CN1291613A - Process for extracting verbascin - Google Patents

Abstract

A process for extracting verbascin includes such steps as breaking Scrophulariaceae plant, immersing in alcohol, distillation to obtain alcohol extract, dissolving in water, extracting with petroleum ether, ethyl acetate and n-butanol, dissolving in methanol, adding silicon gel, stirring, laying aside, baking, eluting chromatography with chloroform-methanol solvent, adding into silicon gel column, and eluting with ethyl acetate-alcohol solvent.

Description

A kind of extracting method of Verbascoside

The present invention relates to a kind of certain glucoside method of extracting from natural product, is the method for extracting Verbascoside from goatweed (Scrophulariaceae) more exactly.

The Verbascoside that extracts from goatweed is subject to people's attention because of some special pharmacological action that it had, but its extracting method rarely has disclosure.

The present invention provides a kind of method from goatweed extraction Verbascoside, and the method according to this invention can be extracted more purified Verbascoside.

Method of the present invention is: earlier the goatweed herb is pulverized, fully soak with ethanol, again soak solution is distilled ethanol extract, with the ethanol extract water dissolution, use sherwood oil behind the elimination insolubles successively, ethyl acetate and n-butanol extraction, will be with the n-butyl alcohol extract dissolve with methanol, adding silica gel is mixed thoroughly and solution is dried after for some time is placed in the back again in lysate, to dry the thing upper prop, be 12 to 1 to 3 to 1 chloroform-methanol solvent elution chromatography with volume ratio, and the elution chromatography thing is gone up silicagel column again, use ethyl acetate-ethanol solvent wash-out more again, finally obtain Verbascoside.

The present invention can also extract with following described method:

Goatweed is pulverized, with alcohol immersion and distill behind the ethanol extract, it with temperature earlier hot water dissolving's ethanol extract of 40～70 ℃, extract with 60～90 ℃ sherwood oil again, and then use ethyl acetate extraction, the gained extract is used n-butanol extraction again, and extract distills with the method for underpressure distillation.

Preferably adopt the indirect heating mode to dry with dissolve with methanol and after adding silica gel the propyl carbinol medicinal extract of gained in the present invention, the oven dry thing places on 200～300 order silicagel columns of 2000 grams and carries out chromatography.

In the present invention after, with the chloroform-methanol volume ratio be successively: (A) 12 to 1 with propyl carbinol medicinal extract dry method upper prop; (B) 10 to 1; (C) 8 to 1; (D) 6 to 1; (E) 4 to 1; (F) 3 to 1 solvent carries out the chromatography wash-out in proper order, and the chromatography thing of the chromatographic solution wash-out of the F component of learning from else's experience is gone up silicagel column again, carries out chromatography with the ethyl acetate-ethanol solvent again.

When in the present invention the chromatography thing with the chromatographic solution wash-out of F component being carried out chromatography again, the ratio of ethyl acetate-ethanol should be 3 to 1 for best in the used chromatographic solution.

The present invention can extract Verbascoside from goatweed, and can extract extremely pure Verbascoside by most preferred embodiment of the present invention.

Explain orally below in conjunction with embodiments of the invention:

Embodiment 1

Get the Herb of Resupinate Woodbetony herb of scrophulariaceae lousewort (Pedicularis) and pulverize for 3.5 kilograms, fully soak with ethanol and make wherein that effective ingredient leaches immersion liquid after fully leaching, adopt distillating method to boil off ethanol and get about 510 grams of ethanol extract.The gained ethanol extract is dissolved with 1000 ml waters, treat to filter after ethanol extract dissolves fully, the filtering insolubles, again ethanol extract is used sherwood oil, ethyl acetate and n-butanol extraction successively, get about 60 grams of petroleum ether extract, about about 40 grams of acetic acid ethyl ester extract, about 190 to 200 grams of propyl carbinol medicinal extract.Again propyl carbinol medicinal extract is dissolved with small amount of methanol, adding silica gel is mixed thoroughly and solution is dried with the mode of indirect heating after for some time is placed in the back again in lysate, to dry 200～300 purposes, 2000 gram silicagel columns on the thing, it with volume ratio 3 to 1 chloroform-methanol solvent elution chromatography, gained chromatography thing is gone up silicagel column again, use ethyl acetate-ethanol solvent wash-out once more again, it is darker to obtain color and luster, the mixture that contains Verbascoside of less than 1 gram.

When the method in early stage that adopts (is annotated: the treatment process before referring to chromatography) with last basic identical, but when chromatography, carry out chromatography (wherein in the elutriant weight ratio of chloroform and methyl alcohol can from 12 to 1 to 3 to 1) with the bigger chloroform-methanol solvent of volume ratio, can obtain to contain the mixture of Verbascoside too, and increasing with chloroform deal in the chromatographic solution that uses within the specific limits, gained mixture quantity also increases, these can constitute different embodiments of the invention, but after measured in these mixtures the content of Verbascoside present the trend of minimizing with the increase of chloroform consumption in the chloroform-methanol system elutriant.

Embodiment 2

Get the Herb of Resupinate Woodbetony herb and pulverize for 3.5 kilograms, leach immersion liquid after fully soaking with alcohol immersion again, will leach immersion liquid after the Herb of Resupinate Woodbetony after soaking is once more with alcohol immersion again, so triplicate merges three times ethanol extract.Adopting vacuum distillation method to boil off ethanol must about 570 gram ethanol extract.With the gained ethanol extract with 1000 milliliters of hot water dissolvings, treat that ethanol extract dissolves to be placed under the room temperature fully and cool off, then the aqueous solution is filtered, the water-insoluble of about 200 grams of filtering, again ethanol extract is used sherwood oil, ethyl acetate and n-butanol extraction successively, get about 75 grams of petroleum ether extract, about about 50 grams of acetic acid ethyl ester extract, about 230 grams of propyl carbinol part medicinal extract.Again propyl carbinol medicinal extract is dissolved with small amount of methanol, again solution is put under the infrared lamp after placement for some time after adding silica gel is mixed thoroughly in lysate and dried, to dry 200～300 purposes, 2000 gram silicagel columns on the thing, with the chloroform-methanol solvent elution chromatography of different volumes ratio, wherein the chloroform-methanol volume ratio is respectively in each time elutriant: (A) 12 to 1 successively; (B) 10 to 1; (C) 8 to 1; (D) 6 to 1; (E) 4 to 1; (F) 3 to 1, solvent carry out the chromatography wash-out, the part of getting the elutriant institute wash-out of F component goes up silicagel column again, is 3 to 1 ethyl acetate-ethanol solvent wash-out once more with weight ratio again, the Verbascoside that promptly obtains white powder nearly weighs 100 milligrams, through survey R _f=0.67.It is as follows that the gained Verbascoside is carried out the related detection result:

Molecular formula is C ₂₉O ₁₅H ₃₆, molecular weight is 624, the physical constant of its structure is:

Specific rotation: ${\[\mathrm{\α}\]}_D^{20}$ -68(C=0．4，MeOH)

Ultraviolet: ${\mathrm{UV\λ}}_{\max }^{\mathrm{MeOH}}$ (nm)：208(lgε4．30)，217(lgε4．45)

292(lgε4．10)，329(lgε4．25)

Infrared: ${\mathrm{IRv}}_{\max }^{\mathrm{KBr}}\left({\mathrm{cm}}^{-1}\right)$ : 3400 (OH), 2932 (C-H), 1700 (conjugation ester groups), 1631 (C-C), 1604,1521 (aromatic rings).

The hydrogen spectrum: ¹HNMR (400MHz, DMSO-d ₆, TMS) δ ppm:0.97 (d, J=6.0Hz, 3H, the methyl of rhamnosyl), 2.70 (t, J=7.0Hz, 2H, Ar-CH ₂-CH ₂), 4.36 (d, J=7.2Hz, 1H, the H-1 of glucose), (4.72 t, J=9.6Hz, 1H, the H-4 of glucose), 5.03 (d, J=1.1Hz, 1H, the H-1 of rhamnosyl), 6.21 (d, J=15.8Hz, 1H, Ar-CH=CH), 6.49-7.01 (6H, aromatic ring H), 7.47 (d, J=15.8Hz, 1H, Ar-CH=CH), 8.69,8.75,9.19,9.62 (4 * OH).

The carbon spectrum: ¹³CNMR (100MHz, DMSO-d ₆, TMS) δ ppm:129.1 (C-1), 116.3 (C-2), 145.0 (C-3), 143.5 (C-4), 115.8 (C-5), 119.5 (C-6), 70.2 (C-α), 35.0 (C-β), 125.5 (C-1 '), 114.7 (C-2 '), 145.5 (C-3 '), 148.4 (C-4 '), 113.6 (C-5 '), 121.4 (C-6 '), (115.5 C-α '), 145.5 (C-β '), 165.7 (C=O).Glucose: 102.3 (C-1), 74.5 (C-2), 79.1 (C-3), 69.1 (C-4), 74.5 (C-5), 60.7 (C-6).Rhamnosyl: 101.2 (C-1), 70.5 (C-2), 70.4 (C-3), 71.7 (C-4), 68.7 (C-5), 18.1 (C-6).

Mass spectrum: FABMS (m/s): 631[M+Li] ⁺, 64.7[M+Na] ⁺

Its molecular structure is as follows:

Claims (5)

1, the extracting method of Verbascoside, pulverize with the goatweed herb, leaching makes, it is characterized in that the goatweed herb is pulverized the back uses earlier alcohol immersion, again soak solution is distilled ethanol extract, with the ethanol extract water dissolution, use sherwood oil behind the elimination insolubles more successively, ethyl acetate and n-butanol extraction, gained propyl carbinol medicinal extract dissolve with methanol, adding silica gel is mixed thoroughly and solution is dried after for some time is placed in the back again in lysate, to dry the thing upper prop, be 12 to 1 to 3 to 1 chloroform-methanol solvent elution chromatography with volume ratio, and the elution chromatography thing is gone up silicagel column again, with ethyl acetate-ethanol solvent wash-out again, obtain Verbascoside.

2, Verbascoside extracting method according to claim 1, it is characterized in that with temperature be 40～70 ℃ of hot water dissolving's ethanol extracts, extract with 60～90 ℃ sherwood oil again, and then use ethyl acetate extraction, use n-butanol extraction again, distill with the method for underpressure distillation then.

3, according to the extracting method of the described Verbascoside of claim 2, it is characterized in that propyl carbinol medicinal extract adopts the indirect heating mode to dry with dissolve with methanol and after adding silica gel, the oven dry thing places on 2,000 200～300 order silicagel columns that restrain and carries out chromatography.

4,, it is characterized in that behind the propyl carbinol medicinal extract dry method upper prop with the chloroform-methanol volume ratio being successively: (A) 12 to 1 according to the extracting method of the described Verbascoside of claim 3; (B) 10 to 1; (C) 8 to 1; (D) 6 to 1; (E) 4 to 1; (F) 3 to 1 solvent carries out the chromatography wash-out, gets the chromatography thing of F component and goes up silicagel column again and carry out chromatography with the ethyl acetate-ethanol solvent again.

5,, it is characterized in that the weight ratio of chromatographic solution ethyl acetate-ethanol when chromatography thing to the F component carries out chromatography again is 3 to 1 according to the extracting method of the described Verbascoside of claim 4.