Chemical Constituents Ntawm Nplooj Ntawm Cistanche Ⅱ

3. Kev sib tham

Kev tshawb nrhiav phytochemical txhawm rau txheeb xyuas cov tshuaj lom neeg lom neeg hauv cov nplooj persimmon tau ua tiav. Txog tam sim no, ntau tus lej ntawm triterpenoids thiab flavonoids, suav nrog kaempferol thiab quercetin derivatives, tau tshaj tawm los ntawmD. kev[1]. Hauv txoj kev tshawb no, peb tau txais 27 lub tebchaw, suav nrog kaum rauflavonoids, ib ionone, ob coumarins, xya triterpenoids, thiab ib tug acetophenone. Ntawm no, compound1 tau pom tias yog ib qho tshiab flavonoid thiab compound2 yog thawj zaug cais tawm ntawmD. kev. Tsis tas li ntawd, kaempferol -3-O- -200 - feruloyl glucoside (3) tsuas yog tshaj tawm raws li cov khoom siv hydrolyzed ntawm 3-O- -(2-O-feruloyl)-glucosyl-7,40 -di-O- -glucosyl kaempferol (3), cais los ntawmAllium tuberosum[35]. Compound3 tsis tau tsuas yog tau ncaj qha los ntawm ib tug natural qhov chaw thawj zaug tab sis kuj tsis tau qhia nyob rau hauvD. kevyav dhau los. Tsis tas li ntawd, kaempferol-3-O- -200 -galloyl galactoside (nrog rau11) tau raug tshaj tawm yav dhau los hauv ntau qhov chaw, suav nrogD. kev, tab sis tsuas yog cov1H NMR thiab MS tau tshaj tawm vim tsis muaj kev tshawb fawb ntxaws. Li no, lub13C NMR cov ntaub ntawv tau tshaj tawm thawj zaug ntawm no.

Txog rau tam sim no, muaj ob peb txoj kev tshawb fawb uas pom tau tias muaj peev xwm tiv thaiv oxidative ntawm cov extracts los yog feem ntawm cov nplooj persimmon [37,38]. Feem ntau cov kev tshawb fawb tau siv txoj kev ntsuam xyuas sai xws li DPPH lossis ABTS kev soj ntsuam. Tshwj xeeb, hauv daim ntawv dhau los, 200µg / mL ntawm flavonoid-nplua nuj feem pom 68.73 feem pua ​​​​ inhibition ntawm DPPH radical. Ntxiv nrog rau qhov tshwm sim no, txawm li cas los xij, qhov seem no kuj pom muaj superoxide anionradical scavenging, hydroxyl radical scavenging, thiab hlau chelating kev ua ub no [38]. Txawm hais tias peb tsis tau soj ntsuam cov kev ntsuam xyuas no, bioassay-coj kev cais tawm tau ua tiav vim tias cov ethanol extract thiab ethyl acetate feem hauv txoj kev tshawb fawb tam sim no pom tau tias piv rau DPPH radical scavenging kev ua si. Tsis tas li ntawd, txawm tias cov txiaj ntsig yav dhau los, tsuas yog ob peb txoj kev tshawb fawb los txheeb xyuas cov tshuaj lom neeg lom neeg tau ua tiav. Ob peb secoiridoids thiab lignans pom radical scavenging kev ua ub no [39]. Nyob rau hauv cov ntaub ntawv ntawm flavonoids, muaj ntau cov ntaub ntawv qhia tias quercetin, kaempferol, thiab lawv glycosides muaj antioxidative zog [40]. Antioxidative zog ntawm faib kaempferol glycoside thiab faib quercetin glycoside tau los ntawm lwm qhov chaw tau tshaj tawm [41]. Txog tam sim no, tseem tsis tau muaj lus ceeb toom tias txhua qhov sib xyaw nomuab tau los ntawm cov nplooj persimmon muaj cov tshuaj tiv thaiv oxidative, tshwj tsis yog tias kev sib xyaw ntawm cov tshuaj no tau nthuav tawm cov nyhuv antioxidative [21]. 

Tsis tas li ntawd, kom deb li deb, kev txiav txim siab ib txhij ntawm tsuas yog ob peb triterpenoids lossis flavonoids tau ua tiav rau kev txheeb xyuas ntau ntawm cov tebchaw no [42,43]. Txawm li cas los xij, txoj kev tshawb no qhia txog ib txoj hauv kev rau kev txiav txim siab ib txhij ntawm feem ntau ntawm cov nplooj persimmon.

Nyem qhov no kom tau txais Kev Paub Ntxiv Txog Yuav Ua Li Cas Cistanche Anti-Aging

4.1. Khoom siv cog

Nplooj ntawmDiospyros kakiThunb. (Ebenaceae) tau yuav ntawm ib lub teb chaws KauslimKev lag luam tshuaj ntsuab hauv Yeongcheon thaum Lub Peb Hlis 2018. Cov nplooj tau sau rau ntawm thaj chaw phiab puag ncig roob ntawm qhov siab ntawm 800-1200 m hauv Gyeongsangbuk-do thaum Lub Yim Hli 2017. Qhov nruab nrab ntawm cov nag lossis daus txhua xyoo hauv cheeb tsam no yog 1050 hli,ntawm qhov ntawd, ib nrab poob thaum Lub Rau Hli thiab Lub Yim Hli. Qhov nruab nrab txhua xyoo kub yog hais txog12.5 ◦C thiab qhov nruab nrab cov av noo yog 69 feem pua. Qhov kub ntawm lub sij hawm sau qoob yogib 37-40◦C. Cov nplooj tau qhuav ntawm kwv yees li 45◦C nyob rau hauv ib tsob nrojtshuab ziab khaub ncaws. Daim ntawv pov thawj (DIKA1-2018) tau muab tso rau hauv Laboratory of NaturalKhoom Siv Tshuaj, Tsev Kawm Qib Siab Pharmacy, Kyung Hee University, koom pheej ntawm Kaus Lim Kauslim.

4.2. Cov txheej txheem kev sim dav dav

silica gel (ODS-A 12 nm S{2}}µm, YMC, Tokyo, Nyiv). Flash chromatography yog pertsim siv lub CombiFlash (Teledyne Isco, Lincoln, NE, USA) nrog cov ntawv ntim ua ntej,RediSep-silica (12 g, 24 g, thiab 40 g), thiab RediSep-C18 (13 g, 26 g, 43 g, thiab 130 g). Npajtiv thaiv HPLC tau ua tiav siv Gilson purification system (Gilson, Middleton, WI,Tebchaws Asmeskas) nrog YMC Pob ODS-A kem (250× 2 0 0 mm, 5.0µm, YMC, Tokyo, Nyiv), ib puag ncigODS-M80 kem (250× 200 mm, 4.0µm, YMC, Tokyo, Nyiv), thiab Luna C18(2)kab (250× 21.2 hli, 10.0µm, Phenomenex, Torrance, CA, USA). Kev tshuaj xyuas HPLC yogua ntawm Youngin YL9100 HPLC system suav nrog lub teeb evaporative tawgdetector (Youngin, Anyang, Kauslim) nrog Luna C18(2) kem (150× 4.6 hli, 5. 0µm, Phenomenex, Torrance, CA, USA). Kev tshuaj xyuas HPLC-ABTS online tau ua tiav rauAgilent 1200 HPLC system nrog YMC Pob ODS-A kem (150× 4.6 hli, 5. 0µm). Tag nrho cov kuab tshuaj siv rau kev sib cais chromatographic tau distilled.

4.3. Extraction thiab rho tawm

Cov khoom cog qhuav (15.0 kg) tau muab rho tawm nrog 216 L ntawm ethanol (EtOH) hauv ib qhoda dej ntawm 60◦C rau 4 h, thiab cov kuab tshuaj tau evaporated kom tau txais EtOH extract (1.2 kg,yield 8 feem pua). Cov extract tau raug tshem tawm hauv H2O (2.1 L) thiab muab faib nrog ethyl acetate(EtOAc, 4.9 L× 3) muab EtOAc- (321.9 g, tawm los 2.15 feem pua) thiab H2O-soluble txheej (748.0 g,yield 4.99 feem pua), feem. EtOAc-soluble txheej (321.9 g) tau raug silica gelkem (φ 10.5 × 35. 0 cm) nrogn- exane: EtOAc: methanol (MeOH) sib tov (los ntawm 8: 1.8: 0.2rau {0}}:0:1v/v/v) kom them tau cuaj feem (E1 ~ E9).

Fraction E5 (14.2 g) tau chromatographed hla Diaion HP-20 kab (φ 5.0 × 29.0 cm) nrog acetone: H2O gradient (7:3 txog 1:0) kom them tau xya feem (E5-1~E5-7). Tshooj E5-1 yograug rau silica gel kem nrogn-hexane:EtOAc: MeOH=7:2.7:0.3 rau 0:0:1 rau them 4 feem(E{{0}}}~E5-1-4). E5-1-1 (13.2 mg) thiab E5-1-2 (7.0 mg) tau muab tso ua ke thiab huv si los ntawm kev npaj(prep)-HPLC siv YMC Pob ODS-A kem (H2O: MeOH=27:23,7 ml / min) kom tautshuaj sib xyaw19 (8.3 mg, tR 26.0 feeb) thiab20 (2.5 mg, tR 24.0 feeb).

Fraction E8 (75.19 g) tau muab faib ua acetone-soluble (AS) thiab acetone-insoluble(AIS) fractions. Fraction AS (44.07 g) tau chromatographed hla Diaion HP-20 kab(φ 6.5 × 12.5 cm) nrog acetone: H2O sib tov (3: 7 rau 1:0) kom them taus 12 feem (AS1 ~ AS12).Fraction AS2 (2.5 g) tau sib cais los ntawm Sephadex LH-20 kem (φ 4.7 × 51. 0 cm) nrogMeOH muab cuaj feem (AS2-1~AS2-9). Fraction AS 2-2 (196.3 mg) raug cais los ntawmflash chromatography (FC) siv lub RediSep-C18 cartridge (26 g, acetonitrile: H2O, 0:1 rau7: 1) ua kom sib xyaw ua ke17 (28.6 mg). Fraction AS3 (3.1 g) tau muab cais ua 11 feemsiv Sephadex LH-20 kem (φ 4.7 × 51.0 cm) with MeOH (AS3-1~AS3-11).

Ib feemAS {{0}} (0.7 g) tau sib cais los ntawm FC nrog RediSep-C18 (130 g, MeOH:H2O, 1:9 txog 3:2) muabtshuaj sib xyaw4 (51.8 mg),5 (21.7 mg, tR 42,5 min), thiab6 (20.2 mg, tR 47.0 feeb). Fraction AS4 (8.8 g) tau raug rau ntawm silica gel kem (φ 5.2 × 21.0 cm) nrog MC:MeOH:H2O sib tov (ntawm 8: 1.8: 0.2 rau 7: 2.7:0.3) kom cais cov Compounds7 (5. 0 mg),8 (5.1 mg),9 (2 0.0 mg), 10 (306.6 mg), thiab12 (20.1 mg). Fraction AS5 tau raug rau ntawm silica gel kem (φ 5.2 × 24.5 cm)nrog CH2Cl2:MeOH: H2O sib tov (8:1.8:0.2 rau 7:2.7:0.3) los tsim rau 6 feem (AS5-1~AS5-6) kom them nyiaj sib txuas11 (3.0 mg) thiab13 (7.4 mg). Fraction AS10 tau sib caisrau hauv xya feem siv Sephadex LH-20 kab (φ 3.5 × 50.5 cm) nrog MeOH (AS10-1~AS10-7). Fraction AS 10-4 tau cais los ntawm FC nrog RediSep-C18 (43 g, MeOH: H2O,

0: 1 mus rau 3: 2) cartridge los ntxuav cov tebchaw1 (5.3 mg),2 (21.4 mg),14 (15.9mg 3), thiab15 (40.4 mg). Fraction AS12 tau muab cais ua tsib feem siv Sephadex LH-20 kem (φ 3.5 × 50.5 cm) with MeOH (AS12-1~AS12-5). Compound16 (20.1 mg) tau los ntawmrecrystallization nrog MeOH los ntawm feem AS 12-5.

Fraction Als (31.1 g) yog chromatographed silica gel kem nrog h hexane EtOAc: MeOH sib tov (8:1.8:0.2 rau 0:0:1) raws li theem mobile rau afford 20 feem (AIS1-AIS2{{20}})Fraction AlS5 tau raug rau silica gel kem nrog n-hexane:EtOAc:MeOH mixs(8:1.8: {{30}}.2 rau 0:0:1) them nyiaj 23 (224.7 g). Fraction AIS6 tau sib cais los ntawm FCwith a RediSep-C18 (43 g, MeOH:HO, 0: 1 txog 9: 1) cartridge muab cov khoom sib xyaw 25 (25.6 mg) Fraction AIS7 tau raug rau silica gel kem nrog n -hexane:EtOAc: MeOH mixs(8:1.8:0.2 to {{60}}}:0:1) to afford compounds 24 (10} 0.0 mg) thiab 27 (214.1 mg). Fraction AIS10 tau raug rau silica gel kem nrog n-hexane: EtOAc: MeOH sib tov (7: 2.7: 0.3 txog 0: 0: 1) kom cais cov tebchaw 18 (5.0 mg) thiab 23 (16.7 mg). Fraction AIS11 tau muab cais ua 11 ntu (AIS11-1-AIS11-11) los ntawm FC nrog RediSep-C18 (130 g, MeOH:HO, 1: 1 txog 4: 1)cartridge. Compound 22 (37.8 mg) tau los ntawm feem AS11-4 los ntawm prep-HPLC nrog ib kab ke. Fraction AIS12 tau raug rau silica gel kem (o 5.2 x 28.0 cm) nrog HCl: acetone sib tov (los ntawm 4: 1 txog 3: 2) kom them tau cov khoom sib xyaw 21 (188.0 mg). Thaum kawg, fractionAIS16 tau sib cais siv Lichroprep RP-18 kem (1.99 g, MeOH: H2O, 3: 2 txog 13: 7) toobtain compound 3 (2.3 mg).

4.3.1. kaempferol -3-O- -D-200 - coumaroylgalactoside (1

) Yellowish hmoov; mp244.5 ua◦C; [ ] 22 D -59.1◦ (c 0.1, MeOH); UV (MeOH)λmax(logε) 207 nm (3.98), 315 nm (3.92); IR (ATR)νmax3458, 2922, 1650, 1588, 1364, 1260, 1175, 1076, 834 cm−1 ; 1H thiab13C NMR cov ntaub ntawv, saib Table1; HRMS (zoo hom)m/z 595.1447 [M ntxiv rau H]ntxiv(Calcd rau C30H27O13, 595.1452). 

4.3.2. kaempferol -3-O- -D-200 - feruloylglucoside (3) 

Yellowish hmoov; mp 225.2 ua◦C; [ ] 22 D -119.6◦ (c 0.1, MeOH); UV (MeOH)λmax(logε) 210 nm (4.17), 327 nm (3.94); IR (ATR)νmax3369, 1652, 1599, 1512, 1360, 1264, 1177, 1076, 841 cm−1 ; 1H thiab13C NMR cov ntaub ntawv, saib Table1; HRMS (qhov tsis zoo)m/z 623.1375 [M − H]− (Calcd rau C31H27O14, 623.1401).

4.3.3. kaempferol-3-0--D-2-galloylgalactoside (11)

Cov hmoov daj; HNMR (500 MHZ, DMSO-) 6 H NMR 8.06 (2H, d,J= 9.0 Hz, H{ {8}}H-6'), 7.02 (2H, S, H-3, H-'), 6.87 (2H, d, I=9} .5 H, H-, H-5, 6.39 (1H, S, H-8), 6.16(1H s, H{29}}), 5.78 (1H, d, {{33) }}.0 Hz, H-1 feem pua ​​,5.27 (1H, t, =9.5 Hz H-2" 13C NMR (125 MHz DMSO-6) {{45 }}.1 (C-4), 165.4 (C-7), 165.4 (C-1), 161.2 (C-5), 160.1 (C{59}) }, 156.3 (C-2), 156.3(C-9), 145.5 (C-4"), 145.5 (C-6), 138.4 (C{{74}) }/), 132.5 (C-3), 131.0 (C-2'), 131.0 (C-6), 120.7 (C1), 119.8 (C-2') , 115.2 (C-3'), 115.2 (C-5), 108.9 (C-3), 108.9 (C-7), 103.8 (C{104}}) , 98.8 (C-6) 98.8 (C-1 feem pua), 93.7 (C-8), 76.0 (C-5), 72.7 (C{119}}) , 71.1 (C-2%), 68.2 (C-4"), 60.1(C-6").

4.4. Ouantitative Analsis ntawm Nine Compounds hauv Persimmon Lenves

Kev tshuaj xyuas HPLC tau ua tiav ntawm Waters HPLC system suav nrog 1525 twj thiab 2996 photodiode array detectors (Waters, Milford, MA, USA). UV wavelength tau teeb tsa ntawm 260 nm. A PhenomenexLuna C18(2) kem (150 x 4.6 mm,5.0 um, Phenomenex, Torrance, USA) tau siv, thiab qhov ntim txhaj tshuaj yog 10 uL. Qhov kub thiab txias yog teem rau ntawm 25 degree. Cov theem ntawm lub xov tooj ntawm tes muaj 0.02 feem pua ​​​​ntawm trifluoroacetic acid (TFA, Sigma-AldrichSt. Louis, MO, USA) hauv dej (A) thiab acetonitrile (B) nrog tus nqi ntws ntawm 0.7 mL / min. Cov xwm txheej gradient tau raws li hauv qab no: 0-30 min, 15-20 feem pua ​​B; 30-45 min, 20-35 feem pua ​​B: 45-70 min35-100 feem pua ​​; 70-80 min, 100 feem pua. EtOH extract (10 mg) yog yaj nyob rau hauv 10 ug / mL sab hauv txheej txheem tov (1 mL). Txoj kev siv tau yooj yim tau ua tiav los xyuas kom meej qhov tseeb ntawm cov qauv tsim thiab cov txiaj ntsig zoo. Tsib qhov kev daws teeb meem sib txawv ntawm txhua qhov sib xyaw tau txheeb xyuas los ua kom txhua qhov kev sib tw calibration. Lub intra- thiab inter-hnub precision thiab raug raug lees paub los ntawm peb replicates nyob rau hauv ib hnub thiab peb hnub sib law liag. Tag nrho cov qauv raug lim los ntawm 0.2 um membrane lim.

4.5. DPPH thiab Online HPLC-ABTS Analysis

Lub peev xwm ntawm cov qauv rau kev tshem tawm DPPH radicals tau soj ntsuam raws li daim ntawv dhau los. Luv luv, DPPH ({{0}}.1 mM) hauv methanol (100 uL) tau sib xyaw nrog ntau qhov sib txawv ntawm cov qauv (100 uL) rau 1 teev hauv qhov tsaus ntuj. Qhov nqus tau raug kaw ntawm 517 nm.Qhov kev tshuaj ntsuam xyuas online HPLC-ABTS tau ua raws li daim ntawv tshaj tawm dhau los nrog kev hloov kho. Cov tshuaj sib xyaw uas muaj ABTS (0.08 mM) nrog cov poov tshuaj persulfate (0.12 mM) tau ua rau hauv ABTS reagent. Cov reagent tau khaws cia ntawm 4 C rau 12 teev kom ruaj khov radicals. Tag nrho cov qauv raug tshuaj xyuas los ntawm Agilent HPLC system. Cov xwm txheej gradient tau zoo ib yam li cov uas siv rau kev txheeb xyuas qhov ntau. Cov eluate raug xa mus rau qhov ua haujlwm thiab ua haujlwm nrog ABTS reagent hauv cov tshuaj tiv thaiv kauj ntawm 40 degree. Lub chromatogram tau pom ntawm 254 nm (qhov zoo tshaj plaws), nrog rau ntawm 734 nm (tsis zoo ncov), txhawm rau sau nws qhov txo qis ntawm aBIS radicals.

5. Cov ntsiab lus xaus, qhov kev tshawb fawb no nthuav tawm kev tshawb nrhiav phytochemical raws li kev cais tawm bioassay-coj. Raws li qhov tshwm sim, ib qho tshiab flavonoid, kaempferol-3-0-BD-2"-coumaroylgalactoside(1), thiab lub ntuj tshiab, kaempferol-3-0--D-2"-feruloylglucoside (2 ), raug cais nrog 25 yam uas paub yav dhau los, suav nrog kaum plaub flavonoids, ib qho ionone, ob coumarins, xya triterpenoids, thiab ib qho acetophenone. Tag nrho cov tebchaw tau soj ntsuam los ntawm cov tshuaj tiv thaiv oxidative, thiab ntawm no, cuaj flavonoids tau pom muaj cov dej num. Kev soj ntsuam ib txhij kom muaj nuj nqis tau ua kom paub tseeb tias cov nplooj persimmon muaj cov tshuaj tiv thaiv oxidative vim cov tebchaw no.

Cov khoom siv ntxiv:Cov hauv qab no muaj nyob online ntawmhttps://www.mdpi.com/article/10 .3390/plants10102032/s1, Figures S1–S9: Lub 1H, 13C, COSY, HSQC, HMBC, thiab ROESY NMR, UV, IR, thiab HRMS spectra of compound 1, Figures S10–S18: The 1H, 13C, COSY, HSQC, HMBC, ROESY NMR , UV, IR, thiab HRMS spectra of compound 3, Figures S19–S20: The 1H and 13C NMR spectra of compound 11, Table S1: Kev txheeb xyuas ntau ntawm lwm cov 18 tebchaw.

Tus sau kev koom tes:JK thiab J.-EP tau muab kev koom tes sib npaug rau txoj kev kawm no; conceptualization, H.-CK thiab D.-SJ; methodology thiab validation, JK, J.-EP, J.-SL, J.-HL thiab HH; software,JK thiab J.-SL; validation, JK thiab HH; kev soj ntsuam, JK thiab J.-EP; kev tshawb nrhiav, JK, J.-EP,J.-SL, J.-HL, HH, S.-HJ, H.-CK and D.-SJ; Resources, H.-CK thiab D.-SJ; data curation, JK, J.-EP thiab J.-SL; sau ntawv—kev npaj ua ntej, JK, J.-EP thiab J.-SL; sau ntawv— tshuaj xyuas thiab kho, H.-CK thiab D.-SJ; kev pom, JK thiab J.-SL; kev saib xyuas, H.-CK thiab D.-SJ; qhov projectkev tswj hwm, H.-CK thiab D.-SJ; Kev nrhiav nyiaj txiag, S.-HJ, H.-CK thiab D.-SJ Txhua tus kws sau ntawv muajnyeem thiab pom zoo rau cov ntawv luam tawm ntawm cov ntawv sau.

Kev tsis sib haum xeeb ntawm kev txaus siab:Cov kws sau ntawv tshaj tawm tsis muaj kev sib cav txog kev txaus siab.

Cov ntaub ntawv

1. Xie, C.; Xie, Z.; Xu, X.; Yang, D. Persimmon (Diospyros kakiL.) nplooj: Kev tshuaj xyuas txog kev siv ib txwm siv, phytochemistry thiab pharmacological zog.J. Ethnopharmacol.2015, 163, 229–240. [CrossRef]

2. Bei, W.; Zang, L.; Guo, J.; Peng, W.; Xu, A.; Nyob zoo, DA; Hu, Y.; Wu, W.; Hu, D.; Zhu, X. Neuroprotective teebmeem ntawm tus qauv flavonoid extract los ntawmDiospyros kakinplooj.J. Ethnopharmacol.2009, 126, 134–142. [CrossRef] [PubMed]

3. Sakanaka, S.; Tachibana, Y.; Okada, Y. Kev npaj thiab antioxidant zog ntawm extracts ntawm Japanese persimmon nplooj tshuaj yej (kakinoha-cha).Khoom noj khoom haus Chem.2005, 89, 569–575. [CrossRef] 4. Sa, YS; Kim, S.J.; Choi, H.-S. Lub anticoagulant feem ntawm nplooj ntawmDiospyros kakiL. muaj cov tshuaj tiv thaiv kab mob.Arch. Pharmacy Res.2005, 28, 667–67

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