JP2010202602A - 抗肥満剤及び糖尿病改善剤 - Google Patents
抗肥満剤及び糖尿病改善剤 Download PDFInfo
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Abstract
【解決手段】ネムノキの花部、特に、開花初期の花を陽乾させた合歓花の抽出物(Flavonoid)のうち、酢酸エチル又は水の画分に属する、3''-(E)-(3'''-Methoxycaffeoyl)quercitrin又はRhamnetinを含有する抗肥満剤及び糖尿病改善剤。
【選択図】図1
Description
合歓花の成分として、QuercetinやQuercitrinなどのFlavonoidを含有しているものの、前駆脂肪細胞から脂肪細胞への分化作用を持つことは知られていない。
本発明者は、ネムノキに着目して、抗肥満作用、及び糖尿病改選作用を持つ、新規な成分を得ることを、本発明の目的としたものである。
化合物2は3''-(E)-(3'''-Methoxycaffeoyl)quercitrinであり、
化合物3は、2''-(E)-Cinnamoylquercitrinであり、
化合物4は、3''-(E)-Cinnamoylquercitrinであり、
化合物5はQuercetinであり、
化合物6は、Isorhamnetinであり、
化合物7はRhamnetinであり、
化合物8はQuercitrinであり、
化合物9はKaempferolであり、
化合物10はAfzeleinであり、
化合物11はChrysoeriolであり、
化合物12はApigeninであり、
化合物13はTricinであり、
化合物14はLuteolinであり、
化合物15はAmentoflavoneであり、
化合物16はTaxifolinであり、
化合物17はIsoliquiritigeninであり、
化合物18は、α-Spinasterol-3-O-β-D-glucopyranosideであり、
化合物19は、(6S)-Menthiafolic acid であり、
化合物20は3,3'-Dithiodipropanoic acidであり、
化合物21はIndole-3-carboxylic acidであり、
化合物22は7,8-Dimethylalloxazineであり、そして、
化合物23は(E)-p-Coumaric acidである。
酢酸エチル溶出画分 (165.5 g) をSilica gelカラム (12.5 φ×21 cm) に付し、CHCl3:MeOH = 100:0〜0:100で溶出し、AJE-A〜Bに分画した。この際、析出してきた沈殿物をろ取し、再結晶することにより、化合物18 (423.8 mg) を得た (Fig.2) 。
AJCをSilica gelカラム (12φ×20 cm) に付し、Hexane:EtOAc = 100:0〜0:100で溶出し、AJC-A〜Oに分画した。そのうちAJC-GをSilica gelカラム (3.5φ×20 cm) に付し、CHCl3:MeOH = 100:0〜0:100で溶出しAJC-G1〜5に分画した (Fig.12) 。さらにAJC-G3をHPLC (COSMOSIL 5C18-MS-II 10φ×250 mm、H2O:MeOH = 57:43) をかけ、化合物19 (342 mg、保持時間13m00s) を得た (Fig.13) 。
化合物1(3''-(E)-p-Coumaroylquercitrin)
化合物1は黄色粉末で得られ、[α]25D -146°を示し、Negative FAB-MSからm/z 593 [M-H]-、HR-FAB-MSではm/z 593.1301 (calcd. 593.1294) に疑似分子イオンピークを示すことから、分子式C30H26O13が推定された。IRでは3378 cm-1に水酸基に基づく強い吸収、1654 cm-1にカルボニル基、1603 cm-1に共役二重結合に基づく吸収が観測された。UVスペクトルでは267 nmと315 nmに極大吸収が観測され、flavonoid誘導体が推定された(図5)。
化合物2は黄色粉末で得られ、 [α]25D -158°を示し、Negative FAB-MSからm/z 623 [M-H]-、HR-FAB-MSではm/z 623.1398 (calcd. 623.1399) に疑似分子イオンピーク示すことから、分子式C31H27O14が推定された。IRでは3422 cm-1に水酸基に基づく強い吸収、1653 cm-1カルボニル基、1603 cm-1に共役二重結合に基づく吸収が観測された。UVスペクトルでは267 nmと333 nmに極大吸収が観測され、flavonoid誘導体が推定された(図5)。
以上の結果より、化合物2は3''-(E)-(3'''-Methoxycaffeoyl)quercitrinと決定した。
化合物3は黄色粉末で得られ、 [α]25D -143° を示し、Negative FAB-MSからm/z 577 [M-H]-、HR-FAB-MSではm/z 577.1350 (calcd. 577.1345) に疑似分子イオンピーク示すことから、分子式C30H26O12が推定された。IRでは3418 cm-1に水酸基に基づく強い吸収、1652 cm-1にカルボニル基、1606 cm-1に共役二重結合に基づく吸収が観測された。UVスペクトルでは267 nmと333 nmに極大吸収が観測され、flavonoid誘導体が推定された(図5参照)。
さらに、13C-NMRスペクトル、DEPTスペクトル、HMQCスペクトル、及び、HMBCスペクトルの結果を利用して、化合物3の構造を解析した。
化合物4は黄色粉末で得られ、 [α]25D -125° を示し、Positive FAB-MSからm/z 579 [M+H]+、HR-FAB-MSではm/z 579.1496 (calcd. 579.1501) に疑似分子イオンピークを示すことから、分子式C30H26O12が推定された。IRでは3422 cm-1に水酸基に基づく強い吸収、1653cm-1にカルボニル基、1607cm-1に共役二重結合に基づく吸収が観測された。UVスペクトルでは270 nmと340 nmに極大吸収が観測されたことから、flavonoid誘導体が推定された(図5)。
さらに、13C-NMRスペクトル、DEPTスペクトル、HMQCスペクトル、及び、HMBCスペクトルの結果を利用して、化合物4の構造を解析した。
1)3T3-L1前駆脂肪細胞から脂肪細胞への分化誘導及び促進試験
3T3-L1前駆脂肪細胞は、5% CO2下37℃で培養した。脂肪細胞分化抑制試験には対数増殖期の細胞を1.0×105 cells/ mLに調製し使用した。基本培地(10% FCSを含むDMEM培地)で2日間培養後(Day 0)、3-イソブチル-1-メチルキサンチン(IBMX, 500 μM)、デキサメタゾン(DEX, 1 μM)及びインスリン(10 μg/mL)を含有する分化誘導培地(10% FBSを含むDMEM培地)に試験薬物を添加し、3日間培養した(Day 3)。さらに、インスリン(10 μg/mL)を含有する分化維持培地に試験薬物を添加し、2日おきに同じ培地で交換し8日間培養した(Day 8)。分化した細胞の上清はチュープに回収し、脂肪細胞はリン酸緩衝生理食塩水(PBS(−))で2回洗浄した。1 mM EDTAを含むトリス−塩酸緩衝液25 mM Tri buffer ( pH 7.5) 500μlを加え、細胞を剥離し、1.5mlプラスチックチューブに回収した。氷水で冷やしながら、超音波処理により細胞膜を破壊後、4℃、15,000rpm、2分間遠心分離を行った。
細胞ホモジネートの一部分を取って、細胞内に蓄積されたトリグリセライド(TG)はラボアッセイトリグリセライド(和光純薬)を用いて定量した。
各サンプルの細胞ホモジネートにトリグリセライド発色試薬を添加してよく混合し、37℃で5分間加温した。ブランクを対照として、波長595 nmにおける検体及び基準液の吸光度を測定した。次式により抑制率を算出した。
X:試料を添加した際の1wellあたりのTG量を1wellあたりのDNA量で除したもの
Y:DMSOを添加した際の1wellあたりのTG量を1wellあたりのDNA量で除したもの。
3)グリセロール3リン酸脱水素酵素(GPDH)活性
細胞ホモジネートの一部分を取って、GPDHはGPDH活性測定キット(Primary Cell Co., Ltd.)を用いた。
検体1ml当りのGPDHが1分間に1μMのNADHを消費する活性を1Uとし、GPDH活性を次式で求めた(光路長が1cmの場合)。
ΔO.D.:1分間当たりの波長340nmにおける吸光度の変化量
抑制率 (%) = {(Y - X) / Y}× 100
X:試料を添加した際の1wellあたりのGPDH活性を1wellあたりのDNA量で除したもの
Y:DMSOを添加した際の1wellあたりのGPDH活性を1wellあたりのDNA量で除したもの。
細胞ホモジネートの一部分を取って、細胞内のDNAの量はDNA活性測定キット(Primary Cell Co. Ltd.)を用いて定量した。この結果、合歓花の抽出液、さらに、各画分について、TG蓄積抑制試験とGPDH活性試験を行ったところ、図2に示す通り、水画分及び酢酸エチル画分に強い効果が認められた。結果は、±SD(n=3)法で示されている。サンプルの濃度は30 μg/mlである。
Claims (4)
- ネムノキの花部の抽出物を含有する、抗肥満剤又は糖尿病改善剤。
- 前記花部が合歓花である、請求項1記載の前記薬剤。
- 前記抽出物が、前記花部の酢酸エチル又は水の画分に属する、請求項2記載の前記薬剤。
- 前記抽出物が、3''-(E)-(3'''-Methoxycaffeoyl)quercitrin又はRhamnetinを含む、請求項2記載の前記薬剤。
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JP2009051357A JP5610179B2 (ja) | 2009-03-04 | 2009-03-04 | 抗肥満剤及び糖尿病改善剤 |
PCT/JP2010/001515 WO2010100933A1 (ja) | 2009-03-04 | 2010-03-04 | 抗肥満剤及び糖尿病改善剤 |
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JP2009051357A JP5610179B2 (ja) | 2009-03-04 | 2009-03-04 | 抗肥満剤及び糖尿病改善剤 |
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JP2010235548A (ja) * | 2009-03-31 | 2010-10-21 | Maruzen Pharmaceut Co Ltd | 抗酸化剤、抗炎症剤、美白剤、抗老化剤、育毛剤、及び抗肥満剤、並びに化粧料、及び飲食品 |
JP2017019737A (ja) * | 2015-07-09 | 2017-01-26 | 学校法人日本大学 | 小胞体ストレスによる細胞死抑制剤、小胞体ストレス制御剤、および該制御剤を有効成分とする予防・治療剤 |
CN110872267A (zh) * | 2018-08-30 | 2020-03-10 | 复旦大学 | 一种从构树中提取的化合物及其在制备蛋白酪氨酸磷酸酶1b抑制剂中的用途 |
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KR101740116B1 (ko) * | 2014-04-07 | 2017-05-25 | 경희대학교 산학협력단 | 신규 5,6-다이하이드로에르고스테롤 글리코시드 유도체를 포함하는 조성물 |
TWI747984B (zh) * | 2016-10-27 | 2021-12-01 | 日商三得利控股股份有限公司 | PGC-1α活性化用組成物 |
CN106883278A (zh) * | 2017-03-21 | 2017-06-23 | 广东药科大学 | 一种3,5,7‑三羟基‑2‑(4‑羟基苯基)‑苯并吡喃‑4‑酮衍生物 |
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WO2007111401A1 (en) * | 2006-03-24 | 2007-10-04 | Jong Hyun Nam | Natural plant extract composition for prevention and recovery of hyperlipidemia and stroke, natural tea containing the same as active ingredient and method for preparing the natural tea |
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WO2007111401A1 (en) * | 2006-03-24 | 2007-10-04 | Jong Hyun Nam | Natural plant extract composition for prevention and recovery of hyperlipidemia and stroke, natural tea containing the same as active ingredient and method for preparing the natural tea |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010235548A (ja) * | 2009-03-31 | 2010-10-21 | Maruzen Pharmaceut Co Ltd | 抗酸化剤、抗炎症剤、美白剤、抗老化剤、育毛剤、及び抗肥満剤、並びに化粧料、及び飲食品 |
JP2017019737A (ja) * | 2015-07-09 | 2017-01-26 | 学校法人日本大学 | 小胞体ストレスによる細胞死抑制剤、小胞体ストレス制御剤、および該制御剤を有効成分とする予防・治療剤 |
CN110872267A (zh) * | 2018-08-30 | 2020-03-10 | 复旦大学 | 一种从构树中提取的化合物及其在制备蛋白酪氨酸磷酸酶1b抑制剂中的用途 |
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