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Oxidative Oligomerization Ntawm DBL Catechol, Muaj Peev Xwm Cytotoxic Compound rau Melanocytes, Qhia Txog Qhov tshwm sim ntawm Novel Ionic Diels-Alder Hom Ntxiv Ntu 2

May 18, 2023

Tseem muaj cov tebchaw tsim los ntawm lub dimer nrog kev poob ntawm ob protons. Cov tebchaw eluted ntawm 17 min, 18 min, 20 min, thiab 21 min nrog molecular mass ntawm 353.1021, uas yog nyob rau hauv 1.5 ppm ntawm theoretical mass rau C20H16O6 (353.1013 amu). CID spectrum ntawm cov tebchaw no sib txawv heev, qhia tias muaj ntau yam isomers raug tsim nyob rau hauv cov tshuaj tiv thaiv sib tov (Figures 8-11).

Raws li cov kev tshawb fawb cuam tshuam, cistanche yog ib hom tshuaj ntsuab uas hu ua "cov tshuaj ntsuab muaj txuj ci uas ua rau lub neej ntev". Nws lub ntsiab tivthaiv yog cistanoside, uas muaj ntau yam teebmeem xws li antioxidant, tiv thaiv kev mob, thiab kev tiv thaiv kev ua haujlwm. Cov txheej txheem ntawm cistanche thiab tawv nqaij dawb yog nyob rau hauv cov nyhuv antioxidant ntawm cistanche glycosides. Melanin nyob rau hauv tib neeg daim tawv nqaij yog tsim los ntawm oxidation ntawm tyrosine catalyzed los ntawm tyrosinase, thiab cov tshuaj tiv thaiv oxidation yuav tsum muaj kev koom tes ntawm oxygen, yog li cov pa-dawb radicals nyob rau hauv lub cev ua ib qho tseem ceeb cuam tshuam rau melanin ntau lawm. Cistanche muaj cistanoside, uas yog ib qho antioxidant thiab tuaj yeem txo qhov tsim ntawm cov dawb radicals hauv lub cev, yog li inhibiting melanin ntau lawm.

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Nyem rau ntawm Cistanche Tubulosa rau Whitening

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Lub ncov eluting ntawm 20 min pom tsuas yog dej poob raws li cov khoom loj (m / z 335 ion hauv daim duab 10). Lub ncov eluting ntawm 21 min tau pom lub ncov loj nrog kev poob ntawm COCH2 pawg (m / z 311 ions). Qhov sib xyaw no yuav tsum yog daim ntawv oxidized ntawm DBL quinone dimer. Ntawm qhov tod tes, lub ncov eluting ntawm 18 min pom qhov loj decomposition ions ntawm 335 (dej tsis), 311 (COCH2 poob), thiab me me ion ntawm m / z 293 (dej thiab COCH2 poob). Nco ntsoov tias qhov kawg decomposition ion tsis tuaj yeem ua rau DBL quinone dimer thiab tsuas yog ua tau rau daim ntawv oxidized ntawm benzodioxan dimer. Los ntawm cov txiaj ntsig no nws tau txiav txim siab tias ob yam sib txawv ntawm cov dimers tau tsim nyob rau hauv cov tshuaj tiv thaiv - ib qho benzodioxan dimer thiab DBL quinone dimer.

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Cov oxidized dimers yuav pom pom pom, zoo li lwm yam yooj yim unconjugated quinones. Qhov no yog raws li qhov siab tshaj plaws absorbance ntawm 420 nm, uas yog vim lub quinonoid compound accumulating nyob rau hauv DBL catechol-tyrosinase cov tshuaj tiv thaiv sib tov. Lub DBL quinone dimer tuaj yeem aromatize thiab ntxiv oxidize rau quinone methide. Thaum lub benzodioxan dimer yuav raug oxidation rau quinone uas yuav ces isomerize rau sab saw desaturated compound. Yog li, thawj zaug dimers nrog m / z 355 hloov mus rau oxidized daim ntawv ntawm cov dimers nrog m / z 353.

Ntxiv nrog rau cov khoom siv dimeric, cov khoom sib xyaw trimeric kuj tseem tuaj yeem pom nyob rau hauv qhov loj spectrum ntawm cov tshuaj tiv thaiv sib tov. Ib zaug ntxiv, ob niam txiv ions ntawm m / z 529.1486 yog tam sim no, ib qho eluting ntawm 20 min thiab lwm qhov ntawm 22 min (Daim duab 5 vaj huam sib luag C). Lawv loj yog nyob rau hauv 3 ppm ntawm qhov loj ntawm theoretical protonated trimeric compound (C30H26O9). Lawv CID spectra yog qhia nyob rau hauv daim duab 12 thiab 13. CID ntawm ib isomer muab ib tug loj ion ntawm 351, sib xws rau lub dimer lub siab oxidized daim ntawv. Lwm tus isomer muab ntau npaum li cas ntawm cov khoom no. Nws tsis tuaj yeem paub qhov txawv ntawm cov qauv ntawm cov trimers raws li tus qauv fragmentation. Txawm li cas los xij, nws tau pom tseeb tias cov khoom sib txawv trimeric kuj tsim nyob rau hauv cov tshuaj tiv thaiv sib tov. Yog li, cov txiaj ntsig tau nthuav tawm hauv daim ntawv no tau lees paub tias DBL catechol yog qhov cuam tshuam tsis zoo rau oxidative polymerization raws li tau hais hauv kev ua haujlwm dhau los ntawm ib qho ntawm peb pawg [11].

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Kev tsim ntawm dimers thiab trimers tuaj yeem piav qhia los ntawm cov reactivities ntawm quinonoid cov khoom tsim nyob rau hauv cov tshuaj tiv thaiv (Daim duab 14). Oxidation ntawm DBL catechol ua rau nws sib xws quinone, uas yog hydrophobic heev thiab tuaj yeem yooj yim nthuav tawm cov tshuaj tiv thaiv cycloaddition nrog niam txiv catechol. Lub ionic Diels-Alder ntxiv ntawm DBL quinone rau niam txiv catechol yuav tsim ob hom adducts raws li qhia hauv daim duab 14. Cov tshuaj tiv thaiv ntawm quinonoid carbonyl pawg nrog cov desaturated sab saw yuav tsim cov benzodioxan dimer. Nyob rau hauv sib piv, dienone sab saw ntxiv nrog rau desaturated sab saw tsim cov pyran-hom adduct tsuas yog xaiv raws li DBL quinone dimer. Ob lub tebchaw no tuaj yeem nkag mus rau oxidation yooj yim thiab cov tshuaj tiv thaiv ntxiv los tsim cov tshuaj trimeric los ntawm cov tshuaj Diels-Alder zoo sib xws. Txawm hais tias qhov tshwm sim lom ntawm Diels-Alder cov tshuaj tiv thaiv yog qhov tsawg heev, nws tau raug tshaj tawm mus rau ob peb qhov xwm txheej [20–23]. Piv txwv li, ib qho ntawm peb cov pab pawg tsis ntev los no tau qhia tias quinone ntawm N-acetyl dopa methyl ester tab tom ua rau cycloaddition sai, tej zaum ntawm ionic Diels-Alder cov tshuaj tiv thaiv, tsim ib qho zoo sib xws benzodioxan dimer [20]. Cov kev tshawb fawb tam sim no kuj tseem txhawb nqa qhov tshwm sim ntawm xws li ionic Diels-Alder ntxiv hauv quinonoid chemistry ntawm sab-chain desaturated catechols. Cov tshuaj tiv thaiv cyclization no yog tag nrho cov nonenzymatic thiab li no yuav tsis yog-stereoselective, ua rau kev tsim khoom ntawm ntau cov khoom isomeric. Kev tsim khoom ntawm ntau yam khoom no thaum lub sij hawm nonenzymatic cyclization ntawm enzymatically generated quinonoid hom tau raug sau tseg zoo nyob rau hauv qhov chaw kuaj no rau ntau dehydrodopa thiab dehydrodopamine derivatives [16-20].

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Lub potentmelanotoxicity ntawm RK thiab nws cov khoom txo qis, rhododendron, yog tam sim no tsim tau zoo [1–8,24]. Txawm hais tias qee qhov kev cuam tshuam xws li depletion ntawm thiols thiab ntxiv rau cellular nucleophiles kuj tseem muaj rau lwm cov cytotoxic quinones, qhov tshwj xeeb genotoxicity ntawm RK thiab rhododendron tuaj yeem raug sau tseg rau lawv lub peev xwm los nthuav tawm ntau cov tshuaj tiv thaiv redox uas tsim tsis tau tsuas yog lawv cov quinonoid derivatives sib xws. tab sis kuj muaj ob peb sab saw desaturated quinonoid hom. Tsis tas li ntawd, ntau ntau ntawm dimeric thiab trimeric compounds raug tsim, tag nrho cov muaj peev xwm ua rau reactive oxygen hom ntau lawm, depletion ntawm cellular thiols, thiab cov tshuaj tiv thaiv nrog cellular macromolecules nrog rau cov proteins thiab DNA [11,24]. Cov tshuaj uas muaj ntau yam tshuaj tiv thaiv redox yog li ntawd yuav muaj tshuaj lom ntau dua li cov tshuaj quinonoid yooj yim. Nws yog qhov nyuaj rau txheeb xyuas ib lossis lwm yam khoom ntawm RK lossis rhododendron ua tus neeg sawv cev ua rau ua rau leukoderma thiab lwm yam teebmeem myelotoxic. Nrog rau cov txiaj ntsig no hauv siab, peb ceeb toom tawm tsam kev siv cov tshuaj sib xyaw no thiab lwm yam catechols uas muaj lub zog los nthuav tawm ntau cov tshuaj tiv thaiv redox rau kev kho mob ntawm cov teeb meem melanin.

3. Cov ntaub ntawv thiab cov txheej txheem

Khoom siv: DBL catechol tau txais los ntawm Fujifilm-Wako Pure Chemicals (Osaka, Nyiv). Mushroom tyrosinase (cov haujlwm tshwj xeeb 5771 units / mg ntawm cov protein) tau yuav los ntawm Sigma Chemical Co., St. Louis, MO. HPLC qib methanol thiab ammonium formate (99 feem pua) tau txais los ntawm Acros, Morris Plains NJ. Milli Q synthesis A10 Dej purification system yuav los ntawm Millipore, Milford, MA tau siv los npaj HPLC qib dej. Mobile theem kuab tshuaj (formic acid, acetonitrile) rau huab hwm coj spectrometry tau muas los ntawm Fisher Chemical (Fair Lawn, NJ, USA) thiab yog Optima LC/MS Qib. Tag nrho lwm cov tshuaj yog ntawm qib analytical thiab yuav los ntawm Fisher thiab/los yog VWR.

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Enzyme assays: Ib qho tshuaj tiv thaiv sib xyaw (1 mL) uas muaj DBL catechol (feem ntau yog 0.2 mM), txog 5-10 µg ntawm nceb tyrosinase hauv 50 mM sodium phosphate tsis nyob ntawm pH teev nyob rau hauv chav tsev kub thiab spectral. Cov kev hloov pauv cuam tshuam nrog oxidation tau ua raws li siv lub diode array spectrophotometer. Qee cov tshuaj tiv thaiv tau ua nyob rau hauv acidic mob. Tshuaj oxidation ntawm DBL catechol nrog sodium periodate tau ua nyob rau hauv ib tug mole-to-mole piv ntawm pH qhov tseem ceeb. Cov xwm txheej raug muab nyob rau hauv txhua daim duab dab neeg.
Kev npaj ua piv txwv rau cov kev tshawb fawb loj spectral: Cov tshuaj tiv thaiv sib xyaw uas muaj 100 nmol ntawm DBL catechol thiab 5 µg ntawm tyrosinase yog incubated hauv 1 mL dej ntawm chav tsev kub rau ob feeb thiab ib qho aliquot ntawm cov tshuaj tiv thaiv. (100 mL) tau quenched nrog (900 mL) 1 feem pua ​​trifluoroacetic acid. Qhov sib tov diluted no tau raug soj ntsuam loj spectrometric. Cov tshuaj tiv thaiv diluted raug txhaj ncaj qha rau hauv qhov loj spectrometer. RP-nLC/ESI-MS cov xwm txheej: Ib qho Orbitrap Fusion Lumos huab hwm coj spectrometer (Thermo Fisher, San Jose, CA, USA) ua ke hauv online rau EASY-nLC 1200 (Thermo Fisher, San Jose, CA, USA) tau siv los kuaj thiab characterize cov khoom. Lub nLC system tau ua haujlwm ntawm tus khub tus nqi ntawm 300 nL / min siv cov kab ncaj nraim ntawm 0-70 feem pua ​​B hauv 15 min. Txawb theem A yog 96.1: 3.9 0.1 feem pua ​​formic acid hauv dej / 0.1 feem pua ​​formic acid hauv acetonitrile. Mobile theem B yog 80.0:20.0 0.1 feem pua ​​formic acid hauv dej / 0.1 feem pua ​​formic acid hauv acetonitrile. Cov qauv yog thawj zaug desalted ntawm Thermo Fisher Scientific Acclaim PepMap 100 C18 HPLC kem (3 µm particle loj, 75 µm × 2 cm, 100 Å) ua ntej sib cais ntawm Thermo Fisher Scientific PepMap RSLC C18 EASY-Spray Column , 75 µm × 15 cm, 100 Å).
Lub Orbitrap Fusion Lumos huab hwm coj spectrometer tau ua haujlwm hauv hom me me. Kev teeb tsa thoob ntiaj teb tau raws li hauv qab no: ion qhov chaw hom NSI, qhov zoo voltage ntawm 1900 V, thiab Ion Hloov Tube Temp ntawm 275 ◦C. Ions rau MS scans tau kuaj pom hauv Orbitrap nrog kev daws teeb meem ntawm 30,000. Qhov ntau npaum li cas yog qhov qub, thiab qhov ntsuas ntsuas tau teem rau 100–1000 m/z. Lub lens RF tau teem rau 30 feem pua ​​​​thiab AGC lub hom phiaj thiab lub sijhawm txhaj tshuaj siab tshaj plaws yog 4.0 × 105 thiab 50 ms, feem. Cov ntaub ntawv-dependent MS2 CID scans tau khiav ua ke nrog lub hom phiaj huab cua lim nyob rau hauv uas cov phiaj xwm pawg sib raug rau cov kab mob hauv qab no: DBL (179.0708 m / z), DBL-quinone (177.0551 m / z), DBL-quinone dimer (355.1182 m/z), DBL-quinone trimer (529.1499 m/z), DBL-dej adduct (197.0813 m/z), thiab DBL-dimer nrog poob ntawm 2H (353.1026 m/z). Ib qho kev siv zog ntawm 2.0 × 103 tau teeb tsa rau txhua qhov loj nrog qhov ua siab ntev ntawm ± 10 ppm. Ions rau ddMS2 CID raug cais nyob rau hauv lub ion ntxiab nrog ib tug ceev scan npaum li cas thiab nrog ib tug cais qhov rais ntawm 2 m / z. Ions tau tawg ntawm CID nrog lub zog sib tsoo ruaj khov ntawm 40 feem pua. Q parameter rau CID ua kom raug teeb tsa rau 0.25. Lub hom phiaj AGC thiab lub sijhawm txhaj tshuaj siab tshaj plaws tau teem rau 1.0 × 104 thiab 500 ms. Lub sijhawm voj voog rau cov ntaub ntawv-nyob ntawm qhov tau txais tau teem rau 3 s.
Tus sau kev koom tes:Conceptualization, MS, SI, thiab KW; methodology, MS, JE, RM, thiab KU; kev soj ntsuam, MS thiab JE; kev tshawb nrhiav, MS, JE, RM, thiab KU; Resources, MS, SI, and KW; data curation, MS, JE, RM, thiab KU; kev sau ntawv-kev npaj ua ntej, MS; sau ntawv— tshuaj xyuas thiab kho, MS, SI, KW, thiab JE; kev pom, MS; kev saib xyuas, MS thiab JE; kev tswj xyuas qhov project, MS Txhua tus kws sau ntawv tau nyeem thiab pom zoo rau cov ntawv luam tawm ntawm cov ntawv sau.
Nyiaj txiag: Qhov kev tshawb fawb no tsis tau txais nyiaj txiag sab nraud.
Kev tsis sib haum xeeb ntawm kev txaus siab:Cov kws sau ntawv tshaj tawm tsis muaj kev sib cav txog kev txaus siab.

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Cov ntawv luv

CID Collision induced decomposition
DBL 3, 4-dihydroxybenzalacetone
LC/MS High-pressure kua chromatography/mass spectrometry
RK Raspberry ketone

Cov ntaub ntawv

1. Beekwilder, J.; van der Meer, kuv.; Sibbesen, O.; Broekgaarden, M.; qws, i.; Mikkelsen, JD; Hall, RD Microbial ntau lawm ntawm ntuj raspberry ketone. Biotechnol. J. 2007, 2, 1270–1279. [CrossRef] [PubMed]

2. Fukuda, Y.; Nagano, M.; Futatsuka, M. Kev ua haujlwm leukoderma hauv cov neeg ua haujlwm koom nrog 4-(p-hydroxy phenyl)-2-butanone manufacturing. J. Nyob. Health 1998, 40, 118–122. [CrossRef]

3. Nishigori, C.; Aoyama, Y.; Ib, A.; Suzuki, K.; Suzuki, T.; Tanemura, A.; Ib, M.; Katayama, ib.; Oiso, N.; Kagohashi, Y.; ua al. Qhia rau cov kws kho mob (piv txwv li, kws kho mob dermatologist) rau kev tswj hwm ntawm Rhododenol-induced leukoderma. J. Dermatol. 2015, 42, 113–128. [CrossRef] [PubMed]

4. Sasaki, M.; Konda, M.; Saib, K.; Umeda, M.; Kev, K.; Takahashi, Y.; Suzuki, T.; Matsunaga, K.; Inoue, S. Rhododendron, depigmentation-inducing phenolic compound, exerts melanocyte cytotoxicity ntawm tyrosinase nyob ntawm mechanism. Pigment Cell Melanoma Res. Xyoo 2014, 27, 754–763. [CrossRef] [PubMed]

5. Kasamatsu, S.; Hachiya, A.; Nakamura, S.; Nakamura, S.; Yasuda, Y.; Fujimori, T.; Takano, K.; Moriwaki, S.; Hais, T.; Suzuki, T.; ua al. Depigmentation tshwm sim los ntawm daim ntawv thov ntawm cov khoom siv ci ntsa iab, rhododendron, muaj feem xyuam rau kev ua tyrosinase ntawm ib qho chaw pib. J. Dermatol. Sci. 2014, 76, 16–24. [CrossRef] [PubMed]

6. Ib., S.; Yamashita, T.; Ojika, M.; Wakamatsu, K. Tyrosinase-catalyzed oxidation ntawm rhododendron tsim 2-methyl-chromane-6,7-dione, lub putative kawg tshuaj lom metabolite: cuam tshuam rau melanocyte toxicity. Pigment Cell Melanoma Res. Xyoo 2014, 27, 744–753. [CrossRef] [PubMed]

7. Ib., S.; Gerwat, W.; Kob, L.; Yamashita, T.; Ojika, M.; Wakamatsu, K. Tib neeg tyrosinase tuaj yeem oxidize ob qho tib si enantiomers ntawm rhododendron. Pigment Cell Melanoma Res. 2014, 27, 1149–1153. [CrossRef]

8. Ib., S.; Okura, M.; Wakamatsu, K.; Yamashita, T. Lub zog pro-oxidant kev ua ntawm rhododendrol-eumelanin induces cysteine ​​depletion nyob rau hauv B16 melanoma hlwb. Pigment Cell Melanoma Res. 2017, 30, 63–67. [CrossRef]

9. Ib., S.; Okura, M.; Nakanishi, Y.; Ojika, M.; Wakamatsu, K.; Yamashita, T. Tyrosinase-catalyzed metabolism ntawm rhododendron (RD) hauv B16 melanoma hlwb: Kev tsim cov RD-pheomelanin thiab covalent khi nrog thiol proteins. Pigment Cell Melanoma Res. 2015, 28, 295–306. [CrossRef]

10. Ib., S.; Wakamatsu, K. Biochemical mechanism ntawm rhododendron-induced leukoderma. Int. J. Mol. Sci. 2018, 19, 552. [CrossRef]

11. Ib., S.; Hinoshita, M. Suzuki, E.; Ojika, M.; Wakamatsu, K. Tyrosinase-catalyzed oxidation ntawm leukoderma-inducing tus neeg sawv cev raspberry ketone tsim (E)-4-(3-oxo-1-butenyl)-1, 2- benzoquinone: Kev cuam tshuam rau melanocyte toxicity. Chem. Res. Toxicol. Xyoo 2017, 30, 859–{11}}. [CrossRef]

12. Sugumaran, M.; Dali, H.; Kundzicz, H.; Semensi, V. Qhov txawv txav intramolecular cyclization thiab sab saw desaturation ntawm carboxyethyl-o-benzoquinone derivatives. Bioorg. Chem. Xyoo 1989, 17, 443–453. [CrossRef]

13. Sugumaran, M.; Ricketts, D. Qauv sclerotization kev tshawb fawb. 3. Cuticular enzyme-catalyzed oxidation ntawm peptidyl qauv tyrosine thiab dopa derivatives. Arch. Kab Biochem. Physiol. Xyoo 1995, 28, 17–32. [CrossRef]

14. Sugumaran, M. Reactivities ntawm quinone methides piv rau o-quinones hauv catecholamine metabolism thiab eumelanin biosynthesis. Int. J. Mol. Sci. 2016, 17, 1576. [CrossRef]

15. Ib., S.; Sugumaran, M.; Wakamatsu, K. Tshuaj reactivities ntawm ortho-quinones tsim nyob rau hauv cov kab mob nyob: Txoj hmoo ntawm quinonoid cov khoom tsim los ntawm tyrosinase thiab phenoloxidase kev txiav txim ntawm phenols thiab catechols. Int. J. Mol. Sci. 2020, 21, 6080. [CrossRef]

16. Abele, A.; Zheng, D.; Evans, J.; Sugumaran, M. Reexamination ntawm lub mechanisms ntawm oxidative transformation ntawm kab cuticular sclerotizing precursor, 1, 2-dehydro-N-acetyldopamine. Kab Biochem. Mol. Biol. 2010, 40, 650–659.

17. Abeb, A.; Kuang, QF; Evans, J.; Robinson, NWS; Sugumaran, M. Oxidative transformation ntawm trichrome qauv compound muab kev pom tshiab rau hauv crosslinking thiab tiv thaiv cov tshuaj tiv thaiv ntawm tunichromes. Bioorg. Chem. 2017, 71, 219–229. [CrossRef]

18. Kuang, QF; Ab, A.; Evans, J.; Sugumaran, M. Oxidative transformation of tunichromes—Model study with 1,2-dehydro-N-acetyldopamine and N-acetylcysteine. Bioorg. Chem. Xyoo 2017, 73, 53–62. [CrossRef]

19. Abeb, A.; Kuang, QF; Evans, J.; Sugumaran, M. Mass spectrometric kev tshawb fawb pom qhov txawv txav ntawm oxidative transformation ntawm 1,2-dehydro-N-acetyldopa. Rapid Comm. Pawg Spectrom. Xyoo 2013, 27, 1785–1793. [CrossRef]

20. Abeb, A.; Zheng, D.; Evans, J.; Sugumaran, M. Novel post-translational oligomerization ntawm peptidyl dehydrodopa qauv compound, 1, 2-dehydro-N-acetyldopa methyl ester. Bioorg. Chem. 2016, 66, 33–40. [CrossRef]

21. Takao, KI; Munakata, R.; Tadano, KI Tsis ntev los no tau nce qib hauv cov khoom siv ntuj tsim los ntawm kev siv cov tshuaj intramolecular Diels-Alder. Chem. Rev. 2005, 105, 4779–4807. [CrossRef] [PubMed]

22. Ose, T.; Watanabe, K.; Mie, T.; Hmo, M.; Watanabe, H.; Yaj, M.; Oikawa, H.; Tanaka, I. Kev nkag siab rau lub ntuj Diels-Alder cov tshuaj tiv thaiv los ntawm cov qauv ntawm macrophage synthase. Xwm Txheej 2003, 422, 185–189. [CrossRef] [PubMed]

23. Tuav, EM; Williams, RM Chemistry thiab biology ntawm biosynthetic Diels-Alder cov tshuaj tiv thaiv. Angew. Chem. Int. Ed. Engl. 2003, 42, 3078–3115. [CrossRef] [PubMed]

24. Ib., S.; Agata, M.; Okochi, K.; Wakamatsu, K. Lub zog prooxidant kev ua ntawm rhododendrol-eumelanin yog txhim kho los ntawm ultraviolet A hluav taws xob. Pigment Cell Melanoma Res. Xyoo 2018, 31, 523–528. [CrossRef]

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