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Natural sweeteners oleanane-type triterpenoid saponin compounds as well as preparation methods and application thereof

A kind of technology of triterpenoid saponins and oleanane type, applied in the field of sweetener and natural medicinal chemistry, can solve the problems such as unreported

Active Publication Date: 2016-07-06
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with the research on pharmacological activity, there are few researches on the chemical constituents of Deerwort trichome at home and abroad, and only 3 new and 2 known triterpenes isolated and identified from Deerwort trichome have been reported: Triterpenoid A (eriocarpinA), eriocarpin B (eriocarpinB), eriocarpin C (eriocarpinC), 2β, 3β, 28‐trihydroxy‐12‐en‐oleane, β‐amyrin, and heptacyl Fatty acid glycerides and β-sitosterol, but there are no reports of active compounds in this plant

Method used

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  • Natural sweeteners oleanane-type triterpenoid saponin compounds as well as preparation methods and application thereof
  • Natural sweeteners oleanane-type triterpenoid saponin compounds as well as preparation methods and application thereof
  • Natural sweeteners oleanane-type triterpenoid saponin compounds as well as preparation methods and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Extraction, separation and purification of the sweet total saponins extract of Deeris trichocarpa and compounds 1-4 of the present invention:

[0040] Instruments and materials:

[0041] Specific rotation was measured by HoribaSEPA‐300 spectrophotometer, UV was measured by ShimadzuUV‐2401A UV spectrometer, IR was determined by BruckerTenor‐27 infrared spectrometer, ESI‐MS and MS‐MS were determined by BrukerHCT / Esquire mass spectrometer, NMR Measured by Bruker AM-400, DRX-500, AvanceⅢ600 nuclear magnetic resonance instrument, TMS as internal standard, the unit of chemical shift value δ is ppm, and the unit of coupling constant J is Hz.

[0042] Various types of silica gel column chromatography columns, reverse-phase medium pressure columns, rotary evaporators (BüCHI and EYELA companies), dark box UV analyzers (Shanghai Jiapeng Technology Company), medium pressure liquid chromatography (BüCHI), oil Bath thermostat.

[0043] Normal-phase silica gel plate (Qingdao Ocean C...

Embodiment 2

[0050] Physical and spectral data of compound 1-4 of the present invention:

[0051] MillettiasaponinA (1): white powder, 1 HNMR and 13 CNMR data are shown in Table 1 and Table 2; ESI-MS + (m / z1015,[M+H] + ;1037,[M+Na] + ;1059, [M+2Na‐H] + ; 1075, [M+Na+K‐H] + ), ESI‐MS ‐ (m / z1013,[M-H] ‐ ).

[0052] DerrisaponinA (2): white powder, UV(H 2 O)λ max (nm)(logε):190(3.74); IR(KBr)ν max cm ‐1 :3423(OH),2972,2934,1713,1615,1265,1074,1048; 1 HNMR and 13 See Table 1 and Table 2 for CNMRdata; ESI‐MSm / z1175[M‐H] ‐ ;HR‐EI‐MSm / z1175.5480,[M] ‐ (C 56 h 88 o 26 The calculated value is 1175.5480).

[0053] DerrisaponinB (3): white powder, UV(H 2 O)λ max (nm)(logε):190(3.77); IR(KBr)ν max cm ‐1 :3424(OH),2969,2932,1718,1615,183,1261,1072,1048; 1 HNMR and 13 See Table 1 and Table 2 for CNMR data; ESI‐MSm / z1175[M‐H] ‐ ,1013[M‐162] ‐ ;HR‐EI‐MSm / z1175.5482,[M] ‐ (C 56 h 88 o 26 The calculated value is 1175.5482).

[0054] Derrisaponin C (4): white powder, UV(...

Embodiment 3

[0065] Taste threshold and sweetness test of oleanane-type triterpene saponins 1-4 of the present invention:

[0066]Sweetness evaluation of a single compound: prepare sucrose reference solution gradients with concentrations of 4%, 2%, and 1%, and sample solution gradients with concentrations of 0.02%, 0.01%, 0.005%, 0.0033%, 0.0025%, and 0.002%. The sweetness threshold and sweetness of the samples were evaluated by the evaluation team members. The threshold value refers to the lowest concentration that can taste sweetness (unit: mg / ml); the sweetness refers to the multiple of the sweetness of the sample to the sweetness of sucrose, which is found by comparing the sweetness of a certain concentration of sample with a certain concentration of sucrose The sweetness is equivalent, thereby converting the sweetness of the sample. The taste threshold and sweetness of oleanane-type triterpene saponins 1-4 are shown in Table 3.

[0067] Table 3 Sweetness evaluation of compounds 1-4 ...

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Abstract

The invention provides oleanane-type triterpenoid saponin compounds as shown in the structural formula (I). In the structural formula (I), R1 represents alpha-L-rhamnose-(1->2)-alpha-D-galactose-(1->2)-beta-D-glucuronic acid, or beta-D-glucose-(1->3)-[alpha-L-rhamnose-(1->2)]-alpha-D-galactose-(1->2)-beta-D-glucuronic acid; R2 is replaced by glucose or hydrogen. The invention further provides combinations of the oleanane-type triterpenoid saponin compounds, plant extracts containing the oleanane-type triterpenoid saponin compounds, preparation methods of the oleanane-type triterpenoid saponin compounds, the oleanane-type triterpenoid saponin compounds and the plant extracts, and application of the oleanane-type triterpenoid saponin compounds, the plant extracts and the compositions to the field of sweeteners. Researches on folk characteristic medicinal plants in Yunnan show that the sweetness of Dai medicine derris eriocarpa How. is obvious; via gustation activity-guided isolation, the oleanane-type triterpenoid saponin compounds of high sweetness are separated from derris eriocarpa How.

Description

Technical field: [0001] The invention belongs to the field of sweeteners and natural medicinal chemistry, and in particular relates to a new class of sweet oleanane-type triterpene saponins, derivatives thereof, organic and inorganic acid salts, compositions containing them and fur Sweet extracts (sweet total saponins) of deer vine, their preparation methods, and their use in food or beverages. Background technique: [0002] For various reasons, sweetness plays a central role in the five basic taste sensations that humans can perceive, including sweetness, umami, bitterness, saltiness, and sourness. Sweet substances are called sweeteners. Sweeteners are divided into sugar sweeteners (such as sucrose, glucose, maltose, fructose, etc.) Such as saccharin, aspartame, acesulfame potassium, sucralose, etc.) and natural sweeteners. [0003] In the long-term application history, many diseases with high incidence in human beings, such as diabetes, cardiovascular disease, obesity, h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00C07H15/256C07H1/08A23L27/30A23L2/60
CPCA23L2/60A23V2002/00C07H1/08C07H15/256C07J63/00A23V2250/21
Inventor 杜芝芝张红霞李志坚
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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