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Journal ArticleDOI

Nodakenetin acetate: A new coumarin from Boenninghausenia albiflora

01 Sep 1973-Phytochemistry (Pergamon)-Vol. 12, Iss: 9, pp 2312-2314

AboutThis article is published in Phytochemistry.The article was published on 1973-09-01. It has received 12 citation(s) till now. The article focuses on the topic(s): Boenninghausenia & Isopimpinellin.

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Citations
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Journal ArticleDOI
TL;DR: The biogenesis, structural diversity and distribution of simple, furano- and pyranocoumarins in the Rutaceae is reviewed and the potential value of these compounds as taxonomic markers and their possible functions are discussed.
Abstract: The biogenesis, structural diversity and distribution of simple, furano- and pyranocoumarins in the Rutaceae is reviewed. The potential value of these compounds as taxonomic markers and their possible functions are discussed. The distribution of simple cinnamic acid precursors of coumarins in the family is also reviewed.

133 citations

Book ChapterDOI
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).

73 citations

Journal ArticleDOI
TL;DR: Seven different physicochemical parameters (MW, Clog P, CMR, μ, Ehomo, Elumo and Hf) and four major biological activities (antioxidant, anti-inflammatory, antiviral/antitumor and immunomodulating) are discussed in this review.
Abstract: A literature survey was conducted on herbs, their preparations and ingredients with reported liver protection activities, in which a total of 274 different species and hundreds of active ingredients have been examined. These ingredients can be roughly classified into two categories according to their activities: (1) the main ingredients, such as silybin, osthole, coumarin, glycyrrhizin, saikosaponin A, schisandrin A, flavonoids; and (2) supporting substances, such as sugars, amino acids, resins, tannins and volatile oil. Among them, some active ingredients have hepatoprotective activities (e.g. anti-inflammatory, anticancer, antioxidant, immunomodulating and liver cirrhosis-regulating effects). Calculation of physicochemical parameters indicates that the main ingredients with negative and positive Elumo values possibly display their hepatoprotective effects through different mechanisms, such as antioxidative, anti-inflammatory and immunomodulating effects. As the combination of herbs may achieve some treatment effects synergistically and/or additively, it is common in Chinese medicine to use mixtures of various medicinal herbs with pharmacologically active compounds to have synergistic and/or additive effects, or to reduce harmful effects of some pharmacologically active compounds. In particular, the active compounds with Clog P around 2 are suitable for passive transport across membranes and accessible to the target sites. Thus, Elumo and Clog P values are good indicators among the calculated parameters. Seven different physicochemical parameters (MW, Clog P, CMR, μ, Ehomo, Elumo and Hf) and four major biological activities (antioxidant, anti-inflammatory, antiviral/antitumor and immunomodulating) are discussed in this review. It is hoped that the discussion may provide some leads in the development of new hepatoprotective drugs.

63 citations


Cites background from "Nodakenetin acetate: A new coumarin..."

  • ...Structures of some representative liver protective compounds [10-34] and key physicochemical parameters which may affect their pharmacokinetic and pharmacodynamic effects are provided (Additional file 2)....

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Journal ArticleDOI
TL;DR: Bioassay guided fractionation of Boenninghausenia sessilicarpa resulted in the isolation of a new dimeric coumarin glucoside 9′-methoxyl rutarensin and a cytotoxic compound rutamarin, as well as an antivirus component leptodactylone, together with six known coumarins.
Abstract: Bioassay guided fractionation of Boenninghausenia sessilicarpa (Rutaceae) resulted in the isolation of a new dimeric coumarin glucoside 9'-methoxyl rutarensin (1) and a cytotoxic compound rutamarin (4), as well as an antivirus component leptodactylone (8), together with six known coumarins. Their structures were elucidated by 1D- and 2D NMR spectroscopy and ESI-MS analyses, respectively. Rutamarin (4) showed significant inhibitory activities against A-549, Bel-7402, HepG-2 and HCT-8 tumour cell lines with IC50s of 1.318, 2.082, 2.306 and 2.497 microg/ml. In addition, leptodactylone (8) showed potent protective activity on cells infected by SARS-CoV with ratio of 60% at 100 microg/ml.

30 citations


References
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Journal ArticleDOI
TL;DR: A study of the extractives of the three species of the genus Ptelea (Rutaceae) has yielded typically rutaceous coumarins and furoquinoline alkaloid alkaloids.
Abstract: A study of the extractives of the three species of the genus Ptelea (Rutaceae) has yielded typically rutaceous coumarins and furoquinoline alkaloids. The fruit of P. aptera contains small amounts of a new furoquinoline alkaloid shown to be 7-isopentenyloxy-γ-fagarine (III). A further new alkaloid, identified as 3-isopentenyl-4-methoxy-7,8-methylenedioxy-2-quinolone (II), has been obtained from the extracts of one sample of P. trifoliata L.

30 citations

Journal ArticleDOI
TL;DR: From the methanolic extract of the leaves of Boenninghausenia albiflora MEISSNER var.
Abstract: From the methanolic extract of the leaves of Boenninghausenia albiflora MEISSNER var. japonica S. SUZUKI, a new coumarin, named matsukaze-lactone (I), C20H14O6, m.p. 267∼268°, was isolated. Methylation of I with dimethyl sulfate and methanolic alkali gave an acid (IIa), C22H22O8, which was oxidized to an acid (IIIa), C18H18O8. By decarboxylation of IIIa with copper powder, 2, 2', 4, 6'-tetramethoxybiphenyl (V) was obtained. From these results, the structural formula (Ia), (Ib) and (Ic) were proposed for matsukaze-Iactone.

25 citations