JPH0420900B2 - - Google Patents
Info
- Publication number
- JPH0420900B2 JPH0420900B2 JP1267283A JP1267283A JPH0420900B2 JP H0420900 B2 JPH0420900 B2 JP H0420900B2 JP 1267283 A JP1267283 A JP 1267283A JP 1267283 A JP1267283 A JP 1267283A JP H0420900 B2 JPH0420900 B2 JP H0420900B2
- Authority
- JP
- Japan
- Prior art keywords
- ethyl acetate
- benzene
- extract
- spectrum
- hydrogen atom
- 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.)
- Expired
Links
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- -1 hydroxybiphenyl compound Chemical class 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 58
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 235000019439 ethyl acetate Nutrition 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000284 extract Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 206010012442 Dermatitis contact Diseases 0.000 description 4
- 208000010247 contact dermatitis Diseases 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 238000002211 ultraviolet spectrum Methods 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 230000003266 anti-allergic effect Effects 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- VVOAZFWZEDHOOU-UHFFFAOYSA-N magnolol Chemical compound OC1=CC=C(CC=C)C=C1C1=CC(CC=C)=CC=C1O VVOAZFWZEDHOOU-UHFFFAOYSA-N 0.000 description 3
- CLWOXNLVWMXBRD-QGZVFWFLSA-O Magnocurarine Chemical compound C([C@H]1[N+](C)(C)CCC=2C=C(C(=CC=21)O)OC)C1=CC=C(O)C=C1 CLWOXNLVWMXBRD-QGZVFWFLSA-O 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 230000002921 anti-spasmodic effect Effects 0.000 description 2
- 210000000624 ear auricle Anatomy 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 241000411851 herbal medicine Species 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- HJRJRUMKQCMYDL-UHFFFAOYSA-N 1-chloro-2,4,6-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 HJRJRUMKQCMYDL-UHFFFAOYSA-N 0.000 description 1
- MBBITBYACKGMSW-UHFFFAOYSA-N 2-(2-hydroxy-5-prop-2-enylphenyl)-4-propylphenol Chemical compound CCCC1=CC=C(O)C(C=2C(=CC=C(CC=C)C=2)O)=C1 MBBITBYACKGMSW-UHFFFAOYSA-N 0.000 description 1
- IBKNHHZQPPUDQJ-UHFFFAOYSA-N 2-(4-hydroxy-3-prop-2-enylphenyl)-4-propylphenol Chemical compound CCCC1=CC=C(O)C(C=2C=C(CC=C)C(O)=CC=2)=C1 IBKNHHZQPPUDQJ-UHFFFAOYSA-N 0.000 description 1
- SDRALVQCLJHHOR-UHFFFAOYSA-N 2-chloro-1,3,5-trinitrobenzene;ethanol Chemical compound CCO.[O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 SDRALVQCLJHHOR-UHFFFAOYSA-N 0.000 description 1
- BYTORXDZJWWIKR-UHFFFAOYSA-N Hinokiol Natural products CC(C)c1cc2CCC3C(C)(CO)C(O)CCC3(C)c2cc1O BYTORXDZJWWIKR-UHFFFAOYSA-N 0.000 description 1
- 241001673966 Magnolia officinalis Species 0.000 description 1
- 241000218377 Magnoliaceae Species 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- FVYXIJYOAGAUQK-UHFFFAOYSA-N honokiol Chemical compound C1=C(CC=C)C(O)=CC=C1C1=CC(CC=C)=CC=C1O FVYXIJYOAGAUQK-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
本発明は、一般式
（式中R1は水素原子または水酸基であり、R2は
水素原子または水酸基であり、R3は水素原子ま
たはメトキシ基である）で示される新規なヒドロ
キシビフエニル化合物に関するものである。
上記式（）で示される新規なヒドロキシビフ
エニル化合物は、唐厚朴を原料とし、これを抽出
することにより分離して得られるものである。唐
厚朴は、モクレン科（Magnoliaceae）のカラホ
ウ（Magnolia officinalis）の樹皮を乾燥したも
ので、古来より鎮痛、鎮痙などを目標にして多く
の漢方処方に配合されている漢方の要薬である
が、唐厚朴の水性エキスには、クラーレ様作用が
認められ、またエーテルエキスには、中枢抑制作
用、鎮痛作用及び鎮痙作用が認められている。ま
た唐厚朴に含まれているマグノロール
（Magnolol）、ホオノキオール（Honokiol）、及
びマグノクラリン（Magnocurarine）に中枢性
の筋弛緩作用をもつことが報告されているが、最
近、唐厚朴抽出物の薬理作用として新しく抗アレ
ルギー作用が見い出されたことが報告された〔日
本薬理学会誌、80、31、（1982）〕。
本発明者等は、抗アレルギー活性成分の究明を
目的として唐厚朴の抽出、分離を行い、新規なヒ
ドロキシビフエニル化合物を取得することに成功
した。本発明はこの新規化合物に関するものであ
る。本発明に係わる新規なヒドロキシビフエニル
化合物は次式（）
（式中R1は水素原子または水酸基であり、R2は
水素原子または水酸基であり、R3は水素原子ま
たはメトキシ基である）で示される化合物であ
る。
この新規なヒドロキシビフエニル化合物は、例
えば唐厚朴を水またはメタノールで室温抽出し、
これを濃縮して得たエキス水と酢酸エチルで分配
処理し、酢酸エチル層を濃縮し、次にこの濃縮物
をシリカゲルを用いたクロマトグラフイーに付
し、ヘキサン、ベンゼン、アセトン、酢酸エチル
の各種混合比の溶媒で溶出し、この酢酸エチル溶
出部（これをEtOAc＃２とする）をシリカゲル、
アルミナ及びセフアデツクスLH−20を用いたカ
ラムクロマトグラフイーに付し、ヘキサン・ベン
ゼン、ヘキサン・アセトン、ベンゼン・アセト
ン、ベンゼン・酢酸エチル等の混合溶剤で展開及
び溶出することにより得られる。
本発明に係わる化合物は、医薬あるいはその中
間体として、特に抗アレルギー作用剤として有用
性を有する物質である。
以下に本発明の化合物に関し、その製造例なら
びに物性を実施例として掲げる。
実施例記載の化合物は、いずれも質量分析、元
素分析、IRスペクトル、UVスペクトル及び
NMR（PMR、CMR）スペクトルによりその構
造が決定された。
実施例 １
唐厚朴４Kgを粉砕し、この粉砕物を９のメタ
ノールまたは水で12〜24時間、室温で２回抽出
し、この抽出液を合併し、濃縮し、600ｇのエキ
スを得る。このエキスを２の水に溶かし、酢酸
エチルで３回分配処理し、酢酸エチル層を濃縮
し、濃縮物（エキス状）300ｇを得る。
この濃縮物をシリカゲル500ｇを用いたカラム
クロマトグラフイーに付し、ベンゼンに対し、酢
酸エチルの混合割合を順次増加させたベンゼン・
酢酸エチル混合溶剤（１：０〜３：１）で展開
し、100mlづつ分取し、ベンゼン溶出部、ベンゼ
ン・酢酸エチル（50：１）溶出部、ベンゼン・酢
酸エチル（20：１）溶出部、ベンゼン・酢酸エチ
ル（３：１）溶出部を各画分とする。
上記ベンゼン溶出部の画分の溶剤を留去し、ア
ルミナ50ｇを用いたカラムクロマトグラフイーに
付し、ヘキサン・ベンゼン（３：１）で溶出する
と次式（）
で表わされる化合物（白色粉末）400mlが得られ
た。この化合物は8.9ジヒドロキシジヒドロホノ
キオール（8.9dihydroxy dihydrohonokiol）と
命名された。
質量分析値 300、1384（理論値 300、1363）
分子式 （C18H20O4）
色、性状 白色粉末
比旋光度 〔α〕20 D−6.8°（Ｃ＝0.91、MeOH）
UVスペクトル （λMeOH naxnm）
293（ε＝17800）、（ε＝19400）
NMR（PMR）スペクトル（δin MeOH）
2.65（dd、Ｊ＝7.5、11.5Hz、1H、７）、2.78
（dd、Ｊ＝６Hz、1H、7′）、3.40（br、ｄ、2H、
7′）、3.40〜3.50（ｍ、2H、９）、3.82（ｍ、1H、
８）、4.87〜5.20（ｍ、2H、9′）、5.83〜6.25（ｍ、
1H、8′）、6.80〜7.37（6H、Ar−Ｈ）
NMR（CMR）スペクトル
The present invention is based on the general formula (In the formula, R 1 is a hydrogen atom or a hydroxyl group, R 2 is a hydrogen atom or a hydroxyl group, and R 3 is a hydrogen atom or a methoxy group.) The novel hydroxybiphenyl compound represented by the above formula () is obtained by extracting and separating Karako Poku from the raw material. Tangkoboku is the dried bark of Magnolia officinalis, a member of the Magnoliaceae family, and has been a key herbal medicine since ancient times, having been included in many Chinese herbal prescriptions for pain relief and antispasmodic effects. Its aqueous extract has been shown to have curare-like effects, and its ether extract has been shown to have central depressant, analgesic, and antispasmodic effects. In addition, it has been reported that Magnolol, Honokiol, and Magnocurarine contained in Tanghoboku have a central muscle relaxing effect. It was reported that a new anti-allergic effect was discovered [Journal of the Japanese Pharmacological Society, 80, 31, (1982)]. The present inventors extracted and separated Tangko Poku for the purpose of investigating the anti-allergic active ingredient, and succeeded in obtaining a novel hydroxybiphenyl compound. The present invention relates to this new compound. The novel hydroxybiphenyl compound according to the present invention has the following formula () (In the formula, R 1 is a hydrogen atom or a hydroxyl group, R 2 is a hydrogen atom or a hydroxyl group, and R 3 is a hydrogen atom or a methoxy group). This novel hydroxybiphenyl compound can be obtained by extracting, for example, Tango Pak with water or methanol at room temperature.
The concentrated extract was partitioned between water and ethyl acetate, the ethyl acetate layer was concentrated, and the concentrate was then subjected to chromatography using silica gel to separate hexane, benzene, acetone, and ethyl acetate. Elute with solvents of various mixing ratios, and transfer this ethyl acetate eluate (this will be referred to as EtOAc#2) to silica gel,
It is obtained by subjecting it to column chromatography using alumina and Sephadex LH-20, developing and eluting it with a mixed solvent such as hexane/benzene, hexane/acetone, benzene/acetone, or benzene/ethyl acetate. The compound according to the present invention is a substance that is useful as a medicine or an intermediate thereof, particularly as an antiallergic agent. Examples of the production and physical properties of the compounds of the present invention are listed below. All the compounds described in the examples were analyzed by mass spectrometry, elemental analysis, IR spectrum, UV spectrum, and
Its structure was determined by NMR (PMR, CMR) spectra. Example 1 4 kg of Tangho Pak was ground, and the ground product was extracted twice with methanol or water (9) at room temperature for 12 to 24 hours, and the extracts were combined and concentrated to obtain 600 g of extract. This extract was dissolved in water from step 2, partitioned three times with ethyl acetate, and the ethyl acetate layer was concentrated to obtain 300 g of a concentrate (extract form). This concentrate was subjected to column chromatography using 500 g of silica gel, and the mixture of benzene and ethyl acetate was successively increased.
Develop with a mixed solvent of ethyl acetate (1:0 to 3:1), collect 100 ml each, and extract the benzene eluate, the benzene/ethyl acetate (50:1) eluate, and the benzene/ethyl acetate (20:1) eluate. , the benzene/ethyl acetate (3:1) eluate was used as each fraction. The solvent in the benzene elution fraction was distilled off, and the fraction was subjected to column chromatography using 50 g of alumina, and eluted with hexane/benzene (3:1). 400 ml of the compound (white powder) represented by was obtained. This compound was named 8.9dihydroxy dihydrohonokiol. Mass spectrometry value 300, 1384 (theoretical value 300, 1363) Molecular formula (C 18 H 20 O 4 ) Color, properties White powder specific rotation [α] 20 D −6.8° (C=0.91, MeOH) UV spectrum (λ MeOH nax nm) 293 (ε=17800), (ε=19400) NMR (PMR) spectrum (δin MeOH) 2.65 (dd, J=7.5, 11.5Hz, 1H, 7), 2.78
(dd, J=6Hz, 1H, 7'), 3.40 (br, d, 2H,
7'), 3.40-3.50 (m, 2H, 9), 3.82 (m, 1H,
8), 4.87-5.20 (m, 2H, 9'), 5.83-6.25 (m,
1H, 8'), 6.80-7.37 (6H, Ar-H) NMR (CMR) spectrum
【表】
実施例 ２
実施例１において得られたベンゼン・酢酸エチ
ル（50：１）溶出部画分の溶剤を留去し、アルミ
ナ50ｇを用いたカラムクロマトグラフイーに付
し、メタノールで溶出し、さらにシリカゲル100
ｇを用いたカラムクロマトグラフイーに付し、ヘ
キサン・アセトン（10：１）で溶出すると、次式
（）
で表わされる化合物（白色粉末）200mgが得られ
た。この化合物は8.9−ジヒドロキシ−７−メト
キシジヒドロホモキオール（8.9−dihydroxy−７
−metoxy dihydrohomokiol）と命名された。
質量分析値 330、1499（理論値330、1467）
分子式 （C19H22O5）
色、性状 白色粉末
比旋光度 〔α〕＋3.0°（Ｃ＝0.88、MeOH）
UVスペクトル（λMeOH naxnm）
293（ε＝11500）、259（ε＝14500）
NMR（PMR）スペクトル（δin MeOH）
3.42（br、ｄ、2H、7′）、3.30〜3.45（br.m、2H、
9′）、3.70（Ｍ、1H、８）、4.17（ｄ、Ｊ＝７Hz、
1H、７）、4.80〜5.20（ｍ、2H、9′）、5.83〜
6.25（ｍ、1H、8′）、6.82〜7.40（ｍ、6H、Ar−
Ｈ）
NMR（CMR）スペクトル[Table] Example 2 The solvent of the benzene/ethyl acetate (50:1) elution fraction obtained in Example 1 was distilled off, and the fraction was subjected to column chromatography using 50 g of alumina, and eluted with methanol. , plus silica gel 100
When subjected to column chromatography using g and eluted with hexane/acetone (10:1), the following formula () 200 mg of the compound represented by (white powder) was obtained. This compound is 8.9-dihydroxy-7-methoxydihydrohomokiol (8.9-dihydroxy-7-methoxydihydrohomokiol).
-methoxy dihydrohomokiol). Mass spectrometry value 330, 1499 (theoretical value 330, 1467) Molecular formula (C 19 H 22 O 5 ) Color, properties White powder Specific rotation [α] + 3.0° (C = 0.88, MeOH) UV spectrum (λ MeOH nax nm) 293 (ε=11500), 259 (ε=14500) NMR (PMR) spectrum (δin MeOH) 3.42 (br, d, 2H, 7'), 3.30-3.45 (br.m, 2H,
9′), 3.70 (M, 1H, 8), 4.17 (d, J=7Hz,
1H, 7), 4.80~5.20 (m, 2H, 9′), 5.83~
6.25 (m, 1H, 8′), 6.82~7.40 (m, 6H, Ar−
H) NMR (CMR) spectrum
【表】
実施例 ３
実施例１において得られたベンゼン・酢酸エチ
ル（20：１）溶出部画分の溶剤を留去し、セフア
デツクスLH−20、50ｇを用いたカラムクロマト
グラフイーに付し、ベンゼン・アセトン（20：
１）で溶出し、さらにシリカゲル100ｇを用いた
カラムクロマトグラフイーに付し、クロロホル
ム・アセトン（50：１）で溶出する。
このクロロホルム・アセトン（50：１）溶出部
のうち薄層クロマトグラフイーにより単一成分で
あるとわかつた溶出部から溶剤を留去し、残留物
をベンゼンで再結晶することにより、融点135〜
136°の次式（）
で表わされる化合物（白色粉末）200mgが得られ
た。この化合物は8.9−ジヒドロキシジヒドロマ
グノロール（8.9−dihydroxy dihydromagnolol）
と命名された。
質量分析値 300、1339（理論値300、1361）
分子式 （C18H20O4）
色、性状 白色粉末
比旋光度 〔α〕−0.8°（Ｃ＝1.5 MeOH）
UVスペクトル （λMeOH naxnm）
293（ε＝18600）、256（ε＝18000）
NMR（PMR）スペクトル（δ in MeOH）
2.52〜2.93（ｍ、2H、７）、3.35（br.d、2H、
7′）、3.39〜3.63（ｍ、2H、９）、3.60〜4.10（ｍ、
1H、8′）、4.90〜5.20（ｍ、2H、9′）、5.80〜6.20
（ｍ、1H、8′）、6.80〜7.35（ｍ、6H、Ar−Ｈ）
NMR（CMR）スペクトル[Table] Example 3 The solvent of the benzene/ethyl acetate (20:1) eluted fraction obtained in Example 1 was distilled off and subjected to column chromatography using 50 g of Sephadex LH-20. Benzene acetone (20:
1), and then subjected to column chromatography using 100 g of silica gel, and eluted with chloroform/acetone (50:1). The solvent was distilled off from the chloroform/acetone (50:1) eluate, which was found to be a single component by thin layer chromatography, and the residue was recrystallized with benzene, resulting in a solution with a melting point of 135~
The following equation for 136° () 200 mg of the compound represented by (white powder) was obtained. This compound is 8.9-dihydroxy dihydromagnolol.
It was named. Mass spectrometry value 300, 1339 (theoretical value 300, 1361) Molecular formula (C 18 H 20 O 4 ) Color, properties White powder specific rotation [α] -0.8° (C = 1.5 MeOH) UV spectrum (λ MeOH nax nm) 293 (ε=18600), 256 (ε=18000) NMR (PMR) spectrum (δ in MeOH) 2.52-2.93 (m, 2H, 7), 3.35 (br.d, 2H,
7'), 3.39-3.63 (m, 2H, 9), 3.60-4.10 (m,
1H, 8′), 4.90-5.20 (m, 2H, 9′), 5.80-6.20
(m, 1H, 8'), 6.80-7.35 (m, 6H, Ar-H) NMR (CMR) spectrum
【表】
本発明による新規なヒドロキシビフエニル化合
物は、いずれも酢酸エチル層エキスより得られた
もので、この酢酸エチル層エキスについては、抗
アレルギー活性が、下記の実験法によつて測定さ
れた。その結果は表に示す如くである。
実験法
Asherson and ptakの方法に従つて行つた。
すなわち、８〜９週令のddY系雄性マウスを１群
10匹として、マウスの腹部に７％ピクリルクロラ
イドのエタノール溶液の0.1mlを塗布して感作し
た。７日後に両耳朶に１％ピクリルクロライドの
オリーブ油溶液の0.02mlを塗布して誘発し、24時
間後の耳朶の厚さをdial thickness gauge（尾崎
製作所）を用いて測定し、誘発前の耳朶の厚さを
差し引き、接触性皮膚炎による腫張度とした。
前述の被検生薬エキス、すなわち水抽出エキ
ス、酢酸エチル層エキス及びEtOAc＃２エキス
を接触性皮膚炎誘発16時間後にそれぞれ50mg／Kg
を経口投与する。[Table] The novel hydroxybiphenyl compounds of the present invention were all obtained from ethyl acetate layer extract, and the antiallergic activity of this ethyl acetate layer extract was measured by the following experimental method. . The results are shown in the table. Experimental method The method of Asherson and Ptak was followed.
That is, one group of ddY male mice aged 8 to 9 weeks was
Ten mice were sensitized by applying 0.1 ml of a 7% picryl chloride ethanol solution to their abdomens. Seven days later, induction was induced by applying 0.02 ml of 1% picryl chloride in olive oil to both earlobes, and the thickness of the earlobes was measured 24 hours later using a dial thickness gauge (Ozaki Seisakusho). The thickness was subtracted to determine the degree of swelling due to contact dermatitis. 50 mg/Kg of each of the above-mentioned herbal medicine extracts tested, namely water extract, ethyl acetate layer extract, and EtOAc#2 extract, 16 hours after induction of contact dermatitis.
Administer orally.
【表】
表に示す結果から酢酸エチル層エキスの接触性
皮膚炎に対する抑制率は、水抽出エキスよりも大
きいことがわかり、上記の新規ヒドロキシビフエ
ニル化合物が、接触性皮膚炎に対する抑制作用を
有する可能性があることが判明した。[Table] From the results shown in the table, it was found that the ethyl acetate layer extract has a greater inhibition rate against contact dermatitis than the water extract, and the above-mentioned new hydroxybiphenyl compound has an inhibitory effect on contact dermatitis. It turns out it's possible.
Claims (1)
水素原子または水酸基であり、R3は水素原子ま
たはメトキシ基である）で示される新規ヒドロキ
シビフエニル化合物。[Claims] 1. General formula A novel hydroxybiphenyl compound represented by the formula (wherein R 1 is a hydrogen atom or a hydroxyl group, R 2 is a hydrogen atom or a hydroxyl group, and R 3 is a hydrogen atom or a methoxy group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1267283A JPS59139335A (en) | 1983-01-31 | 1983-01-31 | Novel hydroxybiphenyl compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1267283A JPS59139335A (en) | 1983-01-31 | 1983-01-31 | Novel hydroxybiphenyl compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59139335A JPS59139335A (en) | 1984-08-10 |
| JPH0420900B2 true JPH0420900B2 (en) | 1992-04-07 |
Family
ID=11811859
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1267283A Granted JPS59139335A (en) | 1983-01-31 | 1983-01-31 | Novel hydroxybiphenyl compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59139335A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015115432A1 (en) | 2014-01-29 | 2015-08-06 | オムロン株式会社 | Quality management device and method for controlling quality management device |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0382213T3 (en) * | 1989-02-08 | 1995-07-10 | Otsuka Pharma Co Ltd | Biphenyl derivative, agent for repairing or protecting against nerve cell degeneration and method of preparing a phenyl derivative included in this agent |
| WO2000040532A2 (en) * | 1998-12-31 | 2000-07-13 | Board Of Regents, The University Of Texas System | Synthesis of dihydrohonokiol compositions |
| US7608741B2 (en) * | 2005-05-30 | 2009-10-27 | Korea Institute Of Oriental Medicine | Mass separation method of magnolol from Magnoliae cortex radix |
-
1983
- 1983-01-31 JP JP1267283A patent/JPS59139335A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015115432A1 (en) | 2014-01-29 | 2015-08-06 | オムロン株式会社 | Quality management device and method for controlling quality management device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59139335A (en) | 1984-08-10 |
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