CN109810153A - Fragrance replaces the preparation method of glucose compounds and its pharmaceutical composition and analgesia to apply - Google Patents

Fragrance replaces the preparation method of glucose compounds and its pharmaceutical composition and analgesia to apply Download PDF

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CN109810153A
CN109810153A CN201910275661.8A CN201910275661A CN109810153A CN 109810153 A CN109810153 A CN 109810153A CN 201910275661 A CN201910275661 A CN 201910275661A CN 109810153 A CN109810153 A CN 109810153A
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compound
overlap
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CN109810153B (en
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姜北
肖朝江
李骅轩
沈磊
董相
王敏
江世智
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Dali University
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Abstract

The present invention relates to fragrance, and the preparation method of glucose compounds and its pharmaceutical composition and analgesia to be replaced to apply, and belongs to field of natural medicinal chemistry.Formula (I) fragrance replaces glucose compounds, using such compound as the pharmaceutical composition of active constituent, preparation method, take aerial part or the complete stool of Ternstroemia gymnanthera plant, with organic solvent dichloromethane or chloroform or ethyl acetate or acetone or methanol or ethyl alcohol or the direct cold soaking of water or heat reflux or the assisted extractions such as ultrasound or microwave, either first with above-mentioned organic solvent or water cooling soak or reflux or the assisted extractions such as ultrasound or microwave after be extracted with ethyl acetate to obtain total medicinal extract again, total medicinal extract through chromatographing to obtain the compound of the present invention repeatedly.Using the compounds of this invention as the analgesic medical compounds of active constituent.The compounds of this invention is preparing the application in analgestic.

Description

Fragrance replaces the preparation method and analgesia of glucose compounds and its pharmaceutical composition Using
Technical field:
The invention belongs to field of natural medicinal chemistry, and in particular, to a kind of fragrance replaces glucose compounds, preparation side Method, using such compound as the pharmaceutical composition of active constituent, and its application in analgesia.
Technical background:
Ternstroemia gymnanthera [Ternstroemia gymnanthera(Wight et Arn.) Bedd.] different name nakedanther ternstroemia leaf flower and fruit, weighing lever be red, not It is red cut, camellia tree, pig blood bavin, qi and blood rattan, big five tastes rattan etc., be Theaceae Ternstroemia gymnanthera category shrub or dungarunga, it is high by 1.5~10 Rice, sometimes up to 15 meters.It is distributed widely in Xiuning, Zhejiang, Jiangxi, Fujian, the Hubei west and south, Southern Hunan of China's Southern Anhui Province It is more with the ground such as the Bijie of the northwestward, Guangdong, In Northern Guangxi and east, Yunnan, Northeastern Guizhou and the northwestward and South Sichuan It is born in the mountainous region woods of 200~1400 meters of height above sea level (Yunnan can be distributed in 2000~2800 meters), border roadside or nearly mountain top sparse woods In.The leaf and complete stool that " China's book on Chinese herbal medicine " etc. records Ternstroemia gymnanthera have the effect of clearing heat and detoxicating, eliminating stasis to subdue swelling.Cure mainly sore and toxic and Acute mastitis；And the flower energy desinsection of the plant is antipruritic, can be used for treating scabies itch.Currently, there is document report Japan to produce in Ternstroemia gymnanthera Main component is triterpene compound, and a small amount of simple phenolic acid compound of structure (Tori M, et al.Letters in Organic Chemistry, 2005,2(3): 262-264；Ikuta A, et al.Journal of Natural Products, 2003,66(8): 1051-1054.).But have no that fragrance replaces glucose in related Ternstroemia gymnanthera both at home and abroad so far Class compound and its analgesic activities research report.
Summary of the invention:
The present invention is intended to provide a kind of fragrance replaces glucose compounds, using it as the pharmaceutical composition of active constituent, they Preparation method and they preparing the application in analgestic.
Above-mentioned purpose of the invention is achieved by following technical solution:
The following general formula (I) compound,
。
R in logical formula (I)1、R2、R3、R4And R5Representative group is selected from hydrogen (- H) or following structure fragment:
；
X and Y is hydrogen (- H), hydroxyl (- OH) or methoxyl group (- OCH3).
The fragrance of above-mentioned logical formula (I) replaces glucose compounds, preferably takes following compounds 1-19:
。
The preparation method of formula (I) compound, take Theaceae Ternstroemia gymnanthera [Ternstroemia gymnanthera(Wight Et Arn.) Bedd.] plant aerial part or complete stool, with organic solvent dichloromethane or chloroform or ethyl acetate or acetone Or methanol or ethyl alcohol or the direct cold soaking of water or heat reflux or ultrasound perhaps assisted extractions such as microwave or first with above-mentioned organic It is extracted with ethyl acetate to obtain total medicinal extract again after solvent or water cooling leaching or reflux or the assisted extractions such as ultrasound or microwave, it is total to soak Cream chromatographs to obtain formula (I) compound through column repeatedly.
The preparation method of formula (I) compound of the invention is more specifically used:
A: methylene chloride or chloroform or ethyl acetate or acetone or methanol or ethyl alcohol or the direct cold soaking of water or heat reflux or super The assisted extractions such as sound or microwave Ternstroemia gymnanthera [Ternstroemia gymnanthera(Wight et Arn.) Bedd.] plant Aerial part or complete stool obtain total medicinal extract, ethyl acetate extract is obtained by extraction in ethyl acetate, through column repeatedly chromatography formula can be obtained (I) compound.
B: organic solvent (such as: chloroform, methanol, ethyl alcohol, acetone, methylene chloride) directly cold soaking or heat reflux or ultrasound Or the assisted extractions such as microwave Ternstroemia gymnanthera [Ternstroemia gymnanthera(Wight et Arn.) Bedd.] plant Aerial part or the coarse powder of complete stool obtain total medicinal extract, and formula (I) compound can be obtained through the chromatography of column repeatedly in total medicinal extract.
More specifically, the preparation method of formula (I) compound, be by Ternstroemia gymnanthera [Ternstroemia gymnanthera (Wight et Arn.) Bedd.] plant aerial part or complete stool dry in the shade, 20-30 mesh is crushed to, with 95% ethyl alcohol in room temperature item Extract 3 times under part, every time 24 h, extracting solution merges, and is concentrated under reduced pressure after extracting solution obtains medicinal extract and is suspended with suitable quantity of water, then with acetic acid second Ester distributes for several times, obtains acetic acid ethyl ester extract, mixes sample with silica gel 80-100 mesh after the appropriate Lv Fang ∕ acetone solution of extract, so Column chromatography is carried out with 200-300 mesh silica gel afterwards and draws section rough segmentation, with 1: 0-0: 1 Lv Fang ∕ acetone or 1: 0-0: 1 Lv Fang ∕ Methanol carries out gradient elution, 7 major parts is obtained, by 9: 1 Lv ∕ first parts, 8: the 2 ∕ first parts Lv and 7: 3 Lv ∕ first Part carries out silica gel column chromatography, carries out gradient elution with 100: 1-1: 1 Lv Fang ∕ acetone, obtains 10 parts, then carry out respectively Silica gel, RP-18 and Sephadex LH-20 column chromatography obtain formula (I) compound respectively repeatedly.
Analgestic contains any compound and conventional adjuvant in formula (I) compound.
Pharmaceutical composition, wherein any compound and pharmaceutically acceptable in the formula (I) compound containing therapeutically effective amount Carrier.
Any compound is preparing the application in analgesic in formula (I) compound.
The present invention is used for analgesic pharmaceutical composition, wherein containing any compound in formula (I) compound and pharmaceutically may be used The carrier of receiving.
Pharmaceutically acceptable carrier described in pharmaceutical composition of the present invention refers to the pharmaceutical carrier of pharmaceutical field routine.This Invention compound can be applied to by way of oral, nasal inhalation, rectum or parenteral administration in the form of compositions needs this The patient of kind treatment.When for taking orally, it can be made into conventional solid pharmaceutical preparation such as tablet, pulvis, granula, capsule etc., be made Liquid preparation such as oil-suspending agent, syrup, elixir etc.；When for parenteral administration, the solution etc. of injection can be made into.Preferably Form is tablet, capsule and injection.
The various dosage forms of pharmaceutical composition of the present invention can be prepared according to the conventional production process of pharmaceutical field.Such as make to live Property ingredient is mixed with one or more carriers, is then made into required dosage form.
Pharmaceutical composition of the invention preferably comprises the active constituent that weight ratio is 0.1% -99.5%, most preferably weight Than the active constituent for 0.5% -95%.
The amount of application of the compounds of this invention can be according to route of administration, the age of patient, weight, the type for the disease treated Change with severity etc., daily dose can be 0.01-10 mg/kg weight, preferably 0.1-5 mg/kg weight.It can be primary Or multiple applications.
The compound of the present invention shows preferable analgesic activities.
The present invention has carried out analgesic activities screening to compound 1-19, such compound shows preferable analgesic activities.? In analgesic activities application, compound 1-19 is applied on substrate or a population with following amount, the range 1-1000 of the amount μM, preferably at 10-200 μM, optionally combined with carrier and/or media.
Specific embodiment:
Essentiality content of the invention is further illustrated with the embodiment of the present invention below, those skilled in the art can be made more comprehensively Ground understands the present invention, but do not limit the invention in any way.
Embodiment 1:
The extracting and developing of the compounds of this invention 1-19 and purifying:
By Ternstroemia gymnanthera [Ternstroemia gymnanthera(Wight et Arn.) Bedd.] plant aerial part (14 Kg it) dries in the shade, is crushed to 30 mesh, extracted at room temperature 3 times with 95% ethyl alcohol, 60 L, 24 h, extracting solution merge every time, decompression Concentrated extracting solution is suspended after obtaining medicinal extract with suitable quantity of water, then is distributed 6 times with ethyl acetate, is obtained acetic acid ethyl ester extract (726 g), is extracted It takes and mixes sample with silica gel 80-100 mesh after the appropriate Lv Fang ∕ acetone solution of object, then carry out column layer with 650 g silica gel 200-300 mesh Section rough segmentation is drawn in analysis, is carried out gradient elution with Lv Fang ∕ methanol (1: 0-0: 1), 7 major parts is obtained, by 9: 1 Lv ∕ first Partially, 8: the 2 ∕ first parts Lv and 7: the 3 ∕ first parts Lv carry out silica gel column chromatography, with 100: 1-1: 1 Lv Fang ∕ acetone into Row gradient elution obtains 10 parts.Carry out repeatedly silica gel respectively again, RP-18 and Sephadex LH-20 column chromatographs to obtain compound 1-19。
Embodiment 2:
The physics and spectroscopic data of the compounds of this invention 1-19:
Compound 1: brown solid.UV(MeOH)λ max(logε): 223(4.12), 291(3.58) nm；HR-ESI-MSm/z: 315.1405 [M-H]-(calcd for C14H19O8, 315.1402)；1H-NMR(400 MHz, CD3OD)δ: 6.62(1H, d,J =2.1 Hz, H-2 '), 6.61(1H, d,J =8.1 Hz, H-5 '), 6.49(1H, dd,J =8.0,2.1 Hz, H-6 '), 4.23(1H, d,J =7.8 Hz, H-1), 3.96(1H, m, H-8 ' a), 3.80(1H, dd,J =11.9,1.9 Hz, H-6a), 3.62(2H, overlap, H-6b, 8 ' b), 3.30(1H, overlap, H-5), 3.25(1H, overlap, H-4), 3.21(1H, Overlap, H-3), 3.13(1H, dd,J =9.0,7.8 Hz, H-2), 2.71(2H, m, H2- 7 ')；13C-NMR(100 MHz, CD3OD)δ: 104.3(d, C-1), 75.0(d, C-2), 77.8(d, C-3) and, 71.5(d, C-4), 78.0(d, C-5), 62.6(d, C-6), 131.4(s, C-1 '), 116.3(d, C-2 '), 146.0(s, C-3 '), 144.6(s, C-4 '), 117.1(d, C-5 '), 121.2(d, C-6 '), 36.6(t, C-7 '), 72.1(t, C-8 ').
Compound 2: brown solid.UV(MeOH)λ max(logε): 223(4.11), 290(3.55) nm；HR-ESI-MSm/z: 329.3205 [M-H]-(calcd for C14H17O9, 329.3202)；1H-NMR(400 MHz, CD3OD)δ: 7.08(2H, D,J =10.2 Hz, H-2 ', 6 '), 6.12(2H, d,J =10.2 Hz, H-3 ', 5 '), 4.43(1H, dd,J =11.9,2.1 Hz, H-6a), 4.15(1H, d,J =7.8 Hz, H-1), 4.21(1H, overlap, H-6b), 3.30(1H, overlap, H- 5), 3.25(1H, overlap, H-4), 3.21(1H, overlap, H-3), 3.13(1H, dd,J =9.0,7.8 Hz, H-2), 2.75(2H s, H2- 7 ')；13C-NMR(100 MHz, CD3OD)δ: 102.3(d, C-1), 75.1(d, C-2), 77.9(d, C-3), 71.4(d, C-4), 78.2(d, C-5), 64.6(d, C-6) and, 68.1(s, C-1 '), 152.3(d, C-2 ', 6 '), 128.0(d, C- 3 ', 5 '), 187.6(s, C-4 '), 45.5(t, C-7 '), 170.9(s, C-8 ').
Compound 3: brown solid.UV(MeOH)λ max(logε): 222(4.03), 290(3.48) nm；HR-ESI-MSm/z: 343.3505 [M-H]-(calcd for C15H19O9, 343.3512)；1H-NMR(400 MHz, CD3OD)δ: 6.74(1H, D,J =2.1 Hz, H-2 '), 6.69(1H, d,J =8.1 Hz, H-5 '), 6.59(1H, d,J =8.1,2.1 Hz, H-6 '), 4.45(1H, dd,J =11.9,2.1 Hz, H-6a), 4.22(1H, overlap, H-6b), 4.18(1H, d,J =7.8 Hz, H-1), 3.85(3H, s ,-OCH3), 3.49(2H, s, H2- 7 '), 3.44(1H, m, H-5), 3.38(1H, overlap, H-3), 3.35(1H, overlap, H-4), 3.17(1H, dd,J =9.1,7.8 Hz, H-2)；13C-NMR(100 MHz, CD3OD)δ: 102.3(d, C-1), 74.7(d, C-2), 77.9(d, C-3) and, 71.5(d, C-4), 75.3(d, C-5) and, 64.2(t, C-6), 126.9(s, C-1 '), 117.5(d, C-2 '), 148.2(s, C-3 '), 146.5(s, C-4 '), 116.5(d, C-5 '), 121.6 (d, C-6 '), 41.1(t, C-7 '), 173.9(s, C-8 '), 56.1(q ,-OCH3).
Compound 4: brown solid.UV(MeOH)λ max(logε): 224(4.07), 291(3.57) nm；HR-ESI-MSm/z: 315.1514 [M-H]-(calcd for C14H19O8, 315.1513)；1H-NMR(400 MHz, CD3OD)δ: 6.64(1H, D,J =2.1 Hz, H-2 '), 6.58(1H, d,J =8.1 Hz, H-5 '), 6.48(1H, dd,J =8.0,2.1 Hz, H- 6 '), 4.47(1H, dd,J =11.9,2.1 Hz, H-6a), 4.24(1H, overlap, H-6b), 4.16(1H, d,J = 7.8 Hz, H-1), 3.48(2H, overlap, H2- 7 ' '), 3.46(1H, m, H-5), 3.39(1H, overlap, H-3), 3.34(1H, Overlap, H-4), 3.22(1H, dd,J =9.1,7.8 Hz, H-2)；13C-NMR(100 MHz, CD3OD)δ: 102.0(d, C- 1), 75.0(d, C-2), 78.0(d, C-3), 71.5(d, C-4) and, 75.4(d, C-5), 64.3(t, C-6) and, 131.2(s, C-1 '), 116.2(d, C-2 '), 146.1(s, C-3 '), 144.3(s, C-4 '), 117.2(d, C-5 '), 121.4(d, C-6 '), 36.7(t, C-7 '), 72.1(t, C-8 ').
Compound 5: brown solid.UV(MeOH)λ max(logε): 224(4.12), 291(3.67) nm；HR-ESI-MSm/z: 465.1517 [M-H]-(calcd for C22H25O11, 465.1516)；1H-NMR(400 MHz, CD3OD)δ: 6.72 (1H, d,J =2.1 Hz, H-2 ' '), 6.69(2H, overlap, H-5 ', 5 ' ') and, 6.67(1H, overlap, H-2 '), 6.57 (1H, overlap, H-6 ' '), 6.55(1H, overlap, H-6 '), 4.42(1H, dd,J =11.9,2.1 Hz, H-6a), 4.25(1H, d,J =7.8 Hz, H-1), 4.21(1H, overlap, H-6b), 3.87(1H, m, H-8 ' a), 3.63(1H, m, H- 8 ' b), 3.49(2H, s, H2- 7 ' '), 3.44(1H, m, H-5), 3.35(1H, overlap, H-3), 3.33(1H, overlap, H- 4), 3.18(1H, dd,J =9.1,7.8 Hz, H-2), 2.76(2H, t,J =7.3 Hz, H2- 7 ')；13C-NMR(100 MHz, CD3OD)δ: 104.3(d, C-1), 74.9(d, C-2), 77.8(d, C-3) and, 71.6(d, C-4), 75.2(d, C-5), 64.2(t, C-6), 131.5(s, C-1 '), 116.3(d, C-2 '), 145.9(s C-3 '), 144.5(s, C-4 '), 117.1(d, C-5 '), 121.3(d, C-6 '), 36.5(t, C-7 '), 72.1(t, C-8 '), 126.8(s, C-1 ' '), 117.4(d, C-2 ' '), 145.3 (s, C-3 ' '), 146.2(s, C-4 ' '), 116.3(d, C-5 ' '), 121.7(d, C-6 ' '), 41.3(t, C-7 ' '), 173.9(s, C-8 ' ').
Compound 6: brown solid.UV(MeOH)λ max(logε): 223(4.22), 291(3.84) nm；HR-ESI-MSm/z: 465.1405 [M-H]-(calcd for C22H25O11, 465.1402)；1H-NMR(400 MHz, CD3OD)δ: 7.07 (2H, d,J =10.1 Hz, H-2 ' ', 6 ' '), 6.11(2H, d,J =10.1 Hz, H-3 ' ', 5 ' '), 6.69(1H, d,J = 8.0 Hz, H-5 '), 6.66(1H, d,J =2.1 Hz, H-2 '), 6.56(1H, dd,J =8.0,2.1 Hz, H-6 '), 4.44 (1H, dd,J =11.9,2.1 Hz, H-6a), 4.30(1H, d,J =8.0 Hz, H-1), 4.19(1H, dd,J =11.9, 5.8 Hz, H-6b), 3.95(1H, overlap, H-8 ' a), 3.68(1H, overlap, H-8 ' b), 3.45(1H, overlap, H- 5), 3.37(1H, overlap, H-4), 3.34(1H, overlap, H-3), 3.19(1H, t,J =8.4 Hz, H-2), 2.79 (2H, overlap, H2- 7 '), 2.77(2H, s, H2- 7 ' ')；13C-NMR(100 MHz, CD3OD)δ: 104.4(d, C-1), 75.0 (d, C-2), 77.8(d, C-3), 71.5(d, C-4), 75.1(d, C-5) and, 65.0(t, C-6), 131.4(s, C-1 '), 117.1 (d, C-2 '), 146.1(s C-3 '), 144.6(s, C-4 '), 116.3(d, C-5 '), 121.2(d, C-6 '), 36.6(t, C- 7 '), 72.3(t, C-8 '), 68.0(s, C-1 ' '), 152.7(d, C-2 ' ', 6 ' '), 128.3(d, C-3 ' ', 5 ' '), 187.4(s, C-4 ' '), 45.8(t, C-7 ' '), 170.3(s, C-8 ' ').
Compound 7: brown solid.UV(MeOH)λ max(logε): 223(4.32), 291(3.85) nm；HR-ESI-MSm/z: 465.1410 [M-H]-(calcd for C23H29O10, 465.1405)；1H-NMR(400 MHz, CD3OD)δ: 6.68 (1H, overlap, H-5 ', 5 ' '), 6.66(1H, overlap, H-2 ' and, 2 ' '), 6.57(1H, dd,J =7.9,2.1 Hz, H- 6 ', 6 ' '), 4.43(1H, dd,J =11.9,2.1 Hz, H-6a), 4.25(1H, d,J =7.8 Hz, H-1), 4.21(1H, Overlap, H-6b), 3.87(2H, overlap, H-8 ' a, 8 ' ' a), 3.85(3H, s ,-OCH3), 3.63(2H, overlap, H- 8 ' b, 8 ' ' b), 3.44(1H, m, H-5), 3.35(1H, overlap, H-3), 3.33(1H, overlap, H-4), 3.18(1H, Dd,J =9.1,7.8 Hz, H-2), 2.76(4H, overlap, H2- 7 ', 7 ' ')；13C-NMR(100 MHz, CD3OD)δ: 104.5(d, C-1), 74.8(d, C-2), 77.8(d, C-3) and, 71.3(d, C-4), 75.0(d, C-5) and, 64.5(t, C-6), 131.6(s, C-1 '), 116.2(d, C-2 '), 145.8(s C-3 '), 144.5(s, C-4 '), 117.3(d, C-5 '), 121.2 (d, C-6 '), 36.6(t, C-7 '), 72.1(t, C-8 '), 130.8(s, C-1 ' '), 117.6(d, C-2 ' '), 146.5(s, C- 3 ' '), 145.1(s, C-4 ' '), 116.0(d, C-5 ' '), 121.8(d, C-6 ' '), 36.4(t, C-7 ' '), 72.3(t, C- 8 ' '), 56.2(q ,-OCH3).
Compound 8: brown solid.UV(MeOH)λ max(logε): 223(4.25), 291(3.79) nm；HR-ESI-MSm/z: 451.1763 [M-H]-(calcd for C22H27O10, 451.1761)；1H-NMR(400 MHz, CD3OD)δ: 7.08 (2H, d,J =10.3 Hz, H-2 ' ', 6 ' '), 6.13(2H, d,J =10.3 Hz, H-3 ' ', 5 ' '), 6.68(1H, d,J = 8.0 Hz, H-5 '), 6.65(1H, d,J =2.1 Hz, H-2 '), 6.55(1H, dd,J =8.0,2.1 Hz, H-6 '), 4.45 (1H, dd,J =11.9,2.1 Hz, H-6a), 4.29(1H, d,J =8.0 Hz, H-1), 4.20(1H, dd,J =11.9, 5.8 Hz, H-6b), 3.95(2H, overlap, H-8 ' a, 8 ' ' a), 3.65(2H, overlap, H-8 ' b, 8 ' ' b), 3.45(1H, Overlap, H-5), 3.37(1H, overlap, H-4), 3.34(1H, overlap, H-3), 3.19(1H, t,J =8.4 Hz, H-2), 2.79(2H, overlap, H2- 7 '), 1.75(2H, m, H2- 7 ' ')；13C-NMR(100 MHz, CD3OD)δ: 104.4(d, C-1), 75.0(d, C-2), 77.8(d, C-3), 71.5(d, C-4) and, 75.1(d, C-5), 65.0(t, C-6) and, 131.4(s, C- 1 '), 117.1(d, C-2 '), 146.1(s C-3 '), 144.6(s, C-4 '), 116.3(d, C-5 '), 121.2(d, C-6 '), 36.6(t, C-7 '), 72.3(t, C-8 '), 68.0(s, C-1 ' '), 152.7(d, C-2 ' ', 6 ' '), 128.3(d, C-3 ' ', 5 ' '), 187.4(s, C-4 ' '), 36.8(t, C-7 ' '), 68.3(s, C-8 ' ').
Compound 9: brown solid.UV(MeOH)λ max(logε): 224(4.28), 291(3.81) nm；HR-ESI-MSm/z: 465.2363 [M-H]-(calcd for C22H25O11, 465.2361)；1H-NMR(400 MHz, CD3OD)δ: 6.68 (1H, overlap, H-5 ', 5 ' '), 6.66(1H, overlap, H-2 ' and, 2 ' '), 6.57(1H, dd,J =7.9,2.1 Hz, H- 6 ', 6 ' '), 4.43(1H, dd,J =11.9,2.1 Hz, H-6a), 4.25(1H, d,J =7.8 Hz, H-1), 4.21(1H, Overlap, H-6b), 3.87(1H, overlap, H-8 ' a), 3.87(3H, s ,-OCH3), 3.63(1H, overlap, H-8 ' b), 3.44(1H, m, H-5), 3.35(1H, overlap, H-3), 3.33(1H, overlap, H-4), 3.18(1H, dd,J =9.1, 7.8 Hz, H-2), 2.76(2H, overlap, H2- 7 ')；13C-NMR(100 MHz, CD3OD)δ: 104.8(d, C-1), 75.1 (d, C-2), 77.8(d, C-3), 71.5(d, C-4), 75.3(d, C-5) and, 64.9(t, C-6), 131.6(s, C-1 '), 116.2 (d, C-2 '), 145.8(s C-3 '), 144.6(s, C-4 '), 117.2(d, C-5 '), 121.2(d, C-6 '), 36.4(t, C- 7 '), 72.2(t, C-8 '), 130.8(s, C-1 ' '), 117.3(d, C-2 ' '), 146.5(s, C-3 ' '), 145.1(s, C-4 ' '), 116.1(d, C-5 ' '), 121.9(d, C-6 ' '), 170.4(s, C-7 ' '), 56.2(q ,-OCH3).
Compound 10: brown solid.UV(MeOH)λ max(logε): 221(4.35), 291(3.88) nm；HR-ESI-MSm/z: 465.2531 [M-H]-(calcd for C22H25O11, 465.2538)；1H-NMR(400 MHz, CD3OD)δ: 6.75 (1H, d,J =2.0 Hz, H-2 ' '), 6.70(1H, d,J =8.0, Hz, H-5 ' '), 6.66(1H, d,J =7.9 Hz, H- 5 '), 6.62(1H, d,J =2.0 Hz, H-2 '), 6.59(1H, dd,J =8.0,2.0 Hz, H-6 ' '), 6.49(1H, dd,J =7.9,2.0 Hz, H-6 '), 4.69(1H, d,J =9.6,8.1Hz, H-2), 4.39(1H, d,J =8.1 Hz, H-1), 3.88(2H, m, H-8 ', 6a), 3.68(2H, dd,J =12.1,2.1Hz, H-6b), 3.53(1H, m, H-3), 3.45(2H, s, H2- 7 ' '), 3.40(1H, overlap, H-4), 3.36(1H, overlap, H-5), 2.53(2H, t,J =7.2 Hz, H2- 7 ') ；13C-NMR(100 MHz, CD3OD)δ: 102.1(d, C-1), 75.3(d, C-2), 76.0(d, C-3) and, 71.6(d, C-4), 77.9 (d, C-5), 62.5(t, C-6), 131.5(s, C-1 '), 116.2(d, C-2 '), 145.9(s C-3 '), 144.5(s, C-4 '), 117.1(d, C-5 '), 121.3(d, C-6 '), 36.2(t, C-7 '), 71.8(t, C-8 '), 126.9(s C-1 ' '), 117.6(d C-2 ' '), 145.3(s C-3 ' '), 146.1(s C-4 ' ') and, 116.2(d C-5 ' '), 121.8(d C-6 ' ') and, 41.5(t C- 7 ' '), 173.0(s C-8 ' ').
Compound 11: brown solid.UV(MeOH)λ max(logε): 222(4.36), 291(3.80) nm；HR-EI-MSm/z: 461.1463 [M-H]-(calcd for C23H26O10, 461.1453)；1H-NMR(400 MHz, CD3COCD3)δ: 7.61 (1H, d,J =15.9 Hz H-7 ' '), 7.49(2H, d,J =8.5 Hz, H-2 ' ', 6 ' '), 6.88(2H, d,J = 8.5 Hz, H-3 ' ', 5 ' '), 6.76(1H, d,J =2.0 Hz, H-5 '), 6.70(1H, d,J =8.0 Hz, H-2 '), 6.56(1H, Dd,J =8.0,2.0 Hz, H-6 '), 6.37(1H, d,J =15.9 Hz, H-8 ' '), 4.52 (1H, dd,J =11.8,2.1 Hz, H-6a), 4.39(1H, d,J =7.7 Hz, H-1), 4.33(1H, m, H-6b), 3.94(1H, m, H-8 ' a), 3.67(1H, M, H-8 ' b), 3.58(1H, m, H-5), 3.50(1H, overlap, H-3), 3.44(1H, overlap, H-4), 3.28(1H, Overlap, H-2), 2.76(2H, t,J =7.6 Hz, H2- 7 ')；13C-NMR(100 MHz, CD3COCD3)δ: 104.1(d, C- 1), 74.7(d, C-2), 77.7(d, C-3), 71.3(d, C-4) and, 74.9(d, C-5), 64.3(t, C-6) and, 131.1(s, C-1 '), 116.0(d, C-2 '), 145.6(s, C-3 '), 144.2(s, C-4 '), 116.8(d, C-5 '), 121.0(d, C-6 '), 36.3(t, C-7 '), 71.6(t, C-8 '), 126.8(s, C-1 ' '), 131.0(d, C-2 ' ', 6 ' '), 116.7(d, C-3 ' ', 5 ' '), 160.5 (s, C-4 ' '), 145.7(d, C-7 ' '), 115.2(d, C-8 ' '), 167.6(s, C-9 ' ').
Compound 12: brown solid.UV(MeOH)λ max(logε): 223(4.25), 291(3.70) nm；HR-ESI-MSm/z: 479.3677 [M-H]-(calcd for C22H23O12, 479.3678)；1H-NMR(400 MHz, CD3OD)δ: 7.07 (2H, d,J =10.4 Hz, H-2 ' ', 6 ' '), 6.10(2H, d,J =10.4 Hz, H-3 ' ', 5 ' '), 6.70(1H, d,J = 8.0 Hz, H-5 '), 6.68(1H, d,J =2.1 Hz, H-2 '), 6.57(1H, dd,J =8.0,2.1 Hz, H-6 '), 4.45 (1H, dd,J =11.8,2.2 Hz, H-6a), 4.19(1H, dd,J =11.8,5.8 Hz, H-6b), 4.16(1H, d,J = 8.0 Hz, H-1), 3.93(1H, overlap, H-8 ' a), 3.86(3H, s ,-OCH3), 3.63(1H, overlap, H-8 ' b), 3.51(1H, overlap, H-5), 3.39(1H, overlap, H-4), 3.36(1H, overlap, H-3), 3.19(1H, t,J = 8.4 Hz, H-2), 2.79(2H, s, H2- 7 ' ')；13C-NMR(100 MHz, CD3OD)δ: 101.9(d, C-1), 75.2(d, C- 2), 79.8(d, C-3), 71.2(d, C-4), 75.0(d, C-5) and, 65.2(t, C-6), 131.2(s, C-1 '), 117.0(d, C- 2 '), 147.1(s C-3 '), 145.6(s, C-4 '), 116.3(d, C-5 '), 122.2(d, C-6 '), 171.6(s, C-7 '), 68.1(s, C-1 ' '), 152.8(d, C-2 ' ', 6 ' '), 128.3(d, C-3 ' ', 5 ' '), 187.5(s, C-4 ' '), 45.7(t, C- 7 ' '), 170.5(s, C-8 ' '), 56.2(q ,-OCH3).
Compound 13: brown solid.UV(MeOH)λ max(logε): 220(4.38), 292(3.99) nm；HR-ESI-MSm/z: 615.1702 [M-H]-(calcd for C30H31O14, 615.1719)；1H-NMR(400 MHz, CD3OD)δ: 6.76 (1H, d,J =2.1 Hz, H-2 ' '), 6.74(1H, d,J =2.1 Hz, H-2 ' ' '), 6.72(1H, d,J =8.5 Hz, H- 5 ' '), 6.70(2H, d,J =8.6 Hz, H-5 ', 5 ' ' '), 6.65(1H, d,J =2.1 Hz, H-2 '), 6.58(1H, Overlap, H-6 ' '), 6.57(1H, overlap, H-6 ' ' '), 6.51(1H, d,J =8.1,2.1 Hz, H-6 '), 4.71 (1H, dd,J =9.2,8.0 Hz, H-2), 4.42(1H, dd,J =11.9,2.0 Hz, H-6a), 4.34(1H, d,J = 8.0 Hz, H-1), 4.23(1H, dd,J =11.9,5.9 Hz, H-6b), 3.78(1H, dd,J =9.4,6.9 Hz, H-8 ' a), 3.48(2H s, H2- 7 ' ' '), 3.54(1H, t,J =9.2 Hz, H-3), 3.45(2H, overlap, H-5,8 ' b), and 3.43 (2H, s, H2- 7 ' '), 3.39(1H, t,J =9.2 Hz, H-4), 2.54(2H, m, H2- 7 ')；13C-NMR(100 MHz, CD3OD)δ: 101.9(d, C-1), 75.0(d, C-2), 75.6(d, C-3) and, 71.5(d, C-4), 75.0(d, C-5) and, 64.6(t, C-6), 131.6(s, C-1 '), 117.1(d, C-2 '), 145.6(s C-3 '), 144.2(s, C-4 '), 116.3(d, C-5 '), 121.4 (d, C-6 '), 36.0(t, C-7 '), 71.7(t, C-8 '), 126.8(s, C-1 ' '), 117.5(d, C-2 ' '), 145.9(s, C- 3 ' '), 145.1(s, C-4 ' '), 116.2(d, C-5 ' '), 121.8(d, C-6 ' '), 41.2(t, C-7 ' '), 173.1(s, C- 8 ' '), 126.7(s, C-1 ' ' '), 117.3(d, C-2 ' ' '), 145.9(s, C-3 ' ' '), 145.1(s, C-4 ' ' '), 116.1(d, C-5 ' ' '), 121.7(d, C-6 ' ' '), 41.1(t, C-7 ' ' '), 173.9(s, C-8 ' ' ').
Compound 14: brown solid.UV(MeOH)λ max(logε): 222(4.58), 291(3.99) nm；HR-ESI-MSm/z: 599.1832 [M-H]-(calcd for C31H35O12, 599.1832)；1H-NMR(400 MHz, CD3OD)δ: 7.08 (2H, d,J =8.1 Hz, H-2 ' ', 6 ' '), 6.74(2H, d,J =8.1 Hz, H-3 ' ', 5 ' '), 6.72(1H, d,J = 2.1 Hz, H-2 ' ' '), 6.70(1H, d,J =8.3 Hz, H-5 ' ' '), 6.68(1H, d,J =8.1 Hz, H-5 '), 6.65(1H, d,J =2.1 Hz, H-2 '), 6.57(1H, overlap, H-6 ' ' '), 6.52(1H, d,J =8.1,2.1 Hz, H-6 '), 4.72 (1H, dd,J =9.1,8.0 Hz, H-2), 4.41(1H, dd,J =11.8,2.0 Hz, H-6a), 4.35(1H, d,J = 8.0 Hz, H-1), 4.22(1H, dd,J =11.8,5.9 Hz, H-6b), 3.87(3H, s ,-OCH3), 3.78(2H, overlap, H- 8 ' a, 8 ' ' ' a), 3.54(1H, t,J =9.2 Hz, H-3), 3.45(3H, overlap, H-5,8 ' b, 8 ' ' ' b), 3.47(2H, S, H2- 7 ' '), 3.38(1H, t,J =9.2 Hz, H-4), 2.55(4H, overlap, H2- 7 ', 7 ' ' ')；13C-NMR(100 MHz, CD3OD)δ: 102.2(d, C-1), 75.1(d, C-2), 75.7(d, C-3) and, 71.5(d, C-4), 74.9(d, C-5) and, 64.8 (t, C-6), 131.8(s, C-1 '), 117.2(d, C-2 '), 145.3(s C-3 '), 144.4(s, C-4 '), 116.2(d, C- 5 '), 121.4(d, C-6 '), 36.1(t, C-7 '), 71.7(t, C-8 '), 126.9(s, C-1 ' '), 117.5(d, C-2 ' '), 145.9(s, C-3 ' '), 145.1(s, C-4 ' '), 116.3(d, C-5 ' '), 121.5(d, C-6 ' '), 41.2(t, C-7 ' '), 173.0(s, C-8 ' '), 131.7(s, C-1 ' ' '), 117.3(d, C-2 ' ' '), 147.9(s, C-3 ' ' '), 145.2(s, C- 4 ' ' '), 116.1(d, C-5 ' ' '), 121.7(d, C-6 ' ' '), 36.4(t, C-7 ' ' '), 72.0(t, C-8 ' ' '), 56.7(q ,- OCH3).
Compound 15: brown solid.UV(MeOH)λ max(logε): 223(4.27), 291(3.82) nm；HR-ESI-MSm/z: 615.1714 [M-H]-(calcd for C30H31O14, 615.1719)；1H-NMR(400 MHz, CD3OD)δ: 7.06 (2H, d,J =10.1 Hz, H-2 ' ' ', 6 ' ' '), 6.72(1H, d,J =8.1 Hz, H-5 '), 6.77(1H, d,J = 2.0 Hz, H-2 ' '), 6.69(1H, d,J =8.0 Hz, H-5 ' '), 6.64(1H, d,J =2.0 Hz, H-2 '), 6.60(1H, dd,J =8.0,2.0 Hz, H-6 ' '), 6.51(1H, d,J =8.0,2.0 Hz, H-6 '), 6.12(2H, d,J =10.1 Hz, H- 3 ' ' ', 5 ' ' '), 4.71(1H, dd,J =9.6,8.0 Hz, H-2), 4.44(1H, m, H-6a), 4.40(1H, d,J = 8.0 Hz, H-1), 4.21(1H, dd,J =11.9,5.3 Hz, H-6b), 3.85(1H, m, H-8 ' a), 3.56(1H, t,J = 9.2 Hz, H-3), 3.46(2H, s, H2- 7 ' '), 3.45(2H, overlap, H-5,8 ' b), 3.37(1H, overlap, H-4), 2.75 (2H, s, H2- 7 ' ' '), 2.54(2H, t,J=7.3 Hz, H2- 7 ')；13C-NMR(100 MHz, CD3OD)δ: 101.9(d, C- 1), 75.0(d, C-2), 75.5(d, C-3), 71.4(d, C-4) and, 74.8(d, C-5), 64.6(t, C-6) and, 131.3(s, C-1 '), 117.0(d, C-2 '), 145.6(s C-3 '), 144.2(s, C-4 '), 116.1(d, C-5 '), 121.8(d, C-6 '), 36.1(t, C-7 '), 71.8(t, C-8 '), 126.8(s, C-1 ' '), 117.5(d, C-2 ' '), 145.9(s, C-3 ' '), 145.1(s, C- 4 ' '), 116.2(d, C-5 ' '), 121.3(d, C-6 ' '), 41.3(t, C-7 ' '), 173.0(s, C-8 ' '), 67.9(s, C- 1 ' ' '), 152.6(d, C-2 ' ' ', 6 ' ' '), 128.1(d, C-3 ' ' ', 5 ' ' '), 187.4(s, C-4 ' ' '), 45.5(t, C- 7 ' ' '), 170.2(s, C-8 ' ' ').
Compound 16: brown solid.UV(MeOH)λ max(logε): 224(4.33), 285(3.75) nm；HR-ESI-MSm/z: 599.1766 [M-H]-(calcd for C30H31O13, 599.1770)；1H-NMR(400 MHz, CD3OD)δ: 7.08 (2H, overlap, H-2 ' ', 6 ' '), 7.07(2H, overlap, H-2 ' ' ', 6 ' ' '), 6.68(1H, overlap, H-5 '), 6.74(1H, d,J =8.2 Hz, H-3 ' ', 5 ' '), 6.64(1H, overlap, H-2 '), 6.50(1H, d,J =8.2,2.4 Hz, H-6 '), 6.13(2H, d,J =10.1 Hz, H-3 ' ' ', 5 ' ' '), 4.71(1H, overlap, H-2), 4.44(1H, Overlap, H-6a), 4.40(1H, d,J =8.2 Hz, H-1), 4.21(1H, dd,J =12.1,5.5 Hz, H-6b), 3.85 (1H, overlap, H-8 ' a), 3.54(1H, overlap, H-3), 3.51(2H, s, H2- 7 ' '), 3.47(2H, overlap, H- 5,8 ' b), 3.40(1H, overlap, H-4), 2.76(2H, s, H2- 7 ' ' '), 2.56(2H, t,J=7.3 Hz, H2- 7 ')；13C-NMR(100 MHz, CD3OD)δ: 101.9(d, C-1), 75.1(d, C-2), 75.6(d, C-3) and, 71.5(d, C-4), 75.0 (d, C-5), 64.7(t, C-6), 131.4(s, C-1 '), 117.1(d, C-2 '), 145.9(s C-3 '), 144.5(s, C-4 '), 116.1(d, C-5 '), 121.3(d, C-6 '), 36.2(t, C-7 '), 71.8(t, C-8 '), 126.3(s, C-1 ' '), 131.4(d, C-2 ' ', 6 ' '), 116.1(d, C-3 ' ', C-5 ' '), 157.2(s, C-4 ' '), 41.1(t, C-7 ' '), 173.1(s, C-8 ' '), 68.0(s, C-1 ' ' '), 152.7(d, C-2 ' ' ', 6 ' ' '), 128.2(d, C-3 ' ' ', 5 ' ' '), 187.5(s, C-4 ' ' '), 45.6 (t, C-7 ' ' '), 170.2(s, C-8 ' ' ').
Compound 17: brown solid.UV(MeOH)λ max(logε): 222(4.68), 291(3.89) nm；HR-ESI-MSm/z: 611.1122 [M-H]-(calcd for C31H31O13, 611.1123)；1H-NMR(400 MHz, CD3OD)δ: 7.61 (1H, d,J =15.7 Hz H-7 ' '), 7.48(2H, d,J =8.3 Hz, H-2 ' ', 6 ' '), 7.08(2H, d,J = 10.1 Hz, H-2 ' ' ', 6 ' ' '), 6.87(2H, d,J =8.3 Hz, H-3 ' ', 5 ' '), 6.68(1H, overlap, H-5 '), 6.64 (1H, overlap, H-2 '), 6.50(1H, d,J =8.2,2.4 Hz, H-6 '), 6.37(1H, d,J =15.7 Hz, H- 8 ' '), 6.12(2H, d,J =10.1 Hz, H-3 ' ' ', 5 ' ' '), 4.72(1H, overlap, H-2), 4.41(1H, overlap, H-6a), 4.40(1H, d,J =8.2 Hz, H-1), 4.23(1H, dd,J =12.1,5.5 Hz, H-6b), 3.85(1H, Overlap, H-8 ' a), 3.53(1H, overlap, H-3), 3.49(2H, overlap, H-5,8 ' b), 3.42(1H, overlap, H-4), 2.76(2H, s, H2- 7 ' ' '), 2.56(2H, t,J=7.3 Hz, H2- 7 ')；13C-NMR(100 MHz, CD3OD)δ: 101.9(d, C-1), 75.1(d, C-2), 75.5(d, C-3) and, 71.3(d, C-4), 75.1(d, C-5) and, 64.9(t, C-6), 131.2(s, C-1 '), 117.2(d, C-2 '), 145.9(s C-3 '), 144.5(s, C-4 '), 116.2(d, C-5 '), 121.4 (d, C-6 '), 36.1(t, C-7 '), 71.9(t, C-8 '), 126.7(s, C-1 ' '), 131.0(d, C-2 ' ', 6 ' '), 116.6(d, C-3 ' ', 5 ' '), 160.5(s, C-4 ' '), 145.8(d, C-7 ' '), 115.2(d, C-8 ' '), 168.6(s, C-9 ' '), 68.0 (s, C-1 ' ' '), 152.7(d, C-2 ' ' ', 6 ' ' '), 128.1(d, C-3 ' ' ', 5 ' ' '), 187.6(s, C-4 ' ' '), 45.6(t, C-7 ' ' '), 170.1(s, C-8 ' ' ').
Compound 18: brown solid.UV(MeOH)λ max(logε): 223(4.78), 290(3.89) nm；HR-ESI-MSm/z: 601.1482 [M-H]-(calcd for C31H37O12, 601.1487)；1H-NMR(400 MHz, CD3OD)δ: 7.07 (2H, d,J =10.1 Hz, H-2 ' ' ', 6 ' ' '), 6.76(1H, d,J =8.1 Hz, H-5 '), 6.73(1H, d,J = 2.0 Hz, H-2 ' '), 6.69(1H, d,J =8.0 Hz, H-5 ' '), 6.65(1H, d,J =2.0 Hz, H-2 '), 6.61(1H, dd,J =8.0,2.0 Hz, H-6 ' '), 6.50(1H, d,J =8.0,2.0 Hz, H-6 '), 6.12(2H, d,J =10.1 Hz, H- 3 ' ' ', 5 ' ' '), 4.70(1H, dd,J =9.6,8.0 Hz, H-2), 4.43(1H, m, H-6a), 4.40(1H, d,J = 8.0 Hz, H-1), 4.23(1H, dd,J =11.9,5.3 Hz, H-6b), 3.87(3H, s ,-OCH3), 3.85(3H, overlap, H- 8 ' a, 8 ' ' a, 8 ' ' ' a), 3.56(1H, t,J =9.2 Hz, H-3), 3.43(4H, overlap, H-5,8 ' b, 8 ' ' b, 8 ' ' ' B), 3.38(1H, overlap, H-4), 2.56(2H, s, H2- 7 ' '), 2.54(2H, t,J=7.3 Hz, H2- 7 '), 1.75(2H, M, H2- 7 ' ' ')；13C-NMR(100 MHz, CD3OD)δ: 101.9(d, C-1), 75.2(d, C-2), 75.4(d, C-3) and, 71.4 (d, C-4), 74.8(d, C-5), 64.8(t, C-6), 131.3(s, C-1 '), 117.1(d, C-2 '), 145.6(s C-3 '), 144.3(s, C-4 '), 116.1(d, C-5 '), 121.7(d, C-6 '), 36.1(t, C-7 '), 71.8(t, C-8 '), 130.8(s, C-1 ' '), 117.5(d, C-2 ' '), 145.9(s, C-3 ' '), 145.1(s, C-4 ' '), 116.2(d, C-5 ' '), 121.3(d, C- 6 ' '), 36.3(t, C-7 ' '), 72.0(t, C-8 ' '), 67.8(s, C-1 ' ' '), 152.5(d, C-2 ' ' ', 6 ' ' '), 128.3(d, C-3 ' ' ', 5 ' ' '), 187.4(s, C-4 ' ' '), 36.5(t, C-7 ' ' '), 70.9(t, C-8 ' ' '), 56.5(q ,-OCH3).
Compound 19: brown solid.UV(MeOH)λ max(logε): 221(4.85), 291(3.77) nm；HR-ESI-MSm/z: 615.1657 [M-H]-(calcd for C31H35O13, 615.1653)；1H-NMR(400 MHz, CD3OD)δ: 7.08 (2H, d,J =10.2 Hz, H-2 ' ' ', 6 ' ' '), 6.77(1H, d,J =8.1 Hz, H-5 '), 6.75(1H, d,J = 2.0 Hz, H-2 ' '), 6.68(1H, d,J =8.0 Hz, H-5 ' '), 6.66(1H, d,J =2.0 Hz, H-2 '), 6.62(1H, dd,J =8.0,2.0 Hz, H-6 ' '), 6.51(1H, d,J =8.0,2.0 Hz, H-6 '), 6.13(2H, d,J =10.2 Hz, H- 3 ' ' ', 5 ' ' '), 4.73(1H, dd,J =9.6,8.0 Hz, H-2), 4.42(1H, m, H-6a), 4.40(1H, d,J = 8.0 Hz, H-1), 4.21(1H, dd,J =11.9,5.3 Hz, H-6b), 3.87(3H, s ,-OCH3), 3.85(2H, overlap, H- 8 ' a, 8 ' ' ' a), 3.55(1H, t,J =9.2 Hz, H-3), 3.43(3H, overlap, H-5,8 ' b, 8 ' ' ' b), 3.38(1H, Overlap, H-4), 2.54(2H, t,J=7.3 Hz, H2- 7 '), 1.74(2H, m, H2- 7 ' ' ')；13C-NMR(100 MHz, CD3OD)δ: 101.9(d, C-1), 75.1(d, C-2), 75.4(d, C-3) and, 71.5(d, C-4), 74.8(d, C-5), 64.5(t, C-6), 131.3(s, C-1 '), 117.1(d, C-2 '), 145.6(s C-3 '), 144.8(s, C-4 '), 116.2(d, C-5 '), 121.7(d, C-6 '), 36.1(t, C-7 '), 71.8(t, C-8 '), 131.1(s, C-1 ' '), 117.5(d, C-2 ' '), 145.9 (s, C-3 ' '), 145.1(s, C-4 ' '), 116.2(d, C-5 ' '), 121.3(d, C-6 ' '), 169.8(s, C-7 ' '), 68.1(s, C-1 ' ' '), 152.4(d, C-2 ' ' ', 6 ' ' '), 128.1(d, C-3 ' ' ', 5 ' ' '), 187.4(s, C-4 ' ' '), 36.5(t, C- 7 ' ' '), 70.9(t, C-8 ' ' '), 56.6(q ,-OCH3).
Embodiment 3:
The analgesic activities of the compounds of this invention detect:
Using the analgesic activities of acetic acid twisting measuring extract of the present invention.Kunming mouse half male and half female, weight 18~22 G tests preceding fasting in 12 hours, can't help water, is randomly divided into control group, sample sets, positive drug group, and every group 6.With 200 mg/kg Dosage gastric infusion, negative control group gives same amount of normal saline, and positive drug group gives aspirin, after 40 min are administered, Every mouse peritoneal injects 0.6% glacial acetic acid solution, 0.2 mL/10g, observes and records 15 min after injecting 3~5 min of glacial acetic acid The writhing number of interior mouse, be calculated according to the following formula tested material to the inhibiting rate of mouse acetic acid twisting, evaluates tested material with this Analgesic activity.
Pain inhibiting rate (%)=(negative control group writhing number-administration group writhing number)/negative control group writhing number × 100%
Activity data is shown in Table 1.
1 compound 1-19 of table analgesic activities data (n=6)
Embodiment 4:
Tablet: any 10 mg of compound, 180 mg of lactose, 55 mg of starch, 5 mg of magnesium stearate obtained by Examples 1 and 2；
Preparation method: compound, newborn sugar and starch are mixed, uniformly moistened with propylene glycol, the mixture after wet is sieved simultaneously Dry, magnesium stearate is added in re-sieving, and then by mixture tabletting, every 250 mg of slice weight, compounds content is 10 mg.
Embodiment 5:
Ampulla: any 5 mg of compound obtained by Examples 1 and 2；
Preparation method: any compound obtained by Examples 1 and 2 is dissolved in 3 mL propylene glycol, acquired solution is filtered, sterile Under the conditions of be fitted into ampoule bottle.
Embodiment 6:
Capsule: any 10 mg of compound, 187 mg of lactose, 3 mg of magnesium stearate obtained by Examples 1 and 2；
Preparation method: compound is mixed with auxiliary agent, and sieving uniformly mixes, and obtained mixture is packed into hard gelatin capsule, often 200 mg in a capsule, active component content are 10 mg.

Claims (6)

  1. The following general formula 1. (I) compound,
    R in logical formula (I)1、R2、R3、R4And R5Representative group is selected from hydrogen (- H) or following structure fragment:
    ；
    X and Y is hydrogen (- H), hydroxyl (- OH) or methoxyl group (- OCH3).
  2. 2. the preparation method of formula (I) compound described in claim 1, take Theaceae Ternstroemia gymnanthera [Ternstroemia gymnanthera(Wight et Arn.) Bedd.] plant aerial part or complete stool, with organic solvent dichloromethane or chlorine Imitative or ethyl acetate or acetone or methanol or ethyl alcohol or the direct cold soaking of water or heat reflux or the auxiliary such as ultrasound or microwave mention Take, either first with above-mentioned organic solvent or water cooling soak or reflux or the assisted extractions such as ultrasound or microwave after use ethyl acetate again Total medicinal extract is obtained by extraction, total medicinal extract is chromatographed to obtain formula (I) compound repeatedly.
  3. 3. the preparation method of formula (I) compound as claimed in claim 2, it is characterised in that by Theaceae Ternstroemia gymnanthera [Ternstroemia gymnanthera(Wight et Arn.) Bedd.] plant aerial part or complete stool dry in the shade, crush It to 20-30 mesh, is extracted 2-5 times at room temperature with 95% ethyl alcohol, each 12-72 h, combined extract, extracting solution decompression is dense Contract to obtain medicinal extract, is suspended with suitable quantity of water, then for several times with ethyl acetate distribution, obtains acetic acid ethyl ester extract, the appropriate Lv Fang ∕ of extract 80-100 mesh silica gel mixed sample is used after acetone solution, is then carried out column chromatography with 200-300 mesh silica gel and is drawn section rough segmentation, with 1: 0-0: 1 Lv Fang ∕ acetone or 1: 0-0: 1 Lv Fang ∕ methanol carry out gradient elution, 7 major parts are obtained, by 9: 1 Lv ∕ first portions Point, 8: the 2 ∕ first parts Lv and 7: the 3 ∕ first parts Lv carry out silica gel column chromatography, with the progress of 100: 1-1: 1 Lv Fang ∕ acetone Gradient elution obtains 10 parts, then carry out repeatedly silica gel respectively, RP-18 and Sephadex LH-20 column chromatographs to obtain formula (I) chemical combination Object.
  4. 4. pharmaceutical composition, wherein any formula (I) compound described in the claim 1 containing therapeutically effective amount and can pharmaceutically connect The carrier received.
  5. 5. analgestic, wherein containing any formula (I) compound and conventional adjuvant described in claim 1.
  6. 6. any formula (I) compound described in claim 1 is preparing the application in analgesic.
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CN102304156A (en) * 2011-06-24 2012-01-04 浙江大东吴药业有限公司 Phenylethanoid glycoside components, and preparation method and application thereof

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KR20050031054A (en) * 2003-09-27 2005-04-01 대한민국 (소관: 제주대학교) Composition comprising the extract of eurya emarginata or the compounds isolated therefrom having anti-inflammatory activity
CN102304156A (en) * 2011-06-24 2012-01-04 浙江大东吴药业有限公司 Phenylethanoid glycoside components, and preparation method and application thereof

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