New acylated flavonol glycosides with antibacterial activity from root barks of Sophora japonica

Si, Chuanling; An, Liang-Liang; Xie, Dan-Ni; Liu, Cui-Yun; Chen, Xiaoqian; Wang, Guan-Hua; Huo, Dan; Yang, Qingxiang; Hong, Yanping

doi:10.1007/s00226-016-0809-1

Cited by 15 publications

(9 citation statements)

References 32 publications

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“…Of the flavonoids present in Scots pine (P. sylvestris) and Norway spruce, quercetin (Rauha et al 2000; Xu and Lee 2001;Ibewuike et al 1997;Puupponen-Pimiä et al 2001), kaempferol (Rauha et al 2000;Tsuchiya et al 1996; Xu and Lee 2001), and myricetin ( Xu and Lee 2001;Puupponen-Pimiä et al 2001) aglycones, which are produced from the parent compound taxifolin, were determined to have antibacterial activity. Generally, the glycosides of the flavonols were observed to be inactive ( Xu and Lee 2001;Puupponen-Pimiä et al 2001;Silva et al 2010), although acetylated glycosides of flavonols are observed to be antibacterial (Si et al 2016). However, synergistic antibacterial activities between flavonols and their glycosides have been observed.…”

Section: Antibacterial Activity Of Flavonolsmentioning

confidence: 99%

Bioactive phenolic compounds, metabolism and properties: a review on valuable chemical compounds in Scots pine and Norway spruce

2019

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Phenolics and extracted phenolic compounds of Scots pine (Pinus sylvestris) and Norway spruce (Picea abies) show antibacterial activity against several bacteria. The majority of phenolic compounds are stilbenes, flavonoids, proanthocyanidins, phenolic acids, and lignans that are biosynthesized in the wood through the phenylpropanoid pathway. In Scots pine (P. sylvestris), the most abundant phenolic and antibacterial compounds are pinosylvin-type stilbenes and flavonol-and dihydroflavonol-type flavonoids, such as kaempferol, quercetin, and taxifolin and their derivatives. In Norway spruce (P. abies) on the other hand, the main stilbene is resveratrol and the major flavonoids are quercetin and myricetin. In general, when the results from the literature regarding the activities of flavonoid glycosides and their aglycones against a total of twenty-one microorganisms are summarized, it was found that phenolic glycosides are less active than the corresponding aglycones, although a number of exceptions are also known. The aglycones in plants respond to various kinds of biotic stress. Synergistic effects between aglycones and their glycosides have been observed. Minimum inhibition concentrations of below 10 mg L-1 against bacteria have been reported for gallic acid, apigenin, and several methylated and acylated flavonols present in these industrially important trees. In general, the phenolic compounds are more active against Gram-positive bacteria, but apigenin is reported to exhibit strong activity against Gram-negative bacteria. The present review lists some of the biosynthesis pathways for the antibacterial phenolic metabolites found in Scots pine (P. sylvestris) and Norway spruce (P. abies). The antimicrobial activity of the compounds is collected and compared to gather information about the most effective secondary metabolites.

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Section: Antibacterial Activity Of Flavonolsmentioning

confidence: 99%

Bioactive phenolic compounds, metabolism and properties: a review on valuable chemical compounds in Scots pine and Norway spruce

2019

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“…Root barks Significant antibacterial activity against Staphylococcus aureus and moderate antibacterial activity against Klebsiella pneumonia, whereas the concurrently isolated non-acylated flavonol glycoside, exhibited no antimicrobial activity against the tested bacterial species (Si et al, 2016) Ó 2022 Institute of Food, Science and Technology (IFSTTF).…”

Section: Sophora Japonicamentioning

confidence: 99%

“…3. Examples of acylated flavonoids isolated from Pisum sativum shoots (21)–(24) (Ferreres et al ., 1995), Onobrychis viciifolia aerial parts (25)–(34) (Veitch et al ., 2011), Vicia angustifolia leaves and stems (35)–(36) (Takemura et al ., 2002), Astragalus caprinus leaves (37) and (38) (Semmar et al ., 2005), Baphia nitida leaves (39) and (40) (Chaabi et al ., 2010), Astragalus gombiformis aerial parts (41)–(43) (Montoro et al ., 2013), Tipuana tipu leaves (44) (Amen et al ., 2015), Lens culinaris aerial parts (45)–(50) (Rolnik et al ., 2020), Ceratonia siliqua seeds (51) (Gohar et al ., 2009), Leucenia leucocephala leaves (52) (Haggag et al ., 2011), Mimosa pigra leaves (53)–(54) (Okonkwo et al ., 2016; Phuong et al ., 2017), Pterogyne nitens fruits (55) (Regasini et al ., 2008), Sophora japonica root barks (56)–(58) (Si et al ., 2016), and Caesalpinia ferrea leaves (59) and (60) (Hussein et al ., 2016), are presented in Table S2.…”

Section: Isolation Identification and Biological Activities Of Acylat...mentioning

confidence: 99%

Acylated polyphenolics of family Fabaceae: distribution, chemodiversity, and bioactivity, a comprehensive review

Khalil

Sabry

El‐Askary

et al. 2023

Int J of Food Sci Tech

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Polyphenolics are the most common class of plant-derived natural products. They play an important role in the protection of both plants and humans. Acylated polyphenolics, i.e., polyphenolics esterified with either phenolic or organic acids, are abundant in several plant families including Fabaceae. This review article is intended to shed light on the distribution, isolation, chemodiversity, and bioactivity of acylated polyphenolics obtained from selected fabaceous plants mentioned herein. Isolation of these metabolites was mostly performed via successive column chromatography, including preparative and semi-preparative HPLC. Structure elucidation was achieved through interpretation of spectral data. Meanwhile, detection was chiefly accomplished via diverse liquid chromatography/mass spectrometric analyses. Compared to usual polyphenolics, these unique acylated compounds were found of higher stability and bioactivity. The current survey targets to provide a comprehensive overview of the medicinal role of acylated polyphenolics that may encourage the incorporation of fabaceous plants in pharmaceuticals.

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“…In this regard, a better understanding of the increased bioactivity of glycoconjugates in comparison to free aglycones could promote the discovery and development of new glycosylated compounds with higher activity and efficacy (e.g., vancomycin). , Indeed, if the sugar residue is derivatized by acylation or phenylacylation, its chemical and biological diversity might be considerably increased. Such variations have a significant influence on the growth inhibition of both Gram-positive and Gram-negative bacterial strains, especially resistant strains such as vancomycin-resistant Enterococci (VRE) or methicillin-resistant Staphylococcus aureus (MRSA). , Actually, a kaempferol diacylrhamnoside was previously isolated from a Lauraceae plant (i.e., Laurus nobilis) and it exhibited antibacterial activity against MRSA (MIC < 8 μg/mL) . Thus, as part of our constant efforts to discover undescribed molecules from natural sources with important bioactivity and chemosystematic significance, we continued to explore the chemical potential of P.…”

Section: Introductionmentioning

confidence: 99%

“…Such variations have a significant influence on the growth inhibition of both Gram-positive and Gram-negative bacterial strains, especially resistant strains such as vancomycin-resistant Enterococci (VRE) or methicillin-resistant Staphylococcus aureus (MRSA). 19,25 Actually, a kaempferol diacylrhamnoside was previously isolated from a Lauraceae plant (i.e., Laurus nobilis) and it exhibited antibacterial activity against MRSA (MIC < 8 μg/mL). 26 Thus, as part of our constant efforts to discover undescribed molecules from natural sources with important bioactivity and chemosystematic significance, we continued to explore the chemical potential of P. caerulea.…”

Section: ■ Introductionmentioning

confidence: 99%

Caerulines A and B, Flavonol Diacylglycosides from Persea caerulea

et al. 2021

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Two undescribed 4′-O-methylkaempferol-[3″,4″-di-p-coumaroyl]-α-l-rhamnopyranosides, caerulines A and B (1–2), along with three known 4′-O-methylkaempferol diacylrhamnosides isomers (3–5) were isolated from an ethanol extract of the leaves of Persea caerulea, a native plant growing on the Colombian Caribbean coast. The chemical structures of 1 and 2 were elucidated by spectroscopic methods. The effect of compounds 1–5 against four pathogenic microorganisms [i.e., methicillin-resistant Staphylococcus aureus (MRSA), Acinetobacter baumannii, Candida albicans, and Aspergillus fumigatus] was tested in vitro. The compounds exhibited no activity against these pathogens except MRSA (MIC 12–48 μg/mL). Caeruline B (2) was found to be the most active compound with a modest anti-MRSA activity (MIC = 12 μg/mL).

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New acylated flavonol glycosides with antibacterial activity from root barks of Sophora japonica

Cited by 15 publications

References 32 publications

Bioactive phenolic compounds, metabolism and properties: a review on valuable chemical compounds in Scots pine and Norway spruce

Bioactive phenolic compounds, metabolism and properties: a review on valuable chemical compounds in Scots pine and Norway spruce

Acylated polyphenolics of family Fabaceae: distribution, chemodiversity, and bioactivity, a comprehensive review

Caerulines A and B, Flavonol Diacylglycosides from Persea caerulea

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