CN117659105A - Guaiane type sesquiterpene glycoside monomer compound and preparation method and application thereof - Google Patents

Guaiane type sesquiterpene glycoside monomer compound and preparation method and application thereof Download PDF

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Publication number
CN117659105A
CN117659105A CN202211027475.0A CN202211027475A CN117659105A CN 117659105 A CN117659105 A CN 117659105A CN 202211027475 A CN202211027475 A CN 202211027475A CN 117659105 A CN117659105 A CN 117659105A
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sesquiterpene
monomer compound
column chromatography
preparation
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管福琴
王奇志
李林蔚
陈雨
冯煦
印敏
单宇
刘飞
赵兴增
徐曙
王碧
田梅
李丕睿
冯博雅
赵万里
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C07H1/08—Separation; Purification from natural products
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

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Abstract

The invention discloses a novel sesquiterpene glycoside monomer compound, a preparation method and application thereof, belonging to the field of natural pharmaceutical chemistry. And a preparation method and application of the compound in the field of medicine, in particular to application in preparing hypoglycemic drugs or health care products.

Description

Guaiane type sesquiterpene glycoside monomer compound and preparation method and application thereof
1. Technical field:
the invention relates to the field of natural medicines, in particular to a novel sesquiterpene glycoside monomer compound secoisolariciresinol diglucoside A extracted and separated from rhizoma atractylodis lanceae, which has the chemical name: (1S, 5R,7R, 10R) -secoractroacetone 11-O-beta-D-glucopyranoside, its preparation method, its hypoglycemic activity and its application in preparing hypoglycemic medicine or health product.
2. Technical background:
type 2 diabetes is a chronic metabolic disease characterized by impaired islet beta cell function and reduced sensitivity to insulin of surrounding tissues (e.g., skeletal muscle, adipose tissue, and liver) due to impaired insulin signaling pathways. Thus, increasing insulin sensitivity and promoting glucose uptake by organ tissues is an important point of entry in the treatment of type 2 diabetes.
Rhizoma Atractylodis (Atractylodes lancea) is a perennial herb of Compositae, and its rhizome is used as a medicine. The atractylis lancea has warm nature, pungent and bitter taste, can dry dampness and invigorate spleen, dispel wind and remove cold, and improve eyesight, and is used for treating symptoms such as abdominal distention and pain, diarrhea, edema, rheumatalgia, common cold due to wind-cold, night blindness of sparrow eyes, and the like. The rhizoma atractylodis lanceae mainly contains a plurality of volatile oils, and the volatile oils account for about 5% -9%. The oil contains atractylol, atractylone, 3-beta-hydroxy atractylone, atractylenolide I, atractylenolide II, and atractylenolide III as main ingredients.
3. The invention comprises the following steps:
the invention aims to expand the sources of drugs for treating diabetes.
In order to achieve the aim, the invention extracts, separates and purifies the natural medicine monomer component secoisolariciresinol diglucoside A from the fresh rhizome of the rhizoma atractylodis lanceae, and is used for preparing the medicine for treating diabetes.
The chemical name of the secoisolariciresinol diglucoside A is (1S, 5R,7R, 10R) -secodactylo-delta-lactone 11-O-beta-D-glucopyranoside, and the chemical structural formula is as follows:
can be used for preparing hypoglycemic drugs or health care products.
The secoisolariciresinol diglucoside A is especially suitable for preparing a medicament for treating type 2 diabetes.
Furthermore, the secoisolariciresinol diglucoside A of the invention is also suitable for preparing medicines for treating diabetes complicated with inflammation.
The invention discloses a preparation method of secoisolariciresinol diglucoside A, which is characterized by comprising the following steps: the rhizome of Atractylodes lancea is used as a raw material, and after extraction by water or an organic solvent or a mixed solvent, the extracting solution is extracted by petroleum ether and ethyl acetate to obtain a petroleum ether layer, an ethyl acetate layer and a water layer. Adsorbing the water layer with macroporous resin, and separating 50% ethanol eluate by column chromatography. Wherein the macroporous resin comprises D101, AB-8, (or) HP-20; one or more of silica gel, alumina, polyamide and ODS for column chromatography; the organic solvent comprises methanol, ethanol or n-butanol; the extraction temperature is lower than 100 ℃.
Compared with the prior art, the invention has the following advantages:
1. the sesquiterpene glycoside monomer compound is purified from natural products for the first time, and the pharmacological activity of the sesquiterpene glycoside monomer compound in reducing blood sugar and resisting inflammation is obtained through pharmacological research.
2. The invention obtains a novel natural medicine with good blood sugar reducing activity, lays a foundation for subsequent further drug effect research, clinical research and guiding medicine taking, and expands the variety and sources of medicine for treating type 2 diabetes.
3. The sesquiterpene glycoside monomer compound has the effect of reducing blood sugar, can resist inflammation, and is more suitable for treating type 2 diabetes inflammation compared with the common hypoglycemic drugs.
4. The invention also researches the natural purification method of the sesquiterpene glycoside monomer compound, optimizes the preparation method of the compound with simple steps, larger yield and repeatability of preparation operation, and obtains the optimal purification method.
4. Description of the drawings:
the following figures may be reported as accessory materials.
FIG. 1 is a chemical structural formula of a sesquiterpene glycoside monomeric compound of the present invention;
FIG. 2 is a flow chart of the preparation of sesquiterpene glycoside monomeric compounds of the present invention;
FIG. 3 is a mass spectrum of a sesquiterpene glycoside monomeric compound of the present invention;
FIG. 4 is a hydrogen spectrum of a sesquiterpene glycoside monomer compound of the present invention;
FIG. 5 is a carbon spectrum of a sesquiterpene glycoside monomeric compound of the invention;
FIG. 6 is a HMBC spectrum of a sesquiterpene glycoside monomeric compound of the present invention;
FIG. 7 is a HMQC spectrum of a sesquiterpene glycoside monomer compound of the invention;
FIG. 8 is a ROESY spectrum of a sesquiterpene glycoside monomeric compound of the invention;
FIG. 9 is an ECD spectrum of a sesquiterpene glycoside monomer compound of the invention;
FIG. 10 is a graph showing the comparison of the hypoglycemic activity of the sesquiterpene glycoside monomeric compound of the present invention;
FIG. 11 is a graph comparing anti-inflammatory activity of sesquiterpene glycoside monomeric compounds of the present invention.
5. Detailed description of the preferred embodiments
The invention will be further illustrated with reference to specific examples, but the invention is not limited to the embodiments shown.
Example 1
Preparation example of secoisolariciresinol diglucoside A
As shown in fig. 2, the inventor performs cold leaching extraction on fresh rhizome of rhizoma atractylodis lanceae by using 95% ethanol, concentrates the extract to obtain an extract, and sequentially extracts the extract by using petroleum ether and ethyl acetate to obtain a petroleum ether part, an ethyl acetate part and a water part.
The water part is adsorbed by macroporous resin and then is eluted by a water-ethanol system in sections. And (3) combining 50% ethanol elution parts after high performance liquid detection and analysis, and concentrating to obtain the rhizoma atractylodis lanceae total extract.
The obtained rhizoma atractylodis total extract is subjected to silica gel column chromatography, and the mobile phase is chloroform-methanol-water (15:1:0.05- & gt 10:1:0.1- & gt 7:3:0.5- & gt 2:1:0.5- & gt methanol in sequence. Wherein chloroform-methanol-water (10:1:0.1) fraction is subjected to repeated reversed phase column separation and gel column purification to obtain sesquiterpene glycoside monomer compound.
And carrying out structural identification on the obtained compound.
White amorphous powder, easy to dissolve in methanol, ethanol and water, 254nm without dark spot under ultraviolet lamp, 365nm without fluorescence, TLC concentrated sulfuric acid-vanillin turns yellow. Positive Molish reaction; the acid hydrolysate gives D-glucose, data (fig. 3) displayed according to high resolution electrospray positive ion mass spectrometry (hresis): m/z [ M+Na] + 、[2M+Na] + 453.2067 ([ M+Na)] + Calculated values are 453.2101) and 883.4214, and the molecular formula is deduced to be C 21 H 34 O 9 Is sesquiterpene glycoside. At the position of 13 C-NMR(C 5 D 5 N,125MH Z ) In the spectrum (FIG. 5) there appears an acetyl group [ delta 29.7 (C-15), 211.2 (C-4)]An ester group [ delta 170.3 (C-3)]In addition, 8 oxygen-carbon nuclear signals such as delta 73.7 (C-14), delta 80.3 (C-11) and the like appear between the chemical shift values delta 60-110; 1 H-NMR(C 5 D 5 N,500MH Z ) Can be used in the spectrum (figure 4)It is evident (see Table 1) that 2 methyl groups attached to the tertiary carbon [1.16 (H 3 -12,s)、1.42(H 3 -13,s)]An acetylmethyl delta 2.30 (H 3 -15, s), 9 hydrogen nuclear proton signals of delta 5.03 (Glc H-1, d, j=7.7 Hz), 4.06 (m), 3.76 (dd, j=11.2, 11.3 Hz) etc. occur between the chemical shift values delta 3.5 to 5.3.
From the relevant signals in the nuclear magnetism and HSQC spectra (table 1) are available: comprising two methyl groups attached to a saturated quaternary carbon, five methylene groups (including one oxygen-linked methylene group), four methine groups, one oxygen-linked quaternary carbon, one acetyl group, one lactone carbonyl group, and one beta-D-glucopyranose residue. Combined with biogenic pathways and literature review, their nuclear magnetic data and (1S, 5R,7R, 10R) -atractylolide-11-O-beta-D-glucopyranoside (KITAJIMA et al, chemical&Pharmaceutical Bulletin,2003,51,152-157), and 13 when C-NMR data were compared, it was found that: the sesquiterpene glycoside has one less carbon nuclear signal with delta 91.4 in delta 60-110 region, one more carbon nuclear signal with delta 35.6, and the carbon nuclear signal delta 73.7 moves to 5ppm lower than the corresponding carbon nuclear signal delta 68.76, and is presumed to be a secoisolariciresinol derivative and forms hexatomic lactone after secoisolariciresinol.
The above was confirmed by remote correlation (see table 1) in HMBC spectra (fig. 6). H-1/C-2, C-4, C-5, C-9, C-10, C-14; h-2eq/C-1, C-3, C-10; H-5/C-1, C-2, C-4, C-6, C-7, C-10; H-10/C-8, C-14; h-14ax/C-1, C-3; h 3 C-4, C-5 demonstrates that the single bond between C-3 and C-4 breaks and that the C-3 ester group and C-14 form a six-membered lactone ring, suggesting that the sesquiterpene glycoside structure is shown in FIG. 1, designated as secoarthogonal atractyloid glycoside. The sugar end group proton signal (Glc H-1, δ5.03, d, j=7.7hz; glc C '-1δ98.8) was correlated remotely with 80.3 (C-11), inferring that C-11 was linked to glucose C-1'. The planar structure of the sesquiterpene glycoside is thus secotractylode 11-O-beta-D-glucopyranoside.
In the ROESY spectrum (FIG. 8), the correlation between H-1 and H-15 indicates that the configuration of H-1 and H-15 should be beta; and the correlation between H-10 and H-5,H-7 indicates that the configurations of H-5 and H-7 are α, respectively. Thus, the relative configuration of the sesquiterpene glycosides was determined as (1S, 5R,7R, 10R).
With the continuous progress of quantum chemical computing methods in recent years, ECD and experimental pattern comparison by computing organic compounds have become a reliable method for determining absolute configuration. The calculated ECD curves of (1S, 5R,7R, 10R) -secoatractylo-delta-lactate 11-O-beta-D-glucopyranoside are nearly identical to the experimental pattern, exhibiting positive Cotton effect at 216 and 287nm, respectively, and negative Cotton effect at 219nm (FIG. 9). Thus, the absolute configuration of the sesquiterpene glycoside was (1S, 5R,7R, 10R) and was named as secoisolariciresinol A (secoatractylohexone A), and the chemical name was (1S, 5R,7R, 10R) -secoractro-delta-lactone 11-O-beta-D-glucopyranoside. Searching the new split ring guaiane skeleton by a scibinder database.
TABLE 1 Total assignment of novel sesquiterpene glycosides Nuclear magnetic resonance data (delta, TMS, pyridine-d) 5 )
a Record on 125MHz
b Record on 500MHz
Application example 1
Blood sugar reducing efficacy study
Experimental animals: the study uses 40 (30-35 g) male C57BL/KsJ background Leprdb/Leprdb (db/db) mice (30-22 g) and 10 male wild type non-diabetic C57BL/KsJ Leprdb/+ (db/m) mice (6 weeks old) from Nanjing university model animal research center. In SPF barrier environment of Nanjing university of Chinese medicine (Nanjing, china) animal experiment center, 5 animals per cage were bred and tested in groups under alternating periods of light and dark at 22+ -2deg.C, 45-75% relative humidity and 12 hours. Free drinking and eating during the experiment. The study was conducted according to the "guidelines for laboratory animal administration and use" published by NIH in the united states (NIH publication No. 8023, revised 1978), and was approved by the institutional animal administration and use committee of the university of chinese medicine, south ky, china.
Grouping and administration: after 1 week of acclimation under control, db/db mice were randomly divided into 4 groups (10 per group) and physiological saline (db/db group) and low-dose SA were administered respectively 20 Group (administration of sesquiterpene glycoside monomer Compound of the invention 20 mg/kg/day, high dose group SA) 40 The group (40 mg/kg/day of administration of the sesquiterpene glycoside monomer compound of the invention), the positive drug Met group (150 mg/kg/day of administration of metformin), and the stomach was irrigated for 8 weeks. 10 db/m mice served as normal control group, db/m group was orally administered with the same dose of vehicle. During gastric lavage, dietary intake is not restricted. At the end of the experiment, the mice were fasted for 12 hours (free drinking water) and then sacrificed under anesthesia. And collecting a blood sample for detection.
Experimental results: as shown in FIG. 10, after 8 weeks of gastric lavage, the sesquiterpene glycoside compounds of the present invention were administered at a given dose (SA 20 Group 20 mg/kg/day and SA 40 Group 40 mg/kg/day) significantly reduced elevated blood glucose in db/db diabetic mice, and the administration group (SA 20 Group and SA 40 The group had significant differences (P) compared to the model group (db/db group)<0.001). The results show that the sesquiterpene glycoside compound of the invention has the function of reducing blood sugar.
Application example 2
Anti-inflammatory efficacy study
The anti-inflammatory efficacy of the sesquiterpene glycoside monomer compound of the invention is studied. Blood samples collected after group administration of experimental animals in application example 1 were used for detection.
Experimental results: as shown in FIG. 11, after 8 weeks of gastric lavage, the sesquiterpene glycoside compounds of the present invention were administered at a given dose (SA 20 Group 20 mg/kg/day and SA 40 Group 40 mg/kg/day) significantly reduced elevated inflammatory factors in plasma in db/db diabetic mice, and the group (SA 20 Group and SA 40 The group had significant differences (P) compared to the model group (db/db group)<0.001). The results show that the sesquiterpene glycoside compound has the function of reducing the inflammation level in the diabetic mice.

Claims (9)

1. A sesquiterpene monomer compound, secoatractylohexone A, characterized by the chemical name: (1S, 5R,7R, 10R) -secoractacto-delta-lactone 11-O-beta-D-glucopyranoside, the chemical structural formula is:
2. a process for preparing the compound of claim 1, characterized by using atractylis lancea as a raw material, extracting with water, methanol or ethanol; adsorbing the water layer of the extracting solution extracted by petroleum ether and ethyl acetate by macroporous resin; the macroporous resin is repeatedly separated and purified by silica gel column chromatography, sephadex LH-20 gel column chromatography, reversed-phase material ODS column chromatography and recrystallization means through the elution part of an alcohol-water system to obtain the compound.
3. The process according to claim 2, wherein the macroporous resin is D101, AB-8 or HP-20; the support for column chromatography is selected from one or more of silica gel, ODS and gel Sephadex LH-20.
4. The method of claim 2, wherein the extraction solvent is a lower alcohol having 1 to 4 carbon atoms and aqueous dilutions thereof, and further comprises chloroform, ethyl acetate, acetone, and mixtures thereof.
5. The pharmaceutical preparation prepared from the sesquiterpene monomer compound of claim 1 and pharmaceutically acceptable pharmaceutical excipients.
6. The pharmaceutical preparation according to claim 5, wherein the dosage form is a tablet, a capsule, an oral liquid, a granule or a freeze-dried powder injection.
7. The use of the sesquiterpene monomer compound according to claim 1 for preparing hypoglycemic drugs or health care products.
8. Use of the sesquiterpene monomer compound according to claim 1 for preparing a medicament for treating type 2 diabetes.
9. Use of a sesquiterpene monomer compound according to claim 1 for the preparation of a medicament for the treatment of diabetic inflammatory disease.
CN202211027475.0A 2022-08-25 2022-08-25 Guaiane type sesquiterpene glycoside monomer compound and preparation method and application thereof Pending CN117659105A (en)

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