CN101016321A - Two flavone glycosides in dandelion and medical use for against Gram-positive bacterium thereof - Google Patents
Two flavone glycosides in dandelion and medical use for against Gram-positive bacterium thereof Download PDFInfo
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- CN101016321A CN101016321A CN 200710067180 CN200710067180A CN101016321A CN 101016321 A CN101016321 A CN 101016321A CN 200710067180 CN200710067180 CN 200710067180 CN 200710067180 A CN200710067180 A CN 200710067180A CN 101016321 A CN101016321 A CN 101016321A
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- taraxacum
- glycosides
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Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a flavonoid glycoside and medical salt and application to prevent Micrococcus pyogenes and beta hemolytic streptococcus, which is characterized by the following: preventing pustule, toxic epidermal decay, acute myocarditis, cystitis, cervicitis and tumour of neutral nerve system; fitting for treating prostatitis, pneumococcus, medullitis and knuckle disease.
Description
Technical field
The present invention relates to medical technical field.Particularly, the present invention relates to from taraxacum to separate the flavonoid glycoside that obtains and pharmacologically acceptable salt thereof, its anti-infectives purposes with two kinds of novel structures that control streptococcus aureus and/or beta hemolytic streptococcus catch, and the pharmaceutical composition that contains these compounds.Can expect that it is used to prevent and treat streptococcus aureus and/or beta hemolytic streptococcus infects furuncle, warts, toxicity epidermis decomposition, pneumonia, osteomyelitis, acute myocarditis, endocarditis, meningitis, mazoitis, urocystitis, pelvic inflammatory disease, urinary tract inflammation, prostatitis, microbemia, toxic shock syndrome, poradenolymphitis, sacroiliitis, pharyngitis, the trachelitis that causes, and the abscess of muscle, skin, urodeum, central nervous system.
Technical background
Streptococcus aureus (Staphylococcus aureus) is the Gram-positive coccus, the streptococcus aureus (MRSA) in anti-methyl XiLin is the bacterial strain that begins to occur the eighties in 20th century, it is the epiphytotics main pathogeny of microorganism in the hospital and clinically, the main infection that causes the people has furuncle, warts, toxicity epidermis decomposition, pneumonia, osteomyelitis, acute myocarditis, mazoitis, urocystitis, prostatitis, microbemia, toxic shock syndrome, poradenolymphitis, pharyngitis, trachelitis, pelvic inflammatory disease, and muscle, skin, urodeum, the abscess of central nervous system.So be that HUMAN HEALTH is influenced great pathogenic species.Suis (Streptococcus species) is into catenation, amphimicrobian Gram-positive bacillus.Medically common pathogenic suis major part belongs to β haemolysis type.They are present on people's the mucous membrane of skin, respiratory tract, digestive tube and urodeum, can cause skin, respiratory tract and soft group of tissue infection such as diseases such as pneumonia, microbemia, endocarditis, meningitis, urinary tract inflammation and sacroiliitis.
Chinese traditional medicine is a resourceful treasure-house.Wherein many medicinal plants all contain the effect of good restraining streptococcus aureus (being called for short " golden Portugal bacterium ") and beta hemolytic streptococcus.Taraxacum is feverfew taraxacum (Taraxacum mongolicum Hand-Mazz also claims Mongolian taraxacum) or the dry herb that belongs to several plants together, is heat-clearing and detoxifying herb, and the function of heat-clearing, detoxifcation, diuresis, dissipating bind is arranged; Cure mainly acute mastitis, furunculosis, hot eyes, pharyngalgia, jaundice due to damp-heat and heat and drench puckery pain etc.Clinical is to be usually used in treating diseases such as acute mastitis, lymphadenitis, treatment carbuncle toxin, acute conjunctivitis, cold, fever, acute tonsillitis, acute bronchitis, hepatitis, swollen capsulitis and urinary tract infections.Taraxacum mainly contains compounds such as triterpenes, phytosterol, sesquiterpene lactones class, coumarins, flavonoid, phenolic acids, carotenoid and fatty acid.Its pharmacological action has antisepsis and anti-inflammation, anti-oxidant, hepatic cholagogic, immunomodulatory and antitumor etc.At present, injection, tablet and the granule etc. that utilize the taraxacum single medicinal material to make are widely used in clinical, treat various diseases associated with inflammation and have obtained curative effect preferably.
Taraxacum has stronger heat-clearing toxin-expelling functions, have higher research and development and be worth, but domestic research to taraxacum mainly rests on its crude extract, especially lacks the effective substance correlative study.Domestic correlative study report and patent generally all are to use with the compound form, rare from taraxacum extracting effective components and the report studied at its bacteriostatic activity.More comprehensive abroad to the chemical constitution study of common dandelion (Taraxacum officinale), find that it mainly contains sesquiterpene, triterpene and flavones ingredient, the pharmacologically active report is less, and does not see the chemical constitution study report at Mongolian taraxacum (T.mongolicum).Domestic chemical constitution study report to the Dandelion plant is very few, quotes the chemical ingredients of common dandelion Taraxacum officinale more, and the result for retrieval seminar that finds to reach the clouds has carried out the research report to the chemical ingredients of Mongolian taraxacum and [reaches the clouds at present, Bao Yanyan, Zhu Lili, Zheng Junhua, Cai Shaoqing, Xiao Yue, the taraxacum The Chemical Constituents, Chinese Pharmaceutical Journal, 1997,32,584-586; Reach the clouds Bao Yanyan, Zhang Yonglin, Cai Shaoqing, Zheng Junhua, taraxacum The Chemical Constituents, the Navy General Hospital journal, 1998,11,167-169], be divided into 5 compounds: β-Gu Zaichun, Quercetin, coffic acid, chlorogenic acid and luteolin-7-oxygen-glucoside, and other chemical ingredients it be not immediately clear.For understanding the chemical constitution of each polar fraction of T.mongolicum, we have carried out the fitochemical studies of system to it.Result of study shows that high polarity position chief component is flavonoid glycoside and polyphenolic compound.
Summary of the invention
The purpose of this invention is to provide a kind of flavonoid glycoside compound Mongolia taraxacum glycosides A and Mongolian taraxacum glycosides B and pharmacologically acceptable salt and antibacterial application that from composite family taraxacum plant, obtains;
Another object of the present invention has provided The compounds of this invention is used to prepare prevention and treats the furuncle that is caused by streptococcus aureus and/or beta hemolytic streptococcus, warts, toxicity epidermis decomposition, pneumonia, osteomyelitis, acute myocarditis, endocarditis, meningitis, mazoitis, urocystitis, pelvic inflammatory disease, urinary tract inflammation, prostatitis, microbemia, toxic shock syndrome, poradenolymphitis, sacroiliitis, pharyngitis, trachelitis, and muscle, skin, urodeum, the medicine of the abscess of central nervous system and medicine or the healthcare products purposes relevant with above-mentioned disease;
Another object of the present invention has provided the pharmaceutical composition that contains flavonoid glycoside compound of the present invention.
The present invention prepares following compound 1 and 2 by extracting from the feverfew taraxacum, concrete structure is as follows:
Compound 1 (Mongolian taraxacum glycosides A)
Compound 2 (Mongolian taraxacum glycosides B)
Two monoterpene glycoside compound titles are respectively:
Compound 1 (Mongolian taraxacum glycosides A): Isoetin-7-oxygen-β-glucopyranose base-2 '-oxygen-α-pyranose form Arabinoside;
Compound 2 (Mongolian taraxacum glycosides B): Isoetin-7-oxygen-β-glucopyranose base-4 '-oxygen-α-glucopyranoside.
Flavonoid glycoside compound 1 and 2 is mainly derived from each position of feverfew taraxacum, preferably from taraxacum (claiming Mongolian taraxacum again) (Taraxacum mongolicum Hand-Mazz), alkali ground taraxacum (claiming magnificent taraxacum again) (Taraxacum sinicumKitag), hot river taraxacum (claiming white edge taraxacum again) (TaraxacumplatypecidumDiels), Herba Taraxaci ohwiani (Taraxacum ohwianumKitag), anti-luxuriant taraxacum (Taraxacum grypodon Dahlst), taraxacum (the Taraxacm of Xingan, falcilobum Kitag) common taraxacum medicinal material rhizome on the Chinese drug market such as, leaf, flower comprises preparing in its dry product and the bright product and getting.The herb part of preferred taraxacum (claim not only Mongolian taraxacum) (Taraxacum mongolicum Hand-Mazz) and/or alkali ground taraxacum (but also claiming magnificent taraxacum) (Taraxacum sinicum Kitag).
Characteristics of the present invention are, from feverfew taraxacum rhizome, leaf, flower separates its efficient part of purifying in the position, and therefrom obtain two monomeric compounds, through the chemical assay structure is flavonoid glycoside compound 1 and 2, and very strong inhibition streptococcus aureus and beta hemolytic streptococcus acts on before finding its tool, provide and to have expected to be used to prepare to cause or relevant physiological change or treatment of diseases medicine and prevention and health care product with gram-positive bacteria especially streptococcus aureus and beta hemolytic streptococcus, include but not limited to furuncle, warts, toxicity epidermis decomposition, pneumonia, osteomyelitis, acute myocarditis, endocarditis, meningitis, mazoitis, urocystitis, pelvic inflammatory disease, urinary tract inflammation, prostatitis, microbemia, toxic shock syndrome, poradenolymphitis, sacroiliitis, pharyngitis, trachelitis, and muscle, skin, urodeum, the abscess of central nervous system.
Specific embodiments
Plant is in the past discovered and is contained triterpenes, coumarins, phenolic acids (flavonoid that comprises phenolic hydroxy group), sesquiterpenoids, phytosterol, carotenoid and long-chain fat acid compounds in the taraxacum plant.The inventor is to the high polarity position of this plant milk extract, obtain this by multiple positive and negative phase chromatography means and effectively suppress streptococcus aureus and active two active compounds of beta hemolytic streptococcus, and derive two flavonoid glycoside compounds that its chemical structure was not reported for forefathers through integration analysis such as infrared, mass spectrum, ultraviolet and NMR (Nuclear Magnetic Resonance) spectrum.
Medicinal material among the present invention can be the arbitrary position of home-made Dandelion plant in any one, promptly can be taraxacum (claiming Mongolian taraxacum again) (Taraxacum mongolicum Hand-Mazz), alkali ground taraxacum (claiming magnificent taraxacum again) (Taraxacum sinicum Kitag), hot river taraxacum (claiming white edge taraxacum again) (Taraxacum platypecidumDiels), Herba Taraxaci ohwiani (Taraxacum ohwianumKitag), anti-luxuriant taraxacum (Taraxacum grypodonDahlst), common taraxacum medicinal material on the Xingan taraxacum Chinese drug markets such as (Taraxacum falcilobumKitag), can be dry product or bright product, it can be the root of taraxacum medicinal material plant, stem, leaf, flower, seed, skin, fruit, also can be their mixture, all be called for short taraxacum in the present invention's the specification sheets.Preferred herb.The more preferably herb part of taraxacum (claim not only Mongolian taraxacum) (Taraxacummongolicum Hand-Mazz) and/or alkali ground taraxacum (but also claiming magnificent taraxacum) (Taraxacum sinicumKitag).
Two novel flavonoid glycoside compositions that the present invention obtains have the function that suppresses streptococcus aureus and beta hemolytic streptococcus growth; Can be used to prevent and treat furuncle, warts, toxicity epidermis decomposition, pneumonia, osteomyelitis, acute myocarditis, endocarditis, meningitis, mazoitis, urocystitis, pelvic inflammatory disease, urinary tract inflammation, prostatitis, microbemia, toxic shock syndrome, poradenolymphitis, sacroiliitis, pharyngitis, the trachelitis that causes by streptococcus aureus and beta hemolytic streptococcus, and the abscess and medicine or the healthcare products purposes relevant with above-mentioned symptom or disease of muscle, skin, urodeum, central nervous system; Thereby may develop the anti-infection drug composition.This pharmaceutical composition can be made various formulations with the routine techniques in the pharmacy field, as tablet, granule, capsule, oral liquid, dripping pill, injection, transdermal patch, aerosol etc.
Further specify the present invention below by embodiment.The following embodiment of mandatory declaration is used to illustrate the present invention rather than limitation of the present invention.Essence according to the present invention all belongs to the scope of protection of present invention to the simple modifications that the present invention carries out.
Embodiment 1Mongolia taraxacum glycosides A and Mongolian taraxacum glycosides B separate:
1.1 instrument and reagent
Fusing point is measured with micro-fusing point instrument (production of Beijing Imtech), and temperature is not proofreaied and correct; Optically-active is produced on the automatic polarimeter of Polax-2L type in Japan and is measured; Infrared spectra (IR) is by Bruker Vector-22 determination of infrared spectroscopy, through the KBr compressing tablet; UV spectrum is measured with Shimadzu UV-240 ultraviolet spectrophotometer; Proton nmr spectra (
1H-NMR), carbon-13 nmr spectra (
13C-NMR) and two dimensional NMR wave spectrum (2D NMR) measure (tetramethylsilane ether TMS is interior mark) by INOVA type NMR spectrometer with superconducting magnet (VARIAN INOVA-400 MHz); Electrospray ionization mass spectrum (ESI-MS) is measured by Bruker Esquire 3000+ mass spectrograph, and column chromatography is produced by Haiyang Chemical Plant, Qingdao with silica GF254 (10-40 order) with silica gel (100-200 order, 200-300 order and 300-400 order) thin-layer chromatography; Agents useful for same is analytical pure, and wherein the sherwood oil boiling range is 60-90 ℃; Thin layer preparative chromatography (PTLC) the aluminium foil silica-gel plate of Merck company; Column chromatography adopts the biochemical plastic molding and processing plant of Taizhou, Zhejiang Province city road and bridge tetramethyl product with polymeric amide (14-30 order and 100-200 order); Dextrane gel (Sephadex LH-20) adopts Sweden AmershamPharmacia BiotechAB company product; Reverse phase silica gel RP-18 adopts the Chromatorex product of Japanese Fuji Silysia Chemical company; MCI is a Mitsubishi chemical company product, and thin plate (TLC) ultraviolet detection wavelength is the ultraviolet lamp of 254nm and 365nm; Developer iodine vapor, 10% sulfuric acid-ethanol, 2% iron trichloride-methyl alcohol, phospho-molybdic acid and tetrabromo-mcresolsulfonphthalein solution.
Liquid phase: Waters series of high efficiency liquid chromatograph comprises 2695 separation systems (quaternary pump, column oven and automatic sampler), 2996 ultraviolet diode matrix detectors, Empower chromatographic run software.Chromatographic column: WatersSymmetry
RP18 (3.9 * 150mm, 5 μ m).
1.2 plant origin and evaluation
Purchase in the Haozhou, Anhui August calendar year 2001 with the taraxacum medicinal material for extracting, be accredited as the herb of Mongolian taraxacum (Taraxacum mongolicum Hand.-Mazz.) by associate professor Chen Liurong of pharmaceutical college of Zhejiang University.Use taraxacum (Mongolian taraxacum) (Taraxacum mongolicum Hand.-Mazz) for comparing content, alkali ground taraxacum (magnificent taraxacum) (Taraxacum sinicum Kitag), hot river taraxacum (white edge taraxacum) (TaraxacumplatypecidumDiels), Herba Taraxaci ohwiani (Taraxacum ohwianumKitag), anti-luxuriant taraxacum (Taraxacum grypodon Dahlst), each 20 gram of Xingan taraxacum (Taraxacum falcilobum Kitag) dry product are taught in August, 2003～2004 by the Peng Hua of Kunming plant institute of the Chinese Academy of Sciences and are assisted to gather and identify year July., identify than gathering from the Tian Mu Shan Mountain, Zhejiang Province for fresh and dried product content by associate professor Chen Liurong of pharmaceutical college of Zhejiang University than taraxacum (Mongolian taraxacum) (Taraxacum mongoliumHand.-Mazz) and each 100 gram of the bright product of alkali ground taraxacum (magnificent taraxacum) (Taraxacum sinicum Kitag).
1.3 extract and separate
Sample shines dry grinding (5.0 kilograms of dry weights) back and carries twice with heat under the 75% industrial spirit boiling water, and extracting solution cooling back merges, and gets the thick crude extract of 462 gram browns through concentrating under reduced pressure.With the crude extract dissolve with methanol, D-101 macropore resin is mixed sample, methyl alcohol is removed in decompression on Rotary Evaporators, with the discolour silica gel is siccative, 40 ℃ of vacuum-dryings are spent the night, and application of sample is collected 50% methanol-water wash-out position in the good D-101 post of water balance, elutriant is concentrated into dried, makes behind the suspension with distilled water again and distribute extraction with sherwood oil, ethyl acetate, propyl carbinol successively.Get 3 grams after each organic layer evaporated under reduced pressure respectively, 32 grams, 127 gram medicinal extract, surplus is the water position.
1.4 the separation and purification at water position
Water intaking position medicinal extract 50 gram reverse phase silica gel (RP-18) posts (100 gram), with water-methanol (1: 0 → 0: 1) is the eluent gradient elution, wherein 10% methanol-eluted fractions position (1.4 gram) uses dextrane gel Sephadex LH-20 (100 milliliters) column chromatography, with water-methanol (1: 0 → 0: 1) wash-out, obtain Mongolian taraxacum glycosides A (11.0 milligrams) through recrystallization, 50% methanol-eluted fractions position (500 milligrams) is after dextrane gel Sephadex LH-20 post, use methanol-eluted fractions, through the thin-layer chromatography inspection, contain same composition person and merge, and obtain Mongolian taraxacum glycosides B (16.1 milligrams) through water-pure recrystallization.
1.5 structure is identified
The structure of Mongolia taraxacum glycosides A is identified: Mongolian taraxacum glycosides A is a yellow powder shape solid, is slightly soluble in methyl alcohol, and is soluble in water.Under the 254nm uv-absorbing is arranged, with 10% sulfuric acid-ethanolic soln reaction displaing yellow, hydrochloric acid-magnesium powder reacting positive, not Li Shi (Molish) reacting positive; UV spectrum: λ max 259,357nm.Above feature can judge tentatively that this compound may be flavonoid glycoside compound.Mongolia taraxacum glycosides A it
1H-NMR and
13The low place signal of C-NMR and Compound I soetine closely similar [B Voirin etc., Isoetine, a new flavoneisolated from Isoetes delilei and Isoetes durieui, Phytochemistry, 1975,14,257-259; K Gluchoff-Fiasson etc., Glycosides and acylated glycosides ofisoetin from European species of Hypochoeris, Phytochemistry, 1991,30,1673-1675], high field region is typical sugared fignal center, can judge that according to above information Mongolian taraxacum glycosides A is the glycosides derivative of Compound I soetine.δ 5.08 in the hydrogen spectrum (1H, bimodal, J=8.0Hz) and δ 4.87 (1H, bimodal, two hydrogen J=6.0Hz) are typical flavonoid glycoside sugar anomeric proton, have 11 protons in high field region δ 3.2-3.6 scope, and from
13The High-Field of C-NMR spectrum partly has 9 carbon to concentrate in the scope of δ 60-78, therefore can judge that this flavonoid glycoside is a disaccharide oxygen glycosides.
13The low place δ 163.1 (s) of C-NMR spectrum, 161.8 (s), 161.4 (s), 157.3 (s), 150.4 (s), 150.4 (s), 140.6 (s) are 7 company's oxygen fragrance quaternary carbons among the Mongolian taraxacum glycosides A.Wherein δ 182.4 (s) is 5 carbonyl signals, and the carbon spectrum signature of above signal and flavonoid glycoside matches.Low place δ 7.31 (1H, s) and 6.77 (1H, one group of unimodal fignal center s) shows on the compd B ring have 1,2,4,5-four replaces.δ 6.44 (1H, s) and δ 6.72 (1Hs) show have on the A ring two be between the position proton, (1H s) encircles last 3 proton signals for C to δ 7.16.Above chromatogram characteristic shows that the Flavone aglycone of Mongolian taraxacum glycosides A partly is Compound I soetine.Will
13The δ value of sugar charcoal contrasts with the standard spectrogram and the document of sugar in the C-NMR spectrum, find consistent with the carbon signal of glucose and pectinose respectively [the K R Markham etc. of carbon signal of these two sugar, Luteolin 7-O-[6-O-α-L-arabiofuranosyl] β-D-glucopyranoside and other new flavonoid glycosidesfrom New Zealand Dacrydium species, Journal of Natural Products, 1987,50,660-663].And in thin layer acid hydrolysis experiment, by with standard control, the aglycon that confirms Mongolian taraxacum glycosides A is Compound I soetine, two monose are respectively glucose and pectinose.
13In the C-NMR spectrum, δ 163.1,150.4 be respectively the signal of aglycon 7 and 2 ' carbon, this signal is respectively to high field displacement, and above information judges that tentatively 7 of aglycons and 2 ' are combined into glycosides [J B Harborne, Revised structures for threeisoetin glycosides with sugar, yellow flower pigments in Heywoodiella oligocephala.Phytochemistry, 1991,30,1677-1688].
In the UV spectrum of Mongolia taraxacum glycosides A methanol solution, band I maximum absorption wavelength λ max is 357nm; Add diagnostic reagent aluminum chloride (AlCl
3) behind the solution, band I red shift is to maximum absorption wavelength λ max 425nm; And after adding a spot of hydrochloric acid again, band I violet shift is to the long λ max of maximum absorption wave skin 394nm, therefore can determine to exist in the A ring of Mongolian taraxacum glycosides A 5-OH and B to have the adjacent phenolic hydroxyl group, i.e. 7 and 2 ' hydroxyl glycosylation in encircling.
After tentatively having determined the structure type of Mongolian taraxacum glycosides A, further determine the substituent link position of name by two dimensional NMR spectroscopic technique 2D-NMR.
1H-
1In the H COSY test-results, δ 6.72 (s) and δ 6.44 (s) have correlation effect, prove that further the A ring of Mongolian taraxacum glycosides A is 5, and 7-two replaces; And δ 5.08 (1H, bimodal J=8.0Hz) and δ 4.87 (1H, bimodal J=6.0Hz) have relevant these two signals that further proved to be sugar upper end matrix subsignal with saccharic.
Utilize HMBC and HSQC technology, at first (1H, s) (1H, two proton signals s) set out, to having carried out accurate ownership with proton and carbon on the flavones parent nucleus with δ 6.77 from δ 7.31.Then according to δ 5.08 (1H in the HMBC spectrum, bimodal J=8.0Hz, the proton of H-1 ") and δ 163.1 (s; C-7); 77.3 (d; C-5 ") and 76.6 (d, C-3 ") has correlation effect, the proton of δ 4.87 (1H, bimodal J=6.0Hz) and δ 150.4 (s; C-2 '); 70.7 (d, C-3 ) and 65.4 (t, C-5 ) have correlation effect; determine that two glycan molecules are connected on the C-7 and C-2 ' of isoetine in the mode of oxygen glycosidic bond, and the glycosyl that connects of C-7 position is a glucose and C-2 ' position is pectinose.Consider that it is Isoetine-7-oxygen-β-glucopyranose base-2 '-oxygen-α-pyranose form Arabinoside that the structure of Mongolian taraxacum glycosides A is accredited as Isoetine-7-O-β-g1ucopyranosyl-2 '-O-α-abinopyranoside in sum and according to biosynthesizing.
(arrow is depicted as the HMBC spectrogram of Mongolian taraxacum glycosides A)
Mongolia taraxacum glycosides A: yellow unformed powder: C
26H
28O
16Fusing point: 232-233 ℃: uv-absorbing UV λ max nm:258,357 (methyl alcohol); 272,326,425 (aluminum chlorides); 268,318,394 (aluminum chloride+hydrochloric acid); Electrospray ionization mass spectrum ESI-MS m/z:597[M+H]
+The hydrogen spectrum
1H-NMR (DMSO-d
6, 400MHz) δ 13.11 (1H, wide unimodal, 5-OH), 7.31 (1H, unimodal H-6 '), 7.16 (1H, unimodal, H-3), 6.77 (1H, unimodal H-3 '), 6.72 (1H, unimodal, H-8), 6.44 (1H ' unimodal, H-6), 5.08 (1H, bimodal, J=8.0Hz, H-1 "); 4.87 (1H, bimodal, J=6.0Hz, H-1 ), 3.20-3.60 (6H; multiplet, H-2 "～H-6 "), 3.20-3.60 (5H, multiplet, H-2 ～H-5 ); The carbon spectrum
13C-NMR (DMSO-d
6, 100MHz) δ 182.4 (s, C-4), 163.1 (s, C-7), 161.8 (s, C-2), 161.4 (s, C-5), 157.9 (s, C-9), 150.4 (s, C-4 '), 150.4 (s, C-2 '), 140.6 (s, C-5 '), 114.8 (d, C-6 '), 110.6 (s, C-1 '), 108.9 (d, C-3), 105.4 (d, C-10), 104.4 (s, C-3 '), 101.8 (d, C-l ), 100.0 (d, C-1 "), 99.5 (d, C-6); 94.7 (d, C-8), 77.3 (d, C-5 "), 76.6 (d, C-3 "), 73.3 (d, C-2 "), 72.5 (d, C-2 ), (70.7 d, C-3 ), 69.7 (d, C-4 "), 67.3 (d; C-4 ), 65.4 (t, C-5 ), 60.8 (t, C-6 ").
The structure of Mongolia taraxacum glycosides B is identified: Mongolian taraxacum glycosides B is a yellow powder powder solid, with 10% sulfuric acid-ethanolic soln reaction displaing yellow, hydrochloric acid-magnesium powder reacting positive, spray aluminum chloride ethanol liquid displaing yellow fluorescence, Li Shi (Molish) reaction is not positive, UV spectrum UV: maximum absorption wavelength λ max 259,357nm.Above information all points out Mongolian taraxacum glycosides B also to be flavonoid glycoside compound.Proton nmr spectra
1In the H-NMR spectrum, δ 6.73 (1H, unimodal, H-6) and δ 6.45 (1H, unimodal, fignal center explanation A ring H-8) is 5,7-two replaces; δ 7.11 (1H, unimodal, H-3) illustrate that this compound is flavonoid glycoside but not flavonol glycosides compounds; The fignal center of δ 7.31 (1H, unimodal, H-6 ') and δ 6.80 (1H, unimodal, H-3 ') shows that the B ring is 1,2,4, and 5-four replaces.Above information and Compound I soetine very with, simultaneously similar to the Flavone aglycone part of Mongolian taraxacum glycosides A.In addition, proton nmr spectra
1δ 5.08 in the H-NMR spectrum (1H, bimodal, J=8.0Hz, the fignal center of H-1 ") and δ 4.91 (1H, wide unimodal, H-1 ) illustrates and has two glycosyls in this compound; thin-layer chromatography TLC acid hydrolysis only detects glucose, can illustrate that two glycosyls are glucose in the compound.Therefore can release compound Mongolia taraxacum glycosides B is the dioxy glucoside of isoetine.Coupling constant by terminal hydrogen and with document contrast [Santoflavone such as V U Ahmad, a 5-deoxylflavonoid from Achillea santalina.Phytochemistry, 1995,38,1305-1309], determine that one is β-glucose in two glucose, another is a α-Pu Taotang.
The carbon-13 nmr spectra of comparative compound Mongolia taraxacum glycosides B and compound Mongolia taraxacum glycosides A
13C-NMR spectrum data (table 1) can be found: the Flavone aglycone fignal center of the low place of two compounds overlaps substantially, has only sugared position to have any different slightly.Similarly be δ 163.0,150.4 be respectively the signal of aglycon 7 and 2 ' carbon, this signal is also respectively to high field displacement, and also prove conclusively the structural unit that has adjacent two phenolic hydroxyl groups on the B ring of Mongolian taraxacum glycosides B by adding diagnostic reagent, therefore pointing out compound Mongolia taraxacum glycosides B also is that 7 and 2 ' and sugar are combined into glycosides.The High-Field part of comparative compound Mongolia taraxacum glycosides B and compound Mongolia taraxacum glycosides A, the sugared signaling zone of compound Mongolia taraxacum glycosides A is a glucose and a pectinose, and compound Mongolia taraxacum glycosides B is bimolecular glucose, reject the fignal center of 7 β-glucosyl groups remaining be 2 ' alpha-glucose-based fignal center.
Therefore, the structure of determining compound Mongolia taraxacum glycosides B is Isoetine-7-O-β-glucopyranosyl-4 '-O-α-glucopyranoside.
Mongolia taraxacum glycosides B: yellow unformed powder; C
27H
30O
17Fusing point: 223-224 ℃; Uv-absorbing UV λ max nm:257,356 (methyl alcohol); 270,326,426 (aluminum chlorides; 267,319,393 (aluminum chloride+hydrochloric acid); Electrospray ionization mass spectrum ESI-MSm/z:627[M+H]
+The hydrogen spectrum
1H-NMR (DMSO-d
6, 400MHz) δ 13.07 (1H, unimodal, 5-OH), 7.31 (1H, unimodal, H-6 '), 7.11 (1H, unimodal, H-3), 6.80 (1H, unimodal, H-3 '), 6.73 (1H, unimodal, H-8), 6.45 (1H, unimodal, H-6), 5.08 (1H, bimodal, J=8.0Hz, H-1 "), 4.91 (1H, wide unimodal, H-1 ), 3.20-3.60 (6H; multiplet, H-2 "～H-6 "), 3.20-3.60 (6H, multiplet, H-2 ～H-6 ); The carbon spectrum
13C-NMR (DMSO-d
6, 100MHz) 6 182.2 (s, C-4), 163.0 (s, C-7), 161.8 (s, C-2), 161.3 (s, C-5), 157.2 (s, C-9), 150.4 (s, C-4 '), 150.4 (s, C-2 '), (140.5 s, C-5 '), 114.7 (d, C-6 '), 110.4 (s, C-1 '), 108.9 (d, C-3), 105.4 (d, C-10), (104.7 s, C-3 '), 101.3 (d, C-1 ), 100.1 (d, C-1 "), 99.5 (d, C-6), 94.7 (d, C-8); 77.3 (d, C-5 "), 77.3 (d, C-5 ), (76.9 d, C-3 ), 76.5 (d, C-3 "); 73.5 (d, C-2 ), 73.3 (d, C-2 "), (69.7 d, C-4 ), 69.7 (d, C-4 "); 60.8 (t, C-6 ), 60.8 (t, C-6 ").
The Mongolian taraxacum glycosides of table 1 A (compound 1) and Mongolian taraxacum glycosides B's (compound 2)
1H-NMR and
13The C-NMR data relatively
a
| No. | 1 | 2 | ||
| δ C | δ H | δ C | δ H | |
| 2 3 4 5 6 7 8 9 10 1’ 2’ 3’ 4’ 5’ 6’ 1″ 2″ 3″ 4″ 5″ 6″ 1 2 3 4 5 6 | 161.8 108.9 182.4 161.4 99.5 163.1 94.7 157.9 105.4 110.6 150.4 104.4 150.4 140.6 114.8 100.0 73.3 76.6 69.7 77.3 60.8 101.8 72.5 70.7 67.3 65.4 | 7.16 (1H，s) 6.44(1H，s) 6.72(1H，s) 6.77(1H，s) 7.31(1H，s) 5.08(1H，d，J＝ 8.0Hz) 3.20-3.60(6H， m) 4.87(1H，d，J＝ 6.0Hz) 3.20-3.60(5H， m) | 161.8 108.9 182.2 161.3 99.5 163.0 94.7 157.2 105.4 110.4 150.4 104.7 150.4 140.5 114.7 100.1 73.3 76.5 69.7 77.3 60.8 101.3 73.5 76.9 69.7 77.3 60.8 | 7.11(1H，s) 6.45(1H，s) 6.73(1H，s) 6.80(1H，s) 7.31(1H，s) 5.08(1H，d，J＝8.0 Hz) 3.20-3.60 (6H，m) 4.91(1H，brs) 3.20-3.60 (6H，m) |
aThe hydrogen spectrum
1H NMR (400MHz), the carbon spectrum
13CNMR and DEPT (100MHz) is at DMSO-d
6Middle mensuration. coupling constant is represented with hertz.
Embodiment 2:Flavonoid glycoside compound 1 and 2 suppresses the gram-positive bacteria ability and detects
2.1 principle:
Adopt the antibacterial activity in vitro of " cup-plate method " research trial medicine, be to utilize the trial drug that is added in the cup of Oxford to be diffused into inoculation to have in the substratum of test organisms, thereby suppress the growth of bacterium, come the anti-microbial activity of confirmed test medicine by the diameter that detects the inhibition zone that around the cup of Oxford, forms.
2.2 detect bacterium:
Streptococcus aureus 26003-23 is available from Nat'l Pharmaceutical ﹠ Biological Products Control Institute.
Beta hemolytic streptococcus 32210 is available from Nat'l Pharmaceutical ﹠ Biological Products Control Institute.
2.3 trial drug:
The DMSO:DMSO solvent control;
Norfloxicin: 1.25mg/ml;
The Mongolia sweet A of taraxacum (compound 1): 5.0mg/ml; Mongolia taraxacum glycosides B (compound 2): 5.0mg/ml;
Sample all dissolves with DMSO.
2.4 method and step:
2.4.1, the preparation of M-H agar, M-H meat soup and examination eyelid bacterium liquid.
2.4.2, the preparation of two dish:
(1), M-H agar bottom: get sterilization M-H agar liquid naturally cooling and solidify.
(2), M-H agar bacterium layer: get gu μ l at nights 150 and 30mlM-H agar mixing.Get about 5ml and contain bacterium liquid agar, evenly spread out cloth in plate with M-H agar bottom.
2.4.3, treat culture medium solidifying after, in each plate, evenly put the upright test soup Oxford cup of filling it up with.
2.4.4, put 37 ℃ and cultivated 24 hours.
2.4.5, use the vernier caliper measurement antibacterial circle diameter.
Sweet A of the Mongolian taraxacum of table 2 (compound 1) and Mongolian taraxacum glycosides B (compound 2)
Antibacterial circle diameter (mm) to the standard pathogenic bacterium
| Bacterial classification | The experiment medicine | |||
| DMSO | 1 (50mg/ml) | Norfloxicin (2.5mg/ml) | 2 (50mg/ml) | |
| Streptococcus aureus-26003 beta hemolytic streptococcus-10102 | Unrestraint 9.18 | 10.15 19.13 | 30.26 27.82 | 12.63 16.45 |
2.5 experiment conclusion:
By adopting the antibacterial activity in vitro of " micro-dilution method " the research compound 1 and the 2 pairs of golden yellow staphylococcus and beta hemolytic streptococcus.The result shows: the compound 1 and the 2 pairs of streptococcus aureuses and beta hemolytic streptococcus have better antibacterial activity.Illustrate that it is that potential suppresses the gram-positive bacteria active substance, has further exploitation and is worth.
Novel flavonoid glycoside of the present invention (Mongolian taraxacum glycosides A and Mongolian taraxacum glycosides B) can combine with spoke material or carrier pharmaceutically commonly used, prepares the medicine and pharmaceutical composition or the healthcare products that have prevention and treat the infection that is caused by streptococcus aureus and beta hemolytic streptococcus.Above-mentioned various kinds of drug composition or healthcare products can adopt tablet, capsule, injection to squeeze drug forms such as agent, aerosol, suppository, film, pill, externally-applied liniment, ointment.
Novel flavonoid glycoside Mongolia taraxacum glycosides A of the present invention and Mongolian taraxacum glycosides B can also infect the medicine of associated conditions and bulk drug thereof such as cephalosporin, Macrolide and sulfamido such as husky magnitude types of drugs with the similar gram-positive bacteria of the streptococcus aureus that has now gone on the market, beta hemolytic streptococcus inhibitor and/or other treatment and unite use, prepare and have the treatment gram-positive bacteria and infect the composition or the compound preparation of associated conditions effect, can expect becomes treatment gram-positive bacteria catch medicine or healthcare products.Above-mentioned various kinds of drug composition or healthcare products can adopt drug forms such as tablet, capsule, injection, aerosol, suppository, film, pill, comprise the conventional preparation of pharmaceutics general knowledge that employing has now been generally acknowledged and various slowly-releasings, controlled release form or the nanometer formulation that gets.
Embodiment 3:Compound 1 and 2 comparison in five kinds of Dandelion plant roots and stems and the over-ground part cauline leaf
Taraxacum (Mongolian taraxacum) (TaraxacummongolicumHand-Mazz), alkali ground taraxacum (magnificent taraxacum) (Taraxacum sinicum Kitag), hot river taraxacum (white edge taraxacum) (Taraxacumplatypecidum Diels), Herba Taraxaci ohwiani (Taraxacum ohwianum Kitag), anti-luxuriant taraxacum (Taraxacum grypodon Dahlst), each 20 gram of Xingan taraxacum (Taraxacum falcilobum Kitag) dry product are gathered by professor Peng Hua of Kunming plant institute of the Chinese Academy of Sciences and are identified.
With this high performance liquid chromatography of water (Waters HPLC, 2695 separation systems comprise quaternary pump, column oven automatic sampler; 2996 ultraviolet diode matrix detectors, Empower chromatographic run software and Waters Symmetry
RP-18 4.6mm * 250mm, 5 μ m chromatography columns) compound 1 and 2 has been carried out content detection.
Handle for test agent: the sample that dries in the shade after pulverizing respectively takes by weighing 0.5 gram (± 0.1 milligram), puts 25 milliliters of volumetric flasks, adds 20 ml methanol, 25～30 ℃ ultrasonic 60 minutes down, add methyl alcohol to scale, filter with 0.45 μ m filter membrane.
The preparation of standardized solution: prepare to take by weighing respectively 10.0 milligrams of compounds 1 and 2, add 8 ml methanol ultrasonic dissolutions respectively, add the standard reserving solution that methyl alcohol is made into 0.5 mg/ml more separately., 1: 10,1: 50, be mixed with standardized solution, refrigerate standby at 1: 100 according to 1: 1 with methyl alcohol.Prepare the standardized solution of compound 1 and 2 separately with method.Reagent: methyl alcohol is HPLC level (Merk production), and water is redistilled water.Chromatographic condition: use RP-C18 chromatographic column (4.6mm * 250mm), 5 μ m, 30 ℃ of column temperatures detect wavelength: 254nm, flow velocity: 0.8 ml/min, sample size: 20 μ l.Shown in the moving phase table composed as follows:
Table 3 is measured the high-efficient liquid phase chromatogram condition of Mongolian taraxacum glycosides A and Mongolian taraxacum glycosides B
| Time (minute) | Methyl alcohol (%) | 0.1% acetic acid (%) |
| 0 | 22 | 78 |
| 30 | 22 | 78 |
| 31 | 35 | 65 |
| 55 | 35 | 65 |
| 56 | 40 | 60 |
| 80 | 40 | 60 |
Content measuring: with extraction solvent, standard solution, confession test agent difference sample introduction, record color atlas.With the corresponding concentration of standard solution curve plotting of peak area, calculate linearity range, relation conefficient 〉=0.998.Calculate the content of compound 1 and 2 respectively from typical curve.
Discovery content is as shown in the table:
The content of Mongolian taraxacum glycosides A (compound 1) and Mongolian taraxacum glycosides B (compound 2) in the common taraxacum of table 4
| Compound 1 content (%) | Compound 2 content (%) | |
| Mongolia's taraxacum (taraxacum) rhizome part | 0.56 | 0.58 |
| Mongolia's taraxacum (taraxacum) over-ground part cauline leaf | 0.53 | 0.59 |
| Alkali ground taraxacum (magnificent taraxacum) herb | 0.43 | 0.35 |
| Hot river taraxacum (white edge taraxacum) herb | 0.73 | 0.55 |
| The Herba Taraxaci ohwiani herb | 0.61 | 0.67 |
| Anti-luxuriant taraxacum herb | 0.29 | 0.86 |
| Xingan's taraxacum herb | 0.62 | 0.93 |
The result shows: Mongolian taraxacum rhizome and over-ground part all contain compound of the present invention, and alkali ground taraxacum, hot river taraxacum, Herba Taraxaci ohwiani, anti-luxuriant taraxacum, the compound 1 and 2 that all contains different content in the Xingan taraxacum, illustrate that Mongolian taraxacum glycosides A and Mongolian taraxacum glycosides B are the characteristic chemical constituents in the composite family Dandelion plant, are not limited to Mongolian taraxacum so use this platymiscium to comprise, alkali ground taraxacum, hot river taraxacum, Herba Taraxaci ohwiani, anti-luxuriant taraxacum, Xingan taraxacum etc. can prepare the anti-gram-positive bacteria medicine that contains Mongolian taraxacum glycosides A and Mongolian taraxacum glycosides B of the presently claimed invention.
Embodiment 4:Two kinds of Dandelion plant stem-leafs (in bright product and the dry product) compound 1 and 2 comparison
Taraxacum (Mongolian taraxacum) (TaraxacummongolicumHand-Mazz), the bright product of alkali ground taraxacum (magnificent taraxacum) (Taraxacum sinicum Kitag) each 100 restrain and identify by professor Chen Liurong of Zhejiang University.
With this high performance liquid chromatography of water (Waters HPLC, 2695 separation systems comprise quaternary pump, column oven automatic sampler; 2996 ultraviolet diode matrix detectors, Empower chromatographic run software and Waters Symmetry
RP-18 4.6mm * 250mm, 5 μ m chromatography columns) compound 1 and 2 has been carried out content detection.
Content measuring: with extraction solvent, standard solution, confession test agent difference sample introduction, record color atlas.With the corresponding concentration of standard solution curve plotting of peak area, calculate linearity range, relation conefficient 〉=0.998.Calculate the content of compound 1 and 2 respectively from typical curve.Concrete operations are with embodiment 3.
Mongolian taraxacum glycosides A and the contrast of Mongolian taraxacum glycosides B content in two kinds of taraxacum dry products of table 5 and the bright product
| Compound 1 content (%) | Compound 2 content (%) | |
| The bright product of Mongolia taraxacum (taraxacum) | 0.57 | 0.61 |
| Mongolia's taraxacum (taraxacum) dry product | 0.53 | 0.59 |
| The bright product of alkali ground taraxacum (magnificent taraxacum) | 0.47 | 0.43 |
| Alkali ground taraxacum (magnificent taraxacum) dry product | 0.49 | 0.41 |
The result shows: all contain the compound 1 and 2 of different content in dry product of Mongolian taraxacum and alkali ground taraxacum and the bright product, content there is no too big difference.Illustrate that Mongolian taraxacum glycosides A and Mongolian taraxacum glycosides B exist and content is comparatively stable in composite family Dandelion plant, so use dry product of this platymiscium and bright product can prepare the anti-gram-positive bacteria medicine that contains Mongolian taraxacum glycosides A and Mongolian taraxacum glycosides B of the presently claimed invention.
Claims (8)
1. the flavonoid glycoside and pharmacologically acceptable salt or its solvate that have following structure:
Compound 1 (Mongolian taraxacum glycosides A)
Compound 2 (Mongolian taraxacum glycosides B).
2. the described compound of claim 1, its title is respectively:
Compound 1 (Mongolian taraxacum glycosides A): Isoetin-7-oxygen-β-glucopyranose-2 '-oxygen-α-pyranose form Arabinoside;
Compound 2 (Mongolian taraxacum glycosides B): Isoetin-7-β-glucopyranose base-4 '-oxygen-α-glucopyranoside.
3. according to the preparation approach of claim 1 or 2 described compounds, it is mainly derived from the arbitrary position of home-made Dandelion plant in any one, promptly can be taraxacum (claiming Mongolian taraxacum again) (Taraxacummongolicum Hand-Mazz), alkali ground taraxacum (claiming magnificent taraxacum again) (Taraxacum sinicumKitag), hot river taraxacum (claiming white edge public English again) (Taraxacum platypecidumDiels), Herba Taraxaci ohwiani (Taraxacum ohwianumKitag), anti-luxuriant taraxacum (Taraxacum grypodonDahlst), common taraxacum medicinal material on Xingan taraxacum (Taraxacum falcilobumKitag) and other the Chinese drug markets; Can be dry product or bright product; Can be root, stem, leaf, flower, seed, skin, the fruit of taraxacum medicinal material plant, also can be their mixture and herb part.
4. according to claim 1 or 2 described flavonoid glycoside compounds, it is used to prepare prevention or treats streptococcus aureus and/or the purposes of the medicine of the related symptoms of beta hemolytic streptococcus infection or disease.
5. according to the purposes of claim 4, wherein the related symptoms of infection of staphylococcus aureus or disease are meant furuncle, warts, toxicity epidermis decomposition, pneumonia, osteomyelitis, acute myocarditis, mazoitis, urocystitis, prostatitis, microbemia, toxic shock syndrome, poradenolymphitis, pharyngitis, trachelitis, pelvic inflammatory disease, and the abscess of muscle, skin, urodeum, central nervous system; Related inflammation was meant skin, respiratory tract and soft tissue infection such as pneumonia, microbemia, endocarditis, meningitis, urinary tract inflammation and arthritis disease due to beta hemolytic streptococcus infected.
6. one kind is used to prevent or treat streptococcus aureus and/or the related symptoms of beta hemolytic streptococcus infection or the pharmaceutical composition of disease, it contains as the claim 1 of the treatment significant quantity of activeconstituents or 2 described flavonoid glycoside compounds or their pharmacologically acceptable salt, with and composition thereof and pharmaceutically acceptable carrier.
7. according to the pharmaceutical composition of claim 6, it is that prevention and treatment streptococcus aureus and/or beta hemolytic streptococcus infect furuncle, warts, toxicity epidermis decomposition, pneumonia, osteomyelitis, acute myocarditis, endocarditis, meningitis, mazoitis, urocystitis, pelvic inflammatory disease, urinary tract inflammation, prostatitis, microbemia, toxic shock syndrome, poradenolymphitis, sacroiliitis, pharyngitis, the trachelitis that causes, and the abscess of muscle, skin, urodeum, central nervous system.
8. according to the pharmaceutical composition of claim 6 or 7, it can be tablet, particle profit, capsule, oral liquid, lotion, suppository, liniment, injection, transdermal patch or aerosol, can also adopt the known controlled release of modern pharmaceutical circle or slow release formulation or nanometer formulation.
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Owner name: DALI PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: ZHAO YU Effective date: 20120224 |
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Free format text: CORRECT: ADDRESS; FROM: 310012 HANGZHOU, ZHEJIANG PROVINCE TO: 671000 DALI BAI AUTONOMOUS PREFECTURE, YUNNAN PROVINCE |
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Effective date of registration: 20120224 Address after: 671000, No. 118, West Ring Road, Shimonoseki, Dali Bai Autonomous Prefecture, Yunnan, Dali Patentee after: Dali Pharmaceutical Co., Ltd. Address before: Hangzhou City, Zhejiang province Xihu District 310012 North Building 9, unit 5, Jia Garden Room 201 Patentee before: Zhao Yu |