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PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY · 2019 · IF 2.87

Capsaicinoid metabolism by the generalist Helicoverpa armigera and specialist H. assulta: Species and tissue differences

Jiang Zhu,Kai Tian,Christopher A. Reilly,Xinghui Qiu

Helicoverpa armigera and H. assulta are two of the few insects that can feed on hot pepper fruits. Capsaicin and dihydrocapsaicin ( i.e. , capsaicinoids) are the principal pungent compounds in hot peppers. To explore possible molecular mechanisms of adaptation that allow these two species to consume capsaicinoids, the capacity of the three detoxification tissues (fat body, midgut, and Malpighian tubule) of the two pests, to metabolically degrade capsaicin and dihydrocapsaicin, was compared. The results showed that capsaicin and dihydrocapsaicin were metabolized by crude enzyme preparations from all three tissues of the two pests. Five metabolites of capsaicin, and five metabolites of dihydrocapsaicin were identified. Tissue and species differences in the degree of capsaicin and dihydrocapsaicin metabolism were observed. The specialist H. assulta had an overall greater capacity to degrade the capsaicinoids compared to the generalist H. armigera. Further, the midgut was the most significant contributor to capsaicinoid metabolism. The notably high specific activity in Malpighian tubules of H. armigera also further highlights the significance of this organ in xenobiotic detoxification. Alkyl hydroxylation and dehydrogenation were the main pathways for the oxidative biotransformation of both capsaicin and dihydrocapsaicin by cytochrome P450s. This study provides evidence that enhanced metabolic decomposition of capsaicinoids may be an adaptation explaining dietary preferences for Capsicum fruits by these two pests.

研究领域: 昆虫学 · 植物化学 · 分子生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF INSECT SCIENCE · 2021 ·Vol. 21 ·期 1 · IF 1.857

Evaluation of Sensitivity to Phoxim and Cypermethrin in an Endoparasitoid, Meteorus pulchricornis (Wesmael) (Hymenoptera: Braconidae), and Its Parasitization Efficiency Under Insecticide Stress

Sheng Sheng,Wang Jiao,Zhang Xiao-rui,Liu Zhi-xiang,Yan Meng-wen,Shao Ying,Zhou Jin-cheng,Wu Fu-an,Wang Jun

Insecticides can have consequences for beneficial arthropods. Insect parasitoids can contact insecticides through direct exposure spray droplets or residues on crop foliage. Here, we focus on better understand the response of Meteorus pulchricornis (Wesmael), a parasitoid wasp of lepidopteran pests, and its detoxification mechanisms on stress caused by phoxim and cypermethrin. Hence, we determined the dose–mortality curves and estimating the sublethal concentrations (LC30 and LC50). Then, we applied the sublethal concentrations against adult parasitoids to assess its survival, parasitism efficacy, and also developmental and morphometric parameters of their offspring. Simultaneously, we check the activities of glutathione S-transferase (GST), acetylcholinesterase (AChE), and peroxidase (POD) after sublethal exposure of both insecticides, which has measured until 48 h after treatment. Overall, phoxim and cypermethrin exhibited acute lethal activity toward the parasitoid with LC50 values 4.608 and 8.570 mg/liter, respectively. Also, we detect that LC30 was able to trigger the enzymatic activity of GST, AChE, and POD, suggesting a potential detoxification mechanism. However, even when subjected to sublethal exposure, our results indicate strong negatives effects, in particular for phoxim, which has affected the parasitism efficacy and also the developmental and morphometric parameters of M. pulchricornis offspring. Therefore, it can be concluded that both phoxim and cypermethrin have negative impacts on M. pulchricornis and we suggest cautioning their use and the need for semifield and field assessments to confirm such an impact.

研究领域: 昆虫学 · 生态毒理学
✓ 已验证 DOI PubMed 高影响因子
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PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY · 2019 · IF 2.87

Capsaicin is efficiently transformed by multiple cytochrome P450s from Capsicum fruit-feeding Helicoverpa armigera

Kai Tian,Jiang Zhu,Mei Li,Xinghui Qiu

Capsaicin (8-methyl- N -vanillyl-6-nonenamide) is the most abundant capsaicinoids found in hot peppers ( Capsicum annum and Capsicum frutescens ). It has been well documented that capsaicin plays an important role in the defense against the attack of herbivores or pathogens on Capsicum plants. A few insect herbivores such as Helicoverpa armigera and Helicoverpa assulta have been recorded to be capable of feeding on hot pepper fruits, suggesting that these insects evolve mechanisms against the toxicity of capsaicin. Although cytochrome P450-meidated detoxification is considered to be an important mechanism by which cotton bollworms cope with capsaicin, experimental evidence is lacking. In this study, we compared the capacity of four H. armigera P450s (CYP6B6, CYP9A12, CYP9A14 and CYP9A17) in capsaicin metabolism, and the capsaicin metabolites were screened and tentatively identified by liquid chromatography–tandem mass spectrometry (LC–MS/MS). HPLC analyses showed that depletion rates of capsaicin were 21.9 ± 0.1, 11.9 ± 1.5, 16.3 ± 1.4 and 14.8 ± 0.2 min −1 for CYP6B6, CYP9A12, CYP9A14 and CYP9A17 respectively. The transformation of capsaicin was inhibited by the P450 inhibitor piperonyl butoxide . A total of seven products were detected, and hydroxylation (aromatic and aliphatic) and dehydrogenation were found to be two main pathways in capsaicin metabolism. In addition, capsaicin metabolism was enzyme selective: M1 (ω-hydroxylated N-macrocyclic metabolite) and M3 (ω-hydroxylated metabolite) were uniquely detected in the CYP6B6 catalytic reaction, while M4 (ω-n hydroxylated capsaicin), M5 (diene of capsaicin) and M6 (doubly oxidized metabolite of dehydrogenated capsaicin) were only detectable in CYP9A metabolisms. A capsaicin dimer (5, 5′-dicapsaicin) was found to be the major metabolite of CYP9A reactions, but the minor product produced by CYP6B6. An overall more similar behavior in capsaicin metabolism was observed among CYP9As than between CYP6B6 and CYP9As. Our data demonstrate that CYP6B6 and CYP9As have a potent capability to transform capsaicin, and individual P450 produce unique metabolite profile. These findings help us to understand the molecular basis of capsaicin adaptation in H. armigera .

CAS / MDL: 367-93-1 53-59-8
研究领域: 昆虫学 · 植物化学 · 分子生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF ECONOMIC ENTOMOLOGY · 2014 ·Vol. 107 ·期 3 ·1233-1238 · IF 1.605

Monitoring of Bactrocera dorsalis (Diptera: Tephritidae) Resistance to Cyantraniliprole in the South of China

Zhang Ruimin,He Shiyu,Chen Jiahua

The oriental fruit fly, Bactrocera dorsalis (Hendel), is a globally important economic insect pest that has evolved resistance to various types of insecticides. Cyantraniliprole (DuPont Cyazypyr) is a new anthranilic diamide insecticide registered to control lepidopteran and sucking insects. The susceptibility of field-collected populations of B. dorsalis to cyantraniliprole was assessed via a diet incorporation bioassay in adults. Based on the obtained LC50 values (ranging from 3.29 to 15.83 μg/g), all the testing populations, including ZZ (Fujian province), HH (Yunnan province), JM (Guangdong province), SY (Hainan province), HZ (Zhejiang province), YL (Guangxi province), SH (Shanghai), WH (Hubei province), and CS (Hunan province), were susceptible to cyantraniliprole, with the samples of WH (Hubei province) being the most tolerant (by 4.80-fold). Two (SY, Hainan province; CS, Hunan province) of the nine field-collected populations of B. dorsalis showed a similar susceptibility to cyantraniliprole, while the remaining populations displayed narrow variations in tolerance compared with the laboratory strain. Synergist assays were performed to determine the potential detoxification mechanisms. Piperonyl butoxide showed significant synergism effects in lab, CS, and resistant strain. S,S,S-tributylphorotrithioate and diethyl maleate also showed obvious synergism effects in resistant strain. A 19.44-fold increase in resistance to cyantraniliprole was observed after 14 generations of selection in the laboratory. The present work clarifies the baseline susceptibility and primary mechanisms of B. dorsalis to cyantraniliprole in the south China and established a cyantraniliprole-resistant strain as well. A sound resistance management strategy is also discussed in relation to the risk of susceptibility.

CAS / MDL: 141-05-9 51-03-6
研究领域: 昆虫学 · 害虫管理 · 农业科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Journal of Zhejiang University-SCIENCE B · 2019 · IF 1.879

Scavenging activity and mechanism study of ferulic acid against reactive carbonyl species acrolein

Zhi-hao Tao,Chang Li,Xiao-fei Xu,Yuan-jiang Pan

Acrolein, known as one of the most common reactive carbonyl species, is a toxic small molecule affecting human health in daily life. This study is focused on the scavenging abilities and mechanism of ferulic acid and some other phenolic acids against acrolein. Among the 13 phenolic compounds investigated, ferulic acid was found to have the highest efficiency in scavenging acrolein under physiological conditions. Ferulic acid remained at (3.04±1.89)% and acrolein remained at (29.51±4.44)% after being incubated with each other for 24 h. The molecular mechanism of the detoxifying process was also studied. Detoxifying products, namely 2-methoxy-4-vinylphenol (product 21 ) and 5-(4-hydroxy-3-methoxyphenyl)pent-4-enal (product 22 ), were identified though nuclear magnetic resonance (NMR) and gas chromatography-mass spectrometry (GC-MS), after the scavenging process. Ferulic acid showed significant activity in scavenging acrolein under physiological conditions. This study indicates a new method for inhibiting damage from acrolein.

研究领域: 食品科学 · 生物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Agronomy-Basel · 2024 ·Vol. 14 ·期 3 ·626 · IF 3.3

Cadmium Exposure Impairs Development, Detoxification Mechanisms and Gene Expression of Glyphodes pyloalis Walker (Lepidoptera: Pyralidae)

Shuaiqi Zhao,Wanglong Miao,Sheng Sheng,Xin Pan,Ping Li,Weihong Zhou,Fuan Wu

Cadmium (Cd) is the most serious heavy metal pollutant in the agricultural soil of China and can transfer and accumulate through the food chain and affect the growth, development and physiological processes of phytophagous insect.Glyphodes pyloalisWalker (G. pyloalis) is one of the most important pests of mulberry, and there are few studies on the adverse effects of heavy metals on insects, especially mulberry pests. To understand the toxicology of Cd exposure onG. pyloalis, we investigated the effects of three different concentrations of Cd (0, 3.89 and 51.69 mg/kg, labeled as control check (CK), low dose (LD) and high dose (HD)) on the development and detoxification mechanism ofG. pyloalisand explored the molecular mechanism of Cd onG. pyloalislarvae using RNA-seq technology. Transcriptome analysis showed that compared with the CK, a total of 63 differentially expressed genes (DEGs) were identified in LD exposure, including 24 upregulated and 39 downregulated candidates. In CK versus HD groups, 395 upregulated DEGs and 436 downregulated DEGs were identified and the expression patterns of 12 genes related to detoxification and metabolism were verified using qPCR. These DEGs were relevant to multiple specific peroxisome and drug metabolism-cytochrome P450 pathways. Gene annotation and quantitative real-time PCR revealed that a high concentration of Cd significantly stimulated the expression of metabolic detoxification enzyme genes. The results revealed that Cd exposure changed the pupal weight, adult emergence rate and the activities of AKP, ACP and GST inG. pyloalisand induced notable adverse effects at the molecular level on detoxification and metabolism such as concentration and time differences. In addition, we silencedCYP12A2by RNA interference. Bioassays showed that after silencingCYP12A2, the survival rate ofG. pyloalisunder Cd exposure was lower than that of the control group.

CAS / MDL: 7790-78-5
研究领域: 环境毒理学 · 昆虫学 · 分子生物学
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Journal of Environmental Chemical Engineering · 2020 · IF 4.3

Detoxification of mustard gas, nerve agents and simulants by peroxomolybdate in aqueous H2O2 solution: Reactive oxygen species and mechanisms

Sanping Zhao,Yongbing Zhu,Hailing Xi,Mengwei Han,Daxue Li,Yang Li,Hongjie Zhao

To overcome the insufficient understanding of the detoxification mechanisms of Chemical Warfare Agents (CWAs) and simulants by a molybdate-activated hydrogen peroxide solution (MoO 4 2− -H 2 O 2 ), detoxification performances toward CWAs and simulants were tested. The detoxification efficacy toward mustard gas (HD), nerve agent GD and VX by using MoO 4 2− -H 2 O 2 was higher than that by using H 2 O 2 activated/modified by sodium hydroxide , ammonia, bicarbonate , and borates, but the vesicant mustard sulfone (HDO 2 ) was only formed when using MoO 4 2− -H 2 O 2 to detoxify HD. Although Reactive Oxygen Species (ROS) such as singlet oxygen ( 1 O 2 ), superoxide anion (O 2 − ), H 2 O 2 and peroxide anion (OOH − ) were detected by electron spin resonance (ESR) and chemiluminescence (CL) in the 0.1 M MoO 4 2− -1.0 M H 2 O 2 solution, 95 Mo NMR indicated that Mo(O 2 ) 4 2− was the dominant oxidant for the oxidation of sulfide to sulfoxide and then to sulfone. Oxidation of HD by Mo(O 2 ) 4 2− occurred on the HD-drop/water interface through a direct oxygen transfer mechanism without the participation of H 2 O molecules, and further oxidation of HD to HDO 2 was inevitable in an aqueous MoO 4 2− -H 2 O 2 solution. 18 O tracer experiments confirmed that OOH − -based perhydrolysis dominated the detoxification reaction of nerve agents in an alkaline H 2 O 2 solution. Considering the balance of oxidation/nucleophilic reactivity for a practical decontaminant, pH 10.5–11 range was recommended as the ideal for the MoO 4 2− -H 2 O 2 system to detoxify CWAs.

CAS / MDL: 100-68-5
研究领域: 化学 · 环境科学
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CHEMOSPHERE · 2019 · IF 5.108

Insights into the degradation and detoxication mechanisms of aqueous capecitabine in electrochemical oxidation process

Lei Xu,Shaoyu Tang,Kaixuan Wang,Xiao Ma,Junfeng Niu

Electrocatalytic oxidation and detoxication of capecitabine (CAP) in aqueous solution were investigated with Ti/SnO 2 –Sb/Ce–PbO 2 anode. The relative contributions of generated free radicals showed an increase in the pseudo zero order tare constants in the following order: OH (9.4%) < SO 4 − (24.2%) < O 2 − (53.3%). The operating parameters and solution matrixes, i.e. applied current densities, initial CAP concentrations, initial Cl − and NO 3 − concentrations, influencing the CAP degradation efficiency were evaluated. The kinetic rate constant of 0.1404 min −1 was found within 7 min at current density of 10 mA cm −2 and initial CAP concentration of 20 mg L −1 , while the mineralization efficiency of 59.5%, mineralization current efficiency of 2.06%, detoxication rate to Escherichia coli of 55.5% were achieved at reaction time 90 min. The major degradation pathways of CAP were oxidation, defluorination and bond cleavage, following with the formation of carboxylic acids , NO 3 − , NO 2 − , NH 4 + and F − . Electrochemical oxidation process based on Ti/SnO 2 –Sb/Ce–PbO 2 anode is proved to be effective for elimination, mineralization and detoxication of aqueous CAP.

研究领域: 环境科学 · 药学 · 电化学工程
✓ 已验证 产品关联 DOI PubMed 高影响因子
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ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY · 2024 · IF 6.2

Unveiling the co-expression network and molecular targets behind rotenone resistance in the Bursaphelenchus xylophilus

Buyong Wang,Rongrong Wen,Xuenan Mao,Jie Chen,Xin Hao

Bursaphelenchus xylophilus is a pathogenic nematode responsible for pine wilt disease, which can cause the demise of pine trees and discoloration of trunks. As rotenone is an important botanical pesticide, its impact on B. xylophilus was investigated through RNA-seq to understand the response mechanism of nematode. The bioassay results yielded the 12-h LC 30 (1.35 mg L −1 ) and LC 50 (2.60 mg L −1 ) values for rotenone. Differential gene expression analysis identified 172 and 614 differentially expressed genes (DEGs) in B. xylophilus exposed to two different concentrations of rotenone (1.35 and 2.60 mg L −1 ). To validate these findings, the expression patterns of 10 DEGs were confirmed through RT-qPCR. Additionally, all DEGs were categorized into eight gene expression profiles using STEM. Notably, the gene ontology (GO) processes of "single-organism process," "metabolic process," and "catalytic activity" were prominently enriched in rotenone-treated samples, suggesting a role for metabolic and catalytic pathways in the nematode's response to rotenone stress. KEGG pathways related to "carbon metabolism," "drug metabolism-cytochrome P450," and "metabolism of xenobiotics by cytochrome P450" were similarly enriched, indicating potential mechanisms for detoxification resistance and oxidative stress resistance. The analysis pointed to the pivotal roles of detoxification- and oxidoreduction-related genes, as well as signal transduction-related genes, in enabling B. xylophilus to adapt to rotenone exposure. These insights could markedly enhance our understanding of nematode resistance mechanisms and potentially inform the development of more effective rotenone-based strategies for controlling B. xylophilus .

CAS / MDL: 67-68-5
研究领域: 植物保护 · 分子生物学 · 农药科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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AQUATIC TOXICOLOGY · 2025 · IF 4.3

Pregnane X receptor attenuates gold nanoparticles’ toxicity through accelerating zebrafish embryo hatching

Jia Hu,Jingjing Tian,Pai Liu,Qian Zhang,Ningyao Li,Jian Yin

It is well known that fish embryos are vulnerable to waterborne nanoparticles (NPs), with delayed hatching being the most common and sensitive endpoint. Up-regulation of hatching enzymes has been believed to be an important detoxification mechanism for NPs, but the inner mechanism for such phenomena has been seldom investigated. This study aimed to investigate the role of pregnane X receptor (Pxr) in maintaining the robustness of embryo hatching after treatment with gold nanoparticles (AuNPs, 4 and 82 nm). For this purpose, embryos from mating of 6-month-old wild-type (WT) AB strain zebrafish ( Danio rerio , 3∼4-cm-length) were treated with AuNPs since 4 h post-fertilization (hpf). It was found that both AuNPs significantly inhibited embryo hatching after 52-h treatment, with Au-4 being more toxic at the same mass concentrations. At non-toxic concentrations and median effective concentrations (EC 50 ) of delayed hatching, both AuNPs induced the mRNA expression of HEs and Pxr at 48 hpf, and Au-4 seemed to be more effective. The induction extents of HEs by AuNPs decreased when Pxr was knocked out or inhibited, indicating the role of Pxr in such process. Additionally, knockout/inhibition of Pxr significantly delayed the hatching of embryos at 56 hpf, and activation of Pxr accelerated the process at moderate concentrations. Such phenomena correlated well with the alterations in the mRNA expression and activities of HEs, indicating a fact that AuNPs activated Pxr and up-regulated HEs, which helped the detoxification of AuNPs. RNA-sequencing analysis of WT and pxr -deficient embryos at 24 hpf confirmed the alteration of he1.1&1.2 . In addition, Pxr influenced mRNA encoding muscle development (muscle system process and striated muscle tissue development) and energy metabolism (carbohydrate metabolic process and ATP metabolic process), which were related to the motility of embryos and determined the hatching speed. Such function was confirmed by the reduced locomotor activity of pxr-deficient larvae at 120 hpf. Overall, these results suggested a novel role of Pxr in promoting the hatching of zebrafish embryos, which contributed to the detoxification of AuNPs.

CAS / MDL: 919-30-2 68-12-2
研究领域: 环境科学 · 分子生物学 · 毒理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF ORGANIC CHEMISTRY · 2017 · IF 4.849

Unusual Double Beckmann Fragmentation Reaction under Physiological Conditions

Lin-Na Xie,Chun-Hua Huang,Dan Xu,Feng Li,Jun-Ge Zhu,Chen Shen,Bo Shao,Hui-Ying Gao,Balaraman Kalyanaraman,Ben-Zhan Zhu

Pyridinium aldoximes, which are best-known as therapeutic antidotes for organophosphorus chemical warfare nerve-agents and pesticides, have been found to markedly detoxify polyhalogenated quinones, which are a class of carcinogenic intermediates and recently identified disinfection byproducts in drinking water. However, the exact chemical mechanism underlying this detoxication remains unclear. Here we demonstrate that pralidoxime can remarkably facilitate the dechlorination/hydroxylation of the highly toxic tetrachloro-1,4-benzoquinone in two-consecutive steps to generate the much less toxic 2,5-dichloro-3,6-dihydroxy-1,4-benzoquonine, with rate enhancements of up to 180 000-times. On the contrary, no accelerating effect was noticed with O-methylated pralidoxime. The major reaction product from pralidoxime was identified as its corresponding nitrile (2-cyano-1-methylpyridinium chloride). Along with oxygen-18 isotope-labeling studies, a reaction mechanism was proposed in which nucleophilic substitution coupled with an unprecedented double Beckmann fragmentation reaction was responsible for the dramatic enhancement in the detoxification process. This represents the first report of an unusually mild and facile Beckmann-type fragmentation that can occur under normal physiological conditions in two-consecutive steps. The study may have broad biomedical and environmental significance for future investigations of aldoxime therapeutic agents and carcinogenic polyhalogenated quinones.

研究领域: 环境科学 · 毒理学 · 有机化学
✓ 已验证 DOI PubMed 高影响因子
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BIORESOURCE TECHNOLOGY · 2025 · IF 9

Synergistic division of labor in a bacterial consortium for enhanced phenanthrene mineralization under cadmium stress: mechanisms of degradation-detoxification coordination

Tianzuo Cheng,Pengyu Zhou,Mingle Zhang,Tianyin Huang,Bingdang Wu,Jinlong Zhuang,Bin Wang,Xiaoyi Xu

The remediation of co-contamination by polycyclic aromatic hydrocarbons (PAHs) and heavy metals poses a significant challenge. Although microbial consortia present a promising approach, their synergistic mechanisms under stress conditions are not fully understood. To address this gap, we constructed a functionally specialized bacterial consortium (KZ) by assembling Klebsiella sp. CW-D3T and Arthrobacter sp. SZ-3, which synergistically enhanced phenanthrene (PHE) degradation and mineralization under cadmium stress (25 mg/L Cd 2+ ), outperforming monocultures by 1.2–1.9-fold. Through biomass-normalized enzyme activity assays, we uncovered a structured division of labor: SZ-3 exhibited superior upstream catalytic activity (50 % higher 2H1N conversion), while CW-D3T dominated downstream mineralization (>80 % contribution). Mechanistic investigations via metagenomics revealed that CW-D3T utilized high-expression efflux pumps (ZntA/zinT) and antioxidant genes ( yhcN ) to mitigate cadmium toxicity, whereas SZ-3 employed the frnE -mediated oxidative stress response and limited Cd 2+ uptake via mntH . This study elucidates a synergistic mechanism for concurrent PAH degradation and heavy metal detoxification, offering a novel bioresource for remediating co-contaminated environments.

CAS / MDL: 7790-78-5 673-31-4
✓ 已验证 产品关联 DOI PubMed 高影响因子
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