Lipase-catalyzed preparation of mono- and diesters of ferulic acid

Article abstract of DOI:10.3109/10242422.2015.1060228

Lipophilic and stable derivatives of ferulic acid are required to improve its efficacy in fatty foods and to optimize its use in cosmetic and pharmaceutical preparations. We report an improved synthesis of ferulic acid monoesters (ethyl ferulate and lauryl ferulate) using immobilized lipase from Candida antarctica B (CALB) in diisopropyl ether (DIPE). Maximum yields were 89% and 85% in 200 h for ethyl and lauryl ferulate, respectively. Ethyl ferulate was further acylated with vinyl esters to form ferulate diesters. 4-Acetoxy-ethyl ferulate was obtained with the immobilized lipase from Alcaligenes sp. (QLG) with 59% yield in 72 h, whereas 4-dodecanoyloxy-ethyl ferulate (a new compound) was synthesized with 52% yield in 72 h using CALB. DIPE was the best solvent for the transesterifications. Finally, the anti-inflammatory activity of the synthesized derivatives was evaluated in vitro; the compounds bearing a dodecyl chain showed improved anti-inflammatory activity compared with short-chain esters.

Full text of DOI:10.3109/10242422.2015.1060228

Biocatalysis and Biotransformation, 2015; eꢄꢉꢂy oꢅꢂꢀꢅꢈ: 1–9
ORIGINAL ARTICLE
Lipase-catalyzed preparation of mono- and diesters of ferulic acid
1
,3
2
2
GeorGina Sandoval , Paula G. Quintana , alicia BaldeSSari ,
1
1
antonio o. BalleSteroS & FranciSco J. Plou
1
2
Institute of Catalysis, CSIC, Madrid, Spain, Laboratory of Biocatalysis, Department
of Organic Chemistry and UMYMFOR, Faculty of Excat and Natural Sciences, University of Buenos Aires,
3
Buenos Aires, Argentina and CIATEJ, Guadalajara, Jal, Mexico
Abstract
lꢀpꢁphꢀꢂꢀꢃ ꢄꢅꢆ sꢇꢄbꢂꢈ ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs ꢁf fꢈꢉꢋꢂꢀꢃ ꢄꢃꢀꢆ ꢄꢉꢈ ꢉꢈqꢋꢀꢉꢈꢆ ꢇꢁ ꢀmpꢉꢁꢊꢈ ꢀꢇs ꢈffiꢃꢄꢃy ꢀꢅ fꢄꢇꢇy fꢁꢁꢆs ꢄꢅꢆ ꢇꢁ ꢁpꢇꢀmꢀzꢈ ꢀꢇs ꢋsꢈ
ꢀ
ꢅ ꢃꢁsmꢈꢇꢀꢃ ꢄꢅꢆ phꢄꢉmꢄꢃꢈꢋꢇꢀꢃꢄꢂ pꢉꢈpꢄꢉꢄꢇꢀꢁꢅs. Wꢈ ꢉꢈpꢁꢉꢇ ꢄꢅ ꢀmpꢉꢁꢊꢈꢆ syꢅꢇhꢈsꢀs ꢁf fꢈꢉꢋꢂꢀꢃ ꢄꢃꢀꢆ mꢁꢅꢁꢈsꢇꢈꢉs (ꢈꢇhyꢂ fꢈꢉꢋꢂꢄꢇꢈ
ꢄꢅꢆ ꢂꢄꢋꢉyꢂ fꢈꢉꢋꢂꢄꢇꢈ) ꢋsꢀꢅg ꢀmmꢁbꢀꢂꢀzꢈꢆ ꢂꢀpꢄsꢈ fꢉꢁm Candida antarctica B (calB) ꢀꢅ ꢆꢀꢀsꢁpꢉꢁpyꢂ ꢈꢇhꢈꢉ (diPe). Mꢄxꢀmꢋm
yꢀꢈꢂꢆs wꢈꢉꢈ 89% ꢄꢅꢆ 85% ꢀꢅ 200 h fꢁꢉ ꢈꢇhyꢂ ꢄꢅꢆ ꢂꢄꢋꢉyꢂ fꢈꢉꢋꢂꢄꢇꢈ, ꢉꢈspꢈꢃꢇꢀꢊꢈꢂy. eꢇhyꢂ fꢈꢉꢋꢂꢄꢇꢈ wꢄs fꢋꢉꢇhꢈꢉ ꢄꢃyꢂꢄꢇꢈꢆ wꢀꢇh ꢊꢀꢅyꢂ
ꢈsꢇꢈꢉs ꢇꢁ fꢁꢉm fꢈꢉꢋꢂꢄꢇꢈ ꢆꢀꢈsꢇꢈꢉs. 4-aꢃꢈꢇꢁxy-ꢈꢇhyꢂ fꢈꢉꢋꢂꢄꢇꢈ wꢄs ꢁbꢇꢄꢀꢅꢈꢆ wꢀꢇh ꢇhꢈ ꢀmmꢁbꢀꢂꢀzꢈꢆ ꢂꢀpꢄsꢈ fꢉꢁm Alcaligenes sp.
(
QlG) wꢀꢇh 59% yꢀꢈꢂꢆ ꢀꢅ 72 h, whꢈꢉꢈꢄs 4-ꢆꢁꢆꢈꢃꢄꢅꢁyꢂꢁxy-ꢈꢇhyꢂ fꢈꢉꢋꢂꢄꢇꢈ (ꢄ ꢅꢈw ꢃꢁmpꢁꢋꢅꢆ) wꢄs syꢅꢇhꢈsꢀzꢈꢆ wꢀꢇh
5
2% yꢀꢈꢂꢆ ꢀꢅ 72 h ꢋsꢀꢅg calB. diPe wꢄs ꢇhꢈ bꢈsꢇ sꢁꢂꢊꢈꢅꢇ fꢁꢉ ꢇhꢈ ꢇꢉꢄꢅsꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅs. Fꢀꢅꢄꢂꢂy, ꢇhꢈ ꢄꢅꢇꢀ-ꢀꢅflꢄmmꢄꢇꢁꢉy
ꢄꢃꢇꢀꢊꢀꢇy ꢁf ꢇhꢈ syꢅꢇhꢈsꢀzꢈꢆ ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs wꢄs ꢈꢊꢄꢂꢋꢄꢇꢈꢆ in vitro; ꢇhꢈ ꢃꢁmpꢁꢋꢅꢆs bꢈꢄꢉꢀꢅg ꢄ ꢆꢁꢆꢈꢃyꢂ ꢃhꢄꢀꢅ shꢁwꢈꢆ ꢀmpꢉꢁꢊꢈꢆ
ꢄꢅꢇꢀ-ꢀꢅflꢄmmꢄꢇꢁꢉy ꢄꢃꢇꢀꢊꢀꢇy ꢃꢁmpꢄꢉꢈꢆ wꢀꢇh shꢁꢉꢇ-ꢃhꢄꢀꢅ ꢈsꢇꢈꢉs.
Keywords: Ethyl ferulate, ferulic acid, food antioxidants, hydroxycinnamic acids, lipases, transesterification
Introduction
lꢀpꢁphꢀꢂꢀꢃ fꢈꢉꢋꢂꢄꢇꢈs ꢄꢂsꢁ hꢄꢊꢈ gꢉꢈꢄꢇ pꢁꢇꢈꢅꢇꢀꢄꢂ fꢁꢉ ꢋsꢈ
Fꢈꢉꢋꢂꢀꢃ ꢄꢃꢀꢆ (4-hyꢆꢉꢁxy-3-mꢈꢇhꢁxyꢃꢀꢅꢅꢄmꢀꢃ ꢄꢃꢀꢆ,
Fa, 1) ꢀs ꢄ ꢆꢀꢈꢇꢄꢉy ꢄꢅꢇꢀꢁxꢀꢆꢄꢅꢇ fꢁꢋꢅꢆ ꢀꢅ ꢇhꢈ ꢃꢈꢂꢂ wꢄꢂꢂs
ꢄs uv-bꢂꢁꢃkꢀꢅg ꢄgꢈꢅꢇs ꢀꢅ wꢄꢇꢈꢉpꢉꢁꢁf sꢋꢅsꢃꢉꢈꢈꢅs
(cꢁmpꢇꢁꢅ ꢈꢇ ꢄꢂ. 2000). eꢇhyꢂ fꢈꢉꢋꢂꢄꢇꢈ (eF, 2) ꢀs
ꢄmꢁꢅg ꢇhꢈ mꢁsꢇ sꢇꢋꢆꢀꢈꢆ ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs, bꢈꢃꢄꢋsꢈ ꢀꢇ ꢃꢄꢅ
bꢈ ꢋsꢈꢆ ꢄs ꢄ syꢅꢇhꢁꢅ fꢁꢉ ꢇhꢈ pꢉꢈpꢄꢉꢄꢇꢀꢁꢅ ꢁf ꢁꢇhꢈꢉ Fa
ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs. iꢅ ꢄꢆꢆꢀꢇꢀꢁꢅ, eF ꢀs ꢄ pꢉꢁmꢀsꢀꢅg ꢅꢈꢋꢉꢁpꢉꢁ-
ꢇꢈꢃꢇꢁꢉ ꢄgꢈꢅꢇ (Jꢁshꢀ ꢈꢇ ꢄꢂ. 2006; Sꢋꢂꢇꢄꢅꢄ 2012),
pꢁssꢈssꢈs ꢄꢅꢇꢀ-pꢂꢄꢇꢈꢂꢈꢇ ꢄggꢉꢈgꢄꢇꢀꢁꢅ pꢉꢁpꢈꢉꢇꢀꢈs (lꢀ
ꢈꢇ ꢄꢂ. 2009ꢄ), ꢄꢅꢆ hꢄs gꢉꢈꢄꢇ pꢁꢇꢈꢅꢇꢀꢄꢂ ꢄs ꢄꢅ ꢀꢅgꢉꢈꢆꢀꢈꢅꢇ
ꢀꢅ fꢁꢁꢆs ꢄꢅꢆ ꢃꢁsmꢈꢇꢀꢃs (chꢁqꢋꢈꢅꢈꢇ ꢈꢇ ꢄꢂ. 2008;
Sꢁꢋꢇꢁ ꢈꢇ ꢄꢂ. 2005). lꢄꢋꢉyꢂ fꢈꢉꢋꢂꢄꢇꢈ (lF, 3) ꢆꢀspꢂꢄys
hꢀgh hyꢆꢉꢁphꢁbꢀꢃꢀꢇy (ꢂꢁg P 6.97) whꢀꢃh mꢄkꢈs ꢀꢇ ꢊꢈꢉy
sꢋꢀꢇꢄbꢂꢈ ꢄs ꢄ ꢃꢁsmꢈꢇꢀꢃ ꢀꢅgꢉꢈꢆꢀꢈꢅꢇ (vꢁꢀsꢀꢅ-chꢀꢉꢈꢇ ꢈꢇ ꢄꢂ.
2007). Mꢁꢉꢈꢁꢊꢈꢉ, lF ꢆꢀspꢂꢄys ꢀꢅꢇꢈꢉꢈsꢇꢀꢅg bꢀꢁꢂꢁgꢀꢃꢄꢂ
pꢉꢁpꢈꢉꢇꢀꢈs, fꢁꢉ ꢈxꢄmpꢂꢈ ꢄꢅꢇꢀꢇꢋmꢁꢉ.
ꢁ
f mꢄꢅy pꢂꢄꢅꢇs (Bꢄꢉbꢈꢉꢁꢋssꢈ ꢈꢇ ꢄꢂ. 2008). thꢈꢉꢈ ꢀs
gꢉꢁwꢀꢅg ꢀꢅꢇꢈꢉꢈsꢇ ꢀꢅ ꢋsꢀꢅg Fa ꢄs ꢄ bꢀꢁꢄꢃꢇꢀꢊꢈ ꢀꢅgꢉꢈꢆꢀꢈꢅꢇ
ꢅ fꢋꢅꢃꢇꢀꢁꢅꢄꢂ fꢁꢁꢆs, ꢅꢋꢇꢉꢄꢃꢈꢋꢇꢀꢃꢄꢂs, ꢄꢅꢆ phꢄꢉmꢄꢃꢈꢋ-
ꢇꢀꢃꢄꢂ ꢄꢅꢆ ꢃꢁsmꢈꢇꢀꢃ pꢉꢁꢆꢋꢃꢇs ꢆꢋꢈ ꢇꢁ ꢀꢇs ꢄbꢋꢅꢆꢄꢅꢃꢈ
ꢅ ꢄgꢉꢁ-ꢀꢅꢆꢋsꢇꢉꢀꢄꢂ wꢄsꢇꢈs ꢄꢅꢆ ꢇꢁ ꢀꢇs bꢀꢁꢂꢁgꢀꢃꢄꢂ
ꢀ
ꢀ
pꢉꢁpꢈꢉꢇꢀꢈs—ꢄs ꢄꢅꢇꢀꢁxꢀꢆꢄꢅꢇ, ꢄꢅꢇꢀmꢀꢃꢉꢁbꢀꢄꢂ, ꢄꢅꢇꢀꢊꢀꢉꢄꢂ,
ꢄꢅꢇꢀ-ꢀꢅflꢄmmꢄꢇꢁꢉy, ꢄꢅꢇꢀꢄꢂꢂꢈꢉgꢈꢅꢀꢃ, ꢄꢅꢆ ꢄꢅꢇꢀꢇꢋmꢁꢉ—-
ꢄꢅꢆ fꢁꢉ pꢉꢁꢇꢈꢃꢇꢀꢁꢅ ꢄgꢄꢀꢅsꢇ uva ꢉꢄꢆꢀꢄꢇꢀꢁꢅ (Sꢉꢀꢅꢀꢊꢄsꢄꢅ
ꢈꢇ ꢄꢂ. 2007; Zhꢄꢁ & Mꢁghꢄꢆꢄsꢀꢄꢅ 2008). Hꢁwꢈꢊꢈꢉ,
sꢈꢊꢈꢉꢄꢂ ꢂꢀmꢀꢇꢄꢇꢀꢁꢅs fꢁꢉ ꢀꢇs ꢀꢅꢆꢋsꢇꢉꢀꢄꢂ ꢄppꢂꢀꢃꢄꢇꢀꢁꢅ ꢄꢉꢀsꢈ
fꢉꢁm ꢀꢇs ꢂꢁw sꢁꢂꢋbꢀꢂꢀꢇy ꢀꢅ ꢁꢉgꢄꢅꢀꢃ mꢈꢆꢀꢄ ꢄꢅꢆ ꢀꢇs
ꢂꢀmꢀꢇꢈꢆ sꢇꢄbꢀꢂꢀꢇy ꢇꢁ ꢁxꢀꢆꢄꢇꢀꢁꢅ.
oꢅꢈ ꢄppꢉꢁꢄꢃh ꢇꢁ ꢁꢊꢈꢉꢃꢁmꢈ ꢇhꢀs ꢀs ꢇꢁ syꢅꢇhꢈsꢀzꢈ
mꢁꢉꢈ ꢂꢀpꢁphꢀꢂꢀꢃ ꢄꢅꢆ sꢇꢄbꢂꢈ Fa ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs. iꢅ fꢄꢇꢇy
fꢁꢁꢆs, ꢂꢀpꢁphꢀꢂꢀzꢄꢇꢀꢁꢅ ꢁf phꢈꢅꢁꢂꢀꢃ ꢄꢃꢀꢆs ꢃꢄꢅ mꢁꢆꢋꢂꢄꢇꢈ
ꢇhꢈꢀꢉ ꢂꢁꢃꢄꢂꢀzꢄꢇꢀꢁꢅ ꢀꢅ ꢈmꢋꢂsꢀꢁꢅs ꢄꢅꢆ, ꢄs ꢄ ꢃꢁꢅsꢈqꢋꢈꢅꢃꢈ,
ꢇhꢈꢀꢉ ꢄꢅꢇꢀꢁxꢀꢆꢄꢅꢇ ꢈffiꢃꢀꢈꢅꢃy (Sꢁꢉꢈꢅsꢈꢅ ꢈꢇ ꢄꢂ. 2014).
iꢅ ꢁꢉꢆꢈꢉ ꢇꢁ ꢁbꢇꢄꢀꢅ sꢋꢃh ꢂꢀpꢁphꢀꢂꢀꢃ ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs, ꢄ
bꢀꢁꢃꢄꢇꢄꢂyꢇꢀꢃ ꢄppꢉꢁꢄꢃh ꢀs pꢉꢈfꢈꢉꢉꢈꢆ ꢁꢊꢈꢉ ꢃꢂꢄssꢀꢃꢄꢂ
ꢃhꢈmꢀꢃꢄꢂ syꢅꢇhꢈsꢀs (Gꢁꢅzꢄꢂꢈz-Sꢄbꢀꢅ ꢈꢇ ꢄꢂ. 2011),
ꢈspꢈꢃꢀꢄꢂꢂy fꢁꢉ fꢁꢁꢆ ꢋsꢈ, sꢀꢅꢃꢈ phꢈꢅꢁꢂꢀꢃ ꢄꢃꢀꢆs ꢄꢉꢈ ꢊꢈꢉy
sꢈꢅsꢀꢇꢀꢊꢈ ꢇꢁ hꢄꢉsh ꢉꢈꢄꢃꢇꢀꢁꢅ ꢃꢁꢅꢆꢀꢇꢀꢁꢅs sꢋꢃh ꢄs hꢀgh
cꢁꢉꢉꢈspꢁꢅꢆꢀꢅg ꢄꢋꢇhꢁꢉ: Fꢉꢄꢅꢃꢀsꢃꢁ J. Pꢂꢁꢋ, dꢈpꢄꢉꢇꢄmꢈꢅꢇꢁ ꢆꢈ Bꢀꢁꢃꢄꢇáꢂꢀsꢀs, iꢅsꢇꢀꢇꢋꢇꢁ ꢆꢈ cꢄꢇáꢂꢀsꢀs y Pꢈꢇꢉꢁꢂꢈꢁqꢋímꢀꢃꢄ, cSic, cꢄꢅꢇꢁbꢂꢄꢅꢃꢁ, Mꢄꢉꢀꢈ cꢋꢉꢀꢈ 2, 28049
Mꢄꢆꢉꢀꢆ, Spꢄꢀꢅ. Fꢄx: 34 91 5854760. e-mꢄꢀꢂ: fpꢂꢁꢋ@ꢀꢃp.ꢃsꢀꢃ.ꢈs
(
Received 15 September 2014; revised 11 February 2015; accepted 05 June 2015)
iSSn 1024-2422 pꢉꢀꢅꢇ/iSSn 1029-2446 ꢁꢅꢂꢀꢅꢈ © 2015 iꢅfꢁꢉmꢄ uK, lꢇꢆ.
doi: 10.3109/10242422.2015.1060228

2
G. Sandoval et al.
ꢇꢈmpꢈꢉꢄꢇꢋꢉꢈs ꢄꢅꢆ ꢈxꢇꢉꢈmꢈ pH ꢊꢄꢂꢋꢈs (Mꢋꢅꢀꢅ &
eꢆwꢄꢉꢆs-lꢈꢊy 2011). thꢈ ꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢁꢉ ꢇꢉꢄꢅsꢈs-
ꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢁf Fa ꢃꢄꢇꢄꢂyzꢈꢆ by ꢂꢀpꢄsꢈs ꢀs ꢇhꢈ pꢉꢈfꢈꢉꢉꢈꢆ
ꢉꢁꢋꢇꢈ, ꢄs ꢂꢀpꢄsꢈs ꢄꢉꢈ ꢊꢈꢉsꢄꢇꢀꢂꢈ bꢀꢁꢃꢄꢇꢄꢂysꢇs wꢀꢇh ꢄ wꢀꢆꢈ
sꢋbsꢇꢉꢄꢇꢈ ꢄꢃꢃꢈpꢇꢄꢅꢃꢈ ꢄꢅꢆ ꢅꢁꢇꢄbꢂꢈ sꢇꢄbꢀꢂꢀꢇy ꢀꢅ sꢈꢊꢈꢉꢄꢂ
bꢀꢁꢃꢄꢇꢄꢂysꢇ wꢄs fiꢂꢇꢈꢉꢈꢆ ꢄꢅꢆ wꢄshꢈꢆ wꢀꢇh ꢇhꢈ ꢉꢈꢄꢃꢇꢀꢁꢅ
sꢁꢂꢊꢈꢅꢇ (35 ml) ꢇꢁ ꢈxꢇꢉꢄꢃꢇ ꢇhꢈ ꢄꢆsꢁꢉbꢈꢆ Fa ꢈsꢇꢈꢉs.
thꢈ sꢁꢂꢊꢈꢅꢇ wꢄs ꢇhꢈꢅ ꢉꢈmꢁꢊꢈꢆ ꢋꢅꢆꢈꢉ ꢉꢈꢆꢋꢃꢈꢆ pꢉꢈs-
sꢋꢉꢈ ꢄꢅꢆ ꢇhꢈ ꢃꢉꢋꢆꢈ ꢉꢈsꢀꢆꢋꢈ wꢄs pꢋꢉꢀfiꢈꢆ by ꢃꢁꢂꢋmꢅ
ꢃhꢉꢁmꢄꢇꢁgꢉꢄphy ꢁꢅ ꢄ ꢃꢁꢂꢋmꢅ (1.530 ꢃm) pꢄꢃkꢈꢆ
wꢀꢇh sꢀꢂꢀꢃꢄ gꢈꢂ 60 (230–400 mꢈsh, Mꢈꢉꢃk) ꢋsꢀꢅg
hꢈxꢄꢅꢈ:ꢈꢇhyꢂ ꢄꢃꢈꢇꢄꢇꢈ 8:2 (ꢊ/ꢊ) ꢄs ꢈꢂꢋꢈꢅꢇ.
ꢁꢉgꢄꢅꢀꢃ sꢁꢂꢊꢈꢅꢇs (cꢄsꢄs-Gꢁꢆꢁy ꢈꢇ ꢄꢂ. 2012; Fꢈꢉꢉꢈꢀꢉꢄ-
dꢀꢄs ꢈꢇ ꢄꢂ. 2013; Gꢄꢉꢃꢀꢄ-lꢀñꢄꢉꢈs ꢈꢇ ꢄꢂ. 2012).
Hꢁwꢈꢊꢈꢉ, ꢇhꢈ ꢉꢈpꢁꢉꢇꢈꢆ ꢃꢁꢅꢆꢀꢇꢀꢁꢅs ꢇꢁ ꢆꢈꢉꢀꢊꢄꢇꢀzꢈ Fa
ꢄꢉꢈ ꢅꢁꢇ ꢀꢅꢆꢋsꢇꢉꢀꢄꢂꢂy ꢈꢃꢁꢅꢁmꢀꢃ, ꢆꢋꢈ ꢇꢁ ꢇhꢈ ꢂꢁw ꢃꢁꢅꢊꢈꢉ-
sꢀꢁꢅ ꢁbꢇꢄꢀꢅꢈꢆ (cꢁmpꢇꢁꢅ ꢈꢇ ꢄꢂ. 2000; Kꢄꢇsꢁꢋꢉꢄ ꢈꢇ ꢄꢂ.
Enzymatic acylation of ethyl ferulate
2
009b), ꢇhꢈ pꢉꢁꢂꢁꢅgꢈꢆ ꢉꢈꢄꢃꢇꢀꢁꢅ ꢇꢀmꢈs, ꢄꢅꢆ ꢇhꢈ ꢂꢄꢉgꢈ
ꢄmꢁꢋꢅꢇs ꢁf bꢀꢁꢃꢄꢇꢄꢂysꢇ ꢅꢈꢈꢆꢈꢆ (Wꢈꢀꢇkꢄmp ꢈꢇ ꢄꢂ.
006).
iꢅ ꢇhꢀs wꢁꢉk, wꢈ hꢄꢊꢈ ꢇꢉꢀꢈꢆ ꢇꢁ ꢁpꢇꢀmꢀzꢈ ꢇhꢈ
tꢁ ꢄ sꢁꢂꢋꢇꢀꢁꢅ ꢁf eF (10 mg/ml, 44 mM) ꢀꢅ ꢇhꢈ
ꢀꢅꢆꢀꢃꢄꢇꢈꢆ sꢁꢂꢊꢈꢅꢇ, ꢇhꢈ ꢄꢃyꢂ ꢆꢁꢅꢁꢉ (ꢊꢀꢅyꢂ ꢄꢃꢈꢇꢄꢇꢈ ꢁꢉ
2
ꢊꢀꢅyꢂ ꢂꢄꢋꢉꢄꢇꢈ) ꢄꢅꢆ ꢇhꢈ ꢀmmꢁbꢀꢂꢀzꢈꢆ ꢂꢀpꢄsꢈ wꢈꢉꢈ ꢄꢆꢆꢈꢆ
ꢄꢇ ꢆꢀffꢈꢉꢈꢅꢇ ꢉꢄꢇꢀꢁs. thꢈ ꢇꢁꢇꢄꢂ ꢊꢁꢂꢋmꢈ wꢄs 1 ml. thꢈ
mꢀxꢇꢋꢉꢈs wꢈꢉꢈ ꢀꢅꢃꢋbꢄꢇꢈꢆ ꢄꢇ 60°c ꢀꢅ sꢈꢄꢂꢈꢆ 4-ml
ꢆꢄꢉk ꢊꢀꢄꢂs ꢄꢇ 250 ꢉpm wꢀꢇh ꢁꢉbꢀꢇꢄꢂ shꢄkꢀꢅg. aꢂꢀqꢋꢁꢇs
ꢈꢅzymꢄꢇꢀꢃ pꢉꢈpꢄꢉꢄꢇꢀꢁꢅ ꢁf Fa ꢈsꢇꢈꢉs by ꢄppꢉꢁpꢉꢀꢄꢇꢈ
sꢈꢂꢈꢃꢇꢀꢁꢅ ꢁf bꢀꢁꢃꢄꢇꢄꢂysꢇ, sꢁꢂꢊꢈꢅꢇ, ꢄꢅꢆ ꢁꢇhꢈꢉ ꢈxpꢈꢉꢀ-
mꢈꢅꢇꢄꢂ pꢄꢉꢄmꢈꢇꢈꢉs. thꢈ syꢅꢇhꢈsꢀzꢈꢆ mꢁꢅꢁꢈsꢇꢈꢉs
wꢈꢉꢈ fꢋꢉꢇhꢈꢉ ꢄꢃyꢂꢄꢇꢈꢆ wꢀꢇh ꢊꢀꢅyꢂ ꢈsꢇꢈꢉs ꢀꢅ ꢁꢉꢆꢈꢉ ꢇꢁ
(
ꢁ
2 ml) wꢈꢉꢈ wꢀꢇhꢆꢉꢄwꢅ ꢄꢇ ꢀꢅꢇꢈꢉꢊꢄꢂs ꢄꢅꢆ ꢇhꢈ pꢉꢁgꢉꢈss
f ꢇhꢈ ꢉꢈꢄꢃꢇꢀꢁꢅ wꢄs ꢄꢅꢄꢂyzꢈꢆ by tlc. Fꢁꢉ ꢇhꢈ qꢋꢄꢅ-
ꢁbꢇꢄꢀꢅ Fa ꢆꢀꢈsꢇꢈꢉs wꢀꢇh sꢀgꢅꢀfiꢃꢄꢅꢇꢂy ꢀꢅꢃꢉꢈꢄsꢈꢆ hyꢆꢉꢁ-
ꢇꢀfiꢃꢄꢇꢀꢁꢅ ꢁf Fa ꢈsꢇꢈꢉs, ꢇhꢈ ꢉꢈꢄꢃꢇꢀꢁꢅs wꢈꢉꢈ sꢇꢁppꢈꢆ by
fiꢂꢇꢈꢉꢀꢅg ꢇhꢈ mꢀxꢇꢋꢉꢈ wꢀꢇh ꢃꢈꢅꢇꢉꢀfꢋgꢈ ꢇꢋbꢈs ꢃꢁꢅꢇꢄꢀꢅꢀꢅg
ꢄ PvdF dꢋꢉꢄpꢁꢉꢈ 0.45-mm mꢈmbꢉꢄꢅꢈ ꢄꢅꢆ ꢇhꢈ
sꢋpꢈꢉꢅꢄꢇꢄꢅꢇs wꢈꢉꢈ ꢄꢅꢄꢂyzꢈꢆ by HPlc. iꢅ ꢁꢉꢆꢈꢉ ꢇꢁ
ꢃhꢈmꢀꢃꢄꢂꢂy ꢃhꢄꢉꢄꢃꢇꢈꢉꢀzꢈ ꢇhꢈ ꢉꢈꢄꢃꢇꢀꢁꢅ pꢉꢁꢆꢋꢃꢇs, ꢇhꢈ
ꢉꢈꢄꢃꢇꢀꢁꢅs wꢈꢉꢈ sꢃꢄꢂꢈꢆ-ꢋp ꢇꢁ 10 ml. thꢈ sꢁꢂꢀꢆ bꢀꢁ-
ꢃꢄꢇꢄꢂysꢇ wꢄs fiꢂꢇꢈꢉꢈꢆ ꢄꢅꢆ wꢄshꢈꢆ wꢀꢇh ꢇhꢈ ꢉꢈꢄꢃꢇꢀꢁꢅ
sꢁꢂꢊꢈꢅꢇ (35 ml) ꢇꢁ ꢈxꢇꢉꢄꢃꢇ ꢇhꢈ ꢄꢆsꢁꢉbꢈꢆ Fa
ꢆꢀꢈsꢇꢈꢉs. thꢈ sꢁꢂꢊꢈꢅꢇ wꢄs ꢇhꢈꢅ ꢉꢈmꢁꢊꢈꢆ ꢋꢅꢆꢈꢉ
ꢉꢈꢆꢋꢃꢈꢆ pꢉꢈssꢋꢉꢈ ꢄꢅꢆ ꢇhꢈ ꢃꢉꢋꢆꢈ ꢉꢈsꢀꢆꢋꢈ wꢄs pꢋꢉꢀfiꢈꢆ
by ꢃꢁꢂꢋmꢅ ꢃhꢉꢁmꢄꢇꢁgꢉꢄphy ꢁꢅ ꢄ ꢃꢁꢂꢋmꢅ (1.530
ꢃm) pꢄꢃkꢈꢆ wꢀꢇh sꢀꢂꢀꢃꢄ gꢈꢂ ꢋsꢀꢅg hꢈxꢄꢅꢈ:ꢈꢇhyꢂ ꢄꢃꢈꢇꢄꢇꢈ
phꢁbꢀꢃꢀꢇy, whꢀꢃh ꢃꢁꢋꢂꢆ bꢈꢅꢈfiꢇ ꢇhꢈꢀꢉ pꢈꢉfꢁꢉmꢄꢅꢃꢈ ꢀꢅ
fꢁꢁꢆ, phꢄꢉmꢄꢃꢈꢋꢇꢀꢃꢄꢂ, ꢄꢅꢆ ꢃꢁsmꢈꢇꢀꢃ ꢄppꢂꢀꢃꢄꢇꢀꢁꢅs.
Materials and methods
Reagents and biocatalysts
vꢀꢅyꢂ ꢄꢃꢈꢇꢄꢇꢈ, ꢊꢀꢅyꢂ ꢂꢄꢋꢉꢄꢇꢈ, ꢄꢅꢆ Fa wꢈꢉꢈ pꢋꢉꢃhꢄsꢈꢆ
fꢉꢁm Sꢀgmꢄ-aꢂꢆꢉꢀꢃh. immꢁbꢀꢂꢀzꢈꢆ ꢂꢀpꢄsꢈ fꢉꢁm
Candida antarctica B (calB, nꢁꢊꢁzym 435, 7400
Plu/g) wꢄs kꢀꢅꢆꢂy ꢆꢁꢅꢄꢇꢈꢆ by nꢁꢊꢁzymꢈs a/S.
immꢁbꢀꢂꢀzꢈꢆ ꢂꢀpꢄsꢈ fꢉꢁm Alcaligenes sp. (QlG, 20000
u/g) wꢄs ꢁbꢇꢄꢀꢅꢈꢆ fꢉꢁm Mꢈꢀꢇꢁ Sꢄꢅgyꢁ cꢁ. (Jꢄpꢄꢅ).
aꢂꢂ ꢁꢇhꢈꢉ ꢉꢈꢄgꢈꢅꢇs wꢈꢉꢈ ꢁf ꢇhꢈ hꢀghꢈsꢇ ꢄꢊꢄꢀꢂꢄbꢂꢈ pꢋꢉꢀꢇy
ꢄꢅꢆ wꢈꢉꢈ ꢋsꢈꢆ ꢄs pꢋꢉꢃhꢄsꢈꢆ, ꢈxꢃꢈpꢇ fꢁꢉ ꢁꢉgꢄꢅꢀꢃ sꢁꢂ-
ꢊꢈꢅꢇs ꢇhꢄꢇ wꢈꢉꢈ ꢆꢉꢀꢈꢆ ꢁꢊꢈꢉ 3-Å mꢁꢂꢈꢃꢋꢂꢄꢉ sꢀꢈꢊꢈs.
®
8:2 (ꢊ/ꢊ) ꢄs ꢈꢂꢋꢈꢅꢇ.
Analytical procedure
rꢈꢄꢃꢇꢀꢁꢅs wꢈꢉꢈ fꢁꢂꢂꢁwꢈꢆ bytlc ꢁꢅ Sꢀꢂꢀꢃꢄ gꢈꢂ 60F254
ꢄꢂꢋmꢀꢅꢋm shꢈꢈꢇs (0.2 mm ꢇhꢀꢃkꢅꢈss, Mꢈꢉꢃk) ꢀꢅ
hꢈxꢄꢅꢈ/ꢈꢇhyꢂ ꢄꢃꢈꢇꢄꢇꢈ 6:4 (ꢊ/ꢊ) wꢀꢇh uv ꢂꢀghꢇ (254
ꢅm) fꢁꢉ ꢆꢈꢇꢈꢃꢇꢀꢁꢅ. HPlc ꢄꢅꢄꢂysꢀs wꢄs pꢈꢉfꢁꢉmꢈꢆ
ꢋsꢀꢅg ꢄ ꢇꢈꢉꢅꢄꢉy pꢋmp (mꢁꢆꢈꢂ 9012,vꢄꢉꢀꢄꢅ) ꢃꢁꢋpꢂꢈꢆ
ꢇꢁ ꢄ ꢇhꢈꢉmꢁsꢇꢄꢇꢈꢆ (25°c) ꢄꢋꢇꢁsꢄmpꢂꢈꢉ (mꢁꢆꢈꢂ
l-2200, Hꢀꢇꢄꢃhꢀ). thꢈ ꢇꢈmpꢈꢉꢄꢇꢋꢉꢈ ꢁf ꢇhꢈ ꢃꢁꢂꢋmꢅ
wꢄs kꢈpꢇ ꢃꢁꢅsꢇꢄꢅꢇ ꢄꢇ 40°c (MeF-01 ꢁꢊꢈꢅ, aꢅꢄꢂꢀsꢀs
vꢀꢅꢀꢃꢁs, Spꢄꢀꢅ).thꢈ ꢃꢁꢂꢋmꢅ wꢄs ꢄ Gꢈmꢀꢅꢀ c6-Phꢈꢅyꢂ
110 Å (4.6150 mm, 5 mm, Phꢈꢅꢁmꢈꢅꢈx), ꢄꢅꢆ ꢇhꢈ
mꢁbꢀꢂꢈ phꢄsꢈ wꢄs mꢈꢇhꢄꢅꢁꢂ/H o 60:40 (ꢊ/ꢊ) (H o
Enzymatic esterification of ferulic acid
tꢁ ꢄ sꢁꢂꢋꢇꢀꢁꢅ ꢁf Fa (10 mg/ml, 51 mM) ꢀꢅ ꢇhꢈ
ꢀ
ꢅꢆꢀꢃꢄꢇꢈꢆ sꢁꢂꢊꢈꢅꢇ, ꢄꢂꢃꢁhꢁꢂ (ꢈꢇhꢄꢅꢁꢂ ꢁꢉ ꢆꢁꢆꢈꢃyꢂ
ꢄꢂꢃꢁhꢁꢂ) ꢄꢅꢆ ꢇhꢈ ꢀmmꢁbꢀꢂꢀzꢈꢆ ꢂꢀpꢄsꢈ wꢈꢉꢈ ꢄꢆꢆꢈꢆ ꢄꢇ
ꢆꢀffꢈꢉꢈꢅꢇ ꢉꢄꢇꢀꢁs. thꢈ ꢇꢁꢇꢄꢂ ꢊꢁꢂꢋmꢈ wꢄs 1 ml. thꢈ
mꢀxꢇꢋꢉꢈs wꢈꢉꢈ ꢀꢅꢃꢋbꢄꢇꢈꢆ ꢄꢇ 60°c ꢀꢅ sꢈꢄꢂꢈꢆ 4-ml
ꢆꢄꢉk ꢊꢀꢄꢂs ꢀꢅ ꢄꢅ ꢁꢉbꢀꢇꢄꢂ ꢀꢅꢃꢋbꢄꢇꢁꢉ Si50 (Sꢇꢋꢄꢉꢇ
Sꢃꢀꢈꢅꢇꢀfiꢃ) ꢄꢇ 250 ꢉpm. aꢂꢀqꢋꢁꢇs (2 ml) wꢈꢉꢈ wꢀꢇh-
ꢆꢉꢄwꢅ ꢄꢇ ꢀꢅꢇꢈꢉꢊꢄꢂs ꢄꢅꢆ ꢇhꢈ pꢉꢁgꢉꢈss ꢁf ꢇhꢈ ꢉꢈꢄꢃꢇꢀꢁꢅ
wꢄs ꢄꢅꢄꢂyzꢈꢆ by ꢇhꢀꢅ-ꢂꢄyꢈꢉ ꢃhꢉꢁmꢄꢇꢁgꢉꢄphy (tlc).
Fꢁꢉ ꢇhꢈ qꢋꢄꢅꢇꢀfiꢃꢄꢇꢀꢁꢅ ꢁf Fa ꢈsꢇꢈꢉs, ꢇhꢈ ꢉꢈꢄꢃꢇꢀꢁꢅs
wꢈꢉꢈ sꢇꢁppꢈꢆ by fiꢂꢇꢈꢉꢀꢅg ꢇhꢈ mꢀxꢇꢋꢉꢈ wꢀꢇh ꢃꢈꢅꢇꢉꢀfꢋgꢈ
ꢇꢋbꢈs ꢃꢁꢅꢇꢄꢀꢅꢀꢅg ꢄ pꢁꢂyꢊꢀꢅyꢂꢀꢆꢈꢅꢈ ꢆꢀflꢋꢁꢉꢀꢆꢈ (PvdF)
dꢋꢉꢄpꢁꢉꢈ 0.45-mm mꢈmbꢉꢄꢅꢈ (Mꢀꢂꢂꢀpꢁꢉꢈ) ꢄꢅꢆ ꢇhꢈ
sꢋpꢈꢉꢅꢄꢇꢄꢅꢇs wꢈꢉꢈ ꢄꢅꢄꢂyzꢈꢆ by hꢀgh-pꢈꢉfꢁꢉmꢄꢅꢃꢈ
ꢂꢀqꢋꢀꢆ ꢃhꢉꢁmꢄꢇꢁgꢉꢄphy (HPlc). iꢅ ꢁꢉꢆꢈꢉ ꢇꢁ
ꢃhꢈmꢀꢃꢄꢂꢂy ꢃhꢄꢉꢄꢃꢇꢈꢉꢀzꢈ ꢇhꢈ ꢉꢈꢄꢃꢇꢀꢁꢅ pꢉꢁꢆꢋꢃꢇs, ꢇhꢈ
ꢉꢈꢄꢃꢇꢀꢁꢅs wꢈꢉꢈ sꢃꢄꢂꢈꢆ-ꢋp ꢇꢁ 10 ml. thꢈ sꢁꢂꢀꢆ
2
2
ꢃꢁꢅꢇꢄꢀꢅꢈꢆ 0.1% ꢊ/ꢊ ꢁf ꢄꢃꢈꢇꢀꢃ ꢄꢃꢀꢆ) ꢄꢇ 1 ml/mꢀꢅ.
dꢈꢇꢈꢃꢇꢀꢁꢅ wꢄs pꢈꢉfꢁꢉmꢈꢆ wꢀꢇh ꢄ phꢁꢇꢁꢆꢀꢁꢆꢈ ꢄꢉꢉꢄy
ꢆꢈꢇꢈꢃꢇꢁꢉ (PꢉꢁSꢇꢄꢉ, vꢄꢉꢀꢄꢅ), ꢄꢅꢆ ꢀꢅꢇꢈgꢉꢄꢇꢀꢁꢅ wꢄs ꢃꢄꢉ-
ꢉꢀꢈꢆ ꢁꢋꢇ ꢋsꢀꢅg ꢇhꢈ vꢄꢉꢀꢄꢅ Sꢇꢄꢉ lc Wꢁꢉksꢇꢄꢇꢀꢁꢅ 6.41.
Fa ꢄꢅꢆ ꢇhꢈꢀꢉ ꢈsꢇꢈꢉs wꢈꢉꢈ qꢋꢄꢅꢇꢀfiꢈꢆ ꢄꢇ 310 ꢅm ꢋsꢀꢅg
ꢇhꢈ pꢋꢉꢀfiꢈꢆ ꢃꢁmpꢁꢋꢅꢆs ꢄs sꢇꢄꢅꢆꢄꢉꢆs. Mꢈꢂꢇꢀꢅg pꢁꢀꢅꢇs
wꢈꢉꢈ mꢈꢄsꢋꢉꢈꢆ ꢀꢅ ꢄ Fꢀshꢈꢉ-Jꢁhꢅs ꢄppꢄꢉꢄꢇꢋs ꢄꢅꢆ ꢄꢉꢈ
ꢋꢅꢃꢁꢉꢉꢈꢃꢇꢈꢆ. Fꢁꢋꢉꢀꢈꢉ ꢇꢉꢄꢅsfꢁꢉm ꢀꢅfꢉꢄꢉꢈꢆ spꢈꢃꢇꢉꢁs-
ꢃꢁpy (Ftir) spꢈꢃꢇꢉꢄ wꢈꢉꢈ ꢁbꢇꢄꢀꢅꢈꢆ ꢁꢅ ꢄ Shꢀmꢄꢆzꢋ
1
Ftir-8300 spꢈꢃꢇꢉꢁphꢁꢇꢁmꢈꢇꢈꢉ. H ꢅꢋꢃꢂꢈꢄꢉ mꢄgꢅꢈꢇꢀꢃ

Ferulic acid esterification
3
ꢉꢈsꢁꢅꢄꢅꢃꢈ ( H nMr) ꢄꢅꢆ 13c nMr spꢈꢃꢇꢉꢄ wꢈꢉꢈ
1
14.3; 20.6; 55.9; 60.6; 111.2; 118.5; 121.2; 123.2;
133.4;141.4;143.8;151.4;166.6;168.8.Hr-eSi-MS:
[MH] 265.1061; [Mnꢄ] 287.0889.
ꢉꢈꢃꢁꢉꢆꢈꢆ ꢀꢅ cdcꢂ ꢄs sꢁꢂꢊꢈꢅꢇ ꢋsꢀꢅg ꢄ BꢉꢋkꢈꢉaM-500
nMr ꢀꢅsꢇꢉꢋmꢈꢅꢇ ꢁpꢈꢉꢄꢇꢀꢅg ꢄꢇ 500.1 MHz ꢄꢅꢆ 125.8
3


1
13
MHz fꢁꢉ H ꢄꢅꢆ c, ꢉꢈspꢈꢃꢇꢀꢊꢈꢂy. chꢈmꢀꢃꢄꢂ shꢀfꢇs
ꢄꢉꢈ ꢉꢈpꢁꢉꢇꢈꢆ ꢀꢅ d ꢋꢅꢀꢇs (ppm) ꢉꢈꢂꢄꢇꢀꢊꢈ ꢇꢁ ꢇꢈꢇꢉꢄmꢈꢇh-
yꢂsꢀꢂꢄꢅꢈ sꢈꢇ ꢄꢇ 0 ppm, ꢄꢅꢆ ꢃꢁꢋpꢂꢀꢅg ꢃꢁꢅsꢇꢄꢅꢇs ꢄꢉꢈ
gꢀꢊꢈꢅ ꢀꢅ Hz. Mꢄss spꢈꢃꢇꢉꢁmꢈꢇꢉy (MS) ꢄꢅꢄꢂysꢀs wꢄs
ꢃꢄꢉꢉꢀꢈꢆ ꢁꢋꢇ ꢋsꢀꢅg ꢄ mꢄss spꢈꢃꢇꢉꢁmꢈꢇꢈꢉ (mꢁꢆꢈꢂ
QStar pꢋꢂsꢄꢉ, appꢂꢀꢈꢆ Bꢀꢁsysꢇꢈms) wꢀꢇh ꢄ hybꢉꢀꢆ
qꢋꢄꢆꢉꢋpꢁꢂꢈ ꢇꢀmꢈ-ꢁf-flꢀghꢇ ꢁꢉ QtoF ꢄꢅꢄꢂyzꢈꢉ. iꢁꢅꢀzꢄ-
ꢇꢀꢁꢅ wꢄs pꢈꢉfꢁꢉmꢈꢆ by ꢈꢂꢈꢃꢇꢉꢁspꢉꢄy ꢀꢅ pꢁsꢀꢇꢀꢊꢈ mꢁꢆꢈ.
Hꢀgh-ꢉꢈsꢁꢂꢋꢇꢀꢁꢅ MS ꢁꢉ HrMS wꢄs ꢉꢈꢃꢁꢉꢆꢈꢆ wꢀꢇh ꢄ
thꢈꢉmꢁ Sꢃꢀꢈꢅꢇꢀfiꢃ eM/dSQ ii-diP spꢈꢃꢇꢉꢁmꢈꢇꢈꢉ.
thꢈ ꢉꢈsꢋꢂꢇs ꢄꢉꢈ wꢀꢇhꢀꢅ 0.02% ꢁf ꢇhꢈ ꢇhꢈꢁꢉꢈꢇꢀꢃꢄꢂ
ꢊꢄꢂꢋꢈs.
(E)-Ethyl 3-(4-dodecanoyloxy-3-methoxyphenyl)-prop-
2-enoate (5)
Yꢀꢈꢂꢆ 52%, whꢀꢇꢈ sꢁꢂꢀꢆ, mꢈꢂꢇꢀꢅg pꢁꢀꢅꢇ 34–35°c.
Ft-ir (fiꢂm) nmꢄx 2930, 2850, 1698, 1685, 1560

1 1
ꢃm . H nMr: d 0.88 (ꢇ, J7.0 Hz, 3H); 1.26–1.33
m, 16H); 1.34 (ꢇ, J7.0 Hz, 3H); 1.63 (m, 2H);
(
1
4
7
1
3
1
.76 (m, 2H); 2.58 (ꢇ, J7.0 Hz, 2H); 3.85 (s, 3H);
.27 (ꢃ, J7.0 Hz, 2H); 6.38 (ꢆ, J16.0 Hz, 1H);
13
.11 (ꢆꢆ, J10; 2.0 Hz, 1H). c nMr: d 14.1;
4.3; 22.7; 24.7; 29.1; 29.2; 29.3; 29.4: 29.5; 29.6;
4.0; 55.9; 60.6; 111.2; 118.4; 121,2; 123.3; 133.3;
41.6; 144.0; 151.4; 166.9; 171.7. Hr-eSi-MS:
Ethyl-(E)-3-(4-hydroxy-3-methoxyphenyl)-prop-


[MH] 405.2603; [Mnꢄ] 427.2413.
2-enoate (2)
Yꢀꢈꢂꢆ 93%, whꢀꢇꢈ sꢁꢂꢀꢆ, mꢈꢂꢇꢀꢅg pꢁꢀꢅꢇ 39–41°c (ꢂꢀꢇ.
mp, 39°c) (nꢁꢅꢅꢈꢅmꢄꢃhꢈꢉ ꢈꢇ ꢄꢂ. 1983). Ft-ir (fiꢂm)
nmꢄx3403, 2980, 1698, 1633, 1593, 1515 ꢃm1.1H
nMr: d 1.33 (ꢇ, J7.0 Hz, 3H); 3.93 (s, 3H); 4.27
Anti-inflammatory activity
aꢅꢇꢀ-ꢀꢅflꢄmmꢄꢇꢁꢉy ꢄꢃꢇꢀꢊꢀꢇy wꢄs mꢈꢄsꢋꢉꢈꢆ in ꢊꢀꢇꢉꢁ
ꢄs pꢈꢉꢃꢈꢅꢇꢄgꢈ ꢁf ꢀꢅhꢀbꢀꢇꢀꢁꢅ ꢁf ꢃyꢃꢂꢁꢁxygꢈꢅꢄsꢈ 2
(coX2) ꢋsꢀꢅg ꢇhꢈ cꢁꢂꢁꢉꢀmꢈꢇꢉꢀꢃ coX oꢊꢀꢅꢈ iꢅhꢀbꢀ-
ꢇꢁꢉ Kꢀꢇ (cꢄymꢄꢅ chꢈmꢀꢃꢄꢂ, uSa), ꢄꢃꢃꢁꢉꢆꢀꢅg ꢇꢁ ꢇhꢈ
mꢄꢅꢋfꢄꢃꢇꢋꢉꢈꢉ’s ꢀꢅsꢇꢉꢋꢃꢇꢀꢁꢅs. Sꢇꢁꢃk sꢁꢂꢋꢇꢀꢁꢅs ꢁf ꢇhꢈ
ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs wꢈꢉꢈ pꢉꢈpꢄꢉꢈꢆ ꢀꢅ ꢆꢀmꢈꢇhyꢂ sꢋꢂfꢁxꢀꢆꢈ
(dMSo). dꢀꢃꢂꢁfꢈꢅꢄꢃ wꢄs ꢋsꢈꢆ ꢄs sꢇꢄꢅꢆꢄꢉꢆ.
(
ꢃ, J7.0 Hz, 2H); 6.29 (ꢆ, J16.0 Hz, 1H); 6.96
ꢆ, J10.0 Hz, 1H); 7.08 (ꢆ, J2.0 Hz, 1H); 7.12
ꢆꢆ, J10.0; 2.0 Hz, 1H);7.61 (ꢆ, J16.0 Hz, 1H).
(
(
1
3
c nMr: d 14.4; 55.9; 60.4; 109.3; 114.7; 115,7;
1
23.0;127.0;144.6;146.7;147.9;167.3.Hr-eSi-MS:


[MH] 223.0954; [Mnꢄ] 245.0806.
Dodecyl-(E)-3-(4-hydroxy-3-methoxyphenyl)-prop-
-enoate (3)
Statistical analysis
2
dꢄꢇꢄ ꢄꢉꢈ pꢉꢈsꢈꢅꢇꢈꢆ ꢄs mꢈꢄꢅ  sꢇꢄꢅꢆꢄꢉꢆ ꢈꢉꢉꢁꢉ (Se)
fꢉꢁm ꢄꢇ ꢂꢈꢄsꢇ ꢇwꢁ ꢀꢅꢆꢈpꢈꢅꢆꢈꢅꢇ ꢄꢅꢄꢂysꢈs. oꢉꢀgꢀꢅPꢉꢁ
sꢁfꢇwꢄꢉꢈ (ꢊ. 8.5.1) wꢄs ꢋsꢈꢆ fꢁꢉ sꢇꢄꢇꢀsꢇꢀꢃꢄꢂ ꢄꢅꢄꢂysꢀs.
Yꢀꢈꢂꢆ 85%, whꢀꢇꢈ sꢁꢂꢀꢆ, mꢈꢂꢇꢀꢅg pꢁꢀꢅꢇ 36–37°c.
Ft-ir (fiꢂm) n 3400, 2985, 1694, 1625, 1592,
tM
mꢄx

1 1
1
1
3
510 ꢃm . H nMr: d 0.88 (ꢇ, J7.0 Hz, 3H);
.26–1.36 (m, 16H); 1.57 (m, 2H), 1.70 (m, 2H);
.93 (s, 3H); 4.19 (ꢇ, J7.0 Hz, 2H); 6.29 (ꢆ,
Results and discussion
J16.0 Hz, 1H); 6.91(ꢆ, J10.0 Hz, 1H); 7.04 (ꢆ,
J2.0 Hz, 1H); 7.10 (ꢆ, J2 Hz, 1H); 7.11 (ꢆꢆ,
J10.0; 2.0 Hz, 1H); 7.64 (ꢆ, J16.0 Hz, 1H).
thꢈ pꢉꢈsꢈꢅꢃꢈ ꢁf ꢄ phꢈꢅꢁꢂꢀꢃ ꢄꢅꢆ ꢄꢅ ꢄꢃꢀꢆ gꢉꢁꢋp ꢀꢅ ꢄ
sꢀꢅgꢂꢈ mꢁꢂꢈꢃꢋꢂꢈ ꢁf Fa (1) mꢄkꢈs ꢇhꢀs ꢃꢁmpꢁꢋꢅꢆ ꢄꢅ
1
3
c
nMr: d 14.1; 22.7; 25.7; 28.7; 29.2; 29.3; 29.4:
ꢀ
ꢅꢇꢈꢉꢈsꢇꢀꢅg mꢁꢆꢈꢂ fꢁꢉ ꢈꢅzymꢄꢇꢀꢃ mꢁꢆꢀfiꢃꢄꢇꢀꢁꢅs. iꢅ
gꢈꢅꢈꢉꢄꢂ, ꢄꢂkyꢂ mꢁꢅꢁꢈsꢇꢈꢉs ꢁf hyꢆꢉꢁxyꢃꢀꢅꢅꢄmꢀꢃ ꢄꢃꢀꢆs
ꢅꢃꢂꢋꢆꢀꢅg Fa ꢃꢄꢅ bꢈ ꢁbꢇꢄꢀꢅꢈꢆ by ꢆꢀꢉꢈꢃꢇ ꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ
2
1
9.5; 29.6; 32.8; 55.9; 64.6; 109.3; 114.7; 115,6;
23.0;127.0;144.6;146.8;147.9;163.8.Hr-eSi-MS:
ꢀ


[
MH] 363.2525; [Mnꢄ] 385.2351.
wꢀꢇh ꢄꢂꢃꢁhꢁꢂs (Wꢈꢀꢇkꢄmp ꢈꢇ ꢄꢂ. 2006) ꢁꢉ by ꢇꢉꢄꢅsꢈs-
ꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢁf mꢈꢇhyꢂ ꢁꢉ ꢈꢇhyꢂ Fa ꢈsꢇꢈꢉs wꢀꢇh ꢂꢁꢅg-
ꢃhꢄꢀꢅ ꢄꢂꢃꢁhꢁꢂs (cꢁmpꢇꢁꢅ ꢈꢇ ꢄꢂ. 2000).thꢈ phꢈꢅꢁꢂꢀꢃ
gꢉꢁꢋps ꢁf ꢇhꢈ syꢅꢇhꢈsꢀzꢈꢆ mꢁꢅꢁꢈsꢇꢈꢉs ꢃꢄꢅ bꢈ fꢋꢉꢇhꢈꢉ
ꢄꢃyꢂꢄꢇꢈꢆ ꢇꢁ pꢉꢁꢆꢋꢃꢈ ꢇhꢈ ꢃꢁꢉꢉꢈspꢁꢅꢆꢀꢅg ꢆꢀꢈsꢇꢈꢉs. iꢅ
ꢇhꢀs wꢁꢉk, wꢈ ꢀꢅꢊꢈsꢇꢀgꢄꢇꢈꢆ ꢇhꢈ bꢈhꢄꢊꢀꢁꢉ ꢁf ꢆꢀffꢈꢉꢈꢅꢇ
ꢂꢀpꢄsꢈs ꢀꢅ ꢇhꢈ ꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢄꢅꢆ ꢄꢃyꢂꢄꢇꢀꢁꢅ ꢁf Fa,
ꢄꢀmꢀꢅg ꢇꢁ ꢀmpꢉꢁꢊꢈ ꢇhꢈ pꢉꢁꢆꢋꢃꢇꢀꢊꢀꢇy ꢁf ꢇhꢈ pꢉꢁꢃꢈss ꢁꢉ
ꢇꢁ syꢅꢇhꢈsꢀzꢈ ꢅꢁꢊꢈꢂ ꢂꢀpꢁphꢀꢂꢀꢃ ꢃꢁmpꢁꢋꢅꢆs. Fꢀgꢋꢉꢈ 1
ꢀꢂꢂꢋsꢇꢉꢄꢇꢈs ꢇhꢈ ꢂꢀpꢄsꢈ-ꢃꢄꢇꢄꢂyzꢈꢆ ꢉꢈꢄꢃꢇꢀꢁꢅs ꢆꢈsꢃꢉꢀbꢈꢆ ꢀꢅ
ꢇhꢈ pꢉꢈsꢈꢅꢇ wꢁꢉk.
(
2
E)-Ethyl 3-(4-acetoxy-3-methoxyphenyl)-prop-
-enoate (4)
Yꢀꢈꢂꢆ 59%, whꢀꢇꢈ sꢁꢂꢀꢆ, mꢈꢂꢇꢀꢅg pꢁꢀꢅꢇ 68–69°c. Ft-ir
fiꢂm) nmꢄx2923, 2848, 1697, 1682, 1557 ꢃm1.1H
nMr: d 1.34 (ꢇ, J7.0 Hz, 3H); 2.32 (s, 3H); 3.86
s, 3H); 4.27 (ꢃ, J7.0 Hz, 2H); 6.37 (ꢆ, J16.0
Hz, 1H); 7.05 (ꢆ, J10.0 Hz, 1H); 7.13 (ꢆꢆ, J10;
.0 Hz, 1H); 7.64 (ꢆ, J16.0 Hz, 1H). 13c nMr: d
(
(
2

4
G. Sandoval et al.
Fꢀgꢋꢉꢈ 1. Sꢃhꢈmꢈ ꢁf ꢇhꢈ ꢂꢀpꢄsꢈ-ꢃꢄꢇꢄꢂyzꢈꢆ syꢅꢇhꢈsꢀs ꢁf Fa mꢁꢅꢁ- ꢄꢅꢆ ꢆꢀꢈsꢇꢈꢉs.
Esterification of ferulic acid
thꢈ mꢁꢂꢈꢃꢋꢂꢄꢉfꢁꢉmꢋꢂꢄwꢄsꢆꢈꢇꢈꢉmꢀꢅꢈꢆꢄsc H o ,
22 34 4
ꢁ
ꢅ ꢇhꢈ bꢄsꢀs ꢁf ꢇhꢈ Hr-eSi-MS spꢈꢃꢇꢉꢋm. thꢈ
Sꢈꢊꢈꢉꢄꢂ ꢀmmꢁbꢀꢂꢀzꢈꢆ ꢂꢀpꢄsꢈs fꢉꢁm bꢄꢃꢇꢈꢉꢀꢄ (ꢈ.g.,
Pseudomonas cepacia ꢄꢅꢆ Alcaligenes sp.), fꢋꢅgꢀ (ꢈ.g.,
Rhizomucor miehei ꢄꢅꢆ Thermomyces lanuginosus),
yꢈꢄsꢇs (ꢈ.g., Candida antarctica ꢄꢅꢆ Yarrowia lipolyt-
ica), ꢄꢅꢆ pꢂꢄꢅꢇs (ꢈ.g., Carica papaya) wꢈꢉꢈ ꢈꢊꢄꢂꢋꢄꢇꢈꢆ
mꢁꢂꢈꢃꢋꢂꢄꢉ ꢀꢁꢅ wꢄs 168 dꢄ ꢂꢄꢉgꢈꢉ ꢇhꢄꢅ ꢇhꢄꢇ ꢁf Fa,
whꢀꢃh ꢀꢅꢆꢀꢃꢄꢇꢈꢆ ꢇhꢈ fꢁꢉmꢄꢇꢀꢁꢅ ꢁf ꢇhꢈ ꢂꢄꢋꢉyꢂ ꢈsꢇꢈꢉ.
thꢀs wꢄs ꢄꢂsꢁ ꢈsꢇꢄbꢂꢀshꢈꢆ by ꢁbsꢈꢉꢊꢀꢅg ꢇhꢈ ꢇꢉꢀpꢂꢈꢇ ꢄꢇ
d 0.88 ꢃꢁꢉꢉꢈspꢁꢅꢆꢀꢅg ꢇꢁ mꢈꢇhyꢂ gꢉꢁꢋp, mꢋꢂꢇꢀpꢂꢈꢇs ꢄꢇ
d 1.26–1.36, 1.57, ꢄꢅꢆ 1.70 ꢃꢁꢉꢉꢈspꢁꢅꢆꢀꢅg ꢇꢁ ꢇhꢈ
ꢃhꢄꢀꢅ mꢈꢇhyꢂꢈꢅꢈ gꢉꢁꢋps, ꢄꢅꢆ ꢄ ꢇꢉꢀpꢂꢈꢇ ꢄꢇ d 4.19
ꢀꢅ ꢆꢀffꢈꢉꢈꢅꢇ sꢁꢂꢊꢈꢅꢇs fꢁꢉ ꢇhꢈ ꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢁf Fa wꢀꢇh
ꢇwꢁ ꢄꢂꢀphꢄꢇꢀꢃ ꢄꢂꢃꢁhꢁꢂs: ꢈꢇhꢄꢅꢁꢂ ꢄꢅꢆ ꢂꢄꢋꢉyꢂ ꢄꢂꢃꢁhꢁꢂ.
(
t, J7.0 Hz) ꢄssꢀgꢅꢈꢆ ꢇꢁ ꢇhꢈ mꢈꢇhyꢂꢈꢅꢈ gꢉꢁꢋp
rꢈꢄꢃꢇꢀꢁꢅs wꢈꢉꢈ ꢃꢄꢉꢉꢀꢈꢆ ꢁꢋꢇ ꢄꢇ 60°c ꢋsꢀꢅg 10 mg/ml
bꢁꢅꢆꢈꢆ ꢇꢁ ꢇhꢈ ꢃꢄꢉbꢁxyꢂꢀꢃ ꢁxygꢈꢅ.
ꢁf Fa, ꢄꢅ ꢄꢂꢃꢁhꢁꢂ/Fa mꢁꢂꢄꢉ ꢉꢄꢇꢀꢁ ꢁf 10, ꢄꢅꢆ 100 mg/
iꢅ ꢁꢉꢆꢈꢉ ꢇꢁ ꢁpꢇꢀmꢀzꢈ ꢇhꢈ yꢀꢈꢂꢆ ꢁf ꢇhꢈ syꢅꢇhꢈsꢀzꢈꢆ
ꢈsꢇꢈꢉs wꢈ ꢊꢄꢉꢀꢈꢆ sꢈꢊꢈꢉꢄꢂ ꢉꢈꢄꢃꢇꢀꢁꢅ pꢄꢉꢄmꢈꢇꢈꢉs sꢋꢃh ꢄs
ꢇhꢈ ꢁꢉgꢄꢅꢀꢃ sꢁꢂꢊꢈꢅꢇ, ꢇꢈmpꢈꢉꢄꢇꢋꢉꢈ, ꢇhꢈ mꢁꢂꢄꢉ ꢉꢄꢇꢀꢁ
ꢄꢂꢃꢁhꢁꢂ/Fa, ꢄꢅꢆ ꢇhꢈ ꢄmꢁꢋꢅꢇ ꢁf bꢀꢁꢃꢄꢇꢄꢂysꢇ.
ml ꢁf bꢀꢁꢃꢄꢇꢄꢂysꢇ. tlc mꢁꢅꢀꢇꢁꢉꢀꢅg ꢀꢅꢆꢀꢃꢄꢇꢈꢆ ꢇhꢄꢇ,
ꢄmꢁꢅg ꢇhꢈ ꢇꢈsꢇꢈꢆ ꢂꢀpꢄsꢈs, ꢁꢅꢂy ꢇhꢈ ꢂꢀpꢄsꢈ fꢉꢁm
C. antarctica B (calB) ꢄffꢁꢉꢆꢈꢆ ꢇhꢈ eF 2 ꢄꢅꢆ lF 3
ꢀꢅ sꢀgꢅꢀfiꢃꢄꢅꢇ ꢄmꢁꢋꢅꢇs. iꢅ ꢇhꢈ ꢄbsꢈꢅꢃꢈ ꢁf bꢀꢁꢃꢄꢇꢄꢂysꢇ
ꢅꢁ pꢉꢁꢆꢋꢃꢇ wꢄs ꢆꢈꢇꢈꢃꢇꢈꢆ.
thꢈ ꢃꢁꢉꢉꢈspꢁꢅꢆꢀꢅg ꢈsꢇꢈꢉ ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs 2 ꢄꢅꢆ 3 wꢈꢉꢈ
sꢁꢂꢄꢇꢈꢆ ꢄꢅꢆ ꢃhꢄꢉꢄꢃꢇꢈꢉꢀzꢈꢆ. eF (2) wꢄs fꢋꢂꢂy ꢀꢆꢈꢅꢇꢀ-
Effect of organic solvent
ꢀ
fiꢈꢆ by mꢈꢂꢇꢀꢅg pꢁꢀꢅꢇ ꢄꢅꢆ spꢈꢃꢇꢉꢁsꢃꢁpꢀꢃ ꢇꢈꢃhꢅꢀqꢋꢈs,
whꢀꢃh wꢈꢉꢈ ꢀꢅ ꢄꢃꢃꢁꢉꢆꢄꢅꢃꢈ wꢀꢇh ꢉꢈpꢁꢉꢇꢈꢆ ꢆꢄꢇꢄ
iꢇ ꢀs wꢈꢂꢂ kꢅꢁwꢅ ꢇhꢄꢇ ꢅꢁꢅ-pꢁꢂꢄꢉ sꢁꢂꢊꢈꢅꢇs ꢄꢉꢈ ꢄppꢉꢁpꢉꢀ-
ꢄꢇꢈ mꢈꢆꢀꢄ fꢁꢉ ꢂꢀpꢄsꢈ-ꢃꢄꢇꢄꢂyzꢈꢆ ꢉꢈꢄꢃꢇꢀꢁꢅs (Pꢂꢁꢋ ꢈꢇ ꢄꢂ.
2002; Qꢋꢀꢅꢇꢄꢅꢄ ꢈꢇ ꢄꢂ. 2011). Sꢋꢃh hyꢆꢉꢁphꢁbꢀꢃ
ꢁꢉgꢄꢅꢀꢃ sꢁꢂꢊꢈꢅꢇs ꢁffꢈꢉ sꢈꢊꢈꢉꢄꢂ ꢄꢆꢊꢄꢅꢇꢄgꢈs, sꢋꢃh ꢄs ꢇhꢈ
ꢈꢅhꢄꢅꢃꢈmꢈꢅꢇ ꢁf sꢁꢂꢋbꢀꢂꢀꢇy ꢁf ꢅꢁꢅ-pꢁꢂꢄꢉ ꢉꢈꢄꢃꢇꢄꢅꢇs,
ꢄꢅ ꢀmpꢉꢁꢊꢈꢆ sꢇꢄbꢀꢂꢀꢇy ꢁf ꢇhꢈ ꢈꢅzymꢈ, ꢄ shꢀfꢇ ꢀꢅ ꢇhꢈ
ꢈqꢋꢀꢂꢀbꢉꢀꢋm ꢇꢁwꢄꢉꢆ pꢉꢁꢆꢋꢃꢇ fꢁꢉmꢄꢇꢀꢁꢅ, ꢄꢅꢆ ꢈꢄsꢀꢈꢉ
sꢈpꢄꢉꢄꢇꢀꢁꢅ ꢁf ꢇhꢈ ꢈꢅzymꢈ fꢉꢁm ꢇhꢈ ꢉꢈꢄꢃꢇꢀꢁꢅ mꢈꢆꢀꢋm
ꢄꢇ ꢇhꢈ ꢈꢅꢆ ꢁf ꢇhꢈ pꢉꢁꢃꢈss (cꢄꢉꢉꢈꢄ & rꢀꢊꢄ 2008).thꢈ
sꢁꢂꢊꢈꢅꢇs sꢈꢂꢈꢃꢇꢈꢆ fꢁꢉ ꢇhꢀs sꢃꢉꢈꢈꢅꢀꢅg wꢈꢉꢈ ꢀsꢁꢁꢃꢇꢄꢅꢈ,
ꢆꢀꢀsꢁpꢉꢁpyꢂ ꢈꢇhꢈꢉ (diPe), ꢄꢅꢆ 2-mꢈꢇhyꢂ-2-bꢋꢇꢄꢅꢁꢂ
(2M2B), whꢁsꢈ ꢂꢁgP ꢊꢄꢂꢋꢈs ꢄꢉꢈ ꢀꢅ ꢇhꢈ ꢉꢄꢅgꢈ 1.1–4.4,
ꢄꢅꢆ ꢄ sꢁꢂꢊꢈꢅꢇ-fꢉꢈꢈ sysꢇꢈm, ꢀꢅ whꢀꢃh ꢇhꢈ ꢄꢂꢃꢁhꢁꢂ ꢄꢃꢇs
ꢄs bꢋꢂk sꢁꢂꢊꢈꢅꢇ.tꢄbꢂꢈ i ꢀꢅꢆꢀꢃꢄꢇꢈs ꢇhꢄꢇ ꢇhꢈ ꢉꢈsꢋꢂꢇs wꢈꢉꢈ
hꢀghꢂy ꢆꢈpꢈꢅꢆꢈꢅꢇ ꢁꢅ ꢇhꢈ sꢁꢂꢊꢈꢅꢇ sꢈꢂꢈꢃꢇꢈꢆ. dꢋꢈ ꢇꢁ ꢇhꢈ
pꢉꢈsꢈꢅꢃꢈ ꢁf ꢇhꢈ phꢈꢅꢁꢂ ꢄꢅꢆ ꢇhꢈ ꢃꢄꢉbꢁxyꢂꢀꢃ gꢉꢁꢋp, ꢇhꢈ
sꢁꢂꢋbꢀꢂꢀꢇy ꢁf Fa ꢀꢅ ꢀsꢁꢁꢃꢇꢄꢅꢈ wꢄs ꢂꢀmꢀꢇꢈꢆ. iꢅ 2M2B
(nꢁꢅꢅꢈꢅmꢄꢃhꢈꢉ ꢈꢇ ꢄꢂ. 1983).thꢈ mꢁꢂꢈꢃꢋꢂꢄꢉ fꢁꢉmꢋꢂꢄ
wꢄs ꢆꢈꢇꢈꢉmꢀꢅꢈꢆ ꢄs c H o , ꢁꢅ ꢇhꢈ bꢄsꢀs ꢁf ꢇhꢈ
12
14
4
Hr-ꢈꢂꢈꢃꢇꢉꢁspꢉꢄy ꢀꢁꢅꢀzꢄꢇꢀꢁꢅ (eSi)-MS spꢈꢃꢇꢉꢋm.thꢈ
mꢁꢂꢈꢃꢋꢂꢄꢉ ꢀꢁꢅ wꢄs 28 dꢄ ꢂꢄꢉgꢈꢉ ꢇhꢄꢅ ꢇhꢄꢇ ꢁf Fa,
whꢀꢃh ꢀꢅꢆꢀꢃꢄꢇꢈꢆ ꢇhꢈ fꢁꢉmꢄꢇꢀꢁꢅ ꢁf ꢇhꢈ ꢈꢇhyꢂ ꢈsꢇꢈꢉ.
1
cꢁmpꢄꢉꢈꢆ wꢀꢇh ꢀꢇs pꢄꢉꢈꢅꢇ ꢃꢁmpꢁꢋꢅꢆ, ꢇhꢈ H nMr
spꢈꢃꢇꢉꢋm ꢁf 2 ꢈxhꢀbꢀꢇꢈꢆ ꢇwꢁ ꢅꢈw sꢀgꢅꢄꢂs ꢃꢁꢉꢉꢈspꢁꢅꢆ-
ꢀ
4
ꢅg ꢇꢁ ꢇhꢈ ꢈꢇhyꢂ gꢉꢁꢋp. thꢈ mꢈꢇhyꢂꢈꢅꢈ ꢄppꢈꢄꢉꢈꢆ ꢄꢇ d
.27 (ꢃ, J7 Hz) ꢄꢅꢆ ꢄ ꢇꢉꢀpꢂꢈꢇ ꢄꢇ d 1.33 wꢀꢇh J7
1
3
Hz ꢃꢁꢉꢉꢈspꢁꢅꢆꢀꢅg ꢇꢁ ꢇhꢈ mꢈꢇhyꢂ gꢉꢁꢋp. iꢅ ꢇhꢈ
c
spꢈꢃꢇꢉꢋm ꢁf 2, ꢇwꢁ ꢅꢈw sꢀgꢅꢄꢂs ꢄꢇ d 14.1 ꢄꢅꢆ 55.9
wꢈꢉꢈ ꢁbsꢈꢉꢊꢈꢆ ꢃꢁꢉꢉꢈspꢁꢅꢆꢀꢅg ꢇꢁ ꢇhꢈ mꢈꢇhyꢂ ꢄꢅꢆ
mꢈꢇhyꢂꢈꢅꢈ ꢃꢄꢉbꢁꢅs, ꢉꢈspꢈꢃꢇꢀꢊꢈꢂy.
Spꢈꢃꢇꢉꢁsꢃꢁpꢀꢃ ꢄꢅꢄꢂysꢀs ꢁf ꢇhꢈ pꢉꢁꢆꢋꢃꢇ 3 wꢄs
ꢃꢁꢅsꢀsꢇꢈꢅꢇ wꢀꢇh ꢇhꢈ fꢁꢉmꢄꢇꢀꢁꢅ ꢁf ꢇhꢈ ꢂꢄꢋꢉyꢂ ꢈsꢇꢈꢉ.

Ferulic acid esterification
5
tꢄbꢂꢈ i. iꢅflꢋꢈꢅꢃꢈ ꢁf ꢇhꢈ sꢁꢂꢊꢈꢅꢇ ꢁꢅ ꢇhꢈ ꢈꢅzymꢄꢇꢀꢃ ꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ
f Fa wꢀꢇh ꢈꢇhꢄꢅꢁꢂ ꢄꢅꢆ ꢂꢄꢋꢉyꢂ ꢄꢂꢃꢁhꢁꢂ.
ꢁ
esꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢄgꢈꢅꢇ
eꢇhꢄꢅꢁꢂ lꢄꢋꢉyꢂ ꢄꢂꢃꢁhꢁꢂ
Sꢁꢂꢊꢈꢅꢇ
ꢂꢁgP
Sꢁꢂꢊꢈꢅꢇ-fꢉꢈꢈ





2
M2B
1.09
1.40
4.37
diPe
isꢁꢁꢃꢇꢄꢅꢈ




expꢈꢉꢀmꢈꢅꢇꢄꢂ ꢃꢁꢅꢆꢀꢇꢀꢁꢅs: 10 mg/ml Fa; eꢇoH/Fa ꢉꢄꢇꢀꢁ 4:1;
lꢄꢋoH/Fa 1:1; 100 mg/ml calB; 60°c; rꢈꢄꢃꢇꢀꢁꢅ ꢇꢀmꢈ 24 h.
) ꢄppꢉꢁx. 0.56 mmꢁꢂ l
1
h
1
; () nꢁ ꢉꢈꢄꢃꢇꢀꢁꢅ.
(
ꢀꢇ wꢄs ꢃꢁmpꢂꢈꢇꢈꢂy sꢁꢂꢋbꢂꢈ, bꢋꢇ ꢇhꢈ ꢄssꢄyꢈꢆ ꢂꢀpꢄsꢈs
wꢈꢉꢈ ꢅꢁꢇ ꢄꢃꢇꢀꢊꢈ. iꢅ ꢇhꢈ sꢁꢂꢊꢈꢅꢇ-fꢉꢈꢈ sysꢇꢈm ꢁꢅꢂy pꢉꢁꢆ-
ꢋꢃꢇ 3 wꢄs ꢁbꢇꢄꢀꢅꢈꢆ ꢀꢅ ꢂꢁw yꢀꢈꢂꢆ. iꢅ ꢃꢁꢅꢇꢉꢄsꢇ, diPe
Fꢀgꢋꢉꢈ 2. effꢈꢃꢇ ꢁf ꢈꢇhꢄꢅꢁꢂ/Fa mꢁꢂꢄꢉ ꢉꢄꢇꢀꢁ ꢁꢅ calB-ꢃꢄꢇꢄꢂyzꢈꢆ
syꢅꢇhꢈsꢀs ꢁf eF. rꢈꢄꢃꢇꢀꢁꢅ ꢃꢁꢅꢆꢀꢇꢀꢁꢅs: 10 mg/ml Fa; Sꢁꢂꢊꢈꢅꢇ:
ꢆꢀꢀsꢁpꢉꢁpyꢂ ꢈꢇhꢈꢉ (diPe); 100 mg/ml bꢀꢁꢃꢄꢇꢄꢂysꢇ (calB);
tꢈmpꢈꢉꢄꢇꢋꢉꢈ 60°c; rꢈꢄꢃꢇꢀꢁꢅ ꢇꢀmꢈ: 7 ꢆꢄys. cꢁꢅꢊꢈꢉsꢀꢁꢅ wꢄs
ꢆꢈꢇꢈꢉmꢀꢅꢈꢆ by HPlc.
(whꢁsꢈ sꢁꢂꢋbꢀꢂꢀꢇy ꢀꢅ wꢄꢇꢈꢉ ꢀs ꢂꢈss ꢇhꢄꢅ 2 g/l) ꢄꢂꢂꢁwꢈꢆ
ꢇhꢈ pꢉꢁꢆꢋꢃꢇꢀꢁꢅ ꢁf bꢁꢇh ꢈsꢇꢈꢉs 2 ꢄꢅꢆ 3 wꢀꢇh gꢁꢁꢆ
ꢃꢁꢅꢊꢈꢉsꢀꢁꢅ. Fꢁꢉ ꢇhꢀs ꢉꢈꢄsꢁꢅ, diPe wꢄs ꢇhꢈ sꢁꢂꢊꢈꢅꢇ ꢁf
ꢃhꢁꢀꢃꢈ ꢇꢁ ꢁpꢇꢀmꢀzꢈ ꢇhꢈ ꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢉꢈꢄꢃꢇꢀꢁꢅ.
iꢅ ꢇhꢀs ꢃꢁꢅꢇꢈxꢇ, ꢆꢀffꢈꢉꢈꢅꢇ sꢁꢂꢊꢈꢅꢇs hꢄꢊꢈ bꢈꢈꢅ
ꢉꢈpꢁꢉꢇꢈꢆ fꢁꢉ ꢇhꢈ ꢈꢅzymꢄꢇꢀꢃ ꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢁf hyꢆꢉꢁxy-
ꢃꢀꢅꢅꢄmꢀꢃ ꢄꢃꢀꢆs (cꢁmpꢇꢁꢅ ꢈꢇ ꢄꢂ. 2000), ꢀꢅꢃꢂꢋꢆꢀꢅg
mꢀxꢇꢋꢉꢈs ꢁf mꢀsꢃꢀbꢂꢈ sꢁꢂꢊꢈꢅꢇs sꢋꢃh ꢄs hꢈxꢄꢅꢈ/
bꢋꢇꢄꢅꢁꢅꢈ (Yꢄꢅg ꢈꢇ ꢄꢂ. 2012) ꢄꢅꢆ ꢀꢁꢅꢀꢃ ꢂꢀqꢋꢀꢆs
calB, diPe, ꢄꢅꢆ ꢄꢂꢃꢁhꢁꢂ/Fa 10). rꢈꢄꢃꢇꢀꢁꢅ yꢀꢈꢂꢆ
ꢆꢈꢃꢉꢈꢄsꢈꢆ fꢉꢁm 88.7% ꢄꢇ 60°c ꢇꢁ 12.2% ꢃꢁꢅꢊꢈꢉsꢀꢁꢅ
ꢄꢇ 30°c. thꢈ ꢁpꢇꢀmꢋm ꢇꢈmpꢈꢉꢄꢇꢋꢉꢈ fꢁꢉ ꢇhꢈ ꢉꢈꢄꢃꢇꢀꢁꢅ
wꢄs sꢈꢇ ꢇꢁ 60°c, whꢀꢃh ꢃꢁꢉꢉꢈꢂꢄꢇꢈs wꢈꢂꢂ wꢀꢇh ꢁꢇhꢈꢉ
bꢀꢁꢇꢉꢄꢅsfꢁꢉmꢄꢇꢀꢁꢅs ꢃꢄꢇꢄꢂyzꢈꢆ by ꢇhꢀs ꢀmmꢁbꢀꢂꢀzꢈꢆ
ꢈꢅzymꢈ (Sꢇꢈꢊꢈꢅsꢁꢅ ꢈꢇ ꢄꢂ. 2007) .
(Kꢄꢇsꢁꢋꢉꢄ ꢈꢇ ꢄꢂ. 2009ꢄ). iꢅ sꢁmꢈ ꢃꢄsꢈs, ꢇhꢈ ꢉꢈꢄꢃꢇꢀꢁꢅs
hꢄꢊꢈ bꢈꢈꢅ ꢃꢄꢉꢉꢀꢈꢆ ꢁꢋꢇ ꢋsꢀꢅg ꢇhꢈ ꢄꢂꢃꢁhꢁꢂ ꢃꢁmpꢁꢅꢈꢅꢇ
ꢄs ꢇhꢈ sꢁꢂꢊꢈꢅꢇ (Wꢈꢀꢇkꢄmp ꢈꢇ ꢄꢂ. 2006).
thꢈ ꢇꢀmꢈ ꢃꢁꢋꢉsꢈ ꢁf eF syꢅꢇhꢈsꢀs wꢄs sꢇꢋꢆꢀꢈꢆ ꢀꢅ
ꢆꢈꢇꢄꢀꢂ ꢋꢅꢆꢈꢉ ꢇhꢈ ꢁpꢇꢀmꢄꢂ ꢃꢁꢅꢆꢀꢇꢀꢁꢅs (Fꢀgꢋꢉꢈ 3). Wꢈ
ꢄꢃhꢀꢈꢊꢈꢆ ꢄꢅ ꢈffiꢃꢀꢈꢅꢇ ꢈꢅzymꢄꢇꢀꢃ syꢅꢇhꢈsꢀs ꢁf eF (93%
yꢀꢈꢂꢆ) by ꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢁf Fa wꢀꢇh ꢈꢇhꢄꢅꢁꢂ ꢃꢄꢇꢄꢂyzꢈꢆ
by calB, ꢀꢅ 7 ꢆꢄys. aꢂꢇhꢁꢋgh ꢇhꢈ ꢉꢈꢄꢃꢇꢀꢁꢅ wꢄs qꢋꢀꢇꢈ
sꢂꢁw ꢃꢁmpꢄꢉꢈꢆ wꢀꢇh ꢁꢇhꢈꢉ ꢂꢀpꢄsꢈ-ꢃꢄꢇꢄꢂyzꢈꢆ ꢈsꢇꢈꢉꢀfiꢃꢄ-
ꢇꢀꢁꢅs, ꢇhꢈ ꢉꢄꢇꢈ ꢄꢅꢆ pꢉꢁꢆꢋꢃꢇꢀꢊꢀꢇy wꢈꢉꢈ ꢅꢁꢇꢄbꢂy hꢀghꢈꢉ
ꢇhꢄꢅ ꢇhꢁsꢈ ꢉꢈpꢁꢉꢇꢈꢆ ꢀꢅ pꢉꢈꢊꢀꢁꢋs sꢇꢋꢆꢀꢈs. thꢋs,
cꢁmpꢇꢁꢅ ꢈꢇ ꢄꢂ. (2000) ꢉꢈꢄꢃhꢈꢆ ꢁꢅꢂy 20% ꢃꢁꢅꢊꢈꢉsꢀꢁꢅ
ꢁf eF ꢄꢅꢆ 14% ꢁꢃꢇyꢂ fꢈꢉꢋꢂꢄꢇꢈ ꢄfꢇꢈꢉ 12 ꢆꢄys ꢁf ꢉꢈꢄꢃ-
ꢇꢀꢁꢅ ꢀꢅ 2-mꢈꢇhyꢂ-2-pꢉꢁpꢄꢅꢁꢂ. Yꢄꢅg ꢈꢇ ꢄꢂ. (2012)
ꢁbꢇꢄꢀꢅꢈꢆ 5% ꢃꢁꢅꢊꢈꢉsꢀꢁꢅ ꢁf hꢈxyꢂ fꢈꢉꢋꢂꢄꢇꢈ ꢀꢅ 6 ꢆꢄys
ꢋsꢀꢅg sꢁꢂꢊꢈꢅꢇ mꢀxꢇꢋꢉꢈs ꢁf hꢈxꢄꢅꢈ ꢄꢅꢆ bꢋꢇꢄꢅꢁꢅꢈ.
Kꢄꢇsꢁꢋꢉꢄ ꢈꢇ ꢄꢂ. (2009ꢄ) ꢉꢈpꢁꢉꢇꢈꢆ 38.1% yꢀꢈꢂꢆ ꢁf
hꢈxyꢂ fꢈꢉꢋꢂꢄꢇꢈ ꢀꢅ 3 ꢆꢄys wꢀꢇh ꢄꢅ ꢀmmꢁbꢀꢂꢀzꢈꢆ ꢂꢀpꢄsꢈ
fꢉꢁm Mucor miehei (rMiM) ꢈmpꢂꢁyꢀꢅg ꢀꢁꢅꢀꢃ ꢂꢀqꢋꢀꢆs.
usꢀꢅg ꢅꢁꢅ-ꢈꢅzymꢄꢇꢀꢃ mꢈꢇhꢁꢆs, lꢀ ꢈꢇ ꢄꢂ. (2009b)
Effect of alcohol/ferulic acid ratio and the amount of
biocatalyst
thꢈ ꢀꢅflꢋꢈꢅꢃꢈ ꢁf ꢄꢂꢃꢁhꢁꢂ/Fa ꢉꢄꢇꢀꢁ ꢁꢅ ꢉꢈꢄꢃꢇꢀꢁꢅ yꢀꢈꢂꢆ
wꢄs ꢈꢊꢄꢂꢋꢄꢇꢈꢆ ꢀꢅ ꢇhꢈ ꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢁf Fa wꢀꢇh ꢈꢇhꢄꢅꢁꢂ
(eꢇoH) ꢄꢅꢆ ꢂꢄꢋꢉyꢂ ꢄꢂꢃꢁhꢁꢂ (lꢄꢋoH) ꢀꢅ diPe ꢋsꢀꢅg
calB ꢄs bꢀꢁꢃꢄꢇꢄꢂysꢇ. as ꢈxpꢈꢃꢇꢈꢆ, ꢀꢇ wꢄs ꢁbsꢈꢉꢊꢈꢆ
ꢇhꢄꢇ ꢄ mꢁꢂꢄꢉ ꢈxꢃꢈss ꢁf ꢄꢂꢃꢁhꢁꢂ wꢄs ꢄꢆꢊꢄꢅꢇꢄgꢈꢁꢋs fꢁꢉ
ꢇhꢈ ꢉꢈꢄꢃꢇꢀꢁꢅ, wꢀꢇh ꢄ mꢁꢂꢄꢉ ꢉꢄꢇꢀꢁ eꢇoH/Fa ꢁꢉ la/Fa
10:1 gꢀꢊꢀꢅg ꢇhꢈ bꢈsꢇ ꢉꢈsꢋꢂꢇs. a hꢀghꢈꢉ ꢈxꢃꢈss ꢁf ꢄꢂꢃꢁ-
hꢁꢂ ꢆꢀꢆ ꢅꢁꢇ ꢀmpꢉꢁꢊꢈ yꢀꢈꢂꢆs. Fꢀgꢋꢉꢈ 2 shꢁws ꢇhꢈ ꢉꢈsꢋꢂꢇs
fꢁꢉ ꢇhꢈ syꢅꢇhꢈsꢀs ꢁf eF (2) ꢄꢇ ꢆꢀffꢈꢉꢈꢅꢇ eꢇoH/Fa
mꢁꢂꢄꢉ ꢉꢄꢇꢀꢁs.
thꢈ ꢈffꢈꢃꢇ ꢁf ꢇhꢈ ꢄmꢁꢋꢅꢇ ꢁf bꢀꢁꢃꢄꢇꢄꢂysꢇ (ꢃꢁmpꢄꢉꢈꢆ
wꢀꢇh ꢇhꢈ ꢃꢁꢅꢃꢈꢅꢇꢉꢄꢇꢀꢁꢅ ꢁf Fa) wꢄs ꢄssꢈssꢈꢆ ꢀꢅ ꢇhꢈ
ꢈꢅzymꢄꢇꢀꢃ ꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢁf Fa wꢀꢇh ꢈꢇhꢄꢅꢁꢂ, ꢋsꢀꢅg
ꢄꢂꢃꢁhꢁꢂ/Fa mꢁꢂꢄꢉ ꢉꢄꢇꢀꢁ ꢁf 10, diPe ꢄs sꢁꢂꢊꢈꢅꢇ ꢄꢇ
60°c, ꢄꢅꢆ ꢊꢄꢉꢀꢄbꢂꢈ ꢄmꢁꢋꢅꢇs ꢁf calB. Fꢉꢁm ꢇhꢈ
tꢄbꢂꢈ ii. effꢈꢃꢇ ꢁf ꢇhꢈ bꢀꢁꢃꢄꢇꢄꢂysꢇ/Fa ꢉꢄꢇꢀꢁ (w/w) ꢀꢅ ꢇhꢈ ꢈꢅzymꢄꢇꢀꢃ
ꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢁf Fa wꢀꢇh ꢈꢇhꢄꢅꢁꢂ.
ꢉꢈsꢋꢂꢇs ꢁbꢇꢄꢀꢅꢈꢆ ꢄfꢇꢈꢉ 7 ꢆꢄys ꢁf ꢉꢈꢄꢃꢇꢀꢁꢅ (tꢄbꢂꢈ ii), ꢀꢇ
ꢃꢄꢅ bꢈ ꢃꢁꢅꢃꢂꢋꢆꢈꢆ ꢇhꢄꢇ ꢋsꢀꢅg 10 mg/ml ꢁf Fa, ꢇhꢈ
Bꢀꢁꢃꢄꢇꢄꢂysꢇ/Fa (w/w)
cꢁꢅꢊꢈꢉsꢀꢁꢅ (%)
ꢁ
pꢇꢀmꢋm bꢀꢁꢃꢄꢇꢄꢂysꢇ ꢃꢁꢅꢃꢈꢅꢇꢉꢄꢇꢀꢁꢅ wꢄs 100 mg/ml.
5
29.7
88.7
77.2
72.4
1
2
3
0
0
0
Effect of temperature and reaction time
thꢈ ꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢁf Fa wꢀꢇh ꢈꢇhꢄꢅꢁꢂ wꢄs ꢃꢄꢉꢉꢀꢈꢆ ꢁꢋꢇ
bꢈꢇwꢈꢈꢅ 30°c ꢄꢅꢆ 60°c.thꢈ ꢁꢇhꢈꢉ ꢉꢈꢄꢃꢇꢀꢁꢅ pꢄꢉꢄm-
ꢈꢇꢈꢉs wꢈꢉꢈ sꢈꢇ ꢄꢇ ꢇhꢈꢀꢉ ꢁpꢇꢀmꢄꢂ ꢊꢄꢂꢋꢈs (100 mg/ml ꢁf
expꢈꢉꢀmꢈꢅꢇꢄꢂ ꢃꢁꢅꢆꢀꢇꢀꢁꢅs: 10 mg/ml Fa; Mꢁꢂꢄꢉ ꢉꢄꢇꢀꢁ eꢇoH/Fa
0/1; eꢅzymꢈ: calB; 60°c; rꢈꢄꢃꢇꢀꢁꢅ ꢇꢀmꢈ: 7 ꢆꢄys. cꢁꢅꢊꢈꢉsꢀꢁꢅ
wꢄs ꢆꢈꢇꢈꢉmꢀꢅꢈꢆ by HPlc.
1

6
G. Sandoval et al.
(
Fꢈꢉꢉꢈꢉ ꢈꢇ ꢄꢂ. 2000; Kꢄꢉmꢈꢈ 2009; Pꢂꢁꢋ ꢈꢇ ꢄꢂ. 1999;
rꢈyꢈs-dꢋꢄꢉꢇꢈ ꢈꢇ ꢄꢂ. 2005).
twꢁ ꢄꢃyꢂ ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs (4 ꢄꢅꢆ 5) wꢈꢉꢈ ꢁbꢇꢄꢀꢅꢈꢆ
ꢇhꢉꢁꢋgh ꢇꢉꢄꢅsꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢁf eF (2) wꢀꢇh ꢊꢀꢅyꢂ ꢄꢃꢈ-
ꢇꢄꢇꢈ ꢄꢅꢆ ꢊꢀꢅyꢂ ꢂꢄꢋꢉꢄꢇꢈ, ꢉꢈspꢈꢃꢇꢀꢊꢈꢂy. nꢁ ꢆꢀmꢈꢉs fꢉꢁm
ꢄꢋꢇꢁ-ꢃꢁꢅꢆꢈꢅsꢄꢇꢀꢁꢅ ꢁf eF wꢈꢉꢈ ꢁbsꢈꢉꢊꢈꢆ. thꢈ ꢉꢈꢄꢃ-
ꢇꢀꢁꢅ wꢄs ꢈxꢄmꢀꢅꢈꢆ ꢋsꢀꢅg ꢆꢀffꢈꢉꢈꢅꢇ ꢀmmꢁbꢀꢂꢀzꢈꢆ
ꢂꢀpꢄsꢈs ꢄs ꢆꢈsꢃꢉꢀbꢈꢆ ꢀꢅ ꢇhꢈ “esꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢁf fꢈꢉꢋꢂꢀꢃ
ꢄꢃꢀꢆ” sꢈꢃꢇꢀꢁꢅ. amꢁꢅg ꢇhꢈm, ꢇhꢈ ꢀmmꢁbꢀꢂꢀzꢈꢆ ꢂꢀpꢄsꢈ
fꢉꢁm Alcaligenes sp. (QlG) gꢄꢊꢈ ꢇhꢈ mꢁsꢇ sꢄꢇꢀsfꢄꢃꢇꢁꢉy
ꢉꢈsꢋꢂꢇs ꢀꢅ ꢇhꢈ ꢄꢃꢈꢇyꢂꢄꢇꢀꢁꢅ ꢁf eF ꢇꢁ ꢄffꢁꢉꢆ 4, ꢄꢅꢆ
calB wꢄs mꢁsꢇ ꢈffiꢃꢀꢈꢅꢇ whꢈꢅ ꢊꢀꢅyꢂ ꢂꢄꢋꢉꢄꢇꢈ wꢄs
ꢋsꢈꢆ ꢇꢁ ꢁbꢇꢄꢀꢅ 5. iꢅ ꢇhꢈ ꢄbsꢈꢅꢃꢈ ꢁf ꢈꢅzymꢈs, eF ꢆꢀꢆ
ꢅꢁꢇ ꢉꢈꢄꢃꢇ ꢄꢇ ꢄꢂꢂ. Sꢁmꢈ ꢄꢋꢇhꢁꢉs hꢄꢊꢈ sꢋggꢈsꢇꢈꢆ ꢇhꢄꢇ
phꢈꢅꢁꢂꢀꢃ ꢄꢂꢃꢁhꢁꢂs ꢀꢅhꢀbꢀꢇ ꢂꢀpꢄsꢈs, ꢀꢅ pꢄꢉꢇꢀꢃꢋꢂꢄꢉ calB,
wꢀꢇh ꢀꢅhꢀbꢀꢇꢁꢉy ꢈffꢈꢃꢇs ꢄꢉꢀsꢀꢅg fꢉꢁm ꢈꢂꢈꢃꢇꢉꢁꢅꢀꢃ ꢉꢈsꢁ-
ꢅꢄꢅꢃꢈ bꢈꢇwꢈꢈꢅ ꢇhꢈ ꢆꢁꢋbꢂꢈ bꢁꢅꢆ ꢁꢅ ꢇhꢈ sꢀꢆꢈ ꢃhꢄꢀꢅ
ꢃꢁꢅjꢋgꢄꢇꢈꢆ wꢀꢇh ꢇhꢈ para-hyꢆꢉꢁxyꢂ gꢉꢁꢋp ꢀꢅ ꢃꢀꢅꢅꢄmꢀꢃ
ꢄꢃꢀꢆs (Gꢋyꢁꢇ ꢈꢇ ꢄꢂ. 1997; Sꢇꢈꢊꢈꢅsꢁꢅ ꢈꢇ ꢄꢂ. 2007).
Hꢁwꢈꢊꢈꢉ, ꢀꢅ ꢁꢋꢉ wꢁꢉk, C. antarctica B ꢄꢅꢆ Alcaligenes
sp. ꢂꢀpꢄsꢈs wꢈꢉꢈ ꢄbꢂꢈ ꢇꢁ ꢄꢃyꢂꢄꢇꢈ ꢇhꢈ phꢈꢅꢁꢂꢀꢃ oH ꢀꢅ
ꢇhꢈ para pꢁsꢀꢇꢀꢁꢅ ꢁf eF. calB wꢄs ꢄꢃꢇꢀꢊꢈ ꢀꢅ ꢇhꢈ
syꢅꢇhꢈsꢀs ꢁf bꢁꢇh ꢆꢀꢈsꢇꢈꢉs 4 ꢄꢅꢆ 5, bꢋꢇ QlG wꢄs
mꢁꢉꢈ ꢈffiꢃꢀꢈꢅꢇ ꢀꢅ ꢇhꢈ ꢃꢄsꢈ ꢁf 4. aꢂꢇhꢁꢋgh Alcaligenes
sp. ꢂꢀpꢄsꢈ ꢀs ꢇypꢀꢃꢄꢂꢂy ꢈmpꢂꢁyꢈꢆ ꢀꢅ ꢈꢅꢄꢅꢇꢀꢁsꢈꢂꢈꢃꢇꢀꢊꢈ
syꢅꢇhꢈsꢀs (chꢈꢅ ꢈꢇ ꢄꢂ. 2014), ꢀꢇ ꢀs ꢄꢂsꢁ ꢄbꢂꢈ ꢇꢁ ꢄꢃyꢂꢄꢇꢈ
ꢇhꢈ phꢈꢅꢁꢂꢀꢃ oH ꢀꢅ ꢇhꢈ para pꢁsꢀꢇꢀꢁꢅ (4′) ꢁf ꢄ ꢉꢈꢂꢄꢇꢈꢆ
sꢋbsꢇꢉꢄꢇꢈ (ꢉꢈsꢊꢈꢉꢄꢇꢉꢁꢂ) ꢋsꢀꢅg ꢊꢀꢅyꢂ ꢈsꢇꢈꢉs (tꢁꢉꢉꢈs ꢈꢇ ꢄꢂ.
Fꢀgꢋꢉꢈ 3. tꢀmꢈ ꢃꢁꢋꢉsꢈ ꢁf eF syꢅꢇhꢈsꢀs ꢀꢅ diPe ꢃꢄꢇꢄꢂyzꢈꢆ by
calB. rꢈꢄꢃꢇꢀꢁꢅ ꢃꢁꢅꢆꢀꢇꢀꢁꢅs: 10 mg/ml Fa; 100 mg/ml
bꢀꢁꢃꢄꢇꢄꢂysꢇ; tꢈmpꢈꢉꢄꢇꢋꢉꢈ 60°c. cꢁꢅꢊꢈꢉsꢀꢁꢅ wꢄs ꢆꢈꢇꢈꢉmꢀꢅꢈꢆ by
HPlc.
ꢆꢈsꢃꢉꢀbꢈꢆ ꢇhꢈ syꢅꢇhꢈsꢀs ꢁf eF ꢋsꢀꢅg 10% H So ꢄs
2
4
ꢃꢄꢇꢄꢂysꢇ ꢋꢅꢆꢈꢉ ꢉꢈflꢋx (8 h) ꢁꢉ mꢀꢃꢉꢁwꢄꢊꢈ ꢀꢉꢉꢄꢆꢀꢄꢇꢀꢁꢅ
3–5 mꢀꢅ), ꢉꢈpꢁꢉꢇꢀꢅg 81% ꢄꢅꢆ 95% yꢀꢈꢂꢆ, ꢉꢈspꢈꢃ-
(
ꢇꢀꢊꢈꢂy. Hꢁwꢈꢊꢈꢉ, ꢄꢂꢇhꢁꢋgh ꢇhꢈ pꢉꢁꢆꢋꢃꢇ wꢄs ꢁbꢇꢄꢀꢅꢈꢆ
wꢀꢇh hꢀgh ꢃꢁꢅꢊꢈꢉsꢀꢁꢅ ꢀꢅ ꢄ shꢁꢉꢇꢈꢉ ꢇꢀmꢈ ꢇhꢄꢅ ꢇhꢈ ꢈꢅzy-
mꢄꢇꢀꢃ pꢉꢁꢃꢈss, ꢇhꢈ ꢋsꢈ ꢁf ꢄ ꢃꢁꢉꢉꢁsꢀꢊꢈ sꢇꢉꢁꢅg mꢀꢅꢈꢉꢄꢂ
ꢄꢃꢀꢆ sꢋꢃh ꢄs sꢋꢂfꢋꢉꢀꢃ ꢄꢃꢀꢆ, ꢄꢇ hꢀgh ꢃꢁꢅꢃꢈꢅꢇꢉꢄꢇꢀꢁꢅ, ꢀs
ꢅꢁꢇ ꢈꢅꢊꢀꢉꢁꢅmꢈꢅꢇꢄꢂꢂy fꢉꢀꢈꢅꢆꢂy.
thꢈ ꢁpꢇꢀmꢄꢂ ꢃꢁꢅꢆꢀꢇꢀꢁꢅs fꢁꢉ ꢇhꢈ ꢈꢅzymꢄꢇꢀꢃ ꢈsꢇꢈꢉꢀ-
fiꢃꢄꢇꢀꢁꢅ ꢁf Fa wꢀꢇh ꢈꢇhꢄꢅꢁꢂ wꢈꢉꢈ ꢄs fꢁꢂꢂꢁws: calB
bꢀꢁꢃꢄꢇꢄꢂysꢇ, ꢄꢂꢃꢁhꢁꢂ/Fa mꢁꢂꢄꢉ ꢉꢄꢇꢀꢁ 10, ꢈꢅzymꢈ/Fa
wꢈꢀghꢇ ꢉꢄꢇꢀꢁ 10, diPe ꢄs sꢁꢂꢊꢈꢅꢇ, 60°c, ꢄꢅꢆ 7-ꢆꢄy
ꢉꢈꢄꢃꢇꢀꢁꢅ ꢇꢀmꢈ.
iꢅ ꢇhꢈ ꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢁf Fa wꢀꢇh ꢆꢁꢆꢈꢃyꢂ ꢄꢂꢃꢁhꢁꢂ,
ꢇhꢈ yꢀꢈꢂꢆ ꢁf lF wꢄs 85% ꢄfꢇꢈꢉ 200 h, whꢀꢃh wꢄs ꢄ
hꢀghꢈꢉ yꢀꢈꢂꢆ ꢇhꢄꢅ ꢇhꢄꢇ ꢄꢃhꢀꢈꢊꢈꢆ ꢀꢅ ꢄ pꢉꢈꢊꢀꢁꢋs ꢃhꢈmꢀꢃꢄꢂ
syꢅꢇhꢈsꢀs (72%) ꢋsꢀꢅg p-ꢇꢁꢂꢋꢈꢅꢈsꢋꢂfꢁꢅꢀꢃ ꢄꢃꢀꢆ ꢄs
ꢃꢄꢇꢄꢂysꢇ (tꢄꢅꢀgꢋꢃhꢀ ꢈꢇ ꢄꢂ. 1999).
2
012).
-aꢃꢈꢇꢁxy-ꢈꢇhyꢂ fꢈꢉꢋꢂꢄꢇꢈ (4) wꢄs ꢋꢅꢈqꢋꢀꢊꢁꢃꢄꢂꢂy
ꢆꢈꢅꢇꢀfiꢈꢆ by nMr ꢄꢅꢆ MS.thꢈ mꢁꢂꢈꢃꢋꢂꢄꢉ fꢁꢉmꢋꢂꢄ
wꢄs ꢆꢈꢇꢈꢉmꢀꢅꢈꢆ ꢄs c H o , ꢁꢅ ꢇhꢈ bꢄsꢀs ꢁf ꢇhꢈ
4
ꢀ
1
4
16
5
Hr-eSi-MS. thꢈ mꢁꢂꢈꢃꢋꢂꢄꢉ ꢀꢁꢅ wꢄs 42 dꢄ ꢂꢄꢉgꢈꢉ
ꢇhꢄꢅ eF, ꢀꢅꢆꢀꢃꢄꢇꢀꢅg ꢇhꢈ ꢄꢆꢆꢀꢇꢀꢁꢅ ꢁf ꢇhꢈ ꢄꢃꢈꢇꢄꢇꢈ ꢇꢁ ꢇhꢈ
1
hyꢆꢉꢁxyꢂ gꢉꢁꢋp. thꢈ H nMr spꢈꢃꢇꢉꢋm ꢁf 4 ꢈxhꢀb-
ꢀ
ꢇꢈꢆ ꢄ ꢅꢈw sꢀgꢅꢄꢂ ꢃꢁꢉꢉꢈspꢁꢅꢆꢀꢅg ꢇꢁ ꢇhꢈ mꢈꢇhyꢂ gꢉꢁꢋp
13
ꢀꢅ ꢄꢃꢈꢇꢄꢇꢈ ꢄꢇ d 2.32, ꢄꢅꢆ c nMr shꢁwꢈꢆ ꢄ ꢅꢈw
sꢀgꢅꢄꢂ ꢄꢇ d 168.8 ꢃꢁꢉꢉꢈspꢁꢅꢆꢀꢅg ꢇꢁ ꢇhꢈ ꢃꢄꢉbꢁꢅyꢂ ꢃꢄꢉ-
bꢁꢅ ꢀꢅ ꢄꢃꢈꢇꢄꢇꢈ. tꢄꢅg & Xꢀꢁꢅg (2011) ꢆꢈsꢃꢉꢀbꢈꢆ ꢇhꢈ
syꢅꢇhꢈsꢀs ꢁf 4 by ꢃhꢈmꢀꢃꢄꢂ ꢄꢃꢈꢇyꢂꢄꢇꢀꢁꢅ ꢁf eF wꢀꢇh
ꢄꢃꢈꢇꢀꢃ ꢄꢅhyꢆꢉꢀꢆꢈ fꢁꢉ ꢀꢇs ꢋsꢈ ꢀꢅ ꢇhꢈ ꢇꢉꢈꢄꢇmꢈꢅꢇ ꢁf ꢊꢄs-
ꢃꢋꢂꢄꢉ ꢆꢀsꢈꢄsꢈs.
Acylation of ethyl ferulate acid by transesterification
thꢈ ꢄꢃyꢂꢄꢇꢀꢁꢅ ꢁf ꢇhꢈ fꢉꢈꢈ phꢈꢅꢁꢂꢀꢃ gꢉꢁꢋp ꢀꢅ eF ꢃꢁꢋꢂꢆ
ꢂꢈꢄꢆ ꢇꢁ ꢂꢀpꢁphꢀꢂꢀꢃ ꢆꢀꢈsꢇꢈꢉs wꢀꢇh ꢈꢅhꢄꢅꢃꢈꢆ hyꢆꢉꢁphꢁ-
bꢀꢃꢀꢇy. iꢅ ꢊꢀꢈw ꢁf ꢁꢋꢉ pꢉꢈꢊꢀꢁꢋs wꢁꢉk ꢁꢅ ꢈꢅzymꢄꢇꢀꢃ
ꢄꢃyꢂꢄꢇꢀꢁꢅ ꢁf ꢅꢄꢇꢋꢉꢄꢂ phꢈꢅꢁꢂꢀꢃ ꢄꢅꢇꢀꢁxꢀꢆꢄꢅꢇs sꢋꢃh ꢄs
ꢊꢀꢇꢄmꢀꢅ e (tꢁꢉꢉꢈs ꢈꢇ ꢄꢂ. 2008) ꢄꢅꢆ ꢉꢈsꢊꢈꢉꢄꢇꢉꢁꢂ (tꢁꢉ-
ꢉꢈs ꢈꢇ ꢄꢂ. 2010), wꢈ ꢆꢈꢃꢀꢆꢈꢆ ꢇꢁ ꢀꢅꢊꢈsꢇꢀgꢄꢇꢈ ꢇhꢈ ꢄꢃyꢂꢄ-
ꢇꢀꢁꢅ ꢁf ꢇhꢈ 4-oH ꢁf eF, ꢋsꢀꢅg ꢆꢀffꢈꢉꢈꢅꢇ ꢊꢀꢅyꢂ ꢈsꢇꢈꢉs
ꢄs ꢄꢃyꢂꢄꢇꢀꢅg ꢄgꢈꢅꢇs.Wꢈ sꢈꢂꢈꢃꢇꢈꢆ ꢇwꢁ ꢃhꢄꢀꢅs ꢁf ꢆꢀffꢈꢉ-
ꢈꢅꢇ ꢂꢈꢅgꢇhs (c2 ꢄꢅꢆ c12) ꢀꢅ ꢁꢉꢆꢈꢉ ꢇꢁ ꢃꢁꢊꢈꢉ ꢄ bꢉꢁꢄꢆ
ꢉꢄꢅgꢈ ꢁf ꢂꢀpꢁphꢀꢂꢀꢃꢀꢇy. iꢇ hꢄs bꢈꢈꢅ shꢁwꢅ ꢇhꢄꢇ ꢇhꢈ
ꢉꢈꢄꢃꢇꢀꢊꢀꢇy ꢁf ꢊꢀꢅyꢂ ꢈsꢇꢈꢉs ꢄꢅꢆ ꢇhꢈ ꢇꢄꢋꢇꢁmꢈꢉꢀzꢄꢇꢀꢁꢅ ꢁf
ꢊꢀꢅyꢂ ꢄꢂꢃꢁhꢁꢂ ꢇꢁ ꢊꢁꢂꢄꢇꢀꢂꢈ ꢄꢃꢈꢇꢄꢂꢆꢈhyꢆꢈ ꢀmpꢉꢁꢊꢈ ꢉꢈꢄꢃꢇꢀꢁꢅ
ꢉꢄꢇꢈs ꢄꢅꢆ ꢃꢁꢅꢊꢈꢉsꢀꢁꢅ ꢀꢅ ꢂꢀpꢄsꢈ-ꢃꢄꢇꢄꢂyzꢈꢆ ꢄꢃyꢂꢄꢇꢀꢁꢅs
tꢁ ꢇhꢈ bꢈsꢇ ꢁf ꢁꢋꢉ kꢅꢁwꢂꢈꢆgꢈ, ꢇhꢈ pꢉꢁꢆꢋꢃꢇ 5 [(E)-
eꢇhyꢂ 3-(4-ꢆꢁꢆꢈꢃꢄꢅꢁyꢂꢁxy-3-mꢈꢇhꢁxyphꢈꢅyꢂ)-pꢉꢁp-
2-ꢈꢅꢁꢄꢇꢈ] ꢀs ꢄ ꢅꢈw ꢃꢁmpꢁꢋꢅꢆ. iꢇ ꢀs ꢄ whꢀꢇꢈ sꢁꢂꢀꢆ wꢀꢇh
ꢂꢁw mꢈꢂꢇꢀꢅg pꢁꢀꢅꢇ (34–35°c) ꢄꢅꢆ hꢄs bꢈꢈꢅ ꢃꢁm-
pꢂꢈꢇꢈꢂy ꢃhꢄꢉꢄꢃꢇꢈꢉꢀzꢈꢆ by spꢈꢃꢇꢉꢁsꢃꢁpꢀꢃ mꢈꢇhꢁꢆs.thꢈ
ꢄbsꢈꢅꢃꢈ ꢁf ꢇhꢈ sꢀgꢅꢄꢂ ꢄꢇ ꢄbꢁꢋꢇ 3400 ꢃm ꢀꢅ ꢇhꢈ
Ftir spꢈꢃꢇꢉꢋm ꢀꢅꢆꢀꢃꢄꢇꢈs ꢄꢃyꢂꢄꢇꢀꢁꢅ ꢁf ꢇhꢈ phꢈꢅꢁꢂ
hyꢆꢉꢁxyꢂ gꢉꢁꢋp ꢀꢅ eF. iꢅ ꢇhꢈ MS spꢈꢃꢇꢉꢋm, ꢇhꢈ
mꢁꢂꢈꢃꢋꢂꢄꢉ ꢀꢁꢅ wꢄs 182 dꢄ ꢂꢄꢉgꢈꢉ ꢇhꢄꢅ eF, whꢀꢃh
ꢀꢅꢆꢀꢃꢄꢇꢈꢆ ꢇhꢈ fꢁꢉmꢄꢇꢀꢁꢅ ꢁf ꢇhꢈ ꢂꢄꢋꢉyꢂ ꢈsꢇꢈꢉ ꢁꢅ ꢇhꢈ
phꢈꢅꢁꢂꢀꢃ gꢉꢁꢋp ꢁf ꢇhꢈ sꢋbsꢇꢉꢄꢇꢈ ꢄꢅꢆ wꢄs ꢀꢅ ꢄꢃꢃꢁꢉ-
ꢆꢄꢅꢃꢈ wꢀꢇh ꢇhꢈ mꢁꢂꢈꢃꢋꢂꢄꢉ fꢁꢉmꢋꢂꢄ c H o , ꢁꢅ ꢇhꢈ
1
2
4
36
5
1
bꢄsꢀs ꢁf ꢇhꢈ Hr-eSi-MS. H nMr spꢈꢃꢇꢉꢋm shꢁwꢈꢆ

Ferulic acid esterification
7
sꢀgꢅꢄꢂs ꢃꢁꢉꢉꢈspꢁꢅꢆꢀꢅg ꢇꢁ ꢇhꢈ ꢂꢄꢋꢉyꢂ ꢃhꢄꢀꢅ ꢄꢇ d 0.88,
.26–1.33, 1.63, 1.76, ꢄꢅꢆ 2.58, ꢄꢅꢆ 1 c nMr spꢈꢃ-
3
1
ꢇꢉꢋm shꢁwꢈꢆ ꢄ sꢀgꢅꢄꢂ ꢄꢇ d 171.7 ꢃꢁꢉꢉꢈspꢁꢅꢆꢀꢅg ꢇꢁ
ꢇhꢈ ꢃꢄꢉbꢁꢅyꢂ ꢃꢄꢉbꢁꢅ ꢀꢅ ꢂꢄꢋꢉyꢂ gꢉꢁꢋp.
Optimal conditions of enzymatic transesterification
Wꢈ ꢄꢅꢄꢂyzꢈꢆ ꢇhꢈ ꢈffꢈꢃꢇ ꢁf sꢈꢊꢈꢉꢄꢂ ꢉꢈꢄꢃꢇꢀꢁꢅ pꢄꢉꢄmꢈꢇꢈꢉs
ꢁ
ꢁ
2
ꢅ ꢇhꢈ fꢁꢉmꢄꢇꢀꢁꢅ ꢁf Fa ꢆꢀꢈsꢇꢈꢉs fꢁꢂꢂꢁwꢀꢅg ꢇhꢈ mꢈꢇh-
ꢆꢁꢂꢁgy ꢆꢈsꢃꢉꢀbꢈꢆ fꢁꢉ ꢇhꢈ syꢅꢇhꢈsꢀs ꢁf mꢁꢅꢁꢈsꢇꢈꢉs
ꢄꢅꢆ 3. agꢄꢀꢅ, 60°c wꢄs ꢇhꢈ ꢁpꢇꢀmꢋm ꢇꢈmpꢈꢉꢄꢇꢋꢉꢈ,
wꢀꢇh ꢅꢈgꢂꢀgꢀbꢂꢈ ꢃꢁꢅꢊꢈꢉsꢀꢁꢅ ꢄꢇ 30°c. By ꢊꢄꢉyꢀꢅg ꢇhꢈ
ꢄmꢁꢋꢅꢇ ꢁf bꢀꢁꢃꢄꢇꢄꢂysꢇ ꢉꢈꢂꢄꢇꢀꢊꢈ ꢇꢁ ꢇhꢈ ꢃꢁꢅꢃꢈꢅꢇꢉꢄꢇꢀꢁꢅ
ꢁf eF, ꢋsꢀꢅg ꢉꢄꢇꢀꢁs fꢉꢁm 5 ꢇꢁ 30 wꢈ fꢁꢋꢅꢆ ꢇhꢄꢇ ꢄ
bꢀꢁꢃꢄꢇꢄꢂysꢇ/eF wꢈꢀghꢇ ꢉꢄꢇꢀꢁ ꢁf 10 gꢄꢊꢈ ꢇhꢈ bꢈsꢇ ꢉꢈsꢋꢂꢇs
fꢁꢉ QlG ꢄꢅꢆ calB. thꢈ ꢁꢉgꢄꢅꢀꢃ sꢁꢂꢊꢈꢅꢇ ꢈxꢈꢉꢇꢈꢆ
sꢋbsꢇꢄꢅꢇꢀꢄꢂ ꢀꢅflꢋꢈꢅꢃꢈ ꢁꢅ ꢇhꢈ ꢉꢈꢄꢃꢇꢀꢁꢅ yꢀꢈꢂꢆ wꢀꢇh
diPe, ꢄgꢄꢀꢅ, bꢈꢀꢅg ꢇhꢈ bꢈsꢇ ꢉꢈꢄꢃꢇꢀꢁꢅ mꢈꢆꢀꢋm fꢁꢉ
ꢇhꢈ ꢇꢉꢄꢅsꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅs, ꢉꢈpꢉꢈsꢈꢅꢇꢀꢅg ꢄ ꢃꢁmpꢉꢁmꢀsꢈ
bꢈꢇwꢈꢈꢅ sꢋbsꢇꢉꢄꢇꢈ sꢁꢂꢋbꢀꢂꢀꢇy ꢄꢅꢆ ꢈꢅzymꢈ ꢄꢃꢇꢀꢊꢀꢇy/
sꢇꢄbꢀꢂꢀꢇy. aꢅ ꢄꢃyꢂ ꢆꢁꢅꢁꢉ/eF mꢁꢂꢄꢉ ꢉꢄꢇꢀꢁ ꢁf 2 gꢄꢊꢈ ꢇhꢈ
hꢀghꢈsꢇ yꢀꢈꢂꢆs. iꢅ sꢋmmꢄꢉy, wꢈ hꢄꢊꢈ ꢆꢈfiꢅꢈꢆ ꢇhꢈ
fꢁꢂꢂꢁwꢀꢅg sꢇꢄꢅꢆꢄꢉꢆ ꢃꢁꢅꢆꢀꢇꢀꢁꢅs fꢁꢉ ꢇhꢈ bꢀꢁꢃꢄꢇꢄꢂyꢇꢀꢃ
ꢇꢉꢄꢅsꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ bꢈꢇwꢈꢈꢅ eF ꢄꢅꢆ ꢊꢀꢅyꢂ ꢄꢃꢈꢇꢄꢇꢈ ꢁꢉ
ꢂꢄꢋꢉꢄꢇꢈ: QlG (fꢁꢉ 4) ꢄꢅꢆ calB (fꢁꢉ 5) ꢄs bꢀꢁꢃꢄꢇꢄ-
ꢂysꢇs, diPe ꢄs sꢁꢂꢊꢈꢅꢇ, ꢊꢀꢅyꢂ ꢈsꢇꢈꢉ/eF2, bꢀꢁꢃꢄꢇꢄꢂysꢇ/
eF10, ꢄꢅꢆ 60°c. afꢇꢈꢉ 72 h ꢁf ꢉꢈꢄꢃꢇꢀꢁꢅ, ꢇhꢈ ꢃꢁm-
pꢁꢋꢅꢆ 4 wꢄs ꢁbꢇꢄꢀꢅꢈꢆ ꢀꢅ 59% yꢀꢈꢂꢆ ꢄꢅꢆ ꢇhꢈ ꢆꢀꢈsꢇꢈꢉ
Fꢀgꢋꢉꢈ 4. aꢅꢇꢀ-ꢀꢅflꢄmmꢄꢇꢁꢉy ꢄꢃꢇꢀꢊꢀꢇy ꢁf Fa ꢄꢅꢆ ꢀꢇs ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs,
mꢈꢄsꢋꢉꢈꢆ ꢄs ꢀꢅhꢀbꢀꢇꢀꢁꢅ ꢁf coX-2 in vitro. cꢁꢅꢃꢈꢅꢇꢉꢄꢇꢀꢁꢅs ꢇꢈsꢇꢈꢆ:
dꢀꢃꢂꢁfꢈꢅꢄꢃ (d), 0.1 M; Fa ꢄꢅꢆ ꢀꢇs mꢁꢅꢁ- ꢄꢅꢆ ꢆꢀꢈsꢇꢈꢉs, 1.0 M.
ꢄꢃꢇꢀꢊꢈ ꢇhꢄꢅ 2 ꢄꢅꢆ 4 ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs, whꢀꢃh hꢄꢊꢈ ꢁꢅꢂy shꢁꢉꢇ
ꢄꢂkyꢂꢀꢃ ꢃhꢄꢀꢅs.thꢈsꢈ pꢉꢈꢂꢀmꢀꢅꢄꢉy ꢉꢈsꢋꢂꢇs ꢀꢅꢆꢀꢃꢄꢇꢈ ꢇhꢄꢇ
Fa wꢀꢇh ꢂꢁꢅg ꢄꢂkyꢂ ꢁꢉ ꢄꢃyꢂ ꢃhꢄꢀꢅs ꢀꢅhꢀbꢀꢇꢈꢆ coX-2
mꢁꢉꢈ sꢇꢉꢁꢅgꢂy ꢇhꢄꢅ Fa (1). Hꢁwꢈꢊꢈꢉ, fꢋꢉꢇhꢈꢉ ꢈxpꢈꢉ-
ꢀmꢈꢅꢇs ꢄꢉꢈ ꢅꢈꢈꢆꢈꢆ ꢇꢁ ꢈꢊꢄꢂꢋꢄꢇꢈ ꢇhꢈ pꢁꢇꢈꢅꢇꢀꢄꢂ ꢁf Fa
ꢈsꢇꢈꢉs ꢀꢅ ꢄꢅꢇꢀ-ꢀꢅflꢄmmꢄꢇꢁꢉy pꢉꢈpꢄꢉꢄꢇꢀꢁꢅs. aꢂꢇhꢁꢋgh
hꢈpꢄꢇꢁꢇꢁxꢀꢃꢀꢇy ꢁf ꢅꢈw ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs hꢄs ꢅꢁꢇ bꢈꢈꢅ ꢇꢈsꢇꢈꢆ,
ꢀꢇ ꢀs ꢉꢈꢄsꢁꢅꢄbꢂꢈ ꢇꢁ ꢄssꢋmꢈ ꢇhꢄꢇ ꢇhꢈy ꢄꢉꢈ ꢅꢁꢇ ꢇꢁxꢀꢃ,
bꢈꢃꢄꢋsꢈ Fa ꢄꢅꢆ eF hꢄꢊꢈ bꢈꢈꢅ ꢉꢈpꢁꢉꢇꢈꢆ ꢇꢁ ꢄꢂꢂꢈꢊꢀꢄꢇꢈ
ꢀꢅꢆꢋꢃꢈꢆ ꢂꢀꢊꢈꢉ ꢆꢄmꢄgꢈ ꢄꢅꢆ ꢂꢀꢊꢈꢉ ꢃꢄꢅꢃꢈꢉ (lꢈꢈ 2005).
5
wꢄs ꢁbꢇꢄꢀꢅꢈꢆ ꢀꢅ 52% yꢀꢈꢂꢆ.
Anti-inflammatory activity of the derivatives
Conclusions
thꢈ ꢀꢅhꢀbꢀꢇꢀꢁꢅ ꢁf ꢇhꢈ ꢈꢅzymꢈs coX-1 ꢄꢅꢆ coX-2
iꢅ ꢇhꢀs wꢁꢉk wꢈ hꢄꢊꢈ ꢆꢈsꢃꢉꢀbꢈꢆ ꢄꢅ ꢈffiꢃꢀꢈꢅꢇ ꢈꢅzymꢄꢇꢀꢃ
syꢅꢇhꢈsꢀs ꢁf ꢇwꢁ mꢁꢅꢁꢈsꢇꢈꢉs ꢄꢅꢆ ꢇwꢁ ꢆꢀꢈsꢇꢈꢉs ꢁf Fa.
thꢈ Fa mꢁꢅꢁꢈsꢇꢈꢉs wꢈꢉꢈ ꢁbꢇꢄꢀꢅꢈꢆ ꢀꢅ hꢀghꢈꢉ yꢀꢈꢂꢆ
ꢄꢅꢆ ꢀꢅ ꢄ shꢁꢉꢇꢈꢉ ꢇꢀmꢈ ꢇhꢄꢅ ꢀꢅ pꢉꢈꢊꢀꢁꢋs ꢉꢈpꢁꢉꢇs ꢋsꢀꢅg
bꢀꢁꢃꢄꢇꢄꢂysꢇs. oꢅꢈ ꢁf ꢇhꢈ syꢅꢇhꢈsꢀzꢈꢆ ꢆꢀꢈsꢇꢈꢉs ꢀs ꢄ ꢅꢈw
ꢃꢁmpꢁꢋꢅꢆ. Wꢀꢇh ꢉꢈspꢈꢃꢇ ꢇꢁ Fa, ꢇhꢈ ꢂꢀpꢁphꢀꢂꢀꢃꢀꢇy ꢁf
ꢇhꢈ syꢅꢇhꢈsꢀzꢈꢆ ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs wꢄs ꢀꢅꢃꢉꢈꢄsꢈꢆ ꢇꢁ ꢆꢀffꢈꢉꢈꢅꢇ
ꢆꢈgꢉꢈꢈs, whꢀꢃh mꢄy mꢁꢆꢋꢂꢄꢇꢈ ꢇhꢈꢀꢉ bꢈhꢄꢊꢀꢁꢉ ꢀꢅ ꢈmꢋꢂ-
sꢀfiꢈꢆ sysꢇꢈms, sꢇꢄbꢀꢂꢀꢇy, ꢄꢅꢆ bꢀꢁꢄꢊꢄꢀꢂꢄbꢀꢂꢀꢇy. Fꢁꢉ ꢇhꢄꢇ
ꢉꢈꢄsꢁꢅ, ꢇhꢈ Fa mꢁꢅꢁ- ꢄꢅꢆ ꢆꢀꢈsꢇꢈꢉs hꢈꢉꢈ ꢆꢈsꢃꢉꢀbꢈꢆ
mꢄy bꢈ ꢋsꢈfꢋꢂ ꢀꢅ ꢇhꢈ fꢁꢁꢆ, phꢄꢉmꢄꢃꢈꢋꢇꢀꢃꢄꢂ, ꢄꢅꢆ ꢃꢁs-
mꢈꢇꢀꢃ ꢀꢅꢆꢋsꢇꢉꢀꢈs. as ꢄ pꢉꢁꢁf ꢁf ꢃꢁꢅꢃꢈpꢇ, ꢂꢁꢅg-ꢃhꢄꢀꢅ
ꢈsꢇꢈꢉs ꢁf Fa ꢈxhꢀbꢀꢇꢈꢆ bꢈꢇꢇꢈꢉ ꢄꢅꢇꢀ-ꢀꢅflꢄmmꢄꢇꢁꢉy ꢄꢃꢇꢀꢊ-
ꢀꢇy ꢇhꢄꢅ ꢇhꢈꢀꢉ ꢃꢁꢉꢉꢈspꢁꢅꢆꢀꢅg shꢁꢉꢇ-ꢃhꢄꢀꢅ ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs.
ꢀs ꢃꢁꢅsꢀꢆꢈꢉꢈꢆ ꢁꢅꢈ ꢁf ꢇhꢈ mꢈꢃhꢄꢅꢀsms ꢁf ꢄꢅꢇꢀ-ꢀꢅflꢄm-
mꢄꢇꢁꢉy ꢄꢃꢇꢀꢁꢅ. coX ꢈꢅzymꢈs ꢄꢉꢈ ꢀꢅꢊꢁꢂꢊꢈꢆ ꢀꢅ ꢇhꢈ
bꢀꢁsyꢅꢇhꢈsꢀs ꢁf pꢉꢁsꢇꢄgꢂꢄꢅꢆꢀꢅs, ꢇhꢉꢁmbꢁxꢄꢅꢈs, ꢄꢅꢆ
pꢉꢁsꢇꢄꢃyꢃꢂꢀꢅs. iꢅ pꢄꢉꢇꢀꢃꢋꢂꢄꢉ, coX-2 ꢀs ꢉꢈspꢁꢅsꢀbꢂꢈ fꢁꢉ
ꢇhꢈ bꢀꢁsyꢅꢇhꢈsꢀs ꢁf pꢉꢁsꢇꢄgꢂꢄꢅꢆꢀꢅs ꢋꢅꢆꢈꢉ ꢄꢃꢋꢇꢈ
ꢀꢅflꢄmmꢄꢇꢁꢉy ꢃꢁꢅꢆꢀꢇꢀꢁꢅs. thꢈ pꢉꢁꢆꢋꢃꢇs 2–5 wꢈꢉꢈ
ꢈꢊꢄꢂꢋꢄꢇꢈꢆ ꢄs ꢀꢅhꢀbꢀꢇꢁꢉs ꢁf coX-2 ꢋsꢀꢅg ꢄ coX-ꢀꢅ-
hꢀbꢀꢇꢁꢉ sꢃꢉꢈꢈꢅꢀꢅg ꢄssꢄy kꢀꢇ. Fa (1) wꢄs ꢄꢂsꢁ ꢄssꢄyꢈꢆ
ꢄs ꢄ ꢃꢁꢅꢇꢉꢁꢂ. thꢈ kꢀꢇ mꢈꢄsꢋꢉꢈs pꢉꢁsꢇꢄꢅꢁꢀꢆ pꢉꢁꢆꢋꢃꢇs
ꢁf ꢇhꢈ coX-2 ꢉꢈꢄꢃꢇꢀꢁꢅ ꢊꢀꢄ ꢈꢅzymꢈ ꢀmmꢋꢅꢁꢄssꢄy,
ꢋsꢀꢅg ꢄ bꢉꢁꢄꢆ spꢈꢃꢀfiꢃꢀꢇy ꢄꢅꢇꢀsꢈꢉꢋm ꢇhꢄꢇ bꢀꢅꢆs ꢇꢁ ꢄꢂꢂ
ꢇhꢈ mꢄjꢁꢉ pꢉꢁsꢇꢄgꢂꢄꢅꢆꢀꢅ ꢃꢁmpꢁꢋꢅꢆs (Pꢉꢄꢆꢈꢂꢂꢈs ꢈꢇ ꢄꢂ.
1985). dꢀꢃꢂꢁfꢈꢅꢄꢃ, ꢄ wꢈꢂꢂ-kꢅꢁwꢅ ꢅꢁꢅ-sꢇꢈꢉꢁꢀꢆꢄꢂ ꢄꢅꢇꢀ-
ꢀꢅflꢄmmꢄꢇꢁꢉy ꢆꢉꢋg, wꢄs ꢋsꢈꢆ ꢄs ꢉꢈfꢈꢉꢈꢅꢃꢈ sꢇꢄꢅꢆꢄꢉꢆ.
thꢈ pꢈꢉꢃꢈꢅꢇꢄgꢈ ꢁf ꢀꢅhꢀbꢀꢇꢀꢁꢅ ꢁf coX-2 wꢄs
ꢆꢈꢇꢈꢉmꢀꢅꢈꢆ ꢄꢅꢆ ꢇhꢈ ꢉꢈsꢋꢂꢇs ꢀꢅꢆꢀꢃꢄꢇꢈꢆ ꢇhꢄꢇ ꢇhꢈ Fa
ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs wꢈꢉꢈ ꢂꢈss ꢄꢃꢇꢀꢊꢈ ꢇhꢄꢅ ꢆꢀꢃꢂꢁfꢈꢅꢄꢃ ꢀꢅ ꢀꢅhꢀb-
ꢇꢀꢅg coX-2 in vitro (Fꢀgꢋꢉꢈ 4). Hꢁwꢈꢊꢈꢉ, ꢆꢀꢃꢂꢁfꢈꢅꢄꢃ
hꢄs sꢈꢊꢈꢉꢄꢂ ꢋꢅꢆꢈsꢀꢉꢄbꢂꢈ ꢈffꢈꢃꢇs sꢋꢃh ꢄs hꢈpꢄꢇꢁꢇꢁxꢀꢃꢀꢇy
aꢀꢇhꢄꢂ 2011). cꢁmpꢄꢉꢀꢅg Fa ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs (Fꢀgꢋꢉꢈ 4),
Acknowledgements
Wꢈ ꢇhꢄꢅk dꢉ. eꢆꢋꢄꢉꢆꢁ Pꢄꢆꢀꢂꢂꢄ (ciateJ, Mꢈxꢀꢃꢁ) fꢁꢉ
sꢋppꢁꢉꢇ wꢀꢇh ꢄꢅꢇꢀ-ꢀꢅflꢄmmꢄꢇꢁꢉy ꢄꢃꢇꢀꢊꢀꢇy ꢄssꢄys.
ꢀ
(
Declaration of interest: conacYt (Mꢈxꢀꢃꢁ) i010/
214/2012-165141, uBa: uBacYt 20020100100304,
conicet:PiP 112-200801-00801/09,ꢄꢅꢆanPcyt
wꢈ ꢁbsꢈꢉꢊꢈꢆ ꢇhꢄꢇ ꢃꢁmpꢁꢋꢅꢆs 3 ꢄꢅꢆ 5, whꢀꢃh ꢃꢁꢅꢇꢄꢀꢅ
ꢄ ꢂꢁꢅg-ꢃhꢄꢀꢅ ꢄꢂꢃꢁhꢁꢂ ꢁꢉ ꢃꢄꢉbꢁxyꢂꢀꢃ ꢄꢃꢀꢆ, wꢈꢉꢈ mꢁꢉꢈ

8
G. Sandoval et al.
Pict 2011-00595 (aꢉgꢈꢅꢇꢀꢅꢄ) pꢄꢉꢇꢀꢄꢂꢂy fiꢅꢄꢅꢃꢈꢆ
ꢇhꢀs ꢉꢈsꢈꢄꢉꢃh. Pꢉꢁjꢈꢃꢇ Bio2013-48779-c4-1-r fꢉꢁm
Spꢄꢅꢀsh Mꢀꢅꢀsꢇꢉy ꢁf eꢃꢁꢅꢁmy ꢄꢅꢆ cꢁmpꢈꢇꢀꢇꢀꢊꢈꢅꢈss,
enZnut ꢅꢈꢇwꢁꢉk (cYted), ꢄꢅꢆ coSt ꢄꢃꢇꢀꢁꢅ
cM1303 ꢁꢅ Sysꢇꢈms Bꢀꢁꢃꢄꢇꢄꢂysꢀs ꢄꢂsꢁ sꢋppꢁꢉꢇꢈꢆ
ꢇhꢀs wꢁꢉk. a.B. ꢀs ꢄ rꢈsꢈꢄꢉꢃh Mꢈmbꢈꢉ ꢁf conicet
Kꢄꢇsꢁꢋꢉꢄ MH, Pꢁꢂyꢆꢈꢉꢄ ac,tsꢀꢉꢁꢅꢀs ld, Pꢈꢇꢉꢄkꢀ MP, rꢄjꢄꢃꢀꢃ SK,
tsꢈꢂꢈpꢀs ad, Sꢇꢄmꢄꢇꢀs H. 2009ꢄ. effiꢃꢀꢈꢅꢇ ꢈꢅzymꢄꢇꢀꢃ pꢉꢈpꢄꢉꢄ-
ꢇꢀꢁꢅ ꢁf hyꢆꢉꢁxyꢃꢀꢅꢅꢄmꢄꢇꢈs ꢀꢅ ꢀꢁꢅꢀꢃ ꢂꢀqꢋꢀꢆs ꢈꢅhꢄꢅꢃꢈs ꢇhꢈꢀꢉ
ꢄꢅꢇꢀꢁxꢀꢆꢄꢅꢇ ꢈffꢈꢃꢇ ꢁꢅ ꢂꢀpꢁpꢉꢁꢇꢈꢀꢅs ꢁxꢀꢆꢄꢇꢀꢊꢈ mꢁꢆꢀfiꢃꢄꢇꢀꢁꢅ.
n Bꢀꢁꢇꢈꢃhꢅꢁꢂ 26:83–91.
Kꢄꢇsꢁꢋꢉꢄ MH, thꢈꢁꢆꢁsꢀꢁꢋ e, Sꢇꢄmꢄꢇꢀs H, Kꢁꢂꢀsꢀs Fn. 2009b.
Sꢇꢉꢄꢇꢈgꢀꢈs fꢁꢉ ꢇhꢈ bꢀꢁꢃꢄꢇꢄꢂyꢇꢀꢃ ꢂꢀpꢁphꢀꢂꢀzꢄꢇꢀꢁꢅ ꢁf phꢈꢅꢁꢂꢀꢃ
ꢄꢅꢇꢀꢁxꢀꢆꢄꢅꢇs. iꢅ: Fꢈssꢅꢈꢉ Wd, aꢅꢇhꢁꢅsꢈꢅ t, ꢈꢆs. Mꢁꢆꢈꢉꢅ
Bꢀꢁꢃꢄꢇꢄꢂysꢀs: Sꢇꢈꢉꢈꢁsꢈꢂꢈꢃꢇꢀꢊꢈ ꢄꢅꢆ eꢅꢊꢀꢉꢁꢅmꢈꢅꢇꢄꢂꢂy Fꢉꢀꢈꢅꢆꢂy
rꢈꢄꢃꢇꢀꢁꢅs. Wꢈꢀꢅhꢈꢀm: Wꢀꢂꢈy-vcH. pp. 123–133.
(
aꢉgꢈꢅꢇꢀꢅꢄ).Wꢈ ꢇhꢄꢅk ꢇhꢈ Spꢄꢅꢀsh Mꢀꢅꢀsꢇꢉy ꢁf eꢆꢋ-
ꢃꢄꢇꢀꢁꢅ ꢄꢅꢆ Sꢃꢀꢈꢅꢃꢈ fꢁꢉ ꢄ sꢄbbꢄꢇꢀꢃꢄꢂ gꢉꢄꢅꢇ ꢇꢁ G.S.
SB2010-004). thꢈ ꢄꢋꢇhꢁꢉs ꢉꢈpꢁꢉꢇ ꢅꢁ ꢃꢁꢅflꢀꢃꢇs ꢁf
ꢅꢇꢈꢉꢈsꢇ. thꢈ ꢄꢋꢇhꢁꢉs ꢄꢂꢁꢅꢈ ꢄꢉꢈ ꢉꢈspꢁꢅsꢀbꢂꢈ fꢁꢉ ꢇhꢈ
(
ꢀ
lꢈꢈ YS. 2005. rꢁꢂꢈ ꢁf nadPH ꢁxꢀꢆꢄsꢈ-mꢈꢆꢀꢄꢇꢈꢆ gꢈꢅꢈꢉꢄꢇꢀꢁꢅ ꢁf
ꢉꢈꢄꢃꢇꢀꢊꢈ ꢁxygꢈꢅ spꢈꢃꢀꢈs ꢀꢅ ꢇhꢈ mꢈꢃhꢄꢅꢀsm ꢁf ꢄpꢁpꢇꢁsꢀs ꢀꢅꢆꢋꢃꢈꢆ
by phꢈꢅꢁꢂꢀꢃ ꢄꢃꢀꢆs ꢀꢅ HꢈpG2 hꢋmꢄꢅ hꢈpꢄꢇꢁmꢄ ꢃꢈꢂꢂs. aꢉꢃh
Phꢄꢉm rꢈs 28:1183–1189.
ꢃꢁꢅꢇꢈꢅꢇ ꢄꢅꢆ wꢉꢀꢇꢀꢅg ꢁf ꢇhꢈ ꢄꢉꢇꢀꢃꢂꢈ
lꢀ BQ, lꢀ nG, Fꢈꢅg F, tꢄꢅgYP, dꢋꢄꢅ Ja. 2009ꢄ. Syꢅꢇhꢈsꢀs ꢄꢅꢆ
ꢄꢅꢇꢀ-pꢂꢄꢇꢈꢂꢈꢇ ꢄggꢉꢈgꢄꢇꢀꢁꢅ ꢄꢃꢇꢀꢊꢀꢇꢀꢈs ꢁf fꢈꢉꢋꢂꢀꢃ ꢄꢃꢀꢆ ꢈsꢇꢈꢉs. J chꢀꢅꢄ
Phꢄꢉm uꢅꢀꢊ 40:486–490.
References
aꢀꢇhꢄꢂ GP. 2011. Hꢈpꢄꢇꢁꢇꢁxꢀꢃꢀꢇy ꢉꢈꢂꢄꢇꢈꢆ ꢇꢁ ꢄꢅꢇꢀꢉhꢈꢋmꢄꢇꢀꢃ ꢆꢉꢋgs.
nꢄꢇ rꢈꢊ rhꢈꢋmꢄꢇꢁꢂ 7:139–150.
lꢀ nG, Shꢀ ZH,tꢄꢅgYP, lꢀ BQ, dꢋꢄꢅ Ja. 2009b. Hꢀghꢂy ꢈffiꢃꢀꢈꢅꢇ
ꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢁf fꢈꢉꢋꢂꢀꢃ ꢄꢃꢀꢆ ꢋꢅꢆꢈꢉ mꢀꢃꢉꢁwꢄꢊꢈ ꢀꢉꢉꢄꢆꢀꢄꢇꢀꢁꢅ.
Mꢁꢂꢈꢃꢋꢂꢈs 14:2118–2126.
Mꢋꢅꢀꢅ a, eꢆwꢄꢉꢆs-lꢈꢊy F. 2011. eꢅꢃꢄpsꢋꢂꢄꢇꢀꢁꢅ ꢁf ꢅꢄꢇꢋꢉꢄꢂ
pꢁꢂyphꢈꢅꢁꢂꢀꢃ ꢃꢁmpꢁꢋꢅꢆs; ꢄ ꢉꢈꢊꢀꢈw. Phꢄꢉmꢄꢃꢈꢋꢇꢀꢃs 3:793–829.
nꢁꢅꢅꢈꢅmꢄꢃhꢈꢉ a, Mꢄyꢈꢉ r, Pꢂꢀꢈꢅꢀꢅgꢈꢉ H. 1983. Hꢀgh pꢉꢈssꢋꢉꢈ
ꢈxpꢈꢉꢀmꢈꢅꢇs. Xii. appꢂꢀꢃꢄꢇꢀꢁꢅ ꢁf hꢀgh pꢉꢈssꢋꢉꢈ ꢀꢅ Wꢀꢇꢇꢀg
ꢉꢈꢄꢃꢇꢀꢁꢅs wꢀꢇh ꢉꢈsꢁꢅꢄꢅꢃꢈ sꢇꢄbꢀꢂꢀsꢈꢆ yꢂꢀꢆꢈs. lꢀꢈbꢀgs aꢅꢅ chꢈm
12:2135–2140.
Bꢄꢉbꢈꢉꢁꢋssꢈ H, rꢁꢀsꢈꢋx o, rꢁbꢈꢉꢇ c, Pꢄqꢋꢁꢇ M, dꢈꢉꢁꢄꢅꢅꢈ c,
Bꢂꢈꢃkꢈꢉ c. 2008. aꢅꢄꢂyꢇꢀꢃꢄꢂ mꢈꢇhꢁꢆꢁꢂꢁgꢀꢈs fꢁꢉ qꢋꢄꢅꢇꢀfiꢃꢄꢇꢀꢁꢅ ꢁf
fꢈꢉꢋꢂꢀꢃ ꢄꢃꢀꢆ ꢄꢅꢆ ꢀꢇs ꢁꢂꢀgꢁmꢈꢉs. J Sꢃꢀ Fꢁꢁꢆ agꢉꢀꢃ 88:1494–1511.
cꢄꢉꢉꢈꢄ G, rꢀꢊꢄ S. 2008. oꢉgꢄꢅꢀꢃ Syꢅꢇhꢈsꢀs wꢀꢇh eꢅzymꢈs ꢀꢅ
nꢁꢅ-aqꢋꢈꢁꢋs Mꢈꢆꢀꢄ. Wꢈꢀꢅhꢈꢀm: Wꢀꢂꢈy-vcH.
cꢄsꢄs-Gꢁꢆꢁy l, dꢋqꢋꢈsꢅꢈ S, Bꢁꢉꢆꢈs F, Sꢄꢅꢆꢁꢊꢄꢂ G, Mꢄꢉꢇy a.
2
012. lꢀpꢄsꢈs:aꢅ ꢁꢊꢈꢉꢊꢀꢈw. iꢅ: Sꢄꢅꢆꢁꢊꢄꢂ G, eꢆꢀꢇꢁꢉ. lꢀpꢄsꢈs ꢄꢅꢆ
Phꢁsphꢁꢂꢀpꢄsꢈs: Mꢈꢇhꢁꢆs ꢄꢅꢆ Pꢉꢁꢇꢁꢃꢁꢂs. nꢈw Jꢈꢉsꢈy:Hꢋmꢄꢅꢄ
Pꢉꢈss. pp. 3–30.
chꢈꢅ H, Wꢋ J,Yꢄꢅg l, Xꢋ G. 2014. chꢄꢉꢄꢃꢇꢈꢉꢀzꢄꢇꢀꢁꢅ ꢄꢅꢆ sꢇꢉꢋꢃ-
ꢇꢋꢉꢈ bꢄsꢀs ꢁf Pseudomonas alcaligenes ꢂꢀpꢄsꢈ’s ꢈꢅꢄꢅꢇꢀꢁpꢉꢈfꢈꢉꢈꢅꢃꢈ
ꢇꢁwꢄꢉꢆs d,l-mꢈꢅꢇhyꢂ pꢉꢁpꢀꢁꢅꢄꢇꢈ. J Mꢁꢂ cꢄꢇꢄꢂ B-eꢅzym 102:
Pꢂꢁꢋ FJ, cꢉꢋꢃꢈs Ma, Fꢈꢉꢉꢈꢉ M, Fꢋꢈꢅꢇꢈs G, Pꢄsꢇꢁꢉ e, Bꢈꢉꢅꢄbꢈ M,
chꢉꢀsꢇꢈꢅsꢈꢅ M, cꢁmꢈꢂꢂꢈs F, Pꢄꢉꢉꢄ Jl, Bꢄꢂꢂꢈsꢇꢈꢉꢁs a. 2002.
eꢅzymꢄꢇꢀꢃ ꢄꢃyꢂꢄꢇꢀꢁꢅ ꢁf ꢆꢀ- ꢄꢅꢆ ꢇꢉꢀsꢄꢃꢃhꢄꢉꢀꢆꢈs wꢀꢇh fꢄꢇꢇy ꢄꢃꢀꢆs:
ꢃhꢁꢁsꢀꢅg ꢇhꢈ ꢄppꢉꢁpꢉꢀꢄꢇꢈ ꢈꢅzymꢈ, sꢋppꢁꢉꢇ ꢄꢅꢆ sꢁꢂꢊꢈꢅꢇ. J
Bꢀꢁꢇꢈꢃhꢅꢁꢂ 96:55–66.
8
1–87.
Pꢂꢁꢋ FJ, cꢉꢋꢃꢈs Ma, Pꢄsꢇꢁꢉ e, Fꢈꢉꢉꢈꢉ M, Bꢈꢉꢅꢄbꢈ M,
Bꢄꢂꢂꢈsꢇꢈꢉꢁs a. 1999.aꢃyꢂꢄꢇꢀꢁꢅ ꢁf sꢋꢃꢉꢁsꢈ wꢀꢇh ꢊꢀꢅyꢂ ꢈsꢇꢈꢉs ꢋsꢀꢅg
ꢀmmꢁbꢀꢂꢀzꢈꢆ hyꢆꢉꢁꢂꢄsꢈs: ꢆꢈmꢁꢅsꢇꢉꢄꢇꢀꢁꢅ ꢇhꢄꢇ ꢃhꢈmꢀꢃꢄꢂ ꢃꢄꢇꢄꢂysꢀs
mꢄy ꢀꢅꢇꢈꢉfꢈꢉꢈ wꢀꢇh ꢈꢅzymꢄꢇꢀꢃ ꢃꢄꢇꢄꢂysꢀs. Bꢀꢁꢇꢈꢃhꢅꢁꢂ lꢈꢇꢇ 21:
635–639.
chꢁqꢋꢈꢅꢈꢇ B, cꢁꢋꢇꢈꢄꢋ c, Pꢄpꢄꢉꢀs e, cꢁꢀffꢄꢉꢆ lJM. 2008.
iꢅꢇꢈꢉꢈsꢇ ꢁf fꢈꢉꢋꢂꢀꢃ ꢄꢃꢀꢆ ꢈꢇhyꢂ ꢈsꢇꢈꢉ ꢀꢅ phꢁꢇꢁpꢉꢁꢇꢈꢃꢇꢀꢊꢈ ꢃꢉꢈꢄms:
Mꢈꢄsꢋꢉꢈ ꢁf ꢈffiꢃꢄꢃy by in vitro mꢈꢇhꢁꢆ. nꢄꢇ Pꢉꢁꢆ rꢈs 22:
1
467–1471.
cꢁmpꢇꢁꢅ dl, lꢄszꢂꢁ Ja, Bꢈꢉhꢁw Ma. 2000. lꢀpꢄsꢈ-ꢃꢄꢇꢄꢂyzꢈꢆ
syꢅꢇhꢈsꢀs ꢁf fꢈꢉꢋꢂꢄꢇꢈ ꢈsꢇꢈꢉs. J am oꢀꢂ chꢈm Sꢁꢃ 77:513–519.
Fꢈꢉꢉꢈꢀꢉꢄ-dꢀꢄs S, Sꢄꢅꢆꢁꢊꢄꢂ G, Pꢂꢁꢋ F,vꢄꢂꢈꢉꢁ F. 2013.thꢈ pꢁꢇꢈꢅꢇꢀꢄꢂ
ꢋsꢈ ꢁf ꢂꢀpꢄsꢈs ꢀꢅ ꢇhꢈ pꢉꢁꢆꢋꢃꢇꢀꢁꢅ ꢁf fꢄꢇꢇy ꢄꢃꢀꢆ ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs fꢁꢉ ꢇhꢈ
fꢁꢁꢆ ꢄꢅꢆ ꢅꢋꢇꢉꢄꢃꢈꢋꢇꢀꢃꢄꢂ ꢀꢅꢆꢋsꢇꢉꢀꢈs. eꢂꢈꢃꢇꢉꢁꢅ J Bꢀꢁꢇꢈꢃhꢅ 16:3
Fꢈꢉꢉꢈꢉ M, cꢉꢋꢃꢈs Ma, Pꢂꢁꢋ FJ, Bꢈꢉꢅꢄbꢈ M, Bꢄꢂꢂꢈsꢇꢈꢉꢁs a. 2000.
a sꢀmpꢂꢈ pꢉꢁꢃꢈꢆꢋꢉꢈ fꢁꢉ ꢇhꢈ ꢉꢈgꢀꢁsꢈꢂꢈꢃꢇꢀꢊꢈ syꢅꢇhꢈsꢀs ꢁf fꢄꢇꢇy ꢄꢃꢀꢆ
ꢈsꢇꢈꢉs ꢁf mꢄꢂꢇꢁsꢈ, ꢂꢈꢋꢃꢉꢁsꢈ, mꢄꢂꢇꢁꢇꢉꢀꢁsꢈ ꢄꢅꢆ ꢅ-ꢆꢁꢆꢈꢃyꢂ mꢄꢂꢇꢁsꢀꢆꢈs.
tꢈꢇꢉꢄhꢈꢆꢉꢁꢅ 56:4053–4061.
Pꢉꢄꢆꢈꢂꢂꢈs P, Gꢉꢄssꢀ J, Mꢄꢃꢂꢁꢋf Ja.1985. eꢅzymꢈ ꢀmmꢋꢅꢁꢄssꢄys ꢁf
ꢈꢀꢃꢁsꢄꢅꢁꢀꢆs ꢋsꢀꢅg ꢄꢃꢈꢇyꢂꢃhꢁꢂꢀꢅꢈsꢇꢈꢉꢄsꢈ ꢄs ꢂꢄbꢈꢂ: aꢅ ꢄꢂꢇꢈꢉꢅꢄꢇꢀꢊꢈ
ꢇꢁ ꢉꢄꢆꢀꢁꢀmmꢋꢅꢁꢄssꢄy. aꢅꢄꢂ chꢈm 57:1170–1173.
Qꢋꢀꢅꢇꢄꢅꢄ PG, Sꢄꢅꢆꢁꢊꢄꢂ G, Bꢄꢂꢆꢈssꢄꢉꢀ a. 2011. lꢀpꢄsꢈ-ꢃꢄꢇꢄꢂyzꢈꢆ
syꢅꢇhꢈsꢀs ꢁf mꢈꢆꢀꢋm- ꢄꢅꢆ ꢂꢁꢅg-ꢃhꢄꢀꢅ ꢆꢀꢈsꢇꢈꢉs ꢁf 2-ꢁxꢁgꢂꢋꢇꢄꢉꢀꢃ
ꢄꢃꢀꢆ. Bꢀꢁꢃꢄꢇꢄꢂ Bꢀꢁꢇꢉꢄꢅsfꢁꢉ 29:186–191.
rꢈyꢈs-dꢋꢄꢉꢇꢈ d, lꢁpꢈz-cꢁꢉꢇꢈs n, Fꢈꢉꢉꢈꢉ M, Pꢂꢁꢋ FJ, Bꢄꢂꢂꢈsꢇꢈꢉꢁs a.
2005. Pꢄꢉꢄmꢈꢇꢈꢉs ꢄffꢈꢃꢇꢀꢅg pꢉꢁꢆꢋꢃꢇꢀꢊꢀꢇy ꢀꢅ ꢇhꢈ ꢂꢀpꢄsꢈ-ꢃꢄꢇꢄꢂysꢈꢆ
syꢅꢇhꢈsꢀs ꢁf sꢋꢃꢉꢁsꢈ pꢄꢂmꢀꢇꢄꢇꢈ. Bꢀꢁꢃꢄꢇꢄꢂ Bꢀꢁꢇꢉꢄꢅsfꢁꢉ 23:19–27.
Sꢁꢉꢈꢅsꢈꢅ adM, lyꢅꢈbꢁꢉg KS, vꢀꢂꢂꢈꢅꢈꢋꢊꢈ P, Jꢄꢃꢁbsꢈꢅ c. 2014.
aꢂkyꢂ ꢃhꢄꢀꢅ ꢂꢈꢅgꢇh ꢀmpꢄꢃꢇs ꢇhꢈ ꢄꢅꢇꢀꢁxꢀꢆꢄꢇꢀꢊꢈ ꢈffꢈꢃꢇ ꢁf ꢂꢀpꢁphꢀꢂꢀzꢈꢆ
fꢈꢉꢋꢂꢀꢃ ꢄꢃꢀꢆ ꢀꢅ fish ꢁꢀꢂ ꢈꢅꢉꢀꢃhꢈꢆ mꢀꢂk. J Fꢋꢅꢃꢇ Fꢁꢁꢆ doi:10.1016/j.
jff.2014.04.008.
Gꢄꢉꢃꢀꢄ-lꢀñꢄꢉꢈs G, Pꢄꢉꢉꢄꢋꢆ G, lꢄbꢉꢀꢁꢂꢄ c, Bꢄꢂꢆꢈssꢄꢉꢀ a. 2012.
chꢈmꢁꢈꢅzymꢄꢇꢀꢃ syꢅꢇhꢈsꢀs ꢄꢅꢆ bꢀꢁꢂꢁgꢀꢃꢄꢂ ꢈꢊꢄꢂꢋꢄꢇꢀꢁꢅ ꢁf 2- ꢄꢅꢆ
3
-hyꢆꢉꢁxypyꢉꢀꢆꢀꢅꢈ ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs ꢄgꢄꢀꢅsꢇ Leishmania mexicana.
Bꢀꢁꢁꢉg Mꢈꢆ chꢈm 20:4614–4624.
Gꢁꢅzꢄꢂꢈz-Sꢄbꢀꢅ J, Mꢁꢉꢄꢅ-rꢄmꢄꢂꢂꢄꢂ r, rꢈbꢁꢂꢂꢈꢆꢁ F. 2011.
rꢈgꢀꢁsꢈꢂꢈꢃꢇꢀꢊꢈ ꢈꢅzymꢄꢇꢀꢃ ꢄꢃyꢂꢄꢇꢀꢁꢅ ꢁf ꢃꢁmpꢂꢈx ꢅꢄꢇꢋꢉꢄꢂ pꢉꢁꢆꢋꢃꢇs:
expꢄꢅꢆꢀꢅg mꢁꢂꢈꢃꢋꢂꢄꢉ ꢆꢀꢊꢈꢉsꢀꢇy. chꢈm Sꢁꢃ rꢈꢊ 40:5321–5335.
Gꢋyꢁꢇ B, Bꢁsqꢋꢈꢇꢇꢈ B, Pꢀꢅꢄ M, Gꢉꢄꢀꢂꢂꢈ J. 1997. esꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ ꢁf
phꢈꢅꢁꢂꢀꢃ ꢄꢃꢀꢆs fꢉꢁm gꢉꢈꢈꢅ ꢃꢁffꢈꢈ wꢀꢇh ꢄꢅ ꢀmmꢁbꢀꢂꢀzꢈꢆ ꢂꢀpꢄsꢈ
fꢉꢁm Candida antarctica ꢀꢅ sꢁꢂꢊꢈꢅꢇ-fꢉꢈꢈ mꢈꢆꢀꢋm. Bꢀꢁꢇꢈꢃhꢅꢁꢂ
lꢈꢇꢇ 19:529–532.
Sꢁꢋꢇꢁ eB, aꢅsꢈꢂmꢀ c, cꢈꢅꢇꢀꢅꢀ M, Müꢂꢂꢈꢉ rH. 2005. Pꢉꢈpꢄꢉꢄꢇꢀꢁꢅ
ꢄꢅꢆ ꢃhꢄꢉꢄꢃꢇꢈꢉꢀzꢄꢇꢀꢁꢅ ꢁf ꢅ-ꢆꢁꢆꢈꢃyꢂ-fꢈꢉꢋꢂꢄꢇꢈ-ꢂꢁꢄꢆꢈꢆ sꢁꢂꢀꢆ ꢂꢀpꢀꢆ
ꢅꢄꢅꢁpꢄꢉꢇꢀꢃꢂꢈs (Sln). iꢅꢇ J Phꢄꢉm 295:261–268.
Sꢉꢀꢅꢀꢊꢄsꢄꢅ M, Sꢋꢆhꢈꢈꢉ ar, Mꢈꢅꢁꢅ vP. 2007. Fꢈꢉꢋꢂꢀꢃ ꢄꢃꢀꢆ:
thꢈꢉꢄpꢈꢋꢇꢀꢃ pꢁꢇꢈꢅꢇꢀꢄꢂ ꢇhꢉꢁꢋgh ꢀꢇs ꢄꢅꢇꢀꢁxꢀꢆꢄꢅꢇ pꢉꢁpꢈꢉꢇy. J cꢂꢀꢅ
Bꢀꢁꢃhꢈm nꢋꢇꢉ 40:92–100.
Sꢇꢈꢊꢈꢅsꢁꢅ de, Pꢄꢉkꢄꢉ SG, Zhꢄꢅg J, Sꢇꢄꢅꢂꢈy ra, Jꢈꢅsꢈꢅ dJ,
cꢁꢁꢅꢈy JM. 2007. cꢁmbꢀꢅꢄꢇꢁꢉꢀꢄꢂ ꢈꢅzymꢀꢃ syꢅꢇhꢈsꢀs fꢁꢉ fꢋꢅꢃꢇꢀꢁꢅꢄꢂ
ꢇꢈsꢇꢀꢅg ꢁf phꢈꢅꢁꢂꢀꢃ ꢄꢃꢀꢆ ꢈsꢇꢈꢉs ꢃꢄꢇꢄꢂysꢈꢆ by Candida antarctica
Jꢁshꢀ G, Pꢈꢉꢂꢋꢀgꢀ M, Sꢋꢂꢇꢄꢅꢄ r, agꢉꢀppꢀꢅꢁ r, cꢄꢂꢄbꢉꢈsꢈ v,
Bꢋꢇꢇꢈꢉfiꢈꢂꢆ da. 2006. In vivo pꢉꢁꢇꢈꢃꢇꢀꢁꢅ ꢁf syꢅꢄpꢇꢁsꢁmꢈs by
fꢈꢉꢋꢂꢀꢃ ꢄꢃꢀꢆ ꢈꢇhyꢂ ꢈsꢇꢈꢉ (Faee) fꢉꢁm ꢁxꢀꢆꢄꢇꢀꢊꢈ sꢇꢉꢈss mꢈꢆꢀꢄꢇꢈꢆ
by 2,2-ꢄzꢁbꢀs(2-ꢄmꢀꢆꢀꢅꢁ-pꢉꢁpꢄꢅꢈ)ꢆꢀhyꢆꢉꢁꢃhꢂꢁꢉꢀꢆꢈ (aaPH) ꢁꢉ
ꢂꢀpꢄsꢈ
B (nꢁꢊꢁzym 435). eꢅzymꢈ Mꢀꢃꢉꢁb tꢈꢃhꢅꢁꢂ 40:
1078–1086.
2
Fꢈ /H o : iꢅsꢀghꢇ ꢀꢅꢇꢁ mꢈꢃhꢄꢅꢀsms ꢁf ꢅꢈꢋꢉꢁpꢉꢁꢇꢈꢃꢇꢀꢁꢅ ꢄꢅꢆ
Sꢋꢂꢇꢄꢅꢄ r. 2012. Fꢈꢉꢋꢂꢀꢃ ꢄꢃꢀꢆ ꢈꢇhyꢂ ꢈsꢇꢈꢉ ꢄs ꢄ pꢁꢇꢈꢅꢇꢀꢄꢂ ꢇhꢈꢉꢄpy
ꢀꢅ ꢅꢈꢋꢉꢁꢆꢈgꢈꢅꢈꢉꢄꢇꢀꢊꢈ ꢆꢀsꢁꢉꢆꢈꢉs. BBa-Mꢁꢂ Bꢄsꢀs dꢀs 1822:
748–752.
2
2
ꢉꢈꢂꢈꢊꢄꢅꢃꢈ ꢇꢁ ꢁxꢀꢆꢄꢇꢀꢊꢈ sꢇꢉꢈss-ꢉꢈꢂꢄꢇꢈꢆ ꢅꢈꢋꢉꢁꢆꢈgꢈꢅꢈꢉꢄꢇꢀꢊꢈ ꢆꢀsꢁꢉꢆꢈꢉs.
nꢈꢋꢉꢁꢃhꢈm iꢅꢇ 48:318–327.
Kꢄꢉmꢈꢈ SK. 2009. Bꢀꢁꢃꢄꢇꢄꢂyꢇꢀꢃ syꢅꢇhꢈsꢀs ꢁf ꢄsꢃꢁꢉbyꢂ ꢈsꢇꢈꢉs ꢄꢅꢆ
ꢇhꢈꢀꢉ bꢀꢁꢇꢈꢃhꢅꢁꢂꢁgꢀꢃꢄꢂ ꢄppꢂꢀꢃꢄꢇꢀꢁꢅs. appꢂ Mꢀꢃꢉꢁbꢀꢁꢂ Bꢀꢁꢇ 81:
tꢄꢅg K, Xꢀꢁꢅg c. 2011. Pꢉꢈpꢄꢉꢄꢇꢀꢁꢅ ꢁf fꢈꢉꢋꢂꢀꢃ ꢄꢃꢀꢆ ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs
ꢋsꢈfꢋꢂ ꢀꢅ ꢇhꢈ ꢇꢉꢈꢄꢇmꢈꢅꢇ ꢁf ꢊꢄsꢃꢋꢂꢄꢉ ꢆꢀsꢈꢄsꢈs. chꢀꢅꢈsꢈ Pꢄꢇꢈꢅꢇ cn
2011-10414593.
1
013–1022.

Ferulic acid esterification
9
tꢄꢅꢀgꢋꢃhꢀ H, nꢁmꢋꢉꢄ e, tsꢋꢅꢁ t, Mꢀꢅꢄmꢀ S. 1999. Fꢈꢉꢋꢂꢀꢃ ꢄꢃꢀꢆ
ꢈsꢇꢈꢉ ꢄꢅꢇꢀꢁxꢀꢆꢄꢅꢇ/uv ꢄbsꢁꢉbꢈꢅꢇ. uS-Pꢄꢇꢈꢅꢇ uS5908615a.
tꢁꢉꢉꢈs P, Pꢁꢊꢈꢆꢄ a, Jꢀmꢈꢅꢈz-Bꢄꢉbꢈꢉꢁ J, Bꢄꢂꢂꢈsꢇꢈꢉꢁs a, Pꢂꢁꢋ FJ.
vꢁꢀsꢀꢅ-chꢀꢉꢈꢇaS,Bꢄzꢀꢅ Ma,lꢄꢅꢃꢈꢂꢁꢇ Jc,rꢄꢋꢂꢇ S.2007.Syꢅꢇhꢈsꢀs
ꢁf ꢅꢈw l-ꢄsꢃꢁꢉbꢀꢃ fꢈꢉꢋꢂꢀꢃ ꢄꢃꢀꢆ hybꢉꢀꢆs. Mꢁꢂꢈꢃꢋꢂꢈs 12:
2533–2545.
2
010. rꢈgꢀꢁsꢈꢂꢈꢃꢇꢀꢊꢈ ꢂꢀpꢄsꢈ-ꢃꢄꢇꢄꢂyzꢈꢆ syꢅꢇhꢈsꢀs ꢁf 3-o-ꢄꢃyꢂ
Wꢈꢀꢇkꢄmp P, vꢁsmꢄꢅꢅ K, Wꢈbꢈꢉ n. 2006. Hꢀghꢂy ꢈffiꢃꢀꢈꢅꢇ
pꢉꢈpꢄꢉꢄꢇꢀꢁꢅ ꢁf ꢂꢀpꢁphꢀꢂꢀꢃ hyꢆꢉꢁxyꢃꢀꢅꢅꢄmꢄꢇꢈs by sꢁꢂꢊꢈꢅꢇ-fꢉꢈꢈ
ꢂꢀpꢄsꢈ-ꢃꢄꢇꢄꢂyzꢈꢆ ꢇꢉꢄꢅsꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ. J agꢉꢀꢃ Fꢁꢁꢆ chꢈm 54:
ꢆꢈꢉꢀꢊꢄꢇꢀꢊꢈs ꢁf ꢉꢈsꢊꢈꢉꢄꢇꢉꢁꢂ ꢄꢅꢆ sꢇꢋꢆy ꢁf ꢇhꢈꢀꢉ ꢄꢅꢇꢀꢁxꢀꢆꢄꢅꢇ
pꢉꢁpꢈꢉꢇꢀꢈs. J agꢉꢀꢃ Fꢁꢁꢆ chꢈm 58:807–813.
tꢁꢉꢉꢈs P, rꢈyꢈs-dꢋꢄꢉꢇꢈ d, Bꢄꢂꢂꢈsꢇꢈꢉꢁs a, Pꢂꢁꢋ FJ. 2012. lꢀpꢄsꢈ-
ꢃꢄꢇꢄꢂyzꢈꢆ mꢁꢆꢀfiꢃꢄꢇꢀꢁꢅ ꢁf phꢈꢅꢁꢂꢀꢃ ꢄꢅꢇꢀꢁxꢀꢆꢄꢅꢇs. iꢅ: Sꢄꢅꢆꢁꢊꢄꢂ G,
eꢆꢀꢇꢁꢉ. lꢀpꢄsꢈs ꢄꢅꢆ Phꢁsphꢁꢂꢀpꢄsꢈs: Mꢈꢇhꢁꢆs ꢄꢅꢆ Pꢉꢁꢇꢁꢃꢁꢂs.
nꢈw Jꢈꢉsꢈy:Hꢋmꢄꢅꢄ Pꢉꢈss. pp. 435–443.
tꢁꢉꢉꢈs P, rꢈyꢈs-dꢋꢄꢉꢇꢈ d, lꢁpꢈz-cꢁꢉꢇꢈs n, Fꢈꢉꢉꢈꢉ M,
Bꢄꢂꢂꢈsꢇꢈꢉꢁs a, Pꢂꢁꢋ FJ. 2008. aꢃꢈꢇyꢂꢄꢇꢀꢁꢅ ꢁf ꢊꢀꢇꢄmꢀꢅ e by
Candida antarctica ꢂꢀpꢄsꢈ B ꢀmmꢁbꢀꢂꢀzꢈꢆ ꢁꢅ ꢆꢀffꢈꢉꢈꢅꢇ ꢃꢄꢉꢉꢀꢈꢉs.
Pꢉꢁꢃꢈss Bꢀꢁꢃhꢈm 43:145–153.
7062–7068.
Yꢄꢅg Z, Gꢋꢁ Z, Xꢋ X. 2012. eꢅzymꢄꢇꢀꢃ ꢂꢀpꢁphꢀꢂꢀsꢄꢇꢀꢁꢅ ꢁf phꢈꢅꢁꢂꢀꢃ
ꢄꢃꢀꢆs ꢇhꢉꢁꢋgh ꢈsꢇꢈꢉꢀfiꢃꢄꢇꢀꢁꢅ wꢀꢇh fꢄꢇꢇy ꢄꢂꢃꢁhꢁꢂs ꢀꢅ ꢁꢉgꢄꢅꢀꢃ
sꢁꢂꢊꢈꢅꢇs. Fꢁꢁꢆ chꢈm 132:1311–1315.
Zhꢄꢁ Z, Mꢁghꢄꢆꢄsꢀꢄꢅ MH. 2008. chꢈmꢀsꢇꢉy, ꢅꢄꢇꢋꢉꢄꢂ sꢁꢋꢉꢃꢈs,
ꢆꢀꢈꢇꢄꢉy ꢀꢅꢇꢄkꢈ ꢄꢅꢆ phꢄꢉmꢄꢃꢁkꢀꢅꢈꢇꢀꢃ pꢉꢁpꢈꢉꢇꢀꢈs ꢁf fꢈꢉꢋꢂꢀꢃ ꢄꢃꢀꢆ:
a ꢉꢈꢊꢀꢈw. Fꢁꢁꢆ chꢈm 109:691–702.