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Eucalyptus sesquiterpene compounds as well as pharmaceutical composition, preparation method and application thereof

A technology of compounds, drugs, applied in the field of natural medicinal chemistry

Active Publication Date: 2019-06-21
DALI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there are no preparation methods of eucalyptane sesquiterpene, eucalyptane sesquiterpene dimer, and noreucalyptane sesquiterpene compounds in the genus Cochina, and no drug combination with these compounds as active ingredients. and its application in antimalarial

Method used

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  • Eucalyptus sesquiterpene compounds as well as pharmaceutical composition, preparation method and application thereof
  • Eucalyptus sesquiterpene compounds as well as pharmaceutical composition, preparation method and application thereof
  • Eucalyptus sesquiterpene compounds as well as pharmaceutical composition, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0110] Extraction, separation and purification of compound 1-68 of the present invention:

[0111] Dry the rhizomes (19 kg) of the genus Chiapodium in the shade, crush them to 30 meshes, extract them three times with 95% methanol at room temperature, 70 L each time for 24 hours, combine the extracts, and concentrate the extracts under reduced pressure to obtain Suspend the extract with an appropriate amount of water, and distribute it several times with ethyl acetate to obtain an ethyl acetate extract (1.5 kg). The extract is dissolved in an appropriate amount of chloroform / acetone and mixed with silica gel 80-100 mesh, and then mixed with 650 G silica gel 200-300 mesh was used for column chromatography, and the gradient elution was carried out with chloroform / acetone (1 : 0-0 : 1), and 8 main parts were obtained. The pure chloroform part, 9: 1 chlorine / acetone Silica gel column chromatography, 8 : 2 chlorine / C fraction and 7 : 3 chlorine / C fraction were carried out by gra...

Embodiment 2

[0113] Physical and spectral data of compounds 1, 9, 22, 30, 36, 43, 48, 54, 61 of the present invention:

[0114] Compound 1: Pale yellow gum. HR-ESI-MS m / z : 331.1917 [M-H] - (calcd. for C 20 h 27 o 5 331.1915); [α] D 25 0 ( c = 0.085, MeOH); 1 H-NMR (400 MHz, CD 3 COCD 3 ) δ : 6.97 (1H, s,H-12), 5.95 (1H, qd, J = 7.2, 1.4 Hz, H-3'), 4.64 (1H, dd, J = 11.4, 4.2 Hz,H-3), 2.59 (1H, dd, J = 15.8, 4.7 Hz, H-6), 2.23 (2H, q, J = 15.4 Hz, H-9), 2.12 (1H, overlap, H-6), 1.85 (3H, dd, J = 7.2, 1.6 Hz, H-4'), 1.79 (3H, d, J = 1.3 Hz, H-13), 1.76 (3H, t, J = 1.6 Hz, H-5'), 1.71 (1H, m, H-2), 1.62 (1H,dd, J = 11.7, 4.5 Hz, H-5), 1.56 (1H, overlap, H-1), 1.50 (1H, overlap, H-2),1.46 (1H, overlap, H-1), 1.20 (3H, s, H-15), 0.80 (3H, s, H-14); 13 C-NMR (100MHz, CD 3 COCD 3 ) δ : 39.2 (t, C-1), 26.2 (t, C-2), 81.7 (d, C-3), 74.1 (s, C-4), 51.0 (d, C-5), 18.1 (t, C-6), 117.1 (s, C-7), 149.7 (s, C-8), 42.7 (t, C-9), 35.7 (s, C-10), 120.2 (s, C-11), 138.0...

Embodiment 3

[0145] Antimalarial activity detection of compounds of the present invention:

[0146] Using the internationally accepted 4-day inhibition test method, each mouse was inoculated intraperitoneally with 1×10 7 Plasmodium-infected red blood cells were given intragastric administration 3 hours after inoculation with Plasmodium, and then administered once every 24 hours for 4 consecutive days (the inoculation day was D 0 , the next day is D 1 , and so on), on day 5 (D 4 ) blood from the tail vein, coated with a thin blood film, fixed in methanol, stained with Wright-Giemsa mixed staining method, and observed under a 10×100 oil microscope. If no Plasmodium asexual body is found after randomly checking 50 fields of view, it is judged as negative, and the positive thin blood film is randomly counted in 5 fields of view, and the total number of red blood cells is not less than 1000, and then the inhibition rate of Plasmodium is calculated according to the following formula .

[014...

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Abstract

The invention relates to eucalyptus sesquiterpene compounds as well as a pharmaceutical composition, a preparation method and application thereof and belongs to the field of natural pharmaceutical chemistry. The pharmaceutical composition takes the compounds in formulas (1)-(IX) as an active ingredient; the preparation method of the eucalyptus sesquiterpene compounds comprises the following steps: taking roots or a rhizomes or whole plants of dobinea plants of anacardiaceae, directly performing cold immersion or thermal reflux or ultrasonic or microwave assisted extraction with organic solvent petroleum ether or chloroform or ethyl acetate or acetone or methanol or ethanol or water or then extracting with the ethyl acetate to obtain a total extract after cold immersion or thermal reflux or ultrasonic or microwave assisted extraction with the organic solvent or the water; obtaining the compounds after the total extract is subjected to repeated chromatography. The anti-malarial pharmaceutical composition takes the compounds as the active ingredient. The compounds provided by the invention are applied to the preparation of anti-malarial agents.

Description

[0001] Technical field: [0002] The invention belongs to the field of natural medicinal chemistry, and in particular relates to a new class of eucalyptane sesquiterpenoids, a preparation method thereof, a drug combination with the compounds as active ingredients, and an antimalarial application thereof. [0003] technical background: [0004] Nine children ( Dobinea ) plants belong to Anacardiaceae or Podoaceae, and are shrubs or perennial subshrub-like herbs with hypertrophic rhizomes. There are 2 species in the world, Gastrodia chinensis ( Dobinea delavayi (Baill.) Baill.) and Gongshan Jiuzimu ( D. vulgaris Buch.-Ham. ex D. Don), all produced in my country. Gastrodia chinensis is a perennial subshrub-like herb with thick rhizomes. It is named after it is shaped like a horn after processing; it is produced in the central to northwestern part of Yunnan and southwestern Sichuan; it grows in sunny grass slopes or shrubs at an altitude of 1100-2300 meters . Folks are used...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/92C07C69/533C07C69/716C07C69/56C07C69/18C07C69/757C07C69/16C07C69/78C07C229/34C07C67/48C07C227/40A61K31/343A61K31/365A61K31/22A61K31/221A61K31/235A61P33/06
CPCY02A50/30
Inventor 姜北肖朝江沈怡崔淑君陈浩沈磊董相王敏
Owner DALI UNIV
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