CN103614429B - Method for transforming gingko pollen flavonoid glycoside employing microorganisms - Google Patents
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Abstract
The invention discloses a method for transforming gingko pollen flavonoid glycoside employing microorganisms. By adopting the method, the gingko pollen flavonoid glycoside is transformed by using lactobacillus BL1. The bacterial strain is facultative anaerobic, simple in cultivation condition, quick to grow, strong in fertility, safe and efficient, can generate a plurality of complex enzymes, and can carry out growth and propagation by taking single gingko pollen as matrix. The gingko pollen does not need wall-breaking treatment in advance; the flavonoid glycoside in the gingko pollen does not need complicated extraction and purification, and is efficiently transformed into corresponding aglycone; the capability of directly taking the gingko pollen as the raw material to transform the flavonoid glycoside into corresponding aglycone is high. The conversion ratio of flavonoid glycoside kaempferide-3,4'-diosgenin-diglucoside, 3-O-[6-O(alpha-L-rhamnose base)-beta-D-glucosyl] kaempferide and kaempferol-3-glucoside is up to over 99 percent. The kaempferol which is over 100 times more than the former can be obtained from the gingko pollen by transformation. Thus, the bioavailability is greatly improved.
Description
Technical field
The invention belongs to microbial technology field, particularly a kind of method of microbial transformation Semen Ginkgo pollen flavonoid glycoside.
Background technology
Ginkgo has another name called " Gong Sunshu ", is Relict Plant the most ancient in existing spermatophyte.Ancient ginkgo is mainly distributed in China as wild resource, after introduce a fine variety all over the world.Ginkgo main producing region domestic at present mainly in Shandong, Jiangsu, Guangxi, the ground such as Guangdong.Ginkgo whole body is precious, and the utilization of gingko resource is with a long history in China, and Ginkgo Leaf, ginkgo nut can be used as medicine, all on the books in " Chinese Pharmacopoeia ".Containing the multiple components that natural radioactivity flavones and lactone etc. are useful with HUMAN HEALTH in Ginkgo Leaf, there is dissolving cholesterol, the effect of vasodilation, has positive effect to improving disordered brain function, arteriosclerosis, hypertension, dizzy, tinnitus, headache, senile dementia, hypomnesis etc.Its diseases prevention, cure the disease, the value of body-building is early on the books in the Compendium of Material Medica of Ming Dynasty's LI Shi-Zhen.Modern study shows; take flavones as the gingko leaf preparation of principle active component; there is protection capillary permeability, coronary artery dilator, recovery arteries elasticity, reduce serum cholesterol, increase coronary artery blood flow, improve cardiovascular and cerebrovascular circulation, remove the effect of smooth muscle spasm, lax segmental bronchus and antibacterial, nourishing brain cell and other organ, and make the blood matter in artery, peripheral vessel, capillary vessel and cholesterol maintain peculiar effect of normal level in addition.Ginkgo nut is nutritious, containing protein 13.2g in every 100g fresh fruit, carbohydrate 72.6g, fat 1.3g, and containing the various trace elements such as vitamins C, riboflavin, carotene and calcium, phosphorus, iron, selenium, potassium, magnesium, 8 seed amino acids, have very high edibleness, pharmaceutical use and health value.But also containing toxic ingredients such as ginkgoic acids in ginkgo nut, Ginkgo Leaf, the toxic side effect caused thus limits its range of application.
In recent years Semen Ginkgo pollen research and development utilize gradually pay close attention to by scientific circles.According to current research, Semen Ginkgo pollen nutrition is very abundant, and pharmaceutical ingredient content is high.Containing have an appointment 23.65% protein, 1.5% VC, 1.3% VB1,6.5% VB2,1.6% ~ 2.4% flavones, 0.09% ~ 0.38% other activeconstituents such as lactone and polysaccharide.Contriver is shown by toxicological test, during Semen Ginkgo pollen dosage 21.1g/kg, experiment mice has no adverse reaction, and can obviously increase male mice thymus gland coefficient and Spleen coefficient, show that the safety range taking Semen Ginkgo pollen is comparatively large, and there is certain immuno-potentiation.Have broad application prospects so develop Semen Ginkgo pollen.The further research of contriver to Semen Ginkgo pollen flavone component shows, Semen Ginkgo pollen flavones is the glucosides flavonoid glycosides composition of aglycon primarily of kaempferol, accounts for more than 95% of total flavones.The wherein two glucosides of kaempferide-3,4'-, 3-O-[6-O-(α-L-rhamanopyranosyl)-β-D-glucosyl] kaempferide, FNL and 3-O-(α-L-rhamanopyranosyl) kaempferide accounts for about 92% of Semen Ginkgo pollen flavonoid glycoside total amount.But extremely low as the content of the kaempferol of Main Flavonoids aglycon, only have about 25mg/kg.
Bioavailability study shows, the molecular structure of natural sugar glycoside is not the optimised form of its activation plays, aglycon is only the optimised form of activation plays, and most of natural glycoside component is only decomposed into aglycon under the effect of hydrochloric acid in gastric juice and human intestinal microorganism, and can be absorbed by the body utilization.But Semen Ginkgo pollen has thick pollen wall, acid and alkali-resistance and in human body the residence time short, the biotransformation capacity in human body is more weak, directly take then bioavailability well below Flavone aglycone.If glucoside type Semen Ginkgo pollen flavonoid glycoside can be changed into aglycone-type flavones in vitro, the biological activity of Semen Ginkgo pollen flavones just can be strengthened.
The bio-transformation of current flavonoid glycoside mainly contains acid-base method, enzymolysis process and microbial method.Applying maximum is acid-base method, and under acid-base condition, glycosidic link is ruptured, this mode aglycon yield can reach more than 95%, but the less stable of Flavone aglycone under acid-base condition, and not easily carry out suitability for industrialized production under strong acid or basic conditions, soda acid cost recovery is high, and environmental pollution is large.Enzymolysis process action condition is gentle, and many employing weak acid buffer solution, and Flavone aglycone is volatility not.But adopt commercialization pure enzymatic conversion effect often not good, need multiple enzyme with the use of, and higher with enzyme cost, technique is comparatively complicated.Microbial method comparatively speaking technique is simple, and cost is low, and environmental friendliness, and most critical is exactly that search out can the microorganism cultivated, security is high of Efficient Conversion flavonoid glycoside and being easy to.
At present, as follows at the report utilizing the flavonoid glycoside in natural plant raw material to generate in corresponding aglycon.CN101845467A discloses a kind of extracting method of kaempferol, mainly alkali is carried the extraction kaempferol that to combine with enzymolysis.Wu Yi etc. adopt beta-glucoside enzymic hydrolysis Folium Ginkgo extract, make glucoside type flavones be converted into aglycone-type flavones.Liu Ping etc. adopt the glycosyl in enzymatic hydrolysis sea-buckthorn glucosides to make it become aglycon, improve anti-oxidant activity.The method is: Fructus Hippophae flavone glucosides is after the prozyme pre-treatment that α-rhamnosidase (1 IU), beta-glucosidase (2 IU), zytase (1.5 IU), cellulase (15 IU), polygalacturonase (0.5 IU), α-amylase (2 IU) form, flavone glycoside transformation efficiency is only 0.23%, can obtain the Flavone aglycone of high-content again with naringinase hydrolysis, transformation efficiency reaches more than 85%.Fermentable bio-transformation glucosides aspect, Tian Tianli adopts head mold T-34 solid state fermentation converting giant knotweed, and under top condition, polygonin transformation efficiency reaches 98%.CN101575575A discloses a strain penicillium notatum and the application in biotransformation mulberry leaf flavonoid glycoside thereof, and flavonoid glycoside transformation efficiency reaches as high as 57%.The research of current microbial method bio-transformation flavonoid glycoside focuses mostly on and is utilizing fungi to carry out in bio-transformation, and biological transformation ratio differs, and the highest is utilize head mold T-34 to reach polygonin transformation efficiency 98%.
Milk-acid bacteria is the very high microorganism of a class security, is often used to the production of food and medicine.Part milk-acid bacteria is for can not cultivate bacterium or anerobe, can not cultivate or culture condition harshness, but also some milk-acid bacteria culture condition is simple, can grow on edible substrates, and amphimicrobian, less demanding to culture condition, the transformation ratio that bacterium carries out flavonoid glycoside from this part milk-acid bacteria utilizes fungi security higher.The research adopting microbial method to transform Semen Ginkgo pollen flavonoid glycoside has no report.
Bacterium lacticum BL1 is by applicant Agricultural Products Research Institute, Shandong Academy of Agricultural Sciences of patent of the present invention strain acid resistance lactic-acid-bacterium (Liu Xiaoyong that isolation identification is also preserved from pickles, Qiu Jiying, Sun Xin, Deng. the isolation identification of two strains of lactic acid bacteria and mixed culture pre-test thereof in pickles. Shandong agricultural sciences ［ J ］, 2012,44 (9): 85-89).Above-mentioned article is only reported its isolation identification.But do not report the function of this bacterial strain.
Summary of the invention
Instant invention overcomes the deficiency that existing bio-transformation flavonoid glycoside method aspect exists, provide one and utilize microorganism (Bacterium lacticum BL1) to transform the method for Semen Ginkgo pollen flavonoid glycoside.Bacterium lacticum BL1 can on single Semen Ginkgo pollen substratum growth and breeding, having Efficient Conversion Semen Ginkgo pollen flavonoid glycoside is the ability of Flavone aglycone.By bio-transformation of the present invention, Semen Ginkgo pollen does not need broken wall treatment in advance, and the flavonoid glycoside in Semen Ginkgo pollen does not need complicated extraction purification, and is become relevant aglycone by Efficient Conversion.Wherein Main Flavonoids glycosides (kaempferide-3, the two glucoside of 4'-, 3-O-[6-O-(α-L-rhamanopyranosyl)-β-D-glucosyl] kaempferide, FNL) transformation efficiency all up to more than 99%, the content of main converted product kaempferol can improve more than 100 times.
Technical scheme of the present invention is: a kind of method of microbial transformation Semen Ginkgo pollen flavonoid glycoside, is characterized in that,
(1) bacterial strain activation: Bacterium lacticum BL1 is streak culture on MRS solid medium, is separated single bacterium colony switching MRS slant medium, 37 DEG C cultivate 24 ~ 72 hours for subsequent use;
(2) liquid spawn: by inclined plane inoculating in liquid MRS substratum, cultivates 18 ~ 24 hours, obtains liquid spawn for 37 DEG C;
(3) preparation of fermented substrate: Semen Ginkgo pollen crosses 100 mesh sieves, by Semen Ginkgo pollen 10 ~ 40 weight part, the proportions of water 100 weight part also stirs;
(4) ferment: by fermented substrate in 115 DEG C of sterilizing 15 ~ 20min, be cooled to normal temperature, with 1% ~ 8% volume ratio inoculation liquid spawn, 30 DEG C ~ 37 DEG C quiescent culture 2 ~ 12 days, obtain the Efficient Conversion liquid of Semen Ginkgo pollen flavonoid glycoside.
Further, the preferred technical solution of the present invention is: being formulated as of described step (3) fermented substrate: by Semen Ginkgo pollen 20 weight part, and the proportions of water 100 weight part also stirs;
Further, the preferred technical solution of the present invention is: described step (4) fermentation is: by fermented substrate in 115 DEG C of sterilizing 15min, be cooled to normal temperature, with 4% volume ratio inoculation liquid spawn, 37 DEG C of quiescent culture 4-10 days, obtain the Efficient Conversion liquid of Semen Ginkgo pollen flavonoid glycoside.
Further, the further extraction purification of Semen Ginkgo pollen flavonoid glycoside Efficient Conversion liquid obtains natural kaempferol.
The Bacterium lacticum BL1 amphimicrobian that the present invention relates to, culture condition simple (can grow on common MRS substratum), produce multiple prozyme, growth rapidly, reproductivity is strong, safe and efficient, growth and breeding can be carried out using single Semen Ginkgo pollen as matrix, and bio-transformation Semen Ginkgo pollen flavonoid glycoside is that the ability of relevant aglycone is very high, three kinds of Main Flavonoids glycosides kaempferide-3, the two glucoside of 4'-, the transformation efficiency of 3-O-[6-O-(α-L-rhamanopyranosyl)-β-D-glucosyl] kaempferide and FNL all reaches more than 99%, higher than method disclosed in current bibliographical information or patent.Can obtain from Semen Ginkgo pollen than the kaempferol of many more than 100 times originally by transforming, substantially increasing the bioavailability of Semen Ginkgo pollen.The further extraction purification of Semen Ginkgo pollen flavonoid glycoside Efficient Conversion liquid can obtain natural kaempferol, kaempferol have anticancer, improve immunological competence, the multiple biological activity such as hypoglycemic, antibacterial, pharmaceutical industries can be widely used in or as food supplement.
Accompanying drawing explanation
Fig. 1 is the HPLC collection of illustrative plates before and after Semen Ginkgo pollen bio-transformation.(A), before bio-transformation, (B) adopts after Bacterium lacticum BL1 carries out bio-transformation; 1: the two glucoside of kaempferide-3,4'-, 2:3-O-[6-O-(α-L-rhamanopyranosyl)-β-D-glucosyl] kaempferide, 3: FNL, 4:3-O-(α-L-rhamanopyranosyls) kaempferide, 5: kaempferol.
Embodiment
Below in conjunction with embodiment, the present invention will be further described, but be not limited thereto.
Embodiment 1: the activation of the Bacterium lacticum BL1 that the present invention relates to and liquid spawn preparation
MRS solid medium is: peptone 5 g, extractum carnis 5 g, yeast extract paste 2. 5 g, glucose 2. 5 g, Triammonium citrate 1. 0 g, sodium acetate 1. 56 g, potassium acetate 1. 125 g, Sodium phosphate dibasic 0. 815 g, four water manganous sulfate 0. 125 g, magnesium sulfate heptahydrate 0. 29 g, tween 80 is 0. 5 ml, agar 10 g, distilled water 500 ml, pH6. 5,121 DEG C of sterilizing 20 min.
MRS slant medium is: with MRS solid medium.
Liquid MRS substratum is: for removing agar in MRS solid medium component.
Streak culture on MRS solid medium, be separated single bacterium colony switching MRS slant medium, 37 DEG C of cultivations carry out bacterial strain activation in 24 ~ 48 hours; By inclined plane inoculating in liquid MRS substratum, cultivate 18 ~ 24 hours for 37 DEG C, obtain liquid spawn, its useful viable count can reach 10
9cfu/mL.
Embodiment 2: the flavonoid glycoside bio-conversion process that the present invention relates to
Semen Ginkgo pollen crosses 100 mesh sieves, and by Semen Ginkgo pollen 20 weight part, the proportions of water 100 weight part also stirs and obtains fermented substrate; By fermented substrate in 115 DEG C of sterilizing 15min, be cooled to normal temperature, with 4% volume ratio inoculation Bacterium lacticum BL1 liquid spawn, 37 DEG C of quiescent culture 4 days, obtain the Efficient Conversion liquid of Semen Ginkgo pollen flavonoid glycoside.
Embodiment 3: the flavonoid glycoside bio-conversion process that the present invention relates to
Semen Ginkgo pollen crosses 100 mesh sieves, and by Semen Ginkgo pollen 30 weight part, the proportions of water 100 weight part also stirs and obtains fermented substrate; By fermented substrate in 115 DEG C of sterilizing 20min, be cooled to normal temperature, with 2% volume ratio inoculation Bacterium lacticum BL1 liquid spawn, 34 DEG C of quiescent culture 10 days, obtain the Efficient Conversion liquid of Semen Ginkgo pollen flavonoid glycoside.
Embodiment 4: the flavonoid glycoside bio-conversion process that the present invention relates to
Semen Ginkgo pollen crosses 100 mesh sieves, and by Semen Ginkgo pollen 25 weight part, the proportions of water 100 weight part also stirs and obtains fermented substrate; By fermented substrate in 115 DEG C of sterilizing 20min, be cooled to normal temperature, with 6% volume ratio inoculation Bacterium lacticum BL1 liquid spawn, 37 DEG C of quiescent culture 3 days, obtain the Efficient Conversion liquid of Semen Ginkgo pollen flavonoid glycoside.
Embodiment 5: the further extraction purification of Semen Ginkgo pollen flavonoid glycoside Efficient Conversion liquid obtains natural kaempferol
Get in 1L Semen Ginkgo pollen conversion fluid the dehydrated alcohol adding 1.5-4 kilogram, in 40-80 DEG C of heating and refluxing extraction or ultrasonic extraction 20-40 minute, filter, filter residue 60-80% aqueous ethanolic solution repeats to extract 1-3 time.Collect filtrate, underpressure distillation removing ethanol, remaining aqueous solution first uses equivalent petroleum ether extraction 3 times, then uses equivalent extraction into ethyl acetate 3 times, collects ethyl acetate and obtains flavone gruff bring up substance mutually.Adopt petroleum ether-ethyl acetate to be eluting solvent silica gel column chromatography repeatedly, merge kaempferol content higher composition, both natural kaempferol.
Embodiment 6: the detection of the Semen Ginkgo pollen flavone component that the present invention relates to
Sample pretreatment: the dehydrated alcohol adding 5 times of volumes in the Efficient Conversion liquid of original fermented substrate or embodiment 1, fully adopts 100-500W, 40Hz, temperature control 40-80 DEG C ultrasonic extraction 30min after mixing.Be cooled to room temperature, 10000 turns of frozen centrifugation 10min, get the membrane filtration of 2mL supernatant liquor 0.45um, and 4 DEG C save backup.
HPLC testing conditions: by pretreatment sample solution injection liquid chromatography, adopts C18 chromatographic column, sample size 10 μ L; Moving phase: 0.2% acetic acid aqueous solution (A)-acetonitrile (B), 0 ~ 10min 12% ~ 15% Mobile phase B linear gradient, 10 ~ 20min 15% ~ 18% Mobile phase B linear gradient, 20 ~ 30min 18% ~ 21% Mobile phase B linear gradient, 30 ~ 40min 21% ~ 32% Mobile phase B linear gradient, 40 ~ 50min 32% ~ 55% Mobile phase B linear gradient, 50 ~ 80min 55% ~ 65% Mobile phase B linear gradient, the degree such as 80 ~ 85min 65% Mobile phase B, volumetric flow rate 1mL/min, column temperature 30 DEG C; Determined wavelength 265nm.
Detected result as shown in Figure 1.Kaempferide, FNL as can be seen from Figure 1: the Main Flavonoids glycosides of Semen Ginkgo pollen (the two glucosides of kaempferide-3,4'-, 3-O-[6-O-(α-L-rhamanopyranosyl)-β-D-glucosyl]) transformation efficiency all up to more than 99%; The content of main converted product kaempferol can improve more than 100 times.
Claims (5)
1. a method for microbial transformation Semen Ginkgo pollen flavonoid glycoside, is characterized in that, utilizes Bacterium lacticum BL1 fermented Semen Ginkgo pollen, flavonoid glycoside is wherein converted into relevant aglycone; Specifically comprise the following steps:
(1) bacterial strain activation: Bacterium lacticum BL1 is streak culture on MRS solid medium, is separated single bacterium colony switching MRS slant medium, 37 DEG C cultivate 24 ~ 72 hours for subsequent use;
(2) liquid spawn: by inclined plane inoculating in liquid MRS substratum, cultivates 18 ~ 24 hours, obtains liquid spawn for 37 DEG C;
(3) preparation of fermented substrate: by Semen Ginkgo pollen 10 ~ 40 weight part, the proportions of water 100 weight part also stirs;
(4) ferment: by fermented substrate high-temperature sterilization, be cooled to normal temperature, with 1% ~ 8% volume ratio inoculation liquid spawn, 30 DEG C ~ 37 DEG C quiescent culture 2 ~ 12 days, obtain the Efficient Conversion liquid of Semen Ginkgo pollen flavonoid glycoside.
2. the method for microbial transformation Semen Ginkgo pollen flavonoid glycoside as claimed in claim 1, it is characterized in that, Semen Ginkgo pollen is crossed 100 mesh sieves by described step (3).
3. the method for microbial transformation Semen Ginkgo pollen flavonoid glycoside as claimed in claim 1, is characterized in that, described step (4) by fermented substrate in 115 DEG C of high-temperature sterilization 15-20min.
4. the method for microbial transformation Semen Ginkgo pollen flavonoid glycoside as claimed in claim 3, it is characterized in that, described step (4) by fermented substrate in 115 DEG C of sterilizing 15min, be cooled to normal temperature, with the volume ratio inoculation liquid spawn of 4%, 37 DEG C of quiescent culture 4-10 days, obtain the Efficient Conversion liquid of Semen Ginkgo pollen flavonoid glycoside.
5. as the method for the microbial transformation Semen Ginkgo pollen flavonoid glycoside in claim 1-4 as described in any one, it is characterized in that, described step (3) is by Semen Ginkgo pollen 20 weight part, and the proportions of water 100 weight part also stirs.
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| CN105309856B (en) * | 2014-12-04 | 2019-09-03 | 山东省农业科学院农产品研究所 | A kind of gingko pollen fermentation oral liquid and preparation method thereof |
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