JP6923100B1 - 新規イソフラボン化合物 - Google Patents
新規イソフラボン化合物 Download PDFInfo
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- JP6923100B1 JP6923100B1 JP2021093328A JP2021093328A JP6923100B1 JP 6923100 B1 JP6923100 B1 JP 6923100B1 JP 2021093328 A JP2021093328 A JP 2021093328A JP 2021093328 A JP2021093328 A JP 2021093328A JP 6923100 B1 JP6923100 B1 JP 6923100B1
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- aquaporin
- filaggrin
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Abstract
Description
(1)アクアポリン3遺伝子の発現を亢進させ、アクアポリン3の産生を促進することができる。
(2)フィラグリン2遺伝子の発現を亢進させ、フィラグリン2の産生を促進することができる。
(3)アクアポリン3産生促進作用及びフィラグリン2産生促進作用を備え、相乗的な皮膚バリア機能改善効果を有する。
(4)IL−6産生を抑制し、抗炎症作用を有する。
(5)古来から食用とされているイナゴマメの莢果由来の化合物を有効成分とするものであるため、人体に対する安全性が高い。
1.イナゴマメ莢果の含水アルコール抽出物の調製
採取後、乾燥処理されたイナゴマメ(Ceratonia siliqua)の莢付果実から種を取り除いた。このイナゴマメの莢果を粉砕機で粉砕して粒径2mm以下の粉砕物を得た。20kgの粉砕物に対し、140kg(7倍量)の含水95%エタノールを加え、1.5時間還流抽出する操作を2回行った後、残渣をさらに140kg(7倍量)の含水70%エタノールで1.5時間還流抽出した。得られた還流抽出液を合わせた後、溶媒を減圧留去してイナゴマメ莢果の含水エタノール抽出物12.4kgを得た。
2.イナゴマメ莢果の含水アルコール抽出物の分離及び精製
実施例1で得られたイナゴマメ莢果の含水エタノール抽出物を1〜10倍量の水に分散させ、イオン交換樹脂(マクロポーラス吸着樹脂D101、Cangzhou Bon Adsorber Technology Co., Ltd.)に吸着させた。カラム容量の3倍量の蒸留水で溶出して糖類等の不純物を除去した後、カラム容量の3倍量の含水95%エタノールで溶出させ、溶媒を減圧留去し、462.7gのエタノール溶出画分(非炭水化物系低分子化合物画分)を得た。次に、得られたエタノール溶出画分を1.0Lの含水50%メタノールに分散させ、石油エーテル、酢酸エチルの順に、それぞれ5回ずつ液液抽出を行った。各溶媒を減圧留去して、石油エーテル画分28.4g、酢酸エチル画分139.4g及び水系画分290.2gをそれぞれ得た。
3.化合物(Ceratonia siliqua C)の構造解析
実施例2で得られた化合物、「Ceratonia siliqua C」の構造解析を行った。構造解析にあたり、高分解能質量分析(HR−ESI−MS;正イオンモード)、紫外吸収スペクトル分析、赤外吸収スペクトル分析、1H−NMR、13C−NMR、HMBC、HSQC及びNOESY分析を行った。これらの分析に用いた装置は次のとおりである。
・高分解能質量分析:エレクトロスプレーイオン化四重極飛行時間型質量分析装置(Bruker Daltonics社製品)
・紫外吸収スペクトル分析:紫外可視分光光度計(UV−2401PC、株式会社島津製作所製品)
・赤外吸収スペクトル分析:FT−IR(NEXUS470、Thermo nicolet社製品)
・NMR分析:600MHz核磁気共鳴装置(AVANCE III 600、Bruker社製品)
・性状:黄色粉末
・HR−ESI−MS(positive) m/z:499.1266[M+Na]+
・紫外吸収スペクトル:λmax(MeOH)nm (logε):204.6(4.07),264.2(4.02)
・赤外吸収スペクトル(KBr、cm−1):νmax:3422.30,1651.40,1613.95,1587.91,1516.46,1494.55,1441.21,1366.52,1323.41,1279.56,1265.05,1253.99,1219.53,1182.66,1112.36,1071.83,1055.90,1029.91,1012.41,830.57
加えて、1H−NMRスペクトルの低磁場領域に、イソフラボンに特徴的な芳香族プロトンシグナル[δH:8.24(1H,s,H−2)]が認められることから、本化合物はイソフラボン化合物であることが推定された。
4.Ceratonia siliqua Cの抗炎症作用
実施例2で得たCeratonia siliqua Cを用いて、Ceratonia siliqua Cが炎症性サイトカインであるIL−6の産生に与える影響を調べた。
5.Ceratonia siliqua Cの皮膚バリア機能関連遺伝子の発現促進作用
実施例2で得たCeratonia siliqua Cを用いて、ヒト表皮由来角化細胞株であるHaCaT細胞におけるCeratonia siliqua Cのアクアポリン3(AQP3)及びフィラグリン2(FLG2)の遺伝子発現に与える影響を調べた。
Claims (11)
- 前記式(I)で表される化合物若しくはその塩又はそれらの溶媒和物の濃度が0.001mM〜1mMである請求項2〜5のいずれか1項に記載の剤。
- 皮膚外用剤である請求項2〜6のいずれか1項に記載の剤。
- 化粧料である、請求項2〜7のいずれか1項に記載の剤。
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JP2021093328A JP6923100B1 (ja) | 2021-06-03 | 2021-06-03 | 新規イソフラボン化合物 |
PCT/JP2022/011173 WO2022254868A1 (ja) | 2021-06-03 | 2022-03-14 | 新規イソフラボン化合物 |
EP22815625.3A EP4349845A1 (en) | 2021-06-03 | 2022-03-14 | Novel isoflavone compound |
KR1020237033796A KR20240017336A (ko) | 2021-06-03 | 2022-03-14 | 신규 이소플라본 화합물 |
CN202280030394.8A CN117545761A (zh) | 2021-06-03 | 2022-03-14 | 新型异黄酮化合物 |
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JP2005119999A (ja) * | 2003-10-15 | 2005-05-12 | Sanpo Kk | イナゴマメ抽出物 |
JP2013515704A (ja) * | 2009-12-24 | 2013-05-09 | アイエスピー・インヴェストメンツ・インコーポレイテッド | アクアポリンの発現を活性化するための活性薬剤としてイナゴマメの抽出物を含む、化粧品組成物および/または医薬組成物 |
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