Chromenone Glucosides Acylated with Monoterpene Acids from the Leaves of <i>Eucalyptus camaldulensis</i> var. <i>obtusa</i>

Begum, Sabira; Farhat,; Siddiqui, Bina Shaheen

doi:10.1002/hlca.201000164

Cited by 6 publications

(3 citation statements)

References 20 publications

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“…Besides guajanosides A–E, six known acylated phenolic glycosides, including cypellocarpin C ( 3 ), eucamalduside A ( 4 ), cypellogin A ( 8 ), cypellogin B ( 9 ), quercetin-3- O -β-D-(6″- O - p -coumaroyl)-galactopyranoside ( 10 ), and guavaric A ( 11 ), were also isolated and identified from guava leaves. Compounds 1 – 4 were glycosides bearing 5,7-dihydroxychromone, 5 was a glycoside bearing the galloyl group, whereas 6 – 11 were quercetin glycosides.…”

Section: Results and Discussionmentioning

confidence: 99%

New Acylated Phenolic Glycosides with ROS-Scavenging Activity from Psidium guajava Leaves

et al. 2019

J. Agric. Food Chem.

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Reactive oxygen species and subsequent oxidative stress are reported to play important roles in chronic metabolic diseases. Plant-derived polyphenols, especially food-derived phenolics, have attracted a lot of attention due to their potential usage against oxidative stress-related diseases. The leaf of Psidium guajava (known as guava) is regarded as a good resource of polyphenols and its products are commercially available in Japan as functional foods against multiple chronic metabolism disorders. In the course of finding novel polyphenols with antioxidative activities from guava leaf, 11 acylated phenolic glycosides (1–11), including 5 new oleuropeic acid-conjugated phenolic glycosides, named guajanosides A–E (1, 2, and 5–7), along with 17 known meroterpenoides (12–28), were isolated and identified. Their structures were determined by spectroscopic data analysis, chemical degradation, and acid hydrolysis. Compounds 1, 2, and 5–11 displayed potent reactive oxygen species-scavenging activity in lipopolysaccharide-stimulated RAW 264.7 macrophage cells. Western blot revealed that compound 6 markedly increased the expression levels of nuclear factor-erythroid 2-related factor 2 (Nrf2), NAD(P)H quinone dehydrogenase 1 (NQO1), and the glutamate–cysteine ligase catalytic subunit. The current study revealed the presence of oleuropeic acid-derived phenolic glycosides in guava leaf and highlighted the potential usage of this type of phenolics against oxidative stress-related metabolic diseases via activation of the Nrf2 signaling pathway.

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Section: Results and Discussionmentioning

confidence: 99%

New Acylated Phenolic Glycosides with ROS-Scavenging Activity from Psidium guajava Leaves

et al. 2019

J. Agric. Food Chem.

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“…4 , Flavonoids (Apigenin, Chrysin, Flavone, Luteolin, Eriodictyol, Hesperetin, Naringenin, Pinocem-brin), 5 Triterpenoids (Oleanolic Acid, Maslinic Acid, Camaldulic Acid, Camaldulensic Acid) are the main constituents present in E. camaldulensis [6][7][8][9][10] .…”

Section: Constituentsmentioning

confidence: 99%

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2010

IJPSR

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Eucalyptus is a diverse genus of flowering trees and shrubs in the myrtle family, Myrtaceae. Different chemical constituents such as Sideroxylonal C, (+)-oleuropeic acid, cypellocarpins A, B and C, cypellogins A, B and C, Leptospermone, Isoleptospermone, grandinol, various essential oils and many others have been isolated from plants of eucalyptus genus. Various eucalyptus species have been reported to possess potent pharmacological actions against diabetes, hepatotoxicity, inflammation, cancer etc. This review article is presented to compile all the updated information on phytochemical and pharmacological activities of Eucalyptus species which have been performed by widely different methods.

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“…Myrtaceae is a plant family constituted by several genera with high agriculture and economic values . Among these genera, the Eucalyptus genus has attracted immense interest in the industry for the abundance of essential oils. , Essential oils from the plant of Eucalyptus globulus have been widely used as cosmetics and food ingredients. , In addition to volatile essential oils, phytochemicals including nonvolatile terpene derivatives, such as phloroglucinol meroterpenoids − and monoterpene acid glucose esters, − are also found in various Eucalyptus species. The monoterpene acid glucose esters are produced in the foliar secretory cavity of Eucalyptus plants .…”

Section: Introductionmentioning

confidence: 99%

New Monoterpene Acid and Gallic Acid Glucose Esters with Anti-Inflammatory Activity from Blue Gum (Eucalyptus globulus) Leaves

Liu

Wang

et al. 2022

J. Agric. Food Chem.

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Blue gum (Eucalyptus globulus) is a widely used botanical in the cosmeceutical and food industries. Although blue gum leaves are known for abundant essential oils, their nonvolatile phytochemical constituents and bioactivities remain unclear. Herein, a phytochemical investigation of blue gum leaves led to the identification of eight new monoterpene acid and gallic acid glucose esters (1−4 and 14−17; glubosides A−H, respectively) and 12 known analogues (5−13 and 18−20). Their structures were determined based on extensive spectroscopic data analysis, chemical degradation, and chiral separation. Oleuropeic acid conjugated glucose esters (1−13, 15, 16, 18, and 20) are reported as epimeric mixtures. Compounds 7, 12, 14, 19, and 20 (at 30 μM) inhibited nitrite release in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Compounds 7 and 14 (at 3−30 μM) also down-regulated proinflammatory biomarkers, including cytokines (TNF-α, IL-6, and IL-1β), protein expression (iNOS and COX-2), and transcription factor nuclear translocation (NF-κB) in LPS-stimulated RAW264.7 cells. This work highlights the anti-inflammatory potential of phytochemicals from blue gum leaves, which supports their further development as cosmeceutical and/or nutraceutical products.

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Chromenone Glucosides Acylated with Monoterpene Acids from the Leaves of Eucalyptus camaldulensis var. obtusa

Cited by 6 publications

References 20 publications

New Acylated Phenolic Glycosides with ROS-Scavenging Activity from Psidium guajava Leaves

New Acylated Phenolic Glycosides with ROS-Scavenging Activity from Psidium guajava Leaves

Untitled

New Monoterpene Acid and Gallic Acid Glucose Esters with Anti-Inflammatory Activity from Blue Gum (Eucalyptus globulus) Leaves

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