JP2018113946A - Mel−dの製造方法 - Google Patents
Mel−dの製造方法 Download PDFInfo
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- JP2018113946A JP2018113946A JP2017008703A JP2017008703A JP2018113946A JP 2018113946 A JP2018113946 A JP 2018113946A JP 2017008703 A JP2017008703 A JP 2017008703A JP 2017008703 A JP2017008703 A JP 2017008703A JP 2018113946 A JP2018113946 A JP 2018113946A
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Abstract
Description
項1.
下記式(1)の構造を有するMEL−Dを産生する微生物。
(式中、R1は炭素数2〜24の脂肪族アシル基を表す。R2は水素原子、アセチル基又は炭素数2〜24の脂肪族アシル基を表す。R3及びR4は水素原子を表す。)
項2.
R2が水素原子又はアセチル基である、項1に記載の微生物。
項3.
R2が炭素数2〜24の脂肪族アシル基である、項1に記載の微生物。
項4.
マンノースアセチル転移酵素をコードする遺伝子が欠損している、項1〜3のいずれかに記載の微生物。
項5.
微生物がシュードザイマ属に属する、項1〜4のいずれかに記載の微生物。
項6.
微生物がシュードザイマ・ツクバエンシスに属する、項1〜5のいずれかに記載の微生物。
項7.
項1〜6のいずれかに記載の微生物を用いてMEL−Dを製造する方法。
項8.
MEL−DにおけるR2が水素原子又はアセチル基である、項7に記載の方法。
項9.
微生物を植物油脂を含む培地で培養する工程を含む、項7又は8に記載の方法。
項10.
MEL生産能を有する微生物のマンノースアセチル転移酵素をコードする遺伝子を破壊する工程を含む、上記式(1)の構造を有するMEL−D生産微生物を製造する方法。
項11.
MEL生産能を有する微生物がシュードザイマ属微生物である、項10に記載の方法。
項12.
MEL生産能を有する微生物がシュードザイマ・ツクバエンシスに属する微生物である、項10又は11に記載の方法。
項13.
MEL−DにおけるR2が水素原子又はアセチル基である、項10〜12のいずれかに記載の方法。
式中、R1は炭素数2〜24の脂肪族アシル基を表す。R2は水素原子、アセチル基又は炭素数2〜24の脂肪族アシル基を表す。R3及びR4は水素原子を表す。)
上記記載のMEL−Dを生産する微生物が提供される。MEL―Dを生産する微生物の種類は特に制限されない。一実施形態においてMEL−D生産微生物は、シュードザイマ属、モイジオマイセス属、ウスチラゴ属、スポリソリウムに属、Melanopsichium属、又はクルツマノマイセス属に属することが好ましい。好ましいシュードザイマ属微生物は、Pseudozyma antarctica、Pseudozyma parantarctica、Pseudozyma rugulosa、 Pseudozyma siamensis、Pseudozyma shanxiensis、Pseudozyma crassa、 Pseudozyma churashimaensis、Pseudozyma aphidis、Pseudozyma hubeiensis、及びPseudozyma tsukubaensisである。好ましいモイジオマイセス属微生物はMoesziomyces antarcticus、 Moesziomyces aphidisである。好ましいウスチラゴ属微生物は、Ustilago hordei及びUstilago maydisである。好ましいSporisorium属微生物は、Sporisorium reilianum及びSporisorium scitamineumである。好ましいMelanopsichium属微生物は、Melanopsichium pennsylvanicumである。好ましいクルツマノマイセス属微生物は、Kurtzmanomyces sp. I-11である。好適な一実施形態において、MEL産生微生物は、シュードザイマ属微生物であり、より好ましくはPseudozyma tsukubaensisに属する微生物であり、更に具体的には、Pseudozyma tsukubaensis 1E5(JCM16987株)、NBRC1940(ATCC24555、CBS422.96、CBS6389、DBVPG6988、PYCC4855、JCM10324、MUCL29894、NCYC1510、NRRLY-7792)である。Pseudozyma tsukubaensisに属する微生物は、1−O−β−MEL−Bを選択的に生産することが知られている。
MEL−Dは、従来型のMEL−A、B、Cと比較して水への高い親和性を有すると考えられる。よって、従来型のMELが使用される分野(例えば、化粧品及び医薬品)において使用でき、特に親水性が求められる分野での利用に適している。一実施形態において、MEL−Dを含有する皮膚外用剤が提供される。皮膚外用剤の用途は特に制限されないが、例えば、化粧品、医薬部外品、及び/又は医薬品とすることができる。MEL−Dを配合した化粧品としては、例えば、シャンプー、コンディショナー、トリートメントなどの毛髪化粧料、洗顔料、クレンジング化粧料、日焼け止め化粧料、パック、マッサージ化粧料、化粧水、乳液、クリームなどの皮膚化粧料、アイライナー、マスカラ、口紅、ファンデーションなどのメイクアップ化粧料、並びに浴用化粧料等を挙げることができる。
Pseudozyma tsukubaensis 1E5株を1白金耳分YM培地(Yeast extract 0.3%、Malt extract 0.3%、Peptone 0.5%、Glucose 1%) 3mlに植菌し、10ml容量の試験管内で25℃、 180rpmの条件で24時間振とう培養した。培養液をシャーレに広げ、UV灯(Panasonic社製GL15殺菌灯)から45cmの位置にプレートを配置した。UVを照射し、培養液を0.2ml回収した。回収した培養液を25℃で3時間インキュベートし、5FOA plate(Yeast nitrogen base w/o AA 0.67%、-Ura DO supplement 0.078%、Uracil 0.05%、5-FOA 0.2%、Glucose 2%、Agar 1.5%)に塗布植菌した。植菌したプレートを25℃で6日間インキュベートし、コロニーを生育させた。5FOAプレートに生育したコロニーをYNB+5FOA+uracil培地につまようじで植え継ぎ、菌体の一部をcolony PCR及びシーケンス解析に供した。PCRのプライマーには下記の塩基配列を有するものを用いた。
PtURA3coloP_F:AATTAAGCTTCTGTGCGGGGCTCTCCTTCCTCCTT(配列番号4)
PtURA3coloP_R:CCATTGCTTACTTCAGTCTTGTCTGTGAGTGTGC(配列番号5)
PtURA5coloP_F: ACGTCAATTCTCGTCTCAGCCAAGCAAGAAGGCG(配列番号6)
PtURA5coloP_R: ATCATGACTCTTTCTCCCACTTGGCTCTTCTCAAG(配列番号7)
シーケンス解析の結果、URA3遺伝子に変異が挿入されていることを確認した。尚、得られたウラシル要求性変異体の栄養要求性試験を行い、ウラシル要求性、5FOA耐性を有していることを確認した。また、MEL生産能を維持していることも確認した。
2−1.MATベクターの構築
Pseudozyma tsukubaensis 1E5株のゲノムDNAをテンプレートとしたPCRにてMAT1遺伝子領域の増幅を行った。PCRのプライマーには下記の塩基配列を有するものを用いた。
PtMAT1_U2.0K_F:tgtctactcgctcgactttgcccgtacgcgtctag(配列番号8)
PtMAT1_D2.0K_R:caagcactcctgcaagcatcaacactcctgagcat(配列番号9)
増幅したDNA断片をTArget Clone-Plus-(東洋紡製)を用いてTA cloningし、pTA-MAT1ベクターを作製した。
Pseudozyma tsukubaensis 1E5株のゲノムDNAをテンプレートとしたPCRにてURA5遺伝子領域の増幅を行い、URA5遺伝子断片を取得した。PCRのプライマーには下記の塩基配列を有するものを用いた。
PtURA5U1K_F:CCGAAGGTCATGGTGTTCCCGGTGGCTTGCCATAC(配列番号10)
PtURA5D05K_R:ACAAGCCAGATCAAGTTCGTCATGTCGGCGGTGAA(配列番号11)
ついで、pTA-MAT1ベクターをテンプレートとしたPCRにて線状化pTA-MAT1ベクターの増幅を行い、遺伝子断片を取得した。PCRのプライマーには下記の塩基配列を有するものを用いた。
PtMAT1_D2KU5_fF ACGAACTTGATCTGGCTTGTtattactttagctacccatcttcttgcatt(配列番号12)
PtMAT1_U2KU5_fR GGGAACACCATGACCTTCGGaatactcacttgaaagtgcacgcatcaaac(配列番号13)
上記で得られた線状化pTA-MAT1ベクターおよびURA5遺伝子断片をFusion(R) HD Cloning Kit(TAKARA製)に供した後、JM109株(東洋紡製)に形質転換し、pTA-MAT1破壊ベクター(pTA-MAT1del-ura5)を作製した。pTA-MAT1破壊ベクターをシーケンス解析することにより目的断片が挿入されていることを確認した。pTA-MAT1破壊ベクターの構造を図3に示す。
上記2−2.で得られたpTA-MAT1破壊ベクターをPCRで増幅したものを用いて、エレクトロポレーション法にて上記1.で得たウラシル要求性変異株に形質転換した。形質転換体の選別には、ウラシル要求性消失を使用した。目的のDNA断片が相同組み換えによって目的のゲノム位置挿入されたことは、コロニーPCRおよびシーケンス解析にて確認し、MAT1遺伝子が破壊された変異体を3株取得した。
MAT1遺伝子破壊形質転換体2株をそれぞれ3%のグリセロールを含むYM培地60mL(500mL容量坂口フラスコ)で25℃、1日間振とう培養し、前培養液を得た。次いで、前培養液0.2mLをMEL培地に10%オリーブ油を添加した培地20mL(500mL容量坂口フラスコ)に接種し、25℃で7日間振とう培養した。得られた菌体培養液に等量の酢酸エチルを添加し、十分撹拌した後、酢酸エチル層を分取した。酢酸エチル層に含まれるMELは薄層クロマトグラフィーにて確認した。その結果、図4に示される通り、いずれの変異株(#1および#15)についてもMEL−Bの生産は消失し、MEL−BよりもRf値の低い2種類の未知の糖脂質の生産が確認された。
薄層クロマトグラフィーで検出された2種類の未知の糖脂質画分をそれぞれ酢酸エチルにより抽出し、加温減圧により取得した。得られた未知の糖脂質を下記の装置及び条件を用いて構造解析した。
(解析1)
装置:フーリエ変換核磁気共鳴装置(ブルカー・バイオスピン製AVANCE500)
測定溶液:試料10〜100mgを0.6mlの重水素化ジメチルスルホキシド に溶解した。
1H共鳴周波数:500.13MHz
検出パルスのフリップ角:45°
データ取り込み時間:4.0秒
遅延時間:1.0秒
積算回数:43回
測定温度:35℃。
(解析2)
装置:フーリエ変換核磁気共鳴装置(ブルカー・バイオスピン製AVANCE500)
測定溶液:試料10〜100mgを0.6mlの重水素化ジメチルスルホキシド に溶解した。
13C共鳴周波数:125.76MHz
検出パルスのフリップ角:45°
データ取り込み時間:2.0秒
遅延時間:0.5秒
プロトンデカップリング:フルデカップル。
測定温度:室温
積算回数:4096回
Claims (7)
- 下記式(1)の構造を有するMEL−Dを産生する微生物。
(式中、R1は炭素数2〜24の脂肪族アシル基を表す。R2は水素原子、アセチル基又は炭素数2〜24の脂肪族アシル基を表す。R3及びR4は水素原子を表す。) - R2が水素原子又はアセチル基である、請求項1に記載の微生物。
- R2が炭素数2〜24の脂肪族アシル基である、請求項1に記載の微生物。
- 微生物がシュードザイマ属に属する、請求項1〜3のいずれかに記載の微生物。
- 微生物がシュードザイマ・ツクバエンシスに属する、請求項1〜4のいずれかに記載の微生物。
- マンノースアセチル転移酵素をコードする遺伝子が欠損している、請求項1〜5のいずれかに記載の微生物。
- 請求項1〜6のいずれかに記載の微生物を用いて、MEL−Dを製造する方法。
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WO2021039686A1 (ja) * | 2019-08-26 | 2021-03-04 | 国立研究開発法人産業技術総合研究所 | モノアシル型melの製造 |
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JP7475007B2 (ja) | 2020-03-10 | 2024-04-26 | 株式会社クレハ | エルゴチオネインの生産方法 |
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WO2021010264A1 (ja) * | 2019-07-18 | 2021-01-21 | 国立研究開発法人産業技術総合研究所 | バイオサーファクタント産生組換え微生物 |
WO2021039686A1 (ja) * | 2019-08-26 | 2021-03-04 | 国立研究開発法人産業技術総合研究所 | モノアシル型melの製造 |
CN114269942A (zh) * | 2019-08-26 | 2022-04-01 | 国立研究开发法人产业技术综合研究所 | 单酰基型mel的制备 |
CN114787334A (zh) * | 2019-12-12 | 2022-07-22 | 国立研究开发法人产业技术综合研究所 | 单酰基型mel生产菌 |
JP7475007B2 (ja) | 2020-03-10 | 2024-04-26 | 株式会社クレハ | エルゴチオネインの生産方法 |
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