US20150175715A1 - Process for Preparation of a Grifola frondosa Polysaccharide F2 and Its Hypoglycemic Activity - Google Patents

Process for Preparation of a Grifola frondosa Polysaccharide F2 and Its Hypoglycemic Activity Download PDF

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Publication number
US20150175715A1
US20150175715A1 US14/549,184 US201414549184A US2015175715A1 US 20150175715 A1 US20150175715 A1 US 20150175715A1 US 201414549184 A US201414549184 A US 201414549184A US 2015175715 A1 US2015175715 A1 US 2015175715A1
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Prior art keywords
grifola frondosa
polysaccharide
diabetes
frondosa polysaccharide
preparation
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US14/549,184
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Qingping Wu
Chun Xiao
Yizhen Xie
Xiaobing Yang
Senzhu Li
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Guangdong Institute of Microbiology
Guangdong Yuewei Edible Mushroom Technology Co Ltd
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Guangdong Institute of Microbiology
Guangdong Yuewei Edible Mushroom Technology Co Ltd
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Assigned to GUANGDONG INSTITUTE OF MICROBIOLOGY reassignment GUANGDONG INSTITUTE OF MICROBIOLOGY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LI, SENZHU, WU, QINGPING, XIAO, Chun, XIE, YIZHEN, YANG, XIAOBING
Assigned to GUANGDONG INSTITUTE OF MICROBIOLOGY, GUANGDONG YUEWEI EDIBLE FUNGI TECHNOLOGY CO., LTD. reassignment GUANGDONG INSTITUTE OF MICROBIOLOGY CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE INFORMATION PREVIOUSLY RECORDED ON REEL 034410 FRAME 0637. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Assignors: LI, SENZHU, WU, QINGPING, XIAO, Chun, XIE, YIZHEN, YANG, XIAOBING
Publication of US20150175715A1 publication Critical patent/US20150175715A1/en
Priority to US15/414,255 priority Critical patent/US10155822B2/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0003—General processes for their isolation or fractionation, e.g. purification or extraction from biomass
    • 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
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/06—Fungi, e.g. yeasts
    • A61K36/07—Basidiomycota, e.g. Cryptococcus
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine

Definitions

  • This invention relates to a Grifola frondosa polysaccharide F2 with hypoglycemic activity, preparation method and use thereof, belonging to the field of bio-medicine.
  • Diabetes is a metabolic disorder syndrome characterized by hyperglycemia.
  • the number of diabetes patients around the world has been increasing at a speed of 6 percent each year. Between 2010 and 2030, the number of adults with diabetes was expected to increase by 69% in developing countries and by 20% in developed countries. Diabetes includes type 1 and type 2 diabetes, with type 2 diabetes accounting more than 90% of all cases of diabetes.
  • There is currently no known method to conquer diabetes and the patients' conditions are generally controlled and alleviated by orally administered drugs for a long-term. But most of current drugs for diabetes are chemical or biochemical drugs, which have much side effects. Based on this critical situation, safer and more effective treatment modalities for diabetes are therefore needed to address the increase in prevalence of diabetes.
  • a polysaccharide with hypoglycemic activity was obtained from fruit body of cultivated Grifola frondosa by Xun Ma— ⁇ -glucan with a molecular weight of 400-450 KD.
  • Kubo obtained a glycoprotein after adding one volume of ethanol into the hot water extract to generate suspension and centrifugation.
  • 5 ⁇ 105 D showed a significant hypoglycemic activity. Structure analysis indicated that it was a ⁇ -1,6-glucan with ⁇ -1,4-branch.
  • the possible action mechanism of MT- ⁇ -glucan from the fruit body of Grifola frondosa was increasing sensitivity of insulin and improving insulin resistance of the surrounding tissue through increasing the number of insulin receptor.
  • Water soluble extract FXM from Grifola frondosa potentially decreased blood serum glucose by improvement the insulin resistance.
  • Glycoprotein SX from fruit body of Grifola frondosa can improve glucose tolerance and increase the body's sensitivity to insulin.
  • the object of this invention is to provide a new Grifola frondosa polysaccharide F2 with hypoglycemic activity and preparation method thereof.
  • a process for preparation of the above-mentioned Grifola frondosa polysaccharide F2 comprising:
  • the said precipitation in the step (a) is dissolved into hot water, filtered by a 0.45 ⁇ m millipore filter and then dialyzed in dialysis bag of 3000 D for 24 h to yield crude polysaccharides solutions.
  • concentration of crude polysaccharide in the Grifola frondosa crude polysaccharides solution is adjusted, and then be used as the sample of chromatographic separation in the step (b).
  • the said polysaccharide F2 from Grifola frondosa has a molecular weight of 4.52 ⁇ 10 5 D.
  • the contents of polysaccharides and protein are respectively 95.6% and 3.6%.
  • the said polysaccharides is mainly consisted of glucose, mannose, xylose, galactose, and arabinose; the amino acids mainly comprises: proline(Pro), serine(Ser), asparitic acid(Asp), lysine(Lys), alanine(Ala), glutamic acid(Glu), threonine(Thr), glycine(Gly), arginine(Arg), leucine(Leu) and valine(Val).
  • the said polysaccharide F2 is a ⁇ -heteropolysaccharides composed of uronic acids. Based on the above-mentioned parameters, there is no known analogous polysaccharide in the existing technology, that is to say, Grifola frondosa polysaccharide F2 of this invention is a new Grifola frondosa polysaccharide.
  • the second object of the invention is to provide the use of Grifola frondosa polysaccharide F2 in manufacturing a drug for the treatment of diabetes, especially for type 2 diabetes.
  • Another object of the invention is to provide a drug for the treatment of diabetes, characterized in that the drug comprises Grifola frondosa polysaccharide F2 as active ingredients.
  • the said diabetes is type 2 diabetes.
  • This invention isolates a new Grifola frondosa polysaccharide F2 with hypoglycemic activity from the fruit body of Grifola frondosa. It can be used in manufacturing a drug for the treatment of diabetes, especially for type 2 diabetes.
  • the invention makes a foundation for developing new anti-diabetes agents in the future, and actively promotes the study on active ingredients of natural medicine for treating diabetes.
  • FIG. 1 shows the elution curve of the precipitation on DEAE Sepharose Fast Flow chromatography.
  • FIG. 2 shows the calibration curve of the standard polysaccharides on Gel permeation chromatography.
  • FIG. 3 shows the HPLC chromatogram of Grifola frondosa polysaccharide F2.
  • FIG. 4 shows the Infrared spectrum (IR) of Grifola frondosa polysaccharide F2.
  • FIG. 5 shows the 1 H-NMR spectrum of Grifola frondosa polysaccharide F2.
  • FIG. 6 shows the 13 C-NMR spectrum of Grifola frondosa polysaccharide F2.
  • the fruit bodies of Grifola frondosa were homogenized to a fine powder and extracted with hot water(5000 mL, 80) for 8 hours.
  • the mixture was filtered and the filtrate was concentrated to 1000 mL under reduced pressure, then precipitated with 4 volume of absolute ethanol.
  • the precipitation was obtained by centrifugation at a speed of 5000 rpm.
  • the precipitation was dissolved into hot water, filtered by a 0.45 ⁇ m millipore filter and dialyzed in dialysis bag of 3000 D for 24 h to yield crude polysaccharides solution. Finally the concentration of the solution was adjusted to be 10 mg/mL.
  • Grifola frondosa polysaccharide F2 (10 mg) was dissolved into the ultrapure water (1 mL) and analyzed by HPLC.
  • GPC calibration curve 10 mg polysaccharides with Mr of 738, 5800, 1.22 ⁇ 10 4 , 2.37 ⁇ 10 4 , 4.80 ⁇ 10 4 , 1.00 ⁇ 10 5 , 1.86 ⁇ 10 5 , 3.80 ⁇ 10 5 , 8.53 ⁇ 10 5 D were used as standards, dissolved into 0.05M NaH 2 PO 4 —Na 2 HPO 4 buffer (1 mL, pH 6.7) containing 0.05% NaN 3 , filtered by a 0.45 ⁇ m millipore filter and analyzed by GPC. The retention times of the standard polysaccharides with the known Mr were shown in table 1. GPC calibration curve was established with elution volume of the standard polysaccharides as the abscissa and the value of Mr as the vertical coordinates, see FIG. 2 .
  • Grifola frondosa polysaccharide F2 10 mg Grifola frondosa polysaccharide F2 was dissolved in 0.05M NaH 2 PO 4 —Na 2 HPO 4 buffer (1 mL, pH 6.7) containing 0.05% NaN 3 , filtered by a 0.45 ⁇ m millipore filter and analyzed by GPC.
  • the average molecular weight of Grifola frondosa polysaccharide F2 is 4.52 ⁇ 10 5 D (as shown in FIG. 3 ), calculated automatically by GPC chromatographic working station.
  • the content of polysaccharides of F2 is 95.6% determined by phenol sulfuric acid method, and that of protein is 3.6% determined by Bradford method.
  • HPLC HP1050, America
  • HP1050 consisted of quaternary gradient pump, automatic sampler, column oven and HP1046A fluorescence detector; Full-automatic high Speed Freezing Centrifuge (2000 rpm, GL20A, Japan).
  • Standard solution standard amino acids were dissolved into 0.1 mol ⁇ L ⁇ 1 HCl solution, and diluted to standard solution, in which the concentration of each amino acid was 250 nM.
  • the amino acids of Grifola frondosa polysaccharide F2 mainly comprises: proline(Pro), serine(Ser), asparitic acid(Asp), lysine(Lys), alanine(Ala), glutamic acid(Glu), threonine(Thr), glycine(Gly), arginine(Arg), leucine(Leu) and valine(Val). See table 2.
  • Acetylation the above-mentioned hydrolysate was evaporated to dryness.
  • the residue sample was converted to acetylated derivatives with 70 mg hydroxylamine hydrochloride and 5 mL pyridine for 1 hour at 90° C. by water bath heating. After slightly cooling, 5 mL acetic anhydride was then added with heating at 90° C. After 1 hour, 10 mL water was added to break the anhydride and the acetylated products was extracted with chloroform. The extract liquor was washed with water and then subsequently dehydrated with anhydrous Na 2 SO 4 . The supernate was concentrated to 1 mL under nitrogen and analyzed by using GC-MS.
  • GC-MS operation conditions SE230 elastic quartz capillary column (15 m ⁇ 012 mm ⁇ 0133 Lm); the temperature program was set to increase to 280 from 100 at a rate of 10/min, then holding for 10 min at 280; carrier gas: Helium; column pressure: 70 kPa; split ratio:10:1; solvent delay:2 min; electron ionization mode: EI; electron energy:70 eV; quadrupole rod temperature:150; temperature of ion source:230; voltage of electron multiplier:2300V; interface temperature of GC-MS:280; Mass scanned range (m/z): 29 ⁇ 500.
  • Grifola frondosa polysaccharide F2 was analyzed by GC-MS after hydrolysis and acetylation, as control, the standard monosaccharides was acetylated simultaneously. According to the total ions chromatogram of standard monosaccharides, it can be inferred that Grifola frondosa polysaccharide F2 is a heteropolysaccharide mainly consisted of glucose, mannose, xylose, galactose, arabinose and ribose. The relative content of the monosaccharides were shown in table 3.
  • the number of glycoside residues and their relative contents can be determined by the number of peaks in the resonance area of anomeric carton (90-110 ppm).
  • the chemical shifts of anomeric carbons from ⁇ -glucosides are in the range of 95-101 ppm, while that of ⁇ -glucosides in the range of 101-105 ppm.
  • the chemical shifts of Grifola frondosa polysaccharide F2 are respectively at 97.94 ppm, 101.30 ppm, 102.26 ppm, 102.92 ppm and 115.47 ppm, it is consequently considered as a ⁇ -heteropolysaccharide.
  • the characteristic signals of 13 C-NMR can determine some glycoside residues and groups, for example, the signals of carboxyls-C of uronic acids are in the range of 170-180 ppm, and the chemical shifts of Grifola frondosa polysaccharide F2 are respectively at 171.81 ppm, 173.32 ppm, 174.37 ppm, 177.68 ppm and 177.53 ppm, as a consequence, Grifola frondosa polysaccharide F2 contains uronic acids.
  • Grifola frondosa polysaccharide F2 of the invention has a molecular weight of 4.52 ⁇ 10 5 D.
  • the contents of polysaccharides and protein are respectively 95.6% and 3.6%.
  • the said polysaccharides is mainly consisted of glucose, mannose, xylose, galactose, and arabinose; the amino acids mainly comprises: proline(Pro), serine(Ser), asparitic acid(Asp), lysine(Lys), alanine(Ala), glutamic acid(Glu), threonine(Thr), glycine(Gly), arginine(Arg), leucine(Leu) and valine(Val).
  • the said polysaccharide F2 is a ⁇ -pyran heterocyclic polysaccharide containing uronic acids. Based on the above-mentioned parameters, there is no known analogous polysaccharide in the existing technology. Therefore, Grifola frondosa polysaccharide F2 of this invention is a new Grifola frondosa polysaccharide.
  • FBG were decreased significantly (*P ⁇ 0.05) afterdiabetic rats were continuously administered Grifola frondosa polysaccharide F2 (100 mg/kg BW) for 2 weeks by intragastric infusion.
  • Grifola frondosa polysaccharide F2 of the invention can be used to manufacture medicaments for the treatment of diabetes, especially for type 2 diabetes.

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CN113109489A (zh) * 2021-05-21 2021-07-13 夏永刚 同时定性和定量分析中药多糖中醛糖、酮糖、糖醇、糖酸酸和氨基糖的方法

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CN108159069A (zh) * 2018-01-26 2018-06-15 广东省微生物研究所（广东省微生物分析检测中心） 灰树花多糖f2在制备治疗高脂血症药物、预防或延缓动脉粥样硬化药物中的应用
CN109932446A (zh) * 2019-03-21 2019-06-25 苏州大学 一种枸杞多糖提取物的检测方法
CN112225827A (zh) * 2020-10-15 2021-01-15 广东粤微生物科技有限公司 一种灰树花活性多糖的提取方法及提取的活性多糖和用途
CN113651900B (zh) * 2021-10-10 2022-11-15 吉林农业大学 一种具有调节血脂功能的灰树花纯化多糖及制备方法
CN114230646B (zh) * 2021-12-07 2023-07-04 广东省科学院微生物研究所(广东省微生物分析检测中心) 一种抗肿瘤灰树花糖蛋白及其制备方法和应用
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