CN104926766A - Method for synchronous extraction of quercetin and nuciferine from lotus leaves - Google Patents
Method for synchronous extraction of quercetin and nuciferine from lotus leaves Download PDFInfo
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- CN104926766A CN104926766A CN201410094870.XA CN201410094870A CN104926766A CN 104926766 A CN104926766 A CN 104926766A CN 201410094870 A CN201410094870 A CN 201410094870A CN 104926766 A CN104926766 A CN 104926766A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
Abstract
The invention discloses a method for synchronous extraction of quercetin and nuciferine from lotus leaves; firstly, lotus leaf flavonoids are extracted by alkaline water, then lotus leaf alkaloids are extracted with high-proficiency methanol in an alkaline environment, and not only is the purpose of preliminary separation of the flavonoids and the alkaloids achieved, but also full utilization of resources is achieved; the alkali extraction liquid almost does not make the alkaloids loss, while a part of flavonoids which are not extracted fully in the alcohol extraction liquid can be extracted, the alkaloids are dissolved by an acid after the alcohol extraction liquid is subjected to alcohol recovery and concentration, the flavonoid substances are not dissolved in the acid, the alkaloid substances and the flavonoid substances are separated through filtration, a filter residue is the flavonoid substances for recycling, and the filtrate is alkalified by acid water to obtain an alkaloid precipitate. A flavonoid crude product obtained by filtration after acid precipitation of the alkali extraction liquid and an acid insoluable substance (flavonoids) of the alcohol extraction part are subjected to combined treatment, so as to extract quercetin. The alkalified alkali water of the alcohol extraction part and a supernatant of an alkali extraction part are mixed, loaded in a macroporous adsorption resin column and then adsorbed by D101 resin, and the residual partial alkaloids and flavonoids in the waste liquid are recycled so as to increase the yield and reduce the cost.
Description
Technical field
Plant extract biotechnology.
Background technology
Lotus leaf is nymphaeaceae plant lotus
nelumbonuciferathe leaf of Gaertn, has another name called lotus leaf, lotus root leaf, and in China, the South and the North all has plantation, is among the peoplely widely used in food and medicine.Because of the comparatively large and wide material sources of its use value, recent people strengthen the research to its active chemical components and pharmacology aspect, further clear and definite relation contained by it between chemical composition (as flavones, biology total alkali etc.) and drug effect.Containing the Flavonoid substances being main component with Quercetin (Quercetin) in lotus leaf, and content is very abundant.The discovery of lotus leaf alkaloid started from for 19 beginnings of the century, that to study also be maximum class natural organic-compounds the earliest, from Japanese scholars Feitian, very male grade isolates Nuciferine (Nuc ifer ine) from lotus leaf, since nuciferine (Roem e rine) and O-demethyl Nuciferine (O-Nornuc ifer ine) 3 monomer components, from leaf, 16 alkaloid compounds are isolated so far.Quercetin have eliminate the phlegm preferably, antitussive action, and have certain antiasthmatic effect.In addition reduce blood pressure in addition, strengthen capillary resistance, reduce capillary fragility, reducing blood-fat, coronary artery dilator, increase the effects such as coronary flow.Be used for the treatment of chronic bronchitis.Also auxiliary therapeutic action is had to coronary heart disease and hyperpietic.Antitumor action and platelet aggregation-against: Quercetin can significantly Inhibitory promotion cancer agent effect, suppress the growth of in vitro malignant cell, suppress ehrlich's ascite cell DNA, RNA and protein synthesis.The alkaloid of lotus leaf has strong antimitotic effect " thus there is stronger bacteria resistance function.Lotus Leafextract can be strengthened the effect of Regular Insulin and suppress the absorption of blood sugar, and this may be relevant containing more rich flavonoid compound with lotus leaf.Lotus leaf has good fat reducing and weight reducing function and oxidation and removing free radicals effect.These achievements in research provide scientific basis by for the application of lotus leaf in food, medicine.Lotus leaf is natural medicine-food dual purpose plant, and containing biologically active factorss such as abundant flavones and alkaloids in lotus leaf, its effect such as " three fall " and fat-reducing receives much attention in recent years.Market is proposed a multitude of names about the protective foods of lotus leaf and tea drink, these products are mostly compound preparation, or lotus leaf crude extract, and quality product is uneven, and active ingredients is countless according to controlled.
At present, research extract flavones in lotus leaf and alkaloidal bibliographical information more, but be mostly in testing laboratory's stage, up to now, in lotus leaf, flavones and alkaloidal extraction also do not have suitability for industrialized production, and its technology is still in the research and probe stage.
The object of the present invention is to provide a kind of method of simultaneous extraction Quercetin and Nuciferine from lotus leaf, the method not only can apply to large-scale commercial production, and separation and purification goes out highly purified Quercetin and Nuciferine, to reach medicinal standard.
Summary of the invention
Technical scheme of the present invention is: a kind of method of simultaneous extraction Quercetin and Nuciferine from lotus leaf, is characterized in that: comprise the following steps,
1., by new new lotus leaf cleaning, air-dry, pulverize, cross 20 orders, obtain Lotus Leaf;
2. Lotus Leaf is added the sodium hydroxide solution of 0.5%, solid-liquid ratio is 1:15, and heat up 60 ~ 70 DEG C and extract 0.5 ~ 1 hour, filter to obtain alkali extracting solution, filtrate adjusts PH to 1 ~ 1.5 with hydrochloric acid, and standing sedimentation spends the night.
3. separation of supernatant, lower sediment thing filter press, filter cake A pending (A is total flavones crude product), filtrate and supernatant liquor merge (content has part biological alkali), adjust PH to 12 ~ 13 upper props (D101 macroporous adsorptive resins) with alkali.
4. above-mentioned 2 lotus leaf slags add 90% methanol extraction lotus leaf alkaloid after pressing dry, and solid-liquid ratio is 1:8, extract 2 times, about temperature 70 C, 1 ~ 1.5 hour extraction time, extract complete, filter to obtain methanol extract liquid, united extraction liquid, reclaim under reduced pressure alcohol, to without alcohol, obtains concentrated extract B.
5., by the B dissolving with hydrochloric acid of 2%, cross and filter acid non-soluble substance, filtrate is alkalized, and has and precipitates generation in a large number, leaves standstill after crystallization sedimentation, filters to obtain filter residue C(alkaloid) until after step process.Filtrate and 3 bucks merge upper prop (D101 macroporous adsorptive resins).
6. buck upper prop is complete, and after polymeric adsorbent is saturated, with water-removing rinsing resin to colourless, effluent liquid PH is in neutral.Use the methanol-eluted fractions of more than 85% again, collect elutriant, recycling design, concentrating under reduced pressure, obtains elutriant medicinal extract D.
7. merge filter residue C and medicinal extract D, with the dissolving with hydrochloric acid of 2%, cross 300 order filter clothes, filtrate adjusts PH to 8 ~ 9 with alkali, with chloroform extraction 3-4 time, collect combined chloroform extraction liquid, heating recovery chloroform is to dry, residue hot ethanol dissolves, cooling crystallization, and suction filtration obtains Nuciferine coarse-grain.Highly purified Nuciferine fine work can be obtained again with ethyl alcohol recrystallization.
8. by filter cake A with 2% sulfuric acid dissolution, heating hydrolysis 40 ~ 60min, to precipitation aureus precipitation no longer increase, cooled and filtered precipitates, and filter cake a small amount of washing acid, drains after cleaning, Quercetin crude product, then use ethyl alcohol recrystallization can the Quercetin fine work of preparing high-purity.
Embodiment 1. gets the dry Lotus Leaf 5kg be ground into about 20 orders, add the aqueous sodium hydroxide solution 75L of 0.5%, be warming up to 70 DEG C of heating 40min, filter to get filtrate, filtrate adjusts pH value to 1.5 ~ 2 with hydrochloric acid, standing sedimentation spends the night, the methyl alcohol 40L adding 90% after the dregs of a decoction press dry is heated to 70 DEG C of extractions 1 hour, after filtering, condition of equivalent extracts second time, merge the alcohol extract of twice, reclaim under reduced pressure methyl alcohol, concentrate to obtain alcohol-extracted extract B, by B with 2% dissolving with hydrochloric acid, filter (300 order) and remove insolubles, filtrate alkalizes (adjusting PH11-12) with alkali, separate out precipitation, filtering-depositing obtains filter residue C, filtrate upper prop (D101 macroporous adsorptive resins).The lower sediment that above-mentioned sedimentation is spent the night is crossed filter press, obtains filter cake A(total flavones crude product 276G) pending.Filtrate and supernatant liquor merge, and adjust D101 macroporous adsorptive resins on pH value to 8-9, adsorb with alkali.The saturated rear clear water rinsing resin of resin absorption is clean, then uses 90% methanol-eluted fractions, collects elutriant, reclaims methyl alcohol, is condensed into thick medicinal extract D.Merge C, D, with the dissolving with hydrochloric acid of 2%, cross and filter acid non-soluble substance, solution alkali adjusts PH8-9, with chloroform extraction 3-4 time, and combined chloroform extraction liquid, reclaim chloroform to dry, residual paste ethanol heating for dissolving, puts cold analysis crystalline substance, suction filtration obtains Nuciferine coarse-grain 22G, and HPLC detects purity and is about 83.5%, with ethyl alcohol recrystallization twice, obtain fine work 18G, extract yield 0.38%, total recovery 75%, HPLC detects purity and is about 95.6%.Get filter cake A276G with 2% sulfuric acid 5L dissolve, heating hydrolysis 45min, cooling, suction filtration, filter cake is drained after washing acid with water, obtains Quercetin crude product 62g, HPLC detect purity be about 75.2%, with ethanol repeatedly recrystallization, obtain the Quercetin fine work of obtained purity 95%.
Embodiment 2. gets the dry Lotus Leaf 50kg be ground into about 20 orders, add the aqueous sodium hydroxide solution 800L of 0.5%, be warming up to 70 DEG C of heating 60min, filter to get filtrate, filtrate adjusts pH value to 1.5 ~ 2 with hydrochloric acid, standing sedimentation spends the night, the methyl alcohol 400L adding 90% after the dregs of a decoction press dry is heated to 70 DEG C of refluxing extraction 1 hour, after filtering, condition of equivalent extracts second time, merge the alcohol extract of twice, reclaim under reduced pressure methyl alcohol, concentrate to obtain alcohol-extracted extract B, by B with 2% sulfuric acid dissolution, filter (300 order) and remove insolubles, filtrate alkalizes (adjusting PH11-12) with alkali, separate out precipitation, filtering-depositing obtains filter residue C, filtrate upper prop (D101 macroporous adsorptive resins).The lower sediment that above-mentioned sedimentation is spent the night is crossed filter press, obtains filter cake A(total flavones crude product 2870G) pending.Filtrate and supernatant liquor merge, and adjust D101 macroporous adsorptive resins on pH value to 8-9, adsorb with alkali.The saturated rear clear water rinsing resin of resin absorption is clean, then uses 90% methanol-eluted fractions, collects elutriant, reclaims methyl alcohol, is condensed into thick medicinal extract D.Merge C, D, with the sulfuric acid dissolution of 2%, cross and filter acid non-soluble substance, solution alkali adjusts PH8-9, with dichloromethane extraction 3-4 time, and combined chloroform extraction liquid, recycling design is to dry, and residual paste ethanol heating for dissolving, puts cold analysis crystalline substance, suction filtration obtains Nuciferine coarse-grain 235G, and HPLC detects purity and is about 81.5%, with ethyl alcohol recrystallization twice, obtain fine work 210G, extract yield 0.42%, total recovery 82%, HPLC detects purity and is about 93.6%.Get filter cake A276G with 2% sulfuric acid 50L dissolve, heating hydrolysis 45min, cooling, suction filtration, filter cake is drained after washing acid with water, obtains Quercetin crude product 590g, HPLC detect purity be about 78.2%.
Embodiment 3. gets the dry Lotus Leaf 10kg be ground into about 20 orders, add the aqueous sodium hydroxide solution 150L of 1%, be warming up to 70 DEG C of heating 60min, filter to get filtrate, filtrate adjusts pH value to 1.5 ~ 2 with hydrochloric acid, standing sedimentation spends the night, the methyl alcohol 85L adding 85% after the dregs of a decoction press dry is heated to 70 DEG C of refluxing extraction 1.5 hours, after filtering, condition of equivalent extracts second time, merge the alcohol extract of twice, reclaim under reduced pressure methyl alcohol, concentrate to obtain alcohol-extracted extract B, by B with 1% sulfuric acid dissolution, filter (300 order) and remove insolubles, filtrate alkalizes (adjusting PH11-12) with alkali, separate out precipitation, filtering-depositing obtains filter residue C, filtrate upper prop (D101 macroporous adsorptive resins).The lower sediment that above-mentioned sedimentation is spent the night is crossed filter press, obtains filter cake A(total flavones crude product 560G) pending.Filtrate and supernatant liquor merge, and adjust D101 macroporous adsorptive resins on pH value to 8-9, adsorb with alkali.The saturated rear clear water rinsing resin of resin absorption is clean, then uses 90% methanol-eluted fractions, collects elutriant, reclaims methyl alcohol, is condensed into thick medicinal extract D.Merge C, D, with the sulfuric acid dissolution of 2%, cross and filter acid non-soluble substance, solution alkali adjusts PH8-9, with dichloromethane extraction 3-4 time, and combined chloroform extraction liquid, recycling design is to dry, and residual paste ethanol heating for dissolving, puts cold analysis crystalline substance, suction filtration obtains Nuciferine coarse-grain 46G, and HPLC detects purity and is about 85.5%, with ethyl alcohol recrystallization twice, obtain fine work 39G, extract yield 0.39%, total recovery 76.6%, HPLC detects purity and is about 97.1%.Get filter cake A560G with 2% sulfuric acid 10L dissolve, heating hydrolysis 60min, cooling, suction filtration, filter cake is drained after washing acid with water, obtains Quercetin crude product 130g, HPLC detect purity be about 88.2%.
Embodiment 4. gets the dry Lotus Leaf 500kg be ground into about 20 orders, add the aqueous sodium hydroxide solution 8000L of 0.5%, be warming up to 75 DEG C of heating 60min, filter to get filtrate, filtrate adjusts pH value to 1.5 ~ 2 with hydrochloric acid, standing sedimentation spends the night, the methyl alcohol 4000L adding 90% after the dregs of a decoction press dry is heated to 70 DEG C of refluxing extraction 1 hour, after filtering, condition of equivalent extracts second time, merge the alcohol extract of twice, reclaim under reduced pressure methyl alcohol, concentrate to obtain alcohol-extracted extract B, by B with 2% sulfuric acid dissolution, filter (300 order) and remove insolubles, filtrate alkalizes (adjusting PH11-12) with alkali, separate out precipitation, filtering-depositing obtains filter residue C, filtrate upper prop (D101 macroporous adsorptive resins).The lower sediment that above-mentioned sedimentation is spent the night is crossed filter press, obtains filter cake A(total flavones crude product 29.6KG) pending.Filtrate and supernatant liquor merge, and adjust D101 macroporous adsorptive resins on pH value to 8-9, adsorb with alkali.The saturated rear clear water rinsing resin of resin absorption is clean, then uses 90% methanol-eluted fractions, collects elutriant, reclaims methyl alcohol, is condensed into thick medicinal extract D.Merge C, D, with the sulfuric acid dissolution of 2%, cross and filter acid non-soluble substance, solution alkali adjusts PH8-9, with chloroform extraction 3-4 time, and combined chloroform extraction liquid, reclaim chloroform to dry, residual paste ethanol heating for dissolving, puts cold analysis crystalline substance, suction filtration obtains Nuciferine coarse-grain 2.12G, and HPLC detects purity and is about 84.5%, with ethyl alcohol recrystallization twice, obtain fine work 2.27KG, extract yield 0.44%, total recovery 87%, HPLC detects purity and is about 97.6%.Get filter cake A29.6KG with 2% sulfuric acid 50L dissolve, heating hydrolysis 45min, cooling, suction filtration, filter cake is drained after washing acid with water, obtains Quercetin crude product 6.7g, HPLC detect purity be about 88.2%.
Accompanying drawing 1 process flow sheet.
Claims (6)
1. the method for simultaneous extraction Quercetin and Nuciferine from lotus leaf, is characterized in that: because Nuciferine is water insoluble, analogous alkaloid is also insoluble in buck, and lotus flavone is dissolved in hot water, is soluble in buck; The present invention first extracts lotus leaf alkaloid with high fluency methyl alcohol again with after potass extraction lotus flavone r in alkaline environment, has both reached the object handing over flavones and alkaloid initial gross separation, has also reached making full use of of resource; Alkali extract does not almost have alkaloid, part flavones is still had in alcohol extract, alcohol extract reclaims after alcohol concentrates and uses acid dissolve alkaloid, flavonoid thing is insoluble to acid, remove the Flavonoid substances in alkaloid after filtration, sour water alkalize to obtain alkaloid precipitation, alkali extracting solution filters to obtain acid non-soluble substance (flavonoid) merging treatment of flavones crude product and alcohol extracting part after acid is sunk, the supernatant liquor alkalization buck of alcohol extracting part and alkali being put forward part merges upper prop, use D101 resin absorption, part biological alkali residual in Recycling of waste liquid and flavonoid, to improve yield, reduce costs.
2. the extracting method according to claim power 1, it is characterized in that: Lotus Leaf is added 0.1 ~ 5%(preferably 0.5 ~ 1%) sodium hydroxide solution, solid-liquid ratio is preferred 1:10 ~ 15 of 1:10 ~ 20(), heat up 60 ~ 70 DEG C and extract 0.5 ~ 1 hour, filter to obtain alkali extracting solution, filtrate adjusts PH to 1 ~ 3(preferably 1 ~ 1.5 with hydrochloric acid), standing sedimentation spends the night, separation of supernatant, lower sediment thing filter press, filter cake A pending (A is total flavones crude product), filtrate and supernatant liquor merge (content has part flavones and alkaloid), macroporous adsorptive resins post (D101 macroporous adsorptive resins) on PH to 12 ~ 13 is adjusted with alkali.
3. the extracting method according to claim power 1, it is characterized in that: above-mentioned 2 alkali carry after lotus leaf slag press dry after add 90% methanol extraction lotus leaf alkaloid, solid-liquid ratio is 1:6 ~ 12 (preferred 1:8), extract 2 times, about temperature 70 C, 1 ~ 1.5 hour extraction time, extract complete, filter to obtain methanol extract liquid, united extraction liquid, reclaim under reduced pressure alcohol is extremely without alcohol, obtain concentrated extract B, by B with 2% dissolving with hydrochloric acid, cross and filter acid non-soluble substance (for crude flavonoid powder is recycled), filtrate is alkalized, have and precipitate generation in a large number, after leaving standstill crystallization sedimentation, filter to obtain filter residue C(alkaloid) until after step process, filtrate buck and 2 bucks merge macroporous adsorptive resins (D101 macroporous adsorptive resins).
4. buck upper prop is complete, and after polymeric adsorbent is saturated, with water-removing rinsing resin to colourless, effluent liquid PH in neutral, then uses the methanol-eluted fractions of more than 85%, collects elutriant, recycling design, concentrating under reduced pressure, obtains elutriant medicinal extract D(containing alkaloid and flavones).
5. merge filter residue C and medicinal extract D, with the dissolving with hydrochloric acid of 2%, cross 300 order filter clothes, filter residue (flavones) is recycled, filtrate adjusts PH to 8 ~ 9 with alkali, with chloroform extraction 3-4 time, collect combined chloroform extraction liquid, heating recovery chloroform is to dry, residue hot ethanol dissolves, cooling crystallization, suction filtration obtains Nuciferine coarse-grain, then can obtain highly purified Nuciferine fine work with ethyl alcohol recrystallization.
6. the acid-soluble filter residue of crossing of filter cake A and 3 and 5 is merged, with 1 ~ 10%(preferably 1 ~ 2%) sulfuric acid dissolution, heating hydrolysis 40 ~ 60min, to precipitation aureus precipitation no longer increases, cooled and filtered precipitates, and filter cake a small amount of washing acid, drains after cleaning, Quercetin crude product, then use ethyl alcohol recrystallization can the Quercetin fine work of preparing high-purity.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109966347A (en) * | 2019-03-29 | 2019-07-05 | 上海欧润化妆品有限公司 | A kind of extraction process of white pond lily flower extract |
| CN110669234A (en) * | 2018-07-03 | 2020-01-10 | 东北林业大学 | Preparation method of water-resistant PVA film |
-
2014
- 2014-03-17 CN CN201410094870.XA patent/CN104926766A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110669234A (en) * | 2018-07-03 | 2020-01-10 | 东北林业大学 | Preparation method of water-resistant PVA film |
| CN109966347A (en) * | 2019-03-29 | 2019-07-05 | 上海欧润化妆品有限公司 | A kind of extraction process of white pond lily flower extract |
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