Nigegladines A–C, Three Thymoquinone Dimers from <i>Nigella glandulifera</i>

Tian, Jie; Han, Chao; Guo, Wenhua; Yin, Yong; Wang, Xiaobing; Sun, Hongbin; Yao, Hequan; Yang, Yue; Wang, Chen; Liu, Chang; Yang, Ming‐Hua

doi:10.1021/acs.orglett.7b03189

Cited by 15 publications

(13 citation statements)

References 17 publications

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“…This effect was therefore equal to that of the positive control, verapamil (Supporting Information Figure S2). , To elucidate its hypoxia-protective mechanism against H/R-induced cell death, HUVECs were pretreated with 2 and were analyzed for their apoptotic signals through flow cytometry using annexin V–FlTC/PI staining. Compared to the apoptotic percentages of the control group, hypoxia/reoxygenation successfully induced cell apoptosis in the model group.…”

Section: Resultsmentioning

confidence: 99%

“…In our ongoing search for new antioxidant and antihypoxic compounds, − the endophytic strain Peyronellaea glomerata attracted our attention; a crude extract showed a half-maximal effective concentration (EC 50 ) of 187.5 μM in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. Moreover, azaphilone analogues are known to be produced by P. glomerata , which were suggested to be present by UV characteristics during HPLC analysis.…”

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confidence: 99%

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Hypoxia-Protective Azaphilone Adducts from Peyronellaea glomerata

Liu

Wang

et al. 2018

J. Nat. Prod.

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Peyronellones A and B (1 and 2), a pair of rare tetracyclic caged adducts of azaphilone with pyruvic acid, along with four new analogues (3-6), were isolated from solid cultures of the endophytic fungus Peyronellaea glomerata. Their structures were elucidated through spectroscopic analysis, and their absolute configurations were unambiguously determined by a combination of single-crystal X-ray crystallography, Rh(OCOCF)-induced ECD experiments, ECD calculations, and modified Mosher methods. Compound 2 (5 μM) was found to have a significant hypoxia-protective effect that improved the survival rate of hypoxia/reoxygenation-treated human umbilical vein endothelial cells from 35% to 70%, which was equal to the potency of the positive control, verapamil. Flow cytometry analysis suggested 2 could inhibit H/R-induced late-stage apoptosis of this cell line.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Hypoxia-Protective Azaphilone Adducts from Peyronellaea glomerata

Liu

Wang

et al. 2018

J. Nat. Prod.

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“…Due to its convergency, this reaction exemplifies themes of step and atom economy . Furthermore, the ease of postsynthetic modifications by selective functional group interconversions renders this reaction practical for diversity-oriented synthesis, an increasingly important strategy in drug discovery …”

Section: Discussionmentioning

confidence: 99%

Pd(0)-Catalyzed Chemo-, Diastereo-, and Enantioselective α-Quaternary Alkylation of Branched Aldehydes

et al. 2020

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Quaternary carbon stereocenters are ubiquitous in a wide variety of organic compounds and drug molecules. Highly enantioselective construction of such quaternary carbon centers poses a singular challenge due to the steric repulsion between the four different carbon substituents. Herein, we report a novel strategy to control the enantioselective construction of chiral α-quaternary aldehydes from racemic α-branched aldehydes. Distinct from the established chiral α-quaternary aldehyde synthesis, this project employed a chiral π-allyl–Pd complex neighboring the enolate to determine both the enantio- and diastereoselectivity. The synthetic utility of the products has been highlighted by a series of derivatizations, and the potential of this method has been extended to the synthesis of chiral α-quaternary ketones. Furthermore, this reaction exemplifies the themes of step and atom economy, in addition to the principles of diversity-oriented synthesis.

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“…Novel dolabellane-type diterpene alkaloids 17-26 were also rare in nature [12][13][14]. In addition, compounds 30-32 with unprecedented skeletons could be speculated to derive from the dimerization of thymoquinone (TQ) [18]. Notably, to date, natural indazole-type alkaloids have only been obtained from species of the genus Nigella and therefore considered as possible taxonomic markers in Nigella genus plants.…”

Section: Alkaloidsmentioning

confidence: 99%

“…e effect was comparable with verapamil, which was known for its protective effect on cardiomyocytes. [18]. A study showed the protective effects of TQ on the cardiac damage in BALB/c mice.…”

Section: Cardiovascular Activity and Vessel Protectionmentioning

confidence: 99%

Recent Progress on Chemical Constituents and Pharmacological Effects of the Genus Nigella

Niu

Zhou

Meng

et al. 2020

Evidence-Based Complementary and Alternative Medicine

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Seeds of the genus Nigella plants as folk medicine are often used to prevent and treat asthma, diarrhea, dyslipidemia, and other diseases around the world. Pharmacological researches showed that seed extract and seed oil have antibacterial, antioxidant, hypoglycemic, and hepatoprotective effects which attributed to their bioactive constituents such as alkaloids, saponins, flavones, and phenols. This paper has covered recent progresses on chemical and pharmacological researches on these plants, including their compounds and pharmacological effects. It was found that the chemical component researches were focused on the seed oil. Therefore, more attention should be paid to the profile of the whole constituents in the seeds.

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Nigegladines A–C, Three Thymoquinone Dimers from Nigella glandulifera

Cited by 15 publications

References 17 publications

Hypoxia-Protective Azaphilone Adducts from Peyronellaea glomerata

Hypoxia-Protective Azaphilone Adducts from Peyronellaea glomerata

Pd(0)-Catalyzed Chemo-, Diastereo-, and Enantioselective α-Quaternary Alkylation of Branched Aldehydes

Recent Progress on Chemical Constituents and Pharmacological Effects of the Genus Nigella

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