Phenolic Glycosides from the Twigs of <i>Salix glandulosa</i>

Kim, Chung Sub; Kwon, Oh Wook; Kim, Sun Yeou; Choi, Sang Un; Kim, Jae Yoon; Han, Ji Young; Choi, Soo Im; Choi, Jae Gark; Kim, Ki‐Hyun; Lee, Kang Ro

doi:10.1021/np500488v

Cited by 20 publications

(23 citation statements)

References 19 publications

(62 reference statements)

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“…Derivatives of cinnamic acid, such as e. g. coumaric or ferulic acid occur in nature both as ( E )‐ and ( Z )‐isomers; they both were isolated e. g. from corn steep liquor . Moreover, phenolic glycosides containing both ( E )‐ and ( Z )‐ p ‐coumaric acid were isolated from Salix glandulosa . It is interesting to note that some simple glycosylated derivatives of ( Z )‐ p ‐coumaric acid act as leaf‐opening factors in nyctinastic plants (e. g. Albizia julibrissin or Mimosa ) .…”

Section: Resultsmentioning

confidence: 99%

“…[19] Moreover, phenolic glycosides containing both (E)-and (Z)-p-coumaric acid were isolated from Salix glandulosa. [20] It is interesting to note that some simple glycosylated derivatives of (Z)-p-coumaric acid act as leaf-opening factors in nyctinastic plants (e. g. Albizia julibrissin or Mimosa). [21] Isomerization between (E)-and (Z)-isomers of cinnamic acid derivatives occurs in nature typically under direct UV-A light.…”

Section: Full Paper Ascwiley-vchdementioning

confidence: 99%

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Glycosidase‐Catalyzed Synthesis of Glycosyl Esters and Phenolic Glycosides of Aromatic Acids

et al. 2019

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Phenolic glycosides occur naturally in many plants and as such are often present in the human diet. Their isolation from natural sources is usually laborious due to their presence in complex matrices. Their chemical and enzymatic syntheses have been found complex, time-consuming, and costly, yielding only small amounts of glycosylated products. In quest of a convenient biocatalytic route to structurally complex phenolic glycosides, we discovered that the rutinosidase from Aspergillus niger not only efficiently converts hydroxylated aromatic acids (e. g. coumaric and ferulic acids) into the respective phenolic rutinosides, but surprisingly also catalyzes the formation of the respective glycosyl esters. We report here the results of a systematic study presenting the unique synthesis of naturally occurring glycosyl esters and phenolic glycosides accomplished by glycosidase catalysis. A panel of aromatic acids was tested as glycosyl acceptors and the crucial structural features required for the formation of glycosyl esters were identified. In the light of the present structure-activity relationship study, a plausible reaction mechanism was proposed. All the products were fully structurally characterized by NMR and MS. Scheme 2. Glycosylation of (E)-p-coumaric acid (3). Scheme 3. Proposed mechanism of rutinosylation of hydroxycinnamic acids at the carboxy moiety.

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Section: Resultsmentioning

confidence: 99%

Section: Full Paper Ascwiley-vchdementioning

confidence: 99%

Glycosidase‐Catalyzed Synthesis of Glycosyl Esters and Phenolic Glycosides of Aromatic Acids

et al. 2019

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“…Fraction J was kept aside due to its complexity and paucity. White solid 1. H and13 C NMR spectral data identical to those of tremulacin[12].…”

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confidence: 80%

“…The genus Salix (willow) comprises of about 400 species of deciduous trees and shrubs [1]. Extracts of its barks, roots and leaves were ingredients in folk medicine to treat fever, pain and inflammation over many centuries [2].…”

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confidence: 99%

“…Extracts of its barks, roots and leaves were ingredients in folk medicine to treat fever, pain and inflammation over many centuries [2]. Previous phytochemical investigations on the genus Salix have led to reports on phenolic compounds, flavonoids, terpenes and lignans [1]. The phenolic compounds isolated, salicylic glycosides, were the most abundant with reported analgesic, antipyretic, antiinflammatory and antirheumatic properties [3][4][5].…”

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confidence: 99%

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Salicylic Glycosides in Salix mucronata with Antioxidant and Antiinflammatory Activities

Dissanayake

Zhang

Gaber

et al. 2017

Natural Product Communications

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The leaves of Salix mucronata (safsaf willow), widely distributed along the Nile River in Egypt, is used in traditional medicine. This prompted us to examine the bioactive components in its leaves using in-vitro antioxidant and antiinflammatory assays. Bioassay-guided purification of the methanolic extract afforded six known phenolic compounds (1-6). Hexane extract did not contain bioactive compounds except chlorophyll. Pure isolates 1-3 and 6 inhibited lipid peroxidation (LPO) by 56-86% at 5 µg/mL and cyclooxygenase enzymes (COX-1 and-2) by 22-75% at 25 µg/mL. This is the first report on the bioassayguided characterization of constituents in S. mucronata leaves. Our results support the anecdotal medicinal claims of safsaf leaves.

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Boosting the Performance of Flexible Perovskite Photodetectors Using Hierarchical Plasmonic Nanostructures

Lee,

Won

et al. 2024

Small Structures

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Plasmonic nanostructures can enhance the performance of photodetectors (PDs) owing to their amplification effect in light absorption, leading to overcoming the inherent properties of the photoactive layer. Herein, hierarchical plasmonic nanopatterns have been prepared and used for high‐performance flexible perovskite PDs. The developed hierarchical nanostructures, featuring nanoposts on cross‐nanograting patterns, exhibit a notably enhanced light trapping effect compared to hierarchical nanostructures based on a unidirectional simple nanograting structure. Moreover, hierarchical pattern‐based perovskite PDs show a photoresponsivity of 580 mA W−1 and a specific detectivity of 3.2 × 1012 Jones, which are 420% and 990% higher than those of perovskite PDs without plasmonic nanostructures, respectively. Furthermore, a flexible 10 × 10 PD array has been developed, which enables the accurate mapping of light signals with exceptional operational and mechanical stabilities, under a bending radius as small as 8 mm and after undergoing more than 1000 bending cycles. Comprehensive analyses using finite‐difference time‐domain calculations and photoluminescence mapping reveal the effective light trapping effect of hierarchical plasmonic patterns in the perovskite layers. This work provides an efficient approach to achieve high‐performance perovskite optoelectronic devices.

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Phenolic Glycosides from the Twigs of Salix glandulosa

Cited by 20 publications

References 19 publications

Glycosidase‐Catalyzed Synthesis of Glycosyl Esters and Phenolic Glycosides of Aromatic Acids

Glycosidase‐Catalyzed Synthesis of Glycosyl Esters and Phenolic Glycosides of Aromatic Acids

Salicylic Glycosides in Salix mucronata with Antioxidant and Antiinflammatory Activities

Boosting the Performance of Flexible Perovskite Photodetectors Using Hierarchical Plasmonic Nanostructures

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