Ntu 2: Kev Ua Haujlwm Zoo Tshaj Plaws Ntawm Ntuj Phenols txhawm rau txhim kho kev ua haujlwm lom neeg

Yog xav paub ntxiv, hu rautina.xiang@wecistanche.com

3. Diphenols

Ntujdiphenols, suav nrog catechol, resorcinol, thiab hydroquinone derivatives, yog dav nyob rau hauv cov xwm, feem ntau pom muaj nyob rau hauv ntau yam zaub thiab txiv hmab txiv ntoo. Tej yam ntuj tso tebchaw no feem ntau yog peculiar anti-oxidant thiabanti-inflammatorykev ua si. Qee tus ntawm lawv muaj cov tshuaj tiv thaiv kab mob thiab tshuaj tiv thaiv kab mob. Yog li ntawd, ntuj diphenols feem ntau yog siv los ua scaffolds los npaj cov tshuaj lom neeg muaj txiaj ntsig tshiab. Txawm hais tias muaj qhov dav dav ntawm bioactive diphenols nyob rau hauv qhov, nyob rau hauv no re-

saib, kev saib xyuas yog mob siab rau kev ua kom haum rau kev ua haujlwm ntawm resveratrol, hispolon, thiab hydroxytyrosol, uas tsim muaj ntau thiab muaj zog phenolic tebchaw.

Nyem qhov no kom paub ntau ntxiv txog cov khoom

3.1. Resveratrol Cov

Resveratrol (5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol) yog ib qho phenolic stilbene, feem ntau pom muaj nyob rau hauv ntau yam nroj tsuag thiab txiv hmab txiv ntoo xws li txiv apples, berries, pomegranates, pistachios, raws li zoo raws li nyob rau hauv cov noob thiab daim tawv nqaij ntawm grapes. Yog li, liab cawu cub yog ib qhov chaw siab tshaj ntawm resveratrol [214]. Ob peb txoj kev tshawb fawb tam sim no txuas ntxiv ntawm resveratrol thiab nws cov tshuaj tua kab mob [215],tshuaj tiv thaiv kab mob[216], thiab antitumoral [217-219] kev ua ub no. Ntxiv mus, nws cov ntawv thov hauv kev kho mob ntshav qab zib nephropathy [220] thiab cov kab mob ntawm daim tawv nqaij [221] tau raug tshuaj xyuas. Cov txiaj ntsig cuam tshuam nrog resveratrol, nrog rau qee qhov tsis zoo, feem ntau cuam tshuam nrog nws cov peev xwm cytotoxicity, tau qhia tsis ntev los no [222]. Ntxiv mus, resveratrol cov metabolism sai ua rau tsis muaj bioavailability ntawm cov khoom xyaw nquag. Cov teeb meem zoo li no, ua ke nrog cov dej solubility tsawg, yog ib qho kev txwv tseem ceeb uas yuav tsum tau xav txog. Yog li ntawd, txhawm rau txhim kho bioavailability, ntau lub tshuab xa khoom resveratrol tau raug npaj, txhawm rau txhawm rau txuas ntxiv cov peev txheej biomedical ntawm xws li cov khoom lag luam nthuav dav [223].

Vim muaj kev saib xyuas tseem ceeb ntawm qhov sib xyaw ua ke no, ntau cov ntaub ntawv ntawm nws cov kev ua haujlwm tau raug luam tawm tsis ntev los no; Tsis tas li ntawd, kev tshuaj xyuas sib txawv ntawm cov tshuaj thiab kev ua haujlwm lom neeg ntawm resveratrol analogs thiab qhov teeb meem tshwj xeeb ntawm nws txoj kev ua haujlwm tau luam tawm xyoo 2017 [224].

Tsuas yog hais txog qee qhov piv txwv (Daim duab 5), ntuj thiab hluavtaws resveratrol derivatives thiab oligomers yog cov tshuaj tua kab mob zoo [225] thiab tshuaj tua kab mob [226]; di-, tetra-, thiab hexahydroxy derivatives, nrog rau di-, tri-, tetra-, thiab Penta methoxy analogs nthuav tawm ntau dua bioavailability thiab lom lom zem ua si nrog rau resveratrol[219, 225-227]; Kev hloov pauv ntawm resveratrol nrog carboxy ester, acetal, sulfonate, phosphate, carbonate, carbamate thiab alkyl pawg tau tso cai rau kev hloov pauv ntawm resveratrol dej solubility, bioavailability, nqus los ntawm lub plab zom mov thiab cov khoom lom neeg [228-230]. Kev hloov pauv ntawm Resveratrol ntawm lub nplhaib uas muaj ntxhiab kuj tau tshawb xyuas, ua rau lipophilic derivatives, nrog rau kev tiv thaiv oxidant thiab neuroprotective ua haujlwm [229]. Txhawm rau txhim kho resveratrol anticancer kev ua haujlwm, methoxy, hydroxyl derivatives, nrog rau lwm cov pab pawg ua haujlwm lossis heterocyclic esterification tau raug tshuaj xyuas [231,232].

3.2. Hspolon

Nws polon (6-(3,4-dihydroxyphenyl)-4-hydroxyhexa-3,5-diene-2-ib qho) yog ib qho phenolic compound, muab rho tawm los ntawm cov tshuaj ntsuab nceb Phellinus linteus. Nws yog characterized los ntawm peculiarantioxidantkev ua haujlwm nrog rau cov khoom siv tshuaj tseem ceeb, ua ib qho kev cog lus tiv thaiv kab mob, tshuaj tiv thaiv kab mob, tshuaj tua kab mob, thiab tshuaj tiv thaiv kab mob [233-235]. Tsis ntev los no, ob peb hispolon derivatives tau raug xa mus rau hauv silico kev kwv yees los ntsuas ua ntej lawv cov kev tiv thaiv kab mob. Cov kev tshawb fawb theoretical tau lees paub tias kev hloov lub nplhaib aromatic nrog methoxy thiab hydroxy pawg muab nws cov polon analogs tshiab nrog kev ua haujlwm zoo, qee zaum txawm siab dua li ntawm nws tus polo nws tus kheej [236,237]. Qhov tseeb, hispolon derivatives dehydroxyhispolon methyl ether thiab hispolon methyl ether nthuav tawm siab dua hauv vitro cytotoxicity dua li hispolon tiv thaiv kab mob qog noj ntshav [238,239]. Cov tom kawg tau nce mus txog 5 zaug zoo dua rau txoj hnyuv thiab cov kab mob qog nqaij hlav prostate [239]. Dehydrohispolon yog ib qho kev cog lus antitubercular uas qhia qis MIC tiv thaiv M.tuberculosis nrog rau nws tus polon [240]. Hispolon thiab hispolon methyl ether pyrazole derivatives (Tebchaws 20) tau pom tias muaj kev ruaj ntseg zoo dua qub nrog rau lawv cov precursors nrog rau cov teebmeem antigenotoxic tiv thaiv hluav taws xob [241].

Cov pyrazole derivative kuj zoo dua li hispolon rau kev khawb N· thiab CCO,·radicals [242]. Ib tsev neeg ntawm palladium (II) complexes nrog hispolon analogs tau tsis ntev los no ua ke thiab lawv tau pom ntau dua hauv vitro cytotoxicity dua li cov ligands dawb sib txawv tiv thaiv kab mob qog noj ntshav sib txawv. Tshwj xeeb, Pd-complexes nrog methoxy-hloov hispolon analogs (Tebchaws 21) tau qhia txog kev ua haujlwm zoo dua piv rau cov sib txuas hydroxy sib txuas [243].

3.3. HydroxcytyroOsol

Hydroxytyrosol (2-(3,4-dihydroxyphenyl)ethanol) yog cov nroj tsuag theem nrab metabolite thiab nws muaj nyob rau hauv ntau cov txiv ntseej, ua lub luag haujlwm rau feem ntau ntawm lawv cov txiaj ntsig rau tib neeg kev noj qab haus huv. Kev cog lus tshuaj ua haujlwm ntawm hydroxytyrosol (raws li cardioprotective, anticancer, neuroprotective, thiab antimicrobial agent) tau raug tshuaj xyuas tsis ntev los no [79.244]. Analogously, hydroxytyrosol acetate (2-(3,4-dihydroxyphenyl)ethyl acetate), ib tug phenolic constituent ntawm txiv roj roj, yog tus yam ntxwv ntawm peculiar biological kev ua ub no [245-248]. Ob peb hydroxytyrosol derivatives tau tshawb nrhiav nyob rau xyoo dhau los, txhawm rau txuas ntxiv lawv cov kev siv roj ntsha [249-252]. Txawm li cas los xij, cov tswv yim ua haujlwm feem ntau suav nrog esterification lossis etherification ntawm pawg cawv-OH lossis hloov pauv ntawm lub nplhaib aromatic [253].

Piv txwv li, txhawm rau nthuav dav siv hauv cov khoom noj thiab tshuaj pleev ib ce,antioxidantlipophilic hydroxytyrosol esters tau raug tsim los ntawm esterification ntawm cov cawv-OH, nrog cov roj sib txawv [254-257], lossis los ntawm cov txheej txheem chemoselective transesterification [258]. Interestingly, decanoate thiab dodecanoic hydroxytyrosol esters ua rau cov tshuaj tiv thaiv zoo trypanosomal thiab anti-leishmanial agents, nquag tawm tsam T. brucei thiab L. donovani, feem [259]. Hydroxytyrosol antioxidant kev ua haujlwm tau txhim kho raws li esterification rau qhov sib thooj butyrate [260], fenofibrate [261], thiab nicotinate [262] esters (HT-1 thiab HT-2 raws li, Scheme 22), tom kawg kuj yog muaj zog-glucosidase inhibitor.

Ib yam li ntawd, polyacrylate polymer bearing hydroxytyrosol nyob rau hauv nws sab-chain nthuav tawm cov tshuaj tua kab mob antioxidant thiab tshuaj tua kab mob tiv thaiv Staphylococcus epidermidis [263]. Tsis tas li ntawd, hydroxytyrosol phosphodiesters (Scheme 23) yog cov tshuaj tiv thaiv antioxidant, tsim nyog rau kev tiv thaiv lossis kev kho mob.Alzheimer tus kab mob [264].

Ib yam li ntawd, hydroxytyrosol alkyl ethers yog tus cwj pwm los ntawm kev nthuav dav biomedical zog. Qhov tseeb, hydroxytyrosol hexyl ether pom antiangiogenic [265] thiab anti-platelet [266] cov teebmeem, thaum lub ethyl ether nthuav tawm txoj hnyuv tawm los tiv thaiv kab mob carcinogenic [267], nrog rau cov khoom tiv thaiv oxidant siab thaum ntxiv rau cov roj txiv roj ua lag luam [268. ]. Ntxiv mus, cov tshuaj muaj peev xwm ua haujlwm ntawm hydroxytyrosol glycosides tau tshawb pom tsis ntev los no; li no, neuroprotective hydroxytyrosol glycosides tau raug tsim los ntawm cov tshuaj tiv thaiv enzymatic, siv cov fungal -xylosidase ua cov catalyst los ua cov tshuaj tiv thaiv regioselective trans-xylosylation nrog xylobiose [269].

Nitrohydroxytyrosol, synthesized los ntawm cov tshuaj tiv thaiv ntawm hydroxytyrosol nrog sodium nitrite nyob rau hauv acetate tsis (pH 3.8), thiab nitro hydroxy tyrosyl ester derivatives (namely acetate, butyrate, hexanoate, octanoate, decanoate, laurate, myristate, thiab tau zoo palmitate) yields [270]. TSIS TAU,-hydroxytyrosol tau pom tias muaj kev txhim kho cov tshuaj tiv thaiv antioxidant nrog rau cov niam txiv compound, thaum cov kev ua ntawm ester derivatives yog nyob ntawm acyl saw ntev, tab sis cov txiaj ntsig zoo tau kuaj pom nrog acetate thiab butyrate. Ib yam li ntawd, cov tshuaj tiv thaiv antioxidant ntawm alkyl nitro hydroxy tyrosyl ethers tau khaws cia lossis txawm tias txhim kho rau ethyl thiab butylethers, thaum, nrog cov saw ntev ntev, nws tau txo qis nrog kev hwm rau hydroxytyrosol [271].

Lub synthesis ntawm alkyl carbonate derivatives ntawm hydroxytyrosol yog lub tswv yim los ua kom hydroxytyrosol antioxidant kev ua [272]. Carbonate derivatives tau ua tiav los ntawm ntau cov txheej txheem uas chloroformate hydroxytyrosol derivative (muaj kev tiv thaiv phenolic pawg) tau hnov ​​​​mob nrog alkyl cawv lossis diols ntawm cov saw ntev sib txawv [272,273](Scheme24). Hydroxytyrosol carbonates kuj tau nthuav tawm ntau dua kev tiv thaiv trypanosome tawm tsam Trypanosoma Brunei nrog kev hwm rau tus thawj [273].

4. Phenolic Acids

Phenolic acids yog hydroxy lossis methoxy derivatives ntawm benzoic acid los yog cinnamic acid (3-phenylpropanoid acid). Lawv diffused nyob rau hauv ntau yam nroj tsuag (piv txwv li, lawv yog cov feem ntau natural antioxidants ntawm nkauj xwb txiv roj roj [274]). Qhov ntau zaus phenolic acids tau sau tseg hauv daim duab 6.

Qhov tshwm sim, kev ua haujlwm lom neeg thiab tshuaj siv tshuaj ntawm monocyclic phenolic acids tau raug tshuaj xyuas, ua pov thawj lawv cov kev faib tawm dav thiab ntau yam haujlwm [275-277] ua ke nrog lawv cov ntawv cog lus kho mob [278-282]. Ua piv txwv, kev txhim kho gallic acid derivatives ua cov tshuaj pharmacological [283,284] tau tham tsis ntev los no. Ib yam li ntawd, cov yam ntxwv thiab muaj peev xwm siv tau ntawm ferulic acid derivatives [285-289] thiab cov khoom siv hluavtaws los ntawm caffeic acid [290] raug tshuaj xyuas.

Yog li ntawd, cov khoom txaus siab ntawm phenolic acid derivatives yog unambiguously affirmed. Txawm li cas los xij, hauv qab no, cov txiaj ntsig zoo tshaj plaws ntawm phenolic acids tau tham txog.

4.1.Caffeic Acid

Caffeic acid (3,4-dihydroxybenzoic acid) tuaj yeem pom hauv kas fes, cawv, thiab tshuaj yej. Nws yog tus yam ntxwv los ntawm kev ua haujlwm antioxidant, tshuaj tiv thaiv kab mob, thiab tshuaj tiv thaiv kab mob. Esters ntawm phenolic acids tau muaj kev txaus siab, thiab cov khoom siv lom neeg lom zem tshaj plaws thiab cov txheej txheem hluavtaws ntawm caffeic acid phenethyl ester thiab derivatives tau raug tshuaj xyuas [291]. Tseeb, caffeic acid phenethyl esters yog cov me me molecules nrog anti-inflammatory kev ua si rau kev kho mob ntawm mob ntsws mob [292]. Txoj hauv kev uas tsis yog ntuj biosynthetic tau tsim kho nrog caffeic acid rau hauv ntau yam cawv cawv lossis amine. Lub platform tshiab tso cai rau cov kab mob tsim tawm ntawm lub tsev qiv ntawv ntawm caffeic acid-derived phenethyl esters los yog amides hauv Escherichia coli[293](Scheme 25).

Caffeic acid enzymatic esterification nrog phenethyl cawv nyob rau hauv lub xub ntiag ntawm Novozym 435 nyob rau hauv isooctane ntawm 70 degree tau exploited [294]. Lub enzyme khaws ntau tshaj 90 feem pua ​​​​ntawm nws cov haujlwm qub mus txog qhov thib peb. Nws yog tsim nyog qhia tias lub enzymatic synthesis ntawm caffeic acid phenethyl ester tau ntse ultrasound-accelerated [295]. Ib yam li ntawd, kev hloov pauv ntawm methyl caffeate rau caffeic acid phenethyl ester analogs tau ua nrog Candida Antarctica lipase B, siv cov kua ionic 1-butyl-3-}methylimidazolium bis (trifluoromethyl sulfonyl) imide ua cov kuab tshuaj [296]. 2-Cyclohexylethyl caffeate thiab 3-cydlohexylpropyl caffeate pom muaj zog tiv thaiv kab mob. Alkyl esters ntawm caffeic acid nrog 2-8 C atoms tau txais los ntawm caffeic acid thiab cawv kom zoo nyob rau hauv muaj DCC [297]. Kev tshuaj xyuas rau lawv cov tshuaj tiv thaiv kab mob tau ua tawm tsam Candida albicans, nrog rau kev ua yeeb yam zoo tshaj plaws los ntawm propyl caffeate. Lwm cov alkyl esters ntawm caffeic acid (alkyl =}methyl, ethyl, butyl, octyl, benzyl, thiab phenethyl) tau npaj rau reflux caffeic acid nrog alkanol hauv acetyl chloride [298]. Hauv vitro thiab hauv vivo kev sim tau lees paub qhov kev tiv thaiv kev ua haujlwm ntawm cov esters.

Nees nkaum-ib caffeic acid phenethyl ester derivatives tau tsim, tsim, thiab tshawb xyuas rau lawv cov teebmeem cytoprotective [299]. Qee tus ntawm lawv tau pom muaj zog cytoprotective kev ua ub no ntau dua li cov niam txiv phenethylester, yog li cov kws sau ntawv tau qhia txog qhov muaj peev xwm ua tau zoo raws li cov khoom xyaw rau kev tiv thaiv cov kab mob neurodegenerative.

Caffeic acid thiab nws cov phenyl propyl ester tau tshawb xyuas rau lawv lub peev xwm los tiv thaiv kev loj hlob ntawm tib neeg cov qog nqaij hlav qog noj ntshav hauv vitro thiab hauv vivo [300], uas ua rau muaj zog tiv thaiv kab mob cancer.

Nees nkaum ester derivatives ntawm caffeic acid tau tsim los tshawb xyuas cov haujlwm inhibitory tawm tsam nitric oxide ntau lawm vim lipopolysaccharides [301]. Tag nrho cov ntawm lawv pom muaj inhibitory kev ua si.

Semi-synthetic esters derivatives ntawm caffeic acid nrog ib tug triazole moiety tau tsim raws li tej zaum 5-lipoxygenase inhibitors [302].5-Lipoxygenase yog koom nrog hauv biosynthesis ntawm leukotrienes, paub zoo inflammatory mediators nrog cuam tshuam. nyob rau hauv ntau yam kab mob (asthma, allergic rhinitis, kab mob plawv, thiab tej yam mob cancer). Cov qauv tsim qauv siv tshuaj xa cov khoom sib txuas nrog zoo heev 5-lipoxygenase inhibition, tshwj xeeb tshaj yog cov tebchaw qhia hauv Scheme 26 uas tau qhia txog kev ua haujlwm zoo dua qub piv rau caffeic acid.

Amides tau raug xaiv los ua bioactive derivatives ntawm caffeic acid: ob peb alkyl thiab aryl amines tau siv los npaj antioxidant caffeic acid derivatives [303]. Anilides ntawm caffeic acids tau pom tias muaj txiaj ntsig zoo li lipid peroxidation inhibitors.

Txij li thaum qee cov nroj tsuag tau txais los ntawm polyphenols tau pom los siv cov tshuaj tiv thaiv kab mob tiv thaiv kab mob khaub thuas, inhibiting tus kab mob ntawm cov protein neuraminidase, lub tsev qiv ntawv ntawm caffeic acid-based compounds tau tsim, tsim ntau yam hloov amides [304]. Cov amides tau nthuav tawm ib qho kev ua haujlwm nruab nrab ntawm neuraminidases thiab cov ntaub ntawv pov thawj hauv daim duab 7 yog qhov pheej hmoo tshaj plaws.

Amides tau npaj los ntawm caffeic acid thiab heteroaromatic amine tacrine nrog alkyl spacers ntawm qhov ntev sib txawv (Scheme 27) [305]. Tag nrho cov tacrine derivatives muaj ntau npaum li cas antioxidant efficiency tshaj caffeic acid. Tshwj xeeb, qhov sib xyaw nrog a3 Clinker thiab Cl atom hauv lub nplhaib aromatic yog qhov xaiv ntau dua, vim tias nws muaj cov nyhuv neuroprotective muaj zog, inhibiting -amyloid aggregation. Cov khoom no ua rau amide ib tus neeg sib tw zoo rau kev txhim kho cov cuab yeej kho mob zoo hauv kev kho mob Alzheimer's.

Ib tug xov tooj ntawm acyl hydrazides ntawm caffeic acid tau npaj thiab soj ntsuam rau kev tiv thaiv inflammatory, analgesic, thiab ulcerogenic kev ua ub no [306]. Caffeic acid yog tert-butylated nyob rau hauv txoj hauj lwm 5 ntawm lub nplhaib aromatic 307]. Ob leeg caffeic thiab t-butylated caffeic acids pom muaj zog antioxidant muaj peev xwm thaum lub sij hawm squalene peroxidation nyob rau hauv ncaj qha UVA irradiation, tab sis tsuas yog tom kawg yuav txo tau cov tiam ntawm reactive oxygen hom.

4.2.Ferulic Acid

Ferulic acid (4-hydroxy-3-methoxy cinnamic acid) yog ib qho zoo antioxidant compound, feem ntau pom muaj nyob rau hauv cov noob, nplooj, nrog rau hauv cov nroj tsuag cell phab ntsa. Ob peb ferulic acid derivatives tsis ntev los no tau tshawb nrhiav hauv ntau qhov chaw. Lipases los ntawm Candida Antarctica (Novozyme 435), Candida rugosa, Chromobacterium viscosum, thiab Pseudomonas sp. tau siv los catalyze transesterifications ntawm vinyl ferulate nrog hydroxyl steroids thiab arbutin [308](Scheme 28). Arbutin ferulate muaj 19 feem pua ​​​​ntawm cov tshuaj tiv thaiv kab mob ntau dua li ferulic acid.

Lwm cov tshuaj tiv thaiv enzymatic esterification tso cai rau kev sib txuas ntawm ethyl ferulate los ntawm ferulic acid thiab ethanol, siv Novozym 435 ua biocatalyst, uas tuaj yeem rov siv tau yim zaug ua ntej kev ua haujlwm tseem ceeb [309]. Lipase-catalyzed kev npaj ntawm mono-thiab diesters ntawm ferulic acid tau tshaj tawm 310]. Qhov tseeb, kev siv lub peev xwm antioxidant ntawm ferulic acid yog txwv los ntawm nws qhov tsis txaus solubility hauv hydrophobic media xws li rog thiab roj. Ib lub tswv yim los ua kom cov txiaj ntsig kho tau zoo tshaj plaws yog hloov cov kua qaub rau hauv esters [31l](Scheme 29). Thaum npaj, esters tau soj ntsuam rau hauv vitro antioxidant peev xwm. Ntxiv mus, molecular docking qhia tau hais tias ferulic esters inhibit lub hom phiaj proteins nyob rau hauv lub mis mob cancer thiab nyob rau hauv oxidative kev nyuaj siab.

Alkyl esters thiab amides ntawm ferulic acid tau npaj thiab tshuaj xyuas rau lawv cov kev tiv thaiv kab mob cancer [312]. Raws li cov kws sau ntawv, tag nrho cov synthesized amides pom zoo cytotoxic kev ua si, ib tug yam ntxwv ntawm lipophilicity. Ob peb amides ntawm hloov ferulic acids kuj tau npaj los ntawm O-acetyl feruloyl chloride nrog amines [313]. Feem ntau ntawm cov amides tau nthuav tawm qhov tseem ceeb ntawm kev tso tawm insulin los ntawm nas pancreatic hlwb.

Ib tug xov tooj ntawm amides tau npaj los ntawm ferulic acid thiab lwm yam phenolic acids (Scheme 30), nrog rau lub hom phiaj los soj ntsuam lawv cov kev ua antioxidant [314]. Cov txiaj ntsig ntawm plaub qhov sib txawv hauv vitro xeem tau qhia tias muaj kev ua haujlwm antioxidant siab heev, tshwj xeeb tshaj yog thaum-OH lossis -OMe pab pawg muaj nyob hauv amide.

Ob peb ferulic acid amides thiab amides ntawm tus coj 3-(4-ethoxy-3-hydroxy) phenylpropanoid acid tau ua ke thiab sim rau cov tshuaj tua kab mob thiab tshuaj tua kab, tawm tsam cov kab mob luam yeeb mosaic[315]. Feem ntau ntawm cov tshuaj amides tau nthuav tawm tsis yog tsuas yog cov tshuaj tua kab mob zoo, inhibiting cov kab mob ntawm cov nroj tsuag, tab sis kuj muaj cov tshuaj tua kab tiv thaiv kab mob, yog li pab tiv thaiv kab mob sib kis hauv cov qoob loo (Daim duab 8).

Amides ntawm hydrogenated ferulic acid, 3-(4-hydroxy-3- ethoxy) phenylpropanoid acid, tau ua ke (Scheme 31) [316]. Qee tus ntawm lawv tau nthuav tawm kev tiv thaiv zoo heev thiab kev ua haujlwm kho mob tiv thaiv tus kab mob luam yeeb mosaic.

Cov pab pawg feruloyl thiab phenethyl tau ua ke los ua ke los ua ke rau ester phenethyl trans-3-(4-hydroxy-3-methoxyphenyl)acrylate thiab amide trans-3-(4-hydroxy{ {5}}methoxyphenyl)-N-phenethylacrylamide [317]. Phenethyl ester thiab amides tau kawm txog bioactivity raws li cov tshuaj tiv thaiv kab mob, ua pov thawj zoo dua li cov niam txiv compound [318].

Ntau lwm yam amides ntawm ferulic acid tau npaj nyob rau hauv hnyav-dawb tej yam kev mob los ntawm MW-pab condensation cov tshuaj tiv thaiv [319]. Nees nkaum-ib amides tau pom pom pom hauv vitro anticancer kev ua, cuaj nthuav tawm hauv vitro dawb radical scavenging kev ua haujlwm siab dua li ntawm ferulic acid.

Hexyl caffeate thiab ferulate, nrog rau caffeovlhexylamide thiab ferulovlhexylamide, tau sim hauv tib neeg cov kab mob qog noj ntshav ntawm lub mis [320]. Sib txawv los ntawm niam txiv cov tebchaw, cov tebchaw tshiab inhibited cell proliferation thiab induced cell cycle alternations and cell death.

Nees nkaum xya ferulic acid derivatives, nrog halogens-acetanilide li tshiab nto kev paub moiety, tau npaj nrog lub hom phiaj kom tau txais cov tebchaw muaj peev xwm ua raws li histone deacetylase inhibitors. Cov chav kawm tom kawg ntawm cov ntsiab lus tseem ceeb rau kev kho mob qog noj ntshav [321]. Synthesized tebchaw pov thawj nyob rau hauv qab ntawm Scheme 32 nthuav tawm qhov tseem ceeb enzymatic inhibitory kev ua ub no.

Qhov tseem ceeb, geranylated derivative ntawm ferulic acid, 3-(4O-geranyloxy-3-methoxyphenyl)-2-propenoate ua rau muaj kev ua haujlwm ntau dua li niam txiv ferulic acid ua tus neeg sawv cev inhibitory ntawm aberrant crypt foci, txo Qhov tshwm sim ntawm adenocarcinomas hauv txoj hnyuv [322].

4.3. Lwm yam

Methyl, ethyl, propyl, thiab butyl esters ntawm sinapic acid (4-hydroxy-3, 5-dimethoxycinnamic acid, bioactive natural compound pom nyob rau hauv txiv hmab txiv ntoo, zaub, thiab tshuaj nroj tsuag), pre- pared los ntawm acid-catalyzed esterification ntawm cawv, nthuav qhia yuav luag tib yam antioxidant kev ua, uas yog me ntsis qis dua li ntawm sinapic acid [323]. Txawm li cas los xij, lawv muaj qhov zoo ntawm lipophilicity ntau dua, uas muaj txiaj ntsig zoo rau cov tshuaj tua kab mob antioxidant tsim los ua cov tshuaj tiv thaiv membrane hauv vivo.

Alkyl esters ntawm protocatechuic thiab gallic acids (3,4-dihydroxybenzoic acid thiab 3,4,5-trihydroxy benzoic acid, raws li), npaj reacting cov kua qaub nrog sib txawv alkanols nyob rau hauv muaj DCC, tau pom los inhibit HIV-1 protease dimerization [324], nrog rau kev ua tau zoo nyob ntawm qhov ntev ntawm cov saw hlau alkyl. Qhov tseeb, tsis muaj kev cuam tshuam nrog cov saw hlau alkyl nrog tsawg dua yim carbon atoms. Protocatechuic acid thiab nws cov ethyl thiab heptyl esters tau tshawb xyuas rau kev tiv thaiv kev ua haujlwm [325]. Lub photoprotection thiab antiaging kev ua tau siab dua nrog cov esters dua nrog cov niam txiv acid, tej zaum vim lawv cov lipophilicity siab dua. Hmoov tsis zoo, cytotoxicity kuj nce ntxiv.

Alkyl esters ntawm gallic acid tau npaj los ntawm classical Fisher esterification, los ntawm cov kua qaub thiab cawv hauv cov kua qaub nruab nrab [326]. Dhau li ntawm cov tshuaj tiv thaiv kab mob, tshuaj tiv thaiv kab mob thiab tshuaj tua kab mob, lawv muaj peev xwm tshem tawm thiab txo cov kab mob reactive oxygen. Tsis tas li ntawd, gallic acids esters yog cov muaj peev xwm inhibitors ntawm metastasis [327]. Lub propyl ester ntawm gallic acid tau hloov mus rau hauv acyl hydrazide uas, thaum cov tshuaj tiv thaiv nrog cov chalcone tsim nyog, tau hloov mus rau hauv pyrazole derivatives ntawm gallic acid [328]. Cov tebchaw tau raug tshuaj xyuas rau lawv cov tshuaj tiv thaiv kab mob, nrog rau cov txiaj ntsig zoo hauv qee kis.

Tshiab syringic hydrazones los ntawm aldehyde ntsig txog syringic acid (4-hydroxy-3, 5-dimethoxybenzoic acid) thiab hloov hydrazines (nrog electron- rho tawm lossis electron attracting pab pawg) [329] tau zoo tiv thaiv oxidative kev nyuaj siab.