Enzymatic synthesis of quercetin oleate esters using Candida antarctica lipase B
Objectives To investigate the lipase-catalyzed acylation of quercetin with oleic acid using Candida antarctica lipase B. Results Three acylated analogues were produced: quercetin 4′-oleate ($ C_{33} %$ H_{42} %$ O_{8} $), quercetin 3′,4′-dioleate ($ C_{51} %$ H_{74} %$ O_{9} $) and quercetin 7,3′,4′...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Saik, Amy Yi Hsan [verfasserIn] Lim, Yau Yan [verfasserIn] Stanslas, Johnson [verfasserIn] Choo, Wee Sim [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2016 |
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| Schlagwörter: |
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| Übergeordnetes Werk: |
Enthalten in: Biotechnology letters - Dordrecht [u.a.] : Springer Science + Business Media B.V, 1979, 39(2016), 2 vom: 03. Nov., Seite 297-304 |
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| Übergeordnetes Werk: |
volume:39 ; year:2016 ; number:2 ; day:03 ; month:11 ; pages:297-304 |
| Links: |
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| DOI / URN: |
10.1007/s10529-016-2246-5 |
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| Katalog-ID: |
SPR010866779 |
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| 100 | 1 | |a Saik, Amy Yi Hsan |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Enzymatic synthesis of quercetin oleate esters using Candida antarctica lipase B |
| 264 | 1 | |c 2016 | |
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| 520 | |a Objectives To investigate the lipase-catalyzed acylation of quercetin with oleic acid using Candida antarctica lipase B. Results Three acylated analogues were produced: quercetin 4′-oleate ($ C_{33} %$ H_{42} %$ O_{8} $), quercetin 3′,4′-dioleate ($ C_{51} %$ H_{74} %$ O_{9} $) and quercetin 7,3′,4′-trioleate ($ C_{69} %$ H_{106} %$ O_{10} $). Their identities were confirmed with UPLC–ESI–MS and 1H NMR analyses. The effects of temperature, duration and molar ratio of substrates on the bioconversion yields varied across conditions. The regioselectivity of the acylated quercetin analogues was affected by the molar ratio of substrates. TLC showed the acylated analogues had higher lipophilicity (152% increase) compared to quercetin. Partition coefficient (log P) of quercetin 4′-oleate was higher than those of quercetin and oleic acid. Quercetin 4′-oleate was also stable over 28 days of storage. Conclusions Quercetin oleate esters with enhanced lipophilicity can be produced via lipase-catalyzed reaction using C. antarctica lipase B to be used in topical applications. | ||
| 650 | 4 | |a Acylated quercetin |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Lipase |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Oleic acid |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Quercetin |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Quercetin 4′-oleate |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Regioselectivity |7 (dpeaa)DE-He213 | |
| 700 | 1 | |a Lim, Yau Yan |e verfasserin |4 aut | |
| 700 | 1 | |a Stanslas, Johnson |e verfasserin |4 aut | |
| 700 | 1 | |a Choo, Wee Sim |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Biotechnology letters |d Dordrecht [u.a.] : Springer Science + Business Media B.V, 1979 |g 39(2016), 2 vom: 03. Nov., Seite 297-304 |w (DE-627)312808356 |w (DE-600)2012203-2 |x 1573-6776 |7 nnns |
| 773 | 1 | 8 | |g volume:39 |g year:2016 |g number:2 |g day:03 |g month:11 |g pages:297-304 |
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| allfields |
10.1007/s10529-016-2246-5 doi (DE-627)SPR010866779 (SPR)s10529-016-2246-5-e DE-627 ger DE-627 rakwb eng 660 ASE 42.30 bkl 58.30 bkl Saik, Amy Yi Hsan verfasserin aut Enzymatic synthesis of quercetin oleate esters using Candida antarctica lipase B 2016 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Objectives To investigate the lipase-catalyzed acylation of quercetin with oleic acid using Candida antarctica lipase B. Results Three acylated analogues were produced: quercetin 4′-oleate ($ C_{33} %$ H_{42} %$ O_{8} $), quercetin 3′,4′-dioleate ($ C_{51} %$ H_{74} %$ O_{9} $) and quercetin 7,3′,4′-trioleate ($ C_{69} %$ H_{106} %$ O_{10} $). Their identities were confirmed with UPLC–ESI–MS and 1H NMR analyses. The effects of temperature, duration and molar ratio of substrates on the bioconversion yields varied across conditions. The regioselectivity of the acylated quercetin analogues was affected by the molar ratio of substrates. TLC showed the acylated analogues had higher lipophilicity (152% increase) compared to quercetin. Partition coefficient (log P) of quercetin 4′-oleate was higher than those of quercetin and oleic acid. Quercetin 4′-oleate was also stable over 28 days of storage. Conclusions Quercetin oleate esters with enhanced lipophilicity can be produced via lipase-catalyzed reaction using C. antarctica lipase B to be used in topical applications. Acylated quercetin (dpeaa)DE-He213 Lipase (dpeaa)DE-He213 Oleic acid (dpeaa)DE-He213 Quercetin (dpeaa)DE-He213 Quercetin 4′-oleate (dpeaa)DE-He213 Regioselectivity (dpeaa)DE-He213 Lim, Yau Yan verfasserin aut Stanslas, Johnson verfasserin aut Choo, Wee Sim verfasserin aut Enthalten in Biotechnology letters Dordrecht [u.a.] : Springer Science + Business Media B.V, 1979 39(2016), 2 vom: 03. Nov., Seite 297-304 (DE-627)312808356 (DE-600)2012203-2 1573-6776 nnns volume:39 year:2016 number:2 day:03 month:11 pages:297-304 https://dx.doi.org/10.1007/s10529-016-2246-5 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 42.30 ASE 58.30 ASE AR 39 2016 2 03 11 297-304 |
| spelling |
10.1007/s10529-016-2246-5 doi (DE-627)SPR010866779 (SPR)s10529-016-2246-5-e DE-627 ger DE-627 rakwb eng 660 ASE 42.30 bkl 58.30 bkl Saik, Amy Yi Hsan verfasserin aut Enzymatic synthesis of quercetin oleate esters using Candida antarctica lipase B 2016 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Objectives To investigate the lipase-catalyzed acylation of quercetin with oleic acid using Candida antarctica lipase B. Results Three acylated analogues were produced: quercetin 4′-oleate ($ C_{33} %$ H_{42} %$ O_{8} $), quercetin 3′,4′-dioleate ($ C_{51} %$ H_{74} %$ O_{9} $) and quercetin 7,3′,4′-trioleate ($ C_{69} %$ H_{106} %$ O_{10} $). Their identities were confirmed with UPLC–ESI–MS and 1H NMR analyses. The effects of temperature, duration and molar ratio of substrates on the bioconversion yields varied across conditions. The regioselectivity of the acylated quercetin analogues was affected by the molar ratio of substrates. TLC showed the acylated analogues had higher lipophilicity (152% increase) compared to quercetin. Partition coefficient (log P) of quercetin 4′-oleate was higher than those of quercetin and oleic acid. Quercetin 4′-oleate was also stable over 28 days of storage. Conclusions Quercetin oleate esters with enhanced lipophilicity can be produced via lipase-catalyzed reaction using C. antarctica lipase B to be used in topical applications. Acylated quercetin (dpeaa)DE-He213 Lipase (dpeaa)DE-He213 Oleic acid (dpeaa)DE-He213 Quercetin (dpeaa)DE-He213 Quercetin 4′-oleate (dpeaa)DE-He213 Regioselectivity (dpeaa)DE-He213 Lim, Yau Yan verfasserin aut Stanslas, Johnson verfasserin aut Choo, Wee Sim verfasserin aut Enthalten in Biotechnology letters Dordrecht [u.a.] : Springer Science + Business Media B.V, 1979 39(2016), 2 vom: 03. Nov., Seite 297-304 (DE-627)312808356 (DE-600)2012203-2 1573-6776 nnns volume:39 year:2016 number:2 day:03 month:11 pages:297-304 https://dx.doi.org/10.1007/s10529-016-2246-5 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 42.30 ASE 58.30 ASE AR 39 2016 2 03 11 297-304 |
| allfields_unstemmed |
10.1007/s10529-016-2246-5 doi (DE-627)SPR010866779 (SPR)s10529-016-2246-5-e DE-627 ger DE-627 rakwb eng 660 ASE 42.30 bkl 58.30 bkl Saik, Amy Yi Hsan verfasserin aut Enzymatic synthesis of quercetin oleate esters using Candida antarctica lipase B 2016 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Objectives To investigate the lipase-catalyzed acylation of quercetin with oleic acid using Candida antarctica lipase B. Results Three acylated analogues were produced: quercetin 4′-oleate ($ C_{33} %$ H_{42} %$ O_{8} $), quercetin 3′,4′-dioleate ($ C_{51} %$ H_{74} %$ O_{9} $) and quercetin 7,3′,4′-trioleate ($ C_{69} %$ H_{106} %$ O_{10} $). Their identities were confirmed with UPLC–ESI–MS and 1H NMR analyses. The effects of temperature, duration and molar ratio of substrates on the bioconversion yields varied across conditions. The regioselectivity of the acylated quercetin analogues was affected by the molar ratio of substrates. TLC showed the acylated analogues had higher lipophilicity (152% increase) compared to quercetin. Partition coefficient (log P) of quercetin 4′-oleate was higher than those of quercetin and oleic acid. Quercetin 4′-oleate was also stable over 28 days of storage. Conclusions Quercetin oleate esters with enhanced lipophilicity can be produced via lipase-catalyzed reaction using C. antarctica lipase B to be used in topical applications. Acylated quercetin (dpeaa)DE-He213 Lipase (dpeaa)DE-He213 Oleic acid (dpeaa)DE-He213 Quercetin (dpeaa)DE-He213 Quercetin 4′-oleate (dpeaa)DE-He213 Regioselectivity (dpeaa)DE-He213 Lim, Yau Yan verfasserin aut Stanslas, Johnson verfasserin aut Choo, Wee Sim verfasserin aut Enthalten in Biotechnology letters Dordrecht [u.a.] : Springer Science + Business Media B.V, 1979 39(2016), 2 vom: 03. Nov., Seite 297-304 (DE-627)312808356 (DE-600)2012203-2 1573-6776 nnns volume:39 year:2016 number:2 day:03 month:11 pages:297-304 https://dx.doi.org/10.1007/s10529-016-2246-5 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 42.30 ASE 58.30 ASE AR 39 2016 2 03 11 297-304 |
| allfieldsGer |
10.1007/s10529-016-2246-5 doi (DE-627)SPR010866779 (SPR)s10529-016-2246-5-e DE-627 ger DE-627 rakwb eng 660 ASE 42.30 bkl 58.30 bkl Saik, Amy Yi Hsan verfasserin aut Enzymatic synthesis of quercetin oleate esters using Candida antarctica lipase B 2016 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Objectives To investigate the lipase-catalyzed acylation of quercetin with oleic acid using Candida antarctica lipase B. Results Three acylated analogues were produced: quercetin 4′-oleate ($ C_{33} %$ H_{42} %$ O_{8} $), quercetin 3′,4′-dioleate ($ C_{51} %$ H_{74} %$ O_{9} $) and quercetin 7,3′,4′-trioleate ($ C_{69} %$ H_{106} %$ O_{10} $). Their identities were confirmed with UPLC–ESI–MS and 1H NMR analyses. The effects of temperature, duration and molar ratio of substrates on the bioconversion yields varied across conditions. The regioselectivity of the acylated quercetin analogues was affected by the molar ratio of substrates. TLC showed the acylated analogues had higher lipophilicity (152% increase) compared to quercetin. Partition coefficient (log P) of quercetin 4′-oleate was higher than those of quercetin and oleic acid. Quercetin 4′-oleate was also stable over 28 days of storage. Conclusions Quercetin oleate esters with enhanced lipophilicity can be produced via lipase-catalyzed reaction using C. antarctica lipase B to be used in topical applications. Acylated quercetin (dpeaa)DE-He213 Lipase (dpeaa)DE-He213 Oleic acid (dpeaa)DE-He213 Quercetin (dpeaa)DE-He213 Quercetin 4′-oleate (dpeaa)DE-He213 Regioselectivity (dpeaa)DE-He213 Lim, Yau Yan verfasserin aut Stanslas, Johnson verfasserin aut Choo, Wee Sim verfasserin aut Enthalten in Biotechnology letters Dordrecht [u.a.] : Springer Science + Business Media B.V, 1979 39(2016), 2 vom: 03. Nov., Seite 297-304 (DE-627)312808356 (DE-600)2012203-2 1573-6776 nnns volume:39 year:2016 number:2 day:03 month:11 pages:297-304 https://dx.doi.org/10.1007/s10529-016-2246-5 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 42.30 ASE 58.30 ASE AR 39 2016 2 03 11 297-304 |
| allfieldsSound |
10.1007/s10529-016-2246-5 doi (DE-627)SPR010866779 (SPR)s10529-016-2246-5-e DE-627 ger DE-627 rakwb eng 660 ASE 42.30 bkl 58.30 bkl Saik, Amy Yi Hsan verfasserin aut Enzymatic synthesis of quercetin oleate esters using Candida antarctica lipase B 2016 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Objectives To investigate the lipase-catalyzed acylation of quercetin with oleic acid using Candida antarctica lipase B. Results Three acylated analogues were produced: quercetin 4′-oleate ($ C_{33} %$ H_{42} %$ O_{8} $), quercetin 3′,4′-dioleate ($ C_{51} %$ H_{74} %$ O_{9} $) and quercetin 7,3′,4′-trioleate ($ C_{69} %$ H_{106} %$ O_{10} $). Their identities were confirmed with UPLC–ESI–MS and 1H NMR analyses. The effects of temperature, duration and molar ratio of substrates on the bioconversion yields varied across conditions. The regioselectivity of the acylated quercetin analogues was affected by the molar ratio of substrates. TLC showed the acylated analogues had higher lipophilicity (152% increase) compared to quercetin. Partition coefficient (log P) of quercetin 4′-oleate was higher than those of quercetin and oleic acid. Quercetin 4′-oleate was also stable over 28 days of storage. Conclusions Quercetin oleate esters with enhanced lipophilicity can be produced via lipase-catalyzed reaction using C. antarctica lipase B to be used in topical applications. Acylated quercetin (dpeaa)DE-He213 Lipase (dpeaa)DE-He213 Oleic acid (dpeaa)DE-He213 Quercetin (dpeaa)DE-He213 Quercetin 4′-oleate (dpeaa)DE-He213 Regioselectivity (dpeaa)DE-He213 Lim, Yau Yan verfasserin aut Stanslas, Johnson verfasserin aut Choo, Wee Sim verfasserin aut Enthalten in Biotechnology letters Dordrecht [u.a.] : Springer Science + Business Media B.V, 1979 39(2016), 2 vom: 03. Nov., Seite 297-304 (DE-627)312808356 (DE-600)2012203-2 1573-6776 nnns volume:39 year:2016 number:2 day:03 month:11 pages:297-304 https://dx.doi.org/10.1007/s10529-016-2246-5 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 42.30 ASE 58.30 ASE AR 39 2016 2 03 11 297-304 |
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English |
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Enthalten in Biotechnology letters 39(2016), 2 vom: 03. Nov., Seite 297-304 volume:39 year:2016 number:2 day:03 month:11 pages:297-304 |
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Acylated quercetin Lipase Oleic acid Quercetin Quercetin 4′-oleate Regioselectivity |
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Biotechnology letters |
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Saik, Amy Yi Hsan @@aut@@ Lim, Yau Yan @@aut@@ Stanslas, Johnson @@aut@@ Choo, Wee Sim @@aut@@ |
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2016-11-03T00:00:00Z |
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Results Three acylated analogues were produced: quercetin 4′-oleate ($ C_{33} %$ H_{42} %$ O_{8} $), quercetin 3′,4′-dioleate ($ C_{51} %$ H_{74} %$ O_{9} $) and quercetin 7,3′,4′-trioleate ($ C_{69} %$ H_{106} %$ O_{10} $). Their identities were confirmed with UPLC–ESI–MS and 1H NMR analyses. The effects of temperature, duration and molar ratio of substrates on the bioconversion yields varied across conditions. The regioselectivity of the acylated quercetin analogues was affected by the molar ratio of substrates. TLC showed the acylated analogues had higher lipophilicity (152% increase) compared to quercetin. Partition coefficient (log P) of quercetin 4′-oleate was higher than those of quercetin and oleic acid. Quercetin 4′-oleate was also stable over 28 days of storage. 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|
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Saik, Amy Yi Hsan |
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Saik, Amy Yi Hsan ddc 660 bkl 42.30 bkl 58.30 misc Acylated quercetin misc Lipase misc Oleic acid misc Quercetin misc Quercetin 4′-oleate misc Regioselectivity Enzymatic synthesis of quercetin oleate esters using Candida antarctica lipase B |
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660 ASE 42.30 bkl 58.30 bkl Enzymatic synthesis of quercetin oleate esters using Candida antarctica lipase B Acylated quercetin (dpeaa)DE-He213 Lipase (dpeaa)DE-He213 Oleic acid (dpeaa)DE-He213 Quercetin (dpeaa)DE-He213 Quercetin 4′-oleate (dpeaa)DE-He213 Regioselectivity (dpeaa)DE-He213 |
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ddc 660 bkl 42.30 bkl 58.30 misc Acylated quercetin misc Lipase misc Oleic acid misc Quercetin misc Quercetin 4′-oleate misc Regioselectivity |
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ddc 660 bkl 42.30 bkl 58.30 misc Acylated quercetin misc Lipase misc Oleic acid misc Quercetin misc Quercetin 4′-oleate misc Regioselectivity |
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ddc 660 bkl 42.30 bkl 58.30 misc Acylated quercetin misc Lipase misc Oleic acid misc Quercetin misc Quercetin 4′-oleate misc Regioselectivity |
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Saik, Amy Yi Hsan Lim, Yau Yan Stanslas, Johnson Choo, Wee Sim |
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enzymatic synthesis of quercetin oleate esters using candida antarctica lipase b |
| title_auth |
Enzymatic synthesis of quercetin oleate esters using Candida antarctica lipase B |
| abstract |
Objectives To investigate the lipase-catalyzed acylation of quercetin with oleic acid using Candida antarctica lipase B. Results Three acylated analogues were produced: quercetin 4′-oleate ($ C_{33} %$ H_{42} %$ O_{8} $), quercetin 3′,4′-dioleate ($ C_{51} %$ H_{74} %$ O_{9} $) and quercetin 7,3′,4′-trioleate ($ C_{69} %$ H_{106} %$ O_{10} $). Their identities were confirmed with UPLC–ESI–MS and 1H NMR analyses. The effects of temperature, duration and molar ratio of substrates on the bioconversion yields varied across conditions. The regioselectivity of the acylated quercetin analogues was affected by the molar ratio of substrates. TLC showed the acylated analogues had higher lipophilicity (152% increase) compared to quercetin. Partition coefficient (log P) of quercetin 4′-oleate was higher than those of quercetin and oleic acid. Quercetin 4′-oleate was also stable over 28 days of storage. Conclusions Quercetin oleate esters with enhanced lipophilicity can be produced via lipase-catalyzed reaction using C. antarctica lipase B to be used in topical applications. |
| abstractGer |
Objectives To investigate the lipase-catalyzed acylation of quercetin with oleic acid using Candida antarctica lipase B. Results Three acylated analogues were produced: quercetin 4′-oleate ($ C_{33} %$ H_{42} %$ O_{8} $), quercetin 3′,4′-dioleate ($ C_{51} %$ H_{74} %$ O_{9} $) and quercetin 7,3′,4′-trioleate ($ C_{69} %$ H_{106} %$ O_{10} $). Their identities were confirmed with UPLC–ESI–MS and 1H NMR analyses. The effects of temperature, duration and molar ratio of substrates on the bioconversion yields varied across conditions. The regioselectivity of the acylated quercetin analogues was affected by the molar ratio of substrates. TLC showed the acylated analogues had higher lipophilicity (152% increase) compared to quercetin. Partition coefficient (log P) of quercetin 4′-oleate was higher than those of quercetin and oleic acid. Quercetin 4′-oleate was also stable over 28 days of storage. Conclusions Quercetin oleate esters with enhanced lipophilicity can be produced via lipase-catalyzed reaction using C. antarctica lipase B to be used in topical applications. |
| abstract_unstemmed |
Objectives To investigate the lipase-catalyzed acylation of quercetin with oleic acid using Candida antarctica lipase B. Results Three acylated analogues were produced: quercetin 4′-oleate ($ C_{33} %$ H_{42} %$ O_{8} $), quercetin 3′,4′-dioleate ($ C_{51} %$ H_{74} %$ O_{9} $) and quercetin 7,3′,4′-trioleate ($ C_{69} %$ H_{106} %$ O_{10} $). Their identities were confirmed with UPLC–ESI–MS and 1H NMR analyses. The effects of temperature, duration and molar ratio of substrates on the bioconversion yields varied across conditions. The regioselectivity of the acylated quercetin analogues was affected by the molar ratio of substrates. TLC showed the acylated analogues had higher lipophilicity (152% increase) compared to quercetin. Partition coefficient (log P) of quercetin 4′-oleate was higher than those of quercetin and oleic acid. Quercetin 4′-oleate was also stable over 28 days of storage. Conclusions Quercetin oleate esters with enhanced lipophilicity can be produced via lipase-catalyzed reaction using C. antarctica lipase B to be used in topical applications. |
| collection_details |
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Enzymatic synthesis of quercetin oleate esters using Candida antarctica lipase B |
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https://dx.doi.org/10.1007/s10529-016-2246-5 |
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Lim, Yau Yan Stanslas, Johnson Choo, Wee Sim |
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2024-07-03T18:48:56.378Z |
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| score |
7.3996487 |