JP2011173837A - マスティックを原料とする抗真菌剤 - Google Patents
マスティックを原料とする抗真菌剤 Download PDFInfo
- Publication number
- JP2011173837A JP2011173837A JP2010039855A JP2010039855A JP2011173837A JP 2011173837 A JP2011173837 A JP 2011173837A JP 2010039855 A JP2010039855 A JP 2010039855A JP 2010039855 A JP2010039855 A JP 2010039855A JP 2011173837 A JP2011173837 A JP 2011173837A
- Authority
- JP
- Japan
- Prior art keywords
- antifungal agent
- mastic
- squalene
- antifungal
- extract
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000013521 mastic Substances 0.000 title claims abstract description 38
- 229940121375 antifungal agent Drugs 0.000 title claims abstract description 35
- 239000003429 antifungal agent Substances 0.000 title claims abstract description 29
- 239000002994 raw material Substances 0.000 title description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims abstract description 54
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 claims abstract description 38
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229940031439 squalene Drugs 0.000 claims abstract description 38
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000000284 extract Substances 0.000 claims abstract description 17
- 239000000126 substance Substances 0.000 claims abstract description 15
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 claims abstract description 9
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- 239000007787 solid Substances 0.000 claims abstract description 6
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- YZIYKJHYYHPJIB-UUPCJSQJSA-N chlorhexidine gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(Cl)=CC=C1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC1=CC=C(Cl)C=C1 YZIYKJHYYHPJIB-UUPCJSQJSA-N 0.000 claims description 3
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Abstract
【解決手段】マスティックあるいはマスティックの抽出成分とスクアランとを含む抗真菌剤であり、ヤシ油、ミツロウ、スクワレンの中から選択される1種類または複数種をさらに含み、固体状、ゲル状、クリーム状、軟膏または液状物である抗真菌剤。該マスティック抽出成分中の活性成分は、下記構造式に代表されるoleanane型トリテルペンおよびtirucallane型トリテルペンなどである。
【選択図】なし
Description
(1)マスティックあるいはマスティックの抽出成分とスクアレンとを含む抗真菌剤。
(2)ヤシ油、ミツロウ、スクアレンの中から選択される1種類または複数種をさらに含み、固体状、ゲル状、クリーム状、軟膏または液状物であることを特徴とする(1)に記載の抗真菌剤。
(3)スクアレン、ヒノキチオール、黄伯、黄連、黄岑、ヒバ油、馬油、イソプロパノール、グルコン酸クロルヘキシジン、エタノール、トリクロサン、クロルキシレノール、イソプロピルメチルフェノール、塩化ベンザルコニウム、ヒアルロン酸ナトリュウムの中から選択された1種または複数種をさらに含む(1)または(2)に記載の抗真菌剤。
(4)抗酸化劣化抑制剤としてスクアレン、コエンザイムQ10,αリポ酸、ビタミンP、ビタミンE、γ−オリザノール、β−カロチン、タンニン、ビタミンC、ヘム鉄の中から選択された1種または複数種をさらに含む(1)、(2)、(3)のいずれかに記載の抗真菌剤。
(5)(1)、(2)、(3)、(4)のいずれかに記載の抗真菌剤をカプセル剤、錠剤にし、また該製品を乳化させ、固める為の固化成形用の乳化剤、可塑剤を配合し、固体剤、クリーム剤、軟膏剤、または液剤としたことを特徴とする抗真菌剤。
(6)前記固化成形用の乳化剤がヤシ油、前記可塑剤がミツロウ、スクアレンであることを特徴とする(5)に記載の抗真菌剤。
(1)沸点 340〜350℃、248℃(5mmHg)。
(2)凝固点 −75℃ 一時間保つも透明。
(3)粘性率37.6cp(25℃)無色透明、低粘度、低融怠の液体(常温)、無味無臭。濃硫酸と70℃に加熱しても着色しない。
(1)内科 胃潰瘍、十二指腸潰瘍の治療・予防、高血圧症の血圧低下、糖尿病の血糖降下作用、コレステロール低下作用、免疫力の増強、各種ガンの予防効果、胆汁分泌の促進、胆石の溶解作用、舌苔の予防、通風、リウマチの痛みの緩和等。
(2)歯科 歯槽膿漏の予防・治療、歯周病の予防・治療、歯垢の抑制、歯茎からの出血の防止、筋肉の強化。
(3)外科的治療予防、創傷治癒の促進、褥瘡などの皮膚潰瘍の治癒。
マスティック樹脂(20.5g)を乳鉢で粉砕後、ノルマルヘキサン(400mL)とメタノール(400mL)で溶液分配した。ノルマルヘキサン層とメタノール層を分液ロートで分離後、メタノール層について再度ノルマルヘキサン(300mL)で3回同様の分離操作を行った。ノルマルヘキサン層(約900mL)とメタノール層(約650mL)をエバポレーターにて40度で減圧濃縮し、ノルマルヘキサンエキス(11.5g)とメタノールエキス(8.0g)を得た。
ノルマルヘキサンエキス(1.02g)についてシリカゲル(約70g、Silica gel 60, Merck)によるカラムクロマトグラフィー(内径2.5cm、高さ30cm)を行った。カラム溶出溶媒として、ノルマルヘキサン/酢酸エチル(10/1)を1.1L、次に、0.8Lnoノルマルヘキサン/酢酸エチル(7/1)を使用した。約10mLを試験管で分画し、薄層クロマトグラフィー(TLC)により溶出物質をモニターし、分画後エバポレーターで濃縮し9個のフラクション[Fr.1(32.3mg)、Fr.2(1.7mg)、Fr.3(38.3mg)、Fr.4(37.1mg),Fr.5(26.4mg),Fr.6(22.8mg),Fr.7(19.0mg)、Fr.8(34.8mg),Fr.9(522.7mg)]を得た。更に、Fr.5(26.4mg)を逆相HPLC[カラム:Cosmosil AR-II,C18,内径4.6mm,長さ250mm,Nakarai,溶媒:メタノール、流速 1.0mL/min,UV220]で分離し、Fr.5−1(5.3mg),Fr.5−2(2.1mg)を得た。
分画した各成分について、ガスクロマトグラフ質量分析計(GC−MS,島津QP5050A)及び核磁気共鳴装置(NMR,バリアンUnity600)を用い構造解析を行った。
上記の化学式1は3-oxo-28-norolean-16,18-dienの化学構造式
Fr.1 EIMS(m/z) 408(M+), 393(M-15), 207; 1H-NMR(CDCl3, 600MHz) 0.77(3H,s), 0.95(3H,s), 0.96(3H,s), 0.97(6H,s), 1.01(6H,s), 1.07(3H,s), 5.15(1H, brs) ,5.28(1H, m); 13C-NMR (CDCl3, 150MHz) 14.5, 16.3,16.6,19.5, 21.0, 21.1, 25.1, 26.9, 27.9, 28.8, 29.8, 31.0, 32.6, 32.9, 33.8, 34.1, 36.8, 37.4, 38.0, 39.7, 40.1, 41.3, 47.3, 49.8, 54.8, 120.2, 131.9, 132.5, 134.9,218.1
上記の化学式2はoleanoic aldehydeの化学構造式
Fr.3 EIMS(m/z) 438(M+), 409(M-29), 203(base peak); 1H-NMR(CDCl3, 600MHz) 0.77(3H,s), 0.89(3H,s), 0.90(3H,s), 1.02(6H,s), 1.06(3H,s), 1.13(3H,s), 5.33(1H, brs), 9.37(1H,s) ; 13C-NMR (CDCl3, 150MHz) 15.1, 17.0, 19.6, 21.5, 22.1, 23.4, 23.5, 25.4, 26.5, 26.7, 27.7, 30.6, 32.3, 33.0, 33.2, 34.1, 36.7, 39.2, 39.6, 40.5, 41.8, 45.6, 46.8, 47.4, 49.1, 55.3, 123.0, 143.1, 207.3, 218.0
上記の化学式3はTirucallolの化学構造式
Fr.5−1 EIMS(m/z) 426(M+), 411(M-15), 393(M-15-18), 69(base peak); 1H-NMR(CDCl3, 600MHz) 0.74(3H,s), 0.78(3H,s), 0.85(3H,brs), 0.89(3H,d), 0.94(3H,s), 0.95(3H,s), 0.98(3H,s), 1.58(3H,s), 1.66(3H,s), 3.21(1H,dd), 5.08(1H,brd); 13C-NMR (CDCl3, 150MHz) 15.4, 15.5, 17.6, 18.7, 18.9, 20.1, 21.5, 24.4, 24.9, 25.7, 27.7, 28.0, 28.1, 29.8, 30.8, 35.3, 36.3, 36.4, 37.3, 38.9, 44.1, 50.0, 50.1, 51.0, 79.0, 125.3, 130.6, 133.2, 133.8
上記の化学式4はβ−amyrinの化学構造式
Fr.5−2 EIMS(m/z) 426(M+), 411(M-15), 393(M-15-18), 218(base peak), 203; 1H-NMR(CDCl3, 600MHz) 0.77(3H,s), 0.82(3H,s), 0.85(6H,brs), 0.92(3H,s), 0.95(3H,s), 0.98(3H,s), 1.11(3H,s), 3.20(1H,dd, 4.6, 11.2Hz), 5.16(1H, brt).
上記の化学式5は3-oxo-17-hydroxy-norolean-12-enの化学構造式
Fr.6 EIMS(m/z) 426(M+), 409(M-17),394, 281, 253, 207, 202, 55(base peak); 1H-NMR(CDCl3, 600MHz) 0.88(3H,s), 0.95(3H,s), 0.97(3H, s), 1.04(3H,s), 1.04(3H,s), 1.08(3H,s), 1.12(3H,s),5.20(1H, brs); 13C-NMR (CDCl3, 150MHz) 15.0, 17.0, 19.6, 21.5, 23.3, 23.6, 23.9, 25.3, 25.5, 26.5, 31.0, 31.2, 32.4, 32.5, 34.2, 36.0, 36.8, 39.1, 39.5, 41.7, 42.8, 47.0, 47.4, 48.3, 55.4, 84.2, 122.3, 143.7, 217.7
上記の化学式6は3-oxo-20-hydroxy-dammar-24-enの化学構造式
Fr.8 EIMS(m/z) 424(M+-18), 409, 355, 109(base peak); 1H-NMR(CDCl3, 600MHz) 0.87(3H,s), 0.93(3H,s), 0.98(3H, s), 1.02(3H,s), 1.06(3H,s), 1.13(3H,s), 1.61(3H,s), 1.67(3H, s), 5.11 (1H, m); 13C-NMR (CDCl3, 150MHz) 15.2, 16.0, 16.3, 17.7, 19.7, 21.0, 22.0, 22.6, 24.8, 25.5, 25.7, 26.7, 27.5, 31.2, 34.1, 34.6, 36.8, 39.9, 40.3, 40.5, 42.4, 47.4, 49.8, 50.0, 50.3, 55.4, 75.4, 124.7, 131.6, 218.0
最初に、マスティックノルマルヘキサンエキス(MHとする)、メタノールエキス(MMとする)の薬剤耐性菌に対する作用を確認した。
使用した菌体は医療現場を悩ませている以下の4つで検討した。
(1)メチシリン耐性黄色ブドウ球菌(MRSA)
(2)バンコマイシン耐性腸球菌(VRE)
(3)大腸菌(E. coli)
(4)緑膿菌(P. aeruginosa)
調整法
1.マスティック抽出エキスMH,MMをアセトンに溶解し、ペーパーディスク(抗生物質検定用、厚手8mm、ADVANTEC)を用い、それぞれ5mg/disk, 20mg/disk,アセトンのみ(コントロール)を調整し、真空乾燥によりアセトンを除去した。
2.約10×9乗 CFU/mlに調整した各菌体を普通寒天培地、ミューラーヒントン培地に塗布し、各用量の被検ディスクを置き、37℃好気条件2日間、培養し増殖阻止円にて判定を行った。
結果、上記の表1と表2に示すようにマスティックのノルマルヘキサンエキス(MH)20mg/diskによりMRSAに対してのみ抗薬剤耐性菌作用を確認した。しかし、メタノールエキスには抗菌活性は確認できなかった。
1.マスティックノルマルヘキサンエキス(MH)をアセトンに溶解し、5mg/disk, 20mg/diskのペーパーディスクを調整した。
2.MH5mg/disk, 20mg/diskのディスクにスクアレン25mg/diskを添加し、ノルマルヘキサン+スクアレンディスク(MH+S)を調整した。また、スクアレン25mg/disk(S)をコントロールとして調整した。
3.約10×6乗 CFU/mlに調整したマラセチアをミューラーヒントン培地に塗布し、各用量の被検ディスクを置き、37℃好気条件2日間、培養し増殖阻止円にて判定を行った。
結果、上記の表3に示すようにマスティックのノルマルヘキサンエキス(MH)は用量依存的にマラセチアの増殖を阻害した。更に、この抗真菌活性はスクアレン25mg/diskの添加により増強した。
1.実施例1で分画したフラクションについて5mg/diskのペーパーディスクを調整し、これにスクアレン25mg/diskを添加し被検ディスクとした。
2.約10×6乗 CFU/mlに調整したマラセチアをミューラーヒントン培地に塗布し、各用量の被検ディスクを置き、37℃好気条件2日間、培養し増殖阻止円にて判定を行った。
結果、表4に示すようにマスティックノルマルヘキサンエキスのトリテルペン成分である3-oxo-28-norolean-16,18dien(Fr.1),oleanoic aldehyde(Fr.3),tirucallol, β-amyrin(Fr.5), 3-oxo-17-hydroxy-norolean-12-en(Fr.6), 3-oxo-20- hydroxy-dammar-24-en(Fr.8)に強い抗マラセチア活性が確認された。
Claims (7)
- マスティックあるいはマスティックの抽出成分とスクアランとを含む抗真菌剤。
- ヤシ油、ミツロウ、スクワレンの中から選択される1種類または複数種をさらに含み、固体状、ゲル状、クリーム状、軟膏または液状物であることを特徴とする請求項1に記載の抗真菌剤。
- スクアレン、ヒノキチオール、黄伯、黄連、黄岑、ヒバ油、馬油、イソプロパノール、グルコン酸クロルヘキシジン、エタノール、トリクロサン、クロルキシレノール、イソプロピルメチルフェノール、塩化ベンザルコニウム、ヒアルロン酸ナトリュウムの中から選択された1種または複数種をさらに含む請求項1または2に記載の抗真菌剤。
- 抗酸化劣化抑制剤としてスクアレン、コエンザイムQ10,αリポ酸、ビタミンP、ビタミンE、γ−オリザノール、β−カロチン、タンニン、ビタミンC、ヘム鉄の中から選択された1種または複数種をさらに含む請求項1、2、3のいずれかに記載の抗真菌剤。
- 請求項1、2、3、4のいずれかに記載の抗真菌剤をカプセル剤、錠剤にし、また該製品を乳化させ、固める為の固化成形用の乳化剤、可塑剤を配合し、固体剤、クリーム剤、軟膏剤、または液剤としたことを特徴とする抗真菌剤。
- 前記固化成形用の乳化剤がヤシ油、前記可塑剤がミツロウ、スクアレンであることを特徴とする請求項5に記載の抗真菌剤。
- 前記マスティックの抽出成分で下記の化学式(1)〜(5)のいずれかで表される抗真菌活性成分の化合物であることを特徴とする抗真菌剤。
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CN2010800632196A CN102905699A (zh) | 2010-02-25 | 2010-04-30 | 抗真菌剂 |
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EP3468530A4 (en) | 2016-06-10 | 2020-03-11 | Clarity Cosmetics Inc. | NON-COMEDOGENOUS HAIR AND SCALP CARE FORMULATIONS AND METHOD OF USE |
CN110269824A (zh) * | 2019-07-19 | 2019-09-24 | 安徽宝利行香料有限公司 | 乳香提取物在日用品及洗涤用品中的应用 |
CN110754362B (zh) * | 2019-11-28 | 2021-06-25 | 杭州创美生物科技有限公司 | 一种富硒金线莲的培养基及其培育方法 |
CN111000744B (zh) * | 2020-01-07 | 2021-10-15 | 拉芳家化股份有限公司 | 一种含协同增效去屑组合的洗发香波 |
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WO2003092712A1 (en) * | 2002-05-01 | 2003-11-13 | Lavipharm S.A. | Use of mastic and its components for the control of microbial infections |
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KR101435163B1 (ko) | 2014-09-01 |
JP5578880B2 (ja) | 2014-08-27 |
KR20120102801A (ko) | 2012-09-18 |
US20120316144A1 (en) | 2012-12-13 |
CN102905699A (zh) | 2013-01-30 |
WO2011104900A1 (ja) | 2011-09-01 |
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