Ganoderma lucidum meroterpenoid derivative with antioxidant and blood fat reducing activity and preparation method thereof

Abstract

The invention relates to the technical field of biological processing, and discloses a ganoderma lucidum meroterpenoid derivative with antioxidant and blood fat reducing activity and a preparation method thereof, and the preparation method comprises the following steps: dissolving ganoderma applanatum ethyl acetate extract with methanol, and mixing with eye silica gel; 10 crude components Fr.1-Fr.10 are obtained, and a first compound is obtained through separation; selecting an Fr.5 component and preparing a compound III; according to the ganoderma lucidum meroterpenoid derivative with the antioxidant and blood fat reducing activity and the preparation method thereof, after a user takes a high-fat diet, due to lipid accumulation and lipid peroxidation degree improvement, MDA content increase and GPX activity reduction in tissues are observed, the trend is turned after intervention of the compound I, and the ganoderma lucidum meroterpenoid derivative with the antioxidant and blood fat reducing activity is obtained. And the raw materials are easy to prepare, so that the preparation method is suitable for popularization and application.

Description

Technical Field

[0001] The invention relates to the technical field of bioprocessing, in particular to a ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activity and a preparation method thereof. Background Art

[0002] Ganoderma is a fungus of the Ganoderma family and the genus Ganoderma. Most of the fruiting bodies of Ganoderma are annual, and a few are perennial. They have stalks, and the stalks are lateral. The cap is woody, corky, fan-shaped, with grooves, kidney-shaped, semicircular or nearly circular, with a brownish yellow or reddish brown surface, blood red to chestnut, and sometimes the edges gradually turn into light yellow brown to yellowish white, with a lacquer-like luster. There are concentric grooves on the cap surface, with sharp or slightly blunt edges, often involute. The flesh is white to light brown, often light brown near the tube, the tube is small, the tube pore surface is light white, white cinnamon, light brown to light yellow brown, the tube mouth is nearly circular, the stipe is lateral, eccentric or mesogenous, nearly cylindrical, and has a strong lacquer-like luster. The basidiospores are ovate or truncated at the top, double-walled, the outer wall is transparent and smooth, the inner wall is brown or light brown, with small thorns, and an oil drop in the center.

[0003] After short-term acute intake of excessive high-fat food, oxidative stress is caused in the living body. Hyperlipidemia can affect cardiovascular and cerebrovascular diseases, and in severe cases it can easily cause coronary heart disease and pancreatitis. Dyslipidemia includes increased cholesterol and triglycerides, increased low-density lipoprotein, or decreased high-density lipoprotein. In view of this, we proposed a Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activity and a preparation method thereof. Summary of the invention

[0004] The purpose of the present invention is to provide a Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activity and a preparation method thereof, so as to solve the problems raised in the above background technology.

[0005] To achieve the above object, the present invention provides the following technical solution: a method for preparing a Ganoderma lucidum terpene derivative having antioxidant and lipid-lowering activity, the method comprising 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 is completely evaporated, obtain a sample layer of silica gel. Use 300-400 mesh silica gel column chromatography to elute the sample layer with petroleum ether-ethyl acetate and dichloromethane-methanol. S2. Obtain 10 crude components Fr.1-Fr.10; select component Fr.4 and further divide it into 5 components, select Fr.4.3, use reverse phase column chromatography methanol-water system for gradient elution to obtain component Fr.4.3.7, and separate the components by normal phase chromatography chloroform methanol (80:1) and gel column chromatography (chloroform-methanol = 1:1) using 60% methanol to obtain compound 1; S3, select the Fr.5 component, use a reverse phase chromatographic column of a methanol-water system to divide the component into 10 components Fr.5.1-Fr.5.10; after the obtained Fr.5.4 is separated using a gel chromatographic column and a normal phase silica gel chromatographic column, 50% methanol is used to obtain compound three; S4, selecting Fr.9 component and performing silica gel column chromatography (dichloromethane-methanol=80:1) to separate and obtain 9 components Fr.9.1-9; Fr.9.6 was separated by reverse phase column chromatography and gel column chromatography to obtain Fr.9.6.1, Fr.9.6.2 and Fr.9.6.3; The component Fr.9.6.1.2 was separated from Fr.9.6.1 using a chloroform-methanol solution with a mass ratio of 1 and 20% methanol reverse column chromatography. Fr.9.6.3 was separated using (chloroform-methanol = 50:1) silica gel column chromatography, (chloroform-methanol = 1:1) gel column chromatography and HPLC (20% acetonitrile + 1‰ trifluoroacetic acid) to obtain compound 2.

[0006] Optionally, 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;.

[0007] Optionally, the mass of Fr.4 in S2 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.

[0008] Optionally, the mass of Fr.5 in S3 is 6.0 g; the concentrations of methanol in methanol-water in S3 are 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, and 100% respectively; the mass of Fr.5.4 in S3 is 210.3 mg; and the mass of compound three is 30.1 mg.

[0009] Optionally, the mass of Fr.9 in S4 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 2 is 4.0 mg.

[0010] The present invention also provides a Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activity. The Ganoderma lucidum terpene derivative comprises compound one, compound two and compound three.

[0011] Optionally, the compound 1 is a yellow colloid, and the high resolution mass spectrometry HR-MS molecular ion peak m / z [M + H] + 261.1123, indicating that the molecular formula of the compound is C 15 H 16 O4.

[0012] Optionally, the compound 2 is a yellow colloid, and the high resolution mass spectrometry HR-MS molecular ion peak m / z [M+Na] + 315.0821, indicating that the molecular formula of the compound is C 15 H 16 O6, unsaturation is 8.

[0013] Optionally, the compound three is a yellow colloid, and the high resolution mass spectrometry HR-MS molecular ion peak m / z [M+Na] + 331.1160, indicating that the molecular formula of the compound is C 16 H 20 O6, unsaturation is 7.

[0014] Compared with the prior art, the present invention provides a Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activity and a preparation method thereof, which has the following beneficial effects: The Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activity and the preparation method thereof, after taking a high-fat diet, due to lipid accumulation, the degree of lipid peroxidation increases, and it is observed that the MDA content in the tissue increases and the GPX activity decreases. After the intervention of compound 1, this trend is reversed, and the lipid activity can be reduced. The raw materials are easy to prepare and are suitable for popularization and use. BRIEF DESCRIPTION OF THE DRAWINGS

[0015] Figure 1 It is a schematic diagram of the process of the present invention; Figure 2 is a schematic diagram of a compound of the present invention; Figure 3 is a schematic diagram of compound 2 of the present invention; Figure 4 is a schematic diagram of the third compound of the present invention; Figure 5 HMBC is a key compound of the present invention, 1 H- 1 Schematic diagram of H COSY; Figure 6 HMBC, which is a key component of the compound of the present invention, 1 H- 1Schematic diagram of H COSY; Figure 7 HMBC, 1 H- 1 Schematic diagram of H COSY; Figure 8 Schematic diagram of the effect of compound 1 of the present invention on anti-lipid peroxidation ability, GPX activity and MDA content; Fig. 9 Schematic diagram of the effect of compound 1 of the present invention on the antioxidant capacity of SOD activity and CAT activity; Fig.10 This is a schematic diagram of the staining results of Oil Red O, a compound of the present invention; Fig.11 It is a schematic diagram of the lipid clearance results of the compound of the present invention. DETAILED DESCRIPTION

[0016] The following will be combined with the drawings in the embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0017] like Figure 1-Figure 11 As shown, the present invention provides a technical solution: a method for preparing a Ganoderma lucidum terpene derivative having antioxidant and lipid-lowering activity, the method comprising the following steps: S1. Dissolve 1.1 kg of Ganoderma lucidum ethyl acetate extract in methanol and mix it with 100-200 mesh silica gel. After the methanol is completely evaporated, obtain the sample layer silica gel. Pass through 300-400 mesh silica gel column chromatography and elute the sample layer with petroleum ether-ethyl acetate and dichloromethane-methanol. The concentration ratios of petroleum ether-ethyl acetate in S1 are: 100:0, 20:1, 4:1, 1:1; the concentration ratios of dichloromethane-methanol are 20:1, 10:1, 5:1, 0:100.

[0018] S2. Obtain 10 crude components Fr.1-Fr.10; select component Fr.4 and further divide it into 5 components, select Fr.4.3, use reverse phase column chromatography methanol-water system for gradient elution to obtain component Fr.4.3.7, and separate the components by normal phase chromatography chloroform methanol (80:1) and gel column chromatography (chloroform-methanol = 1:1) using 60% methanol to obtain compound 1; 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; the mass of compound one is 2.9 mg.

[0019] S3, select Fr.5 component, use a reverse chromatographic column of methanol-water system to divide the component into 10 components Fr.5.1-Fr.5.10; the obtained Fr.5.4 is separated by using a gel chromatography column and a normal phase silica gel chromatography column, and then compound three is obtained using 50% methanol; the mass of Fr.5 is 6.0 g; the concentrations of methanol in methanol-water in S3 are: 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 100%; the mass of Fr.5.4 in S3 is 210.3 mg; the mass of compound three is 30.1 mg.

[0020] S4. Select component Fr.9 and perform silica gel column chromatography (dichloromethane-methanol = 80:1) separation to obtain 9 components Fr.9.1-9; perform reverse column chromatography and gel column chromatography separation on Fr.9.6 to obtain Fr.9.6.1, Fr.9.6.2 and Fr.9.6.3; use a chloroform-methanol solution with a mass ratio of 1 and 20% methanol reverse column chromatography to separate Fr.9.6.1 to obtain component Fr.9.6.1.2; use (chloroform-methanol = 50:1) silica gel column chromatography, (chloroform-methanol = 1:1) gel column chromatography and HPLC (20% acetonitrile + 1‰ trifluoroacetic acid) to separate Fr.9.6.3 to obtain compound 2.

[0021] 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; the mass of compound 2 is 4.0mg.

[0022] This embodiment also proposes a Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activity. The flat-capped Ganoderma lucidum terpene derivative includes compound one, compound two and compound three. Compound one and compound two are benzyl monoterpenes, and compound three is benzyl monoterpene.

[0023] like Figure 2 As shown, the high-resolution mass spectrometry HR-MS molecular ion peak m / z [M + H] + 261.1123, indicating that the molecular formula of the compound is C 15H 16 O4, unsaturation is 8. 1 H NMR showed that compound 1 had typical aromatic proton signals. Based on the chemical shift and coupling constant, it was judged that the substitution on the benzene ring was an ABX spin system, that is, the existence 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 connected oxygen methylene hydrogen signal 4.20 (1H, t, J = 6.1 Hz, H-6′) and a singlet methyl group 2.0 (3H, s, H-9′). According to the chemical shift, the methyl group was directly connected to the double bond. 13 C NMR and HSQC data showed the presence of 15 carbon atoms, which can be assigned to 1 methyl C-9′ (δ C 20.9), 2 methylene groups [δ C 25.5 (C-4′), 32.4 (C-5′)], 5 methine groups, 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 oxygen-linked sp 3 Hybridized methine [69.2 (C-6′)], 6 quaternary carbons, including 5 olefinic 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 keto carbonyl [δ C 197.1 (C-1′)]. By integrating the data information of 1D NMR, it is preliminarily speculated that the compound is a benzene heteromonoterpenoid compound. By consulting the literature and comparing it, it was found that the 1D NMR data of 1 was highly similar to the compound Baoslingzhine D (Wang et al. 2022) in the literature, the difference being that the ethoxy substitution at the C-6′ position was replaced by a hydroxyl substitution. At the same time, the HMBC spectrum showed that: H-3, H-2′ and C-1′; H-2′ and C-3′, C-4′, C-7′; H-9′ (δ H2.0, s) are associated with C-6′, C-7′, C-8′. And 1 H- 1 The H-COSY spectrum shows 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 4.20, t, J = 6.1 Hz)相关，证实了C-6′位羟基的存在。观察ROSEY谱图，H-2′与H-4′a相关。根据CD以及旋光度确定该化合物为一对对映异构体，并命名为( ±)-Baoslingzhine F。

[0024] like Figure 3 As shown, the high resolution mass spectrometry HR-MS molecular ion peak m / z [M+Na] + 315.0821, indicating that the molecular formula of the compound is C 15 H 16 O6, unsaturation is 8. 1 H NMR showed that compound 2 had typical aromatic proton signals. The substitution on the benzene ring was judged to be an ABX spin system based on the chemical shift and coupling constant, revealing the existence 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 5.92, t, J =2.0 Hz), three methylene hydrogen signals (δH3.94, 3.19, 2.92, 2.53, 2.37, 1.86), and one oxymethylene hydrogen signal 4.20 (1H, t, J =1.9 Hz, H-9′). Based on the chemical shift, it is possible that there is one hydroxymethyl signal. 13 C NMR and HSQC data showed the presence of 15 carbon atoms, which can be divided into four methylene groups [δ C 46.9 (C-2′), 36.7 (C-4′), 31.5 (C-5′), 59.9 (C-9′)], 4 methine groups, 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 olefinic carbons [δ C 156.4 (C-1), 120.6 (C-2), 150.6 (C-4), 145.5 (C-6′)], a keto carbonyl carbon δ C 202.5 (C-1′), a carboxyl carbon δ C178.7 (C-8′). The difference is that H MBC shows that H-3, H-2′ (δ H 3.94, d, J = 18.4 Hz; 3.19, d, J = 18.4 Hz) are related to C-1′, H-2′, H-4′ (δ H Ha:2.92, m; Hb:1.86, m) is related to C-8′, H-7′ is related to C-4, C-5′, C-6′, C-8′, H-9′ is related to C-6′, H-7′; C-7′. 1 H- 1 The H-COSY spectrum shows that: H-2′, H-4′ and H-5′ (δ H Ha: 2.53, m; Hb: 2.37, m). 1 H NMR and 13 The C NMR data are similar to those of the compound (±)-Applanatumol N (Luo et al. 2016) in the literature, while the 2D NMR data confirm that the B ring of the heteroterpenoid is different from the cyclohexene in (±)-Applanatumol N but is cyclopentene. The NOESY spectrum shows that H-3 and H-2′ (δ H ), H-7′ is related to H-5′ and H-9′, and H-4′ is related to H-5′. According to CD and optical rotation, the compound 2 is determined to be a pair of enantiomers and named (±)-Applanatumol N2.

[0025] like Figure 4 As shown, the high resolution mass spectrometry HR-MS molecular ion peak m / z [M+Na] + 331.1160, indicating that the molecular formula of the compound is C 16 H 20 O6, unsaturation is 7. 1 H NMR showed that compound 3 had typical aromatic proton signals. The substitution on the benzene ring was judged to be an ABX spin system based on the chemical shift and coupling constant, revealing the existence 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)], one hydrogen signal of olefin H-6′ (δ H 5.42, t, J = 8.1 Hz), one oxymethylene hydrogen signal 4.20 (1H, s, H-8′). Based on the chemical shift, there may be one hydroxymethyl signal. 13C NMR and HSQC data showed the presence of 16 carbon atoms, which can be divided into 1 methyl C-10′ (δ C 22.2), 4 methylene groups [δ C 41.4 (C-2′), 33.4 (C-4′), 26.1 (C-5′), 61.2 (C-8′)], 5 methines, 4 of which 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 C 156.1 (C-1), 120.9 (C-2), 151.3 (C-4), 137.9 (C-7′)], one with a keto carbonyl group attached [δ C 205.7 C-1′] and a hydroxyl carbon signal [δ C 178.1 (C-9′)]. HMBC showed that 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) is related to the C-9′ carboxyl group; H-5′ (δ H 2.44, q, J = 7.7 Hz) is related to C-6′, C-7′, H-10′ (δ H 1.81, s) are associated with C-6′, C-7′, and C-8′. 1 H- 1 The H-COSY spectrum showed that H-2′ was correlated with H-3′, H-4′, and H-5′, and ROSEY showed signals related to H-6′ and H-10′, confirming that the side chain of the compound was a chain monoterpene. 1 H NMR and 13C NMR and 2D NMR showed that the compound was highly similar to the compound (±)-applanatumols S in the literature (Luo et al. 2016), and the compound (±)-applanatumols S in the literature has been isolated from Ganoderma lucidum in this study and is numbered 4. Compound 3 was obtained by HPLC separation of the same component. Through spectrum analysis, it is inferred that the data of 3 and 4 are only at C-6′(δ c 126.3), C-8′ (δ c 61.2), C-10′ (δ c 22.2) data are different, C-8' and C-9' are on the same side, 3 is a cis structure, and its cis structure is proved by the ROSEY correlation of H-6' and H-10'. 4 and 3 are cis-trans isomers. According to CD and optical rotation, the compound 3 is determined to be a pair of enantiomers and named (±)-Applanatumol S2.

[0026] In this embodiment, after consuming a high-fat diet, due to lipid accumulation, the degree of lipid peroxidation increased, and it was observed that the MDA content in the tissue increased and the GPX activity decreased. After the intervention of compound 1, this trend was reversed, and the lipid activity was reduced. The raw materials are easy to prepare and are suitable for promotion and use.

[0027] like Figure 8 As shown in the results, after consuming a high-fat diet, lipid peroxidation increased due to lipid accumulation, and we could observe an increase in MDA content and a decrease in GPX activity in tissues, but this trend was reversed after intervention with compound 1.

[0028] like Fig. 9 As shown in the results, after short-term acute intake of excessive high-fat food, oxidative stress was induced in the organism. We observed that the SOD and •OH scavenging capacity in the tissues was significantly reduced. However, compound 1 alleviated these adverse lesions induced by the high-fat diet, proving that compound 1 can significantly reduce the oxidative stress level induced by the high-fat diet in zebrafish. Its concentration and action trend are the same as the reduction trend of TG. The effect is most significant at a concentration of 5μM.

[0029] like Figure 10-11As shown, the lipid accumulation in zebrafish was observed using Oil Red O staining to preliminarily screen the lipid-lowering activity of the compounds at a concentration of 20 μM. The results showed that compound 1 had the best lipid-lowering activity. In the blank group, only a small amount of lipid was observed to be stained in the yolk membrane of zebrafish, which is a normal phenomenon. In the model group, lipid accumulation was significantly observed in the blood vessels of the abdomen, heart area, spine, and especially liver area of ​​zebrafish. Compared with the model group, the drug-treated group significantly reversed the trend of lipid accumulation. The staining results show that compound 1 has greatly improved the accumulation of lipids in zebrafish and reduced the progression of hyperlipidemia to a certain extent. Judging from the results of lipid clearance rate, the lipid clearance effect of compound 1 is better than that of atorvastatin calcium.

[0030] The above generally describes the present invention in detail, but it is obvious to a person skilled in the art that some modifications or improvements can be made to the present invention. Therefore, 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 having antioxidant and lipid-lowering activity, characterized in that: The method comprises 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 is completely evaporated, obtain a sample layer of silica gel. Use 300-400 mesh silica gel column chromatography to elute the sample layer with petroleum ether-ethyl acetate and dichloromethane-methanol. S2. Obtain 10 crude components Fr.1-Fr.10; select component Fr.4 and further divide it into 5 components, select Fr.4.3, use reverse phase column chromatography methanol-water system for gradient elution to obtain component Fr.4.3.7, and separate the components by normal phase chromatography chloroform methanol (80:1) and gel column chromatography (chloroform-methanol = 1:1) using 60% methanol to obtain compound 1; S3, select the Fr.5 component, use a reverse phase chromatographic column of a methanol-water system to divide the component into 10 components Fr.5.1-Fr.5.10; after the obtained Fr.5.4 is separated using a gel chromatographic column and a normal phase silica gel chromatographic column, 50% methanol is used to obtain compound three; S4, selecting the Fr.9 component and performing silica gel column chromatography (dichloromethane-methanol = 80:1) to separate and obtain 9 components Fr.9.1-9; Fr.9.6 was separated by reverse phase column chromatography and gel column chromatography to obtain Fr.9.6.1, Fr.9.6.2 and Fr.9.6.3; The component Fr.9.6.1.2 was separated from Fr.9.6.1 using a chloroform-methanol solution with a mass ratio of 1 and 20% methanol reverse column chromatography. Fr.9.6.3 was separated using (chloroform-methanol = 50:1) silica gel column chromatography, (chloroform-methanol = 1:1) gel column chromatography and HPLC (20% acetonitrile + 1‰ trifluoroacetic acid) to obtain compound 2.

2. The method for preparing the Ganoderma lucidum terpene derivatives having antioxidant and lipid-lowering activities according to claim 1, characterized in that: The concentration ratios of petroleum ether to ethyl acetate in S1 are: 100:0, 20:1, 4:1, 1:1; the concentration ratios of dichloromethane to methanol are: 20:1, 10:1, 5:1, 0:100;.

3. The method for preparing the Ganoderma lucidum terpene derivatives having antioxidant and lipid-lowering activities according to claim 1, characterized in that: The mass of Fr.4 in S2 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.

4. The method for preparing the Ganoderma lucidum terpene derivatives having antioxidant and lipid-lowering activities according to claim 1, characterized in that: The mass of Fr.5 in S3 is 6.0 g; the concentrations of methanol in methanol-water in S3 are 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90% and 100% respectively; the mass of Fr.5.4 in S3 is 210.3 mg; and the mass of compound three is 30.1 mg.

5. The method for preparing the Ganoderma lucidum terpene derivatives having antioxidant and lipid-lowering activities according to claim 1, characterized in that: The mass of Fr.9 in S4 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 2 is 4.0 mg.

6. A Ganoderma lucidum terpene derivative having antioxidant and lipid-lowering activity, characterized in that: The Ganoderma lucidum terpene derivatives include compound one, compound two and compound three.

7. The Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activity according to claim 6, characterized in that: The compound 1 is yellow colloid, and the high-resolution mass spectrometry HR-MS molecular ion peak m / z [M + H] + 261.1123, indicating that the molecular formula of the compound is C 15 H 16 O4.

8. The Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activity according to claim 6, characterized in that: The compound 2 is yellow colloid, and the high-resolution mass spectrometry HR-MS molecular ion peak m / z [M+Na] + 315.0821, indicating that the molecular formula of the compound is C 15 H 16 O6, unsaturation is 8.

9. The Ganoderma lucidum terpene derivative with antioxidant and lipid-lowering activity according to claim 6, characterized in that: The compound 3 is yellow colloid, and the high-resolution mass spectrometry HR-MS molecular ion peak m / z [M+Na] + 331.1160, indicating that the molecular formula of the compound is C 16 H 20 O6, unsaturation is 7.

Images