CN1793161A - Process for extracting lupinol from betulin category plant - Google Patents
Process for extracting lupinol from betulin category plant Download PDFInfo
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- CN1793161A CN1793161A CN 200510003429 CN200510003429A CN1793161A CN 1793161 A CN1793161 A CN 1793161A CN 200510003429 CN200510003429 CN 200510003429 CN 200510003429 A CN200510003429 A CN 200510003429A CN 1793161 A CN1793161 A CN 1793161A
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- lupeol
- birch
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- betula
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Abstract
The invention discloses a method to distill lupeol from birch genus plant that includes the following steps: smashing the dry birch bark, using methylene chloride to take back flowing and distilling, recycling methylene chloride, placing for deposition, filtering, removing filtrate and the washing deposit by a little cyclohexane several time to remove the low polarity impurity; recrystallizing for three times by absolute ethyl alcohol and acetone, the lupeol would be gained. The invention has the advantage of low cost, common raw material, simple technology.
Description
Affiliated field
The invention belongs to natural product research, relate to a kind of natural product extraction that significant application value is arranged, particularly a kind of method of from the Betula plant, extracting Lupeol.
Background technology
Lupeol has tangible step-down, anti-inflammatory action, Nikinema etc. have carried out anti-Oleum Tiglii inductive dropsy of ear experiment to Lupeol and semi-synthetic organic acid acetic derivative thereof, the result shows, under every ear 0.4 μ mol/L dosage, they all have the activity of inhibition, wherein the strongest its inhibiting rate of hemisuccinic acid ester activity of Lupeol is 90%, and under the same dose, the inhibiting rate of anti-inflammatory drug indomethacin is 73%.
Lupeol suppresses the tumor growth effect in addition, studies show that Lupeol can make the human leukemia cell take place that the quantity of hypodiploid has increased by 28.5% in the apoptotic cell under 75 μ mol/L concentration, and has concentration and time-dependent manner; Wada etc. have reported that the another kind of Anticancer Effect and Mechanism of Lupeol is a DNA topoisomerase II restraining effect selectively, and its IC50 is 10.4 μ mol/L, and activity is better than cancer therapy drug Etoposide (Etoposide, IC50 are 50.0 μ mol/L).
Lupeol various plants (Root of Carles Indigo, hold a memorial ceremony for the red sage root, Quercus acutissima leaf, Herba Pellioniae repentis, blue or green mabi, root of Redbracted Lysidice, Root of Littleleaf Photinia, must the flower rattan) in distribution is all arranged, but content is all not high, extracting method about Lupeol, bibliographical information method mostly with extract the back extract with different solvents, again different piece is directly carried out silica gel or alumina column chromatography, gradient elution and getting.This method is difficult to suitability for industrialized production, because usually the plant milk extract composition is too complicated, extraction liquid directly carries out chromatography easy cross-diffusion of many compositions when preparing.
Summary of the invention
At the not high and existing deficiency of extracting the Lupeol technology of the Lupeol content in the above-mentioned plant, the object of the invention is to provide a kind of simple, low cost, high yield, be fit to industrial from the Betula plant method of separation Lupeol.The solution that realizes above-mentioned purpose is the method for separating Lupeol from the Betula plant, carries out according to the following steps:
(1) extracts
Method one: dry Betula plant bark is ground into meal, the methylene chloride reflux that adds 10～20 times of amounts is extracted, preceding twice each two hours, 1 hour for the third time, united extraction liquid, be condensed into corpusculum after, place and a small amount of beige precipitation occurs, refilter, filtrate concentrate crude product, further with a small amount of hexanaphthene repeatedly flush away hang down polar impurity and get faint yellow crude product.
Method two: dry Betula plant bark is ground into meal, and the methylene dichloride that adds 10～20 times of amounts adopts microwave and sonic oscillation method to extract.
(2) purifying
Dissolve above-mentioned crude product with dehydrated alcohol and acetone mixing solutions reflux, place crystallization, get white, needle-shaped crystals (content is more than 80%) twice with the method recrystallization.Further chromatographic separation on normal phase silicagel column is with sherwood oil; The organic solution wash-out of ethyl acetate=8: 1, the pure product of Lupeol.
(3) differentiate.
The Lupeol that the chromatography that takes a morsel obtains is with electric sample of Lupeol standard substance while; On the silica gel G plate, with developping agent (sherwood oil: acetone=4: 1; Hexanaphthene: ethyl acetate=3: 1; Ether: ascending development normal hexane=1: 1), treat to use developer (10% sulphuric acid soln respectively after organic solvent is flung to; Vanillin-concentrated sulfuric acid solution; Phosphorus molybdenum acid solution)) colour developing, the two Rf value is identical, solid colour.The Lupeol that the chromatography that takes a morsel obtains, carrying out fusing point test: mp120～121 a ℃ proof chromatography gained material is Lupeol.
The inventor finds pleasantly surprisedly; the Betula plant milk extract can be removed a lot of other materials before column chromatography through crystallization repeatedly at dehydrated alcohol and acetone mixing solutions; make the column chromatography efficient of back improve greatly; in addition in the Betula plant bark; red birch; the content of the bark of maple birch more has superiority at (greater than 2%) aspect its yield by the product of extracting method gained of the present invention, so the present invention has protected the method and the red birch of extracting Lupeol from the Betula plant; the bark of maple birch is in the application of extracting Lupeol in accordance with the method for claim 1.
Embodiment:
The specific embodiment that provides below in conjunction with the contriver is described in further detail the present invention.
Embodiment 1: according to technical scheme of the present invention, the Lupeol that extracts in the Betula plant carries out according to the following steps:
(1) extracts
Get the red Cortex Betulae Luminiferae of 200 gram exsiccant and be ground into 20 purpose meal, adding the 2L methylene chloride reflux extracts, preceding twice each two hours, 1 hour for the third time, united extraction liquid, be condensed into corpusculum after, place and a small amount of beige precipitation occurs, refilter, filtrate concentrate crude product, further with a small amount of hexanaphthene repeatedly flush away hang down polar impurity and get faint yellow crude product.
(2) purifying
Dissolve above-mentioned crude product with dehydrated alcohol and acetone mixing solutions reflux, place crystallization, get white, needle-shaped crystals (content is more than 80%) twice with the method recrystallization.Further chromatographic separation on normal phase silicagel column is with sherwood oil; The organic solution wash-out of ethyl acetate=8: 1, the pure product of Lupeol.
(3) differentiate.
The Lupeol that the chromatography that takes a morsel obtains is with Lupeol standard substance while point sample; On the silica gel G plate, with developping agent (sherwood oil: acetone=4: 1; Hexanaphthene: ethyl acetate=3: 1; Ether: ascending development normal hexane=1: 1), treat to use developer (10% sulphuric acid soln respectively after organic solvent is flung to; Vanillin-concentrated sulfuric acid solution; Phosphorus molybdenum acid solution)) colour developing, the two Rf value is identical, solid colour.The Lupeol that the chromatography that takes a morsel obtains, carrying out fusing point test: mp120～121 a ℃ proof chromatography gained material is Lupeol.
Embodiment 2: different is that used Betula plant is the maple Cortex Betulae Luminiferae in step 1 for present embodiment and embodiment 1.
Embodiment 3: different is to carry out refluxing extraction with chloroform in step 1 for present embodiment and embodiment 1.
Embodiment 4: different is to extract with the ultrasonic concussion method of methylene dichloride in step 1 for present embodiment and embodiment 1.
Embodiment 5: different is to extract with the ultrasonic concussion method of chloroform in step 1 for present embodiment and embodiment 1.
Embodiment 6: different is to carry out refluxing extraction with chloroform and extract in step 2 for present embodiment and embodiment 2.
Embodiment 7: different is to extract with the ultrasonic concussion method of methylene dichloride in step 2 to present embodiment with implementing 2.
Embodiment 8: different is to extract with the ultrasonic concussion method of chloroform in step 2 to present embodiment with implementing 2.
Reference
[1]. Fang Yuchun, Shang Hongqiang. the chemical ingredients to Herba Pellioniae repentis is studied, herbal medicine, 2004,35 (11) 1218-1219
[2].Nikiema?JB，Vanhaenlen-Fastre?R，Vanhaeien?M，et?al.Effects?of?anti-inflammatorytriterpenes?isolate?from?Leptadenia?hastate?latex?on?keratinocyte?proliferation.Phytotherapy?Res，2001，15(2)：131-134
[3]Aratanechemuge?Y，Hibasami?H，Sanpin?K，et?al.Induction?of?apoptosis?by?lupeolisolated?from?mokmen?in?human?promyeotic?leukemia?HL-60?cells.Oncology?reports，2004，11(2)：289-292
[4]Wada?S，Iida?A，Tanaka?R.Screening?of?Triterpenoids?isolated?from?phyllanthusflexuosus?for?DNA?topoisomerase?inhibitory?activity.J?NatProd，2001，64(12)：1545-1547
Claims (7)
1. method of from the Betula plant, separating Lupeol, carry out according to the following steps:
(1) extracts
Method one: dry Betula plant bark is ground into meal, adds methylene chloride reflux and extract united extraction liquid, after being condensed into corpusculum, place a small amount of beige precipitation of appearance, refilter, filtrate concentrate crude product, further with a small amount of hexanaphthene repeatedly flush away hang down polar impurity and get faint yellow crude product.
Method two: dry Betula plant bark is ground into meal, adds methylene dichloride and adopts microwave and sonic oscillation method to extract.
(2) purifying
Dissolve above-mentioned faint yellow crude product with dehydrated alcohol and acetone mixing solutions reflux, place crystallization, get white, needle-shaped crystals twice with the method recrystallization.Further chromatographic separation on normal phase silicagel column is with sherwood oil; The organic solution wash-out of ethyl acetate=8: 1, the pure product of Lupeol.
2. method of separating Lupeol from the Betula plant as claimed in claim 1 is characterized in that the Betula plant can be white birch, black birch, red birch, maple birch, Yue Hua.
3. method of separating Lupeol from the Betula plant as claimed in claim 2 is characterized in that the Betula plant can be white birch, black birch, red birch, maple birch, Yue Hua, and wherein preferred Betula plant is red birch, maple birch.
4. method of separating Lupeol from the Betula plant as claimed in claim 1 is characterized in that available chloroform replaces methylene dichloride in the described extraction step.
5. method of separating Lupeol from the Betula plant as claimed in claim 1 is characterized in that dehydrated alcohol and acetone ratio that crystallization is used are 1: 1～1: 4.
6. method of separating Lupeol from the Betula plant as claimed in claim 5 is characterized in that dehydrated alcohol that crystallization is used and the ratio of acetone the best are 1: 3.
7. the bark of red birch, maple birch is in the application of extracting Lupeol in accordance with the method for claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200510003429 CN1793161A (en) | 2005-12-31 | 2005-12-31 | Process for extracting lupinol from betulin category plant |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200510003429 CN1793161A (en) | 2005-12-31 | 2005-12-31 | Process for extracting lupinol from betulin category plant |
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| CN1793161A true CN1793161A (en) | 2006-06-28 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN 200510003429 Pending CN1793161A (en) | 2005-12-31 | 2005-12-31 | Process for extracting lupinol from betulin category plant |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103014090A (en) * | 2012-12-14 | 2013-04-03 | 福建农林大学 | Method for extracting bis-benzene oxepin-11(6H) keto-1, 10-dihydroxy, 3-methyl-7, 8-dimethoxy from Moller bacteria |
| CN103626829A (en) * | 2013-11-29 | 2014-03-12 | 中国计量学院 | Method for separating and preparing lupeol from diospyros rhombifolia hemsl. |
| CN111000849A (en) * | 2019-12-19 | 2020-04-14 | 淮阴师范学院 | Application and product of lupeol DYC-6 |
-
2005
- 2005-12-31 CN CN 200510003429 patent/CN1793161A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103014090A (en) * | 2012-12-14 | 2013-04-03 | 福建农林大学 | Method for extracting bis-benzene oxepin-11(6H) keto-1, 10-dihydroxy, 3-methyl-7, 8-dimethoxy from Moller bacteria |
| CN103626829A (en) * | 2013-11-29 | 2014-03-12 | 中国计量学院 | Method for separating and preparing lupeol from diospyros rhombifolia hemsl. |
| CN111000849A (en) * | 2019-12-19 | 2020-04-14 | 淮阴师范学院 | Application and product of lupeol DYC-6 |
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