US20090004309A1 - Anti-Gastritis and Anti-Ulcer Agent Containing Momordicae Semen Extract and Momordica Saponin I Isolated From the Same - Google Patents

Anti-Gastritis and Anti-Ulcer Agent Containing Momordicae Semen Extract and Momordica Saponin I Isolated From the Same Download PDF

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Publication number
US20090004309A1
US20090004309A1 US12/096,881 US9688106A US2009004309A1 US 20090004309 A1 US20090004309 A1 US 20090004309A1 US 9688106 A US9688106 A US 9688106A US 2009004309 A1 US2009004309 A1 US 2009004309A1
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Prior art keywords
momordicae semen
gastritis
extract
damage
semen extract
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Abandoned
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US12/096,881
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English (en)
Inventor
Bong Cheol Kim
Joo Hyon Kim
Se Jun Yun
Eun Jung Noh
Gi Uk Jang
Chang-kyun Han
Yong-Baik Cho
Wie-jong Kwak
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SK Chemicals Co Ltd
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SK Chemicals Co Ltd
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Priority claimed from KR1020050126302A external-priority patent/KR20070065652A/ko
Priority claimed from KR1020060128138A external-priority patent/KR101132730B1/ko
Application filed by SK Chemicals Co Ltd filed Critical SK Chemicals Co Ltd
Assigned to SK CHEMICALS CO., LTD. reassignment SK CHEMICALS CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHO, YONG-BAIK, HAN, CHANG-KYUN, JANG, GI UK, KIM, BONG CHEOL, KIM, JOO HYON, KWAK, WIE-JONG, NOH, EUN JUNG, YUN, SE JUN
Publication of US20090004309A1 publication Critical patent/US20090004309A1/en
Abandoned legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants

Definitions

  • the present invention relates to a Momordicae semen extract effective in the prevention and treatment of gastritis or gastric ulcer and momordica saponin I isolated therefrom.
  • the gastric mucosal layer which protects the stomach can be easily damaged by various factors. Typical factors of such include gastric acid, alcohols, non-steroidal anti-inflammatory drugs (NSAID) such as aspirin, bacteria such as Helicobacter pylori [Suzuki. M. and S. Miura, Nippon Rinsho, 15(12), 3154-3158, 1993], disturbance of microcirculation of gastric mucosa and hypotension caused by stress [Tadaoki Mizuno, Yokohama Med. Bull., 38(3,4) , 87-97, 1987], etc.
  • NSAID non-steroidal anti-inflammatory drugs
  • the mucosal protectant which promotes the regeneration of the mucosal tissue to ensure protection against the re-attack of gastritis inducing factors to reduce the recurrence of gastritis, is an important component of the gastritis treatment.
  • drugs as rebamipide, sofalcone, etc.
  • they should be taken in large amount for a long period of time due to the rather slow actions of these drugs, and thus there is a need for the development of improved drugs.
  • One of the most commonly used methods of assessing the efficiency of gastritis treatment using an animal model is to introduce damage on the gastric mucosa by using non-steroidal anti-inflammatory drugs (NSAID) or ethanol, and observe the rate of recovery.
  • NSAID non-steroidal anti-inflammatory drugs
  • various herbal extracts have been reported as candidates for the treatment of gastritis.
  • the extract of Artemisia Spps having superior effect in treating gastritis has been applied for a patent [Korean Patent Application No. 10-1995-0021957] and developed as a commercial drug named Stillen® by Dong-A Pharmaceutical.
  • the Momordicae semen used in the present invention is a ripe seed of Momordica , a perennial vine which grows widely in southern China and Vietnam. Fruits harvested between September and November are cut in half and the seeds are collected when they are half dry. Or, the fruits are put into jars and the seeds are taken when the rinds become rotten.
  • Momordicae semen is known to have good anti-inflammatory activity and be effective against rheumatic pain, muscular spasm, etc.
  • the Momordicae semen extract is known to contain sterol, oleanolic acid, momordic acid, etc.
  • the present inventors have made extensive efforts to develop a treatment for gastritis. In doing so, they discovered that the Momordicae semen extract and momordica saponin I isolated therefrom reduce the damage of the gastric mucosa induced by diclofenac and alcohols in rats. They also discovered that the administration of Momordicae semen extract and momordica saponin reduces the acidity in the stomach.
  • an object of the present invention is to provide a drug for the prevention and treatment of gastritis or gastric ulcer comprising Momordicae semen extract or momordica saponin I as an active ingredient which is superior in protecting the gastric mucosa and inhibiting gastric acid.
  • the present invention relates to a drug for the prevention and treatment of gastritis or gastric ulcer comprising Momordicae semen extract as an active ingredient.
  • the present invention also relates to a drug for the prevention and treatment of gastritis or gastric ulcer comprising momordica saponin I, which is represented by the following formula (1), as an active ingredient.
  • the present invention relates to a drug comprising Momordicae semen extract and momordica saponin I isolated therefrom, which are effective in the prevention and treatment of gastritis or gastric ulcer with good inhibition activity against the damage of gastric mucosa caused by alcohols and non-steroidal anti-inflammatory drugs (NSAID) such as diclofenac and good inhibition activity against the secretion of gastric acid.
  • NSAID non-steroidal anti-inflammatory drugs
  • the Momordicae semen extract of the present invention is obtained by extracting the herb Momordicae semen 3-10 weight equivalents of water or alcohol solution, according to the common method used to extract herbs.
  • said alcohol is C 1 -C 6 alcohol, more preferably, methanol, ethanol, butanol, etc.
  • the Momordicae semen extract is lyophilized to obtain the extract in powder form. With good activity for the prevention and treatment of the damage of gastric mucosa induced by diclofenac and alcohols, this extract is expected to be very useful as a drug for the prevention and treatment of gastritis or gastric ulcer.
  • the momordica saponin I of the present invention can be efficiently isolated from Momordicae semen by the common method using polar solvent.
  • polar solvent distilled water or alcohol solution may be used.
  • the alcohol is a C 1 -C 6 alcohol, more preferably, methanol, ethanol, butanol, etc.
  • column chromatography may be performed to obtain momordica saponin I with better purity. More specifically, a chromatography column is prepared using octadecylsilylated silica resin, etc. and such adequate solvent as 70% (v/v) aqueous methanol solution, etc. is used to selectively separate the fraction with a high saponin concentration.
  • momordica saponin I is a good candidate for the drug for the prevention and treatment of gastritis or gastric ulcer.
  • the Momordicae semen extract or momordica saponin I of the present invention is prepared into tablet or capsule by the common method.
  • one having activity for the prevention and treatment of gastritis or gastric ulcer can be prepared using a matrix comprising lactose, microcrystalline cellulose, magnesium stearate, etc., and an active ingredient, or the Momordicae semen extract or momordica saponin I of the present invention, at a proportion of 2-10 to 1.
  • the active ingredient may be used either in itself or after mixing with a pharmaceutically acceptable carrier, a forming agent, a diluent to obtain the formulation in the form of powder, granules, capsules, etc.
  • the dosage of Momordicae semen extract or momordica saponin I of the present invention may vary depending on absorption rate, body weight, age, sex, physical conditions, diet, administration time, type of administration, severity of disease, and the like. As a general rule, about 0.1-10 mg per 1 kg of body weight is preferable for the Momordicae semen extract and about 0.05-1 mg per 1 kg of body weight is preferable for the momordica saponin I.
  • the drug in the unit dosage form may be administered through a customized medication plan or several times with predetermined intervals, depending on the decision of an expert who monitors the administration or on the demand of the patients.
  • Momordica saponin I was effectively isolated from the extract prepared in Preparative Example 2 through precipitation using organic solvent (acetone).
  • 10 g of the extract prepared in Preparative Example 2 was dissolved in 100 mL of purified water and 100 mL of acetone was added to obtain 50% (v/v) aqueous acetone solution.
  • Precipitate was filtered off and 400 mL of acetone was further added to the filtrate to obtain 80% (v/v) aqueous acetone solution.
  • the newly formed precipitate was separated using a filter paper and dried.
  • Momordica saponin I was isolated from the 70% (v/v) aqueous methanol solution fraction of Preparative Example 4.
  • High performance liquid chromatography was performed using a mixed solvent of acetonitrile and water (29:71, 0.1% trifluoroacetic acid). Elution was performed at a rate of 9.5 mL/min and the saponin peak was taken at about 45 minutes. This fraction was concentrated under reduced pressure and the solvent was completely removed in a vacuum oven.
  • YMC J‘Sphere ODS-H80 column was used and the measurement was made at 210 nm.
  • Mass spectroscopy and NMR spectroscopy data were compared with those presented in the literature [Iwamoto, Okabe, Yamauchi, Tanaka, Rokutani, Hara, Mihashi, Higuchi. Studies on the constituents of Momordica cochinchinensis Spreng. I. Isolation and characterization of the seed saponins, momordica saponin I and II. Chemical & Pharmaceutical Bulletin 1985, 33(2):464-478].
  • momordica saponin I (3-O- ⁇ -D-galactopyranosyl(1->2)-[ ⁇ -L-rhamnopyranosyl(1->3)]- ⁇ -D-glucuronopyran osido-28-O- ⁇ -D-xylopyranosyl(1->3)- ⁇ -D-glucopyranosyl(1->3)-[ ⁇ -D-xylopyranosyl(1->4)]- ⁇ -L-rhamnopyranosyl(1->2)- ⁇ -D-fucopyranosylgypsogenin), which is known to be present in Momordicae semen .
  • momordica saponin I in the extract or the fraction of Preparative Examples 2 to 4 are given in Table 1 below.
  • a rat model test was performed using 100% ethanol as stomach damage inducing factor to evaluate the protective effect of the Momordicae semen extract for gastric mucosa.
  • the Momordicae semen extract of Preparative Example 1 was dissolved in 0.5% aqueous carboxymethyl cellulose solution to 10 mg/mL and was used as a test drug.
  • Stillen artificialemisia extract, Dong-A Pharmaceutical
  • Mucosta rebamipide, Korea Otsuka Pharmaceuticals
  • the Momordicae semen extract had superior effect of preventing the damage of gastric mucosa induced by alcohol.
  • a rat model test was performed using 100% ethanol as stomach damage inducing factor to evaluate the protective effect of momordica saponin I for gastric mucosa.
  • the momordica saponin I isolated in Preparative Example 5 was dissolved in 0.5% aqueous carboxymethyl cellulose solution to 2 mg/mL and was used as a test drug.
  • Mucosta rebamipide, Korea Otsuka Pharmaceuticals
  • aqueous carboxymethyl cellulose solution to 10 mg/mL was used as control drug.
  • mice Seven-week-old specific pathogen free (SPF) male Sprague-Dawley rats were purchased from Charles River. After 1 week of adaptation, healthy rats with a weight of 220-225 g were selected for the test. Five rats per each group were fasted for 18 hours with drinking water freely available. Momordica saponin I were administered at a dosage of 20 mg/kg and the control drug Mucosta were administered at a dosage of 100 mg/kg. After 30 minutes, 1.5 mL of 100% ethanol was orally administered. 3 hours later, the rats were anesthetized with ether and the stomach was taken out in order to evaluate the drug's effect of preventing the stomach damage. The stomach was cut open along the greater curvature and was observed with eyes. The damage of the stomach was classified into flare, congestion, hemorrhage, inflammation and edema. The severity of the damage was evaluated with points ranging from 0 to 3 (the higher the point, the severer the damage.).
  • momordica saponin I had superior effect of preventing the damage of gastric mucosa induced by alcohol.
  • a rat model test was performed using diclofenac, a representative non-steroidal anti-inflammatory drug (NSAID), as stomach damage inducing factor to evaluate the effect of the Momordicae semen extract of Example 1 for treating gastritis.
  • the Momordicae semen extract was dissolved in 0.5% aqueous carboxymethyl cellulose solution to 10 mg/mL and was used as a test drug.
  • Stillen artificialemisia extract, Dong-A Pharmaceutical
  • Mucosta rebamipide, Korea Otsuka Pharmaceuticals
  • diclofenac and the test drug were administered simultaneously and the damage of gastric mucosa was observed 6 hours later.
  • the test drug was administered abdominally. Similar to that in Example 3, diclofenac and the test drug were dissolved in 0.5% aqueous carboxymethyl cellulose solution to 10 mg/mL.
  • mice Seven-week-old specific pathogen free (SPF) male Sprague-Dawley rats were purchased from Charles River. After 1 week of adaptation, healthy rats with a weight of 220-225 g were selected for the test. Five rats per each group were fasted for 18 hours with drinking water freely available and diclofenac was orally administered at a dosage of 40 mg/kg and, at the same time, the test drug, or the Momordicae semen extract, and the control drugs Stillen and Mucosta were abdominally administered at a dosage of 100 mg/kg. 6 hours later, the rats were anesthetized with ether and the stomach was taken out in order to evaluate the drug's effect of treating gastritis. The stomach was cut open along the greater curvature and was observed with eyes. The damage of the stomach was classified into flare, congestion, hemorrhage, inflammation and edema. The severity of the damage was evaluated with points ranging from 0 to 3.
  • the Momordicae semen extract had the effect of treating the damaged gastric mucosa in addition to the capability of reducing the damage of gastric mucosa induced by NSAIDs, when administered along with NSAIDs such as diclofenac.
  • Diclofenac and the test drug were administered simultaneously and the damage of gastric mucosa was observed 4 hours later.
  • Diclofenac was dissolved in 0.5% aqueous carboxymethyl cellulose solution to 40 mg/mL and the test drug was prepared as in Example 2.
  • mice Seven-week-old specific pathogen free (SPF) male Sprague-Dawley rats were purchased from Charles River. After 1 week of adaptation, healthy rats with a weight of 220-225 g were selected for the test. Five rats per each group were fasted for 18 hours with drinking water freely available and diclofenac was orally administered at a dosage of 40 mg/kg and, at the same time, the test drug, or momordica saponin I, was orally administered at a dosage of 20 mg/kg and the control drug Mucosta was orally administered at a dosage of 100 mg/kg. 4 hours later, the rats were anesthetized with ether and the stomach was taken out in order to evaluate the drug's effect of treating gastritis.
  • SPPF pathogen free
  • the stomach was cut open along the greater curvature and was observed with eyes.
  • the damage of the stomach was classified into flare, congestion, hemorrhage, inflammation and edema.
  • the severity of the damage was evaluated with points ranging from 0 to 3 (The higher the point, the severer the damage).
  • momordica saponin I had the ability of reducing the damage of gastric mucosa caused by NSAIDs such as diclofenac.
  • Momordica saponin I was orally administered to Sprague-Dawley rats and the acidity in the stomach was measured in order to evaluate the effect of momordica saponin I on the secretion of gastric acid.
  • the momordica saponin I isolated in Preparative Example 4 was dissolved in 0.5% aqueous carboxymethyl cellulose solution to concentrations of 0.5, 1.5 and 4.5 mg/mL.
  • 7-week-old specific pathogen free (SPF) male Sprague-Dawley rats were purchased from Charles River. After 1 week of adaptation, healthy rats with a weight of 220-225 g were selected for the test.
  • momordica saponin I effectively reduced the acidity of the gastric juice and thus can be useful in treating gastritis or gastric ulcer.
  • Acute toxicity test was performed as follows using 6-week-old specific pathogen free (SPF) Sprague-Dawley rats
  • the Momordicae semen extract prepared in Preparative Example 1 was orally administered once at a dosage of 1 g/kg. Survival, clinical manifestations and body weight change were observed and hematological and serum biochemical analysis was performed. Autopsy was performed to observe abnormalities in abdominal and thoracic organs. There was no noticeable clinical manifestation or death. In addition, no toxicity was found in body weight change, hematological and serum biochemical analysis and autopsy.
  • the Momordicae semen extract of the present invention showed no toxicity in all rats up to the dosage of 2,000 mg/kg and was proved to be a safe substance with a minimum oral administration lethal dose (LD 50 ) of 2,000 mg/kg or larger.
  • LD 50 minimum oral administration lethal dose
  • Acute toxicity test was performed as follows using 6-week-old specific pathogen free (SPF) Sprague-Dawley rats
  • the momordica saponin I isolated in Preparative Example 5 was orally administered once at a dosage of 400 mg/kg. Survival, clinical manifestations and body weight change were observed and hematological and serum biochemical analysis was performed. Autopsy was performed to observe abnormalities in abdominal and thoracic organs. There was no noticeable clinical manifestation or death. In addition, no toxicity was found in body weight change, hematological and serum biochemical analysis and autopsy.
  • the momordica saponin I of the present invention showed no toxicity in all rats up to the dosage of 400 mg/kg and was proved to be a safe substance with a minimum oral administration lethal dose (LD 50 ) of 400 mg/kg or larger.
  • LD 50 minimum oral administration lethal dose
  • the Momordicae semen extract of the present invention was prepared into tablet for oral administration by wet granulation and dry granulation.
  • Momordicae semen extract 200 mg
  • light anhydrous silica acid 10 mg
  • magnesium stearate 2 mg
  • microcrystalline cellulose 50 mg
  • sodium starch glycolate 25 mg
  • cornstarch 113 mg
  • anhydrous ethanol anhydrous ethanol (adequate).
  • the momordica saponin I of the present invention was prepared into tablet for oral administration by wet granulation and dry granulation.
  • Momordica saponin I (20 mg), light anhydrous silica acid (10 mg), magnesium stearate (2 mg), microcrystalline cellulose (50 mg), sodium starch glycolate (25 mg), cornstarch (113 mg), anhydrous ethanol (adequate).
  • the Momordicae semen extract of the present invention was prepared into ointment.
  • Momordicae semen extract (5 g), cetyl palmitate (20 g), cetanol (40 g), stearyl alcohol (40 g), isopropyl myristate (80 g), sorbitan monostearate (20 g), polysorbate (60 g), propyl p-hyroxybenzoate (1 g), methyl p-hyroxybenzoate (1 g), phosphoric acid and purified water (adequate).
  • the Momordicae semen extract of the present invention was prepared into injection.
  • the Momordicae semen extract of the present invention was prepared into a transdermal agent.
  • Momordicae semen extract (0.4 g), sodium polyacrylate (1.3 g), glycerin (3.6 g), aluminum hydroxide (0.04 g), methyl paraben (0.2 g), water (14 g).
  • Momordicae semen extract (0.8 g), propylene glycol (1.6 g), liquid paraffin (0.8 g), isopropyl myristate (0.4 g), gelba 1430 (16.4 g).
  • the momordica saponin I of the present invention was prepared into a transdermal agent.
  • Momordica saponin I (40 mg), propylene glycol (1.6 g), liquid paraffin (0.8 g), isopropyl myristate (0.4 g), gel bar 1430 (16.4 g).
  • the Momordicae semen extract in accordance with the present invention and momordica saponin I isolated therefrom are very useful for the prevention and treatment of gastritis or gastric ulcer as they have superior effects in preventing the damage of gastric mucosa induced by alcohols and non-steroidal anti-inflammatory drugs (NSAID) and also inhibiting the secretion of gastric acid.
  • NSAID non-steroidal anti-inflammatory drugs

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US12/096,881 2005-12-20 2006-12-20 Anti-Gastritis and Anti-Ulcer Agent Containing Momordicae Semen Extract and Momordica Saponin I Isolated From the Same Abandoned US20090004309A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
KR1020050126302A KR20070065652A (ko) 2005-12-20 2005-12-20 위염 예방 및 치료에 유용한 목별자 추출물
KR10-2005-012302 2005-12-20
KR10-2006-0128138 2006-12-14
KR1020060128138A KR101132730B1 (ko) 2006-12-14 2006-12-14 위염 또는 위궤양 예방 및 치료에 유용한 모모르디카사포닌ｉ
PCT/KR2006/005603 WO2007073096A1 (en) 2005-12-20 2006-12-20 Anti-gastritis and anti-ulcer agent containing momordicae semen extract and momordica saponin i isolated from the same

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US (2) US20090004309A1 (ru)
EP (1) EP1962865A4 (ru)
JP (1) JP5231244B2 (ru)
AU (1) AU2006328064B2 (ru)
BR (1) BRPI0620129A2 (ru)
RU (1) RU2429000C2 (ru)
WO (1) WO2007073096A1 (ru)

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US8071844B1 (en) 2007-09-13 2011-12-06 Nutritional Health Institute Laboratories, Llc Cultivated momordica species and extract thereof
KR20090040670A (ko) * 2007-10-22 2009-04-27 에스케이케미칼주식회사 상처 치료 촉진 효과를 갖는 목별자 추출물
US8877259B2 (en) 2012-02-09 2014-11-04 Mary Kay Inc. Cosmetic formulation

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KR950007046B1 (ko) * 1992-04-11 1995-06-30 이형주 생약함유 화장수 및 그 제조방법
KR960012276B1 (ko) * 1994-04-21 1996-09-18 이형주 생약함유 미용비누 및 그 제조방법
JPH1059858A (ja) 1996-08-21 1998-03-03 Res Inst For Prod Dev 抗糖尿病剤
JPH11302180A (ja) * 1998-04-16 1999-11-02 Joji Yamahara 抗潰瘍剤
CN1100554C (zh) * 1999-01-19 2003-02-05 刘明堂 一种根治胃下垂的中成药
KR20030021714A (ko) * 2001-09-07 2003-03-15 에스케이케미칼주식회사 독성이 없이 추출된 생약추출물이 복합처방된 생약조성물과 그 제조방법

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RU2429000C2 (ru) 2011-09-20
AU2006328064A1 (en) 2007-06-28
JP2009520020A (ja) 2009-05-21
EP1962865A4 (en) 2010-04-28
JP5231244B2 (ja) 2013-07-10
EP1962865A1 (en) 2008-09-03
AU2006328064B2 (en) 2012-11-15
RU2008129710A (ru) 2010-01-27
WO2007073096A1 (en) 2007-06-28
US20100310687A1 (en) 2010-12-09
BRPI0620129A2 (pt) 2011-11-01

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