CN100491393C - Steroid saponins and preparation method and application - Google Patents
Steroid saponins and preparation method and application Download PDFInfo
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- CN100491393C CN100491393C CNB2006100650433A CN200610065043A CN100491393C CN 100491393 C CN100491393 C CN 100491393C CN B2006100650433 A CNB2006100650433 A CN B2006100650433A CN 200610065043 A CN200610065043 A CN 200610065043A CN 100491393 C CN100491393 C CN 100491393C
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Abstract
The invention relates to a new saponin compound with a structure represented by right formula, wherein, R1 is glycosyl of 1-12; R2 is H or OH or O-angelicaacyl; R3 is OH or O-glucose; R4 is H or angelicaacyl or acetyl; R5 is OH or O-acetyl; and the producing method of said compound, and the application in the anti-inflammation and bacteriostasis areas.
Description
Technical field
The present invention relates to a kind of saponins compound, especially a kind of new saponins compound with formula I structure, and in the application for the treatment of aspects such as inflammation, infectation of bacteria.
Background technology
Ocimum basilicum L. is the dry aerial parts of Primulaceae Lysimachia plant Lysimachia foenum-graecum Lysimachia foenum-graecum Hance, main product in Guangxi, ground such as Guangdong, Sichuan, Yunnan, Guizhou.Its beginning is stated from supplementary Amplifications of the Compendium of Materia Medica, and " Bencao Tujing " is called illiteracy state Ocimum basilicum L., and " An Illustrated Book on Plants " is called Lysimachia sikokiana, and Ocimum basilicum L. is recorded for " Guangxi Chinese medicinal materials standard " at present, has another name called vanilla, a species of orchid grass, wide Ocimum basilicum L., smoked careless.The Ocimum basilicum L. flavor is hot, sweet, and property is flat, and is nontoxic; Return lung, the stomach warp; Have and induce sweat, pain relieving, the effect of ascarid is driven in promoting the circulation of qi, and folk tradition is mainly treated cold headache, swelling and pain in the throat, toothache, distension and fullness of the chest and abdomen, ascariasis etc.
Aspect medicinal, Ocimum basilicum L. and other multiple medicines carry out compatibility, as have drive away summer heat keep away dirty, the medicinal powder for preventing from seasonal febrile diseases of the pain relieving effect of having one's ideas straightened out, Ocimum basilicum L. is one of main component wherein, now records in one one of Pharmacopoeia of the People's Republic of China version in 2000; In addition, Ocimum basilicum L. is treated the vertigos that summer, summer-heat evil caused clinically, and the headache nasal obstruction is felt sick, and vomits, and carsickness is seasick etc.; Because of strong fragrance is arranged, Ocimum basilicum L. is widely used at foodstuffs industry, tobacco industry as spices again simultaneously.
Chemical ingredients and the research of pharmacological action aspect to Ocimum basilicum L. at present mainly concentrates on following aspect:
Chemical constitution study: containing volatile oil in the herb, mainly is ester class, organic acid, alkane etc. in the oil; Nonacosane, hentriacontane, Stigmasterol, Stigmasterol-3-O-β-D-glucoside and bessisterol have been got in the ether extract.
Pharmacology and toxicological study: the pharmacological evaluation proof has the effect of the influenza virus of inhibition; Toxicology and antifertility research, experiment shows that Ocimum basilicum L. is safety low-poison Chinese medicine, not overslaugh Fertility does not have teratogenesis yet.
Because Ocimum basilicum L. is a kind of medicinal and spice berry with higher economic worth, and modern less to its research, so concrete pharmaceutical use, medicinal part and the activeconstituents thereof of relevant Ocimum basilicum L. await further going deep into development research.
Summary of the invention
The inventor gropes through a large amount of experiments, and in conjunction with modern advanced extraction process, extraction separation has gone out a kind of new saponins compound from Ocimum basilicum L. Chinese medicine, experiment showed, that this compounds has tangible anti-inflammatory, bacteriostatic action.
The object of the present invention is to provide a kind of new saponins compound, this compounds has significantly antibacterial, anti-inflammatory action.
The present invention also aims to provide a kind of method of extracting the above-mentioned saponins compound of preparation.
The present invention also aims to provide a kind of pharmaceutical composition that contains above-mentioned saponins compound, antibacterial, antiphlogistic effect that said composition has.
The present invention also aims to provide the purposes of above-mentioned saponins compound aspect antibacterial, anti-inflammatory.
The invention provides a kind of saponins compound, this compound has as shown in the formula the structure shown in the I:
R
1Be sugar, number is 1-12; R
2Be H or OH or 0-angeloyl groups; R
3Be OH or O-sugar (also claiming glucosides), for example O-glucose; R
4Be H or angeloyl groups or ethanoyl; R
5Be OH or O-ethanoyl.Above-mentioned angeloyl groups structural formula is
The structural formula of ethanoyl is
The R of above-claimed cpd
1Be oligosaccharides, preferably be polymerized that this monose is selected from the glucose or the pectinose of glucose, rhamnosyl, pectinose, ethanoyl replacement by 4-6 monose.
Described structure optimization is: work as R
iDuring for rhamnosyl, glucose, pectinose (preferably being (outward) rhamanopyranosyl (1 → 2)-(interior) glucosyl group (1 → 4)-[glucosyl group (1 → 2)]-pectinose base sequence from outside to inside), R
2Be OH or 0-angeloyl groups, R
3Be OH, R
4Be H or ethanoyl, R
5Be OH;
Work as R
1When the glucose that replaces for ethanoyl, pectinose (preferably be (outward) glucosyl group (1 → 4)-(interior) 6 '-ethanoyl-β-D-glucosyl group (1 → 6)-(interior) glucosyl group (1 → 4)-[β-D-glucosyl group (1 → 2)]-β-D-Arab glycosyl from outside to inside), R
2Be H, R
3Be OH, R
4Be angeloyl groups, R
5Be the O-ethanoyl;
Work as R
1For glucose, pectinose (preferably in the following order: in the time of β-D-glucosyl group (1 → 4)-β-D-glucose (1 → 6)-β-D-glucosyl group (1 → 4)-[β-D-glucosyl group (1 → 2)]-β-D-pectinose), R
2Be H, R
3Be O-sugar (for example β-D-glucose), R
4Be angeloyl groups, R
5Be the O-ethanoyl;
In embodiments of the present invention, described compound includes the structure of following formula II, III, IV, V and VI:
The extraction and separation method of above-claimed cpd of the present invention comprises the Ocimum basilicum L. plant with ethanol-extracted, non-polar organic solvent extraction, macroporous adsorbent resin refining and edulcoration and high performance liquid phase separating process.
Above-mentioned preparation method, wherein preferably include with ethanol heating and extract, extracting solution with sherwood oil, methylene dichloride be extracted to successively colourless after, concentrated medicinal extract R, with R medicinal extract with macroporous adsorptive resins on the water dissolution, near after colourless, elutriant is recycled to dried, obtains medicinal extract R1 with ethanol elution, medicinal extract R1 is gone up silicagel column, with the methylene chloride-methanol is the eluent gradient elution, merges identical elutriant, uses the methanol aqueous solution wash-out of high performance liquid chromatography with 10-50% again.
In a preferred embodiment of the invention, the preparation method comprises: the chopping of Ocimum basilicum L. medicinal material, and use ethanol (preferred 70% ethanol) heating to extract, ethanol extract is concentrated near doing, and gets ethanol extract, and the control relative density is about 1.2; Ethanol extract dilution, with sherwood oil, methylene dichloride be extracted to successively colourless after, its remainder is concentrated into dried, medicinal extract R, the about 5%-30% of the yield of medicinal extract R (being generally 15～20%); With R medicinal extract with macroporous resin column on the water dissolution, after using lower concentration (being no more than 30%) and higher concentration (30～70%) ethanol elution closely colourless respectively, above-mentioned elutriant is recycled to dried, obtains medicinal extract R1, and medicinal extract R1 is with respect to the about 5%-30% of the yield of medicinal extract R (being generally about 15%); Medicinal extract R1 is gone up silicagel column, (for example weight proportion 9:1～1:1) is an eluent to methylene chloride-methanol in varing proportions, gradient elution, retinue thin layer TLC detects, merge identical elutriant, composition changes the back and changes eluent, obtain 8 components of DL-DL8 successively according to time sequence, select DL, DL8 (promptly the first and the 8th) component high performance liquid chromatography, the C18 reverse-phase chromatographic column is the mixed solution wash-out of 10:90-50:50 with the methanol-water ratio, obtains the compound group of formula I structure of the present invention, this compound group comprises five kinds of compounds at least, and structural formula is respectively II, III, IV, V, VI.
The inventor is an effective constituent with described compound (five kinds are share or single using) also in above-mentioned test, the pharmaceutical composition that has prepared this compound that contains pharmacy effective dose, also contain the pharmacy pharmaceutic adjuvant acceptable in the said composition, the formulation of its Chinese traditional medicine can be oral dosage form, injection type or transdermal administration formulation, described formulation and the auxiliary material that is adopted thereof are this area general knowledge, do not repeat them here.
Through experiment confirm aforementioned pharmaceutical compositions have an anti-inflammatory bacteriostatic effect, so the present invention also provides the effect of this pharmaceutical composition in aspect treatment inflammation, infectation of bacteria.
The pharmacology pharmacodynamic experiment
One, Ocimum basilicum L. effective constituent bacteriostatic action research
1. experiment material
1.1 the animal Kunming mouse, Wistar rat, cleaning level, male and female half and half.Conformity certification SCXK-(army) 2002-001, above animal is all purchased the Experimental Animal Center in Military Medical Science Institute.
1.2 medicine
Embodiment 1 resulting formula II～VI compound (pharmacological datum of the present invention is only with formula II, formula III structural compounds illustration) faces with the preceding distilled water diluting of using, and is made into the suspension of desired concn, through 100 ℃ of 30min flowing steam sterilizations.
The tangerine oral liquid of cough-relieving, produce in Beijing TongrenTang Co., Ltd Tongrentang pharmaceutical factory, lot number 3260113.
Gentamicin, Nat'l Pharmaceutical ﹠ Biological Products Control Institute produces, lot number 0326-9713.
2. experimental technique and result
2.1 extracorporeal bacteria inhibitor test
2.1.1 6 bacterial classifications of bacterial classification, totally 30 strains, section provides by the PLA General Hospital microorganism
Streptococcus pneumoniae: clinical isolates 4 strains; ATCC 49,619 1 strains
Streptococcus aureus (golden Portugal): clinical isolates 4 strains; ATCC 25,923 1 strains
Staphylococcus epidermidis (table Portugal): clinical isolates 4 strains; ATCC 12,228 1 strains
Pseudomonas aeruginosa: clinical isolates 4 strains; ATCC 27,853 1 strains
Intestinal bacteria: clinical isolates 4 strains; ATCC 25,922 1 strains
Klebsiella Pneumoniae (lung gram): clinical isolates 4 strains, ATCC 13,883 1 strains
2.1.2 method: adopt agar dilution, this medicine (pH6.5, with preceding all through 100 ℃ of 30 minutes flowing steam sterilizations; ) carry out doubling dilution with stroke-physiological saline solution, add the nutrient agar mixing respectively, impouring plate (adding 10% sheep blood in the streptococcus pneumoniae plate), standby.
2.1.3 the result shows that there is the obvious suppression effect Compound I I and III his-and-hers watches Portugal, minimal inhibitory concentration is respectively 21.4ug/ml, and the minimal inhibitory concentration of streptococcus pneumoniae standard bacterium is respectively 21.4ug/ml.
The result sees table 3 for details.
The external bacteriostatic experiment result of table 3
2.2 bacteriostatic experiment in the body
By prerun, adopt the streptococcus aureus of mouse 90% mortality ratio to increase toadstool liquid concentration and staphylococcus epidermidis respectively and increase toadstool liquid concentration and test.
(annotate: streptococcus aureus, staphylococcus epidermidis are clinical separation strain, and section provides by the PLA General Hospital microorganism, and the court microbial room cultivates, and streptococcus aureus concentration is 1.8 * 10
6Cfu/ml, staphylococcus epidermidis concentration is 1.8 * 10
5Cfu/ml, with the preceding 1g dried yeast powder that in every 10ml bacterium liquid, adds, be increase toadstool liquid)
2.2.1 dead provide protection to lethality streptococcus aureus abdominal cavity infection mouse
Kunming mouse, male and female half and half, by be divided at random after the body weight layering negative control (give isometric(al) distilled water), positive control drug (the tangerine oral liquid 5.0ml/kg of cough-relieving, 10 times of people's clinical dosages), Compound I I and III respectively according to 5, two dosage groups of 10mg/kg.Each group gastric infusion or feedwater according to dosage for three days on end, after administration in the 4th day was fed water 1 hour, abdominal injection 1.8 * 10
6Cfu/ml streptococcus aureus yeast increases venom 0.2ml/20g body weight, observes death condition in the mouse 72 hours.Calculate mortality ratio, the result is added up through the X2 check.
The results are shown in Table 4.
The dead provide protection of table 4 pair lethality infection of staphylococcus aureus mouse
Annotate: with negative control ratio, X
2-check,
*P＜0.05,
*P＜0.01, P＜0.001
* *
By table 4 as seen, the infection of staphylococcus aureus mouse had significant protective effect.
2.2.2 dead provide protection to lethality staphylococcus epidermidis abdominal cavity infection mouse
Animal grouping administration is the same, and administration in the 4th day feedwater is after 1 hour, and abdominal injection staphylococcus epidermidis concentration is 1.8 * 10
5The cfu/ml yeast increases venom 0.2ml/20g body weight, observes death condition in the mouse 72 hours.Calculate mortality ratio, through X
2Check is added up the result.The results are shown in Table 5.
The dead provide protection of table 5 pair lethality staphylococcus epidermidis infecting mouse
Annotate: with negative control ratio, X
2-check,
*P＜0.05,
*P＜0.01
By table 5 as seen, epidermis staphylococcal infections mouse had significant protective effect.
Above-mentioned experiment shows: some common bacteria of respiratory tract are all had certain restraining effect.
Two, anti-inflammatory action research
1 experiment material
1.1 animal
SPF level ICR mouse, male, available from Beijing dimension tonneau China Experimental Animal Center, conformity certification SCXK (capital) 2002-0003.
1.2 reagent
The saponins compound of embodiment 1 resulting formula II, formula III structure faces with the preceding distilled water diluting of using, and is made into the suspension of desired concn, through 100 ℃ of 30min flowing steam sterilizations.
The Asprin enteric coated tablet, sun pharmaceutcal corporation, Ltd in Beijing produces, and lot number 20021102 is ground into fine powder during experiment, be mixed with certain density suspension with distilled water.
2. experimental technique and result
2.1 influence to acute exudative inflammation (dimethylbenzene induced mice ear swelling)
The ICR mouse, body weight 19-21g, divide equally 8 groups at random by body weight, it is the blank group, acetylsalicylic acid 0.2g/kg group, Compound I I, III is respectively 0.25,0.50,1.00g/kg group, every group 10, gastric infusion is 4 days continuously, irritating body of stomach long-pending is the 0.4ml/20g body weight, and the blank group is given the aquae destillata of equal volume, behind last administration 1h, 60 μ l dimethylbenzene evenly are applied to every mouse auris dextra two sides, behind the 40min dislocation of mouse cervical vertebra is put to death, take off left and right sides auricle with diameter 8mm scleral perforation device and weigh, obtain two ear weight differences, calculate the swelling rate, t check comparative group differences the results are shown in Table 6.
Swelling rate=[(auris dextra weight-left ear is heavy)/left ear is heavy] * 100%
The influence of table 6 p-Xylol induced mice ear swelling (X ± SD)
Annotate: compare with the blank group
*P＜0.05
*P＜0.01
The result shows: p-Xylol induced mice ear swelling has obvious restraining effect, shows that this medicine has the effect of obvious inhibition acute inflammation infiltration.
Simultaneously compound IV, V, VI are done same experiment, the drug effect of result and Compound I I, III is similar, present the effect of structure activity relationship, this compounds that shows the I of having structural formula of the present invention all has certain restraining effect to some common bacteria of respiratory tract, and p-Xylol induced mice exudative inflammation has the obvious suppression effect.
Embodiment
The present invention will be described in detail below in conjunction with specific embodiment, but be not in order to limit the present invention.
Embodiment 1:
Ocimum basilicum L. medicinal material 4.5Kg, chopping, with 70% ethanol heating extraction 2 times, each 2 hours, add 14 times of ethanol for the first time, add 12 times of ethanol for the second time, ethanol extract is concentrated near doing, and gets the about 1.4Kg of ethanol extract, and the control relative density is about 1.2; Ethanol extract adds water-dispersion, with 1.5 ten thousand liters sherwood oils, 60,000 liters methylene dichloride (all being pure solvents) be extracted to successively colourless after, its remainder is concentrated into dried, the about 800g of medicinal extract R.Get R medicinal extract 150g and go up sp825 type polystyrene macroporous resin post after with water dissolution, with about 30 liter of 10% ethanol and about 45 liter of 30% ethanol elution near colourless after, use 50% and 70% ethanol (consumption is respectively 60 liters and 30 liters approximately) to be eluted to closely colourless again, elutriant is recycled to dried, obtains the about 20g of medicinal extract R1.Medicinal extract R1 is gone up silicagel column (column chromatography silica gel 200 orders) repeatedly, methylene chloride-methanol in varing proportions is an eluent, gradient elution, to methyl alcohol, retinue thin layer TLC detects gradient elution, merges identical elutriant from methylene chloride-methanol (19:1), composition changes the back and changes eluent, obtain 8 components of DL-DL8, select the component high performance liquid chromatography, C
18Reverse-phase chromatographic column (preparation type and half preparation type) is an eluent with the methanol-water, and gradient elution separates repeatedly, and retinue is carried out RP-HPLC and checked that the merging same composition obtains the saponins compound with formula I structure of the present invention.
With hydrogen spectrum, carbon spectrum qualitative detection, the result proves that this compounds comprises the compound of II, III, IV, V, VI structure at least, and analyzing and testing is as follows:
Analyze high performance liquid chromatography and separate waters 2695/2996HPLC
Chromatographic column: C18 post 5um 4.6 * 150mm
Moving phase: methanol-water gradient (10%:90%)-(80%:20%)
Flow velocity: 0.5ml
The DAD detector
| Compound | Compound I] | Compound III | Compound IV | Compound V | Compound VI |
| Retention time (min) | About 37 | About 36 | About 27 | About 34 | About 32 |
Structure is identified:
Compound I I
Compound I I has following physicochemical data: be white powder, m.p:270 ℃-272 ℃ (methanol-water) is soluble in methyl alcohol.Liebemann-Burchard reacting positive, point sample are in the silica gel G plate, and spray is with the Vanillin concentrated sulfuric acid solution, and in 105 ℃ of heating 5 minutes, spot was a red-purple; The MOLISH reacting positive.
Molecular formula is C
60H
96O
25, MALDI-TOF MS m/z 1239[M+Na]
+, 1255[M+K]
+, high resolution mass spectrum m/z 1239.6157[M+Na]
+ 1H-NMR (hydrogen spectrum) (500Hz, pyridine-d5): 6.33 (H-21, d, 10.5Hz), δ 4.19 (H-28,2H), the 1.91 (CH of angeloyl groups
3, 3H), δ 5.86 (alkene hydrogen), the δ 1.95 (CH of ethanoyl
3, 3H), the anomeric proton signal [δ 6.24,5.26,5.08,4.92] of four sugar.
13C-NMR (carbon spectrum) data see Table 1.
Pectinose proton (δ 4.92) H-1/H-4 (δ 4.53) in the NOE spectrum, (δ 4.92) H-1/H-3 observes NOE between (δ 3.11, parent nucleus C-3), illustrates that pectinose is β-D-type, and links to each other with parent nucleus C-3 beta-hydroxy; Glucose proton (δ 5.08) H-1/H-3 (δ 4.12) observes NOE between (δ 5.08) H-1/H-5 (δ 3.72), is illustrated as β-D-type; Glucose proton (δ 5.26) H-1/H-3 (δ 4.27) observes NOE between (δ 5.26) H-1/H-5 (δ 3.98), is illustrated as β-D-type; Observe NOE between rhamnosyl proton (δ 6.24) H-1/H-4 (δ 4.15), illustrate that hydroxyl is the α type; Observe NOE between (δ 4.65) H-16/H-28 (δ 4.19), illustrate that H-16 is the β type; (1H, d J=10.0Hz), therefore can determine that H-21 is the α position to H-21 δ 6.33, and H-22 is the β position.
The II structure is 3 β; 16 α; 22 α-trihydroxy--21 β-O-angeloyl groups-28-O-ethanoyl-olea-12-alkene-C-3-O-α-L-rhamanopyranosyl (1 → 2)-β-D-glucopyranosyl (1 → 4)-[β-D-glucopyranosyl (1 → 2)]-β-D-arabopyranose glycosides (21 β-O-angeloyl-28-O-acetylbarringtogenol C-3-O-α-L-rhmanopyranosyl (1 → 2)-β-D-glucopyranosyl (1 → 4) [β-D-glucopyranosyl (1 → 2)]-β-D-arabinospyranoside); be new compound, be called Ocimum basilicum L. saponin(e B (lysimachigenoside B) among the application.
Compound III
The physicochemical data of compound III: be white powder, m.p:268 ℃-270 ℃ (methanol-water) is soluble in methyl alcohol.The Liebemann-Burchard reacting positive, the MOLISH reacting positive.
MALDI-TOF MS m/z 1197[M+Na]
+, 1213[M+K]
+, high resolution mass spectrum m/z 1197.6053[M+Na]
+, molecular formula is C
58H
94O
24..
13The C-NMR data see Table 1.
Analysis-by-synthesis III's
1H-NMR,
13C-NMR and
1H-
1H COSY; HMQC; HMBC; the TOCSY data; determine that structure is 3 β; 16 α; 22 α; 28-tetrahydroxy-21 β-O-angeloyl groups-olea-12-alkene-C-3-O-α-L-rhamanopyranosyl (1 → 2)-β-D-glucopyranosyl (1 → 4)-[β-D-glucopyranosyl (1 → 2)]-β-D-arabopyranose glycosides (21 β-O-angeloylbarringtogenol C-3-O-α-L-rhmanopyranosyl (1 → 2)-β-D-glucopyranosyl (1 → 4) [β-D-glucopyranosyl (1 → 2)]-β-D-arabinospyranoside; be new compound, be called Ocimum basilicum L. saponin(e C (lysimachigenoside C) among the application.
Compound IV
The physicochemical data of compound IV: be white powder, m.p:249 ℃-250 ℃ (methanol-water) is soluble in methyl alcohol.The Liebemann-Burchard reacting positive, the MOLISH reacting positive.The acid hydrolysis of thin layer original position launches, and detects glucose, rhamnosyl and pectinose.
ESI-MS m/z 1115.6[M+Na]
+, molecular formula is C
53H
88O
23δ 4.63 (1H, J=9.5Hz, H-22 β), δ 4.79 (1H, J=9.5Hz, H-21 α), anomeric proton δ 4.78, δ 5.39, δ 6.45, the δ 5.24 of sugar;
13The C-NMR data see the following form.IV structure: 3 β, 16 α, 21 β, 22 α, 28-penta hydroxy group-12-alkene-olea-C-3-O-α-L-rhamnosyl glycosyl (1 → 2)-β-D-glucopyranosyl (1 → 4)-[β-D-glucopyranosyl (1 → 2)]-β-D-arabopyranose glycosides (Barringtogenol C-3-O-α-L-rhmanopyranosyl (1 → 2)-β-D-glucopyranosyl (1 → 4) [β-D-glucopyranosyl (1 → 2)]-β-D-arabinospyranoside, be new compound, be called Ocimum basilicum L. saponin D (lysimachigenoside D) among the application.
Table 1. Compound I I, III, IV's
13C-NMR (carbon spectrum) (125Hz, pyridine-d5) data
Compound V
Compound V physicochemical data: be white powder, m.p:282 ℃-283 ℃ (methanol-water) is soluble in methyl alcohol.Liebemann-Burchard reacting positive, point sample are in the silica gel G plate, and spray is with the Vanillin concentrated sulfuric acid solution, and 105 ℃ were heated 5 minutes, and spot is a red-purple.The MOLISH reacting positive, the acid hydrolysis of thin layer original position can detect glucose and pectinose.
MALDI-TOF MS shows that quasi-molecular ion peak is m/z1443[M+Na]
+, 1459[M+K]
+High resolution mass spectrum shows molecular ion peak: 1443.6719[M+Na]
+, molecular formula is C
68H
108O
31 1HNMR (500Hz, pyridine-d
5): δ 2.20 (1H, H-21), 2.10 (1H, H-21), δ 6.0 (1H, s, H-28), δ 1.9 (3H, s, CH
3), δ 2.1 (3H, s, CH
3), δ 5.83 (1H, s, H-16), δ 1.60 (H-15), δ 2.00 (3H, s, ethanoyl CH3), δ 3.80-δ 5.20 (hydrogen signal of sugar).
13The C-NMR data see Table 2.
The V structure is 3 β; 22 alpha-dihydroxy-s-16 α-O-ethanoyl-28-O-angeloyl groups-olea-12-alkene-C-3-O-β-D-glucopyranosyl (1 → 4)-6 '-ethanoyl-β-D-glucopyranosyl (1 → 6)-β-D-glucopyranosyl (1 → 4)-[β-D-glucopyranosyl (1 → 2)]-β-D-arabopyranose glycosides (3 β; 22 α-dihydroxy-16 α-O-acetyl-28-O-angeloyl-olean-12-en C-3-O-β-D-glucopyranosyl (1 → 4)-6 '-acetyl-β-D-glucopyranosyl (1 → 6)-β-D-glucopyranosyl (1 → 4)-[β-D-glucopyranosyl (1 → 2)]-β-D-arabinospyranoside); be new compound, be called Ocimum basilicum L. saponin(e E (lysimachigenoside E) among the application.
Compound VI
The compound VI physicochemical data: be white powder, m.p:246 ℃-247 ℃ (methanol-water) is soluble in methyl alcohol.Liebemann-Burchard reacting positive, point sample are in the silica gel G plate, and spray is with the Vanillin concentrated sulfuric acid solution, and in 105 ℃ of heating 5 minutes, spot was a red-purple, the MOLISHI reacting positive, and the thin layer in-situ hydrolysis launches, and can detect glucose and pectinose.
13The C-NMR data see Table 2.
The VI structure is 3 β; 22 alpha-dihydroxy-s-16 α-O-ethanoyl-28-O-angeloyl groups-olea-12-alkene-C-22-O-β-D-glucosyl group-C-3-O-β-D-glucose (1 → 6)-β-D-glucosyl group (1 → 4)-[β-D-glucosyl group (1 → 2)]-β-D-pectinose β-D-glucopyranosyl (1 → 2)-β-D-arabopyranose glycosides (3 β; 22 α-dihydroxy-16 α-O-acetyl-28-O-angeloyl-olean-12-en-C-22-O-β-D-glucopyranosyl-C-3-O-β-D-glucopyranosyl (1 → 4)-β-D-glucopyranosyl (1 → 6)-β-D-glucopyranosyl (1 → 4)-[β-D-glucopyranosyl (1 → 2)]-β-D-arabinospyranoside are called Ocimum basilicum L. saponin(e F (lysimachigenoside F) among the application.
Table 2. compound V, VI's
13The C-NMR data (125Hz, pyridine-d5)
More than described the preferred embodiment for the present invention, so it is not that those skilled in the art can not depart from the improvement and the variation of category of the present invention and spirit to embodiment disclosed herein in order to qualification the present invention.
Claims (7)
1, a kind of saponins compound is characterized in that, this saponins compound has following structure:
2. saponins compound as claimed in claim 1, wherein this compound derives from the extract of Primulaceae Lysimachia Ocimum basilicum L. plant.
3, the preparation method of the described compound of claim 1, comprising to the Ocimum basilicum L. plant with the extraction of ethanol-extracted, non-polar organic solvent, macroporous adsorbent resin refining and edulcoration and high performance liquid phase separating process.
4, preparation method as claimed in claim 3, comprising extracting with the ethanol heating, extracting solution with sherwood oil, methylene dichloride be extracted to successively colourless after, remove methylene dichloride, remaining liq concentrate medicinal extract, with macroporous adsorptive resins on the medicinal extract, use ethanol elution, elutriant reclaims, obtaining elutriant medicinal extract, again with silicagel column on this medicinal extract, is the eluent gradient elution with the methylene chloride-methanol of weight proportion 9:1～1:1, be merged into the identical elutriant of branch, use the methanol aqueous solution wash-out of high performance liquid chromatography more respectively with 10-50%.
5, the application of the described compound of claim 1 in preparation anti-inflammatory, antibacterial medicines.
6, a kind of pharmaceutical composition wherein contains the described compound of claim 1 and the pharmacy acceptable auxiliary of significant quantity.
7, pharmaceutical composition as claimed in claim 6, wherein this pharmaceutical composition is oral dosage form, injection type or percutaneous dosing formulation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100650433A CN100491393C (en) | 2006-03-15 | 2006-03-15 | Steroid saponins and preparation method and application |
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| 灵香草化学成分. 段文贵等人.广西化工，第24卷第3期. 1995 |
| 灵香草化学成分. 段文贵等人.广西化工，第24卷第3期. 1995 * |
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| 灵香草化学成分的初步研究. 成桂仁等.广西植物，第6卷第1期. 1986 * |
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