Arylnaphthalene Lignan Research Articles

A novel enzymatic dehydrogenation of podophyllotoxin congeners by yeast cells

The biotransformation of aryltetralin lignans to arylnaphthalene lignans in presence of yeast is described. Podophyllotoxone, an oxidation product of podophyllotoxin on incubation with yeast from different sources produced dehydropodophyllotoxin, an important representative of arylnaphthalene lignans.

Synthesis and hypolipidemic activity of diesters of arylnaphthalene lignan and their heteroaromatic analogs.

A series of diesters of arylnaphthalene lignan and their heteroaromatic analogs were synthesized and evaluated for hypolipidemic activity. The disasters with modifications at C-3 showed excellent hypocholesterolemic and high-density lipoprotein (HDL) cholesterol-elevating activities. Structure-activity analysis indicated that the 2-pyridylmethyl ester 5l has the optimum activity.

Minor lignans from haplophyllum cappadocicum

Haplophyllum cappadocicum, an annual herb native to Turkey, has yielded a new arylnaphthalene lignan glycoside, (-)-haplomyrtoside, which is shown to be haplomyrtin 4-O-β- d-apiofuranoside on the basis of detailed spectral analyses. Additionally, a known lignan diglycoside, (-)-majidine, a known tetralin lignan, (-)-1β-polygamain, and vanillic acid are reported for the first time from this species.

ChemInform Abstract: Arylnaphthalene Lignans as Novel Series of Hypolipidemic Agents Raising High‐Density Lipoprotein Level.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Hindered Rotation in Arylnaphthalene Lignans

Many arylnaphthalene lignans show biological activity and although few of them contain stereogenic centers, they may nevertheless be chiral if there is hindered rotation about the aryl−naphthalene bond. A relatively high barrier to rotation may give rise to separable rotational enantiomers (atropisomers) which might have quite different pharmacological properties. In order to investigate this possibility we have synthesized the natural products justicidin A, justicidin B, retro-helioxanthin, retro-justicidin B, and helioxanthin as well as four other arylnaphthalenes lignan analogs. We have studied the aryl−naphthalene rotational barrier in these compounds by dynamic NMR and HPLC and find barriers to rotation ranging from 16.9 to 21.5 kcal/mol. This translates to half-lives for individual atropisomers of less than 10 min at room temperature. The experimentally found barriers are compared to those obtained from molecular orbital calculations.

Arylnaphthalene lignans as novel series of hypolipidemic agents raising high-density lipoprotein level.

A series of arylnaphthalene lignans were synthesized and tested for hypolipidemic activity. The most potent compound (4b) (TA-7552) not only reduced serum cholesterol, but also increased high-density lipoproteins cholesterol in rats. The effective dose of 4b is 100 times less than that of cholestyramine. Structure-activity relationships are discussed.

Justicidin E: A new leukotriene biosynthesis inhibitor.

Justicidin E, an arylnaphthalene lignan, has been identified as a potent inhibitor of leukotriene biosynthesis by human leukocytes (IC 50 = 70 nM) and a non-redox inhibitor of 5-lipoxygenase activity.

Cytotoxic Constituents from Hyptis verticillata

A new cytotoxic (P-388 ED50 4 microgm/ml) arylnaphthalene lignan has been isolated from the Mexican medicinal plant Hyptis verticillata (Lamiaceae) and characterized as 5-methoxydehydropodophyllotoxin [1]. Eight additional lignans were also obtained by bioactivity-directed fractionation using the brine shrimp lethality test. Of these, the dehydro-beta-peltatin methyl ether 2 (P-388 ED50 1.8 microgm/ml) is reported for the first time as a natural product isolate. The other bioactive compounds were identified as dehydropodophyllotoxin [3], deoxydehydropodophyllotoxin [4]. (--)-yatein [5], 4'-demethyldeoxypodophyllotixin [6], isodeoxypodophyllotoxin [7], deoxypicropodophyllin [8], and beta-apopicropodophyllin [9]. Each of these compounds was evaluated against a panel of cell lines comprising a number of human cancer cell types [breast, colon, fibrosarcoma, lung, prostate, KB, and KB-VI (a multi-drug resistant cell line derived from KB)] and murine lymphocytic leukemia (P-388). Lignans 1-4 showed marginal cytotoxic activity against the human cell lines tested. In contrast, compounds 5-9 demonstrated a general nonspecific activity comparable to that of podophyllotoxin [12] (ED50 < 10-2 microgm/ml). In addition, the antimitotic potential of these compounds was determined in the astrocytoma (ASK) assay. Finally, the plant was also shown to contain the flavonoid sideritoflavone (KB ED50 1.6 microgm/ml) and the known pentacyclic triterpenoids ursolic, maslinic, 2 alpha-hydroxyursolic and oleanolic acids.

Isodaurinol, an arylnaphthalene lignan from Haplophyllum cappadocicum

Six lignans, isodaurinol, daurinol, justicidin A, justicidin B, diphyllin, and (−)-matairesinol, four furoquinoline alkaloids, dictamnine, robustine, haplopine, and skimmianine, and two coumarins, scopoletin and seselin have been isolated from Haplophyllum cappadocicum, a plant native to eastern Turkey. Isodaurinol, the novel arylnaphthalene lignan, is a structural isomer of the already known daurinol. This is also the first report of the isolation of (−)matairesinol from the genus Haplophyllum. The structures of the compounds described were established by spectroscopic analyses.

A New Synthesis of Arylnaphthalene Lignan Lactones

Arylnaphthalene lignan lactones 1a-e were synthesized in a one-pot procedure from methyl 4-aryl-1-oxo-1,2,3,4-tetrahydro-3-naphthoates 2a-e prepared from the corresponding cyanohydrins, based on a tandem aromatization-lactonization reaction.

Chemical Constituents of the Flora of Jordan, Part V-B. Three New Arylnaphthalene Lignan Glucosides from Haplophyllum buxbaumii

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTChemical Constituents of the Flora of Jordan, Part V-B. Three New Arylnaphthalene Lignan Glucosides from Haplophyllum buxbaumiiYousef Al-Abed, Salim Sabri, Musa Abu Zarga, Zahir Shah, and Atta-ur-RahmanCite this: J. Nat. Prod. 1990, 53, 5, 1152–1161Publication Date (Print):September 1, 1990Publication History Published online1 July 2004Published inissue 1 September 1990https://doi.org/10.1021/np50071a003RIGHTS & PERMISSIONSArticle Views261Altmetric-Citations26LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (560 KB) Get e-Alerts Get e-Alerts

Tumour-inhibitory aryltetralin lignans in Podophyllum versipelle, Diphylleia cymosa and Diphylleia grayi

Roots/rhizome of Podophyllum versipelle contain eight aryltetralin lignans: podophyllotoxin, desoxypodophyllotoxin, β-peltatin, podophyllotoxone, and the four corresponding 4′-demethyl derivatives, together with O-glucosides of podophyllotoxin, 4′-demethylpodophyllotoxin, β-peltatin and α-peltatin. β-Peltatin is the major constituent (1.4%), and while the podophyllotoxin content (0.32%) is higher than that of P. peltatum (0.25%), it is considerably inferior to that of P. hexandrum (4.3%). Roots and leaves of Diphylleia cymosa and D. grayi also contain Podophyllum lignans and their O-glucosides, together with the arylnaphthalene lignan diphyllin. Lignan patterns in Diphylleia roots are markedly different from those in the leaves. The podophyllotoxin content of D. grayi root is high (1.3%), whilst only small amounts are found in D. cymosa roots which accumulate β-peltatin instead. The leaves of D. cymosa contain relatively high levels of podophyllotoxin (0.54%), 4′-demethylpodophyllotoxin (0.10%), 4′-demethyldesoxypodophyllotoxin (0.11%) and diphyllin (0.13%), and are potentially a good alternative source of lignans for drug use.

Arylnaphthalene lignan from Jatropha gossypifolia

2,3-Bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3′,4′-dimethoxyphenyl)-naphthalene has been isolated from Jatropha gossypifolia. This is the first report of the isolation of this arylnaphthalene lignan from a natural source.

13C NMR spectra of arylnaphthalene lignans

The13C NMR spectra have been investigated of a number of arylnaphthalene lignans of plant origin: daurinol and its acetyl derivative and reduction product, justicidin A, justicidin B and its reduction product and the diacetyl derivative of the reduction product, and diphyllin and its acetate. The values of the chemical shifts of the carbon atoms in the spectra of the compounds investigated and the nature of their change according to structural factors are discussed and an assignment is made of the resonance lines in the spectra. The characteristics of the spectrum of one compound are used as models for others. The parameters of the13C NMR spectra of a number of naphthalene derivatives are also used. On the basis of the results of the assignment of the signals, difference values of the chemical shifts of the carbon atoms in the series of compounds investigated have been determined. Using the experimental results as a background, some examples taken from the literature of investigations of the13C NMR spectra of related compounds have been analyzed.

Highly regioselective lactone formation catalyzed by ruthenium complexes. An application to synthesis of arylnaphthalene lignans

Ruthenium catalyzed hydrogenation of cyclic anhydrides and dehydrogenation of diols have been successfully applied to the highly regioselective synthesis of arylnaphthalene lignans.

The synthesis of lignans and related structures using quinodimethanes and isobenzofurans: approaches to the podophyllins

Novel routes to 1-aryl-5,6-dialkoxy-1,3-dihydrobenzo[c]thiophene 2,2-dioxides (13) and to the corresponding benzo[c]furan (8) have been developed; these species yield quinodimethanes (12)via thermal extrusion of SO2 and isobenzofurans (5c) in an acid-catalysed process, respectively, which then react with various dienophiles to provide structural analogues of the aryltetralin and arylnaphthalene lignans.

A convergent mercury mediated lignan synthesis

Bis(thiophenyl) derivatives of dibenzylbutyrolactones undergo cyclisation elimination and dehydrogenation when treated with mercuric trifluoroacetate. The process is a short, efficient synthesis of certain arylnaphthalene lignans.