Cypellocarpin C and other compounds from the fruits of Eucalyptus globulus Labill.

Guo, Qingmei; Yang, Xiu‐Wei

doi:10.1016/j.bse.2005.10.018

Cited by 15 publications

(11 citation statements)

References 17 publications

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“…Gallic acid, eucaglobulin and globulusin B have been detected previously in leaves and fruits of E. globulus (Hou et al, 2000;Hasegawa et al, 2008;Boulekbache-Makhlouf et al, 2010). Compounds [Cypellocarpin C, methyl ellagic acid, 3-O-methylellagic acid 3'-a-rhamnoside and methylellagic acid-acetyl-rhamnoside] have been reported in fruits (Guo and Yang, 2006;Boulekbache-Makhlouf et al, 2010) and bark (Kim et al, 2001;Santos et al, 2011) of E. globulus, but they have not been reported in leaves.…”

Section: Fractionmentioning

confidence: 99%

Qualitative and Semi‐quantitative Analysis of Phenolics in Eucalyptus globulus Leaves by High‐performance Liquid Chromatography Coupled with Diode Array Detection and Electrospray Ionisation Mass Spectrometry

Boulekbache‐Makhlouf

Meudec

Mazauric

et al. 2012

Phytochemical Analysis

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Section: Fractionmentioning

confidence: 99%

Qualitative and Semi‐quantitative Analysis of Phenolics in Eucalyptus globulus Leaves by High‐performance Liquid Chromatography Coupled with Diode Array Detection and Electrospray Ionisation Mass Spectrometry

Boulekbache‐Makhlouf

Meudec

Mazauric

et al. 2012

Phytochemical Analysis

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“…Up to now, little has been done on the phenolic composition of the fruit of this plant. It has been reported to contain gallic acid , , cypellocarpin C, macrocarpal A, macrocarpal B , and other ellagic acid derivatives (3,4,3′- O -trimethylellagic acid, 3- O -methylellagic acid 4′- O -(2′′- O -acetyl)-α- l -rhamnopyranoside, 3- O -methylellagic acid, 4′- O -α- l -rhamnopyranoside, and 3- O -methylellagic acid) .…”

Section: Introductionmentioning

confidence: 99%

Analysis by High-Performance Liquid Chromatography Diode Array Detection Mass Spectrometry of Phenolic Compounds in Fruit of Eucalyptus globulus Cultivated in Algeria

Boulekbache‐Makhlouf

Meudec

Chibane

et al. 2010

J. Agric. Food Chem.

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A method based on high-performance liquid chromatography coupled with diode array detection and electrospray ionization mass spectrometry (HPLC-DAD-ESI-MS) following fractionation by chromatography on a Sephadex LH-20 column has been developed to determine the phenolic composition of fruit of Eucalyptus globulus growing in Algeria. The presence of 18 gallotannins, 26 ellagitannins, and 2 flavonols was established. Tentative identification is provided for these compounds on the basis of UV-visible spectra and mass spectrometry data. Most compounds described in this study have not previously detected in fruit of E. globulus. Moreover, this is the first report of methyl digalloyl diglucose, 3,3'-O-dimethylellagic acid 4-O-β-glucopyranoside, ellagic acid hexose, methyl ellagic acid pentose, methyltetragalloylglucose, and valoneic acid isomers (sanguisorbic, flavogallic acid dilactone) in the genus Eucalyptus. Quantitatively, ellagic acid and its derivatives, including ellagitannins, are largely predominant.

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“…The isolation of compounds 3 and 12 from the E. globulus is reported here for the first time. Compounds 1 , 4 , and 5 had previously been described only in the fruits of E. globulus [ 25 , 35 ]. We propose that litseagermacrane ( 1 ) may be a biogenetic precursor of the cadinane-type intermediate involved in the biosynthesis of eucalyptal A ( 4 ).…”

Section: Discussionmentioning

confidence: 99%

Anti-Infectivity against Herpes Simplex Virus and Selected Microbes and Anti-Inflammatory Activities of Compounds Isolated from Eucalyptus globulus Labill.

Brezáni

Leláková

Hassan

et al. 2018

Viruses

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Herpes simplex virus (HSV) causes numerous mild-to-serious human diseases, including mucocutaneous herpes infections and life-threatening herpes encephalitis. Moreover, herpes viral lesions can be complicated by inflammation and secondary bacterial infections. The development of resistance to antiviral drugs along with the undesirable side effects of these drugs are relevant argue for the development of new anti-HSV drugs with diverse mechanisms of action. Eucalyptus extracts have been used for decades to combat various infectious diseases. We isolated and studied 12 pure compounds and one mixture of two constitutional isomers from the leaves and twigs of E. globulus. The structures were identified by spectroscopic methods (NMR, HR-MS, IR) and all of them were tested for antiherpetic activity against the replication of antigen types HSV-1 and HSV-2. Tereticornate A (12) (IC50: 0.96 μg/mL; selectivity index CC50/IC50: 218.8) showed the strongest activity in the anti-HSV-1 assay, even greater than acyclovir (IC50: 1.92 μg/mL; selectivity index CC50/IC50: 109.4), a standard antiviral drug. Cypellocarpin C (5) (EC50: 0.73 μg/mL; selectivity index CC50/EC50: 287.7) showed the most potent anti-HSV-2 activity, also more intensive than acyclovir (EC50: 1.75 μg/mL; selectivity index CC50/EC50: 120.0). The antimicrobial activity of the isolated compounds was also evaluated against the bacteria Staphylococcus aureus, Bacillus cereus, Escherichia coli, and Pseudomonas aeruginosa and the yeast Candida albicans. The anti-inflammatory potential was examined using LPS-stimulated THP-1-XBlue™-MD2-CD14 and THP-1 macrophages and focusing on the influences of the NF-κB/AP-1 activity and the secretion of pro-inflammatory cytokines IL-1β and TNF-α.

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Cypellocarpin C and other compounds from the fruits of Eucalyptus globulus Labill.

Cited by 15 publications

References 17 publications

Qualitative and Semi‐quantitative Analysis of Phenolics in Eucalyptus globulus Leaves by High‐performance Liquid Chromatography Coupled with Diode Array Detection and Electrospray Ionisation Mass Spectrometry

Qualitative and Semi‐quantitative Analysis of Phenolics in Eucalyptus globulus Leaves by High‐performance Liquid Chromatography Coupled with Diode Array Detection and Electrospray Ionisation Mass Spectrometry

Analysis by High-Performance Liquid Chromatography Diode Array Detection Mass Spectrometry of Phenolic Compounds in Fruit of Eucalyptus globulus Cultivated in Algeria

Anti-Infectivity against Herpes Simplex Virus and Selected Microbes and Anti-Inflammatory Activities of Compounds Isolated from Eucalyptus globulus Labill.

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