Ehretinine, a novel pyrrolizidine alkaloid from Ehretia aspera

Suri, O. P.; Jamwal, R. S.; Suri, K. A.; Atal, C.K.

doi:10.1016/0031-9422(80)83115-3

Cited by 16 publications

(7 citation statements)

References 1 publication

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“…This unusual necine base is found for instance in laburnamine, an alkaloid present in trace amounts in Laburnum anagyroides [18]. From the leaves of Ehretia asperia, ehretinine was isolated, which is very unusual since the 7-hydroxy group of its necine base, (1 R ,7 S )-7-methylhexahydro-1 H -pyrrolizin-1-ol, is esterified with 4-methylbenzoic acid and the typical hydroxymethyl group on C-1 is replaced by a methyl residue [19]. Similarly, Senecio polypodioides contains, besides sarracine N -oxide, also 7β-angeloyloxy-1-methylene-8α-pyrrolizidine, a PA with a methylene group instead of the typical hydroxymethyl residue on its necine base.…”

Section: Structural Diversity Of Pyrrolizidine Alkaloidsmentioning

confidence: 99%

Pyrrolizidine Alkaloids: Biosynthesis, Biological Activities and Occurrence in Crop Plants

2019

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Pyrrolizidine alkaloids (PAs) are heterocyclic secondary metabolites with a typical pyrrolizidine motif predominantly produced by plants as defense chemicals against herbivores. They display a wide structural diversity and occur in a vast number of species with novel structures and occurrences continuously being discovered. These alkaloids exhibit strong hepatotoxic, genotoxic, cytotoxic, tumorigenic, and neurotoxic activities, and thereby pose a serious threat to the health of humans since they are known contaminants of foods including grain, milk, honey, and eggs, as well as plant derived pharmaceuticals and food supplements. Livestock and fodder can be affected due to PA-containing plants on pastures and fields. Despite their importance as toxic contaminants of agricultural products, there is limited knowledge about their biosynthesis. While the intermediates were well defined by feeding experiments, only one enzyme involved in PA biosynthesis has been characterized so far, the homospermidine synthase catalyzing the first committed step in PA biosynthesis. This review gives an overview about structural diversity of PAs, biosynthetic pathways of necine base, and necic acid formation and how PA accumulation is regulated. Furthermore, we discuss their role in plant ecology and their modes of toxicity towards humans and animals. Finally, several examples of PA-producing crop plants are discussed.

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Section: Structural Diversity Of Pyrrolizidine Alkaloidsmentioning

confidence: 99%

Pyrrolizidine Alkaloids: Biosynthesis, Biological Activities and Occurrence in Crop Plants

2019

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“…Traditionally, it has been used fever, sores on tongue, dysentery and many more health ailments 14,15 . Some species of the Ehretia genus are used for medical purposes However, many species include phytochemicals alkaloids 16,17 , flavonoids 18,19,20 , fatty acids 21 , which are responsible for antioxidant 22,23 , anti-inflammatory 24,25 , anti-allergic 26,27 , antibacterial 28,29 activities in different species like E. laevis, E. tinifolia, E. microphylla, E. longiflora, E. obtusifolia.…”

Section: Introductionmentioning

confidence: 99%

COMPARATIVE EVALUATIONOF ABTS, DPPH, FRAP, NITRIC OXIDE ASSAYS FOR ANTIOXIDANT POTENTIAL, PHENOLIC & FLAVONOID CONTENT OF EHRETIA ACUMINATA R. BR. BARK

Kaur¹,

Shukla²,

Shukla³

2019

Int. Res. J. Pharm.

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Barks extracts of traditionally important medicinal plant, Ehretia acuminata R. Br. was screened for their free radical scavenging properties using ascorbic acid (A.A) and gallic acid (G.A) as standard antioxidant. Free radical scavenging activity was evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, 2,2′-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid (ABTS), Ferric oxide reducing assay (FRAP) and nitric oxide assay. There were positive correlations between antioxidant activity assessed by ABTS, DPPH, FRAP & Nitric oxide, between Total Phenolic and flavonoids content with all methods using five extract Petroleum ether (P.E), chloroform (CH), ethyl acetate (E.A), ethanol (EOL) & water (WTR). The overall antioxidant activity of bark was the strongest in ethyl acetate and weakest in water extract. The IC50 of the ethyl acetate extracts ranged between 22 and 140 μg/ml and that of ascorbic acid was 28 μg/ml. The study reveals that the consumption of this plant would exert several beneficial effects by virtue of their antioxidant activity.

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“…1) and thiamine pyrophosphate (TPP, a coenzyme that is part of the Krebs cycle in the process of cellular respiration). [7][8][9][10][11][12] Furthermore, there are many other applications of thiazole derivatives, for example in liquid crystals or cosmetics (sunscreens). Thiazole derivatives display a wide range of biological activities, such as cardiotonic, fungicidal, sedative, anesthetic, bactericidal and anti--inflammatory.…”

Section: Introductionmentioning

confidence: 99%

Novel one-pot process for the synthesis of ethyl 2-imino-4-methyl-2,3-dihydrothiazole-5-carboxylates

Beyzaei

Aryan

Moghadas

2015

JSCS

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A facile one-pot, two-step process for the synthesis of ethyl 2-imino--4-methyl-2,3-dihydrothiazole-5-carboxylates via the cyclocondensation of ethyl 3-oxo-2-thiocyanatobutanoate with a variety of hydrazine and hydrazide derivatives was developed. Ethyl 3-oxo-2-thiocyanatobutanoate itself was synthesized as an intermediate from the reaction of ethyl 2-chloroacetoacetate with potassium thiocyanate (KSCN). The molecular structures of these newly synthesized compounds were elucidated based on elemental analysis and spectral data.Развијен је нов поступак синтезе етил-2-имино-4-метил-2,3-дихидротиазол-5-карбоксилата, у једном реакционом кораку циклокондензације етил-3-оксо-2-тиоцијанатобутаноата и хидразина или хидразинских деривата. Полазно једињење етил-3-оксо-2--тиоцијанатобутаноат синтетисан је из етил-2-хлорацетата и калијум-тиоцијаната (KSCN). Структура добијених једињења одређена је на основу резултата спектроскопске и елементалне анализе.

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Ehretinine, a novel pyrrolizidine alkaloid from Ehretia aspera

Cited by 16 publications

References 1 publication

Pyrrolizidine Alkaloids: Biosynthesis, Biological Activities and Occurrence in Crop Plants

Pyrrolizidine Alkaloids: Biosynthesis, Biological Activities and Occurrence in Crop Plants

COMPARATIVE EVALUATIONOF ABTS, DPPH, FRAP, NITRIC OXIDE ASSAYS FOR ANTIOXIDANT POTENTIAL, PHENOLIC & FLAVONOID CONTENT OF EHRETIA ACUMINATA R. BR. BARK

Novel one-pot process for the synthesis of ethyl 2-imino-4-methyl-2,3-dihydrothiazole-5-carboxylates

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