• Journal of Pharmaceutical Investigation
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• 제40권4호
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• pp.251-254
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• 2010

The formation of acylated peptide impurities in poly(lactide-co-glycolide) (PLGA) formulations is one of the major challenges to the development of successful sustained-release product. Octreotide, synthetic analogue of somatostatin, has been identified to be acylated in PLGA microsphere formulations. The purpose of this study was to investigate the pH effect on the formation of acylated octreotides by PLGA. In the incubation with PLGA in 0.1 M phosphate buffer at pH 7.4, approximately 98% of octreotide adsorbed to PLGA through 14 days and 66.3% of acylated octreotides were produced after 42 days, whereas the interaction of octreotide with PLGA was significantly inhibited in the incubation at pH 4, in which the acylated octreotides were observed to be 9.2% after 42 days. In the interaction study at pH 4.1-7.4, the production of acylated octreotides was demonstrated to be dependent on environmental pH. Below pH 5.0, the acylation of octreotide was significantly inhibited. This study indicates that the pH is the major factor for the formation of acylated octreotide in PLGA formulations.

• Preventive Nutrition and Food Science
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• 제2권3호
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• pp.191-196
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• 1997

The antioxidative activity of seven different acylated anthocyanin pigments isolated from grape, sweet potato, eggplant and red cabbage was evaluated bvy using linoleic acid autoxidation and rat liver microsomal systems. The acylated anthocyanins were isolated and purified by Amberlite SAD-7, ODS and Sephadex LH-20 column omatography, and preparative HPLC. Most of acylated anthocyanisns exhibited antioxidative activity as strong as $\alpha$-tocoperol, and especially peonidin3-O--(6-O-trans-caffeyl)-2-O-(6-O-trans-feuloylglucopyranosyl)-$\beta$-D-glucopyranosyl-5-O-$\beta$-D-glucopyranoside from purple sweet potato showed the strongest activity, comparable to BHA (not significant, p<0.05) in the linoleic acid system. Meanwhile, two acylated anthocyanins from the pericarps of grape and eggplant inhibited considerably the MDA formation from rat liver microsomal lipid peroxidation induced by FeSO$_4$/$H_2O$$_2$. In particular, malvidin 3-O-(6-O-p-coumaroyl)-$\beta$-D-glucopyranosde from grape pericarps showed the strongest antioxidant activity, comparable to $\alpha$-tocopherol (not significant, p<0.05). These results suggest that the acylated anthocyanins from fruits and vegetables can be used as potential dietary ntioxidants and natural colorants.

• Archives of Pharmacal Research
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• 제14권1호
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• pp.52-54
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• 1991

A new acylated monoterpene glucoside, galloylpaeoniflorin, was isolated from Paeony root. The structure was determined by chemical and spectroscopic methods.

• 한국식품영양학회지
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• 제2권1호
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• pp.18-26
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• 1989

The objective of this study was to improved the limited functional characteristics of mungbean whole globulin. The mungbean whole globulin was acylated with succinic and acetic anhydride, and the functional properties of acylated protein were investigated, The results obtained ware as follows. 1. The UV-absorption spectra of acylated whole globulins with that of the succinylated 74% whole globulin as large blue shift of the absorption maximum and minimum wavelength from 275 nm to 269 nm, respectively. 2. The mobility of acylated whole globulin were increased on PAGE pattern, and degree of mobility was particularly remarkable in case of succinylation, 3. The water absorption capacity of whole globulin was increased by acylation. The most increased rate of whole globulin was 174,02% from succinylated 74%. The oil absorption capacity of whole globulin was increased by acylation The most increased rate of whole globulin was 165.41% from acetylated 81.77%. 4. The bulk density of whole globulin was decreased by acylation. and the greater the extent of acylation, the smaller the bulk density. 5. The foaming capacity and stability of whole globulin was increased by acylation, and remarkably high in 74% succinylated whole globulin. In contrast, however, the foaming capacity and stability of native and acylated whole globulin were decreased by heat treatment.

• Natural Product Sciences
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• 제9권4호
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• pp.241-244
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• 2003

A new (2) and a known (1) acylated taurine derivatives were isolated from MeOH extract of the starfish Certonardoa semiregularis. Another new acylated taurine derivative (3) was isolated from the MeOH extract of the sponge Erylus nobilis. The structures were determined on the basis of spectral analysis.

• Archives of Pharmacal Research
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• 제13권2호
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• pp.207-210
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• 1990

The position of interglycosidic linkages of two acylated flavonol glucorhamnosides from Ginkgo biloba leaves was unambiguously determined as 1 $\longrightarrow$ 2 linkages rather than 1 $\longrightarrow$ 4 ones on the basis of spectroscopic and chemical evidence.

• 생약학회지
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• 제30권3호
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• pp.290-294
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• 1999

From the legumes of Albizzia julibrissin Durazzini (Leguminosae), a mixture of long-chain alcohols, ${\alpha}-spinasterol$, a mixture of acylated sterol glycosides and ${\alpha}-spinasteryl$ $3-O-{\beta}-D-glucoside$ were isolated. Two mixtures of long-chain alcohols and acylated sterol glycosides were characterized as 1-hexacosanol (major) and 1-tetracosanol, and $3-O-[6'-O-palmitoyl-{\beta}-D-glucosyl]-{\alpha}-spinasterol$ (major) and its 6'-O-stearoyl ester. All compounds were identified on the basis of spectral data and chemical reactions.

• Bulletin of the Korean Chemical Society
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• 제30권3호
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• pp.703-706
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• 2009

• Applied Biological Chemistry
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• 제33권1호
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• pp.52-61
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• 1990

단백질의 기능성을 높이고자 acetic anhydride(AA), succinic anhydride (SA) 및 maleic anhydride(MA)로 단백질을 acyl화 시켜 소수성과 기능성 변화를 측정하여 기능 특성과 소수성의 관계를 고찰한 결과, 단백질의 아미노산 잔기인 amino기와 sulfhydryl기의 acyl화에는 AA에 의한 수식율이 가장 높아 amino기의 89.5 % sulfhydryl기의 72.2 %가 수식되었으며 amino기가 sulfhydryl기 보다 쉽게 acyl화 되었다. Succinyl화 및 maleyl화에 의해 어류 단백질의 소수성은 감소 하였으나 acetyl화는 단백질의 소수성이 근육 단백질보다 높다. AA, SA 및 MA로 acyl화 되면 단백질의 용해도, 유화특성, 포말특성, 수분 흡수력 및 지방 흡수력이 크게 향상되었으며 근육 단백질이 농축 단백질보다 기능적 특성이 좋았다. 단백질의 소수성 감소와 용해도 증가는 높은 상관을 보였고 유화특성 및 포말특성은 단백질의 용해도와 깊은 관련이 있었으며 단백질의 소수성도 중요하였다. 단백질의 수분 흡수력은 용해도와 상관이 크나 소수성과는 큰 관계가 없었으며 지방 흡수력은 단백질의 용해도 보다는 소수성에 더 큰 영향을 받는다.

• Journal of Pharmaceutical Investigation
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• 제41권2호
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• pp.91-94
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• 2011

The purpose of this study was to investigate the effect of peptide charge on the interaction between peptide and poly(D,L-lactide-co-glycolide) (PLGA) for evaluating mechanism of acylated peptide formation in PLGA matrix. As a model peptide, octreotide, a synthetic somatostatin analogue and active ingredient of commercial PLGA product, was used. The disulfide group of octreotide was reduced with dithiothreitol and the sulfhydryl groups were modified with N-${\beta}$-maleimidopropionic acid (BMPA) to neutralize octreotide with positive charge in physiological conditions. The BMPA-conjugated octreotide was identified by measuring the molecular mass with liquid chromatography-mass spectrometry. In the interaction study with PLGA, native octreotide showed initial adsorption to PLGA and substantial production of acylated peptides (56% of overall peptide), whereas BMPA-conjugated octreotide showed minimal adsorption to PLGA and no acylation products for 42 days. Consequently, the neutralization of octreotide completely inhibited the peptide acylation by preventing interaction of peptide with PLGA. In conclusion, this study demonstrates that the initial polymer interaction of peptide is important step for peptide acylation in PLGA matrix and suggests the modulation of peptide charge as strategy for inhibiting the formation of acylated peptide impurities.