JP5007396B2 - 糖脂質型バイオサーファクタントの脱アシル体の製造方法 - Google Patents
糖脂質型バイオサーファクタントの脱アシル体の製造方法 Download PDFInfo
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- JP5007396B2 JP5007396B2 JP2007022445A JP2007022445A JP5007396B2 JP 5007396 B2 JP5007396 B2 JP 5007396B2 JP 2007022445 A JP2007022445 A JP 2007022445A JP 2007022445 A JP2007022445 A JP 2007022445A JP 5007396 B2 JP5007396 B2 JP 5007396B2
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- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
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- 235000019519 canola oil Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
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- 150000001721 carbon Chemical group 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- HQSBWLQFLLMPKC-UHFFFAOYSA-N dodecadienoic acid Natural products CCCCCCCC=CC=CC(O)=O HQSBWLQFLLMPKC-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
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- 230000008020 evaporation Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000003779 hair growth Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- FIKTURVKRGQNQD-UHFFFAOYSA-N icos-2-enoic acid Chemical compound CCCCCCCCCCCCCCCCCC=CC(O)=O FIKTURVKRGQNQD-UHFFFAOYSA-N 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- XDQQQSFYCSYSCP-UHFFFAOYSA-N kaempferol 3-O-beta-D-glucopyranosyl(1-3)-alpha-L-rhamnopyranosyl(1-6)-beta-D-glucopyranoside Natural products CC=CCCC=CCCC(O)=O XDQQQSFYCSYSCP-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 1
- 229940061634 magnesium sulfate heptahydrate Drugs 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
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- 235000008390 olive oil Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- FCBUKWWQSZQDDI-UHFFFAOYSA-N rhamnolipid Chemical compound CCCCCCCC(CC(O)=O)OC(=O)CC(CCCCCCC)OC1OC(C)C(O)C(O)C1OC1C(O)C(O)C(O)C(C)O1 FCBUKWWQSZQDDI-UHFFFAOYSA-N 0.000 description 1
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- NNNVXFKZMRGJPM-KHPPLWFESA-N sapienic acid Chemical compound CCCCCCCCC\C=C/CCCCC(O)=O NNNVXFKZMRGJPM-KHPPLWFESA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
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- 235000010344 sodium nitrate Nutrition 0.000 description 1
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- 230000008961 swelling Effects 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
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- IBYFOBGPNPINBU-OUKQBFOZSA-N trans-2-tetradecenoic acid Chemical compound CCCCCCCCCCC\C=C\C(O)=O IBYFOBGPNPINBU-OUKQBFOZSA-N 0.000 description 1
- LKOVPWSSZFDYPG-WUKNDPDISA-N trans-octadec-2-enoic acid Chemical compound CCCCCCCCCCCCCCC\C=C\C(O)=O LKOVPWSSZFDYPG-WUKNDPDISA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- 239000007218 ym medium Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Description
本発明の製造方法に用いることのできるMELは、特に制限されるものではないが、微生物を用いた発酵方法を任意に選択して行うことにより製造することができる。微生物としては、例えば、Pseudozyma antarctica NBRC 10736、Candida antarctica、Candida sp.、P.tsukubaensis等を挙げることができるが、これらに限定されるものではない。いずれの微生物でも容易にMELが得られることは周知の事実である。MELを生産する能力を有する微生物としては特に限定するものではなく、目的に応じて適宜使用することができる。
MEL−Dの製造方法では、上述したアセチル基含有MEL(MEL−A、MEL−Bおよび、MEL−C)を好適に用いることができる。これらのアセチル基含有MELの内、1種を単独で用いても良いし、または、2種以上を併用しても良い。
〔MEL−Aの製造〕
種菌培養はPseudozyma antarctica NBRC 10736を種培地(20ml/500ml容坂口フラスコ)に1roop植菌して実施した。30℃にて一晩培養した。得られた培養液を種菌とした。種培地組成は4% Glucose、0.3% NaNO3、0.02% MgSO4・H2O、0.02% KH2PO4、0.1% yeast extractとした。
上述のように製造したMEL−A 1gを下記1〜5の組成の混合溶液50mlに懸濁した。その後、リパーゼLPL−311(東洋紡)1gを添加し30℃で12時間振とうし反応させた。
2−0.1Mリン酸バッファー(pH7.0):メタノール=1:3
3−0.1Mリン酸バッファー(pH7.0):メタノール=1:1
4−0.1Mリン酸バッファー(pH7.0):メタノール=3:1
5−0.1Mリン酸バッファー(pH7.0)
反応後、酢酸エチルで抽出濃縮し、シリカゲル20gを用いて、酢酸エチル:メタノール10:1で生成物を単離し、無色油状の生成物100mgを得た。
〔MEL−Bの製造〕
0.2mlのP.tsukubaensisのフローズンストックをYM種培地(20ml/500ml容坂口フラスコ)に植菌し、26℃、180rpmにて1晩培養した。得られた培養液を種菌とした。
上述のように製造したMEL−B 1gを用いて、実施例1と同様の方法で反応後、精製を行い無色油状の生成物95mgを得た。
Claims (2)
- 式(II)
式(I)
- 上記式(II)において、
(i)R3およびR4はともにアセチル基であるか、または、
(ii)R3がHで、R4がアセチル基である
ことを特徴とする請求項1に記載の糖脂質型バイオサーファクタントの脱アシル体の製造方法。
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