Antimycobacterial terpenoids from Juniperus communis L. (Cuppressaceae)

Gordien, Andréa Y.; Gray, Alexander I.; Franzblau, Scott G.; Seidel, Véronique

doi:10.1016/j.jep.2009.09.007

Cited by 82 publications

(64 citation statements)

References 29 publications

(36 reference statements)

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“…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%

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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: Bicyclic Labdane-type Diterpenoidssupporting

confidence: 86%

“…Totarol has previously been reported in the needles of the common juniper (Gordien et al, 2009). The most abundant abietanes in our study were palustric acid and dehydroabietol (Table 6).…”

Section: Tricyclic Abietane-type Diterpenoidssupporting

confidence: 64%

Labdane-type diterpenoids from Juniperus communis needles

Basas-Jaumandreu

López

Heras

2015

Industrial Crops and Products

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“…They suggested that a high quantity of rosmarinic acid might be one of the responsible constituent for the observed antimycobacterial activity. Gordien et al (2009) studied two terpenes, sesquiterpene and longifolene; and two diterpenes, totarol and transcommunic acid, obtained from the aerial parts and roots of Juniperus communis. They reported that totarol showed the highest activity against Mycobacterium tuberculosis H37Rv and that longifolene and totarol exhibited the most activity against rifampicin-resistant variants.…”

Section: Discussionmentioning

confidence: 99%

Antimycobacterial Activity Some Different Lamiaceae Plant Extracts Containing Flavonoids and Other Phenolic Compounds

Aşkun¹,

Tümen²,

Satıl³

et al. 2012

Understanding Tuberculosis - New Approaches to Fighting Against Drug Resistance

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“…The anti-Mtb activity exerted by the crude extracts of E. camaldulensis and E. torelliana is due to the presence of tannins and triterpenes (saponins, cardiac and anthraquinones glycosides) all of which have been reported to possess good anti-mycobacterial activities against Mtb and other mycobacterial species (Adeniyi et.al., 2004;Macabeo et al, 2005;Kim et al, 2009;Gordien et al, 2009). The ability of these Eucalyptus extracts to inhibit the growth of Mtb is significant because the mycobacterial cell wall outer membrane is thought to act as a barrier to many substances including antibiotics.…”

Section: Discussionmentioning

confidence: 99%