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Dammarane triterpenoid glycoside compound as well as preparation method and application thereof

A kind of technology of dammarane triterpene sugar and compound, applied in the field of dammarane triterpene glycoside compound and preparation thereof

Active Publication Date: 2020-02-28
GUANGXI INST OF BOTANY THE CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report about the dammarane-type triterpene saponins contained in the Rubia plant Mycetia sinensis (Hemsl.) Craib and will be used as a sweetener

Method used

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  • Dammarane triterpenoid glycoside compound as well as preparation method and application thereof
  • Dammarane triterpenoid glycoside compound as well as preparation method and application thereof
  • Dammarane triterpenoid glycoside compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: the preparation of compound 1,2,3

[0040] 1) Get the extract

[0041] Weigh 1Kg of dry branches and leaves of Mycetia sinensis (Hemsl.) Craib (Guangxi sweet tea), crush them, add 8 times the weight of 95% (volume) ethanol, heat and reflux for 60 minutes to extract, filter, and collect the filtrate. Add 8 times the weight of 95% (volume) ethanol to the filter residue again, heat and reflux for 60 minutes to extract, and filter. The filtrates were combined, and the filtrate was concentrated to 2 L at 60° C. with a rotary evaporator under reduced pressure. Add 2 L of methanol to the concentrated solution, extract twice with petroleum ether, 2 L each time, collect the lower phase, recover the solvent from the petroleum ether phase and discard it, and rotary evaporate the lower phase to 2 L at 60°C to obtain the extract A001.

[0042] 2) Preliminary purification of the extract

[0043] Take the extract A001 and put it on the X-5 macroporous adsorption resin...

Embodiment 2

[0053] Embodiment 2: Structural characterization of compound 1

[0054] The white amorphous powder A003 of embodiment 1 gained is characterized:

[0055] Mycetioside II: white amorphous powder; UV(MeOH) λmax 190nm (terminal absorption); 1 H(500MHz) and 13 C (125MHz) NMR data are shown in Table 1; electrospray high resolution mass spectrometry (negative ion mode) HRESIMS m / z 799.4811[M-H]-, molecular formula C 42 h 72 o 14 , calculated value 799.4844, molecular weight 801.01, degree of unsaturation 7.

[0056] Table 1: The resulting white powder A003 1 H NMR and 13 C NMR data

[0057]

[0058]

[0059]

[0060] Therefore, it can be determined that the white powder obtained in Example 1 is compound 1, that is, dammatine II (hereinafter Mycetioside II), and its structure is shown in the following formula 1, and the structure is confirmed by NMR Selective-TOCSY, HSQC, and HMBC.

[0061]

Embodiment 3

[0062] Embodiment 3: Structural characterization of compound 2

[0063] The light yellow amorphous powder A007 obtained in Example 1 is characterized:

[0064] Mycetioside III: light yellow amorphous powder; UV(MeOH) λmax 190nm (terminal absorption); 1 H(500MHz) and 13 C (125MHz) NMR data are shown in Table 2; electrospray high resolution mass spectrometry (negative ion mode) HRESIMS m / z961.5407[M-H]-, molecular formula C 48 h 82 o 19 , calculated value 961.5450, molecular weight 963.15, degree of unsaturation 8.

[0065] Table 2: The resulting pale yellow powder A007 1 H NMR and 13 C NMR data

[0066]

[0067]

[0068]

[0069] Note: The solvent is deuterated methanol, the hydrogen spectrum is 500MHz, and the carbon spectrum is 125MHz.

[0070] Therefore, it can be determined that the yellow amorphous powder in Example 1 is compound 2, i.e. dammatine tea glycoside III (Mycetioside III), its structure is as shown in the following formula 2, and this structure ...

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Abstract

The invention discloses dammarane triterpenoid glycoside compounds as well as a preparation method and application thereof. The dammarane triterpenoid glycoside compounds are specifically three compounds which are separated from a rubiaceae rubia plant, namely Mycephala sinensis (Hemsl.) Craib, and the structural formula of the dammarane triterpenoid glycoside compounds is shown in the specification. Tests show that the dammarane type triterpenoid saponin with the structure shown in the formula 2 has sweetness, the sweetness of the dammarane type triterpenoid saponin is about 200 times that ofcane sugar, and the dammarane type triterpenoid saponin can be used as a sweetening agent and applied to various industries such as food and medicines.

Description

technical field [0001] The invention relates to active ingredients extracted and separated from plants, in particular to a dammarane triterpene glycoside compound extracted from Calyx sinensis, a Rubiaceae Rubia plant, and a preparation method and use thereof. Background technique [0002] Dammarane-type saponins belong to tetracyclic triterpenoid saponins, and are important characteristic bioactive components in precious Chinese medicinal materials such as ginseng, Panax notoginseng, American ginseng and Jiaogulan. Modern research shows that dammarane saponins have the functions of regulating immunity, anti-tumor, Anti-aging, anti-senile dementia, liver and kidney protection, anti-diabetes, anti-hyperlipidemia, anti-cardiovascular and cerebrovascular diseases, anti-neurodegenerative diseases, anti-osteoporosis, anti-depression and other pharmacological effects. At present, more than 200 kinds of naturally occurring dammarane-type triterpenoids have been found, distributed i...

Claims

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Application Information

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IPC IPC(8): C07J17/00A23L27/30
CPCA23V2002/00A23L27/36C07J17/005A23V2250/21
Inventor 谢运昌韦霄秦惠珍宁德生潘争红韦记青李典鹏
Owner GUANGXI INST OF BOTANY THE CHINESE ACAD OF SCI
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