JPH11130685A - Antiallergic agent - Google Patents

Antiallergic agent

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Publication number
JPH11130685A
JPH11130685A JP9314247A JP31424797A JPH11130685A JP H11130685 A JPH11130685 A JP H11130685A JP 9314247 A JP9314247 A JP 9314247A JP 31424797 A JP31424797 A JP 31424797A JP H11130685 A JPH11130685 A JP H11130685A
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Japan
Prior art keywords
betel
extract
leaves
eugenol
antiallergic agent
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JP9314247A
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Japanese (ja)
Inventor
Joji Yamahara
條二 山原
Original Assignee
Ranka Aayurubeedeikku Herb Yakuhin Kk
Res Inst For Prod Dev
ランカアーユルベーディックハーブ薬品株式会社
財団法人生産開発科学研究所
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Application filed by Ranka Aayurubeedeikku Herb Yakuhin Kk, Res Inst For Prod Dev, ランカアーユルベーディックハーブ薬品株式会社, 財団法人生産開発科学研究所 filed Critical Ranka Aayurubeedeikku Herb Yakuhin Kk
Priority to JP9314247A priority Critical patent/JPH11130685A/en
Publication of JPH11130685A publication Critical patent/JPH11130685A/en
Application status is Withdrawn legal-status Critical

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Abstract

PROBLEM TO BE SOLVED: To obtain an antiallergic agent which is high in the safety and originates from a natural product.
SOLUTION: This antiallergic agent is obtained by formulating an extract extracted with water or an organic solvent from leaves of Piper betle L. and demethyleugenol of the formula isolated and purified from the extract as active ingredients.
COPYRIGHT: (C)1999,JPO

Description

【発明の詳細な説明】 DETAILED DESCRIPTION OF THE INVENTION

【0001】 [0001]

【発明の属する技術分野】本発明は、アレルギー反応、 BACKGROUND OF THE INVENTION The present invention is, allergic reactions,
特にI型アレルギーに分類される、いわゆるアトピー型アレルギーに有効な天然物由来の抗アレルギー剤に関する。 In particular it is classified as type I allergy, relates to an anti-allergic agent from effective natural products called atopic allergy.

【0002】 [0002]

【従来の技術】抗アレルギー剤は、アレルギー反応を予防し、抑制し、且つつこれを軽減する目的の薬剤である。 BACKGROUND ART antiallergic agents, to prevent allergic reactions, suppression, and is an agent for the purpose of and one alleviate this. つまり、抗アレルギー剤は、細胞の安定因子として、及び/又はヒスタミンやロイコトリエン等の肥満細胞が抗原物質の存在に反応して起こる脱顆粒を防止する肥満細胞の抑制因子として作用すると考えられている。 In other words, anti-allergic agents are believed as a stable factor for cells, and / or mast cells, such as histamine and leukotriene act as inhibitors of mast cells to prevent degranulation occurring in response to the presence of the antigenic substance .
抗原物質が侵入すると、肥満細胞の表面で免疫グロブリンIgEと結合して脱顆粒が起こり、肥満細胞成分が細胞外環境に排出され、各種の機序を経て、かゆみ、じんましん、花粉症、気管支喘息等各種のアレルギー反応による症状を誘発する。 When the antigenic substance enters binds to immunoglobulin IgE on the surface of mast cells occur degranulation, mast cells components are discharged into the extracellular environment, through various mechanisms, itching, hives, hay fever, bronchial asthma induces symptoms of equal variety of allergic reactions.

【0003】抗アレルギー剤は、副腎皮質ホルモンの他、合成医薬品が種々開発され、用いられている。 [0003] Anti-allergic agents, other adrenocortical hormones, synthetic drugs been developed and are used. しかしながら、それらの副作用は常に問題とされる場合が多い。 However, these side effects are often always be a problem. また、各種アレルギー性疾患の中でも近年顕著に発症が増加している、I型アレルギーいわゆるアトピーの症状を治療する薬物の開発が強く望まれている。 Also, onset in recent years significantly among various allergic diseases has increased, the development of drugs to treat symptoms of type I allergy-called atopy has been strongly desired.

【0004】 [0004]

【発明が解決しようとする課題】日常手軽に茶剤の様な形で服用することにより、これらのアレルギー反応の発症を制御する天然物があれば、その益は多大である。 By taking in such form of everyday easily tea agent [0006], if there is a natural product to control the onset of these allergic reactions, the benefit is great. 本発明者は、上記問題点を鑑み、食品や香辛料として用いられている天然の植物を、国内のみならず、広く中国や東南アジアにも求め、I型アレルギーのモデルを用い、 The present inventors, in view of the above problems, a natural plant which is used as a food and spices, not only in Japan but widely sought in China and Southeast Asia, using a model of the type I allergy,
検討した。 investigated.

【0005】本発明者は検討を重ねていく中で、キンマ(英文名:Piper betel)に着目した。 [0005] The present inventors have in going extensive investigations, betel (English name: Piper betel) focused on. キンマは、東南アジア等では一般に生薬として市販されているが、キンマ自体及びその抽出物が抗アレルギー作用を示すことは、全く知られていない。 Betel, are commercially available generally as herbal medicine in Southeast Asia, betel itself and its extract is to exhibit anti-allergic effect, it is completely unknown.

【0006】キンマはコショウ科に属する常緑蔦性の灌木で、東南アジアやインド、スリランカ等に広く分布している。 [0006] betel in the evergreen ivy of the shrub belonging to the pepper family, Southeast Asia and India, is widely distributed in Sri Lanka and the like. キンマの葉・根・種子は健胃、去痰薬として用いられているほか、特に台湾から東南アジア、インド、 Leaves, roots, seeds of betel stomach, in addition to being used as an expectorant, especially Southeast Asia from Taiwan, India,
スリランカ、パキスタン等では、いわゆるbetel Sri Lanka, Pakistan, etc., the so-called betel
chewing(ベトル チューイング)として、ガムのように噛んで嗜好品として用いており、アーユルベーダ インド学 (インド、スリランカの伝承医学)においては、神聖で重要な生薬として知られている。 As chewing (Betoru chewing), chewing as gum is used as luxury goods, in the Ayurvedic Indian Studies (India, tradition medicine of Sri Lanka), is known as sacred and important herbal medicine.

【0007】本発明者は、上記課題に鑑み、安全性が高い天然由来の生薬を用いて、新規な抗アレルギー剤を提供すべく、系統的な実験研究を続けた結果、本発明を完成した。 The present inventors have, in view of the above problems, using herbal derived high safety natural, to provide a novel anti-allergic agent, as a result of continued systematic experimental study and completed the present invention .

【0008】つまり、キンマの葉に非常に高含有量(重量比:1〜3%)で含まれるデメチルオイゲノールにアレルギー反応を抑制する作用があること、特にアトピー型アレルギー反応であるI型に強い抑制作用を示すことを見出し、本発明を完成するに至った。 [0008] That is, a very high content in betel leaves (weight ratio: 1-3%) to a de-methyl eugenol contained by some action of suppressing allergic reactions, I type is particularly atopic allergic reactions It found to exhibit a strong inhibitory effect, and have completed the present invention. キンマの葉にデメチルオイゲノールが含有されていること及びデメチルオイゲノールに抗アレルギー作用があることは、全く知られてない。 The de methyleugenol the betel leaf is anti-allergic effect in and demethyl eugenol is contained is not known at all.

【0009】 [0009]

【発明の構成】本発明は、キンマの葉から水や有機溶媒を用いて抽出したエキスを有効成分としてなる抗アレルギー剤、及びキンマの葉から水や有機溶媒を用いて抽出して得られたエキスを、単離、精製した化学構造式[2]で示されるデメチルオイゲノールを有効成分としてなる抗アレルギー剤に関する。 The present invention SUMMARY OF THE INVENTION] The antiallergic agent comprising as an active ingredient the extracted extract using water or an organic solvent from betel leaves, and were obtained from betel leaf extract using water or an organic solvent the extract relates to an isolated, antiallergic agent comprising the demethyl eugenol represented by purified chemical structural formula [2] as an active ingredient. デメチルオイゲノールの化学構造式は次に示す。 Chemical structural formula of demethyl eugenol below.

【0010】 [0010]

【化2】 ## STR2 ##

【0011】 [0011]

【発明を解決するための手段】本発明では、要するに、 In THE INVENTION solutions for the present invention, in short,
キンマの葉の粉末を水や有機溶媒で抽出したエキス、若しくは該エキスから単離、精製したデメチルオイゲノールを用いて、アレルギーのモデルを評価することにより、本発明の有効性を認めることができた。 Extract powder betel leaves were extracted with water or an organic solvent, or isolated from the extract using demethyl eugenol purified by evaluating the model of allergic, it can be observed the efficacy of the present invention It was. 有機溶媒としては、アルコール、アセトン等を用いる。 As the organic solvent, using an alcohol, acetone or the like.

【0012】 [0012]

【発明の実施態様】本発明でのキンマは、古来から食用とされている葉の部分を用いる。 Betel in the present invention embodiment of the Invention, using part of the leaf is from the ancient times and edible. 後述する実験動物のデータから推定して、ヒトの1回あたりの服用量は、キンマの葉エキスでは1000〜2000mg、デメチルオイゲノールでは15〜30mgで、充分な抗アレルギ− Estimated from the data of the later-described experimental animals, the dose per single human in leaf extract betel 1000~2000Mg, in 15~30mg in-demethyl eugenol, sufficient antiallergic -
効果を示す。 Shows the effect. 用いる剤形は適当な賦形剤を添加して、顆粒や錠剤として用いているが、キンマの葉の粉末をそのまま茶剤の形式で用いても、その効果に変化はない。 Using dosage forms with the addition of suitable excipients, is used as granules or tablets, be used in the form of intact tea agent powder betel leaves, the effect will remain.

【0013】以下、実施例等を上げて本発明を説明するが、本発明は以下の実施例によって限定されるものではない。 [0013] The following will explain the invention with examples, but the present invention is not limited by the following examples.

【0014】 エキスの抽出方法キンマの葉を粉砕機にて100〜200メッシュとしたもの100gに1リットルの溶媒を加え、約3時間加温した後に、濾過してその濾液を45℃で減圧濃縮して完全に溶媒を留去し、使用する溶媒を水及びアルコールやアセトンとすることにより、それぞれ水エキス、アルコールエキス、アセトンエキスを得た。 [0014] 1 liter of solvent 100g those with 100-200 mesh leaves extraction method betel extract by a pulverizer addition, after was allowed about 3 hours pressurized, filtered and concentrated under reduced pressure to the filtrate at 45 ° C. It was distilled off completely solvent was obtained by the solvent used and water and alcohol or acetone, respectively water extract, an alcohol extract, acetone extract. 水抽出エキスの収率は約22〜23%で、他の有機溶媒抽出エキスの収率は約15〜23%であった。 The yield of the water extract is about 22 to 23%, the yield of other organic solvents extract was about 15-23%.

【0015】 デメチルオイゲノールの単離、精製粗切して乾燥させたキンマの葉2kgを35%アルコール10リットルに入れ、約3時間加温抽出後濾過し、その濾液を減圧下45℃で完全に溶媒を留去して、35% [0015] Isolation of demethyl eugenol, put leaves 2kg betel drying purified crude switching to 35% alcohol 10 liters filtered after about 3 hours warming extraction, complete the filtrate under reduced pressure at 45 ° C. the solvent was removed by evaporation, 35%
アルコールエキスを得た。 To give the alcohol extract. このエキス収率は、23.2 The extract yield, 23.2
%であった。 %Met. 該エキスをシリカゲルカラムにかけ、n− Multiplying the extract to a silica gel column, n-
ヘキサン:酢酸エチル=3:1の展開溶媒で流出させ、 Hexane: ethyl acetate = 3: allowed to flow in one of the developing solvent,
デメチルオイゲノールを約24.1g得た(収率は5. The demethyl eugenol obtain about 24.1 g (yield 5.
2%)。 2%). つまり、図1に示すように、キンマ乾燥葉中にデメチルオイゲノールは1.2%もの高含有量であった。 That is, as shown in FIG. 1, demethyl eugenol in betel dried leaves was high content of 1.2% ones. デメチルオイゲノールは文献上で既に知られている化合物であり、NMR等の各種物理恒数から当該化合物であることを確定した。 Demethyl eugenol is a compound already known in the literature, it was to confirm that the various physical constants of NMR etc. are the compounds.

【0016】実施例1 ラット受身皮膚アナフィラキシー(PCA)反応ジニトロフェニル化ウシ血清アルブミン(以下、DNP [0016] Example 1 Rat passive cutaneous anaphylaxis (PCA) reaction dinitrophenylated bovine serum albumin (hereinafter, DNP
−BSAと略す)は、Tada and Okumuraの方法(文献名:J. Immunol,106, pp.1002-1011[1971])に準じて作製した。 Abbreviated-BSA), the method of Tada and Okumura (literature name:. J Immunol, 106, was prepared in accordance with pp.1002-1011 [1971]). また抗DNPは、生化学工業製を用いた。 The anti-DNP was used manufactured by Seikagaku. 比較対照薬としてトラニラスト(キッセイ薬品製)を使用した。 It was used tranilast (Kissei made chemicals) as compared to control drug. 実験方法は、Wistar系雄性ラット(体重20 The experimental method, Wistar male rats (body weight 20
0〜220g)の背部を刈毛し、その皮内にリン酸緩衝生理食塩液(pH7.4)で6250倍に希釈した抗D Was shaved dorsal of 0~220g), anti-D diluted 6250-fold with phosphate buffered saline (pH 7.4) in the skin
NPを0.1ml注射し、感作した。 The NP was 0.1ml injection, were sensitized. 46時間後に各被検薬物を1%のアラビアゴムと共に懸濁して経口投与し、その2時間経過後に、0.75mgのDNP−BS Orally administered in suspension of each test drug with 1% gum arabic after 46 hours, after the lapse of 2 hours, the 0.75 mg DNP-BS
Aを1%エバンスブルーに溶解したものを、尾静脈から0.5ml投与し、PCA反応を惹起させた。 A solution obtained by dissolving A 1% Evans blue was 0.5ml administered from the tail vein, was induced PCA reaction. 30分後に頸動脈より放血致死させ、背部に漏出した色素の面積をデジタルプラニメーター(内田洋行製)を用いて測定し、対照群の色素漏出面積を100%とした場合の相対値で示して効果を判定した。 Were killed by exsanguination from the carotid artery after 30 minutes, the area of ​​the leaked dye back was measured using a digital planimeter (manufactured by Uchida Yoko), the dye leakage area of ​​the control group shows a relative value is 100% effective It was determined. その結果を表1に示す。 The results are shown in Table 1. キンマの葉の特に35%アルコール抽出エキスにより強い抗アレルギー作用があり、またデメチルオイゲノールはトラニラスト以上の効果を示した。 There is a strong anti-allergic effect in particular 35% alcohol extract of betel leaves, also demethyl eugenol showed the effect of more than Tranilast.

【0017】 [0017]

【表1】 [Table 1]

【0018】実施例2 ラット感作腹腔滲出細胞からの抗原刺激によるヒスタミ [0018] Hisutami by antigen stimulation from Example 2 rats sensitized peritoneal exudate cells
ン遊離比較対照薬としては、トラニラスト(キッセイ薬品製)、アンレキサノクス(武田薬品工業製)を使用した。 The emission free comparative drug, tranilast (Kissei Ltd. Pharmaceutical) was used amlexanox (manufactured by Takeda Chemical Industries, Ltd.). 実験方法は、Wistar系雄性ラット(体重30 The experimental method, Wistar male rats (body weight 30
0〜400g)の腹腔内に肥満細胞用緩衝液(pH7. Mast cell buffer intraperitoneally 0~400g) (pH7.
4,以下MCMと略す)を10mlを注入し、2分間穏やかにマッサージを行った。 4, hereinafter referred to as MCM) was injected 10 ml, it was carried out for 2 minutes gently massaged. 開腹後、滲出している該液をピペットで集め、さらにMCM10mlで腹腔内を洗浄して、滲出液を回収した。 After laparotomy, collect the liquid which exuded a pipette, and washed intraperitoneally further MCM10ml, was collected exudate. これを遠心分離(100× This centrifugation (100 ×
g4℃、10分)後、細胞を3mlのMCMに浮遊させ、MCMで100倍に希釈した抗DNP1mlとともに、37℃で1時間インキュベートを行い、受動感作した。 g4 ° C., 10 minutes) after, cells were suspended in MCM of 3 ml, with anti DNP1ml diluted 100-fold with MCM, for 1 hour at 37 ° C., were passively sensitized. インキュベート終了後、MCMで細胞を3回洗浄した後に、トルイジンブルー染色下、血球計算板で肥満細胞数を算定し、最終的に10 4個/mlとなるように細胞浮遊液を調整した。 After completion of incubation, after washing the cells three times with MCM, under toluidine blue staining, and calculated the number of mast cells in a hemocytometer and adjusted the cell suspension finally so as to be 10 4 / ml. 細胞浮遊液1.62mlを37℃ The cell suspension was 1.62ml 37 ℃
で10分間インキュベートした後、各被検薬物溶液18 After incubation in 10 minutes, each test drug solutions 18
0μlを添加し、15分間反応させた。 Was added .mu.l, it was allowed to react for 15 minutes. 次に200μl Then 200μl
のホスファチジルセリン(1mg/ml)と220μl Phosphatidylserine (1 mg / ml) and 220μl
のDNP−BSA(1mg/ml)を同時に添加し、さらに20分間インキュベートを続けた。 Was added of DNP-BSA to (1 mg / ml) at the same time, incubation was continued for further 20 minutes. 試験管を氷冷して反応を止め、遠心分離(100×g4℃、10分) Stop the reaction tube cooled with ice, centrifuged (100 × g4 ℃, 10 min)
後、上清を分離して遊離したヒスタミンを蛍光法により定量した。 After the histamine liberated by separating the supernatant was determined by fluorescence. その結果を表2に示す。 The results are shown in Table 2. キンマ葉抽出エキス及びその活性成分デメチルオイゲノールは、肥満細胞から炎症や痛みを引き起こすヒスタミンの放出を抑制することが明らかとなった。 Betel leaf extract and its active ingredient-demethyl eugenol, revealed that inhibit the release of histamine that cause inflammation and pain from mast cells.

【0021】 [0021]

【表2】 [Table 2]

【0022】 [0022]

【発明の効果】本発明の抗アレルギー剤は、花粉症をはじめ種々のアトピー症状に有効な天然物で、特に古来から食用とされ高い安全性の確認できる生薬を追究していく考えを基に、多数の食用植物を実験動物モデルを用いて検体した結果、主に東南アジア等で用いられているキンマの葉に、市販の医療医薬品と同等以上の優れた抗アレルギー作用を示し、特にアトピー症状のI型アレルギーに有効であり、且つ安全で安価に供給できる素材である点も優れている。 Antiallergic agent of the present invention exhibits, in an effective natural product for a variety of atopic symptoms including pollinosis, based on intends to particularly pursue the crude drug can confirm the high safety is edible from ancient as a result of the specimen using experimental animal models many edible plants, betel leaves which are mainly used in Southeast Asia, it exhibited excellent anti-allergic effect equal to or larger than that of the commercially available medical pharmaceuticals, especially of atopic symptoms it is effective in type I allergy, and excellent points which is a material that can and safely and inexpensively supplied. よって本発明の産業利用性は、非常に高いといえる。 Therefore, industrial use of the present invention, it can be said that the very high.

【図面の簡単な説明】 BRIEF DESCRIPTION OF THE DRAWINGS

【図1】キンマの葉からデメチルオイゲノールを単離、 [Figure 1] isolating the de-methyl eugenol from the leaves of the betel,
精製する工程等を表したフローシートである。 Is a flow sheet showing the purification to step.

Claims (2)

    【特許請求の範囲】 [The claims]
  1. 【請求項1】 キンマの葉から水や有機溶媒を用いて抽出したエキスを有効成分としてなる抗アレルギー剤。 1. A antiallergic agent comprising as an active ingredient the extracted extract using water or an organic solvent from betel leaves.
  2. 【請求項2】 キンマの葉から水や有機溶媒を用いて抽出して得られたエキスを、単離、精製した化学構造式[1]で示されるデメチルオイゲノールを有効成分としてなる抗アレルギー剤。 Wherein the extract obtained by extraction with leaves from water and an organic solvent betel, isolation, comprising the demethyl eugenol represented by purified chemical structural formula [1] as an active ingredient an anti-allergic agent . 【化1】 [Formula 1]
JP9314247A 1997-10-29 1997-10-29 Antiallergic agent Withdrawn JPH11130685A (en)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002045730A1 (en) * 2000-12-04 2002-06-13 Council Of Scientific And Industrial Research Antimonocytic activity of extracts of piper betel leaves
WO2002045731A1 (en) * 2000-12-04 2002-06-13 Council Of Scientific And Industrial Research Activity of extract of piper betle leaves against leishmania
WO2002049655A1 (en) * 2000-12-18 2002-06-27 Council Of Scientific And Industrial Research Extracts of piper betle leaves as immunomodulator
US6531166B2 (en) * 2000-12-26 2003-03-11 Council Of Scientific And Industrial Research Use of betel leaf extract to induce IFN-gamma production from human peripheral blood T cells and as a Th1 type immunomodulator
US6852344B2 (en) 2000-12-04 2005-02-08 Council Of Scientific And Industrial Research Herbal composition for treating CD33+ acute and chronic myeloid leukemia and a method thereof
US6967034B2 (en) 2002-05-31 2005-11-22 Council Of Scientific And Industrial Research Herbal-based composition for treating acute and chronic myeloid leukemia
US7615574B2 (en) 2002-07-08 2009-11-10 Council Of Scientific And Industrial Research Synergistic composition for treating leukemia
US9301987B2 (en) 2007-09-24 2016-04-05 Laila Nutraceuticals Anti-adipogenic compositions containing Piper betle and Dolichos biflorus

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US6852344B2 (en) 2000-12-04 2005-02-08 Council Of Scientific And Industrial Research Herbal composition for treating CD33+ acute and chronic myeloid leukemia and a method thereof
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US7045157B2 (en) 2000-12-26 2006-05-16 Council Of Scientific & Industrial Research Use of betel leaf extract to induce IFN-gamma production from human peripheral blood T cells and as a Th1 type immunomodulator
US6531166B2 (en) * 2000-12-26 2003-03-11 Council Of Scientific And Industrial Research Use of betel leaf extract to induce IFN-gamma production from human peripheral blood T cells and as a Th1 type immunomodulator
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US9301987B2 (en) 2007-09-24 2016-04-05 Laila Nutraceuticals Anti-adipogenic compositions containing Piper betle and Dolichos biflorus

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