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Diterpene dimer compounds and pharmaceutical compositions and preparation method and application thereof

A technology of diterpene dimer and compound, applied in the field of natural medicinal chemistry, can solve the problems of few research reports and the like, and achieve the effect of good anti-tumor activity and good anti-parasitic activity

Active Publication Date: 2014-06-04
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, the literature also shows that the underground parts of the plants of the genus Rabdosia Japonica with abnormal rhizome morphology often have medicinal records, but so far there are few research reports on the underground parts of the plants of the genus, only Rabdosia Japonica (Burm. f.) Hara var. glaucocalyx (Maxim.) Hara] chemical composition study report

Method used

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  • Diterpene dimer compounds and pharmaceutical compositions and preparation method and application thereof
  • Diterpene dimer compounds and pharmaceutical compositions and preparation method and application thereof
  • Diterpene dimer compounds and pharmaceutical compositions and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Extraction, separation and purification of compound 1-20 of the present invention:

[0030] The rhizomes (5.5 kg) of the genus Camellia were dried in the shade, crushed to 30 mesh, extracted three times with 70% acetone at room temperature, 25 L each time, 24 h, the extracts were combined, and the extracts were concentrated under reduced pressure to obtain Suspend the extract with an appropriate amount of water, and then distribute it several times with ethyl acetate to obtain an ethyl acetate extract (115 g). The extract is dissolved in an appropriate amount of chloroform / acetone and mixed with silica gel 80-100 mesh, and then mixed with 1.2 kg of silica gel 200-300 mesh for column chromatography and sectioning, and gradient elution with chloroform / acetone (1 : 0-0 : 1) to obtain 8 main fractions, the chloroform fraction and the 9: 1 chlorine / acetone fraction Silica gel column chromatography was carried out, and 200:1-2:1 petroleum ether / ethyl acetate was used for grad...

Embodiment 2

[0032] Physical and Spectroscopic Data of Compounds 1-20 of the Invention:

[0033] Compound 1: colorless crystals (acetone), UV (MeOH) λ max (logε) 289.4(3.45), 209.6 (4.63) nm; IR (KBr) v max 3020, 2928, 2868, 1800, 1762, 1728, 1634, 1610, 1586, 1458, 1373, 1278, 1218, 1132, 1027, 943, 823, 756 cm -1 ; EIMS m / z 656 [M] + (5), 596 (25), 294 (44), 85 (75), 83 (100), 69 (40); 1 H and 13 See Table 1 and Table 2 for C NMR data.

[0034] Compound 2: colorless crystals (acetone), UV (MeOH) λ max (logε) 285.6(3.45), 208.6 (4.58) nm; IR (KBr) v max cm -1 ; ESIMS m / z 1336 [2M + Na + H] + , 680 [M + Na + H] + , 619 [M + Na – HOAc] + , 551 [M-HOAc-COOH] + ; 1 H and13 See Table 1 and Table 2 for C NMR data.

[0035] Compound 3: colorless crystals (acetone), UV (MeOH) λ max (logε) 284.1(3.73), 204.0 (4.90) nm; IR (KBr) v max 3421, 3081, 2930, 2869, 1800, 1737, 1716, 1647, 1466, 1368, 1231, 1125, 1045, 945, 819, 756 cm -1 ; EIMS m / z 672 [M] + (4), 671 (8), 62...

Embodiment 3

[0085] Cytotoxic activity detection of compounds of the present invention:

[0086] The cytotoxicity of the compound of the present invention to human gastric cancer cell line (SGC-7901), liver cancer cell line (SMMC-7721) and human erythrocytic leukemia cell line (K-562) was determined by MTT method. In the experiment, a negative control group (water), a DMSO solvent control group, a positive control group (mitomycin C) and different concentrations of test samples were set up, and each concentration was set in 2 parallels. Cells in the logarithmic growth phase were collected, counted with a hemocytometer, and inoculated in a 96-well flat-bottomed cell culture plate according to the amount of 4500 cancer cells per well, placed in 5% CO 2 , Humidity above 90%, cultured in 37 ℃ incubator. After 24 hours, take out and add a certain amount of sample to be tested, continue to cultivate for 3 days, take out and place under a microscope to observe the cell morphology of each well, r...

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Abstract

Diterpene dimer compounds 1-20, pharmaceutical compositions with the compounds as active components, and a preparation method thereof. The preparation method comprises the following steps: taking roots, rhizomes or tubers of lamiaceae plectranthus plants, performing direct cold leaching or thermal reflux extraction with an organic solvent of petroleum ether, n-hexane, chloroform, acetone, methanol, or ethanol, or firstly performing cold leaching or reflux extraction with the organic solvents, then performing extraction with ethyl acetate to obtain total extract, performing repeated chromatography of the total extract to obtain the compounds of the invention. Pharmaceutical compositions with the compounds of the invention as active components can be used for resisting tumor and parasitic diseases. An application of the compounds of the invention in preparation of antitumor agents and anti-parasitic agents comprises: applying the compounds with an amount of 1.6-200 microgram / mL to a substrate or a population, and optionally bonding with carriers and / or media to obtain good cytotoxic activity; applying the compounds with an amount of 0.4-277.8 microgram / mL to a substrate or a population, and optionally bonding with carriers and / or media to obtain good anti-parasitic activity.

Description

Technical field: [0001] The invention belongs to the field of natural medicinal chemistry, and in particular relates to a new class of diterpene dimer compounds, a preparation method thereof, a drug combination with such compounds as active ingredients, and their antitumor and antiparasitic effects. application. technical background: [0002] There are more than 150 species of Isodon or Rabdosia in the Labiatae family. There are 90 species and 21 varieties in my country, almost all over the country, but the most abundant species are in the southwestern provinces, among which 49 species and 15 species are distributed in Yunnan. variants. It has been reported in the literature that the stems and leaves of Camellia are rich in ent-kaurane diterpenoids, which are also the material basis for the biological activities of Camellia, such as antibacterial and antitumor. At the same time, the literature also shows that the underground parts of the plants of the genus Rabdosia Japonic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00C07J75/00A61K31/585A61P35/00A61P35/02A61P33/06
Inventor 姜北肖朝江黄波田新雁黄振元程霞董相姜雨杰
Owner DALI UNIV
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