Oxygenated di- and tricyclic diterpenoids of southern hemisphere conifers

Cox, Robert E.; Yamamoto, Shuichi; Otto, Angelika; Simoneit, Bernd R.T.

doi:10.1016/j.bse.2006.09.013

Cited by 80 publications

(74 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…These include trans-communic acid ([M] ·+ = 374), which in our study exhibited a similar MS pattern to that indicated by Cox et al (2007). This compound was also found in the needles of the common juniper by and by Gordien et al (2009), and isocupressic acid was previously reported in this plant by De .…”

Section: Bicyclic Labdane-type Diterpenoidssupporting

confidence: 86%

“…However, they have been reported as biomarkers of the Cupressaceae (cypress) family according to Cox et al (2007).…”

Section: Tricyclic Abietane-type Diterpenoidsmentioning

confidence: 99%

“…Based on the work of Cox et al (2007), we identified four pimaranes in the commonjuniper needles: pimaric acid, sandaracopimaric acid, isopimaric acid and levopimaric acid, all these which have a molecular ion at m/z 374. Isopimaric acid and sandaracopimaric acid have previously been reported in the needles of this plant .…”

Section: Tricyclic Pimarane-type Diterpenoidsmentioning

confidence: 99%

See 2 more Smart Citations

Labdane-type diterpenoids from Juniperus communis needles

Basas-Jaumandreu

López

Heras

2015

Industrial Crops and Products

View full text Add to dashboard Cite

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,...

show abstract

Section: Bicyclic Labdane-type Diterpenoidssupporting

confidence: 86%

“…However, they have been reported as biomarkers of the Cupressaceae (cypress) family according to Cox et al (2007).…”

Section: Tricyclic Abietane-type Diterpenoidsmentioning

confidence: 99%

Section: Tricyclic Pimarane-type Diterpenoidsmentioning

confidence: 99%

See 1 more Smart Citation

Labdane-type diterpenoids from Juniperus communis needles

Basas-Jaumandreu

López

Heras

2015

Industrial Crops and Products

View full text Add to dashboard Cite

show abstract

“…This obtained configuration is consistent with a structure similar to that of clerodane. However, its report in extant conifers is limited to a few derivatives of ent-clerodadienes (Otto and Wilde, 2001) and is restricted to two Araucaria species including A. bidwillii (Caputo and Mangoni, 1974;Cox et al, 2007). 2,6-dimethyl-1-(4-methylpentyl)naphthalene and 6-ethyl-2-dimethyl-1-(4-methylpentyl)-naphthalene are abundant for most species and in traces in A. launbenfelsii.…”

Section: Bicyclic Diterpenoidsmentioning

confidence: 99%

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

Hautevelle

Michels

2013

Biogeosciences

View full text Add to dashboard Cite

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

show abstract

“…The isolation of the diterpenes used as reference compounds was described by Popova et al (2009). In the cases of lack of the corresponding reference compounds, the structures were proposed on the basis of their general fragmentation and using reference literature spectra where possible (mainly from Cox, Yamamoto, Otto, & Simoneit, 2007). The semiquantification of the main compounds was carried out by internal normalisation with the area of each compound.…”

Section: Identification and Semiquantification Processmentioning

confidence: 99%

The specific chemical profile of Mediterranean propolis from Malta

et al. 2011

View full text Add to dashboard Cite

a b s t r a c tSeventeen Maltese propolis samples were studied by GC-MS after silylation. They exhibited the typical Mediterranean chemical profile, rich in diterpene compounds (18-92% of TIC, GC-MS): 32 individual diterpenes were identified; 22 of them were present in each specimen. The other abundant compound group was that of sugars and sugar derivatives. In some samples, however, another compound group was observed (0-12% of TIC, GC-MS); the corresponding mass spectra were consistent with monoand sesquiterpenyl esters of substituted benzoic acids. Two new propolis constituents of this group, daucane diterpene esters of hydroxybenzoic acids, were isolated. Their origin is suggested to be Ferula communis, as they are taxonomic markers for this species. All propolis samples were active against Staphylococcus aureus but only those with high concentrations of terpenyl esters showed antifungal activity against Candida albicans. The present results confirm that Mediterranean propolis is a valuable natural product with potential to improve human health.

show abstract

Oxygenated di- and tricyclic diterpenoids of southern hemisphere conifers

Cited by 80 publications

References 35 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

The specific chemical profile of Mediterranean propolis from Malta

Contact Info

Product

Resources

About