Anti-inflammatory prenylbenzaldehyde derivatives isolated from Eurotium cristatum

Zhang, Panpan; Jia, Chunxiu; Deng, Yanlian; Chen, Senhua; Чэн, Бин; Yan, Sujun; Li, Jing; Liu, Lan

doi:10.1016/j.phytochem.2018.11.017

Cited by 21 publications

(23 citation statements)

References 22 publications

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“…During the process of pulmonary diseases, inflammatory reaction plays an important role (Welbourn and Young, 1992; Ghio and Devlin, 2001; Ricard et al, 2001; Peng et al, 2004; Menezes et al, 2005). Many preliminary studies confirmed the anti-inflammatory and immune-regulatory effects of natural products, while several data showed a decreased effect of their metabolites on cytokines for inflammation, such as IL-1, IL-6, and TNF-α (Teng et al, 2016, Teng et al, 2017; Chen et al, 2018, Chen et al, 2019; Gupta et al, 2019; Magalhães et al, 2019; Saudagar and Saokar, 2019; Su et al, 2019; Zhang et al, 2019). Hence, it arouses our interest that whether MXD, a famous traditional Chinese medicine formula widely used in respiratory diseases, can alleviate PM2.5 induced lung injury.…”

Section: Discussionmentioning

confidence: 94%

Ma Xing Shi Gan Decoction Attenuates PM2.5 Induced Lung Injury via Inhibiting HMGB1/TLR4/NFκB Signal Pathway in Rat

et al. 2019

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Ma Xing Shi Gan Decoction (MXD), a classical traditional Chinese medicine prescription, is widely used for the treatment of upper respiratory tract infection. However, the effect of MXD against particulate matters with diameter of less than 2.5 μm (PM2.5) induced lung injury remains to be elucidated. In this study, rats were stimulated with PM2.5 to induce lung injury. MXD was given orally once daily for five days. Lung tissues were harvested to assess pathological changes and edema. Myeloperoxidase (MPO) activity and malonaldehyde (MDA) content in lung were determined to evaluate the degree of injury. To assess the barrier disruption, the bronchoalveolar lavage fluid (BALF) was collected to determine the total protein content and count the number of neutrophils and macrophages. For evaluating the activation of macrophage in lung tissue, CD68 was detected using immunohistochemistry (IHC). The levels of inflammatory factors including tumor necrosis factor-alpha (TNF-α), interleukin-1beta (IL-1β), and interleukin-6 (IL-6) in BALF and serum were measured. In vitro, a PM2.5-activated RAW 264.7 macrophages inflammatory model was introduced. To evaluate the protective effect of MXD-medicated serum, the cell viability and the release of inflammatory factors were measured. The effects of MXD on the High mobility group box-1/Toll-like receptor 4/Nuclear factor-kappa B (HMGB1/TLR4/NFκB) pathway in lung tissue and RAW 264.7 cells were assessed by Western blot. For further confirming the protective effect of MXD was mediated by inhibiting the HMGB1/TLR4/NFκB pathway, RAW 264.7 cells were incubated with MXD-medicated serum alone or MXD-medicated serum plus recombinant HMGB1 (rHMGB1). MXD significantly ameliorated the lung injury in rats, as evidenced by decreases in the pathological score, lung edema, MPO activity, MDA content, CD68 positive macrophages number, disruption of alveolar capillary barrier and the levels of inflammatory factors. In vitro, MXD-medicated serum increased cell viability and inhibited the release of inflammatory cytokines. Furthermore, MXD treatment was found to inhibit HMGB1/TLR4/NFκB signal pathway both in vivo and in vitro. Moreover, the protection of MXD could be reversed by rHMGB1 in RAW 264.7. Taken together, these results suggest MXD protects rats from PM2.5 induced acute lung injury, possibly through the modulation of HMGB1/TLR4/NFκB pathway and inflammatory responses.

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Section: Discussionmentioning

confidence: 94%

Ma Xing Shi Gan Decoction Attenuates PM2.5 Induced Lung Injury via Inhibiting HMGB1/TLR4/NFκB Signal Pathway in Rat

et al. 2019

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“…Polyphenols of Fuzhuan Brick‐Tea are less than crude materials due to fermentation procedures (Zhu et al., 2015), and some new triterpenoids and acyl glycosides flavones were discussed in Fuzhuan Brick‐Tea (Ling et al., 2010; Lu et al., 2019). As reported, chemical components discovered in Eurotium cristatum include glycosides, anthraquinone derivatives, indole diketopiperazine derivatives (Du, Li, Li, Zhu, & Wang, 2017; Du, Li, Song, Li, & Wang, 2014; P. Zhang et al., 2019). In addition, lipids are an important group of substances in microorganism, due to the phospholipid membranes of organelles (Stubiger et al., 2016; C. Zhang & Liu, 2019).…”

Section: Introductionmentioning

confidence: 91%

The hypoglycemic effect of extract/fractions from Fuzhuan Brick‐Tea in streptozotocin‐induced diabetic mice and their active components characterized by LC‐QTOF‐MS/MS

Xiang

Jin

et al. 2020

Journal of Food Science

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Fuzhuan Brick‐Tea is a postfermented product with the hypoglycemic effect, which is prepared from the leaves of Camellia sinensis var. sinensis. However, the material basis associated with the hypoglycemic effect was not clear. The present research was designed to explore the hypoglycemic effect of extract/fractions from Fuzhuan Brick‐Tea in streptozotocin‐induced type II diabetic mice. Then an ultra‐high pressure liquid chromatography along with quadrupole time of flight mass spectrometry was used to analyze the phytochemicals in Fuzhuan Brick‐Tea fractions. As a result, the hypoglycemic and hypolipidemic effects were evidently observed from the serum biochemical indexes and liver pathological examination in type II diabetic mice. In addition, there were total of 20 major components including eight lysophosphatidylcholines (Lyso‐PCs), five fatty acids, and seven novel theophylline derivatives tentatively identified in the active fraction from water extract. Therefore, these components were assumed to contribute partly to the hypoglycemic effect of Fuzhuan Brick‐Tea. These findings also give the evidence that the Lyso‐PCs, fatty acids, and novel theophylline derivatives in Fuzhuan Brick‐Tea may provide benefits in ameliorating disorders of glucose and lipid metabolism. Practical Application This study suggests that the Lyso‐PCs, fatty acids, and novel theophylline derivatives in Fuzhuan Brick‐Tea may provide benefits in ameliorating disorders of glucose and lipid metabolism. It can be taken as a beneficial diet additive or nutraceutical.

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“…Structural analysis shows these natural products are composed of prenyl moieties from prenyl diphosphate and indole or indoline rings from tryptophan [ 8 , 9 , 10 , 11 ]. Fungi are the most prolific producers that biosynthesize a family of prenylated secondary metabolites with significant biologic and pharmacological activities, such as antifungal [ 12 ], antibacterial [ 13 , 14 ], antiviral [ 15 ], anti-inflammatory [ 16 ] and antitumor activities [ 17 ]. Among so many biologic activities, their antitumor, antibacterial and antifungal activities are the most prominent.…”

Section: Introductionmentioning

confidence: 99%

C7-Prenylation of Tryptophan-Containing Cyclic Dipeptides by 7-Dimethylallyl Tryptophan Synthase Significantly Increases the Anticancer and Antimicrobial Activities

Zhang

et al. 2020

Molecules

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Prenylated natural products have interesting pharmacological properties and prenylation reactions play crucial roles in controlling the activities of biomolecules. They are difficult to synthesize chemically, but enzymatic synthesis production is a desirable pathway. Cyclic dipeptide prenyltransferase catalyzes the regioselective Friedel–Crafts alkylation of tryptophan-containing cyclic dipeptides. This class of enzymes, which belongs to the dimethylallyl tryptophan synthase superfamily, is known to be flexible to aromatic prenyl receptors, while mostly retaining its typical regioselectivity. In this study, seven tryptophan-containing cyclic dipeptides 1a–7a were converted to their C7-regularly prenylated derivatives 1b–7b in the presence of dimethylallyl diphosphate (DMAPP) by using the purified 7-dimethylallyl tryptophan synthase (7-DMATS) as catalyst. The HPLC analysis of the incubation mixture and the NMR analysis of the separated products showed that the stereochemical structure of the substrate had a great influence on their acceptance by 7-DMATS. Determination of the kinetic parameters proved that cyclo-l-Trp–Gly (1a) consisting of a tryptophanyl and glycine was accepted as the best substrate with a KM value of 169.7 μM and a turnover number of 0.1307 s−1. Furthermore, docking studies simulated the prenyl transfer reaction of 7-DMATS and it could be concluded that the highest affinity between 7-DMATS and 1a. Preliminary results have been clearly shown that prenylation at C7 led to a significant increase of the anticancer and antimicrobial activities of the prenylated derivatives 1b–7b in all the activity test experiment, especially the prenylated product 4b.

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Anti-inflammatory prenylbenzaldehyde derivatives isolated from Eurotium cristatum

Cited by 21 publications

References 22 publications

Ma Xing Shi Gan Decoction Attenuates PM2.5 Induced Lung Injury via Inhibiting HMGB1/TLR4/NFκB Signal Pathway in Rat

Ma Xing Shi Gan Decoction Attenuates PM2.5 Induced Lung Injury via Inhibiting HMGB1/TLR4/NFκB Signal Pathway in Rat

The hypoglycemic effect of extract/fractions from Fuzhuan Brick‐Tea in streptozotocin‐induced diabetic mice and their active components characterized by LC‐QTOF‐MS/MS

C7-Prenylation of Tryptophan-Containing Cyclic Dipeptides by 7-Dimethylallyl Tryptophan Synthase Significantly Increases the Anticancer and Antimicrobial Activities

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