Isolation of enantiomeric furolactones and furofurans from Rubus idaeus L. with neuroprotective activities

Zhou, Le; Feng-ying, Han; Lu, Li-Wei; Yao, Guo‐Dong; Zhang, Yingying; Wang, Xiaobo; Lin, Bin; Huang, Xiao‐Xiao; Song, Shao‐Jiang

doi:10.1016/j.phytochem.2019.05.008

Cited by 17 publications

(7 citation statements)

References 42 publications

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“…Enantiomers having different biological activities is well-known and widespread [38]. This is also known for the drugs currently used for PD treatment, e.g., L-DOPA.…”

Section: Discussionmentioning

confidence: 99%

Biologically Active Echinulin-Related Indolediketopiperazines from the Marine Sediment-Derived Fungus Aspergillus niveoglaucus

et al. 2019

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Seven known echinulin-related indolediketopiperazine alkaloids (1–7) were isolated from the Vietnamese sediment-derived fungus Aspergillus niveoglaucus. Using chiral HPLC, the enantiomers of cryptoechinuline B (1) were isolated as individual compounds for the first time. (+)-Cryptoechinuline B (1a) exhibited neuroprotective activity in 6-OHDA-, paraquat-, and rotenone-induced in vitro models of Parkinson’s disease. (−)-Cryptoechinuline B (1b) and neoechinulin C (5) protected the neuronal cells against paraquat-induced damage in a Parkinson’s disease model. Neoechinulin B (4) exhibited cytoprotective activity in a rotenone-induced model, and neoechinulin (7) showed activity in the 6-OHDA-induced model.

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“…Enantiomers having different biological activities is well-known and widespread [38]. This is also known for the drugs currently used for PD treatment, e.g., L-DOPA.…”

Section: Discussionmentioning

confidence: 99%

Biologically Active Echinulin-Related Indolediketopiperazines from the Marine Sediment-Derived Fungus Aspergillus niveoglaucus

et al. 2019

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“…The protective activity of neolignan enantiomers 24a/24b against H 2 O 2 -induced cell injury in human neuroblastoma SHSY5Y cells was tested and the (+)-enantiomer showed obviously better activity than the (−)-enantiomer [20]. In a same assay model by Zhou et al, the analogous enantiomeric pair 72a/72b also exhibited a similar trend of bioactivity difference, with the dextroisomer displaying better protective effect than the reference drug and the levoisomer being found to be inactive [46]. Further investigations revealed that (+)-72a could significantly decrease the percentages of both early and late apoptotic cells.…”

Section: Cell Protectionmentioning

confidence: 92%

“…Furan-incorporating lignans are a class of common NPs with one or more or modified furan rings in the structures. These lignan enantiomers reported in this period mainly comprise three subtypes, namely, normal furan-type (40 and 41), benzofuran-type (42)(43)(44)(45)(46)(47)(48)(49)(50)(51)(52)(53)(54)(55)(56)(57) and furofuran-type (58-63) (for structures, see Figure 3; for names, see Table S3 in Supplementary Materials). Compound 40, a normal furan-type lignan enantiomer pair with 8-7 and 7-O-8 connections, was reported as a racemic mixture from magnolia salicifolia in 1984 [35], and was synthesized in 1992 [36]; however, its chiral separation and abs.…”

Section: Cyclic Lignansmentioning

confidence: 99%

“…configs. of which were established by analyses of the calculated shielding tensor values and ECD data [46], while the enantiomer 58b had been reported as an optically pure molecule from Lycium chinense in 2013 [47]. The other two pairs of furolactone enantiomers 59a/59b and 60a/60b were isolated from Archidendron clypearia in 2018 [48] and Dendrobium nobile in 2016 [49], respectively.…”

Section: Cyclic Lignansmentioning

confidence: 99%

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Natural Enantiomers: Occurrence, Biogenesis and Biological Properties

Capon

et al. 2022

Molecules

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The knowledge that natural products (NPs) are potent and selective modulators of important biomacromolecules (e.g., DNA and proteins) has inspired some of the world’s most successful pharmaceuticals and agrochemicals. Notwithstanding these successes and despite a growing number of reports on naturally occurring pairs of enantiomers, this area of NP science still remains largely unexplored, consistent with the adage “If you don’t seek, you don’t find”. Statistically, a rapidly growing number of enantiomeric NPs have been reported in the last several years. The current review provides a comprehensive overview of recent records on natural enantiomers, with the aim of advancing awareness and providing a better understanding of the chemical diversity and biogenetic context, as well as the biological properties and therapeutic (drug discovery) potential, of enantiomeric NPs.

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“…[23] Their absolute configurations are finally determined by comparison between the experimental and calculated ECD spectra. [24][25][26] Finally, 1a was identified as 7S,8S, and 1b was identified as 7R,8R. They are named (7S,8S)-sarcacoumarin (1a) and (7R,8R)-sarcacoumarin (1b) (Figure 3).…”

Section: Introductionmentioning

confidence: 99%

Coumarins from Sarcandra glabra (Thunb.) Nakai and Acetylcholinesterase Inhibiting Activity

Bai

Zhang

et al. 2022

Chemistry & Biodiversity

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Nine coumarins including a pair of new enantiomers (1a/1b) and seven known compounds (2 -8) were isolated from Sarcandra glabra (Thunb.) Nakai. Among them, compounds 1a and 1b were naturally occurring coumarin-phenylpropanoid conjugate enantiomers. Their structures were identified by NMR and ECD calculations. Compounds 1-8 were tested for acetylcholinesterase (AchE) inhibiting activity. The results of the enzymology experiment showed that compound 3 demonstrated obvious AchE inhibitory activity which showed the IC 50 value of 1.982 � 0.003 μM, and the binding sites were predicted by molecular docking.

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Isolation of enantiomeric furolactones and furofurans from Rubus idaeus L. with neuroprotective activities

Cited by 17 publications

References 42 publications

Biologically Active Echinulin-Related Indolediketopiperazines from the Marine Sediment-Derived Fungus Aspergillus niveoglaucus

Biologically Active Echinulin-Related Indolediketopiperazines from the Marine Sediment-Derived Fungus Aspergillus niveoglaucus

Natural Enantiomers: Occurrence, Biogenesis and Biological Properties

Coumarins from Sarcandra glabra (Thunb.) Nakai and Acetylcholinesterase Inhibiting Activity

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