Fractionated products obtained from gamboge resin, and medical uses of the same

Inactive Publication Date: 2011-12-15
TAIWAN SUNPAN BIOTECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, U.S. Pat. No. 6,462,041 B1 has disclosed neither a compound of Formula I that has a 32,33-epoxy group, nor a process for preparing the same.

Method used

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  • Fractionated products obtained from gamboge resin, and medical uses of the same
  • Fractionated products obtained from gamboge resin, and medical uses of the same
  • Fractionated products obtained from gamboge resin, and medical uses of the same

Examples

Experimental program
Comparison scheme
Effect test

example 1

Analysis of an Acetone-Extracted Product from Gamboge Resin (TSB-14) by Analytical RP-HPLC

[0169]An acetone-extracted product from gamboge resin, i.e., TSB-14, which was prepared according to Example 1 of U.S. Pat. No. 7,138,428 B2, was subjected to an analytical RP-HPLC analysis, so as to determine the chemical constituent(s) contained therein.

[0170]Briefly, 1.0 mg of the product TSB-14 was dissolved in 1 mL of acetone and then subjected to an analytical RP-HPLC analysis along the lines as described in the previous section of “General Procedures,” and an elution profile as shown in FIG. 1 was obtained.

[0171]Referring to FIG. 1, 35 major peaks (numbered from 1 to 35) are present in the elution profile of the product TSB-14 within the retention time of 0 to 80 minutes. According to the results shown in FIG. 1, the applicants postulated that it might be possible to isolate 35 compounds from the product TSB-14. To verify this postulation, the product TSB-14 was subjected to the followin...

example 2

Preparation of Purified Compounds from the Product TSB-14

A. Semi-Preparative RP-HPLC Analysis of the Product TSB-14

[0172]3 g of the product TSB-14 was dissolved in 30 mL of acetone / acetonitrile (v / v=1:9) and then subjected to a semi-preparative RP-HPLC analysis along the lines as described in the previous section of “General Procedures,” in which a mobile phase containing 0.05% TFA(aq.) / 65% acetonitrile(aq.)(35:65) was used. The elution profile thus obtained is shown in FIG. 2.

[0173]After comparing the two elution profiles shown in FIGS. 1 and 2, the major peaks 1-35 as identified in FIG. 1 were also identified in the elution profile of FIG. 2, which was subsequently divided into three regions, i.e., Region 1, which includes peaks 1-12 eluted at a retention time of 0 to 42 minutes; Region 2, which includes peaks 13 to 24 eluted at a retention time of 42 to 135 minutes; and Region 3, which includes peaks 25 to 35 eluted at a retention time of 135 to 280 minutes.

B. Preparation of Frac...

example 3

Identification and Characterization of Compounds Isolated and Purified from Fractions 1-3

[0188]The physical and chemical properties of the thirty five products purified as obtained from fractions 1-3 in the above Example 2 were analyzed according to the methodologies set forth in the preceding section of “General Procedures,” including melting point (mp) measurement, 1H-NMR, 13C-NMR, 1H-1H COSY, HMQC, HMBC, NOESY, EIMS, HREIMS, FABMS, and HRFABMS. The experimental data thus obtained are summarized below.

1. Product Gh-47:

[0189]Product Gh-47, which was purified from eluate 13 of fraction 2, was determined to have the following properties:

[0190]Yellow flake crystals; mp 204˜209° C.

[0191]EIMS m / z (relative intensity): 560 [M]+ (100), 545 (47), 532 (22), 517 (36), 405 (44), 389 (11), 363 (24), 349 (17), 307 (12), 287 (22), 285 (16), 245 (15), 215 (12), 189 (5).

[0192]1H-NMR (400 MHz, CDCl3): δ 7.56 (1H, d, J=6.9 Hz), 6.63 (1H, d, J=9.6 Hz), 5.51 (1H, d, J=9.6 Hz), 5.12 (1H, dd, J=13.6, 6....

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Abstract

Disclosed herein are seventeen new compounds and five fractionated products obtained from an acetone-extracted product of gamboge resin. The seventeen new compounds and the five fractionated products have activities in inhibiting the growth of tumor / cancer cells. In addition, the acetone-extracted product of gamboge resin and the five fractionated products obtained therefrom have analgesic and anti-inflammatory effects.

Description

CROSS-REFERENCE TO RELATED APPLICATION[0001]This application claims priority of Taiwanese Application No. 099119107, filed on Jun. 11, 2010.BACKGROUND OF THE INVENTION[0002]1. Field of the Invention[0003]This invention relates to seventeen new compounds and five fractionated products obtained from an acetone-extracted product of gamboge resin. The seventeen new compounds and the five fractionated products have been demonstrated to have activities in inhibiting the growth of tumor / cancer cells. In addition, the acetone-extracted product of gamboge resin and the five fractionated products obtained therefrom have been demonstrated to have analgesic and anti-inflammatory effects. Therefore, this invention also relates to the use of said acetone-extracted product of gamboge resin, the five fractionated products thereof, and the seventeen new compounds in the preparation of pharmaceutical compositions.[0004]2. Description of the Related Art[0005]Gamboge resin is the gum-resin secreted by ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K36/185A61K31/352C12N5/00A61P29/00
CPCC07D493/22A61K31/352A61P29/00A61P35/00A61P35/02A61K36/38
Inventor LEE, SEN-BIN
Owner TAIWAN SUNPAN BIOTECH DEV
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