JPWO2015029473A1 - 化合物、医薬品、抗炎症剤、化粧品、飲食品及び化合物の製造方法 - Google Patents
化合物、医薬品、抗炎症剤、化粧品、飲食品及び化合物の製造方法 Download PDFInfo
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Classifications
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- A—HUMAN NECESSITIES
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- A61K36/18—Magnoliophyta (angiosperms)
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- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
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- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
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Abstract
Description
下記式(I)又は(II)
下記式(I)、(II)又は(III)
下記式(I)、(II)又は(III)
下記式(I)、(II)又は(III)
下記式(I)、(II)又は(III)
シソ科植物を抽出処理する工程を含む。
シソの葉から8−hydroxy−6,7−dimethoxyflavanone(Pa5)を抽出し、精製した。
アオジソ(Perilla frutescens f.viridis)の葉4.40kgを用いて、メタノール44.3Lによる還流抽出(1時間)を2回行った。2回の還流抽出により得られたメタノール抽出液を減圧濃縮し、メタノール抽出エキス772gを得た(17.5%)。メタノール抽出エキス772gを水3.9Lに懸濁し、酢酸エチル3.9Lを用いた分配抽出を3回行った。3回の分配抽出により得られた酢酸エチル抽出液を合併し、減圧濃縮して、酢酸エチル可溶部254.7gを得た。
mp 166−168°C
[α]23 D0(c1.03,MeOH)
IR ν(KBr)cm−1:3290(OH),1672(C=O),1605(aromatic ring)
UV λmax(MeOH)nm(ε):201(27074),244(11253),288(13489),349(5085)
ESI−MS m/z:301[M+H]+,197
Positive HR−ESI−MS m/z 301.1068[M+H]+,Calcd for C17H17O5:301.1076.
CD(c=0.00114,MeOH)Δε(nm):0(220−400)
1H−NMR δ in CDCl3:2.85(1H,dd,J=16.5,2.8Hz),3.08(1H,dd,J=16.5,12.8Hz),3.92(3H,s,OCH3),4.02(3H,s,OCH3),5.03(1H,s,disappeared with D2O),5.46(1H,dd,J=12.8,2.8Hz),6.19(1H,s,H−5),7.41−7.49(5H,m).
13C−NMR δ in CDCl3:45.8(C−3),56.2(OCH3),56.3(OCH3),80.0(C−2),89.6(C−5),105.7(C−4a),126.3(C−2’,C−5’),127.6(C−8a),128.85(C−3’,C−5’),128.89(C−4’),138.3(C−1’),149.4(C−8),152.5(C−7),155.0(C−6),189.4(C−4).
アオジソ(Perilla frutescens f.viridis)の葉0.6kgを水1Lで加熱還流抽出(1時間)した。冷却後、抽出液をろ紙(アドバンテック定性ろ紙No.2)でろ過した。このようにして得られた熱水抽出液9.5Lを、酢酸エチル9.5Lを用いて、分配抽出を3回行った。3回の分配抽出により得られた酢酸エチル抽出液を合併し、減圧濃縮して、酢酸エチル可溶部8.78gを得た。
シソの葉から5,8−dihydroxy−7−methoxyflavanone(Pa5’)を抽出し、精製した。
アオジソ(Perilla frutescens f.viridis)の葉4.40kgを用いて、メタノール44.3Lによる還流抽出(1時間)を2回行った。2回の還流抽出により得られたメタノール抽出液を減圧濃縮し、メタノール抽出エキス772gを得た(17.5%)。メタノール抽出エキス772gを水3.9Lに懸濁し、酢酸エチル3.9Lを用いた分配抽出を3回行った。3回の分配抽出により得られた酢酸エチル抽出液を合併し、減圧濃縮して、酢酸エチル可溶部254.7gを得た。
Yellow needles (from MeOH).mp 220−225℃.
UV λmax(MeOH)nm(logε):246(3.97),292(4.16),364(3.62)nm.
[α]23 D0(c0.253,MeOH)CD(c=0.00172,MeOH)Δε(nm):0(220−400)
Positive MALDI−TOF−MS(matrix:adipic acid.):m/z(%):287.30([M+H]+,100),288.30(17),289.31(3).
1H−NMR(DMSO−d6) δ2.78(1H,dd,J=16.9,3.2Hz),and 3.19(1H,dd,J=16.9,12.4Hz)(H−3),3.77(3H,s,OCH3),5.51(1H,dd,J=12.4,3.2Hz,H−2),6.15(1H,s,H−7),7.35(2H,m,H−3’,−5’),7.36(1H,m,H−4’),7.48(2H,m,H−2’,−6’),8.15(1H,s,OH),11.74(1H,s,OH).
13C−NMR(DMSO−d6) δ42.7(C−3).56.4(OCH3),78.6(C−2),92.8(C−6),102.6(C−4),126.9(C−2’,6’),128.66(C−3’,−5’,128.72(C−4’),139.1(C−1’),148.3(C−8a),156.0(C−5),157.5(C−8),197.2(C−4).
アオジソ(Perilla frutescens f.viridis)の葉0.6kgを水1Lで加熱還流抽出(1時間)した。冷却後、抽出液をろ紙(アドバンテック定性ろ紙No.2)でろ過した。このようにして得られた熱水抽出液9.5Lを、酢酸エチル9.5Lを用いて、分配抽出を3回行った。3回の分配抽出により得られた酢酸エチル抽出液を合併し、減圧濃縮して、酢酸エチル可溶部8.78gを得た。
シソの葉からEsculetin(Pa9)を抽出し、精製した。
アオジソ(Perilla frutescens f.viridis)の葉4.40kgを用いて、メタノール44.3Lによる還流抽出(1時間)を2回行った。2回の還流抽出により得られたメタノール抽出液を減圧濃縮し、メタノール抽出エキス772gを得た(17.5%)。メタノール抽出エキス772gを水3.9Lに懸濁し、酢酸エチル3.9Lを用いた分配抽出を3回行った。3回の分配抽出により得られた酢酸エチル抽出液を合併し、減圧濃縮して、酢酸エチル可溶部254.7gを得た。
mp 255−258°C
UV λmax(MeOH)nm(log ε):228(4.00),259(3.61),299(3.65),347(3.81)
Negative MALDI−TOF−MS m/z(%):177.24([M−H]−,100),178.24(15).
1H−NMR δ in MeOH−d4:6.17(1H,d,J=9.6Hz),6.75(1H,s),6.93(1H,s),7.78(1H,d,J=9.6Hz).
アオジソ(Perilla frutescens f.viridis)の葉0.66kgを水11Lで加熱還流抽出(1時間)した。冷却後、抽出液をろ紙(アドバンテック定性ろ紙No.2)でろ過した。このようにして得られた熱水抽出液9.5Lを、酢酸エチル9.5Lを用いて、3回分配抽出した。3回の分配抽出により得られた酢酸エチル抽出液を合併し、減圧濃縮して、酢酸エチル可溶部8.78gを得た。
Pa5の抗炎症作用を検証するために、一酸化窒素(NO)産生抑制作用を調べた。
Pa5及びPa5’の各種炎症性サイトカイン/ケモカイン産生に及ぼす影響について、サイトカイン/ケモカインアレイ(in vitro)により検証した。
(1)CINC−2α/β及び(2)CINC−3
CINC(cytokine−induced neutrophil chemoattractant)(サイトカイン誘導性好中球走化性因子)は、ケモカインのアルファ(CXC)サブファミリーに属する。CINC−1をはじめ、3つのラットCXCケモカイン(CINC−2α、CINC−2β、CINC−3/MIP−2)が同定されている。好中球浸潤は代表的な急性期の炎症反応であり、好中球はCINCsの刺激を受けて速やかに形態変化を起こす。in vitroで検討された結果、各CINCの走化性活性に本質的な差はなく、in vivoにて好中球に特異的な強い走化性活性を示す。CINCの発現を抑制することで局所炎症における好中球の浸潤が抑制され、炎症症状の緩和が期待される。
(3)Fractalkine(CX3CL1)
活性化血管内皮細胞、神経細胞、樹状細胞及び腸管上皮細胞で発現している。炎症系サイトカインであるTNFα、IL−1やIFNγなどの炎症性刺激により、CX3CL1の発現が誘導される。生体内では膜結合型及び分泌型の二つの形態をとり、ケモカインとしてのみならず、インテグリン非依存的に細胞接着能を示す細胞接着分子としても機能する。分泌型ケモカインは、NK細胞、T細胞及び単球に対して細胞遊走活性を示す。CX3CL1は、血管新生作用も有する。フラクタイン−CX3CR1の発現は関節リウマチや動脈硬化など様々な疾患に関与することが知られている。CX3CL1を阻害することで、滑膜組織への炎症細胞浸潤を抑制することができ、関節リウマチ等の関節炎をはじめとする炎症を抑制することが期待される。
(4)sICAM−1(CD54)
CD54(ICAM−1:Intercellular Adhesion Molecule 1)は、免疫グロブリンスーパーファミリーに属する接着分子、膜貫通型糖タンパク質で、多くの細胞において恒常的に発現している。CD54は細胞接着分子LFA−1(リンパ球機能関連抗原1)と結合し、炎症や免疫応答での細胞間相互作用に重要な役割を果たしている。ICAMのうちsICAM(soluble Intercellular Adhesion Molecule)はICAMを介した免疫反応を制御しており、自己免疫疾患、内分泌疾患、胃癌、膵臓癌、乳癌などで発現が上昇することが知られており、これによって癌細胞への細胞障害性T細胞、ナチュラルキラー細胞による攻撃が抑制され、癌転移が促進されると考えられている。
(5)MIG(CXCL9)
CXCL9は、14kDaのケモカインで、CXCケモカインファミリーの一員である。CXCL9は、マクロファージや単球、好中球、APC、B細胞や好酸球において特異的に誘導され、その誘導メカニズムはIFNγ−JAK、STATシグナル伝達パスウェイを介する。そのため、インターフェロンγで誘導される単球性サイトカイン、Monokine induced by gamma interferon(MIG)とも呼ばれる。また、静脈内皮細胞や皮膚線維芽細胞においてはTNFαによってCXCL9の誘導が促進される。CXCL9は、腸管上皮でも構成的に発現している。このケモカインの主要な機能は、感染や炎症個所への白血球のリクルートであり、グラム陰性あるいは陽性細菌の感染によってCXCL9が活性化することが、いくつかの研究で報告されている。CXCL9は関節リウマチなどの免疫応答や、慢性炎症に密接に関与している。CXCL9の発現はまた、T細胞のリクルートと活性化のメディエーターとして、乾癬や肺疾患においても機能している可能性があると考えられる。皮膚移植数日後、拒絶反応の前にも発現している。
(6)VEGF(VEGF−A/vasculotropin)
Vascular endothelial growth factor(VEGF)は、血管新生に関わる因子のひとつであり、固形がんの増殖において重要な役割を果たしている。VEGF−Aは、血管内皮細胞に対する増殖因子及び血管透過性の亢進因子の2つの性質を持っている。VEGF−Aの遺伝子発現は、増殖因子やエストロゲン、低酸素などにより誘導される。VEGFの阻害が固形がん治療の戦略として正しいことは、VEGFに特異的に結合し、その機能を阻害する抗体医薬ベバシズマブが優れた延命効果を示すことなどから証明されている。さらに関節リウマチのマウスモデルや、動脈硬化モデルなどにおいても、VEGF系の関与が示されつつある。VEGFRは炎症細胞の動員や機能活性化を介して炎症に深く関わるとされ、この発現を抑えることは抗炎症作用につながると言える。
(7)IL−17
IL−17(IL−17A)は、CTLA−8としてマウス活性化T細胞cDNAライブラリーから同定されたサイトカインである。IL−17の作用としては、IL−6、G−CSF、CXCL1、CXCL8(ヒトのみ)等の主に好中球の活性化、遊走に関わるサイトカイン/ケモカイン及びβ−DefensinやS100ファミリー等の抗菌ペプチドの発現誘導が知られている。コラーゲン誘導関節炎や自己免疫性脳脊髄炎などの自己免疫疾患が、IFN−γやIL−12欠損マウスでは抑制されずむしろ増悪化するのに対し、IL−17欠損マウスにより強く抑制され、抗IL−17抗体を用いたヒト臨床試験で関節リウマチや乾癬における有効性が示されたことから、IL−17発現抑制は炎症性疾患の改善に有効であることが示唆される。
(8)Thymus Chemokine(CXCL7)
CXCL7は主に血小板から活性化に伴って産生され、好中球や好塩基球、線維芽細胞、単球の遊走を促進し、線維芽細胞の増殖やヒアルロン酸、グリコサミノグリカン、PGE2などの分泌を促進する。また好塩基球からのヒスタミン遊離を促進する。CXCL7発現抑制は好中球などの浸潤を抑制し、ヒスタミン遊離促進を防ぐので、抗炎症性に働くことが示唆される。
Pa9の抗炎症作用を検証するために、一酸化窒素(NO)産生抑制作用を調べた。
Claims (7)
- 下記式(I)又は(II)
- 下記式(I)、(II)又は(III)
- 下記式(I)、(II)又は(III)
- 下記式(I)、(II)又は(III)
- 下記式(I)、(II)又は(III)
- シソ科植物を抽出処理することで得られる、
ことを特徴とする下記式(I)、(II)又は(III)
- シソ科植物を抽出処理する工程を含む、
ことを特徴とする下記式(I)、(II)又は(III)
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JPH0662795A (ja) * | 1992-08-21 | 1994-03-08 | Amino Atsupu Kagaku:Kk | 抗アレルギー食品 |
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