New formylated phloroglucinol compounds from Eucalyptus globulus foliage

Chenavas, Sophie; Fiorini-Puybaret, Christel; Joulia, P; Camille, Larrouquet; Waton, Hughes; Martinez, Agathe; Casabianca, Hervé; Fabre, Bernard

doi:10.1016/j.phytol.2014.11.002

Cited by 14 publications

(14 citation statements)

References 22 publications

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“…The characteristic fragment ion at m/z 249 from compound 5 results from the retro-Diels-Alder cleavage of the molecular ion (Soliman et al, 2014). It is the most abundant and thus the diagnostic fragment ion for sideroxylonals, followed by a less abundant peak of m/z 181, suggested to be the diformyl phloroglucinol moiety by Chenavas et al (2015). For macrocarpals, the diagnostic fragment ion detected in the compounds 1-4 is m/z 207, in agreement with previous reports (Eyles et al, 2003; Okba et al, 2017), and we here suggest it to be the isopentyl diformyl phloroglucinol moiety + C 2 H 2 .…”

Section: Discussionmentioning

confidence: 98%

Quantification and Localization of Formylated Phloroglucinol Compounds (FPCs) in Eucalyptus Species

et al. 2019

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The Eucalyptus genus is a hyper-diverse group of long-lived trees from the Myrtaceae family, consisting of more than 700 species. Eucalyptus are widely distributed across their native Australian landscape and are the most widely planted hardwood forest trees in the world. The ecological and economic success of Eucalyptus trees is due, in part, to their ability to produce a plethora of specialized metabolites, which moderate abiotic and biotic interactions. Formylated phloroglucinol compounds (FPCs) are an important class of specialized metabolites in the Myrtaceae family, particularly abundant in Eucalyptus . FPCs are mono- to tetra-formylated phloroglucinol based derivatives, often with an attached terpene moiety. These compounds provide chemical defense against herbivory and display various bioactivities of pharmaceutical relevance. Despite their ecological and economic importance, and continued improvements into analytical techniques, FPCs have proved challenging to study. Here we present a simple and reliable method for FPCs extraction, identification and quantification by UHPLC-DAD-ESI-Q-TOF-MS/MS. The method was applied to leaf, flower bud, and flower samples of nine different eucalypt species, using a small amount of plant material. Authentic analytical standards were used to provide high resolution mass spectra and fragmentation patterns. A robust method provides opportunities for future investigations into the identification and quantification of FPCs in complex biological samples with high confidence. Furthermore, we present for the first time the tissue-based localization of FPCs in stem, leaf, and flower bud of Eucalyptus species measured by mass spectrometry imaging, providing important information for biosynthetic pathway discovery studies and for understanding the role of those compounds in planta .

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Section: Discussionmentioning

confidence: 98%

Quantification and Localization of Formylated Phloroglucinol Compounds (FPCs) in Eucalyptus Species

et al. 2019

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“…FPCs constitute an interesting and valuable group of specialized metabolites in Eucalyptus trees. In this study, we investigated the effects of single and combined O 3 and wounding stresses on the six selected FPCs present in E. globulus foliage [26,28,46,47]. Concentrations of different identified FPCs are highly variable in E. globulus leaves (Figure 2 and Figure 3) and have been reported previously by Lawler et al [41].…”

Section: Discussionmentioning

confidence: 64%

“…Eucalyptus globulus has been demonstrated to be a strong constitutive volatile terpenoid emitter [7,12,45]. In addition, the presence of different FPCs, including macrocarpals A, B, D, H, I, J, N, P, Q, and sideroxylonal A, have also been observed in E. globulus leaf, bark, and wood tissues [26,28,46,47].…”

Section: Introductionmentioning

confidence: 99%

Ozone and Wounding Stresses Differently Alter the Temporal Variation in Formylated Phloroglucinols in Eucalyptus globulus Leaves

et al. 2019

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Formylated phloroglucinol compounds (FPCs) are a class of plant specialized metabolite present in the Myrtaceae family, especially in the genus Eucalyptus. FPCs are widely investigated due to their herbivore deterrence properties and various bioactivities of pharmaceutical relevance. Despite the increasing number of studies elucidating new FPCs structures and bioactivity, little is known about the role of those compounds in planta, and the effects of environmental stresses on FPC concentration. Ozone (O3) and wounding are key stress factors regularly confronted by plants. In this study, we investigated how O3, wounding, and their combination affected individual and total FPC foliar concentration of the economically important species Eucalyptus globulus. Six individual FPCs, including five macrocarpals and one sideroxylonal, showed different response patterns to the single and combined stresses. Total macrocarpals only increased under single O3 treatment, whereas total sideroxylonals only increased in response to wounding treatment, suggesting different physiological roles played by the two groups of FPCs predominantly existing in E. globulus foliage. Total FPCs increased significantly under individual wounding and O3 treatments but not under the combined treatment. A principal component analysis indicated that all different treatments had unique FPC fingerprints. Total phenolic contents increased in all O3 and wounding treatments, and a marginally positive correlation was found between total FPCs and total phenolic contents. We suggest that, depending on the concentration and composition, FPCs play multiple physiological roles in planta, including serving as antioxidants to scavenge the reactive oxygen species brought about by O3 and wounding stresses.

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“…globulus was treated with solvent partition, chromatographic isolation, and spectral analysis to afford compounds 1 – 6 . The other five known compounds were identified as macrocarpal C ( 2 ), macrocarpal Q ( 5 ), macrocarpal E ( 6 ), euglobal‐III ( 3 ), and euglobal‐V ( 4 ), by comparison of spectral data with literature data. The purity of these compounds was proven by TLC and HPLC (purity > 95% for all compounds) ( Figure ).…”

Section: Resultsmentioning

confidence: 99%

Phloroglucinol Derivatives from the Fruits of Eucalyptus globulus and Their Cytotoxic Activities

Pham

Mohammad

et al. 2018

Chemistry & Biodiversity

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A new phloroglucinol derivative, named eucalyptin B (1), along with five related known compounds (2 - 6), was isolated from the fruits of Eucalyptus globulus. Their structures were elucidated by means of 1D- and 2D-NMR spectroscopy, with the absolute configuration of 1 determined by electronic circular dichroism (ECD) calculations. All isolated compounds (1 - 6) were evaluated for their cytotoxic activities against lung (A549), breast (4T1), and skin (B16F10) cancer cell lines. On the basis of cell viability assay, the cytotoxic activity of eucalyptin B (1) was further confirmed by apoptosis assay. Additionally, after treatment with eucalyptin B (1), the apoptosis factor proteins (Bcl2 and Bax) and caspase-3 levels in A549 cells were also determined by Western-blot analysis. By cytotoxic assay, eucalyptin B (1) exhibited potent cytotoxicity against A549 cells with an IC value of 1.51 μm and induced concentration dependent apoptosis of up to 49%. Additionally, eucalyptin B (1) inhibited 5-fold and increased 10-folds in the level of Bcl2 and Bax, respectively. Furthermore, the 11-fold increase in the level of caspase-3 confirmed eucalyptin B (1) activated caspase dependent apoptosis pathway. In conclusion, the isolated compound eucalyptin B (1) has promising cytotoxic activity in tumor cells, especially in A549.

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New formylated phloroglucinol compounds from Eucalyptus globulus foliage

Cited by 14 publications

References 22 publications

Quantification and Localization of Formylated Phloroglucinol Compounds (FPCs) in Eucalyptus Species

Quantification and Localization of Formylated Phloroglucinol Compounds (FPCs) in Eucalyptus Species

Ozone and Wounding Stresses Differently Alter the Temporal Variation in Formylated Phloroglucinols in Eucalyptus globulus Leaves

Phloroglucinol Derivatives from the Fruits of Eucalyptus globulus and Their Cytotoxic Activities

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