A monoterpene lactone compound and its preparation method and use in preparing anti-complement drugs

Abstract

The present invention relates to a monoterpene lactone compound and a preparation method thereof and use thereof in preparing an anti-complement drug. The monoterpene lactone compound has a chemical structure of the following general structural formula: the R group is any one of n-hexyl, n-heptyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl or 4-ene-pentadecyl. The present invention applies modern pharmacological research methods to test the anti-complement activity of the isolated monoterpene lactone compound. Eight monoterpene lactone components are isolated from the petroleum ether extraction part of the ethanol extract of the dried mature peel of the Cucurbitaceae plant Trichosanthes kirilowii Maxim., and it is confirmed that the monoterpene lactone components have a strong inhibitory effect on the classical pathway of the complement system, and can be further used to prepare anti-complement drugs.

Description

Technical Field

[0001] The invention relates to the field of traditional Chinese medicine pharmacy, and in particular to a monoterpene lactone compound and a preparation method thereof and use thereof in preparing an anti-complement drug. Background Art

[0002] Trichosanthes peel is derived from the dried mature peel of the plant Trichosanthes kirilowii Maxim. or Trichosanthes rosthornii Harms of the Cucurbitaceae family. The main effects of Trichosanthes peel are clearing away heat and resolving phlegm, promoting qi and relieving chest tightness. It is mainly used clinically to treat phlegm-heat cough, chest tightness and flank pain. Modern pharmacological studies have shown that Trichosanthes peel has multiple pharmacological effects such as anti-inflammatory, antibacterial, antiviral, improving cardiovascular system and anti-oxidation.

[0003] Further analysis shows that most of these diseases treated by Trichosanthes peel and their pharmacological activities are related to the complement system. As an important part of the body's immune system, the complement system participates in the body's specific and nonspecific immune mechanisms. It plays an important role in the body's antimicrobial defense response, the dissolution of immune complexes, the enhancement of humoral immune response, and the injurious response of mediating immunopathology. If the complement system is overactivated, it will not only consume a large amount of complement components, which will reduce the body's anti-infection ability, but also produce a large amount of bioactive substances, causing the body to have a serious inflammatory response, thereby causing a pathological damage process. Therefore, it is of great value and significance to find highly efficient and low-toxic complement inhibitors from traditional Chinese medicine to treat these diseases related to the overactivation of the complement system. Summary of the invention

[0004] The purpose of the present invention is to provide a monoterpene lactone compound with anti-complement activity and a preparation method thereof and use thereof in the preparation of anti-complement drugs.

[0005] The purpose of the present invention can be achieved by the following technical solutions:

[0006] The inventors found that the ethanol extract of Trichosanthes peel had significant anti-complement activity when conducting an in vitro anti-complement activity test screening. Therefore, an activity-oriented separation method was adopted to isolate 8 monoterpene lactone compounds from Trichosanthes peel, which had good anti-complement activity.

[0007] One of the objects of the present invention is a monoterpene lactone compound having a chemical structure of the following general formula:

[0008]

[0009] The R group is any one of n-hexyl, n-heptyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl or 4-ene-pentadecyl.

[0010] Further:

[0011] The R group is n-hexyl, and the compound is trichosanate D;

[0012] The R group is n-heptyl, and the compound is trichosanate E;

[0013] The R group is decyl, and the compound is trichosanate F;

[0014] The R group is dodecyl, and the compound is hemerolide A;

[0015] The R group is tetradecyl, and the compound is hemerolide B;

[0016] The R group is hexadecyl, and the compound is (–)-3-O-palmitoylloliolide;

[0017] The R group is octadecyl and the compound is trichosanate G;

[0018] The R group is 4-ene-pentadecyl and the compound is (3S,5R)-3-O-trans-5-pentadecenyl-loliolide.

[0019] Further:

[0020] The R group is n-hexyl, and the compound is trichosanate D;

[0021] The R group is n-heptyl, and the compound is trichosanate E;

[0022] The R group is decyl, and the compound is trichosanate F;

[0023] The R group is octadecyl and the compound is trichosanate G.

[0024] Combination Figure 1, trichosanate D is compound 1, trichosanate E is compound 2, trichosanate F is compound 3, hemerolide A is compound 4, hemerolide B is compound 5, (–)-3-O-palmitoylloliolide is compound 6, trichosanate G is compound 7, and (3S,5R)-3-O-trans-5-pentadecenyl-loliolide is compound 8.

[0025] Compound 1, trichosanate D: colorless oil; molecular formula: C 17 H 26 O4; relative molecular weight: 294; 1 H NMR (400MHz, CD3OD), δ: 5.83 (1H, s, H-7), 5.27 (1H, m, H-3), 2.50 (1H, dt, J = 14.2, 2.4Hz, H-4a),2.38(2H,t,J=7.4Hz,H-2'),2.06(1H,dt,J=15.0,2.5Hz,H-2a),1.88(1H,dd,J=14 .2,4.1Hz,H-4b),1.72(3H,s,H-11),1.68(1H,m,H-2b),1.64(2H,m,H-3'),1.43(3H,s,H- 9),1.35(2H,m,H-4'),1.35(2H,m,H-5'),1.31(3H,s,H-10),0.92(3H,t,J=7.0Hz,H-6'); 13 C NMR(100MHz,CD3OD)δ:183.9(C-6),174.1(C-1'),173.9(C-8),114.1(C-7),87.9(C-5),70.1(C-3),45.1(C-2),43.8(C -4),36.9(C-1),35.5(C-2'),32.4(C-4'),30.8(C-10),27.0(C-11),26.5(C-9),25.6(C-3'),23.4(C-5'),14.2(C-6').

[0026] Compound 2, trichosanate E: colorless oil; molecular formula: C 19 H 30 O4; relative molecular weight: 322; 1H NMR(400MHz,CD3OD),δ:5.82(1H,s,H-7),5.27(1H,m,H-3),2.50(1H,dt,J=14.3,2.5H z,H-4a),2.38(2H,t,J=7.4Hz,H-2'),2.06(1H,dt,J=15.0,2.5Hz,H-2a),1.88(1H,dd ,J=14.3,4.2Hz,H-4b),1.72(3H,s,H-11),1.68(1H,m,H-2b),1.65(2H,m,H-3'),1.43 (3H,s,H-9),1.31(3H,s,H-10),1.31(8H,m,H-4'–H-7'),0.90(3H,t,J=7.0Hz,H-8'); 13 CNMR(100MHz,CD3OD)δ:183.9(C-6),174.1(C-1'),173.8(C-8),114.1(C-7),87.9(C-5),70.1(C-3),45.1(C-2),43.8(C-4),36.9(C- 1),35.5(C-2'),32.8(C-6'),30.7(C-10),30.0(C-4'),30.1(C-5'),27.0(C-11),26.5(C-9),25.9(C-3'),23.6(C-7'),14.4(C-8').

[0027] Compound 3, trichosanate F: colorless oil; molecular formula: C 21 H 34 O4; relative molecular weight: 350; 1 H NMR(400MHz,CD3OD),δ:5.82(1H,s,H-7),5.27(1H,m,H-3),2.50(1H,dt,J=14.3,2.4H z,H-4a),2.38(2H,t,J=7.4Hz,H-2'),2.05(1H,dt,J=15.0,2.5Hz,H-2a),1.88(1H,dd, J=14.3,4.2Hz,H-4b),1.72(3H,s,H-11),1.68(1H,m,H-2b),1.65(2H,m,H-3'),1.43( 3H,s,H-9),1.33(3H,s,H-10),1.31(12H,m,H-4'–H-9'),0.89(3H,t,J=7.0Hz,H-10'); 13CNMR(100MHz,CD3OD)δ:183.9(C-6),174.1(C-1'),173.8(C-8),114.1(C-7),87.9(C-5),70.1(C-3),45.1(C-2),43.8(C-4),36.9 (C-1),35.5(C-2'),33.0(C-8'),30.8(C-10),30.4(C-4'–C-7'),27.0(C-11),26.5(C-9),25.9(C-3'),23.7(C-9'),14.4(C-10').

[0028] Compound 4, hemerolide A: colorless oil; molecular formula: C 23 H 38 O4; relative molecular weight: 378; 1 H NMR(400MHz,CD3OD),δ:5.83(1H,s,H-7),5.27(1H,m,H-3),2.50(1H,dt,J=14.2,2.4H z,H-4a),2.38(2H,t,J=7.4Hz,H-2'),2.06(1H,dd,J=15.0,2.5Hz,H-2a),1.88(1H,dd, J=14.2,4.1Hz,H-4b),1.72(3H,s,H-11),1.68(1H,m,H-2b),1.64(2H,m,H-3'),1.43(3 H,s,H-9),1.31(3H,s,H-10),1.30(16H,m,H-4'–H-11'),0.92(3H,t,J=7.0Hz,H-12'); 13 C NMR(100MHz,CD3OD)δ:183.7(C-6),174.0(C-1'),173.7(C-8),114.2(C-7),87.8(C-5),70.0(C-3),45.1(C-2),43.8(C-4),36.9(C -1),35.5(C-2'),33.0(C-10'),30.8(C-10),30.4(C-4'–C-9'),27.1(C-11),26.6(C-9),25.9(C-3'),23.7(C-11'),14.5(C-12').

[0029] Compound 5, hemerolide B: colorless oil; molecular formula: C 25 H 42 O4; relative molecular weight: 406; 1H NMR(400MHz,CD3OD),δ:5.82(1H,s,H-7),5.24(1H,m,H-3),2.47(1H,dt,J=14.3,2.5H z,H-4a),2.31(2H,t,J=7.4Hz,H-2'),2.02(1H,dd,J=15.0,2.5Hz,H-2a),1.80(1H,dd, J=14.4,4.3Hz,H-4b),1.69(3H,s,H-11),1.54(1H,m,H-2b),1.62(2H,m,H-3'),1.37(3 H,s,H-9),1.26(3H,s,H-10),1.25(20H,m,H-4'–H-13'),0.84(3H,t,J=7.0Hz,H-14'); 13 C NMR(100MHz,CD3OD)δ:181.2(C-6),172.6(C-1'),171.4(C-8),113.5(C-7),85.9(C-5),68.4(C-3),44.4(C-2),43.1(C-4),35.8(C -1),34.8(C-2'),32.0(C-12'),30.5(C-10),29.6(C-4'–C-11'),27.0(C-11),26.1(C-9),24.9(C-3'),22.7(C-13'),14.2(C-14').

[0030] Compound 6, (–)-3-O-palmitoylloliolide: colorless oil; molecular formula: C 27 H 46 O4; relative molecular weight: 434; 1 H NMR(400MHz,CD3OD),δ:5.82(1H,s,H-7),5.27(1H,m,H-3),2.50(1H,dt,J=14.3,2.4H z,H-4a),2.38(2H,t,J=7.4Hz,H-2'),2.06(1H,dd,J=15.0,2.5Hz,H-2a),1.88(1H,dd, J=14.3,4.2Hz,H-4b),1.72(3H,s,H-11),1.68(1H,m,H-2b),1.65(2H,m,H-3'),1.43(3 H,s,H-9),1.30(3H,s,H-10),1.30(24H,m,H-4'–H-15'),0.89(3H,t,J=7.0Hz,H-16'); 13C NMR(100MHz,CD3OD)δ:183.9(C-6),174.1(C-1'),173.8(C-8),114.2(C-7),87.9(C-5),70.1(C-3),45.1(C-2),43.8(C-4),36.9(C -1),35.5(C-2'),33.1(C-14'),30.8(C-10),30.6(C-4'–C-13'),27.1(C-11),26.5(C-9),25.9(C-3'),23.7(C-15'),14.4(C-16').

[0031] Compound 7, trichosanate G: colorless oil; molecular formula: C 29 H 50 O4; relative molecular weight: 462; 1 H NMR (400MHz, CDCl3), δ: 5.73 (1H, s, H-7), 5.26 (1H, m, H-3), 2.50 (1H, dt, J = 14.4, 2.6H z,H-4a),2.32(2H,t,J=7.4Hz,H-2'),2.05(1H,dt,J=14.8,2.5Hz,H-2a),1.88(1H,dd, J=14.3,4.2Hz,H-4b),1.71(3H,s,H-11),1.56(1H,m,H-2b),1.64(2H,m,H-3'),1.39(3 H,s,H-9),1.29(3H,s,H-10),1.25(28H,m,H-4'–H-17'),0.87(3H,t,J=6.9Hz,H-18'); 13 C NMR(100MHz, CDCl3)δ:181.3(C-6),172.7(C-1'),171.5(C-8),113.6(C-7),86.0(C-5),68.5(C-3),44.4(C-2),43.1(C-4),35.9(C -1),34.9(C-2'),32.0(C-16'),30.6(C-10),29.3(C-4'–C-15'),26.7(C-11),26.1(C-9),25.0(C-3'),22.8(C-17'),14.3(C-18').

[0032] Compound 8, (3S,5R)-3-O-trans-5-pentadecenyl-loliolide: colorless oil; molecular formula: C 26 H 42 O4; relative molecular weight: 418;1 H NMR(400MHz, CD3OD), δ:5.82(1H,s,H-7),5.45(1H,dt,J=15.4,6.3Hz,H-6'),5.38(1H,dt,J=15.6,6.3Hz,H-5'),5.26 (1H,m,H-3),2.50(1H,dt,J=14.3,2.4Hz,H-4a),2.37(2H,t,J=7.5Hz,H-2'),2.05(1H,dd,J=14.3,2.4Hz,H-2a),2.00 (2H,m,H-4'),2.00(2H,m,H-7'),1.88(1H,dd,J=14.4,4.3Hz,H-4b),1.72(3H,s,H-11),1.66(1H,dd,J=13.3,3.0Hz,H -2b),1.42(3H,s,H-9),1.31(3H,s,H-10),1.29(14H,m,H-8'–H-14'),1.19(2H,m,H-3'),0.90(3H,t,J=6.9Hz,H-15'); 13 C NMR (100MHz, CD3OD) δ: 183.8 (C-6), 173.7 (C-1'), 173.9 (C-8), 132.8 (C-6'), 130.2 (C-5'), 114.2 (C-7), 87.8 (C-5), 70.0 (C-3), 45.1 (C-2), 43. 8(C-4),36.9(C-1),34.7(C-2'),33.6(C-7'),33.1(C-4'),30.8(C-10), 30.5(C-8'–C-14'),27.1(C-11),26.6(C-9),25.7(C-3'),14.5(C-15').

[0033] The second object of the present invention is a method for preparing the monoterpene lactone compound as described above, the preparation method comprising the following steps:

[0034] After the peel of Trichosanthes kirilowii is crushed, it is subjected to percolation extraction, and after the extract is concentrated, it is suspended in water, and extracted with petroleum ether, ethyl acetate, and n-butanol in sequence to obtain a petroleum ether extract, an ethyl acetate extract, and an n-butanol extract;

[0035] The petroleum ether extract was separated by silica gel column chromatography, and eluted with petroleum ether-ethyl acetate gradient to obtain 5 fractions A1-A5; the A2 fraction was separated by silica gel column chromatography, and eluted with n-hexane-ethyl acetate gradient to obtain 12 fractions A2A-A2L; the A2G fraction was separated by reversed phase ODS column chromatography, and eluted with methanol-water gradient to obtain 14 fractions A2G1-A2G14;

[0036] Fraction A2G5 was purified by semi-preparative liquid phase, and compound hemerolide A was obtained by isocratic elution with methanol-water as the mobile phase; fraction A2G7 was purified by semi-preparative liquid phase, and compound hemerolide B and (–)-3-O-palmitoylloliolide were obtained by isocratic elution with methanol-water as the mobile phase; fraction A2G8 was purified by semi-preparative liquid phase, and compound trichosanate G was obtained by isocratic elution with methanol-water as the mobile phase;

[0037] The A2H fraction was separated by reverse phase ODS column chromatography and eluted with a methanol-water gradient to obtain 11 fractions A2H1–A2H11;

[0038] Fraction A2H2 was purified by semi-preparative liquid phase, and acetonitrile-water was used as the mobile phase for isocratic elution to obtain compound trichosanate D; fraction A2H3 was purified by semi-preparative liquid phase, and acetonitrile-water was used as the mobile phase for isocratic elution to obtain compound trichosanate E; fraction A2H4 was purified by semi-preparative liquid phase, and acetonitrile-water was used as the mobile phase for isocratic elution to obtain compound trichosanate F; fraction A2H6 was purified by semi-preparative liquid phase, and acetonitrile-water was used as the mobile phase for isocratic elution to obtain compound (3S,5R)-3-O-trans-5-pentadecenyl-loliolide.

[0039] Furthermore, the specific steps of the preparation method are as follows:

[0040] After the peel of Trichosanthes kirilowii is crushed, it is subjected to percolation extraction with ethanol, the extract is concentrated under reduced pressure, the concentrated extract is suspended in water, and extracted with petroleum ether, ethyl acetate, and n-butanol in sequence to obtain a petroleum ether extract, an ethyl acetate extract, and an n-butanol extract;

[0041] The petroleum ether extract was separated by silica gel column chromatography and eluted with petroleum ether-ethyl acetate (1:0→0:1, v / v) gradient to obtain 5 fractions A1–A5; the A2 fraction was separated by silica gel column chromatography and eluted with n-hexane-ethyl acetate (100:0→1:10, v / v) gradient to obtain 12 fractions A2A–A2L; the A2G fraction was separated by reversed phase ODS column chromatography and eluted with methanol-water (80:20→100:0, v / v) gradient to obtain 14 fractions A2G1–A2G14;

[0042] Fraction A2G5 was purified by semi-preparative liquid phase, and compound hemerolide A was obtained by isocratic elution with methanol-water (90:10, v / v) as the mobile phase; fraction A2G7 was purified by semi-preparative liquid phase, and compound hemerolide B and (–)-3-O-palmito ylloliolide were obtained by isocratic elution with methanol-water (95:5, v / v) as the mobile phase; fraction A2G8 was purified by semi-preparative liquid phase, and compound trichosanate G was obtained by isocratic elution with methanol-water (97.5:2.5, v / v) as the mobile phase;

[0043] The A2H fraction was separated by reversed-phase ODS column chromatography and eluted with a gradient of methanol-water (80:20→100:0, v / v) to obtain 11 fractions A2H1–A2H11;

[0044] Fraction A2H2 was purified by semi-preparative liquid phase, and acetonitrile-water (70:30, v / v) was used as the mobile phase for isocratic elution to obtain compound trichosanate D; fraction A2H3 was purified by semi-preparative liquid phase, and acetonitrile-water (84:16, v / v) was used as the mobile phase for isocratic elution to obtain compound trichosanate E (2); fraction A2H4 was purified by semi-preparative liquid phase, and acetonitrile-water (90:10, v / v) was used as the mobile phase for isocratic elution to obtain compound trichosanate F; fraction A2H6 was purified by semi-preparative liquid phase, and acetonitrile-water (95:5, v / v) was used as the mobile phase for isocratic elution to obtain compound (3S,5R)-3-O-trans-5-pentadecenyl-loliolide.

[0045] Furthermore, the mesh size of the silica gel in the silica gel column chromatography separation is 200-300 meshes.

[0046] Furthermore, the concentration of the ethanol is 95% (v / v).

[0047] The third object of the present invention is to use the monoterpene lactone compound as described above in the preparation of anti-complement drugs.

[0048] Furthermore, the monoterpene lactone compound inhibits the classical pathway of the complement system.

[0049] The present invention uses modern pharmacological research methods to test the anti-complement activity of the isolated monoterpene lactone compounds. Eight monoterpene lactone components are isolated from the petroleum ether extraction part of the ethanol extract of the dried mature pericarp of the Cucurbitaceae plant Trichosanthes kirilowii Maxim., and it is confirmed that they have a strong inhibitory effect on the classical pathway of the complement system, and can be further used to prepare anti-complement drugs. BRIEF DESCRIPTION OF THE DRAWINGS

[0050] Figure 1 Flow chart of the extraction and separation of monoterpene lactone compounds 1-8 in the examples. DETAILED DESCRIPTION

[0051] The present invention is described in detail below in conjunction with the accompanying drawings and specific embodiments. This embodiment is implemented based on the technical solution of the present invention, and provides a detailed implementation method and specific operation process, but the protection scope of the present invention is not limited to the following embodiments.

[0052] A monoterpene lactone compound, the monoterpene lactone compound has a chemical structure of the following general structural formula:

[0053]

[0054] The R group is any one of n-hexyl, n-heptyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl or 4-ene-pentadecyl.

[0055] Example

[0056] 1. Extraction and Isolation of Monoterpene Lactones 1–8 from Trichosanthes Peel

[0057] 31.0 kg of Trichosanthes peel was taken, mechanically crushed, and then percolated with 95% (v / v) ethanol. The extract was concentrated under reduced pressure, and the concentrate was suspended in water, and extracted with petroleum ether, ethyl acetate, and n-butanol in sequence to obtain a petroleum ether extract, an ethyl acetate extract, and an n-butanol extract, wherein the petroleum ether extract had 611 g;

[0058] 600 g of petroleum ether extract was separated by silica gel column chromatography, and eluted with petroleum ether-ethyl acetate (1:0→0:1, v / v) gradient to obtain 5 fractions A1-A5; the A2 fraction was separated by silica gel column chromatography, and eluted with n-hexane-ethyl acetate (100:0→1:10, v / v) gradient to obtain 12 fractions A2A-A2L; the A2G fraction was separated by reversed phase ODS column chromatography, and eluted with methanol-water (80:20→100:0, v / v) gradient to obtain 14 fractions A2G1-A2G14;

[0059] Fraction A2G5 was purified by semi-preparative liquid phase, and compound hemerolide A was obtained by isocratic elution with methanol-water (90:10, v / v) as the mobile phase; fraction A2G7 was purified by semi-preparative liquid phase, and compound hemerolide B and (–)-3-O-palmito ylloliolide were obtained by isocratic elution with methanol-water (95:5, v / v) as the mobile phase; fraction A2G8 was purified by semi-preparative liquid phase, and compound trichosanate G was obtained by isocratic elution with methanol-water (97.5:2.5, v / v) as the mobile phase;

[0060] The A2H fraction was separated by reversed-phase ODS column chromatography and eluted with a gradient of methanol-water (80:20→100:0, v / v) to obtain 11 fractions A2H1–A2H11;

[0061] Fraction A2H2 was purified by semi-preparative liquid phase, and acetonitrile-water (70:30, v / v) was used as the mobile phase for isocratic elution to obtain compound trichosanate D; fraction A2H3 was purified by semi-preparative liquid phase, and acetonitrile-water (84:16, v / v) was used as the mobile phase for isocratic elution to obtain compound trichosanate E; fraction A2H4 was purified by semi-preparative liquid phase, and acetonitrile-water (90:10, v / v) was used as the mobile phase for isocratic elution to obtain compound trichosanate F; fraction A2H6 was purified by semi-preparative liquid phase, and acetonitrile-water (95:5, v / v) was used as the mobile phase for isocratic elution to obtain compound (3S,5R)-3-O-trans-5-pentadecenyl-loliolide.

[0062] Among them, the mesh number of silica gel in silica gel column chromatography separation is 200-300 mesh.

[0063] Combination Figure 1, trichosanate D is compound 1, trichosanate E is compound 2, trichosanate F is compound 3, hemerolide A is compound 4, hemerolide B is compound 5, (–)-3-O-palmitoylloliolide is compound 6, trichosanate G is compound 7, and (3S,5R)-3-O-trans-5-pentadecenyl-loliolide is compound 8.

[0064] Compound 1, trichosanate D: colorless oil; molecular formula: C 17 H 26 O4; relative molecular weight: 294; 1 H NMR (400MHz, CD3OD), δ: 5.83 (1H, s, H-7), 5.27 (1H, m, H-3), 2.50 (1H, dt, J = 14.2, 2.4Hz, H-4a),2.38(2H,t,J=7.4Hz,H-2'),2.06(1H,dt,J=15.0,2.5Hz,H-2a),1.88(1H,dd,J=14 .2,4.1Hz,H-4b),1.72(3H,s,H-11),1.68(1H,m,H-2b),1.64(2H,m,H-3'),1.43(3H,s,H- 9),1.35(2H,m,H-4'),1.35(2H,m,H-5'),1.31(3H,s,H-10),0.92(3H,t,J=7.0Hz,H-6'); 13 C NMR(100MHz,CD3OD)δ:183.9(C-6),174.1(C-1'),173.9(C-8),114.1(C-7),87.9(C-5),70.1(C-3),45.1(C-2),43.8(C -4),36.9(C-1),35.5(C-2'),32.4(C-4'),30.8(C-10),27.0(C-11),26.5(C-9),25.6(C-3'),23.4(C-5'),14.2(C-6').

[0065] Compound 2, trichosanate E: colorless oil; molecular formula: C 19 H 30 O4; relative molecular weight: 322; 1H NMR(400MHz,CD3OD),δ:5.82(1H,s,H-7),5.27(1H,m,H-3),2.50(1H,dt,J=14.3,2.5H z,H-4a),2.38(2H,t,J=7.4Hz,H-2'),2.06(1H,dt,J=15.0,2.5Hz,H-2a),1.88(1H,dd ,J=14.3,4.2Hz,H-4b),1.72(3H,s,H-11),1.68(1H,m,H-2b),1.65(2H,m,H-3'),1.43 (3H,s,H-9),1.31(3H,s,H-10),1.31(8H,m,H-4'–H-7'),0.90(3H,t,J=7.0Hz,H-8'); 13 CNMR(100MHz,CD3OD)δ:183.9(C-6),174.1(C-1'),173.8(C-8),114.1(C-7),87.9(C-5),70.1(C-3),45.1(C-2),43.8(C-4),36.9(C- 1),35.5(C-2'),32.8(C-6'),30.7(C-10),30.0(C-4'),30.1(C-5'),27.0(C-11),26.5(C-9),25.9(C-3'),23.6(C-7'),14.4(C-8').

[0066] Compound 3, trichosanate F: colorless oil; molecular formula: C 21 H 34 O4; relative molecular weight: 350; 1 H NMR(400MHz,CD3OD),δ:5.82(1H,s,H-7),5.27(1H,m,H-3),2.50(1H,dt,J=14.3,2.4H z,H-4a),2.38(2H,t,J=7.4Hz,H-2'),2.05(1H,dt,J=15.0,2.5Hz,H-2a),1.88(1H,dd, J=14.3,4.2Hz,H-4b),1.72(3H,s,H-11),1.68(1H,m,H-2b),1.65(2H,m,H-3'),1.43( 3H,s,H-9),1.33(3H,s,H-10),1.31(12H,m,H-4'–H-9'),0.89(3H,t,J=7.0Hz,H-10'); 13CNMR(100MHz,CD3OD)δ:183.9(C-6),174.1(C-1'),173.8(C-8),114.1(C-7),87.9(C-5),70.1(C-3),45.1(C-2),43.8(C-4),36.9 (C-1),35.5(C-2'),33.0(C-8'),30.8(C-10),30.4(C-4'–C-7'),27.0(C-11),26.5(C-9),25.9(C-3'),23.7(C-9'),14.4(C-10').

[0067] Compound 4, hemerolide A: colorless oil; molecular formula: C 23 H 38 O4; relative molecular weight: 378; 1 H NMR(400MHz,CD3OD),δ:5.83(1H,s,H-7),5.27(1H,m,H-3),2.50(1H,dt,J=14.2,2.4H z,H-4a),2.38(2H,t,J=7.4Hz,H-2'),2.06(1H,dd,J=15.0,2.5Hz,H-2a),1.88(1H,dd, J=14.2,4.1Hz,H-4b),1.72(3H,s,H-11),1.68(1H,m,H-2b),1.64(2H,m,H-3'),1.43(3 H,s,H-9),1.31(3H,s,H-10),1.30(16H,m,H-4'–H-11'),0.92(3H,t,J=7.0Hz,H-12'); 13 C NMR(100MHz,CD3OD)δ:183.7(C-6),174.0(C-1'),173.7(C-8),114.2(C-7),87.8(C-5),70.0(C-3),45.1(C-2),43.8(C-4),36.9(C -1),35.5(C-2'),33.0(C-10'),30.8(C-10),30.4(C-4'–C-9'),27.1(C-11),26.6(C-9),25.9(C-3'),23.7(C-11'),14.5(C-12').

[0068] Compound 5, hemerolide B: colorless oil; molecular formula: C 25 H 42 O4; relative molecular weight: 406; 1H NMR(400MHz,CD3OD),δ:5.82(1H,s,H-7),5.24(1H,m,H-3),2.47(1H,dt,J=14.3,2.5H z,H-4a),2.31(2H,t,J=7.4Hz,H-2'),2.02(1H,dd,J=15.0,2.5Hz,H-2a),1.80(1H,dd, J=14.4,4.3Hz,H-4b),1.69(3H,s,H-11),1.54(1H,m,H-2b),1.62(2H,m,H-3'),1.37(3 H,s,H-9),1.26(3H,s,H-10),1.25(20H,m,H-4'–H-13'),0.84(3H,t,J=7.0Hz,H-14'); 13 C NMR(100MHz,CD3OD)δ:181.2(C-6),172.6(C-1'),171.4(C-8),113.5(C-7),85.9(C-5),68.4(C-3),44.4(C-2),43.1(C-4),35.8(C -1),34.8(C-2'),32.0(C-12'),30.5(C-10),29.6(C-4'–C-11'),27.0(C-11),26.1(C-9),24.9(C-3'),22.7(C-13'),14.2(C-14').

[0069] Compound 6, (–)-3-O-palmitoylloliolide: colorless oil; molecular formula: C 27 H 46 O4; relative molecular weight: 434; 1 H NMR(400MHz,CD3OD),δ:5.82(1H,s,H-7),5.27(1H,m,H-3),2.50(1H,dt,J=14.3,2.4H z,H-4a),2.38(2H,t,J=7.4Hz,H-2'),2.06(1H,dd,J=15.0,2.5Hz,H-2a),1.88(1H,dd, J=14.3,4.2Hz,H-4b),1.72(3H,s,H-11),1.68(1H,m,H-2b),1.65(2H,m,H-3'),1.43(3 H,s,H-9),1.30(3H,s,H-10),1.30(24H,m,H-4'–H-15'),0.89(3H,t,J=7.0Hz,H-16'); 13C NMR(100MHz,CD3OD)δ:183.9(C-6),174.1(C-1'),173.8(C-8),114.2(C-7),87.9(C-5),70.1(C-3),45.1(C-2),43.8(C-4),36.9(C -1),35.5(C-2'),33.1(C-14'),30.8(C-10),30.6(C-4'–C-13'),27.1(C-11),26.5(C-9),25.9(C-3'),23.7(C-15'),14.4(C-16').

[0070] Compound 7, trichosanate G: colorless oil; molecular formula: C 29 H 50 O4; relative molecular weight: 462; 1 H NMR (400MHz, CDCl3), δ: 5.73 (1H, s, H-7), 5.26 (1H, m, H-3), 2.50 (1H, dt, J = 14.4, 2.6H z,H-4a),2.32(2H,t,J=7.4Hz,H-2'),2.05(1H,dt,J=14.8,2.5Hz,H-2a),1.88(1H,dd, J=14.3,4.2Hz,H-4b),1.71(3H,s,H-11),1.56(1H,m,H-2b),1.64(2H,m,H-3'),1.39(3 H,s,H-9),1.29(3H,s,H-10),1.25(28H,m,H-4'–H-17'),0.87(3H,t,J=6.9Hz,H-18'); 13 C NMR(100MHz, CDCl3)δ:181.3(C-6),172.7(C-1'),171.5(C-8),113.6(C-7),86.0(C-5),68.5(C-3),44.4(C-2),43.1(C-4),35.9(C -1),34.9(C-2'),32.0(C-16'),30.6(C-10),29.3(C-4'–C-15'),26.7(C-11),26.1(C-9),25.0(C-3'),22.8(C-17'),14.3(C-18').

[0071] Compound 8, (3S,5R)-3-O-trans-5-pentadecenyl-loliolide: colorless oil; molecular formula: C 26 H 42 O4; relative molecular weight: 418;1 H NMR(400MHz, CD3OD), δ:5.82(1H,s,H-7),5.45(1H,dt,J=15.4,6.3Hz,H-6'),5.38(1H,dt,J=15.6,6.3Hz,H-5'),5.26 (1H,m,H-3),2.50(1H,dt,J=14.3,2.4Hz,H-4a),2.37(2H,t,J=7.5Hz,H-2'),2.05(1H,dd,J=14.3,2.4Hz,H-2a),2.00 (2H,m,H-4'),2.00(2H,m,H-7'),1.88(1H,dd,J=14.4,4.3Hz,H-4b),1.72(3H,s,H-11),1.66(1H,dd,J=13.3,3.0Hz,H -2b),1.42(3H,s,H-9),1.31(3H,s,H-10),1.29(14H,m,H-8'–H-14'),1.19(2H,m,H-3'),0.90(3H,t,J=6.9Hz,H-15'); 13 C NMR (100MHz, CD3OD) δ: 183.8 (C-6), 173.7 (C-1'), 173.9 (C-8), 132.8 (C-6'), 130.2 (C-5'), 114.2 (C-7), 87.8 (C-5), 70.0 (C-3), 45.1 (C-2), 43. 8(C-4),36.9(C-1),34.7(C-2'),33.6(C-7'),33.1(C-4'),30.8(C-10), 30.5(C-8'–C-14'),27.1(C-11),26.6(C-9),25.7(C-3'),14.5(C-15').

[0072] 2. In vitro anti-complement classical pathway test

[0073] Take 0.1 mL of complement prepared with guinea pig serum, add barbiturate buffer (BBS) to prepare a 1:10 (v / v) solution, and then dilute with BBS to 1:20 (v / v), 1:40 (v / v), 1:80 (v / v), 1:160 (v / v), 1:320 (v / v), 1:640 (v / v) and 1:1280 (v / v) solutions. Take 0.1 mL of 1:1000 (v / v) hemolysin, each concentration of complement and 2% sheep red blood cells (SRBC) and dissolve in 0.3 mL BBS, mix well, place in a 37°C water bath for 30 minutes, then place in a low-temperature high-speed centrifuge and centrifuge at 5000 rpm and 4°C for 10 minutes. Take 0.2 mL of the supernatant from each tube and place it in a 96-well plate, and measure its absorbance at 405 nm. The experiment also set up a full hemolysis group (0.1mL 2% SRBC dissolved in 0.5mL distilled water). The absorbance of the distilled water-dissolved blood vessel was used as the full hemolysis standard to calculate the hemolysis rate. The complement dilution was used as the X-axis and the hemolysis percentage was used as the Y-axis for plotting. The lowest complement concentration that achieved a similar high hemolysis rate was selected as the critical complement concentration required to ensure that the system can hemolyze normally. Take the critical concentration of complement and mix it with the test sample of different concentrations, add appropriate amounts of BBS, hemolysin and 2% SRBC, and put it into a low-temperature high-speed centrifuge after 30 minutes of water bath at 37°C. After centrifugation at 5000rpm and 4°C for 10 minutes, take 0.2mL of the supernatant from each tube and put it in a 96-well plate, and measure the absorbance at 405nm. The experiment also set up a test sample control group, a complement group and a full hemolysis group. The hemolysis rate was calculated by deducting the absorbance value of the corresponding test sample control group from the absorbance value of the test sample. Plot the test sample concentration as the X-axis and the hemolysis inhibition rate as the Y-axis to calculate the test sample concentration required to inhibit hemolysis by 50% (CH 50 ). The results are shown in Table 1.

[0074] Table 1. Inhibitory effects of compounds 1-8 on the classical pathway of the complement system (Mean±SD, n=3)

[0075]

[0076] The results of the in vitro anti-complement activity test showed that the monoterpene lactone compounds 1-8 extracted and separated in this example had a strong inhibitory effect on the classical pathway of the complement system, and the minimum test sample concentration required for 50% hemolysis was 69.1-454.6 μg / mL.

[0077] The above is only a preferred embodiment of the present invention, and does not limit the present invention in other forms. Any technician familiar with the profession may use the above disclosed technical content to change or modify it into an equivalent embodiment with equivalent changes. However, any simple modification, equivalent change and modification made to the above embodiment according to the technical essence of the present invention without departing from the technical solution of the present invention still belongs to the protection scope of the technical solution of the present invention.

Claims

1. A method for preparing a monoterpene lactone compound, characterized in that: The specific steps of the preparation method are as follows: After the peel of Trichosanthes kirilowii is crushed, it is subjected to percolation extraction with ethanol, and after the extract is concentrated, it is suspended in water, and extracted with petroleum ether, ethyl acetate, and n-butanol in sequence to obtain a petroleum ether extract, an ethyl acetate extract, and an n-butanol extract; The petroleum ether extract was separated by silica gel column chromatography, and eluted with petroleum ether-ethyl acetate 1:0→0:1, v / v gradient to obtain 5 fractions A1-A5; the A2 fraction was separated by silica gel column chromatography, and eluted with n-hexane-ethyl acetate 100:0→1:10, v / v gradient to obtain 12 fractions A2A-A2L; the A2G fraction was separated by reversed phase ODS column chromatography, and eluted with methanol-water 80:20→100:0, v / v gradient to obtain 14 fractions A2G1-A2G14; Fraction A2G5 was purified by semi-preparative liquid phase, and compound hemerolide A was obtained by isocratic elution with methanol-water 90:10, v / v as the mobile phase; fraction A2G7 was purified by semi-preparative liquid phase, and compound hemerolide B and (–)-3-O-palmitoylloliolide were obtained by isocratic elution with methanol-water 95:5, v / v as the mobile phase; fraction A2G8 was purified by semi-preparative liquid phase, and compound trichosanate G was obtained by isocratic elution with methanol-water 97.5:2.5, v / v as the mobile phase; The A2H fraction was separated by reverse phase ODS column chromatography and eluted with a gradient of methanol-water 80:20→100:0, v / v to obtain 11 fractions A2H1–A2H11; Fraction A2H2 was purified by semi-preparative liquid phase, and acetonitrile-water 70:30, v / v was used as the mobile phase to isocratic elution to obtain compound trichosanate D; fraction A2H3 was purified by semi-preparative liquid phase, and acetonitrile-water 84:16, v / v was used as the mobile phase to isocratic elution to obtain compound trichosanate E; fraction A2H4 was purified by semi-preparative liquid phase, and acetonitrile-water 90:10, v / v was used as the mobile phase to isocratic elution to obtain compound trichosanate F; fraction A2H6 was purified by semi-preparative liquid phase, and acetonitrile-water 95:5, v / v was used as the mobile phase to isocratic elution to obtain compound (3 S ,5 R )-3-O-trans-5-pentadecenyl-loliolide; Compound 1, trichosanate D: colorless oil; molecular formula: C 17 H 26 O4; relative molecular weight: 294; 1 H NMR (400 MHz, CD3OD), δ : 5.83 (1H, s, H-7), 5.27 (1H, m, H-3), 2.50 (1H, dt, J =14.2, 2.4 Hz, H-4a), 2.38 (2H, t, J = 7.4 Hz, H-2'), 2.06 (1H, dt, J = 15.0,2.5 Hz, H-2a), 1.88 (1H, dd, J = 14.2, 4.1 Hz, H-4b), 1.72 (3H, s, H-11), 1.68(1H, m, H-2b), 1.64(2H, m, H-3'), 1.43 (3H, s, H-9), 1.35(2H, m, H-4'), 1.35(2H, m, H-5'), 1.31 (3H, s, H-10), 0.92 (3H, t, J = 7.0 Hz, H-6'); 13 C NMR (100 MHz, CD3OD) δ : 183.9 (C-6), 174.1 (C-1'), 173.9 (C-8), 114.1 (C-7), 87.9(C-5), 70.1 (C-3), 45.1 (C-2), 43.8 (C-4), 36.9 (C-1), 35.5 (C-2'), 32.4 (C-4'), 30.8 (C-10), 27.0 (C-11), 26.5 (C-9), 25.6 (C-3'), 23.4 (C-5'), 14.2 (C-6'); Compound 2, trichosanate E: colorless oil; molecular formula: C 19 H 30 O4; relative molecular weight: 322; 1 H NMR (400 MHz, CD3OD), δ : 5.82 (1H, s, H-7), 5.27 (1H, m, H-3), 2.50 (1H, dt, J =14.3, 2.5 Hz, H-4a), 2.38 (2H, t, J = 7.4 Hz, H-2'), 2.06 (1H, dt, J = 15.0,2.5 Hz, H-2a), 1.88 (1H, dd, J = 14.3, 4.2 Hz, H-4b), 1.72 (3H, s, H-11), 1.68(1H, m, H-2b), 1.65 (2H, m, H-3'), 1.43 (3H, s, H-9), 1.31 (3H, s, H-10), 1.31(8H, m, H-4'–H-7'), 0.90 (3H, t, J = 7.0 Hz, H-8'); 13 C NMR (100 MHz, CD3OD) δ :183.9 (C-6), 174.1 (C-1'), 173.8 (C-8), 114.1 (C-7), 87.9 (C-5), 70.1 (C-3), 45.1 (C-2), 43.8 (C-4), 36.9 (C-1), 35.5 (C-2'), 32.8 (C-6'),30.7 (C-10), 30.0 (C-4'), 30.1 (C-5'), 27.0 (C-11), 26.5 (C-9), 25.9 (C-3'),23.6 (C-7'), 14.4 (C-8'); Compound 3, trichosanate F: colorless oil; molecular formula: C 21 H 34 O4; relative molecular weight: 350; 1 H NMR (400MHz, CD3OD), δ : 5.82 (1H, s, H-7), 5.27 (1H, m, H-3), 2.50 (1H, dt, J = 14.3,2.4 Hz, H-4a), 2.38 (2H, t, J = 7.4 Hz, H-2'), 2.05 (1H, dt, J = 15.0, 2.5Hz, H-2a), 1.88 (1H, dd, J = 14.3, 4.2 Hz, H-4b), 1.72 (3H, s, H-11), 1.68(1H, m, H-2b), 1.65 (2H, m, H-3'), 1.43 (3H, s, H-9), 1.33 (3H, s, H-10), 1.31(12H, m, H-4'–H-9'), 0.89 (3H, t, J = 7.0 Hz, H-10'); 13 C NMR (100 MHz, CD3OD) δ :183.9 (C-6), 174.1 (C-1'), 173.8 (C-8), 114.1 (C-7), 87.9 (C-5), 70.1 (C-3), 45.1 (C-2), 43.8 (C-4), 36.9 (C-1), 35.5 (C-2'), 33.0 (C-8'), 30.8 (C-10), 30.4 (C-4'–C-7'), 27.0 (C-11), 26.5 (C-9), 25.9 (C-3'), 23.7 (C-9'), 14.4 (C-10'); Compound 4, hemerolide A: colorless oil; molecular formula: C 23 H 38 O4; relative molecular weight: 378; 1 H NMR (400MHz, CD3OD), δ : 5.83 (1H, s, H-7), 5.27 (1H, m, H-3), 2.50 (1H, dt, J = 14.2,2.4 Hz, H-4a), 2.38 (2H, t, J = 7.4 Hz, H-2'), 2.06 (1H, dd, J = 15.0, 2.5Hz, H-2a), 1.88 (1H, dd, J = 14.2, 4.1 Hz, H-4b), 1.72 (3H, s, H-11), 1.68(1H, m, H-2b), 1.64 (2H, m, H-3'), 1.43 (3H, s, H-9), 1.31 (3H, s, H-10), 1.30(16H, m, H-4'–H-11'), 0.92 (3H, t, J = 7.0 Hz, H-12'); 13 C NMR (100 MHz, CD3OD) δ :183.7 (C-6), 174.0 (C-1'), 173.7 (C-8), 114.2 (C-7), 87.8 (C-5), 70.0 (C-3), 45.1 (C-2), 43.8 (C-4), 36.9 (C-1), 35.5 (C-2'), 33.0 (C-10'), 30.8 (C-10), 30.4 (C-4'–C-9'), 27.1 (C-11), 26.6 (C-9), 25.9 (C-3'), 23.7 (C-11'), 14.5 (C-12'); Compound 5, hemerolide B: colorless oil; molecular formula: C 25 H 42 O4; relative molecular weight: 406; 1 H NMR (400MHz, CD3OD), δ : 5.82 (1H, s, H-7), 5.24 (1H, m, H-3), 2.47 (1H, dt, J = 14.3,2.5 Hz, H-4a), 2.31 (2H, t, J = 7.4 Hz, H-2'), 2.02 (1H, dd, J = 15.0, 2.5Hz, H-2a), 1.80 (1H, dd, J = 14.4, 4.3 Hz, H-4b), 1.69 (3H, s, H-11), 1.54(1H, m, H-2b), 1.62 (2H, m, H-3'), 1.37 (3H, s, H-9), 1.26 (3H, s, H-10), 1.25(20H, m, H-4'–H-13'), 0.84 (3H, t, J = 7.0 Hz, H-14'); 13 C NMR (100 MHz, CD3OD) δ :181.2 (C-6), 172.6 (C-1'), 171.4 (C-8), 113.5 (C-7), 85.9 (C-5), 68.4 (C-3), 44.4 (C-2), 43.1 (C-4), 35.8 (C-1), 34.8 (C-2'), 32.0 (C-12'), 30.5 (C-10), 29.6 (C-4'–C-11'), 27.0 (C-11), 26.1 (C-9), 24.9 (C-3'), 22.7 (C-13'), 14.2 (C-14'); Compound 6, (–)-3-O-palmitoylloliolide: colorless oil; molecular formula: C 27 H 46 O4; relative molecular weight: 434; 1 H NMR (400 MHz, CD3OD), δ : 5.82 (1H, s, H-7), 5.27 (1H, m, H-3), 2.50(1H, dt, J = 14.3, 2.4 Hz, H-4a), 2.38 (2H, t, J = 7.4 Hz, H-2'), 2.06 (1H,dd, J = 15.0, 2.5 Hz, H-2a), 1.88 (1H, dd, J = 14.3, 4.2 Hz, H-4b), 1.72 (3H,s, H-11), 1.68 (1H, m, H-2b), 1.65 (2H, m, H-3'), 1.43 (3H, s, H-9), 1.30(3H, s, H-10), 1.30(24H, m, H-4'–H-15'), 0.89 (3H, t, J = 7.0 Hz, H-16'); 13 CNMR (100 MHz, CD3OD) δ :183.9 (C-6), 174.1 (C-1'), 173.8 (C-8), 114.2 (C-7), 87.9 (C-5), 70.1 (C-3), 45.1 (C-2), 43.8 (C-4), 36.9 (C-1), 35.5 (C-2'), 33.1(C-14'), 30.8 (C-10), 30.6 (C-4'–C-13'), 27.1 (C-11), 26.5 (C-9), 25.9 (C-3'), 23.7 (C-15'), 14.4 (C-16'); Compound 7, trichosanate G: colorless oil; molecular formula: C 29 H 50 O4; relative molecular weight: 462; 1 H NMR (400MHz, CDCl3), δ : 5.73 (1H, s, H-7), 5.26 (1H, m, H-3), 2.50 (1H, dt, J = 14.4,2.6 Hz, H-4a), 2.32 (2H, t, J = 7.4 Hz, H-2'), 2.05 (1H, dt, J = 14.8, 2.5Hz, H-2a), 1.88 (1H, dd, J = 14.3, 4.2 Hz, H-4b), 1.71 (3H, s, H-11), 1.56(1H, m, H-2b), 1.64 (2H, m, H-3'), 1.39 (3H, s, H-9), 1.29 (3H, s, H-10), 1.25(28H, m, H-4'–H-17'), 0.87 (3H, t, J = 6.9 Hz, H-18'); 13 C NMR (100 MHz,CDCl3) δ :181.3 (C-6), 172.7 (C-1'), 171.5 (C-8), 113.6 (C-7), 86.0 (C-5), 68.5 (C-3), 44.4 (C-2), 43.1 (C-4), 35.9 (C-1), 34.9 (C-2'), 32.0 (C-16'), 30.6 (C-10), 29.3 (C-4'–C-15'), 26.7 (C-11), 26.1 (C-9), 25.0 (C-3'), 22.8 (C-17'), 14.3 (C-18'); Compound 8, (3 S ,5 R )-3-O-trans-5-pentadecenyl-loliolide: colorless oil; molecular formula: C 26 H 42 O4; relative molecular weight: 418; 1 H NMR (400 MHz, CD3OD), δ : 5.82 (1H, s, H-7), 5.45(1H, dt, J = 15.4, 6.3 Hz, H-6'), 5.38 (1H, dt, J = 15.6, 6.3 Hz, H-5'), 5.26(1H, m, H-3), 2.50 (1H, dt, J = 14.3, 2.4 Hz, H-4a), 2.37 (2H, t, J = 7.5 Hz,H-2'), 2.05 (1H, dd, J = 14.3, 2.4 Hz, H-2a), 2.00 (2H, m, H-4'), 2.00 (2H,m, H-7'), 1.88 (1H, dd, J = 14.4, 4.3 Hz, H-4b), 1.72 (3H, s, H-11), 1.66 (1H,dd, J = 13.3, 3.0 Hz, H-2b), 1.42 (3H, s, H-9), 1.31 (3H, s, H-10), 1.29 (14H,m, H-8'–H-14'), 1.19 (2H, m, H-3'), 0.90 (3H, t, J = 6.9 Hz, H-15'); 13 C NMR (100 MHz, CD3OD) δ : 183.8 (C-6), 173.7 (C-1'), 173.9 (C-8), 132.8 (C-6'),130.2 (C-5'), 114.2 (C-7), 87.8 (C-5), 70.0 (C-3), 45.1 (C-2), 43.8 (C-4),36.9 (C-1), 34.7 (C-2'), 33.6 (C-7'), 33.1 (C-4'), 30.8 (C-10), 30.5 (C-8'–C-14'), 27.1 (C-11), 26.6 (C-9), 25.7 (C-3'), 14.5 (C-15')。 2. The method for preparing a monoterpene lactone compound according to claim 1, characterized in that: The mesh number of the silica gel in the silica gel column chromatography separation is 200-300 meshes.

3. The method for preparing a monoterpene lactone compound according to claim 1, characterized in that: The concentration of the ethanol is 95% v / v.

4. Use of a monoterpene lactone compound obtained by the preparation method according to any one of claims 1 to 3 in the preparation of an anti-complement drug.

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