Ganoderma heterotrichum terpenoid derivative with antioxidant and hypolipidemic activities and preparation method thereof

Abstract

The application relates to the technical field of biological processing, and discloses a ganoderma heteroterpene derivative with antioxidant and blood lipid-lowering activities and a preparation method thereof, which comprises the following steps: using methanol to dissolve Ganoderma capense ethyl acetate extract and mixing with silica gel; 10 components of crude components Fr.1-Fr.10 are obtained, and a compound one is separated; Fr.5 components are selected and a compound three is prepared; Fr.9 components are selected to carry out silica gel column chromatography and a compound two is separated; the ganoderma heteroterpene derivative with antioxidant and blood lipid-lowering activities and the preparation method thereof can reverse the trend that the MDA content in tissues is increased and the GPX activity is decreased after high-fat diet is taken due to lipid accumulation and increased lipid peroxidation, can realize lipid-lowering activity, and is easy to prepare from raw materials and suitable for popularization and use.

Description

Technical Field

[0001] This invention relates to the field of bioprocessing technology, specifically to a Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activities and its preparation method. Background Technology

[0002] Reishi mushroom is a fungus belonging to the family Ganodermataceae and the genus Ganoderma. Most reishi fruiting bodies are annuals, with a few being perennials. They are stalked, with the stalks being lateral. The cap is woody, corky, fan-shaped, grooved, kidney-shaped, semi-circular, or nearly circular. The surface is brownish-yellow or reddish-brown, blood-red to chestnut, sometimes gradually turning pale yellowish-brown to yellowish-white at the edge, with a lacquer-like sheen. The cap surface has concentric grooves, and the edge is sharp or slightly blunt, often rolled inwards. The flesh is white to pale brown, often turning pale brown near the tubes. The tubes are small, with pale white, cinnamon-white, pale brown to pale yellowish-brown pores, and nearly circular openings. The stipe is lateral, eccentric, or central, nearly cylindrical, and has a strong lacquer-like sheen. The basidiospores are oval or truncate at the apex, with a double wall; the outer wall is transparent and smooth, while the inner wall is brown or pale brown, with small spines, and a central oil droplet.

[0003] Short-term acute intake of excessive high-fat foods causes oxidative stress in organisms. High blood lipids can affect cardiovascular and cerebrovascular diseases, and in severe cases, can easily lead to coronary heart disease and pancreatitis. Abnormal blood lipids include elevated cholesterol and triglycerides, elevated low-density lipoprotein, or decreased high-density lipoprotein. In view of this, we propose a Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activities and its preparation method. Summary of the Invention

[0004] The purpose of this invention is to provide a Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activities and its preparation method, so as to solve the problems mentioned in the background art.

[0005] To achieve the above objectives, the present invention provides the following technical solution: a method for preparing Ganoderma lucidum terpene derivatives with antioxidant and lipid-lowering activities, the method comprising the following steps:

[0006] S1. Dissolve 1.1 kg of Ganoderma lucidum ethyl acetate extract with methanol and mix with 100-200 mesh silica gel. After the methanol has completely evaporated, the sample layer silica gel is obtained. The sample layer is eluted by 300-400 mesh silica gel column chromatography using petroleum ether-ethyl acetate and dichloromethane-methanol.

[0007] S2. Ten crude components, Fr.1-Fr.10, were obtained. Component Fr.4 was selected and further divided into five components. Fr.4.3 was selected, and fraction Fr.4.3.7 was obtained by gradient elution using a methanol-water system in reversed-phase column chromatography. Fractions Fr.4.3.7.6.6 were then separated using 60% methanol in normal-phase chromatography (chloroform-methanol = 80:1) and gel column chromatography (chloroform-methanol = 1:1) to obtain compound one.

[0008] S3. Select Fr.5 fraction and use a reverse-phase column in a methanol-water system to divide the fraction into 10 fractions Fr.5.1-Fr.5.10; the obtained Fr.5.4 fraction was separated using a gel permeation column and a normal-phase silica gel column, and then compound three was obtained using 50% methanol;

[0009] S4. Selecting Fr.9 fractions and separating them by silica gel column chromatography (dichloromethane-methanol = 80:1) yielded 9 fractions Fr.9.1-9;

[0010] Fr.9.6 was separated into Fr.9.6.1, Fr.9.6.2, and Fr.9.6.3 by reverse-phase column chromatography and gel column chromatography.

[0011] Fr.9.6.1.2, obtained from Fr.9.6.1, was separated by reverse column chromatography with a chloroform-methanol solution at a mass ratio of 1 and 20% methanol. Fr.9.6.3 was separated by silica gel column chromatography (chloroform-methanol = 50:1), gel column chromatography (chloroform-methanol = 1:1), and HPLC (20% acetonitrile + 1‰ trifluoroacetic acid) to obtain compound 2.

[0012] Optionally, the concentration ratio of petroleum ether to ethyl acetate in S1 is 100:0, 20:1, 4:1, or 1:1; the concentration ratio of dichloromethane to methanol is 20:1, 10:1, 5:1, or 0:100.

[0013] Optionally, in S2, the mass of Fr.4 is 141.1 g; the mass of Fr.4.3 is 42.4 g; the concentrations of methanol in the methanol-water system in S2 are, in order: 30%, 40%, 50%, 60%, 70%, 80%, 90%, and 100%; the mass of Fr.4.3.7 is 921.1 mg; the mass of Fr.4.3.7.6.6 is 12.0 mg; and the mass of compound one is 2.9 mg.

[0014] Optionally, the mass of Fr.5 in S3 is 6.0 g; the concentrations of methanol in methanol-water in S3 are, in order: 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, and 100%; the mass of Fr.5.4 in S3 is 210.3 mg; and the mass of compound three is 30.1 mg.

[0015] Optionally, in S4, the mass of Fr.9 is 75.1g; the mass of Fr.9.6 is 35.2g; the mass of Fr.9.6.1 is 3.6g; the mass of Fr.9.6.2 is 2.7g; the mass of Fr.9.6.3 is 12.0g; the mass of Fr.9.6.1.2 is 2.1g; and the mass of compound two is 4.0mg.

[0016] The present invention also proposes a Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activities, wherein the Ganoderma lucidum terpene derivative includes compound one, compound two and compound three.

[0017] Optionally, compound one is a yellow gel, and the molecular ion peak m / z [M+H] is determined by high-resolution mass spectrometry (HR-MS). + 261.1123 indicates that the molecular formula of this compound is C. 15 H 16 O4.

[0018] Optionally, compound two is a yellow gel, and the molecular ion peak m / z [M+Na] is determined by high-resolution mass spectrometry (HR-MS). + 315.0821 indicates that the molecular formula of this compound is C. 15 H 16 O6 has an unsaturation degree of 8.

[0019] Optionally, compound three is a yellow gel, and the high-resolution mass spectrometry (HR-MS) molecular ion peak m / z is [M+Na]. + 331.1160 indicates that the molecular formula of this compound is C. 16 H 20 O6 has an unsaturation degree of 7.

[0020] Compared with the prior art, the present invention provides a Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activities and its preparation method, which has the following beneficial effects:

[0021] This Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activities and its preparation method showed that after consuming a high-fat diet, due to lipid accumulation and increased lipid peroxidation, the MDA content in tissues increased and the GPX activity decreased. After intervention with compound one, this trend was reversed, which can reduce lipid activity. Moreover, the raw materials are easy to obtain and are suitable for widespread use. Attached Figure Description

[0022] Figure 1 This is a schematic diagram of the process of the present invention;

[0023] Figure 2 This is a schematic diagram of compound one of the present invention;

[0024] Figure 3 This is a schematic diagram of compound two of the present invention;

[0025] Figure 4 This is a schematic diagram of compound three of the present invention;

[0026] Figure 5 HMBC, a key component of the compound of this invention, 1 H- 1 A schematic diagram of H COSY;

[0027] Figure 6 HMBC, which is the key component of compound two in this invention, 1 H- 1 A schematic diagram of H COSY;

[0028] Figure 7 The three key components of the compound of this invention are HMBC, 1 H- 1 A schematic diagram of H COSY;

[0029] Figure 8 This is a schematic diagram showing the effect of compound one of the present invention on the GPX activity and MDA content in terms of its ability to resist lipid peroxidation;

[0030] Figure 9 This is a schematic diagram illustrating the effect of compound one of the present invention on the antioxidant capacity of SOD and CAT activities;

[0031] Figure 10 This is a schematic diagram showing the staining results of the compound of the present invention, Oil Red O.

[0032] Figure 11 This is a schematic diagram showing the lipid clearance results of the compound of the present invention. Detailed Implementation

[0033] The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0034] like Figures 1-11 As shown, the present invention provides a technical solution: a method for preparing a Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activity, the method comprising the following steps:

[0035] S1. Dissolve 1.1 kg of Ganoderma lucidum ethyl acetate extract with methanol and mix with 100-200 mesh silica gel. After the methanol has completely evaporated, the sample layer silica gel is obtained. The sample layer is eluted by 300-400 mesh silica gel column chromatography using petroleum ether-ethyl acetate and dichloromethane-methanol. The concentration ratio of petroleum ether-ethyl acetate in S1 is 100:0, 20:1, 4:1, 1:1; the concentration ratio of dichloromethane-methanol is 20:1, 10:1, 5:1, 0:100.

[0036] S2. Ten crude components, Fr.1-Fr.10, were obtained. Component Fr.4 was selected and further divided into five components. Fr.4.3 was selected, and fraction Fr.4.3.7 was obtained by gradient elution using a methanol-water system in reversed-phase column chromatography. Fractions Fr.4.3.7.6.6 were then separated using 60% methanol in normal-phase chromatography (chloroform-methanol = 80:1) and gel column chromatography (chloroform-methanol = 1:1) to obtain compound one.

[0037] The mass of Fr.4 is 141.1 g; the mass of Fr.4.3 is 42.4 g; the concentrations of methanol in the methanol-water system in S2 are 30%, 40%, 50%, 60%, 70%, 80%, 90%, and 100% respectively; the mass of Fr.4.3.7 is 921.1 mg; the mass of Fr.4.3.7.6.6 is 12.0 mg; and the mass of compound one is 2.9 mg.

[0038] S3. Selecting fraction Fr.5, using a reverse-phase column in a methanol-water system, the fraction was divided into 10 fractions Fr.5.1-Fr.5.10. The obtained Fr.5.4 was separated using gel permeation and normal-phase silica gel column chromatography, and compound 3 was obtained using 50% methanol. The mass of Fr.5 was 6.0 g. The methanol concentrations in the methanol-water mixture in S3 were 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, and 100%, respectively. The mass of Fr.5.4 in S3 was 210.3 mg, and the mass of compound 3 was 30.1 mg.

[0039] S4. Fr.9 fraction was separated into nine fractions, Fr.9.1-9, by silica gel column chromatography (dichloromethane-methanol = 80:1). Fr.9.6 was separated into Fr.9.6.1, Fr.9.6.2, and Fr.9.6.3 by reverse-phase column chromatography and gel column chromatography. Fr.9.6.1.2 was separated from Fr.9.6.1 by reverse-phase column chromatography with chloroform-methanol solution (1:1 by mass) and 20% methanol. Fr.9.6.3 was separated into compound two by silica gel column chromatography (chloroform-methanol = 50:1), gel column chromatography (chloroform-methanol = 1:1), and HPLC (20% acetonitrile + 1‰ trifluoroacetic acid).

[0040] The mass of Fr.9 is 75.1 g; the mass of Fr.9.6 is 35.2 g; the mass of Fr.9.6.1 is 3.6 g; the mass of Fr.9.6.2 is 2.7 g; the mass of Fr.9.6.3 is 12.0 g; the mass of Fr.9.6.1.2 is 2.1 g; and the mass of compound II is 4.0 mg.

[0041] This embodiment also proposes a Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activities. The Ganoderma lucidum terpene derivative includes compound 1, compound 2 and compound 3. Compound 1 and compound 2 are benzopyrene monoterpenes, and compound 3 is a benzopyrene monoterpenes.

[0042] like Figure 2 As shown, the m / z of the molecular ion peak [M+H] in high-resolution mass spectrometry (HR-MS) is... + 261.1123 indicates that the molecular formula of this compound is C. 15 H 16 O4 has an unsaturation degree of 8. 1 1H NMR showed that compound 1 had a typical aromatic proton signal. Based on the chemical shift and coupling constant, the substitution on the benzene ring was determined to be an ABX spin system, i.e., the presence of a 1,2,4-trisubstituted benzene ring [δ]. H 7.24, d, J = 2.9 Hz (H-3); 6.96, dd, J = 8.9, 2.9 Hz (H-5); 6.77, d, J = 8.9 Hz (H-6)], in addition to two olefin hydrogen signals [δ H [6.74,s(H-2′),6.16,s(H-8′)], two methylene hydrogen signals (δ H 3.25, 2.87, 1.97, 1.73), a hydrogen signal of 4.20 (1H, t, J = 6.1 Hz, H-6′) and a singlet methyl signal of 2.0 (3H, s, H-9′), based on chemical shifts, indicate that the methyl group is directly attached to the double bond. 13C10 NMR and HSQC data show the presence of 15 carbon atoms, which can be attributed to one methyl group C-9′ (δ). C 20.9), 2 methylene [δ C [25.5(C-4′), 32.4(C-5′)], 5 methines, 4 of which are sp. 2 Hybridization [δ] C 115.2(C-3), 125.0(C-5), 119.6(C-6), 118.5(C-2′)] Another is a compound oxygen sp. 3 Hybridized methine [69.2(C-6′)], 6 quaternary carbons, including 5 alkene carbons [δ] C [157.2(C-1),122.2(C-2),150.3(C-3),197.1(C-1′),157.1(C-2′),152.5(C-7′)], and a conjugated ketone carbonyl group [δ C 197.1(C-1′)],. By integrating 1D NMR data, it is preliminarily inferred that this compound is a benzopyrene. Literature review and comparison revealed that the 1D NMR data of 1 is highly similar to that of compound Baoslingzhine D (Wang et al. 2022), the difference being that the ethoxy substitution at C-6′ is replaced by a hydroxyl substitution. Simultaneously, the HMBC spectrum shows: H-3, H-2′ and C-1′; H-2′ and C-3′, C-4′, C-7′; H-9′ (δ H 2.0,s) is related to C-6′, C-7′, and C-8′. And 1 H- 1 The H-COSY spectrum indicates that H-4′(δ H 3.25,m; 2.87,m), H-5′(δ H 1.97,m; 1.73,m), H-6′(δ H A correlation of 4.20, t, J = 6.1 Hz confirmed the presence of the hydroxyl group at the C-6′ position. Observation of the ROSEY spectrum showed a correlation between H-2′ and H-4′a. Based on CD and optical rotation, the compound was determined to be a pair of enantiomers and named (±)-Baoslingzhine F.

[0043] like Figure 3 As shown, the m / z of the molecular ion peak [M+Na] in high-resolution mass spectrometry (HR-MS) is... + 315.0821 indicates that the molecular formula of this compound is C. 15 H 16 O6 has an unsaturation degree of 8. 11H NMR showed that compound 2 had a typical aromatic proton signal. Based on the chemical shift and coupling constant, the substitution on the benzene ring was determined to be an ABX spin system, revealing the presence of a 1,2,4-trisubstituted benzene ring [δ]. H 7.23, d, J = 3.0 Hz (H-3); 7.00, dd, J = 8.9, 3.0 Hz (H-5); 6.78, d, J = 9.0 Hz (H-6)], 1 olefinic hydrogen signal H-7′ (δ H The chemical shift indicates the presence of three methylene hydrogen signals (δH 3.94, 3.19, 2.92, 2.53, 2.37, 1.86) and one hydroxymethylene hydrogen signal (δH 4.20, 1H, t, J = 1.9 Hz, H-9′). Based on the chemical shift, a hydroxymethyl signal may be present. 13 C10 NMR and HSQC data show the presence of 15 carbon atoms, which can be divided into 4 methylene groups [δ]. C 46.9(C-2′), 36.7(C-4′), 31.5(C-5′), 59.9(C-9′)], 4 methines, all sp. 2 Hybridization [δ] C 115.4(C-3), 125.8(C-5), 119.7(C-6), 131.8(C-7′)], 7 quaternary carbons, including 3 alkene carbons [δ C 156.4(C-1), 120.6(C-2), 150.6(C-4), 145.5(C-6′)], one ketone carbonyl carbon δ C 202.5(C-1′), one carboxyl carbon δ C 178.7 (C-8′). The difference is that the H MBC shows H-3, H-2′ (δ H 3.94,d,J=18.4Hz; 3.19,d,J=18.4Hz) are related to C-1′, H-2′,H-4′ (δ H Ha (2.92 m; Hb (1.86 m) is associated with C-8′, H-7′ is associated with C-4, C-5′, C-6′, and C-8′, and H-9′ is associated with C-6′, H-7′, and C-7′. And... 1 H- 1 The H-COSY spectrum indicates that H-2′, H-4′ and H-5′ (δ) H (Ha: 2.53, m; Hb: 2.37, m) related. This compound's... 1 H NMR and 13The C10 NMR data are similar to those of compound (±)-Applanatumol N (Luo et al. 2016) in the literature, while 2D NMR data confirm that the B ring of the heteroterpene is cyclopentene, not cyclohexene, as described in (±)-Applanatumol N. NOESY spectra show H-3 and H-2′ (δ) H The correlations are as follows: H-7′ is related to H-5′ and H-9′, and H-4′ is related to H-5′. Based on CD and optical rotation, compound 2 is determined to be a pair of enantiomers and named (±)-ApplanatumolN2.

[0044] like Figure 4 As shown, the m / z of the molecular ion peak [M+Na] in high-resolution mass spectrometry (HR-MS) is... + 331.1160 indicates that the molecular formula of this compound is C. 16 H 20 O6 has an unsaturation degree of 7. 1 1H NMR showed that compound 3 had a typical aromatic proton signal. Based on the chemical shift and coupling constant, the substitution on the benzene ring was determined to be an ABX spin system, revealing the presence of a 1,2,4-trisubstituted benzene ring [δ]. H 7.80, d, J = 3.0 Hz (H-3); 7.37, dd, J = 8.8, 2.9 Hz (H-5); 7.09, d, J = 8.9 Hz (H-6)], the hydrogen signal H-6′ (δ) of one olefin. H 5.42 (t, J = 8.1 Hz), a hydroxymethyl hydrogen signal at 4.20 (1H, s, H-8′). Based on the chemical shift, there may be one hydroxymethyl signal. 13 C10 NMR and HSQC data show the presence of 16 carbon atoms, which can be separated into one methyl C-10′ (δ) group. C 22.2), 4 methylene [δ C [41.4(C-2′), 33.4(C-4′), 26.1(C-5′), 61.2(C-8′)], 5 methines, of which 4 are sp. 2 Hybridization [δ] C 116.3(C-3),126.1(C-5),119.7(C-6),126.3(C-6′)], 1 sp 3 Hybrid δ C 41.0 (C-3′), 6 quaternary carbons [δ C 156.1(C-1), 120.9(C-2), 151.3(C-4), 205.7(C-1′), 137.9(C-7′), 178.1(C-9′)], except for the four olefinic carbon signals [δ C156.1(C-1),120.9(C-2),151.3(C-4),137.9(C-7′)], 1 [δ] with a ketone carbonyl group attached. C 205.7C-1′] and a hydroxyl carbon signal [δ C 178.1(C-9′)]. HMBC shows H-2′(δ) H 3.87,m; 3.28,m),H-3′(δ H 3.45,m),H-4′(δ H 2.08,m; 1.88,m) are associated with the C-9′ carboxyl group; H-5′ (δ H 2.44, q, J = 7.7 Hz) is correlated with C-6′, C-7′, and H-10′ (δ H 1.81,s) is associated with C-6′, C-7′, and C-8′. 1 H- 1 The H-COSY spectrum showed correlations between H-2′ and H-3′, H-4′, and H-5′, while the ROSEY spectrum showed correlations between H-6′ and H-10′, confirming that the side chain of this compound is a chain-like monoterpene. 1 HNMR and 13 C10 NMR and 2D NMR showed that the compound was highly similar to compound (±)-applanatumols S (Luo et al. 2016) in the literature, and compound (±)-applanatumols S had already been isolated from Ganoderma lucidum in this study, numbered 4. Compound 3 was obtained from the same component by HPLC separation. Based on the spectral analysis, it was deduced that the data of 3 and 4 were only similar at C-6′ (δ). c 126.3), C-8′(δ c 61.2), C-10′(δ c The data in 22.2) differ; C-8′ and C-9′ are on the same side, and 3 is a cis structure, which is confirmed by the ROSEY correlation between H-6′ and H-10′. 4 and 3 are cis-trans isomers. Based on CD and optical rotation, compound 3 is determined to be an enantiomer and named (±)-Applanatumol S2.

[0045] In this embodiment, after consuming a high-fat diet, lipid accumulation and increased lipid peroxidation were observed, resulting in increased MDA content and decreased GPX activity in the tissue. This trend was reversed after intervention with compound one, which can reduce lipid activity. Moreover, the raw materials are easy to obtain and suitable for widespread use.

[0046] like Figure 8As shown, after consuming a high-fat diet, due to lipid accumulation and increased lipid peroxidation, we can observe an increase in MDA content and a decrease in GPX activity in tissues. However, this trend was reversed after intervention with compound 1.

[0047] like Figure 9 As shown, short-term acute intake of excessive high-fat food induces oxidative stress in organisms, and we observed a significant decrease in the scavenging capacity of SOD and ·OH in tissues. However, compound 1 alleviated these adverse lesions induced by the high-fat diet, demonstrating that compound 1 can significantly reduce the level of oxidative stress induced by a high-fat diet in zebrafish. Its concentration and trend of action are similar to the decreasing trend of TG. The effect is most significant at a concentration of 5 μM.

[0048] like Figures 10-11 As shown, Oil Red O staining was used to observe lipid accumulation in zebrafish to initially screen the lipid-lowering activity of compounds at a concentration of 20 μM. The results showed that compound 1 had the best lipid-lowering activity. In the control group, only a small amount of lipid was stained in the vitelline membrane, which is normal. In contrast, in the model group, significant lipid accumulation was observed in the blood vessels of the abdomen, heart area, near the spine, and especially the liver area of ​​the zebrafish. Compared with the model group, the drug-treated group significantly reversed the trend of lipid accumulation. The staining results indicate that compound 1 effectively improved lipid accumulation in zebrafish and reduced the progression of hyperlipidemia to some extent. From the lipid clearance rate results, compound 1 had a better lipid clearance effect than atorvastatin calcium.

[0049] The present invention has been described in detail above. However, modifications or improvements can be made to it, which will be obvious to those skilled in the art. Therefore, any modifications or improvements that do not depart from the spirit of the present invention are within the scope of protection of the present invention.

Claims

1. A method for preparing a Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activities, characterized in that: The method includes the following steps: S1. Dissolve 1.1 kg of Ganoderma lucidum ethyl acetate extract in methanol and mix with 100-200 mesh silica gel. After the methanol has completely evaporated, the sample layer silica gel is obtained. The sample layer is eluted by 300-400 mesh silica gel column chromatography using petroleum ether-ethyl acetate and dichloromethane-methanol. S2. Ten crude components, Fr.1-Fr.10, were obtained. Component Fr.4 was selected and further divided into five components. Fr.4.3 was selected, and fraction Fr.4.3.7 was obtained by gradient elution using a methanol-water system in reversed-phase column chromatography. Components Fr.4.3.7.6.6 were then separated using 60% methanol in normal-phase chromatography and gel column chromatography to obtain compound one. The normal-phase chromatography used an 80:1 chloroform-methanol mixture, and the gel column chromatography used a 1:1 chloroform-methanol mixture. The concentration ratio of petroleum ether to ethyl acetate in S1 is 100:0, 20:1, 4:1, 1:1; the concentration ratio of dichloromethane to methanol is 20:1, 10:1, 5:1, 0:

100. The methanol concentrations in the methanol-water system in S2 are, in order: 30%, 40%, 50%, 60%, 70%, 80%, 90%, and 100%. The compound is one of .

2. The method for preparing the Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activity according to claim 1, characterized in that: In S2, the mass of Fr.4 is 141.1 g; the mass of Fr.4.3 is 42.4 g; the mass of Fr.4.3.7 is 921.1 mg; the mass of Fr.4.3.7.6.6 is 12.0 mg; and the mass of compound one is 2.9 mg.

3. A Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activities, characterized in that: The Ganoderma lucidum terpene derivative is .

4. The use of the Ganoderma lucidum terpene derivatives according to claim 3 in the preparation of antioxidant lipid-lowering drugs.

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