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Process for producing dammarane sapogenins and ginsenosides

a technology of dammarane sapogenin and ginsenoside, which is applied in the field of dammarane sapogenin, can solve the problems of difficult if not impossible separation of 20(r) and 20(s) epimers, and achieve the effect of surprising anti-cancer effect, unexpected and superior activity

Inactive Publication Date: 2005-05-26
PANAGIN PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0009] This invention relates to a group of novel sapogenins, their use in anti-cancer applications, and to a process for their production. More particularly, this invention pertains to a novel group of dammarane sapogenins, PAM-120, PBM-110 and PBM-100 (the dammarane sapogenin structure in these three sapogenins is specifically clean of any sugar moieties (glycons) at any position and a hydroxyl at C-20) and PAN-20 and PAN-30 (the dammarane sapogenin structure has sugar moieties (glycons) but is free of hydroxyl at C-20), obtained by chemical cleavage of dammarane saponins. The invention also includes a novel application of the said sapogenins for anti-cancer treatment by using them separately or together, and / or jointly with other drugs, as well as to the process of producing these novel sapogenins. Said novel dammarane sapogenins show surprising anti-cancer effect when applied. In particular, the novel dammarane sapogenins show unexpected and superior activity against multi-drug resistant cancers.

Problems solved by technology

Currently, mixtures of 20(R) and 20(S) epimers are very difficult if not impossible to separate.

Method used

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  • Process for producing dammarane sapogenins and ginsenosides
  • Process for producing dammarane sapogenins and ginsenosides
  • Process for producing dammarane sapogenins and ginsenosides

Examples

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Effect test

example 1

Preparation Process of Producing PAM-120, PBM-100, and PAN-20

[0111] [1] Ginseng crude extract 10 g was dissolved in 40 mL of 95% ethanol [0112] [2] Add 40 mL of 5 N NaOH [0113] [3] Pour into the reaction tank, and set temperature to 240° C., and pressure to 3.5 Mpa, for 1.5 hours [0114] [4] Reduce temperature to room temperature, and take the products out the tank [0115] [5] Add HCl to neutralize pH to about 7, and expend the volume to 800 mL using water [0116] [6] Extract 3 times with acetic ester, 100 mL each time [0117] [7] Combine all the extracts, and reduce the pressure to dry. Thus, obtain 3.8 g of dried extracts [0118] [8] Grind and dissolved the extract in 20 mL of methanol, and mix the methanol solution with silica gel [0119] [9] Dry up the mixture, and then grind to fine powder [0120] [10] Load the Silica gel column [0121] [11] Wash the column with 60 mL of ether:petroleum benzin (1:3), and thus, 250 mg of PAM-120, and 45 mg of PBM-100 were obtained [0122] [12] Wash the ...

example 2

Another Example of Preparation Process Producing PAM-120, PBM-100, and PAN-20

[0123] [1] 10 g of Ginseng crude extract was added into reaction tank [0124] [2] Add to the reaction tank 100 mL of 5 N NaOH [0125] [3] Set temperature to 270° C. and pressure to 4.5 Mpa for 1 hour [0126] [4] Reduce temperature to room temperature, then take out the products [0127] [5] Neutralize the pH to 7 using HCl [0128] [6] Filter and keep the solids [0129] [7] Dissolve the solids in 10 mL of 95% Ethanol [0130] [8] Add water to make ethanol content less than 5% [0131] [9] Sit still overnight [0132] [10] Filter and keep the solids [0133] [11] Dry the solids [0134] [12] Dissolved the solids in 10 mL of methanol [0135] [13] Filter and keep the solution [0136] [14] Dry the solution to obtain 3.6 g of products [0137] [15] Mix the products with 11 g of silica gel [0138] [16] Grind and then load the silica gel column [0139] [17] Wash the column with 100 mL of ether:petroleum benzin (1:3), and thus, 60 mg of ...

example 3

Preparation Process of Producing 20(S) / 20(R) Protopanaxadiol, 20(S) / 20(R) Protopanaxatriol and 20(S) / 20(R) Ginsenoside Rh2

[0141] [1] Ginseng crude extract 10 g was dissolved in 40 mL 95% ethanol [0142] [2] Add 40 mL 5 N NaOH [0143] [3] Pour into the reaction tank, and set temperature to 240° C., and pressure to 3.5 Mpa, for 1.5 hours [0144] [4] Reduce temperature to room temperature, and take the products out [0145] the tank [0146] [5] Add HCl to neutralize pH to about 7, and expand the volume to 800 mL using water [0147] [6] Extract 3 times with Ethyl acetic(EtoAc), 100 mL each time [0148] [7] Combine all the extracts, and reduce the pressure to dry. Thus, obtain 3.8 g of dried extracts [0149] [8] Grind and dissolved the extract in 20 mL of methanol, and mix the methanol solution with silica gel [0150] [9] Dry up the mixture, and then grind to fine powder [0151] [10] The powder was subjected to Silica gel column chromatography [0152] [11] Eluted with 60 mL of petroleum ether:EtOAc...

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Abstract

This invention relates to a process for producing sapogenins and ginsenosides comprising the steps of mixing a ginsenoside extract with water, mixing the ginsenoside extract and water with an alkali-metal alcoholate solution or a hydroxide-ethanol solution to produce a mixture; or, alternatively, mixing a ginsenoside extract with ethanol, mixing the extract and ethanol with alkali-metal alcoholates solution to produce a mixture. The resultant mixture is placed in a reaction tank so that the resultant mixture can undergo chemical reactions under high temperature and high pressure effective to produce sapogenins therefrom. The temperature of the reaction tank can range between 150-300° C. and the pressure can range between 2.5 to 8.4 MPa. After the reaction is completed, an intermediate product of a mix of ginsenosides and sapogenins from the ethanol mixture is collected and the desired sapogenins and ginsenosides are separated from the intermediate product by silica-gel-column chromatography.

Description

RELATED APPLICATIONS [0001] This application is a continuation-in-part of, and claims the benefit of, U.S. application Ser. No. 09 / 910,887, filed 24 Jul. 24, 2001, and U.S. application Ser. No. 09 / 982,018, filed 19 Oct. 2001. U.S. application Ser. No. 09 / 982,018 is a continuation-in-part of U.S. application Ser. No. 09 / 910,887. The disclosures of both applications are incorporated herein by reference.FIELD OF THE INVENTION [0002] This invention relates to novel dammarane sapogenins, their use in anti-cancer applications, and a process of producing dammarane sapogenins and ginsenosides. BACKGROUND OF INVENTION AND RELATED ART [0003] Since the beginning of the last decade, anti-cancer research has been increasingly directed to the discovery of novel anti-cancer agents obtained from natural sources, as well as identifying and preparing synthetic compounds found in natural sources. [0004] Ginseng saponins (dammarane saponins, also called “ginsenosides”, which are effective ingredients t...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/575A61K31/704A61K9/00A61K36/25A61P35/00C07J9/00C07J17/00
CPCC07J17/005A61P35/00
Inventor HUANG, WINTERQI, DONG FENG
Owner PANAGIN PHARMA INC
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