Antibacterial bibenzyl derivatives from the tubers of Bletilla striata

Jiang, Sai; Wan, Ke; Lou, Hua‐Yong; Yi, Ping; Zhang, Ni; Zhou, Mei; Song, Zhi-Qin; Wang, Wei; Ming-kai, WU; Pan, Weidong

doi:10.1016/j.phytochem.2019.03.022

Cited by 34 publications

(15 citation statements)

References 29 publications

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“…This work of 2017 was reported in the doctoral thesis of U. Kauhl in 2018 [ 22 ]. Parallel to our synthetic work, other researchers reported the isolation of bletistrin G ( 2 ) from rhizomes of Bletilla striata and disclosed its structure [ 7 ].…”

Section: Resultsmentioning

confidence: 71%

“…Plants from the orchid family have been widely used in the traditional Chinese medicine (TCM) and oriental folk medicines to treat tumors, burns, frostbite, coughs, tuberculosis, bronchitis and gastrointestinal bleeding, as well as to remove “heat and toxin” [ 1 ]. According to previous reports, extracts from a variety of different terrestrial orchids contain remarkable amounts of stilbenes and dihydrostilbenes, such as dihydro-resveratrol ( 3 ), moscatilin ( 4 ), resveratrol ( 5 ) and combretastatin A-4 ( 6 ) [ 2 , 3 , 4 , 5 , 6 , 7 , 8 ], which are known to exhibit antineoplastic, antimitotic and anticarcinogenic properties as well as inhibit oxidative stress ( Figure 1 ) [ 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 ]. The structurally unprecedented dihydrostilbenes shancigusin C ( 1 ) and bletistrin G ( 2 ), both featuring 4-hydroxybenzyl substituents, were isolated from the orchidaceous species Pleione yunnanensis and Bletilla striata in 2009 and 2019, respectively [ 6 , 7 ].…”

Section: Introductionmentioning

confidence: 99%

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Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G

et al. 2021

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The biological activities of shancigusin C (1) and bletistrin G (2), natural products isolated from orchids, are reported along with their first total syntheses. The total synthesis of shancigusin C (1) was conducted by employing the Perkin reaction to forge the central stilbene core, whereas the synthesis of bletistrin G (2) was achieved by the Wittig olefination followed by several regioselective aromatic substitution reactions. Both syntheses were completed by applying only renewable starting materials according to the principles of xylochemistry. The cytotoxic properties of shancigusin C (1) and bletistrin G (2) against tumor cells suggest suitability as a starting point for further structural variation.

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Section: Resultsmentioning

confidence: 71%

Section: Introductionmentioning

confidence: 99%

Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G

et al. 2021

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“…Despite polysaccharide analysis, which plays a key role in the authentication of several Chinese herbal medicines (Chen et al, 2012; Lai et al, 2018; Wang et al, 2020). B. striata contains additional small molecules such as bibenzyls (Jiang et al, 2019), phenanthrenes (Guo et al, 2017), stilbenes, ethers (Guo et al, 2017; Masae et al, 1992) and anthocyanins. Moreover, metabolomics technologies for the detection of small molecular compounds in medicines have become increasingly popular for the identification of medicinal plants (Wang, Zhang, et al, 2014; Wu et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

Screening ofBletilla striata,Bletilla ochraceaandOreorchis foliosadifferential metabolites based on metabolomics

Niu

et al. 2022

Biomedical Chromatography

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As a representative medicinal plant in the Orchidaceae, Bletilla striata plays a variety of pharmacological roles in the clinic. However, the emergence of counterfeit species is affecting the basic medicinal materials source identification process, for which Bletilla ochracea and Oreorchis foliosa of the Orchidaceae are two representative species. For this study, 13 representative B. striata samples, three B. ochracea samples and three O. foliosa samples were selected for the systematic determination of polysaccharide yields and monosaccharide composition, and further detection of secondary metabolites by HPLC–MS. The results revealed that there was a significant difference in the yields of polysaccharides between B. striata and B. ochracea (p = 0.006). Although the polysaccharides of both species were composed of glucose and mannose, the molar ratio of the two monosaccharides was different, suggesting that the structures of the polysaccharides were different. The metabolomics results showed that there were no differences in the types of metabolites between B. striata and B. ochracea; however, there were differences in the contents of these metabolites. Although there was no significant difference in the polysaccharide yields of B. striata and O. foliosa (p = 0.074) and the monosaccharide composition was the same (glucose and mannose), many different metabolites were screened out between them: six compounds such as C36H34O11 existed only in B. striata, while substance C39H54O22 was unique to O. foliosa. Therefore, based on the analysis of the polysaccharide content and monosaccharide composition, combined with phase metabolomics research, a preliminary distinction between B. striata, B. ochracea and O. foliosa was achieved.

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“…Some of these compounds showed a wide range of biological activities like antibacterial, anti-inflammatory, neuroprotective, anticancer, and antiviral effects ( Qian et al, 2015 ; Wang and Meng, 2015 ; Xu et al, 2019 ; Jiang et al, 2020 ; Jiang et al, 2021 ). In our previous work, more than 40 stilbenes including 13 new compounds were isolated from the tubers of B. striata and just tested for their antibacterial effects ( Jiang et al, 2019a , Jiang et al, 2019b ).…”

Section: Introductionmentioning

confidence: 99%

Bioactive Bibenzyl Enantiomers From the Tubers of Bletilla striata

Jiang

Chen

et al. 2022

Front. Chem.

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Six new bibenzyls (three pairs of enantiomers), bletstrins D–F (1–3), were isolated from the ethyl acetate-soluble (EtOAc) extract of tubers of Bletilla striata (Thunb.) Rchb f. Their structures, including absolute configurations, were determined by 1D/2D NMR spectroscopy, optical rotation value, and experimental electronic circular dichroism (ECD) data analyses, respectively. Compounds 1–3 possess a hydroxyl-substituted chiral center on the aliphatic bibenzyl bridge, which represented the first examples of natural bibenzyl enantiomers from the genus of Bletilla. The antibacterial, antitumor necrosis factor (anti-TNF-α), and neuroprotective effects of the isolates have been evaluated. Compounds 3a and 3b were effective against three Gram-positive bacteria with minimum inhibitory concentrations (MICs) of 52–105 μg/ml. Compounds 2a and 2b exhibited significant inhibitory effects on TNF-α-mediated cytotoxicity in L929 cells with IC50 values of 25.7 ± 2.3 μM and 21.7 ± 1.7 μM, respectively. Subsequently, the possible anti-TNF-α mechanism of 2 was investigated by molecular docking simulation. Furthermore, the neuroprotective activities were tested on the H2O2-induced PC12 cell injury model, and compounds 2b, 3a, and 3b (10 μM) could obviously protect the cells with the cell viabilities of 57.86 ± 2.08%, 64.82 ± 2.84%, and 64.11 ± 2.52%, respectively.

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Antibacterial bibenzyl derivatives from the tubers of Bletilla striata

Cited by 34 publications

References 29 publications

Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G

Xylochemical Synthesis and Biological Evaluation of Shancigusin C and Bletistrin G

Screening ofBletilla striata,Bletilla ochraceaandOreorchis foliosadifferential metabolites based on metabolomics

Bioactive Bibenzyl Enantiomers From the Tubers of Bletilla striata

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