CN114107259B - 一种碱性嗜热鼠李糖苷酶在制备活性生物黄酮中的应用 - Google Patents
一种碱性嗜热鼠李糖苷酶在制备活性生物黄酮中的应用 Download PDFInfo
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- CN114107259B CN114107259B CN202111511848.7A CN202111511848A CN114107259B CN 114107259 B CN114107259 B CN 114107259B CN 202111511848 A CN202111511848 A CN 202111511848A CN 114107259 B CN114107259 B CN 114107259B
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Abstract
本发明涉及一种碱性嗜热鼠李糖苷酶，使用该碱性嗜热鼠李糖苷酶在高温条件和不同pH条件下进行黄酮类化合物的生物转化具有很高的转化率，所述高温条件为60‑100℃，所述不同pH条件为5‑11，对黄酮类化合物的转化率可达98.5％以上。
Description
技术领域
本发明涉及生物领域，具体地，本发明涉及一种碱性嗜热鼠李糖苷酶在制备活性生物黄酮中的应用。
背景技术
α-L-鼠李糖苷酶(α-L-rhamnosidase，EC3.2.1.40)是一种特异性地水解聚糖或者糖苷类化合物末端的α-1,2、α-1,3、α-1,4、α-1、α-1,6糖苷键，释放L-鼠李糖，产生新的聚糖或糖苷类化合物的水解酶。α-L-鼠李糖苷酶在自然界的来源广泛，该酶可从细菌、酵母、真菌、植物和动物组织中分离获得。目前已报道大多数α-L-鼠李糖苷酶来源于微生物，其中，已表征的细菌源GH78家族α-L-鼠李糖苷酶有19个，大多数来源于革兰氏阳性细菌，包括芽孢杆菌属、乳酸杆菌属、梭菌属、链霉菌属和热微菌门属。CAZY数据库根据氨基酸序列相似性对糖苷水解酶进行分类，微生物来源的α-L-鼠李糖苷酶包含在GH13、GH28、GH78和GH106糖苷水解酶家族中。
α-L-鼠李糖苷酶在食品生产、医药加工和化工等方面具有好的开发前景和应用价值。作为生物催化剂，α-L-鼠李糖苷酶可以通过水解柑橘类果汁中的柚皮苷而用于果汁的脱苦、水解萜烯类糖苷增强葡萄酒的香气、水解橙皮苷使果汁澄清、水解芦丁提高黄酮类化合物的生物利用度及生物学活性，此外也可以通过α-L-鼠李糖苷酶的反向水解合成α-L-鼠李糖苷。α-L-鼠李糖苷酶可以将人参皂苷、柴胡皂苷C和薯蓣皂苷等常用中药材中的皂苷类化合物转化成活性成分。还可用于特异转化柚皮苷成为极具活性的普鲁宁。此外，α-L-鼠李糖苷酶可水解许多天然药材成分末端的α-L-鼠李糖基，水解产物为生物活性异槲皮素(enzymatically modified isoquercitrin,EMIQ)合成的关键前体，且已被批准为多种食品添加剂。
黄酮类化合物是一类广泛分布于植物中具有2-苯基色原酮结构的多酚类天然产物。研究已表明：黄酮类化合物具有多种多样的生理和药理功效，包括抗氧化作用、降血糖和血压、消炎、抗肿瘤作用、抑菌抗病毒作用、治疗心血管疾病、调节肠道菌群等等。天然黄酮类化合物通常以糖苷形式稳定存在。这类黄酮类化合物往往含有一个或者多个鼠李糖基(包括黄酮3位以及7位)，较为常见的有芦丁、柚皮苷、橘皮苷、新橙皮苷以及朝藿定C等。该系列黄酮化合物中，鼠李糖基的存在影响了它们的溶解性以及生物活性。去除鼠李糖苷可以显著地提高天然黄酮的生物利用率，最大程度发挥其生物学功效。酶法水解具有温和、高效、专一等特点，适合用于鼠李糖苷类黄酮化合物的水解，因而，高催化活性的黄酮鼠李糖苷水解酶具有巨大的应用潜力。
然而绝大部分黄酮类物质作为底物，水溶性和脂溶性溶解性很差，仅溶于热的稀碱溶液或某些有机助溶剂(譬如：甲醇)，因此大大限制了鼠李糖苷酶的工业化应用。目前的鼠李糖苷酶的酶转化和最适条件如专利申请CN202110690007.0记载的细菌来源的α-L-鼠李糖苷酶，最适pH是7，最适温度为50℃，专利申请CN201910435031.2转化反应在pH6.0和37℃下进行,专利申请CN201810110773.3转化反应在温度40℃-60℃，pH5.0-7.5条件下,CN201610635941.1最适温度为60℃,最适pH为5.0，这些现有技术均难以实现较高温度以及较碱性的环境下的黄酮类物质酶法转化。因此为弥补现有技术的不足，突破黄酮类物质溶解度的限制，需要一种耐高温稳定且能够在碱性条件下具有高活力的鼠李糖苷酶，以利于黄酮物质的转化。
发明内容
本发明开发了一种在高温条件和不同pH条件下进行黄酮类化合物的酶转化的方法，所述高温条件为60-100℃，优选80℃；所述不同pH条件为pH 5-11，优选为碱性条件pH8-10，对黄酮类化合物的转化率可达98.5％以上。
本发明使用一种碱性嗜热鼠李糖苷酶，其最适温度100℃，最适pH为10，具有高温度稳定性和pH稳定性，酶活力和转化黄酮类物质效率高，并且在转化过程中，不需要其他助溶剂，目前未发现其他的α-L-鼠李糖苷酶能够达到该水平。
因此，本发明的目的在于一种高转化率的生物转化黄酮类化合物的方法，其特征在于，所述生物转化在高温条件和不同pH条件下进行，在碱性嗜热鼠李糖苷酶的作用下进行黄酮类化合物的生物转化。所述碱性嗜热鼠李糖苷酶的氨基酸序列如SEQ ID NO：1所示。
所述黄酮类化合物选自芦丁、柚皮苷、橘皮苷、新橙皮苷或朝藿定C中一种或多种。
所述高温条件为60-100℃，优选80℃；所述不同pH条件为pH5-11，优选碱性条件pH8-10。
本发明的另一目的在于提供一种碱性嗜热鼠李糖苷酶，其特征在于，所述碱性嗜热鼠李糖苷酶的氨基酸序列如SEQ ID NO：1所示。所述碱性嗜热鼠李糖苷酶的基因编码894个氨基酸，其理论分子量为101.1kDa。
本发明的另一目的在于提供含有所述碱性嗜热鼠李糖苷酶的编码基因的重组载体或宿主细胞。
本发明的另一目的在于提供一种制备所述的碱性嗜热鼠李糖苷酶的方法，其特征在于，包括以下步骤：
1)用所述重组载体转化所述宿主细胞，得重组菌株；
2)培养重组菌株，诱导所述碱性嗜热鼠李糖苷酶表达；
3)回收并纯化所表达的所述碱性嗜热鼠李糖苷酶。
本发明的另一目的在于提供所述碱性嗜热鼠李糖苷酶在高温条件和/或碱性条件下生物转化黄酮类化合物中的应用。所述黄酮类化合物选自芦丁、柚皮苷、橘皮苷、新橙皮苷或朝藿定C中一种或多种。所述高温条件为60-100℃，优选80℃；所述不同pH条件为pH 5-11，优选为碱性条件pH 8-10。
本发明所要解决的技术问题是克服现有技术的不足，提供一种性质优良的、适合于在食品、医药应用新的碱性嗜热鼠李糖苷酶。所述碱性嗜热鼠李糖苷酶具有以下优点：
1.本发明的鼠李糖苷酶最适pH为10.0，在pH5.0-10.0具有90％的活性；当该酶与pH为5-10的缓冲液混合并孵育2h后，仍可保持95％以上的活性，具有很好的pH稳定性。转化pH条件为pH 5-11，优选为碱性条件pH 8-10。
2.本发明的鼠李糖苷酶最适温度100℃，温度稳定性高，在60-80℃孵育2h后，可保持100％的活性。转化温度为60-100℃，优选80℃。
3.本发明的鼠李糖苷酶酶活高，现有文献已研究的鼠李糖苷酶最高的酶活为来自thermophilic bacterium的鼠李糖苷酶，达到了352个酶活单位；而本发明的鼠李糖苷酶酶活可达2974个酶活单位，远高于已知的各种鼠李糖苷酶酶活。
附图说明
图1为本发明所述鼠李糖苷酶水解相关底物的水解线路图。
图2为在大肠杆菌中表达的重组鼠李糖苷酶的SDS-PAGE分析，其中，M：蛋白质Marker；1：粗酶液；2：纯化的重组鼠李糖苷酶。
图3为重组鼠李糖苷酶的最适pH。
图4为重组鼠李糖苷酶的pH稳定性。
图5为重组鼠李糖苷酶的最适温度。
图6为重组鼠李糖苷酶的热稳定性。
图7为重组鼠李糖苷酶水解转化芦丁的HPLC检测图。
图8为重组鼠李糖苷酶水解转化柚皮苷的HPLC检测图。
图9为重组鼠李糖苷酶水解转化橙皮苷的HPLC检测图。
图10为重组鼠李糖苷酶水解转化朝藿定C生成淫羊藿的HPLC检测图。
具体实施方式
为使本发明实施例的目的、技术方案和优点更加清楚，下面将结合本发明实施例中的附图，对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例是本发明的一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动的前提下所获得的所有其他实施例，都属于本发明保护的范围。
实施例一 实验试剂和相关条件
相关试剂
异丙基-β-D-硫代半乳糖苷(IPTG)，硫酸卡那霉素，琼脂粉(Solarbio公司)，Ni-NTA Resin(北京全式金生物技术有限公司),蛋白胶试剂盒(康为世纪生物科技有限公司)
相关溶液：
液体LB培养基：5g酵母提取物，10g胰蛋白胨，10g NaCl，溶解后蒸馏水定容至1L。
固体LB培养基：5g酵母提取物，10g胰蛋白胨，10g NaCl，溶解后蒸馏水定容至1L，加入15g琼脂粉。
Ni-NTA Lysis buffer：10mM Imidazole，300mM NaCl，50mM NaH2PO4，溶解后调pH为8.0，蒸馏水定容至1L。
Ni-NTA Washing buffer：50mM Imidazole，300mM NaCl，50mM NaH2PO4，溶解后调pH为8.0，蒸馏水定容至1L。
Ni-NTA 250mM Elution buffer：250mM Imidazole，300mM NaCl，50mM NaH2PO4，溶解后调pH为8.0，蒸馏水定容至1L。
Ni-NTA350mM Elution buffer：350mM Imidazole，300mM NaCl，50mM NaH2PO4，溶解后调pH为8.0，蒸馏水定容至1L。
5×SDS-PAGE Loading buffer：1.25mL 1M Tris-HCl(pH 6.8)，0.5gSDS，0.025g溴酚蓝，2.5mL甘油，加蒸馏水溶解后定容至5mL,分装1mL每管，使用前每管加入25μLβ-巯基乙醇。
5×Tris-Glycine蛋白电泳缓冲液：15.1g Tris，94g Glycine，5gSDS，蒸馏水定容至1L。
主要设备：
摇床(宁波赛福实验仪器有限公司)，生化培养箱(宁波江南仪器厂)，高速低温离心机(大龙兴创实验仪器(北京)股份公司)，超声波破碎仪(宁波新芝生物科技股份有限公司)，水浴恒温振荡器(上海力辰邦西仪器科技有限公司)，蛋白电泳仪(北京君意东方电泳设备有限公司)，高效液相色谱安捷伦1260系列结合蒸发光散射检测器(安捷伦科技有限公司)
实施例二 重组鼠李糖苷酶的制备
1.将50μL大肠杆菌感受态细胞BL21(DE3)和含有编码SEQ ID NO:1的α-L-鼠李糖苷酶的基因的质粒加入到预冷的培养管中进行转化。冰上放置20min后，42℃热激45s，之后再次置于冰上2min，在培养管中加入200μL液体LB培养基，37℃摇床培养1h后，取60μL涂布于含有50μg/mL卡那霉素抗性的固体LB平板上，在37℃培养箱中倒置过夜培养。
挑取单克隆置于卡那霉素抗性的液体LB培养基中，37℃振荡过夜培养。
2.在200mL含有50μg/mL卡那霉素抗性的液体LB培养基中接种2mL过夜培养的菌液，37℃的摇床中220rpm培养至培养液的光密度(OD600)达到0.6时，以终浓度为100μM加入IPTG诱导蛋白表达，之后在37℃摇床中200rpm培养5h。
3.诱导完成后，6000rpm离心10min收集菌体，取10mL Ni-NTA Lysis buffer重悬并洗涤收集到的菌体，6000rpm再次离心10min，再用15mL Ni-NTA Lysis buffer将菌体重悬，置于冰上进行超声波破碎。破碎功率为30％，总时间30min，超声时间3s，间隔时间5s。
4.将超声波破碎后的细胞裂解液12000rpm 4℃离心10min，上清为粗酶液，对其进行收集。
5.使用镍柱亲和层析法对目的蛋白进行纯化，先使用10个柱体积的Ni-NTA Lysisbuffer对镍柱进行平衡，平衡完成后将粗酶液缓慢加入镍柱中，之后加入20个柱体积Ni-NTA Washing buffer洗脱杂蛋白，最后用Ni-NTA 250mM Elution buffer和Ni-NTA 350mMElution buffer对目的蛋白进行洗脱并收集，得到纯酶液，即得重组鼠李糖苷酶。
对上述在大肠杆菌中表达的重组鼠李糖苷酶(步骤4和步骤5获得的粗酶液以及纯酶液)进行SDS-PAGE分析鉴定，结果如图2所示，其中，M：蛋白质Marker；1：粗酶液；2：纯化的重组鼠李糖苷酶。结果表明，通过重组表达已获得所述SEQ ID NO:1的重组鼠李糖苷酶。
SEQ ID NO:1如下：
MVHGLRIIDARVEFTVNPLGIDESKPRFSWILEHEERGQYQSAYRVIVSSSLENAVKGIGDVWDSGKVNS
RDQVIKYNGPPLSSFTKYYWRVKAWDSNGVEGDWSDVQWFETAVLKPEEWSGKWIGGGQLLRRSFRVEGS
VIEAKAYVTGLGYYELRINGERVGDRVLDPPWSEYDKTVYYSVYDVTNLVKSGENVIGLILGRGRYGPVS
PNRAQIPGLKYYDEPKASAMIRIRLSDGSVITINTDESWKCLVKGPILYDDIYNGYRYDARLEPYGWDKA
GFDDSNWVQCSVVKPPGGRLRSTAAVPGTKVKGTLKPREYYNPRPGVYVFDFGQNITGWVRLRVRGSSGV
EVKVRHSEVINSDGSLNVENIRGAEATDTYILSGRDVEVLEPRFTYHGFRYAEVTGYPGVPSIDDVEAVI
VQTDFESTGSIATSSKIINDIHRITWWSLRANLLNGIQTDCPQRDERMGWLGDAWLSSDSAVFNFNMVKY
YEKFIRDIIDSQRDDGSIPDTVPPYWNTYPADPAWGTALIYIPWLLYVHYGDVEILEEAYEAMKKWWSFL
NSRVKDNVLYFSKYGEWVPPGRVFSAEYCPPEILSTWILYRDTLTLAQIAKVLGRGEDASFFTKRAEEIR
DAFNRVFLTERGYYSKYTAPDGSVRMLGGSQTCNALPLYLDMVPGNRVNDIVKALAHNIEADWDRHLVVG
IFGAKYVPEVLVKYGYVDLAYRAVTQESYPGWGYMIKEGATTLWERWEKLTGAGMNSHNHHMFGSIDAWF
YRDLAGLMTLEPGFSRIMIKPNIPSELRYCSASLYTVRGLTSVEWSRVNDELVVTVTVPVNSTAEVHLPK
LGESTVVREGDKVLWSGGKVVEVSPGVLSVKDAGDRIVVEVGSGRFIFTIKTIN
实施例三 重组鼠李糖苷酶的性质
对实施例二获得的重组鼠李糖苷酶进行酶活以及其性质的检测。
1.酶活测定方法反应体系500μL，20μL10mmol/L对硝基苯α-L-鼠李糖糖苷(pNPR)加入460μL 50mmol/L甘氨酸-氢氧化钠缓冲液(pH10.0)，先在80℃孵育5min，再加入20μL酶液(稀释到合适的倍数)反应10min，再加入1mol/L的碳酸钠溶液500μL终止反应。
在405nm下测定吸光值。酶活力单位(U)定义为：在测定条件下，每分钟产生1μmol对硝基苯酚所需要的酶量为1个酶活力单位。纯化后酶的比活力是2974U/mg。
2.最适pH的测定
在不同的pH(2.0-12.0)条件下，80℃分别测定酶活，发现所述重组α-L-鼠李糖苷酶的最适反应pH为10.0；在pH5-10的范围内，均保持90％以上的活性，结果见图3。
3.pH稳定性的测定
在不同的pH(3.0-12.0)，80℃温育2h，测定酶活，所述重组鼠李糖苷酶在pH为5-10的缓冲液混合并孵育2h后，仍可保持95％以上的活性，可见所述重组α-L-鼠李糖苷酶是一种碱性鼠李糖苷酶，且适应pH范围较广，可在碱性较强的环境下保持较高活性，结果见图4。
4.最适温度的测定
在60-140℃范围内(超过100℃，用油浴)，每隔10℃，分别测定酶活，发现所述鼠李糖苷酶的最适反应温度为100℃，可见所述鼠李糖苷酶是一种碱性嗜热鼠李糖苷酶，结果见图5。
5.温度稳定性
在不同的温度(60℃-90℃)条件下温育2h，分别在不同时间段测定酶活，所述碱性嗜热重组α-L-鼠李糖苷酶在60-80℃下的温度稳定性较好，2h后仍有100％的酶活力，结果见图6。
实施例四 重组鼠李糖苷酶在各底物的转化实验
基于上述酶学性质，选择所述重组鼠李糖苷酶在最适条件下(80℃/pH＝10)对芦丁、柚皮苷、橘皮苷以及朝藿定C进行转化实验，并测定转化率。
1.转化实验条件
芦丁转化反应体系为1L，包括50mg纯化后酶液，100g芦丁，50mM Glycine-NaOH pH＝10缓冲液中，80℃200r/min水浴震荡。
柚皮苷与橘皮苷转化反应体系为1L，包括50mg纯化后酶液，100g底物，50mMNa2HPO4-NaH2PO4 pH＝8缓冲液中，80℃200r/min水浴震荡。
朝藿定C转化反应体系为1L，包括50mg纯化后酶液，100g朝藿定C，50mM Glycine-NaOH pH＝10缓冲液中，80℃200r/min水浴震荡。
2.转化产物检测条件
芦丁液相检测条件色谱柱采用C18柱，流动相A为0.1％磷酸水,流动相B乙腈，检测波长270nm，流速为1ml/min，进样量5μL，柱温26℃，HPLC程序如表1。
表1芦丁液相检测条件HPLC程序
| 时间(min) | 流动相A(％) | 流动相B(％) |
| 0 | 75 | 25 |
| 16 | 73 | 27 |
| 23 | 64 | 36 |
| 25 | 75 | 25 |
| 30 | 75 | 25 |
柚皮苷液相检测条件色谱柱采用C18柱，流动相为水和甲醇，比例为71:29，检测波长283nm，流速为1ml/min，进样量5μL，柱温26℃。
橙皮苷液相检测条件色谱柱采用C18柱，流动相为水和甲醇，比例为50：50，检测波长280nm，流速为1ml/min，进样量5μL，柱温26℃。
淫羊藿苷液相检测条件色谱柱采用C18柱，流动相为乙腈和水，其比例为26：74，检测波长270nm，流速为1ml/min，进样量5μL，柱温26℃。
3、转化率结果
转化芦丁进行HPLC检测，反应4h，转化率达到>98.5％，结果见图7；
转化柚皮苷并进行HPLC检测，反应6h，转化率>98.5％，结果见图8；
转化橙皮苷进行HPLC检测，反应8h，转化率>98.5％，结果见图9；
转化朝藿定C生成淫羊藿苷并进行HPLC检测，反应6h，转化率>98.5％，结果见图10。
综上所述，所述碱性嗜热鼠李糖苷酶能够在高温强碱下生物转化芦丁、柚皮苷、橘皮苷，以及朝藿定C等黄酮类化合物，且转化率可达98.5％以上。
最后应说明的是：以上实施例仅用以说明本发明的技术方案，而非对其限制；尽管参照前述实施例对本发明进行了详细的说明，本领域的普通技术人员应当理解：其依然可以对前述各实施例所记载的技术方案进行修改，或者对其中部分技术特征进行等同替换；而这些修改或者替换，并不使相应技术方案的本质脱离本发明各实施例技术方案的精神和范围。
序列表
<110> 北京拓为生物科技有限公司
<120> 一种碱性嗜热鼠李糖苷酶在制备活性生物黄酮中的应用
<160> 1
<170> PatentIn version 3.3
<210> 1
<211> 894
<212> PRT
<213> 人工序列
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Claims (4)
1.一种高转化率的生物转化黄酮类化合物的方法，其特征在于，所述生物转化在高温条件和不同pH条件下进行，在碱性嗜热鼠李糖苷酶的作用下进行黄酮类化合物的生物转化，所述碱性嗜热鼠李糖苷酶的氨基酸序列如SEQ ID NO：1所示，所述黄酮类化合物选自芦丁、柚皮苷、橘皮苷、新橙皮苷或朝藿定C中一种或多种，所述高温条件为80-100℃，所述不同pH条件为pH8-10。
2.根据权利要求1所述的方法，其特征在于，所述高温条件为80℃或100℃。
3.一种碱性嗜热鼠李糖苷酶在高温条件和不同pH条件下生物转化黄酮类化合物中的应用，其特征在于，所述碱性嗜热鼠李糖苷酶的氨基酸序列如SEQ ID NO：1所示，所述黄酮类化合物选自芦丁、柚皮苷、橘皮苷、新橙皮苷或朝藿定C中一种或多种，所述高温条件为80-100℃，所述不同pH条件为pH8-10。
4.根据权利要求3所述的应用，其特征在于，所述高温条件为80℃或100℃。
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104312996A (zh) * | 2014-09-26 | 2015-01-28 | 南京林业大学 | α-L-鼠李糖苷酶Rha1及其表达基因和应用 |
| CN104762281A (zh) * | 2015-03-09 | 2015-07-08 | 南京林业大学 | 一种α-鼠李糖苷酶及其制备方法和应用 |
| CN108467858A (zh) * | 2018-02-05 | 2018-08-31 | 南京林业大学 | 一种α-L-鼠李糖苷酶及其应用 |
| CN112210548A (zh) * | 2020-09-07 | 2021-01-12 | 佛山市汇腾生物技术有限公司 | 一种表达α-L-鼠李糖苷酶的毕赤酵母及其制备方法和应用 |
-
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104312996A (zh) * | 2014-09-26 | 2015-01-28 | 南京林业大学 | α-L-鼠李糖苷酶Rha1及其表达基因和应用 |
| CN104762281A (zh) * | 2015-03-09 | 2015-07-08 | 南京林业大学 | 一种α-鼠李糖苷酶及其制备方法和应用 |
| CN108467858A (zh) * | 2018-02-05 | 2018-08-31 | 南京林业大学 | 一种α-L-鼠李糖苷酶及其应用 |
| CN112210548A (zh) * | 2020-09-07 | 2021-01-12 | 佛山市汇腾生物技术有限公司 | 一种表达α-L-鼠李糖苷酶的毕赤酵母及其制备方法和应用 |
Non-Patent Citations (2)
| Title |
|---|
| alpha-L-rhamnosidase [Caldivirga maquilingensis];无;《GENBANK》;序列部分 * |
| 无.alpha-L-rhamnosidase [Caldivirga maquilingensis].《GENBANK》.2019,序列部分. * |
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