried MO leaves, and HPLC analysis identified niaziridin and Niazirin in the extract. PH was induced with a single subcutaneous injection of MCT (60 mg/kg) which resulted in increases in pulmonary arterial blood pressure (Ppa) and in thickening of the pulmonary arterial medial layer in the rats. Three weeks after induction, acute administration of the MO extract to the rats decreased Ppa in a dose-dependent manner that reached statistical significance at a dose of 4.5 mg of freeze-dried extract per kg body weight. The reduction in Ppa suggested that the extract directly relaxed the pulmonary arteries. To assay the effects of chronic administration of the MO extract on PH, control, MCT and MCT+MO groups were designated. Rats in the control group received a saline injection; the MCT and MCT+MO groups received MCT to induce PH. During the third week after MCT treatment, the MCT+MO group received daily i.p. injections of the MO extract (4.5 mg of freeze-dried extract/kg of body weight). Compared to the control group, the MCT group had higher Ppa and thicker medial layers in the pulmonary arteries. Chronic treatments with the MO extract reversed the MCT-induced changes. Additionally, the MCT group had a significant elevation in superoxide dismutase activity when normalized by the MO extract treatments. In conclusion, the MO extract successfully attenuated the development of PH via direct vasodilatation and a potential increase in antioxidant activity.

Unusual glycosides of pyrrole alkaloid and 4'-hydroxyphenylethanamide from leaves of Moringa oleifera.[Pubmed:21439596]

Phytochemistry. 2011 Jun;72(8):791-5.

Glycosides of pyrrole alkaloid (pyrrolemarumine 4''-O-alpha-L-rhamnopyranoside) and 4'-hydroxyphenylethanamide (marumosides A and B) were isolated from leaves of Moringa oleifera along with eight known compounds; Niazirin, methyl 4-(alpha-L-rhamnopyranosyloxy)benzylcarbamate, benzyl beta-D-glucopyranoside, benzyl beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside, kaempferol 3-O-beta-D-glucopyranoside, quercetin 3-O-beta-D-glucopyranoside, adenosine and L-tryptophan. Structure elucidations were based on analyses of chemical and spectroscopic data including 1D- and 2D-NMR.

Review: an exposition of medicinal preponderance of Moringa oleifera (Lank.).[Pubmed:24577932]

Pak J Pharm Sci. 2014 Mar;27(2):397-403.

Medicinal plants are believed to be a precious natural reservoir as they are assumed to have paranormal effects for the mankind. Moringa oleifera grows throughout most of the tropics and has numerous industrial and medicinal uses. This review acquaints with the consequence of fera (Moringaceae), a fast growing medicinal plant wide spread in tropical regions with height ranging from 5-10m. It has an enormous nutritional worth due to existence of vitamins and proteins. It is subsisted with many constituents. Its oil consists of oleic, tocopherols, stearic, palmitic, behenic and arachidic acid. Flavanoids and phenolics such as gallic acid, chlorogenic acid, ferulic acid, kaempferol, ellagic acid, quercetin and vanillin are present by means of leaf extract, being richest in phenolics and subsequent fruit and seed extract respectively, that are accountable for antioxidant activity of plant. Seeds have been pragmatic with active components as novel O-ethyl-4- (alpha -L-rhamnosyloxy) benzyl carbamate together with seven known compounds, 4 (alpha -L-rhamnosyloxy)-benzyl isothiocyanate, niazimicin, Niazirin, beta-sitosterol, glycerol-1- (9 -octadecanoate), 3 -O- 6 -O-oleoyl- beta -D-glucopyranosyl-b-sitosterol, and beta - sitosterol- 3-X-O -beta -D-glucopyranoside , that have been discerned to inhibit EBV-EA (Epstein- Barr virus-early antigen), that is persuaded by the cancer promoter. M. oleifera leaves, gums, roots, flowers as well as kernels have been unanimously utilized for managing tissue tenderness, cardiovascular and liver maladies, normalize blood glucose and cholesterol. It has also profound antimicrobial, hypoglycemic and anti-tubercular activities.

Attenuation of the extract from Moringa oleifera on monocrotaline-induced pulmonary hypertension in rats.[Pubmed:22242951]

Chin J Physiol. 2012 Feb 29;55(1):22-30.

The purpose of this study was to determine the effects of an extract from Moringa oleifera (MO) on the development of monocrotaline (MCT)-induced pulmonary hypertension (PH) in Wistar rats. An ethanol extraction was performed on dried MO leaves, and HPLC analysis identified niaziridin and Niazirin in the extract. PH was induced with a single subcutaneous injection of MCT (60 mg/kg) which resulted in increases in pulmonary arterial blood pressure (Ppa) and in thickening of the pulmonary arterial medial layer in the rats. Three weeks after induction, acute administration of the MO extract to the rats decreased Ppa in a dose-dependent manner that reached statistical significance at a dose of 4.5 mg of freeze-dried extract per kg body weight. The reduction in Ppa suggested that the extract directly relaxed the pulmonary arteries. To assay the effects of chronic administration of the MO extract on PH, control, MCT and MCT+MO groups were designated. Rats in the control group received a saline injection; the MCT and MCT+MO groups received MCT to induce PH. During the third week after MCT treatment, the MCT+MO group received daily i.p. injections of the MO extract (4.5 mg of freeze-dried extract/kg of body weight). Compared to the control group, the MCT group had higher Ppa and thicker medial layers in the pulmonary arteries. Chronic treatments with the MO extract reversed the MCT-induced changes. Additionally, the MCT group had a significant elevation in superoxide dismutase activity when normalized by the MO extract treatments. In conclusion, the MO extract successfully attenuated the development of PH via direct vasodilatation and a potential increase in antioxidant activity.

[Constituents isolated from n-butanol extract of leaves of Moringa oleifera].[Pubmed:29552820]

Zhongguo Zhong Yao Za Zhi. 2018 Jan;43(1):114-118.

Seventeen compounds were isolated from n-butanol extract of the leaves of Moringa oleifera, using column chromatography over macroporous resin HP-20,Sephadex LH-20, and ODS. Their structures were identified as two carboline,tangutorid E(1) and tangutorid F(2); three phenolic glycosides,Niazirin(3)benzaldehyde 4-O-alpha-L-rhamnopyranoside(4) and 4-O-beta-D-glucopyranosidebenzoic acid(5); four chlorogenic acid and derivatives,4-caffeoylquinic acid(6),methyl 4-caffeoylquinate(7),caffeoylquinic acid(8) and methyl caffeoylquinate(9); two nucleosids,uridine(10) and adenosine(11); one flavone,quercetin 3-O-beta-D-glucopyranoside(12); five other types of compounds,phthalimidineacetic acid(13),3-pyridinecarboxamide(14),3,4-dihydroxy-benzoic acid(15),5-hydroxymethyl-2-furancarboxylic acid(16) and 5-hydroxymethyl-2-furaldehyde(17) by the spectral data of (1)H, (1)(3)C-NMR and MS. Among them,compounds 1-2,7,9-10,16 and 17 were isolated from M. oleifera for the first time.