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Vegeta tive female sex hormone eudesmane compound, and its preparing method and use

The technology of a compound, eucalyptus, is applied in the field of natural medicinal chemistry and chemotherapeutics, which can solve the problem of weakening the protective effect of progesterone

Active Publication Date: 2009-11-04
SHANGHAI JAHWA UNITED
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the protective effect of progestins appears to diminish with long-term use, and hormone replacement therapy (HRT) is thought to be associated with a 35-40% increased risk of breast cancer

Method used

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  • Vegeta tive female sex hormone eudesmane compound, and its preparing method and use
  • Vegeta tive female sex hormone eudesmane compound, and its preparing method and use
  • Vegeta tive female sex hormone eudesmane compound, and its preparing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Preparation and isolation of total extracts

[0032] The rhizome of Cyperus rotundus contains a variety of eucalyptane sesquiterpenes. The dried and crushed rhizome of Cyperus cyperi (1kg) was soaked in methanol at room temperature and extracted completely (3 days / time, 8L / time×3). Concentrate the extract under reduced pressure to obtain methanol extract (132g). The extract is distributed with water-ethyl acetate, and the ethyl acetate layer is concentrated to obtain 65g of extract. The ethyl acetate extract contains various eucalyptus sesquiterpene components. The ethyl acetate extract was applied to a silica gel column and eluted with petroleum ether-ethyl acetate (100:1-0:100) gradient to obtain two fractions, F-1 and F-2, respectively. Among them, F-1 (about 2 g) was purified by silica gel column chromatography to obtain eucalyptus-4,11-dien-3-one. F-2 (about 3g) was decontaminated by cross-linked dextran LH-20, and then separated by silica gel column chromatograp...

Embodiment 2

[0034] Separation and purification of norcine-4,6-diene-3,11-dione (4,6-Sueudesmadiene-3,11-dione).

[0035]

[0036] The ethyl acetate soluble part of the methanol extract of Rhizoma Cyperus was subjected to silica gel column chromatography, and the eluting part of petroleum ether-ethyl acetate (9:1) was taken, and impurities were removed by cross-linked dextran LH-20, and then purified by silica gel Repeated purification by column chromatography, eluting with petroleum ether-diethyl ether, gave a colorless oil. C 14 h 18 o 2 , HRESI[M+H] + m / z 219.1382, calculated 219.1385. [α] D +255°. Soluble in chloroform.

[0037] 1 H NMR (CDCl 3 , 400MHz): δ7.44 (1H, s, H-6), 2.43 (3H, s, H-12), 1.96 (3H, s, H-14), 1.10 (3H, s, H-13); 13 C NMR (CDCl 3 , 100MHz): 198.9(s, C-3), 198.8(s, C-11), 153.0(s, C-5), 143.1(s, C-7), 133.2(s, C-4), 132.4 (d, C-6), 36.3 (t, C-2), 36.2 (t, C-9), 33.9 (t, C-1), 33.1 (s, C-10), 25.8 (q, C- 12), 21.2 (q, C-13), 20.9 (t, C-8), 10.8 (q, C-...

Embodiment 3

[0039] Separation and Purification of Eudesmadieh-3-one (4,11-Eudesmadieh-3-one)

[0040] The ethyl acetate soluble part of the methanol extract of Rhizoma Cyperus was subjected to silica gel column chromatography, eluted with petroleum ether-ethyl acetate, and repeatedly purified to obtain a colorless oily substance. C 15 h 22 O, easily soluble in chloroform.

[0041] 1 H NMR (CDCl 3 , 400MHz): δ4.78 (2H, s, H-12), 2.74 (2H, q, J=1.7 Hz, H-6), 2.52 (2H, q, J=6.5Hz, H-2), 2.43 (2H, t, J=6.5Hz, H-2), 2.08(2H, d, J=8.9Hz, H-6), 1.78(6H, s, H-13, H-14), 1.24(3H, s, H-15).

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Abstract

The present invention provides salts, esters, and hydrates of eucalyptane compounds or derivatives thereof represented by the following formula (I): R in the formula represents hydrogen, hydroxyl, amino, halogen, carbonyl, or C1-6 alkyl, alkoxy , alkenyl, alkynyl, formyloxy, hydrazine, hydrazone, piperidine, pyridine, or various amino acid modified hydroxyl groups, or -SO2NHCOR groups. R2, R3, and R10 are hydrogen, carbonyl, terminal double bond, hydroxyl, halogen, or C1-6 alkyl, alkenyl, alkynyl, or alkoxy. R4 is hydrogen, hydroxy, methoxy, ethoxy or acetyl-protected hydroxy. R5, R6, R7, R9 are hydrogen, carbonyl, hydroxyl, methoxy, ethoxy, amino acid acyl, C1-6 alkoxy, alkyl or alkenyl. R8 is methyl, hydroxymethyl. The present invention also provides the preparation method of these compounds and their use in the preparation of medicines for the prevention and treatment of diseases caused by estrogen deficiency or sex hormone metabolism, especially disorders of estrogen metabolism regulation, as well as their use in the preparation of cosmetics .

Description

technical field [0001] The invention relates to the fields of natural medicinal chemistry and chemotherapeutics, in particular to the preparation of eucalyptus compounds and their use in the prevention and treatment of diseases caused by estrogen deficiency or sex hormone metabolism, especially estrogen metabolism regulation disorders. Background technique [0002] Women experience irregular menstrual cycles around age 40, which marks the onset of menopause. This period of endocrine system changes is called menopause, and it can last a decade or more. It is the result of failure of follicular growth and decreased response to gonadotropins. The result of the lack of follicles is that the production of estrogen decreases and eventually stops completely. Various symptoms may accompany it, such as hot flashes, depression, anxiety, confusion, insomnia, etc. In addition to this, decreased estrogen production may cause serious health problems such as osteoporosis, cardiac insuff...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/67C07C49/733A61K31/122A61K8/35A61K8/37A61P35/00A61P13/08A61P19/10A61P25/28A61P9/10A61P3/06A61Q19/08
Inventor 赵亚魏少敏胡昌奇
Owner SHANGHAI JAHWA UNITED
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