Publications by authors named "Rui-Han Zhang"

15 Publications

  • Page 1 of 1

Leojaponin inhibits NLRP3 inflammasome activation through restoration of autophagy via upregulating RAPTOR phosphorylation.

J Ethnopharmacol 2021 Oct 9;278:114322. Epub 2021 Jun 9.

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, China. Electronic address:

Ethnopharmacological Relevance: Duan Teng Yimu decoction is a Chinese herbal medicine compound with proven therapeutic effects on inflammasome-related diseases, such as rheumatoid arthritis. This decoction consists of three Chinese herbal medicines, including Leonurus japonicus (L. japonicus), which promotes the blood circulation and exhibits detumescence activity, traditionally curing gynecologic and inflammasome diseases.

Aim Of The Study: To explore the anti-inflammasome activity and the underlying mechanisms of action of the compounds from L. japonicus.

Materials And Methods: A series of compounds were isolated from L. japonicus. Their anti-inflammasome activities were evaluated in macrophages that were co-stimulated by lipopolysaccharide (LPS) and NLRP3 inflammasome inducers. NLRP3 inflammasome formation and apoptosis speck like containing a CARD (ASC) oligomerization were evaluated by immunofluorescent microscopy and Western blot analysis. The regulation of autophagy after treatment of this compound was also evaluated. Lastly, in vivo activity of Leojaponin was analyzed in a mouse acute gouty arthritis model.

Results: Here we show that Leojaponin, a diterpenoid compound from L. japonicus, suppressed lactate dehydrogenase and IL-1β release in Nigericin-stimulated macrophages in a pyroptosis model. Leojaponin inhibits NLRP3 inflammasome activation in both J774A.1 cells and bone marrow-derived macrophages in a dose dependent manner. Moreover, Leojaponin suppressed NLRP3-mediated ASC specks formation and ASC oligomerization. These activities of Leojaponin depend on restoration of autophagy via promoting RAPTOR phosphorylation. Furthermore, Leojaponin ameliorated monosodium urate (MSU)-induced acute gouty arthritis in vivo.

Conclusion: Our findings suggest that Leojaponin inhibits NLRP3 inflammasome activation through enhancing autophagy via RAPTOR phosphorylation, thereby highlighting Leojaponin as a potent drug for inflammasome-related diseases.
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http://dx.doi.org/10.1016/j.jep.2021.114322DOI Listing
October 2021

Toonaones A-I, limonoids with NLRP3 inflammasome inhibitory activity from Toona ciliata M. Roem.

Phytochemistry 2021 Apr 14;184:112661. Epub 2021 Jan 14.

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan, 650091, China. Electronic address:

Nine undescribed limonoids, 18(13 → 14)-abeo-15β,21-dihydroxy-24,25,26,27-tetranor-3,7-dioxoapotirucalla-1,9(11),13(17),20(22)-tetraen-23,21-olide (Toonaone A), 21-hydroxy-24,25,26,27-tetranor-3,7,15-trioxoapotirucalla-1,9(11),20(22)-trien-23,21-olide (Toonaone B), 7α,21-dihydroxy-12α-isobutyryl-24,25,26,27-tetranor-3,15-dioxoapotirucalla-1,20(22)-dien-23,21-olide (Toonaone C), 7,8-seco-7-methyl ester-11β-acetoxy-14β,15β-epoxy-21-hydroxy-24,25,26,27-tetranor-3-oxoapotirucalla-1,8(30),20(22)-trien-23,21-olide (Toonaone D), 7,8-seco-7-methyl ester-11β-acetoxy-14β,15β-epoxy-23-hydroxy-24,25,26,27-tetranor-3-oxoapotirucalla-1,8(30),20(22)-trien-21,23-olide (Toonaone E), 7,8-seco-7-methyl ester-11β-acetoxy-14β,15β-epoxy-6β,21-dihydroxy-24,25,26,27-tetranor-3-oxoapotirucalla-1,8(30),20(22)-trien-23,21-olide (Toonaone F), 7,8-seco-7-methyl ester-14β,15β-epoxy-8α,21-dihydroxy-24,25,26,27-tetranor-3-oxoapotirucalla-1,20(22)-dien-23,21-olide (Toonaone G), 7,8-seco-7-methyl ester-14β,15β-epoxy-6β,8α,21-trihydroxy-24,25,26,27-tetranor-3-oxoapotirucalla-1,20(22)-dien-23,21-olide (Toonaone H), 7,8-seco-7-methyl ester-14β,15β-epoxy-6β,8α,21-trihydroxy-24,25,26,27-tetranor-3-oxoapotirucalla-1,20(22)-dien-21,23-diimide (Toonaone I), and five known analogues were isolated from the twigs of Toona ciliata M. Roem. (Meliaceae). Toonaone A possesses the first rare 18(13 → 14)-abeo-limonoid skeleton reported from the genus Toona. Their structures were elucidated using spectroscopic data analyses and quantum chemistry calculations. Biological evaluation showed that toonaone C, toonaone D, toonaone G, toonaciliatavarin F, and toonaciliatavarin G exhibited significant anti-NLRP3 inflammasome activity with IC values ranging from 3.74 to 18.7 μM. GMDMD, IL-1β, and caspase-1 analyses suggested that toonaone D inhibited NLRP3 inflammasome activation and blocked macrophage pyroptosis.
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http://dx.doi.org/10.1016/j.phytochem.2021.112661DOI Listing
April 2021

Rubellawus A-D, Four New Diterpenoids Isolated from Callicarpa rubella and Their Anti-NLRP3 Inflammasome Effects.

Chem Biodivers 2020 Dec 26;17(12):e2000798. Epub 2020 Nov 26.

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Research and Development Center for Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, P. R. China.

Four new diterpenoids, rubellawus A-D (1-4), along with three known compounds, were isolated and identified from the flowers of Callicarpa rubella. Their structures were elucidated by various spectroscopic analysis. All the compounds were screened for their anti-inflammatory activity and 14α-hydroxyisopimaric acid and isopimaric acid showed significant NLRP3 inflammasome inhibitory activity with IC values of 7.02 and 3.99 μM.
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http://dx.doi.org/10.1002/cbdv.202000798DOI Listing
December 2020

Toonaolides A-X, limonoids from Toona ciliata: Isolation, structural elucidation, and bioactivity against NLRP3 inflammasome.

Bioorg Chem 2020 12 10;105:104363. Epub 2020 Oct 10.

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, People's Republic of China. Electronic address:

Twenty-four new limonoids, toonaolides A-X (1-24), characterized with an α,β-unsaturated-γ-lactone A-ring were isolated from the twigs of Toona ciliata. Their structures and absolute configurations were elucidated by spectroscopic data, X-ray diffraction crystallography, and quantum chemistry calculations. Most of the isolated compounds (except 9, 18, and 24 which possessed the maleimide ring) featured the rare 21-hydroxybutenolide or 23-hydroxybutenolide moieties. In particular, compound 1 has an unprecedented limonoid architecture with 6/6 cis-fused A/B ring system and 2 has an unusual tetrahydrofuran ring B skeleton, featuring a 7/5/6/5 ring system. The biological evaluation showed that compounds 9, 11, 12, 14, and 18 exhibited significantly anti-NLRP3 inflammasome activity with IC values ranging from 3.2 to 9.7 μM. Analysis of IL-1β and caspase-1 expression revealed that compounds 11 and 12 are selective inhibitors of NLRP3 inflammasome, which could ameliorate cell pyroptosis by blocking NLRP3 inflammasome activation.
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http://dx.doi.org/10.1016/j.bioorg.2020.104363DOI Listing
December 2020

Euphopias A-C: Three Rearranged Jatrophane Diterpenoids with Tricyclo[8.3.0.0]tridecane and Tetracyclo[11.3.0.0.0]hexadecane Cores from .

Org Lett 2020 10 29;22(20):7820-7824. Epub 2020 Sep 29.

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education; Yunnan Research & Development Center for Natural Products; School of Chemical Science and Technology, Yunnan University, Kunming 650091, P. R. China.

Euphopias A-C (-), three rearranged jatrophane-type diterpenoids with tricyclo[8.3.0.0]tridecane ( and ) and tetracyclo[11.3.0.0.0]hexadecane () cores, were isolated from . Comprehensive spectroscopic analyses, quantum-chemical calculations, and X-ray diffractions were used to identify their structures. Compounds - could significantly inhibit NLRP3 inflammasome activation and block NLRP3 inflammasome-induced pyroptosis. Additionally, a mechanistic study revealed that could ameliorate mitochondria damage, thereby interrupting NLRP3 inflammasome activation.
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http://dx.doi.org/10.1021/acs.orglett.0c02676DOI Listing
October 2020

Design, synthesis and anti-HIV evaluation of 5-alkyl- 6-(benzo[d][1,3]dioxol-5-alkyl)-2-mercaptopyrimidin-4(3H)-ones as potent HIV-1 NNRTIs.

Bioorg Chem 2020 09 26;102:104041. Epub 2020 Jun 26.

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China. Electronic address:

In order to discover and develop the new HIV-1 NNRTIs, a series of 5-alkyl-6-(benzo[d][1,3]dioxol-5-ylalkyl)-2-mercaptopyrimidin-4(3H)-ones was synthesized and screened for their in vitro cytotoxicity against HIV-1. Most of the compounds we synthetized showed high activity against wild-type HIV-1 strain (IIIB) while IC values are in the range of 0.06-12.95 μM. Among them, the most active HIV-1 inhibitor was compound 6-(benzo[d][1,3]dioxol-5-ylmethyl)-5-ethyl-2-((2-(4-hydroxyphenyl)-2-oxoethyl)thio)pyrimidin-4(3H)-one (5b), which exhibited similar HIV-1 inhibitory potency (IC = 0.06 μM, CC = 96.23 μM) compared with nevirapine (IC = 0.04 μM, CC >200 μM) and most of compounds exhibited submicromolar IC values indicating they were specific RT inhibitors. The compounds 5b, 6-(benzo[d] [1,3]dioxol-5-yl)-5-ethyl-2-((2-(4-hydroxyphenyl)-2-oxoethyl)thio)pyrimidin-4(3H)-one (5c) and 4-(2-((4-(benzo[d][1,3]dioxol-5-ylmethyl)-5-ethyl-6-oxo-1,6-dihydropyrimidin-2-yl)thio)acetyl)phenylbenzo[d][1,3]dioxole-5-carboxylate (5r) were selected for further study. It was found that all of them had little toxicity to peripheral blood mononuclear cell (PBMC), and had a good inhibitory effect on the replication of HIV-1 protease inhibitor resistant strains, fusion inhibitor resistant strains and nucleosides reverse transcriptase inhibitor resistant strains, as well as on clinical isolates. Besides, compound 5b and 5c showed inhibition of HIV-1 RT RNA-dependent DNA polymerization activity and DNA-dependent DNA polymerization activity, while compound 5r only showed inhibition of HIV DNA-dependent DNA polymerization activity, which was different from classical reverse transcriptase inhibitors. Our study which offered the preliminary structure-activity relationships and modeling studies of these new compounds has provided the valuable avenues for future molecular optimization.
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http://dx.doi.org/10.1016/j.bioorg.2020.104041DOI Listing
September 2020

Callicarpins, Two Classes of Rearranged -Clerodane Diterpenoids from Plants Blocking NLRP3 Inflammasome-Induced Pyroptosis.

J Nat Prod 2020 07 6;83(7):2191-2199. Epub 2020 Jul 6.

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, People's Republic of China.

Callicarpins A-D (-), possessing an unprecedented A--clerodane scaffold with a bicyclo[5.4.0]undecane ring system, and callicarpins E-G (-), with 5/6-fused -clerodane diterpenoid skeletons, were isolated from and . Their structures were elucidated by comprehensive spectroscopic data, X-ray crystal diffraction, chemical derivatization, and electronic circular dichroism (ECD) data. Putative biosynthetic pathways for these callicarpins are proposed. Compounds , , and - showed potent inhibitory effects against the NLRP3 inflammasome with IC values from 1.4 to 5.3 μM, and significantly blocked NLRP3 inflammasome-induced pyroptosis by inhibiting Casp-1 activation and IL-1β secretion in J774A.1 cells.
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http://dx.doi.org/10.1021/acs.jnatprod.0c00288DOI Listing
July 2020

Controlling the selectivity of an intramolecular Friedel-Crafts alkylation with alkenes using selenium under mild conditions.

Org Biomol Chem 2020 06 19;18(21):4034-4045. Epub 2020 Mar 19.

Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, 650091 China.

An efficiently divergent intramolecular Friedel-Crafts alkylation by unactivated alkenes with seleniranium ion-controlled Markovnikov/anti-Markovnikov specificities under mild conditions has been investigated. 2-Benzoxepin, isochroman, and isochromene can be produced in one-pot procedures from the same substrate in high yields and with high regio- and stereospecificity. The products are challenging to access via 7-endo-trig carbocyclizations and by 7-endo-trig carbocyclization/rearrangement/6-exo-trig oxycyclization and 6-exo-trig carbocyclization/deselenenylation reaction sequences, respectively. Mechanistic experiments indicated that in addition to the stereospecific anti-addition processes of the cyclization reactions, the formation of a stable carbocation after ring opening of the seleniranium ion leads to an NPSP-mediated 7-endo-trig carbocyclization; the steric hindrance of the seleniranium intermediate controls the regioselectivity when using TPSCA at 60 °C, which promotes 6-exo-trig carbocyclization. Two distinct catalytic cycles were proposed, and the structures of transition states and products were identified by ab initio calculations and X-ray analyses.
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http://dx.doi.org/10.1039/d0ob00257gDOI Listing
June 2020

Clerodane diterpenoids with potential anti-inflammatory activity from the leaves and twigs of Callicarpa cathayana.

Chin J Nat Med 2019 Dec;17(12):953-962

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China. Electronic address:

Phytochemical investigation of the leaves and twigs of Callicarpa cathayana led to the isolation of six new clerodane diterpenoids, cathayanalactones A-F (1-6), together with seven analogues (7-13). Their structures were established by extensive NMR analyses together with experimental and calculated ECD spectra analyses. Compounds 1, 2, 3, 7 and 11 showed inhibitory activities on lipopolysaccharide-induced nitric oxide production in RAW264.7 cells.
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http://dx.doi.org/10.1016/S1875-5364(19)30118-9DOI Listing
December 2019

Premnafulvol A: A Diterpenoid with a 6/5/7/3-Fused Tetracyclic Core and Its Biosynthetically Related Analogues from Premna fulva.

Org Lett 2018 10 26;20(19):6314-6317. Epub 2018 Sep 26.

Key Laboratory of Medicinal Chemistry for Natural Resource of Ministry of Education and Yunnan Province, School of Chemical Science and Technology , Yunnan University , Kunming 650091 , China.

Premnafulvol A (1), a unique diterpenoid featuring a 6/5/7/3-fused tetracyclic carbon skeleton, with three biosynthetically related analogues, premnafulvols B-D (2-4), were isolated from the aerial parts of Premna fulva. Structures of 1-4 were established by a combination of extensive spectroscopic analyses, quantum chemical calculations, and X-ray crystallography. Plausible biosynthetic pathways of 1-4 were proposed. Interestingly, 2 and 3 exhibited opposite effects on estrogen biosynthesis in human ovarian granulosa-like KGN cells by modulating the expression of aromatase.
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http://dx.doi.org/10.1021/acs.orglett.8b02845DOI Listing
October 2018

In Vitro Human Dihydroorotate Dehydrogenase Inhibitory, Anti-inflammatory and Cytotoxic Activities of Alkaloids from the Seeds of Nigella glandulifera.

Planta Med 2018 Sep 5;84(14):1013-1021. Epub 2018 Apr 5.

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China.

Four new dolabellane-type diterpene alkaloids, glandulamines A - D (1:  - 4: ), together with twelve known compounds (5:  - 16: ), were isolated from the seeds of using repeated column chromatography and semipreparative HPLC. The structures of 1:  - 16: were elucidated based on NMR data analysis, HRMS experiments and other spectroscopic interpretations. The absolute configuration of 5: was determined by single-crystal X-ray diffraction data for the first time. Compounds 10: and 12: showed human dihydroorotate dehydrogenase inhibitory activity with IC values of 61.1 ± 5.3 and 45.9 ± 3.0 µM, respectively. Molecular docking of the active compound 12: and positive control teriflunomide on the inhibitor-binding site of human dihydroorotate dehydrogenase was subsequently performed to visualize the interaction pattern. In addition, compounds 8: and 10: exhibited inhibitory effects against lipopolysaccharide-induced nitric oxide production with inhibition rates of 61 and 41%, respectively, at the concentration of 10 µM. Compounds 9: and 12: showed cytotoxic activities with cell viability varying from 29 ~ 57% at 100 µM against T98G, U87, U251, and GL261 glioma cancer cell lines. These data provide new insights on the pharmacologically active compounds of this plant widely used in folk medicine.
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http://dx.doi.org/10.1055/a-0598-4866DOI Listing
September 2018

Isolation, Characterization, and Structure-Activity Relationship Analysis of Abietane Diterpenoids from Callicarpa bodinieri as Spleen Tyrosine Kinase Inhibitors.

J Nat Prod 2018 04 26;81(4):998-1006. Epub 2018 Mar 26.

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology , Yunnan University , Kunming , Yunnan 650091 , People's Republic of China.

Species belonging to the genus Callicarpa are used traditionally in Chinese medicine for the treatment of inflammation, rheumatism, and pain. Investigation of the leaves and twigs of Callicarpa bodinieri resulted in the isolation of nine new abietane diterpenoids, bodinieric acids A-I (1-9), along with six known compounds (10-15). The structures of 1-9 were elucidated on the basis of the interpretation of their HRESIMS and NMR data and by ECD calculations. To explore the potential therapeutic target of this plant for immune-mediated disease, the inhibitory activities of the isolates obtained were determined against 13 kinase enzymes. Eight compounds exhibited moderate inhibitory effects on spleen tyrosine kinase (SYK), and the IC values of compounds 2 and 6 were 7.2 and 10.7 μM, respectively. In addition, a preliminary structure-activity relationship of this scaffold was analyzed with both molecular docking and a 3D-QSAR pharmacophore model.
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http://dx.doi.org/10.1021/acs.jnatprod.7b01082DOI Listing
April 2018

Phytochemistry and pharmacology of the genus Leonurus: The herb to benefit the mothers and more.

Phytochemistry 2018 Mar 12;147:167-183. Epub 2018 Jan 12.

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan University, Kunming 650091, PR China. Electronic address:

Plants belonging to the genus Leonurus, also named motherwort, are traditionally used for anti-gynecological disorder in East Asia, and for sedative in Europe. Chemical investigation of the genus Leonurus not only enriched the natural products library, but also enlarged the pharmacological application of this traditional herb. In this review, we systematically summarized the structures of 259 compounds isolated from the genus Leonurus, featured with 147 labdane diterpenoids. The reported bioactivity studies up to 2017 are presented in the second part, with the main focus on the isolated compounds and also concerning the extracts. In addition to the traditional uterine contraction and sedative activity, recently the cardiovascular protection effect of leonurine has drawn most attention. Other than that, neuroprotection, anti-inflammation, anti-cancer, anti-platelet aggregation and many other activities have been assigned to various compounds from the genus Leonurus. Among 70 bioactivity references cited in this review, 57% of them were concentrated on two alkaloids (leonurine and stachydrine), whereas only 20% are about the 147 diterpenoids. Anti-inflammation is the major bioactivity discovered so far for the labdane diterpenoids from the genus Leonurus, whose further therapeutic potential still remains for exploration.
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http://dx.doi.org/10.1016/j.phytochem.2017.12.016DOI Listing
March 2018

Hispanane-Type Diterpenoid and Secoiridoid Glucosides from Viburnum cylindricum.

Chem Biodivers 2018 Jan 5;15(1). Epub 2018 Jan 5.

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, P. R. China.

Three hitherto unknown compounds, including one new hispanane-type diterpenoid glucoside, namely viburnumoside (1), two new secoiridoid glucosides, 7α-galloyloxysweroside (2), and 7β-galloyloxysweroside (3), together with ten known compounds (4 - 13) were isolated from the ethanol extract of twigs and leaves of Viburnum cylindricum. Their structures were elucidated on the basis of extensive spectroscopic studies, and the absolute configuration of compound 1 was confirmed by the experimental and calculated electronic circular dichroism (ECD) data.
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http://dx.doi.org/10.1002/cbdv.201700418DOI Listing
January 2018

[Photocatalytic Degradation of Perfluorooctanoic Acid by Pd-TiO2 Photocatalyst].

Huan Jing Ke Xue 2015 Jun;36(6):2138-46

Perfluorooctanoic acid (PFOA) is a new persistent organic pollutant which has got global concern for its wide distribution, high bioaccumulation and strong biological toxicity. In present study, the photocatalytic degradation of PFOA using palladium doped TiO2 (Pd-TiO2) prepared by chemical reduction method was investigated. The photocatalysts were characterized by XRD, FESEM and UV-vis DRS and were used for PFOA degradation under 365 nm UV irradiation. The results indicated that the grain size of TiO2 was smaller while the specific surface area increased and the absorption of ultraviolet light also enhanced after using chemical reduction method, but all these changes had no influence on PFOA degradation. However, the degradation was significantly enhanced because of the deposition of Pd, the fluoride concentration of PFOA was 6.62 mg x L(-1) after 7 h irradiation which was 7.3 times higher than that of TiO2 (P25). Experiments with the addition of trapping agent and nitrogen indicated that *OH played an important role in PFOA degradation while the presence of O2 accelerated the degradation. The main intermediate products of photocatalytic degradation of PFOA were authenticated by an ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry systems (UPLC-QTOF-MS). The probable photocatalytic degradation mechanism involves h+ attacking the carboxyl of PFOA and resulting in decarboxylation. The produced *CnF(2n +1) was oxidized by *OH underwent defluorinetion to form shorter-chain perfluorinated carboxylic acids. The significant enhancement of PFOA degradation can be ascribed to the palladium deposits, acting as electron traps on the Pd-TiO2 surface, which facilitated the transfer of photogenerated electrons and retarded the accumulation of electrons.
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