Murrayatin, a coumarin from murraya exotica
TL;DR: The structure of murrayatin isolated from the leaves of Murraya exotica was established as 7methoxy-8-(2′-isovaleryloxy)-3′-hydroxy-3′methylbutyl) coumarin from spectral analysis, chemical transformation and synthesis.
About: This article is published in Phytochemistry.The article was published on 1983-01-01. It has received 20 citations till now. The article focuses on the topics: Murraya.
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TL;DR: In view of the established low toxicity, relative cheapness, presence in the diet, and occurrence in various herbal remedies of coumarins, it appears prudent to evaluate their properties and applications further.
Abstract: Coumarin (2H-1-benzopyran-2-one) is a plant-derived natural product known for its pharmacological properties such as anti-inflammatory, anticoagulant, antibacterial, antifungal, antiviral, anticancer, antihypertensive, antitubercular, anticonvulsant, antiadipogenic, antihyperglycemic, antioxidant, and neuroprotective properties. Dietary exposure to benzopyrones is significant as these compounds are found in vegetables, fruits, seeds, nuts, coffee, tea, and wine. In view of the established low toxicity, relative cheapness, presence in the diet, and occurrence in various herbal remedies of coumarins, it appears prudent to evaluate their properties and applications further.
614 citations
Cites background from "Murrayatin, a coumarin from murraya..."
...Fraxin [24] Anticancer Antiadipogenic Antioxidant Umbelliferone [25] Antitubercular Fraxidin [26] Antiadipogenic Antihyperglycemic Phellodenol A [8] Antitubercular Esculin, fraxetin [27] Antiadipogenic, Murrayatin [28] Auraptene [29]...
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...The latter was also found in the leaves of Murraya exotica [28]....
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TL;DR: In the screening program for new agrochemicals from Chinese medicinal herbs, Murraya exotica was found to possess insecticidal activity against the maize weevil, Sitophilus zeamais and red flour beetle, Tribolium castaneum.
Abstract: In our screening program for new agrochemicals from Chinese medicinal herbs, Murraya exotica was found to possess insecticidal activity against the maize weevil, Sitophilus zeamais and red flour beetle, Tribolium castaneum. The essential oil of aerial parts of M. exotica was obtained by hydrodistillation and investigated by GC and GC-MS. The main components of M. exotica essential oil were spathulenol (17.7%), alpha-pinene (13.3%), caryophyllene oxide (8.6%), and alpha-caryophyllene (7.3%). Essential oil of M. exotica possessed fumigant toxicity against S. zeamais and T. castaneum adults with LC(50) values of 8.29 and 6.84 mg/L, respectively. The essential oils also show contact toxicity against S. zeamais and T. castaneum adults with LD(50) values of 11.41 and 20.94 microg/adult, respectively.
89 citations
Cites background from "Murrayatin, a coumarin from murraya..."
...exotica revealed the presence of flavonoids, coumarins, phytosterols, alkaloids and volatile oil [10-25]....
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TL;DR: 7-hydroxycoumarin [umbelliferone, (2)], one of the most widely distributed coumarins, is often regarded as the parent, in a structural sense and also biogenetically, of a large number of the structurally more complex coumarin.
Abstract: Over the past 150 years, since Vogel in 1820 isolated the parent oxygen heterocycle, coumarin (1) from Coumarouna odorata = Dipteryx odorata (1), coumarins have been recognized as widely distributed plant products. The vast majority carry an oxygen substituent at C-7; consequently 7-hydroxycoumarin [umbelliferone, (2)], one of the most widely distributed coumarins, is often regarded as the parent, in a structural sense and also biogenetically, of a large number of the structurally more complex coumarins. A number of review articles on natural plant coumarins have appeared (154, 302, 344, 420, 525, 541, 548) since the last in this series (153), the most comprehensive, albeit dealing solely with coumarins of the Umbelliferae, being that of Nielsen in 1970 (419).
77 citations
TL;DR: Three new prenylated phenylpropenols, exotiacetals A-C (1-3), 10 new coumarin derivatives, exotimarins A-I (4-13), and 35 known analogues (14-48) were isolated from the roots of Murraya exotica.
Abstract: Three new prenylated phenylpropenols, exotiacetals A–C (1–3), 10 new coumarin derivatives, exotimarins A–I (4–13), and 35 known analogues (14–48) were isolated from the roots of Murraya exotica. The absolute configurations of the new compounds were assigned via comparison of their specific rotations, single-crystal X-ray diffraction data, Mosher’s method, the ECD exciton coupling method, comparison of experimental and calculated ECD data, and the ECD data of the in situ formed transition metal complexes. Compounds 1–3, which possess an unprecedented hexahydro-1H-isochromen-1-ol system, are presumably biosynthesized from two prenylated p-coumaryl alcohol moieties via Diels–Alder [4+2] cycloaddition and cyclic hemiacetal formation reactions. Compounds 1, 28, 33, and 35 demonstrated inhibition against LPS-induced NO production in BV-2 microglial cells with IC50 values of 8.6 ± 0.3, 11.8 ± 0.9, 15.5 ± 0.9, and 16.9 ± 1.0 μM, respectively.
34 citations
References
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60 citations
37 citations
TL;DR: In this article, 7-Methoxy-8-(2-hydroxy)-3-methyl-3-butenyl)-coumarin has been isolated from bitter orange oil and named auraptenol.
31 citations
TL;DR: The first report of auraptenol and meranzin hydrate in Murraya exotica was reported in this paper, and the absolute configuration of the 13 C NMR spectrum of the extractor was determined and found to possess S configuration at C-2.
30 citations
TL;DR: In this article, the coumarin derivatives osthol and coumurrayin were isolated from foliage of Murrayapaniculata (Rutaceae) and paniculatin was obtained.
Abstract: The coumarin derivatives osthol and coumurrayin were isolated from foliage of Murrayapaniculata (Rutaceae). In addition, a new coumarin, paniculatin, was obtained. By means of chemical degradation and u.v., n.m.r., and mass spectroscopy, the new compound was identified as 7-methoxy-8-(isovaleryloxy-2-keto-3-methylbutyl)coumarin.
15 citations