WO1997009338A1 - Procede de production de lignine kraft soluble dans l'eau - Google Patents

Procede de production de lignine kraft soluble dans l'eau Download PDF

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Publication number
WO1997009338A1
WO1997009338A1 PCT/JP1995/001749 JP9501749W WO9709338A1 WO 1997009338 A1 WO1997009338 A1 WO 1997009338A1 JP 9501749 W JP9501749 W JP 9501749W WO 9709338 A1 WO9709338 A1 WO 9709338A1
Authority
WO
WIPO (PCT)
Prior art keywords
lignin
soluble
water
kraft lignin
kraft
Prior art date
Application number
PCT/JP1995/001749
Other languages
English (en)
Japanese (ja)
Inventor
Takehiko Ishida
Arata Ishida
Kenji Iiyama
Thi Bach Tuyet Lam
Naoki Yamamoto
Original Assignee
Takehiko Ishida
Arata Ishida
Kenji Iiyama
Thi Bach Tuyet Lam
Naoki Yamamoto
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Takehiko Ishida, Arata Ishida, Kenji Iiyama, Thi Bach Tuyet Lam, Naoki Yamamoto filed Critical Takehiko Ishida
Priority to PCT/JP1995/001749 priority Critical patent/WO1997009338A1/fr
Publication of WO1997009338A1 publication Critical patent/WO1997009338A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
    • C07G1/00—Lignin; Lignin derivatives

Definitions

  • the present invention relates to a water-soluble lignin which has an action such as macrophage activity as an anti-virus activity and an immune enhancing effect, and particularly to a water-soluble lignin having a small molecular weight which is easily absorbed from the intestinal tract even by oral administration.
  • the present invention relates to a method for producing a modified lignin.
  • AIDS is a viral disease that destroys the human body's immune system and causes death. It has spread very rapidly in countries around the world in recent years and has been in danger. Some of the phases have been developed and applied in clinical practice, and it has been pointed out that they also have various side effects.
  • Lignin in the pulp production process by the Kraft method is separated from polysaccharides, mainly cellulose, which is the main component of pulp, as lignin, and is eluted and removed at night. Transport nights containing large amounts of craft lignin are concentrated and burned in boilers. Some of them are sprayed into hot air prior to combustion and isolated as powdered kraft lignin, which is used as an industrial raw material.
  • Such kraft lignin has been conventionally made water-soluble by the introduction of a sulfomethyl group into an aromatic ring.
  • a known force requires a high temperature in production, and the introduction rate of a water-soluble group is not so high.
  • the problem of residual formalin used in manufacturing can also be an obstacle to its use as a drug. Disclosure of the invention
  • the present invention provides a water-soluble denatured lignin isolated and purified from a conventional culture medium after Shitake mushrooms and lignosulfonate removed from sulphite pulp wastewater, as such an anti-AIDS virus and an immunostimulating agent.
  • a water-soluble lignin having a low molecular weight that can be administered orally and having a very high anti-AIDS virus and immunostimulatory activity even at a low concentration can be obtained at low cost, easily and easily.
  • An object of the present invention is to provide a production method for producing from lignin.
  • Lactignin is composed of pulp by the kraft method iii. During the pulping by the Kraft method, the lignin in the wood material is severely cut by its main bond, the ether bond strength s, and its molecular weight is reduced to 350-4
  • the water-soluble lignin obtained by carboxymethylation of kraft lignin has a high yield, a very high concentration at a low concentration, an anti-AIDS virus and an immunostimulatory activity, and a molecular weight of about 4
  • the amount that can be absorbed from the intestinal tract and reach the tissues and cells containing the virus even after oral administration is small, and water-soluble denatured lignin or lignosulfonate isolated and purified from the culture medium after Shitake mushroom cultivation
  • Water-soluble lignin having the same effect as that of ⁇ was able to be S3 ⁇ 4i.
  • the degree of substitution of a water-soluble group, which is considered to play an important role in antiviral activity, that is, a carboxymethyl group is high and can be controlled according to the purpose.
  • FIG. 1 is a schematic diagram of the effect of water-soluble lignin.
  • Fig. 2 shows water-soluble sugarcane bagasse obtained by cultivating shiitake mushrooms, which is classified into water-soluble lignins that have a strong hydrophobicity and are further classified by molecular weight. It is. This was performed at 37 ° C in RPMI 1-1640 medium containing calo heat-inactivated FCS, penicillin and streptomycin with the addition of CD4 positive human T cell clones, HIV and water-soluble lignin. After culturing for days, the number of surviving cells was trended using the trypan blue staining method. A blank treated in the same manner without adding water-soluble lignin was used as a blank. This assay was also performed in Figures 3 to 5 below.
  • Figure 3 shows lignosulfonic acid purified by removing the coexisting inorganic salts by concentrating the sulphite pulp effluent and dropping it in ethanol.
  • the average molecular weight is about 35,000.
  • FIG. 5 relates to the kraft lignin of the present invention, in which the kraft lignin obtained by concentrating the sulfate pulp night and injecting it with sulfuric acid is dissolved in dioxane and coexisted by dropping into ether.
  • Figure 6 shows the addition of tritiated thymidine and water-soluble lignin to human bone marrow cell clones, culture at 37 ° C for 4 days, and measurement of the amount of tritium incorporated in DNA and release from tritium.
  • 5 is a chart quantifying the DNA synthesis ability by performing the above steps.
  • FIG. 7 is a chart showing the results obtained by adding water-soluble lignin to a commercially available reverse transcriptase, culturing at 37 ° C. for 4 days, and measuring the reversal activity by a conventional method.
  • Soluble Clough Bok lignin present invention any not toxic to cells even in clear aqueous solution of 200 ⁇ g / m 1 As from Fig. 5, 1 2. 5 g / m 1 and Le, At very low concentrations, growth of AIDS is inhibited almost 100% at 90% t, 25 Mg / m 1.
  • Isolation kraft lignin from the needle itt old or wide Wei goods are marketed are not subjected special purification processing power s, inorganic reagents used in the pulp, sugars and raw wood in partially eluted It also contains impurities other than lignin, such as the extracted components. In order to remove these impurities, about 10 times the amount of commercially available kraft lignin is used.
  • the purified kraft lignin is collected by centrifugation, washed with fresh getyl ether and centrifuged to remove getyl ether. After repeating the washing with getyl ether, wash once with petroleum ether in the low boiling point category, and then mushroom at low temperature.
  • the purified kraft lignin is made carboxymethyl and water-soluble by any of the following methods.
  • carboxymethylated kraft lignin 2 is isolated from carboxymethylated kraft lignin 1 by freeze-drying.
  • force Rubokishimechiru kraft lignin 1 only Fe Roh Ichire! 1 raw hydroxyl groups of the raw materials of kraft lignin is a force Rubokishimechiru of, location of the force Rubokishimechiru based on ⁇ about
  • the craft lignin according to the present invention is used as an antiviral active agent and an immunopotentiator, and is expected to be used as a drug for chicken virus Newu Castle disease caused by retrovirus.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

Cette invention concerne un procédé de production de lignine kraft soluble dans l'eau, lequel consiste à raffiner et à effectuer la carboxyméthylation de lignine kraft extraite du bois. Ce processus permet d'obtenir une lignine soluble dans l'eau à partir de la lignine kraft isolée que l'on peut facilement trouver sur le marché à prix réduit et en grandes quantités, laquelle lignine soluble possède une puissante activité antivirale même en faibles concentrations, peut être administrée oralement, et possède un faible poids moléculaire ainsi que des effets tant de lutte contre le virus du SIDA que de potentialisation immunologique.
PCT/JP1995/001749 1995-09-01 1995-09-01 Procede de production de lignine kraft soluble dans l'eau WO1997009338A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/JP1995/001749 WO1997009338A1 (fr) 1995-09-01 1995-09-01 Procede de production de lignine kraft soluble dans l'eau

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP1995/001749 WO1997009338A1 (fr) 1995-09-01 1995-09-01 Procede de production de lignine kraft soluble dans l'eau

Publications (1)

Publication Number Publication Date
WO1997009338A1 true WO1997009338A1 (fr) 1997-03-13

Family

ID=14126229

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1995/001749 WO1997009338A1 (fr) 1995-09-01 1995-09-01 Procede de production de lignine kraft soluble dans l'eau

Country Status (1)

Country Link
WO (1) WO1997009338A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006202607A (ja) * 2005-01-20 2006-08-03 Furukawa Co Ltd 鉛蓄電池用負極添加剤

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05294981A (ja) * 1992-04-14 1993-11-09 Mokushitsu Shinsozai Gijutsu Kenkyu Kumiai カルボキシアルキル化リグニン誘導体の製造方法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05294981A (ja) * 1992-04-14 1993-11-09 Mokushitsu Shinsozai Gijutsu Kenkyu Kumiai カルボキシアルキル化リグニン誘導体の製造方法

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
HOLZFORSCHUNG, Vol. 42, No. 5, (1988), ROBERT BREZNY et al., "Mild Coagulation of Aqueous Suspensions of Kraft Lignin and its Derivatives", pp. 335-336. *
HOLZFORSCHUNG, Vol. 42, No. 6 (1988), ROBERT BRENZNY et al., "The Ion-Exchanging Lignin Derivatives Prepared by Mannich Reaction with Amino Acids", pp. 369-373. *
HOLZFORSCHUNG, Vol. 47, No. 4 (1993), RAJESH K. JAIN et al., "Lignin Derivatives. II. Functional Ethers", pp. 325-332. *
TAPPI, J., Vol. 73, No. 6 (1990), ROBERT BRENZNY et al., "Specific Ion-Exchangers Based on Lignins and their Characterization by Silicon-29 NMR Spectroscopy", pp. 199-204. *
WOOD SCI. TECHNOL., Vol. 14, No. 1, (1980), W. LANGE et al., "The Carboxymethylation of Organosolv and Kraft Lignins", pp. 1-7. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006202607A (ja) * 2005-01-20 2006-08-03 Furukawa Co Ltd 鉛蓄電池用負極添加剤

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