Flavonol dimers from callus cultures of Dysosma versipellis and their in vitro neuraminidase inhibitory activities

Chen, Ridao; Duan, Rui-Gang; Wei, Yannan; Zou, Jianhua; Li, Junwei; Liu, Xiaoyue; Wang, Haiyan; Guo, Ying; Li, Qiuhong; Dai, Jungui

doi:10.1016/j.fitote.2015.10.005

Cited by 11 publications

(13 citation statements)

References 27 publications

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“…In fact, the pair of racemates share an identical CAS (Chemical Abstracts Service) number (167276-19-9). However, a similar pair of racemates has been found in Dysosma versipellis [22].…”

Section: Resultssupporting

confidence: 62%

“…Regioselectivity is supported by recent evidence showing that callus cultures could produce five anti Diels-Alder dimers (dysoverines A-E) and no syn Diels-Alder dimers in Dysosma versipellis [22].…”

Section: Resultsmentioning

confidence: 73%

“…As mentioned above, catecholic flavonol is an important family of natural products [33,34]. However, some catecholic flavonols were recently found to co-exist with the relevant Diels-Alder anti-dimers in the same plant, which was Dysosma versipellis [22]. As seen in Figure 9, these flavonols included kaempferide, podoverine A, kaempferol, and 3-O-methylquercetin; their relevant Diels-Alder dimers, however, were numbered as dimers 1-5 in the study.…”

Section: Resultsmentioning

confidence: 99%

“…Of these, iron and LPO are relevant to ferroptosis. Undoubtedly, the formation of ortho-quinone with π-π conjugation has facilitated Diels-Alder dimerization reactions [22][23][24]27,70,71,72]. During plant metabolism, quite a few factors can oxidize catecholic moieties to ortho-quinone, including bio-enzymes (e.g., catechol oxidase and aurone synthase) [25,26,85], iron [83,86], LPO [86], and free radicals [75].…”

Section: Resultsmentioning

confidence: 99%

“…Structurally, quercetin bears a 2,3-C=C bond, 3-OH, and 3′,4′-di-OHs (i.e., 3′,4′-catecholic moiety), thus, it belongs to typical catecholic flavonol ( Figure 1A). This catecholic flavonol can be enzymatically transformed into a quercetin dimer (i.e., quercetin Diels-Alder anti-dimer, QDAD, Figure 1B) during plant metabolism [22][23][24][25][26]. Because of this, quercetin and its dimer metabolite QDAD usually co-exist in the same plant [27].…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Inhibitory Effect and Mechanism of Action of Quercetin and Quercetin Diels-Alder anti-Dimer on Erastin-Induced Ferroptosis in Bone Marrow-Derived Mesenchymal Stem Cells

Zeng

Liu

et al. 2020

Antioxidants

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In this study, the anti-ferroptosis effects of catecholic flavonol quercetin and its metabolite quercetin Diels-Alder anti-dimer (QDAD) were studied using an erastin-treated bone marrow-derived mesenchymal stem cell (bmMSCs) model. Quercetin exhibited higher anti-ferroptosis levels than QDAD, as indicated by 4,4-difluoro-5-(4-phenyl-1,3-butadienyl)-4-bora-3a,4a-diaza-s-indacene-3-undecanoic acid (C11-BODIPY), 2′,7′-dichlorodihydrofluoroscein diacetate (H2DCFDA), lactate dehydrogenase (LDH) release, cell counting kit-8 (CCK-8), and flow cytometric assays. To understand the possible pathways involved, the reaction product of quercetin with the 1,1-diphenyl-2-picrylhydrazyl radical (DPPH●) was measured using ultra-performance liquid-chromatography coupled with electrospray-ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC-ESI-Q-TOF-MS). Quercetin was found to produce the same clusters of molecular ion peaks and fragments as standard QDAD. Furthermore, the antioxidant effects of quercetin and QDAD were compared by determining their 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide radical-scavenging, Cu2+-reducing, Fe3+-reducing, lipid peroxidation-scavenging, and DPPH●-scavenging activities. Quercetin consistently showed lower IC50 values than QDAD. These findings indicate that quercetin and QDAD can protect bmMSCs from erastin-induced ferroptosis, possibly through the antioxidant pathway. The antioxidant pathway can convert quercetin into QDAD—an inferior ferroptosis-inhibitor and antioxidant. The weakening has highlighted a rule for predicting the relative anti-ferroptosis and antioxidant effects of catecholic flavonols and their Diels-Alder dimer metabolites.

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“…In fact, the pair of racemates share an identical CAS (Chemical Abstracts Service) number (167276-19-9). However, a similar pair of racemates has been found in Dysosma versipellis [22].…”

Section: Resultssupporting

confidence: 62%

Section: Resultsmentioning

confidence: 73%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Inhibitory Effect and Mechanism of Action of Quercetin and Quercetin Diels-Alder anti-Dimer on Erastin-Induced Ferroptosis in Bone Marrow-Derived Mesenchymal Stem Cells

Zeng

Liu

et al. 2020

Antioxidants

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Combating influenza: natural products as neuraminidase inhibitors

2018

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Mining Therapeutic Efficacy from Treasure Chest of Biodiversity and Chemodiversity: Pharmacophylogeny of Ranunculales Medicinal Plants

Hao

Zheng

et al. 2022

Chin. J. Integr. Med.

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Ranunculales is an order of angiosperms, containing 7 families, i.e., Ranunculaceae (at least 50 genera, >2,000 species), Berberidaceae (17 genera, 650 species), Menispermaceae (65 genera, >350 species), Lardizabalaceae (9 genera, 50 species), Circaeasteraceae (2 species), Papaveraceae (38 genera, >700 species), and Eupteleaceae (2 species, Appendix 1). Ranunculales belongs to the basal eudicots, in which it is the most basal clade; its widely known members include poppies, barberries, monseed, akebia and buttercupss. The chemodiversity of Ranunculaceae, the fl agship family of Ranunculales, and their correlation with the biodiversity and pharmacotherapy, have been systematically reviewed by us in the context of pharmacophylogeny. (1) In recent years, the research enthusiasm for the other 4 major Ranunculales families has been growing rapidly, as plants of these families also meet human needs for food, fl avours, fragrances, and not the least, medicines during long history. Ranunculales plants form the basis of sophisticated traditional medicine systems, e.g., Chinese medicine (CM) and Ayurveda medical system. (2) These systems of medicine give rise to some important Ranunculalesbased drugs still in use today. (3,4) According to incomplete statistics, 573 Ranunculaceae and 308 Berberidaceae species were in medicinally hot nodes; (4) the therapeutic efficacy of 2 families differed substantially. For instance, up to 361 Chinese Ranunculaceae species are used against musculoskeletal diseases, followed by 321 against hepatic diseases, 242 against circulatory diseases, and 210 against skin diseases, etc.; in contrast, as many as 251 Chinese Berberidaceae species are used against eyesight diseases, followed by 249 against hepatic diseases, 242 against digestive diseases and 90 against oral diseases, etc. Nevertheless, except Ranunculaceae, the

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Flavonol dimers from callus cultures of Dysosma versipellis and their in vitro neuraminidase inhibitory activities

Cited by 11 publications

References 27 publications

Inhibitory Effect and Mechanism of Action of Quercetin and Quercetin Diels-Alder anti-Dimer on Erastin-Induced Ferroptosis in Bone Marrow-Derived Mesenchymal Stem Cells

Inhibitory Effect and Mechanism of Action of Quercetin and Quercetin Diels-Alder anti-Dimer on Erastin-Induced Ferroptosis in Bone Marrow-Derived Mesenchymal Stem Cells

Combating influenza: natural products as neuraminidase inhibitors

Mining Therapeutic Efficacy from Treasure Chest of Biodiversity and Chemodiversity: Pharmacophylogeny of Ranunculales Medicinal Plants

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