Preparation method of norsesquiterpenoids in chimonanthus salicifolius

A technology of sesquiterpenoids and compounds, which is applied in the field of preparation of norsesquiterpenoids in Wintersweet, can solve the problems of small quantity and pharmacological activity research

Active Publication Date: 2021-06-08
JIAXING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The volatile oil components in Wintersweet are mainly composed of monoterpenes and sesquiterpenoids. Many studies have only reported the total volatile oil components and antibacterial and antioxidant activities in Wintersweet. The reported number of body sesquiterpenes is not much, and only 6 monomer nor sesquiterpenes have been reported, and their pharmacological activities have not been studied.

Method used

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  • Preparation method of norsesquiterpenoids in chimonanthus salicifolius
  • Preparation method of norsesquiterpenoids in chimonanthus salicifolius
  • Preparation method of norsesquiterpenoids in chimonanthus salicifolius

Examples

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Embodiment 1

[0035] The preparation of wax plum medicinal material and the extraction and separation of norsesquiterpene compounds 1 to 4 include forward and reverse phase column chromatography and high pressure liquid chromatography purification, which specifically adopts the following steps:

[0036] 1. The preparation of the medicinal material of Chimerus willow: dry the branches and leaves of Wintersweet willow, grind them, add 95% ethanol with a volume ratio of 1:3 to extract three times, and obtain the extracts of the branches and leaves after concentration. The extract of branches and leaves is dissolved in hot water, wherein the aqueous solution of extracts of branches and leaves is extracted three times with ethyl acetate, combined and concentrated to obtain ethyl acetate layer extract.

[0037] 2. Column chromatographic separation: the ethyl acetate extract was successively used MCI, and the eluent was methanol-water (50%-100% gradient elution), and a total of 4 parts were obtaine...

Embodiment 2

[0039] Structural identification of compound 1

[0040] Compound 1 is a new compound, and its structure was identified by means of modern techniques such as ESIMS and NMR. White amorphous powder. Low-resolution mass spectrometry ESI(+)MS gives molecular ion peak m / z 180.9[M+H] + , combined with NMR data to infer that its molecular formula is C 11 h 16 o 2 , with an unsaturation of 4. IR(KBr)ν max : 3412, 2970, 1656, 1617, 1040, 834cm -1 Indicates the possible presence of conjugated carbonyl and hydroxyl groups. 1 H-NMR (CDCl 3 , 400MHz, Table 1) The spectrum contains 1 pair of cis-alkene hydrogen δ H 6.75 (1H, d, J = 9.9Hz), 6.19 (1H, d, J = 9.9Hz), the methylene hydrogen (δ H 3.74,2H,m), 1 methylene (δ H 2.68, 2H, m), and 3 methyl hydrogens δ 1.25, 1.25, 1.92. 13 C-NMR (CDCl 3 , 100MHz, Table 1) contains 11 C atom signals, including 1 carbonyl (δ C 186.4), 2 double bonds (δ C 157.4, 157.2, 133.3, 125.9), a oxycarbon (δ C 61.0) and five other carbon signals ...

Embodiment 3

[0042] Compounds 2-4 are known compounds, compound 2 is robinlin, compound 3 is (3R, 6R, 7E)-3-hydroxyl-4,7-macrostigmadien-9-one ((3R, 6R, 7E)- 3-hydroxy-4,7-megastigmadien-9-one), and compound 4 is (+)-vomifoliol. Compound 2 is a colorless oil, ESI-MS m / z 199[M+H] + . 1 H-NMR (CDCl 3 , 400MHz) δ: 4.24 (1H, dd, J=14.1, 6.2Hz) 3.72 (1H, m, H-9a), 3.65 (1H, m, H-9b), 2.59 (1H, m, H-8a) , 2.48(1H, m, H-8b), 2.06(1H, dd, J=14.1, 6.2Hz, H-5a), 1.70(1H, t, J=14.1Hz, H-5b), 1.20(3H, s, CH 3 -10), 1.15 (3H, s, CH 3 -11); 13 C-NMR (CDCl 3 , 100MHz) δ: 200.1(C-1), 161.1(C-3), 129.4(C-2), 69.2(C-6), 60.7(C-9), 45.0(C-5), 37.3(C -4), 34.2 (C-8), 29.3 (C-11), 25.3 (C-10), 12.0 (C-7). Compound 3 is a colorless oil, ESI-MS m / z 209[M+H] + . 1 H-NMR (CDCl3 , 400MHz) δ: 6.53 (1H, dd, J=15.8, 10.0Hz, H-7), 6.09 (1H, d, J=15.8Hz, H-8), 5.63 (1H, brs, H-4), 4.27 (1H, brs, H-3), 2.49 (1H, d, J=10.0Hz, H-6), 2.26 (3H, s, CH 3 -10), 1.84 (1H, dd, J=13.4, 5.8Hz, H-2a), 1.62 (3H, s, CH 3...

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Abstract

The invention discloses a preparation method of norsesquiterpenoids in chimonanthus salicifolius, and particularly relates to the technical field of traditional Chinese medicine, the preparation method comprises the step of extracting and preparing norsesquiterpenoids from chimonanthus salicifolius which is a chimonaceae chimonanthus plant through a classic separation and purification means. The in-vitro experiments prove that the norsesquiterpenoids in the chimonanthus salicifolius have the activity of inhibiting staphylococcus aureus, bacillus subtilis and pseudomonas aeruginosa. The invention relates to discovery of a series of norsesquiterpenoids in chimonanthus salicifolius, including discovery of new compounds, which is new discovery of chemical components in chimonanthus salicifolius. The chimonanthus salicifolius norsesquiterpenoids extract and the monomeric compound thereof can be independently applied or combined or combined with a proper excipient, and can be prepared into oral or non-oral dosage forms according to a conventional method to be used as an antibacterial agent.

Description

technical field [0001] The embodiments of the present invention relate to the technical field of traditional Chinese medicines, and in particular to a preparation method of norsesquiterpenoids in Wintersweet. Background technique [0002] Willow-leaved wintersweet is a plant of the genus Wintersweetaceae, a semi-evergreen shrub, mainly distributed in Lishui (Liandu District, Yunhe, Jingning, Suichang, Songyang and other counties), Jiande, Kaihua and other places in Zhejiang Province. , there is also a small amount of distribution in Anhui, Jiangxi and other surrounding identities. Local people use the dried stems and leaves of willow-leaved wintersweet (she medicine famous food herbal tea) to decoct orally to treat colds, indigestion, abdominal pain and other diseases. Wintersweet contains terpenes, steroids, flavonoids, coumarins and alkaloids, which have antibacterial, anti-oxidant, anti-tumor, anti-alcoholic liver damage, anti-inflammatory, antidiarrheal, lipid-lowering ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/713C07C49/743C07C49/242C07C45/78C07C45/79C07C45/80A61P31/04
CPCC07C49/713C07C49/743C07C49/242A61P31/04C07C2601/16
Inventor 徐金标沈丽尧
Owner JIAXING UNIV
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