CN105601683A - Method for extracting high-purity pseudopterosin from gorgonian - Google Patents

Method for extracting high-purity pseudopterosin from gorgonian Download PDF

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Publication number
CN105601683A
CN105601683A CN201610085354.XA CN201610085354A CN105601683A CN 105601683 A CN105601683 A CN 105601683A CN 201610085354 A CN201610085354 A CN 201610085354A CN 105601683 A CN105601683 A CN 105601683A
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gorgonian
pseudopterosin
extract
ultrafiltration
filtrate
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李欣航
张金龙
邱玉想
陈玉燕
毕天宇
蒋丽刚
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Proya Cosmetics Co Ltd
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Proya Cosmetics Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C07H1/08—Separation; Purification from natural products

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)

Abstract

The invention relates to a method for extracting high-purity pseudopterosin from gorgonian. The method is characterized by comprising the following steps that 1, quantitative gorgonian samples are weighed, cleaning, drying, shredding and sieving are conducted, and 60-80-mesh gorgonian coarse powder is prepared; 2, isododecane, methyl trimethicone and C13-C15 alkane are weighed to serve as an extracting agent, the gorgonian coarse powder is immersed in the extracting agent for extraction, separation is conducted, supernatant is taken and concentrated, and a gorgonian extract solution is obtained; 3, the prepared gorgonian extract solution is subjected to microfiltration through a 0.1-micrometer ceramic microfiltration membrane, and filtrate is obtained; 4, ultrafiltration is conducted on filtrate through a cellulose acetate fiber ultrafiltration membrane with the pore diameter of 1,000 Da, and ultrafiltration extract is obtained; 5, vacuum concentration is conducted on the ultrafiltration extract, vacuum drying treatment is conducted at 25-30 DEG C, and a solid product containing pseudopterosin is obtained. The method for extracting the high-purity pseudopterosin from the gorgonian has the advantages of being easy to operate, low in cost and capable of conducting industrial large-scale production.

Description

A kind of method of extracting high-purity pseudopterosin from gorgonian
Technical field
The invention belongs to natural product extracting technique field, relate to a kind of side that extracts high-purity pseudopterosin from gorgonianMethod.
Background technology
Gorgonian is dendritic colony, and there is the axis of calcium carbonate or cutin inside, and outside has been dispersed in osteocomma. Gorgonian at presentKind be about 1200 kinds, contain many novel structures, the diversified secondary metabolite of biologically active, there is important medicineBy value, the chemical composition of research gorgonian, for finding new active skull cap components, is enriched marine pharmacology and natural productsChemistry has important theory value.
Pseudopterosin (Pseudopterosins) is the material that a class contains tricyclic diterpene glycosides structure, has 26 kinds of derivatives,The chemical constitution that each derivative has diterpene three to encircle, and the different stereochemical structure that is sugared side chain or aglyconeDifference. Pseudopterosin is proved to be a kind of rare powerful anti-inflammatory and analgesic substance, while being applied in cosmetics, has other plantThe unrivaled maintenance power of releiving, can reduce the generation of pacifying various stimulation phenomenons, and increases moisture and the nutrient of skin. At presentTill, pseudopterosin only can extract in a small amount of fan coral in Bahamas Islands, therefore for active skull cap componentsThe refining technical research of extracting of pseudopterosin is very important.
At present, also considerably less for the research of extracting pseudopterosin from gorgonian both at home and abroad, only have a small amount of bibliographical information logicalCross synthetic method and produce pseudopterosin. Synthetic method report, in oxolane-methanol solvate, anti-23 DEG C of deprotonations by NaHShould, with 2,3,4-triacetyl-α-D-acetylbromoglycose reaction, obtain 9-triacetyl-β-xylopyranose, deacetylate andP-toluenesulfonyl, through column chromatography legal system type B error pterosin. At paper CoreyE.J., CarpinoP.EnantiospecifictotalsynthesisofPseudopterosinsAandE[J].JournalofTheAmericanChemicalSociety, in the method that 111:5472 – 5474 records, synthesis step is many, productive rateLose larger; And in building-up process, apply the organic solvent that a large amount of toxicity is large, as oxolane, carrene, chloroform, chlorineAcetonitrile equal solvent, the volatilization of solvent and recovery are large to the destruction of environment. In addition, the LipoTech company of the U.S. is from extra large whip grassThe recovery rate that extracts pseudopterosin is 0.5%-1%, and recovery rate is too low, and industrial production cost is high.
Solvent extraction method be will through pulverizing natural plants be soaked in solvent, make active ingredient contained in plant byCertain rule, is dissolved in solvent gradually, thereby is extracted, and this method is widely used in the extraction of natural products composition.The key of this method is, the selection of solvent and proportioning select suitable solvent can obtain low cost, high yield; Suitable joinsThan improving extraction efficiency. And it is simple to have technological operation, extraction conditions gentleness, with short production cycle, energy consumption is little, efficiency is high, greenThe plurality of advantages such as colour circle guarantor. The derivative of pseudopterosin has multiple, and the different solubility of different derivatives needs by configurationExtraction when different solvents can be realized multiple pseudopterosin derivative.
Summary of the invention
The object of the present invention is to provide a kind of method of extracting high-purity pseudopterosin from gorgonian, this method has operationSimply, cost is low, the advantage of can large-scale industrialization producing.
For solving the problems of the technologies described above, the present invention by the following technical solutions: a kind of high-purity puppet of extracting from gorgonianThe method of pterosin, is characterized in that: comprise the following steps:
A, take quantitative gorgonian sample, clean, dry, shred, sieve, make 60 ~ 80 object gorgonian meal, wherein dryDry temperature is controlled at 50 ~ 60 DEG C;
B, 1:07 ~ 0.95:0.72 ~ 0.88 measures the poly-trimethicone of Permethyl 99A, methyl, C by volume13-C15AlkaneHydrocarbon, after mixing, as extractant, the gorgonian meal that steps A is obtained is soaked in described extractant and extracts, and extracts temperatureBe 40 ~ 50 DEG C, extraction time is 0.5 ~ 1.5h, then carries out centrifugation, and centrifugal rotational speed 3500r/min, when separationBetween 25min, get supernatant concentration, obtain gorgonian extract solution;
C, gorgonian extract solution prepared by step B, adopt 0.1 μ m ceramic micro filter film, and through 3000r/min centrifugeCentrifugal 8 ~ 10min carries out micro-filtration, obtains filtrate;
The acetate fiber milipore filter that D, filtrate prepared by C step are 1000Da by aperture carries out ultrafiltration, controls temperature 20Under the condition of ~ 30 DEG C, pressure is 0.2 ~ 0.7MPa, with 1.0 ~ 2.0g/L input concentration, described filtrate is carried out to ultrafiltrationSeparate, obtain ultrafiltration extract;
E, the ultrafiltration extract that step D is obtained, carry out reduced pressure concentration, and vacuum drying treatment at 25 ~ 30 DEG C, is containedThe solid product of pseudopterosin.
Application liquid chromatograph-mass spectrometer is measured the content of pseudopterosin in pressed powder, its pseudopterosin purityBe greater than 98.0%, extraction efficiency is 3.05% ~ 4.20%.
The present invention, taking gorgonian as primary raw material, uses Permethyl 99A, the poly-trimethicone of methyl, C13-C15AlkaneIt is high that mixed solvent extracts pseudopterosin productive rate, and cost is low.
For the diterpene glycoside derivates in pseudopterosin in step B, according to the state itself being dissolved in different solvents, realTest result as shown in table 1 below:
The dissolved state of diterpene glycoside derivates in table 1 pseudopterosin
According to conclusion shown in table 1, diterpene glycosides A can only be dissolved by Permethyl 99A; Diterpene glycosides B can only be by the poly-trimethyl silica of methylAlkane dissolves; Diterpene glycosides C can only be dissolved by C13-C15 alkane. For this feature, can extract diterpene glycosides in pseudopterosin by separate solventDerivative A, B, C, shown in the extraction following steps of diterpene glycoside derivates:
The separate solvent of diterpene glycosides A extracts: in the gorgonian meal obtaining to steps A, add the Permethyl 99A of unit volume to carry outExtract; Extraction step is 40 ~ 50 DEG C for extracting temperature, and extraction time is 0.5～1.5h.
The separate solvent of diterpene glycosides B extracts: the methyl poly-three that adds unit volume in the gorgonian meal obtaining to steps AMethylsiloxane extracts; Extraction step is 40 ~ 50 DEG C for extracting temperature, and extraction time is 0.5～1.5h.
The separate solvent of diterpene glycosides C extracts: the C13-that adds unit volume in the gorgonian meal obtaining to steps AC15 alkane extracts; Extraction step is 40 ~ 50 DEG C for extracting temperature, and extraction time is 0.5～1.5h.
Record independent solvent extraction amount: record utilizes the poly-trimethicone of Permethyl 99A, methyl, the C13 of unit solvent-C15 alkane is respectively for the extracted amount of diterpene glycosides A, B, C, and record data. With Permethyl 99A, the poly-trimethyl silica of methylIt is as shown in table 2 below that alkane, C13-C15 alkane are that solvent extracts respectively the recovery rate numerical value of diterpene glycosides A, B, C.
The extraction of table 2 taking the poly-trimethicone of Permethyl 99A, methyl, C13-C15 alkane as solvent extraction diterpene glycosidesRate score
Preparation mixes extracts solvent: while extraction by unit different solvents respectively according to diterpene glycosides A, B, C that as above step obtainsExtracted amount, corresponding to the requirement of the amount of the chemical composition diterpene glycosides A of the pseudopterosin in specific gorgonian, B, C, designs differentOptimum solvent combines to extract the pseudopterosin extract requiring according to quantity and merges, and obtains optimum recovery rate, wherein optimum solvent groupClose the combination that refers to the quantity of solvent using while obtaining optimum pseudopterosin recovery rate. By experiment, devise optimum solvent combinationTo obtain the optimum recovery rate that extracts diterpene glycosides A, B, C simultaneously, result is as shown in table 3:
The recovery rate numerical value of diterpene glycosides is extracted in the combination of table 3 optimum solvent
According to shown in table 3, result is known, only has Permethyl 99A: methyl gathers trimethicone: the amount control of C13-C15 alkaneIn the time of 1:0.71:0.72 ~ 1:0.94:0.87, can obtain the pseudopterosin recovery rate up to 3.05% ~ 4.20%.
Compared with prior art, the present invention has the technique effect of following excellence:
The present invention has only overcome and to have extracted with single solvent, once can only extract the extraction efficiency that a pseudopterosin derivative causesLow, purity is low, and the shortcoming that productive rate is low is initiated and mixed according to a certain ratio by several solvents, under comparatively economic prerequisite, extractsObtain the method for relative high yield, highly purified pseudopterosin. The pseudopterosin extracting through the present invention can directly apply to cosmeticsFormula Development in, performance antiallergy, effect of moisturizing. This project technique advanced person used, extraction conditions gentleness, production cycleShort, cost is low, energy consumption is little, efficiency is high, environmental protection, is the effective ways that extract pseudopterosin from gorgonian, has goodApplication prospect.
Detailed description of the invention
Embodiment 1:
From gorgonian, extract a method for high-purity pseudopterosin, adopt following steps:
A, first take quantitative gorgonian sample, clean, 50 DEG C of constant temperature dryings, shred, sieve, make 60 object gorgonians thickPowder;
The solid-liquid ratio of B, preparation Permethyl 99A, the poly-trimethicone of methyl, C13-C15 alkane is 1:0.70:0.72Extractant, the gorgonian meal that steps A is made is soaked in this extractant, extract temperature be 45 DEG C, extraction time is 1H, by the extract obtaining through above-mentioned steps, with the centrifugal 25min of speed of 3500r/min, gets supernatant concentration, obtains puppetPterosin extract solution;
C, pseudopterosin extract solution step B being obtained with 0.1 μ m ceramic micro filter film carry out micro-filtration, further to remove impurity eliminationMatter, and through the centrifugal 8min of 3000r/min centrifuge, obtain micro-filtration filtrate;
The micro-filtration filtrate that the acetate fiber milipore filter that D, employing aperture are 1000Da obtains step C is carried out ultrafiltration, controls temperatureAt 25 DEG C, pressure is 0.3MPa, with the input concentration of 1.0g/L, filtrate is carried out to ultra-filtration and separation, obtains ultrafiltration extract;
E, the ultrafiltration extract that step D is obtained carry out reduced pressure concentration, at 25 DEG C, carry out vacuum drying treatment, make and containThe solid product extract of pseudopterosin, measures its productive rate by liquid chromatograph-mass spectrometer, and productive rate is 3.50%, pureDegree is 98.2%.
Embodiment 2:
From gorgonian, extract a method for high-purity pseudopterosin, adopt following steps:
A, first take quantitative gorgonian sample, clean, 55 DEG C of constant temperature dryings, shred, sieve, make 70 object gorgonians thickPowder;
The solid-liquid ratio of B, preparation Permethyl 99A, the poly-trimethicone of methyl, C13-C15 alkane is 1:0.73:0.83Extractant, the gorgonian meal that steps A is made is soaked in this extractant, extract temperature be 43 DEG C, extraction time is 1.2H, by the extract obtaining through above-mentioned steps, with the centrifugal 25min of speed of 3500r/min, gets supernatant concentration, obtains puppetPterosin extract solution;
C, the pseudopterosin extract solution step B obtaining being obtained with 0.1 μ m ceramic micro filter film carry out micro-filtration, further to removeDecontamination, and through the centrifugal 9min of 3000r/min centrifuge, obtain micro-filtration filtrate;
The micro-filtration filtrate that the acetate fiber milipore filter that D, employing aperture are 1000Da obtains step C is carried out ultrafiltration, controls temperatureAt 20 DEG C, pressure is 0.5MPa, with the input concentration of 1.5g/L, filtrate is carried out to ultra-filtration and separation, obtains ultrafiltration extract;
E, the ultrafiltration extract that step D is obtained carry out reduced pressure concentration, at 25 DEG C, carry out vacuum drying treatment, make and containThe solid product extract of pseudopterosin, measures its productive rate by liquid chromatograph-mass spectrometer, and productive rate is 3.71%, pureDegree is 98.5%.
Embodiment 3:
From gorgonian, extract a method for high-purity pseudopterosin, adopt following steps:
A, first take quantitative gorgonian sample, clean, 60 DEG C of constant temperature dryings, shred, sieve, make 75 object gorgonians thickPowder;
The solid-liquid ratio of B, preparation Permethyl 99A, the poly-trimethicone of methyl, C13-C15 alkane is 1:0.80:0.80Extractant, the gorgonian meal that steps A is made is soaked in this extractant, extract temperature be 40 DEG C, extraction time is 0.8H, by the extract obtaining through above-mentioned steps, with the centrifugal 25min of speed of 3500r/min, gets supernatant concentration, obtains puppetPterosin extract solution;
C, the pseudopterosin extract solution step B obtaining being obtained with 0.1 μ m ceramic micro filter film carry out micro-filtration, further to removeDecontamination, and through the centrifugal 9min of 3000r/min centrifuge, obtain micro-filtration filtrate;
The micro-filtration filtrate that the acetate fiber milipore filter that D, employing aperture are 1000Da obtains step C is carried out ultrafiltration, controls temperatureAt 28 DEG C, pressure is 0.4MPa, with the input concentration of 1.2g/L, filtrate is carried out to ultra-filtration and separation, obtains ultrafiltration extract;
E, the ultrafiltration extract that step D is obtained carry out reduced pressure concentration, at 25 DEG C, carry out vacuum drying treatment, make and containThe solid product extract of pseudopterosin, measures its productive rate by liquid chromatograph-mass spectrometer, and productive rate is 3.23%, pureDegree is 98.1%.
Embodiment 4:
From gorgonian, extract a method for high-purity pseudopterosin, adopt following steps:
A, first take quantitative gorgonian sample, clean, 60 DEG C of constant temperature dryings, shred, sieve, make 75 object gorgonians thickPowder;
The solid-liquid ratio of B, preparation Permethyl 99A, the poly-trimethicone of methyl, C13-C15 alkane is 1:0.90:0.85Extractant, the gorgonian meal that steps A is made is soaked in this extractant, extract temperature be 45 DEG C, extraction time is1.5h, by the extract obtaining through above-mentioned steps, with the centrifugal 25min of speed of 3500r/min, gets supernatant concentration, to obtain final productTo pseudopterosin extract solution;
C, the pseudopterosin extract solution step B obtaining being obtained with 0.1 μ m ceramic micro filter film carry out micro-filtration, further to removeDecontamination, and through the centrifugal 9min of 3000r/min centrifuge, obtain micro-filtration filtrate;
The micro-filtration filtrate that the acetate fiber milipore filter that D, employing aperture are 1000Da obtains step C is carried out ultrafiltration, controls temperatureAt 30 DEG C, pressure is 0.5MPa, with the input concentration of 1.5g/L, filtrate is carried out to ultra-filtration and separation, obtains ultrafiltration extract;
E, the ultrafiltration extract that step D is obtained carry out reduced pressure concentration, at 30 DEG C, carry out vacuum drying treatment, make and containThe solid product extract of pseudopterosin, measures its productive rate by liquid chromatograph-mass spectrometer, and productive rate is 4.16%, pureDegree is 98.7%.
Embodiment 5:
From gorgonian, extract a method for high-purity pseudopterosin, adopt following steps:
A, first take quantitative gorgonian sample, clean, 60 DEG C of constant temperature dryings, shred, sieve, make 75 object gorgonians thickPowder;
The solid-liquid ratio of B, preparation Permethyl 99A, the poly-trimethicone of methyl, C13-C15 alkane is 1:0.95:0.88Extractant, the gorgonian meal that steps A is made is soaked in this extractant, extract temperature be 40 DEG C, extraction time is 1.2H, by the extract obtaining through above-mentioned steps, with the centrifugal 25min of speed of 3500r/min, gets supernatant concentration, obtains puppetPterosin extract solution;
C, the pseudopterosin extract solution step B obtaining being obtained with 0.1 μ m ceramic micro filter film carry out micro-filtration, further to removeDecontamination, and through the centrifugal 9min of 3000r/min centrifuge, obtain micro-filtration filtrate;
The micro-filtration filtrate that the acetate fiber milipore filter that D, employing aperture are 1000Da obtains step C is carried out ultrafiltration, controls temperatureAt 25 DEG C, pressure is 0.6MPa, with the input concentration of 2.0g/L, filtrate is carried out to ultra-filtration and separation, obtains ultrafiltration extract;
E, the ultrafiltration extract that step D is obtained carry out reduced pressure concentration, at 25 DEG C, carry out vacuum drying treatment, make and containThe solid product extract of pseudopterosin, measures its productive rate by liquid chromatograph-mass spectrometer, and productive rate is 4.08%, pureDegree is 98.7%.

Claims (1)

1. a method of extracting high-purity pseudopterosin from gorgonian, is characterized in that: comprise the following steps:
A, take quantitative gorgonian sample, clean, dry, shred, sieve, make 60 ~ 80 object gorgonian meal, wherein dryDry temperature is controlled at 50 ~ 60 DEG C;
B, 1:07 ~ 0.95:0.72 ~ 0.88 measures the poly-trimethicone of Permethyl 99A, methyl, C by volume13-C15Alkane,After mixing, as extractant, the gorgonian meal that steps A is obtained is soaked in described extractant and extracts, and extracting temperature is 40~ 50 DEG C, extraction time is 0.5～1.5h, then carries out centrifugation, centrifugal rotational speed 3500r/min, disengaging time 25Min, gets supernatant concentration, obtains gorgonian extract solution;
C, gorgonian extract solution prepared by step B, adopt 0.1 μ m ceramic micro filter film, and through 3000r/min centrifugeCentrifugal 8 ~ 10min carries out micro-filtration, obtains filtrate;
The acetate fiber milipore filter that D, filtrate prepared by C step are 1000Da by aperture carries out ultrafiltration, controls temperature 20Under the condition of ~ 30 DEG C, pressure is 0.2 ~ 0.7MPa, with 1.0 ~ 2.0g/L input concentration, described filtrate is carried out to ultrafiltrationSeparate, obtain ultrafiltration extract;
E, the ultrafiltration extract that step D is obtained, carry out reduced pressure concentration, and vacuum drying treatment at 25 ~ 30 DEG C, is containedThe solid product of pseudopterosin.
CN201610085354.XA 2016-02-15 2016-02-15 Method for extracting high-purity pseudopterosin from gorgonian Pending CN105601683A (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020091093A1 (en) * 2000-11-28 2002-07-11 Jacobs Robert S. Anti-inflammatory compounds derived from Pseudopterogorgia elisabethae
CN101688172A (en) * 2007-04-30 2010-03-31 爱德华王子岛大学 Intend plain bacterium and the using method thereof of producing of coral

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020091093A1 (en) * 2000-11-28 2002-07-11 Jacobs Robert S. Anti-inflammatory compounds derived from Pseudopterogorgia elisabethae
CN101688172A (en) * 2007-04-30 2010-03-31 爱德华王子岛大学 Intend plain bacterium and the using method thereof of producing of coral

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DANIEL R. DAY，等: "Cyclodextrin Formulation of the Marine Natural Product Pseudopterosin A Uncovers Optimal Pharmacodynamics in Proliferation Studies of Human Umbilical Vein Endothelial Cells", 《MAR. DRUGS》 *
TYRONE FERNS，等: "Oxidations of erogorgiaene in pseudopterosin biosynthesis", 《TETRAHEDRON》 *
向江波: "《上海海洋大学硕士学位论文》", 28 February 2017 *

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