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Anthraquinone compound, and preparation method and application thereof

A compound, anthraquinone technology, applied in the field of phytochemistry, can solve problems such as no relevant reports, achieve good antioxidant activity, easy to implement, and prolong the shelf life

Active Publication Date: 2017-09-05
CHINA TOBACCO YUNNAN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention isolates an anthraquinone compound with good antioxidant activity from aloe vera, and no relevant reports have been seen on the compound and its application in inhibiting the deterioration of essential oils

Method used

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  • Anthraquinone compound, and preparation method and application thereof
  • Anthraquinone compound, and preparation method and application thereof
  • Anthraquinone compound, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0038] The aloe sample was collected in Yuanjiang, Yunnan. 3.5kg of dried aloe was taken, coarsely crushed to 30 mesh, ultrasonically extracted with 70% acetone for 4 times, 60 minutes each time, and the extracts were combined; the extracts were filtered and concentrated under reduced pressure to 1% of the volume. / 4; leave standstill, filter out the precipitate, and concentrate into 110g of extract; add 250g of acetone to dissolve in the extract, then add 100 mesh silica gel 120g to mix the sample, after mixing the sample, pack the column with 200 mesh silica gel 600g; The volume ratios were 1:0, 9:1, 8:2, 7:3, 1:1, and 0:1 for gradient elution with chloroform-acetone mixed organic solvents, and the gradient eluate was collected, concentrated, and monitored by TLC. Merge the same parts to get 6 parts A-F, among them, for the collected sample D (7:3) part 18g, then use 48% methanol as mobile phase, flow rate 20ml / min, 21.2×250mm, 5μm Zorbax PrepHT The GF reversed-phase prepara...

Embodiment 2

[0040] The aloe sample was collected in Hekou, Yunnan Province, and 4.2kg of dried aloe was taken, coarsely crushed to 35 mesh, ultrasonically extracted 4 times with 70% acetone, 50 minutes each time, and the extracts were combined; the extracts were filtered and concentrated under reduced pressure to 1% of the volume. / 4; leave standstill, filter out the precipitate, and concentrate into 136g of extract; add 280g of acetone to dissolve in the extract, then add 100 mesh silica gel 140g to mix the sample, after mixing the sample, pack the column with 200 mesh silica gel 900g; The volume ratios were 1:0, 9:1, 8:2, 7:3, 1:1, and 0:1 for gradient elution with chloroform-acetone mixed organic solvents, and the gradient eluate was collected, concentrated, and monitored by TLC. Merge the same parts to get 6 parts A-F, among them, for the collected sample D (7:3) part 22g, then use 48% methanol as mobile phase, flow rate 20ml / min, 21.2×250mm, 5μm Zorbax PrepHT The GF reversed-phase pr...

Embodiment 3

[0042] The structure of the anthraquinone compounds prepared in Example 1 is determined by the following method; the compound is a red jelly; HRESI-MS shows that its quasi-molecular ion peak is 335.0887[M+Na] + (calculated value 335.0895), combined with 1 HNMR and DEPT spectra confirmed that its molecular formula is C 18 h 16 o 5 , with an unsaturation of 11. The hydroxyl group (3407cm ‐1 ), carbonyl (1662cm ‐1 ) and aromatic rings (1617, 1554 and 1448cm ‐1 ) resonance absorption peak. The UV spectrum has maximum absorption at 210, 248, 276 and 407nm, which also shows that there may be an aromatic ring structure in the compound. compound 1 H and 13 The C NMR spectrum (Table-1) shows that it contains 17 carbons and 14 hydrogens, including two benzene rings (C1-C8, C-1a, C-4a, C-9a and C-10a; H-1, H -4, H-7 and H-8), two carbonyl groups (C-9 and C-10), one hydroxyethyl group (C-12 and C-13; H 2 ‐12 and H 2 ‐13), a methyl group (C‐11; H 3 ‐11), a methoxy group (δ C ...

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Abstract

The invention discloses an anthraquinone compound, and a preparation method and application thereof. The anthraquinone compound is separated from aloe; the molecular formula of the anthraquinone compound is C18H16O5; the structural formula of the anthraquinone compound is as described in the specification; and the anthraquinone compound is named as 3-hydroxy-6-hydroxyethyl-5-methoxy-2-methyl-anthraquinone. The anthraquinone compound is prepared from aloe through extraction of extract, column chromatography on silica gel and high-pressure liquid chromatographic separation. Experimental results show that the compound has good antioxidation activity and free-radical removal activity; and when applied as an anti-oxidant for flavoring essential oil of a cigarette, the compound can effectively inhibit oxidation deterioration of the flavoring essential oil and substantially prolonging the shelf life of the cigarette without any influence to the smoking quality of the cigarette.

Description

technical field [0001] The invention belongs to the technical field of phytochemistry, and in particular relates to an anthraquinone compound extracted from plant aloe for the first time, and the compound has good antioxidant activity. At the same time, the invention also relates to the preparation method of the compound and the application of the compound in inhibiting the oxidative deterioration of cigarette flavoring essential oil. Background technique [0002] Aloe (scientific name: Aloe vera), belonging to the genus Aloe, is a perennial evergreen herb of the family Liliaceae. Aloe vera is native to the Mediterranean and Africa. It is easy to grow and is an ornamental plant with both flowers and leaves. It is very popular among the public. According to research, there are more than 300 wild aloe varieties, and there are six edible varieties. The main aloe varieties with medicinal value are: foreign aloe, Curacao aloe, Cape of Good Hope aloe, Yuanjiang aloe and so on. A...

Claims

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Application Information

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IPC IPC(8): C07C46/10C07C50/34A24B3/12
CPCA24B3/12C07C46/10C07C50/34
Inventor 孔维松李雪梅张承明米其利耿永勤陈建华刘欣李晶许永蒋微李干鹏王明锋者为周敏胡秋芬杨光宇
Owner CHINA TOBACCO YUNNAN IND
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