The distribution of lignanoids in the order coniferae

Castro, M. Angeles; Gordaliza, Marina; Corral, José M. Miguel del; Feliciano, Arturo San

doi:10.1016/0031-9422(95)00512-9

Cited by 52 publications

(51 citation statements)

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“…Interestingly, the cyclic lignan deoxypodophyllotoxin was isolated by Carpenter et al (2012) from the aerial parts of the common juniper and subsequently studied for its potent antitumor, antiviral and anti-inflammatory activities. To the best of our knowledge, deoxypodophyllotoxin identified by Carpenter et al (2012) together with dihydrodehydrodiconiferyl alcohol (Castro et al, 1996) are the only ones of the eight lignans identified that has previously been reported in the needles of the common-juniper.…”

Section: Lignansmentioning

confidence: 87%

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Labdane-type diterpenoids from Juniperus communis needles

Basas-Jaumandreu

López

Heras

2015

Industrial Crops and Products

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Herein we report the extraction of labdane-type diterpenoids from the needles of the common juniper (Juniperus communis ssp. communis var. communis L.), and identification of them as the major class of compounds in this species. Furthermore, and to the best of our knowledge we provide the first-ever report some of these compounds (nor-16-imbricatolic, nor-16-acetylimbricatolic and acetylimbricatolic acids) as natural compounds. Imbricataloic and imbricatolic acids were the most abundant compounds, accounting for 65% of the total extract. We also found long-chain secondary alcohols (n-alkan-10-ols) and secondary/secondary alkanediols (4,10-, 5,10-, 6,10-, 7,10-), which we report here for the first time ever in the genus Juniperus. In total, we identified 127 compounds: of these, 48 (nonacosan-10-ols, -tocopherols and lignans) are described here for the first time in Juniperus and 54 (including alkanols, phytol, sterols and flavonoids), for the first time in common juniper. Highlights 127 phytochemical constituents of the needles of Juniperus communis were investigated with imbricatolic and imbricatalic acid as the most abundants  3 Labdane-type diterpenoids are new natural products  17 compounds have no precedent in Juniperus genus and 32 are described for the first time from Juniperus communis Keywords: Juniperus communis; Common juniper; Diterpenoids; Labdane-type; Alkanediols; Imbricatolic acid; Gas chromatography-Mass spectrometry (GC/MS); Trimethylsilyl (TMS) ether derivatives. IntroductionThe genus Juniperus (Cupressaceae) comprises 68 species and 36 varieties growing principally in the northern hemisphere . The chemical composition of the genus Juniperus has been extensively reviewed by Seca & Silva (2006). Table 1 summarizes the phytochemical characteristics of the principal compounds from the genus Juniperus, excluding terpenes, secondary alcohols and secondary diols, which we discuss separately in a latter section.The species Juniperus communis L. comprises four subspecies, including the common juniper (J. communis ssp. communis), a coniferous evergreen shrub that has a broad geographic range throughout the holarctic region. In fact, it exhibits the largest range of any woody plant, spanning the cool, temperate, part of the Northern Hemisphere: from mountains in the southern arctic, to roughly 30ºN latitude in North America, Europe and Asia. It tolerates a variety of climatic and edaphic conditions. The surface layer of plant leaves typically contains many classes of compounds, including alkanes, primary alcohols, acids, aldehydes, terpenes and phenols. However, there are very few reports on the overall composition of common-juniper needles. Thus, in the study reported here, we sought to analyze the soluble fraction of common-juniper needles.We analyzed the total extract of common-juniper needles and identified each wax-class of compounds, discovering many acyclic and cyclic compounds from three major groups: terpenoids (e.g. sesquiterpenes and diterpenes); phenols (including phenolic acids,...

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Section: Lignansmentioning

confidence: 87%

“…We indeed identified eight lignans in the extract, albeit in minor amounts (total concentration: 99.1 mg/kg dry weight). These Castro et al, 1996) are the only ones of the eight lignans identified that has previously been reported in the needles of the common-juniper. …”

mentioning

confidence: 84%

Labdane-type diterpenoids from Juniperus communis needles

Basas-Jaumandreu

López

Heras

2015

Industrial Crops and Products

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“…Aplin et al, 1963;Smith, 1976;Castro et al, 1996;Mongrand et al, 2001). This means that these biomolecules are synthesized by a restricted number of plant taxa and can be used as specific markers.…”

Section: Introductionmentioning

confidence: 99%

Determination of the molecular signature of fossil conifers by experimental palaeochemotaxonomy – Part 1: The Araucariaceae family

Hautevelle

Michels

2013

Biogeosciences

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Twelve species of the conifer family Araucariaceae, including Araucaria (6 species), Agathis (3 species) and Wollemia (1 species) genera, were submitted to artificial maturation by confined pyrolysis. The aim of these experiments is to transform the biomolecules synthesized by these species into their homologous geomolecules in laboratory conditions. Determination of the diagenetic molecular signatures of Araucariaceae through experimentation on extant representatives allows us to complete our knowledge in botanical palaeochemotaxonomy. Such knowledge is relevant to palaeoenvironmental, environmental and archaeology purposes. All artificially diagenetic species of Araucariaceae are firstly characterized by a predominance of saturated tetracyclic diterpenoids including ent-beyerane, phyllocladanes and ent-kauranes. Moreover, Araucaria genus shows a high relative abundance of bicyclic sesquiterpenoids, particularly the cadalane-type compounds accompanied by those of eudesmane and bisabolane types as well as chamazulene and pentamethyl-dihydroindenes. Diterpenoids are of labdane, isopimarane and abietane types (essentially derived from abietanoic acids) as well as isohexyl alkylaromatic hydrocarbons. Compared to the tetracyclic diterpenoids, these compounds show a relatively lower abundance, reaching trace levels in the case of saturated abietanes. Distributions of sesquiterpenoids and diterpenoids of Agathis show some similarities to that of Araucaria, with the exception of one species, in which the tetracyclic compounds are absent and the abietane type (essentially derived from abietanoic acids) predominant. High similarities between the Wollemia and Araucaria genera are observed. Both are characterized by some high relative abundance of tetracyclic compounds with no predominance of other specific diterpenoids

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“…1), 2) The lignans are widely distributed in the plant kingdom and known for about one thousand species.…”

Section: Introductionmentioning

confidence: 99%

Gas Chromatography/Mass Spectrometry of the Lignans in Resin of Callitris preissii

Yamamoto

Cox

Simoneit

2010

J. Mass Spectrom. Soc. Jpn.

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The total extract of resin from Callitris preissii was analyzed by gas chromatography/mass spectrometry and 34 lignans, underivatized and as trimethylsilyl ether derivatives, were identified by interpretation of the mass spectra. The lignans in the resin include 13 new lignans, i.e., four secoisolariciresinol derivatives, four lariciresinol derivatives, 3῏,4῏-methylenedioxy-7῏-hydroxylariciresinol, 3,4-methylenedioxypinoresinol isomer, and two matairesinol derivatives. Furthermore, 17 lignans of the resin are characterized by methylenedioxy substitution on either or both guaiacylpropyl units or the syringylpropyl unit: i.e., five secoisolariciresinol derivatives, three lariciresinol derivatives, 3῏,4῏-methylenedioxy-7῏-hydroxylariciresinol, three pinoresinol derivatives, and five matairesinol derivatives, have methylenedioxy structures. Eleven lignans, including two secoisolariciresinol derivatives, four lariciresinol derivatives, two pinoresinol derivatives, and three matairesinol derivatives, contain a syringyl moiety.

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The distribution of lignanoids in the order coniferae

Cited by 52 publications

References 64 publications

Labdane-type diterpenoids from Juniperus communis needles

Labdane-type diterpenoids from Juniperus communis needles

Determination of the molecular signature of fossil conifers by experimental palaeochemotaxonomy – Part 1: The Araucariaceae family

Gas Chromatography/Mass Spectrometry of the Lignans in Resin of Callitris preissii

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