RSC Advances
·
2022
·Vol. 12
·期 42
·27550-27554
·
IF 4.036
Yuanyuan Xu,Dan Li,Wenxuan Wang,Kangping Xu,Guishan Tan,Jing Li,Shu-Ming Li,Xia Yu
Prenylation usually improves structural diversity and bioactivity in natural products. Unlike the discovered enzymatic gem-diprenylation of mono- and tri-cyclic aromatic systems, the enzymatic approach for gem-diprenylation of bi-cyclic hydroxynaphthalenes is new to science. Here we report an enzymatic example for dearomative C4 gem-diprenylation of α-hydroxynaphthalenes, by the F253G mutant of a fungal prenyltransferase CdpC3PT. Experimental evidence suggests a sequential electrophilic substitution mechanism. We also explained the alteration of catalytic properties on CdpC3PT after mutation on F253 by modeling. This study provides a valuable addition to the synthetic toolkit for compound prenylation and it also contributes to the mechanistic study of prenylating enzymes.
研究领域:
生物化学
·
酶学
·
有机化学
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DOI
PubMed
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2020
·
IF 5.162
Jiali Yang,Ting Zhou,Yueming Jiang,Bao Yang
Prenylated flavonoids are good drug candidates due to multiple biological activities and health benefits. Prenyltransferase is an important enzyme involved in the biosynthesis of prenylated flavonoids. In this work, a flavonoid prenyltransferase (AhPT1) from Artocarpus heterophyllus showed an unexpectedly metal ion-induced specificity to flavonoid substrates. AhPT1 could catalyse 6- C -prenylation of genistein when Mg 2+ serving as cofactor. Its catalytic activity to 6-hydroxyflavone was undetectable. However, when Mn 2+ was used instead of Mg 2+ , 5- C -prenylated 6-hydroxyflavone was generated with a high conversion rate. Mn 2+ altered the regiospecificity of AhPT1 and turned it into a 5- C -prenyltransferase. 2′-Hydroxyl could improve the conversion rate of 6-hydroxyflavone, whereas 3′- or 4′-hydroxyl impaired the catalysis efficiency of AhPT1. NQIFDADID174 and DLTDVEGD305 were active motifs involved in substrate binding and catalysis. Asn166, Asp170, Asp174, Asp298, Asp301 and Asp305 in the active center were critical to the prenylation reaction.
研究领域:
生物化学
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酶学
·
药理学
✓ 已验证
DOI
PubMed
高影响因子
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS
·
2022
·
IF 3.322
Ting Zhou,Bao Yang
Prenylated resveratrols are drug candidates presented in many natural sources. They possess multiple pharmacological activities. Due to the limited abundance in nature and disadvantage of chemical synthesis, it is required to produce prenylated resveratrols by biological strategy. In this work, a prenyltransferase iacE from Pestalotiopsis fici was prepared by heterologous overexpression. It could catalyze 2- C -prenylation of resveratrol efficiently. Dimethylallyl diphosphate (DMAPP) and geranyl diphosphate (GPP) could serve as prenyl donor. Glu97, Thr114 and Tyr413 were proved to be important residues in the active site by site-directed mutagenesis. The product was purified and identified to be 2- C -prenyl resveratrol by NMR . 2- C -prenyl resveratrol exerted neuroprotective activity through inhibiting ROS overproduction and improving the activities of antioxidant enzymes in HT22 cell. The genes involved in antioxidant defense were regulated, including upregulated CAT , SOD2 , NFE2L2 , GPx4 , and downregulated PTGS2 and ACSL4 . These results supplied a novel technique for prenylated resveratrols production.
研究领域:
生物技术
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药理学
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神经科学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
·
2025
·
IF 3.5
Zhengjiao Gao,Dingtao Tang,Bingfeng He,Jiajie Quan,Zhengke Zhang,Yueming Jiang,Bao Yang,Jiali Yang
BACKGROUND Prenylated flavonoids are widely distributed in plants, including fruits and vegetables in the Moraceae and Fabaceae families. These chemicals are potential functional food ingredients owing to their attractive biological activities. However, natural prenylated flavonoids are rare, which limits their application. RESULTS Here, we reported the prenylation of apigenin and genistein catalyzed by DMATS1, a dimethylallyl- l -tryptophan synthase from Fusarium fujikuroi . High-performance liquid chromatography–tandem mass spectrometry and nuclear magnetic resonance identified their structure as 6- C -prenylapigenin (6-PA) and 6- C -prenylgenistein (6-PG), respectively. Cell-based assay suggested that both 6-PA and 6-PG induced the proliferation of THP-1 cells under low concentrations and were safe in doses less than 50 μmol L −1 . 6-PA and 6-PG exhibited significant anti-inflammatory activity in lipopolysaccharide-stimulated THP-1 cells, and inhibited the production of nitric oxide as well as downregulating the transcriptional levels of pro-inflammatory cytokines, including tumor necrosis factor-α, interleukin-8, and interleukin-1β. CONCLUSION The findings suggested that DMATS1 could catalyze the 6- C prenylation of apigenin and genistein, and the generated 6-PA and 6-PG exhibited anti-inflammatory activity, aiding in the recognition of 6-PA and 6-PG as nutraceuticals. © 2025 Society of Chemical Industry.
CAS / MDL:
研究领域:
植物化学
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药理学
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生物合成
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产品关联
DOI
PubMed
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2019
·
IF 4.784
Tao Zheng,Dingming Zhong,Dafeng Zheng,Fengli Bao,Jianmin Zheng,Xueqing Qiu
In order to develop a biomass-based superplasticizer, kraft lignin (KL) was grafted with isopentenol polyoxyethylene ether (TPEG) to prepare a novel macromonomer (KL-TPEG). It was shown that the retention ratio of the aliphatic C C bond increased from 81.07% to 90.20% with the increase of m(TPEG)/m(KL). When the grafting ratio was increased, the average number of TPEG grafted on one KL molecule was approximately 1.4, 3.1, 4.6, 6.2 and 7.6. The star-like structure was also confirmed by FT-IR, 1 H NMR and GPC. KL-TPEG had favorable surface activity and dispersion stability on the cement particles. It was illustrated that the shear stress and shear viscosity of the cement slurries with KL-TPEG were significantly less than that of blank slurry. The dispersion-retention ability of KL-TPEG on the slurry was also gradually enhanced with the increase of the grafting ratio of TPEG. It was seldom reported on the biomass-based TPEG. Through modified with KL, the rheology behavior and the dispersion-retention ability of TPEG was greatly improved, and the cost of TPEG was also reduced, thus this study not only promoted the development of biomass-based macromonomer, but also helped for the high value utilization of lignin.
研究领域:
材料科学
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生物质化学
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产品关联
DOI
PubMed
高影响因子
BIOMEDICAL CHROMATOGRAPHY
·
2021
·Vol. 36
·期 1
·e5239
·
IF 1.902
Xiao-fang Ma,Qi Zhao,Yan Cheng,Dong-Mei Yan,Wei-Feng Zhu,Fei Li
Coumarins are a group of natural compounds commonly found in the families of Rutaceae and Umbelliferae. 7-Isopentenyloxycoumarin (ISC), auraptene (AUR), and umbelliprenin (UM) belong to prenyloxycoumarins (PYCs), which link isopentenyl, geranyl, and farnesyl group at C7 position, respectively. The substituent of 7-ethoxycoumarin (ETC) is the ethyl group. In this study, UPLC–ESI–QTOF–MS (ultra-performance liquid chromatography–electrospray ionization–quadrupole time of flight–MS)-based metabolomics was used to evaluate the in vivo and in vitro metabolism of PYCs. Results showed that ETC produced 10 known metabolites, and ISC was transformed into 17 metabolites in vivo and in vitro , which were undescribed compounds. A total of 35 AUR metabolites, including 34 undescribed metabolites were identified, and 21 metabolites were reported for the first time in UM. The results indicated that hydroxylation and N -acetylcysteine conjugation were the common metabolic reactions for PYCs. The metabolic rates of ETC, ISC, AUR and UM were 26%, 36%, 81%, and 38%, respectively, in human liver microsome, while they were 24%, 40%, 80%, and 37%, respectively, in mouse liver microsomes. In addition, recombinant cytochrome P450s (CYPs) screening showed that CYP1A1, 2C19, 3A4, and 3A5 were the major metabolic enzymes involved in the formation of hydroxylation metabolites. Together, these results suggest that the isopentenyl group plays an important role in the metabolism of PYCs.
研究领域:
药理学
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植物化学
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代谢研究
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产品关联
DOI
PubMed
高影响因子
METABOLIC ENGINEERING
·
2020
·
IF 7.263
Tianyuan Hu,Jiawei Zhou,Yuru Tong,Ping Su,Xinlin Li,Yuan Liu,Nan Liu,Xiaoyi Wu,Yifeng Zhang,Jiadian Wang,Linhui Gao,Lichan Tu,Yun Lu,Zhouqian Jiang,Yongjin J. Zhou,Wei Gao,Luqi Huang
Miltiradiene is a key intermediate in the biosynthesis of many important natural diterpene compounds with significant pharmacological activity, including triptolide, tanshinones, carnosic acid and carnosol. Sufficient accumulation of miltiradiene is vital for the production of these medicinal compounds. In this study, comprehensive engineering strategies were applied to construct a high-yielding miltiradiene producing yeast strain. First, a chassis strain that can accumulate 2.1 g L -1 geranylgeraniol was constructed. Then, diterpene synthases from various species were evaluated for their ability to produce miltiradiene, and a chimeric miltiradiene synthase, consisting of class II diterpene synthase (di-TPS) Cf TPS1 from Coleus forskohlii ( Plectranthus barbatus ) and class I di-TPS Sm KSL1 from Salvia miltiorrhiza showed the highest efficiency in the conversion of GGPP to miltiradiene in yeast. Moreover, the miltiradiene yield was further improved by protein modification, which resulted in a final yield of 550.7 mg L -1 in shake flasks and 3.5 g L -1 in a 5-L bioreactor . This work offers an efficient and green process for the production of the important intermediate miltiradiene, and lays a foundation for further pathway reconstruction and the biotechnological production of valuable natural diterpenes.
研究领域:
生物工程
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药学
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合成生物学
✓ 已验证
DOI
PubMed
高影响因子
Journal of Flow Chemistry
·
2025
·
IF 2
Zhao Hang,Xiao Xiao,Hao Runqi,Chen Dan,Ke Jiawei,Liu Minjie,Wan Li,Chen Fener
1-Chloro-3-methyl-2-butene is an important synthetic precursor or alkylating agent in the preparation of various bioactive chemicals and essential nutrients for human beings. A flow surface-mediated HCl in situ generation and subsequent hydrochlorination of isoprene were realized in the PTFE tubing reactor and the packed-bed reactor separately. Up to 86% isolated yield of 1-chloro-3-methyl-2-butene was achieved in the packed-bed reactor by performing the flow hydrochlorination at -15 °C within a 15 min residence time in the presence of 0.5 equiv. SOCl 2 . The in-line recycling and regenerating of solid proton donor Al 2 O 3 were accomplished via simple washing with DCM and MeOH in sequence, the activity of Al 2 O 3 filled in the packed-bed reactor maintain consistent on the isolated yield of 1-chloro-3-methyl-2-butene after ten times consecutive reutilization. The flow platform consisting of two parallel packed-bed reactors were assembled for the continuous synthesis of desired 1-chloro-3-methyl-2-butene without interruption through delicate coordinating opening direction of a series of three-way valves. Long-term stability and reliability were demonstrated by continuous running the designed cyclic rotation system for 10 h, the targeted hydrochlorination product was furnished in 91–93% yield. Graphical abstract Continuous-flow synthesis of prenyl chloride was enabled by cross-sequential utilization strategy using two parallel packed-bed reactors and precise alternating a series of three-way valves opening direction.
研究领域:
有机化学
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合成化学
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产品关联
DOI
高影响因子
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
·
2024
·
IF 3.8
Yuehua Xiao,Chengtao Wang,Jiale Xiao,Hangjie Li,Zhengxing Cui,Yeqing Wang,Liang Wang,Feng-Shou Xiao
Oligomerization of alkenes is a promising way for production of high-quality and eco-friendly liquid fuels, where zeolite catalysts are critical. In the zeolite catalysts, mass transfer and accessibility in the reaction are normally influenced by intrinsic micropores of zeolites, in particular, bulky or branched molecules are employed. Here, we report isoamylene (2-methyl-2-butene) dimerization over mesoporous HY zeolites obtained by facile NaOH treatments. These mesoporous HY zeolites exhibited high activity and good stability for the isoamylene dimerization compared with untreated HY zeolite. Powder XRD patterns, N2 physisorption, SEM, TEM, NMR, FTIR, and NH3-TPD techniques were used to characterize the porosity and acidity of the zeolites. These results showed that mass transfer and accessibility to the acid sites of the guest molecules are the key factors for the improvement of catalytic performances.
研究领域:
化学工程
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催化材料科学
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产品关联
DOI
高影响因子
CANADIAN JOURNAL OF CHEMICAL ENGINEERING
·
2022
·Vol. 101
·期 7
·3813-3820
·
IF 2.5
Rong Xu,Qingming Song,Chuang Li,Junfeng Li,Hongjun Yang,Jian Chen,Zhipeng Mao
2-Chloro-2-methylbutane is an important organic compound widely used as a starting material in organic synthesis. It is mainly produced by the addition reaction of isoamylene and hydrochloric acid. As a raw material, isoamylene has a low boiling point and an extremely low flash point, making it a high-risk material in large-scale industrial productions. In this paper, a highly efficient production of 2-Chloro-2-methylbutane was realized using a continuous flow micro-channel reactor. Through the back pressure system of the reactor, the fluid pressure was increased, which elevated the reaction temperature, and enhanced the rate of reaction. The obtained optimal reaction conditions for the process were a reaction temperature of 90°C, pressure of 0.67 MPa, residence time of reactants of 15 min, n (hydrochloric acid): n (isoamylene) = 2.80:1.00, and v (hydrochloric acid): v (isoamylene) = 4.40:1.76. Compared with a batch process, the micro-channel process significantly shortened the reaction time and conversion a continuous and an efficient production. Computational analysis using computational fluid dynamics (CFD) simulation software was used to simulate the two-phase flow in the micro-channel reactor, and the results were consistent with the experimental results.
研究领域:
有机化学
·
化工工程
✓ 已验证
产品关联
DOI
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2021
·
IF 5.279
Cong Qiu,Yang Liu,Yangbao Wu,Linguo Zhao,Jianjun Pei
Prenyl groups increase the lipophilicity of flavonoids, endowing them with a special activity, selectivity, and pharmacological properties by prenylation. Herein, a novel prenyltransferase (ShFPT) gene from Streptomyces sp. NT11 was expressed in Escherichia coli, and its biochemical characteristics were determined. ShFPT exhibited high selectivity to prenylate naringenin at C-6 to generate 6-prenylnaringenin. The optimal activity was observed at pH 6.0 and 55 °C. The Kcat and Km for naringenin were 0.0095 s–1 and 0.20 mM, respectively. Several promiscuous kinase and isopentenyl phosphate kinase genes were screened to develop the most efficient dimethylallyl diphosphate (DMAPP) synthesis pathway for 6-prenylnaringenin synthesis in E. coli. The 6-prenylnaringenin production was improved by changing the induction strategies and optimizing the bioconversion conditions. Finally, 6-prenylnaringenin production reached the highest yield of 69.9 mg/L with average productivity of 4.0 mg/L/h after 16 h incubation, which is the highest yield for any prenylated flavonoid reported to date in E. coli. Therefore, this study provides an efficient method for 6-prenylnaringenin production and reveals the DMAPP synthesis pathway.
研究领域:
生物化学
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微生物学
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药理学
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产品关联
DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2022
·
IF 9.231
Shengtao Bo,Sui Kiat Chang,Ting Zhou,Hong Zhu,Yueming Jiang,Bao Yang
Prenylated stilbenoids are good candidates of nutraceuticals presented in food resources. The levels of natural prenylated stilbenoids are usually low. Biotransformation is a promising synthesis strategy to produce novel bioactive compounds. However, information regarding biosynthesis of prenylated stilbenoids is rare. In this work, prenyltransferase and geranyl diphosphate biosynthesis pathway were overexpressed in E. coli . Multiple prenyltransferase genes were tested and Ambp1 was found to be effective on resveratrol geranylation. The products were identified by mass spectrometry and nuclear magnetic resonance spectroscopy as 4- C -geranyl resveratrol ( 1 ) and 3- O -geranyl resveratrol ( 2, novel chemical). By optimization of culture conditions, a yield of 36.9% was achieved for the conversion to geranylated resveratrol from resveratrol. These two compounds demonstrated good antioxidant activities with IC 50 values of 28.09 μM for 4- C -geranyl resveratrol and 403.88 μM for 3- O -geranyl resveratrol. The results were helpful for developing novel technique to produce prenylated phenolics.
研究领域:
生物技术
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药物化学
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营养保健品
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产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）