Monoterpene compound obtained based on separation of ormosia henryi as well as preparation method and application of monoterpene compound

Abstract

The invention relates to the technical field of natural product extraction, in particular to a monoterpene compound obtained based on separation of ormosia henryi and a preparation method and application of the monoterpene compound. According to the monoterpene compound, a (E, E)-2, 4-diene-3, 7-dimethyl octane structure is used as a parent nucleus, and specifically, the monoterpene compound is (6R, 2E, 4E)-3, 7-dimethyl octane-1-ethoxy-2, 4-diene-6, 7-diol, (6S, 2E, 4E)-3, 7-dimethyl octane-2, 4-diene-6-ethoxy-1, 7-diol or (6R, 2E, 4E)-3, 7-dimethyl octane-2, 4-diene-1, 6, 7-triol. The compound is extracted and separated from ormosia henryi, has an inhibition effect on influenza A / WSN / 33 (H1N1) virus, and can be used for preparing antiviral drugs.

Description

Technical Field

[0001] This invention relates to the field of natural product extraction technology, specifically to a monoterpene compound obtained from Dalbergia odorifera, its preparation method, and its application. Background Technology

[0002] Rosewood ( Ormosiahenryi Hemsl. & E. H. Wilson are members of the genus *Vigna* in the family Fabaceae. Ormosia The *Dalbergia odorifera* (Jacks) is a rare medicinal tree, a Class II protected plant in my country, widely distributed from southeast to southwest my country. It possesses value in ecological conservation, timber utilization, and traditional medicinal uses. The roots, stems, and leaves of the *Dalbergia odorifera* have the effects of promoting blood circulation, removing blood stasis, dispelling wind, and reducing swelling. It is often used to treat injuries from falls and blows, rheumatoid arthritis, and other ailments. It also has analgesic, anti-inflammatory, antibacterial, insecticidal, and tonic effects.

[0003] However, to date, research on the chemical components of Dalbergia odorifera has mainly focused on alkaloids, flavonoids, and volatile oils. These compounds have been reported to have various pharmacological activities such as antioxidant, antidepressant, and anti-inflammatory effects. Other types of components have not yet been identified, especially the isolation, structural identification, and activity studies of monoterpenoids. As a result, the material basis of its pharmacological efficacy remains unclear, which limits the further development and application of this medicinal resource. Summary of the Invention

[0004] To address the aforementioned problems, this invention provides a monoterpenoid compound isolated from Dalbergia odorifera, its preparation method, and its application. This invention is based on (… E,E Using the 2,4-diene-3,7-dimethyloctane structure as the parent nucleus, novel monoterpenoid compounds 1 to 3 were obtained.

[0005] To achieve the above objectives, the present invention adopts the following technical solution: The first objective of this invention is to provide a monoterpene compound isolated from Dalbergia odorifera, said monoterpene compound having the following structure: ; In this context, R1, R2, and R3 groups are each independently hydrogen, hydroxyl, or C1-C5 alkoxy groups.

[0006] In a preferred embodiment of the present invention, R1, R2, and R3 groups are each independently a hydroxyl or C1-C2 alkoxy group, and the stereoconfiguration at the C-6 position of the monoterpene compound is as follows: R type or S type.

[0007] In a preferred embodiment of the present invention, R1, R2, and R3 groups are each independently hydroxyl or ethoxy, and the stereoconfiguration at the C-6 position of the monoterpene compound is as follows: R type orS type.

[0008] In a preferred embodiment of the present invention, the monoterpene compound has the following structure: , or .

[0009] A second objective of this invention is to provide a method for preparing the above-mentioned monoterpenoid compounds isolated from Dalbergia odorifera, comprising the following steps: S1. Using the branches and leaves of the rosewood as raw material, and ethanol solution as the extractant, an extract solution is obtained.

[0010] S2. After heating the extract solution, extract the extract solution with ethyl acetate as the extractant to obtain ethyl acetate extract. After separation and purification, obtain monoterpenoid compounds based on the separation of Dalbergia odorifera.

[0011] In a preferred embodiment of the present invention, the volume ratio of the branches and leaves of the rosewood to the ethanol solution is 1:2.5~3, and the ethanol solution is an aqueous solution of ethanol with a mass fraction of 95%.

[0012] In a preferred embodiment of the present invention, the heating temperature of the extract solution is 50°C to 60°C.

[0013] In a preferred embodiment of the present invention, the volume ratio of ethyl acetate to the extract solution is 1:1.

[0014] A third objective of this invention is to provide the application of the above-mentioned monoterpenoid compounds isolated from Dalbergia odorifera in anti-influenza A virus drugs.

[0015] Compared with the prior art, the beneficial effects of the present invention are: This invention provides a monoterpene compound based on Dalbergia odorifera, which is based on ( E,E Using the 2,4-diene-3,7-dimethyloctane structure as the parent core, novel monoterpenoid compounds 1-3 were obtained. This invention extracts and isolates monoterpenoid compounds from *Dalbergia odorifera*, employing a low-cost, simple preparation method that yields high-purity compounds. Monoterpenoid compounds 1-3 exhibit antiviral activity against influenza A / WSN / 33 (H1N1) virus. At a concentration of 10 mol / L, the virus infection rates in A549 cells were 16.117%, 18.323%, and 16.609%, respectively, while the virus infection rate in the blank control group was 25.446%, making them suitable for the preparation of antiviral drugs. Attached Figure Description

[0016] Figure 1 Compound 1 of the present invention 1 H NMR spectrum.

[0017] Figure 2 Compound 1 of the present invention 13 C10 NMR spectrum.

[0018] Figure 3 This is the HSQC spectrum of compound 1 of the present invention.

[0019] Figure 4 This is the HMBC spectrum of compound 1 of the present invention.

[0020] Figure 5 This is the NOESY spectrum of compound 1 of the present invention.

[0021] Figure 6 The image shows the HRESIMS spectrum of compound 1 of the present invention.

[0022] Figure 7 Compound 2 of the present invention 1 H NMR spectrum.

[0023] Figure 8 Compound 2 of the present invention 13 C10 NMR spectrum.

[0024] Figure 9 This is the HSQC spectrum of compound 2 of the present invention.

[0025] Figure 10 This is the HMBC spectrum of compound 2 of the present invention.

[0026] Figure 11 This is the NOESY spectrum of compound 2 of the present invention.

[0027] Figure 12 The image shows the HRESIMS spectrum of compound 2 of the present invention.

[0028] Figure 13 Compound 3 of the present invention 1 H NMR spectrum.

[0029] Figure 14 Compound 3 of the present invention 13 C10 NMR spectrum.

[0030] Figure 15 This is the HMBC spectrum of compound 3 of the present invention.

[0031] Figure 16 The image shows the HRESIMS spectrum of compound 3 of the present invention. Detailed Implementation

[0032] 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.

[0033] It should be noted that the technical terms used in this invention are only for the purpose of describing specific embodiments and are not intended to limit the scope of protection of this invention. Unless otherwise specified, all raw materials, reagents, instruments and equipment used in the following embodiments of this invention can be purchased from the market or prepared by existing methods.

[0034] To date, research on the chemical constituents of *Dalbergia odorifera* has largely focused on alkaloids, flavonoids, and volatile oils. These compounds have been reported to possess various pharmacological activities, including antioxidant, antidepressant, and anti-inflammatory effects. However, other types of components, particularly monoterpenes, have not been identified, and their structural identification and activity studies remain unclear. This lack of clarity regarding the pharmacodynamic basis limits the further development and application of this medicinal resource. Monoterpenes are terpenoid compounds composed of two isoprene units and are the main components of volatile oils, possessing antiseptic and analgesic properties. Related research (Ćavar Zeljković S, Schadich E, Džubák P, et al. Antiviral Activity of Selected Lamiaceae Essential Oils and Their Monoterpenes Against SARS-Cov-2. Front Pharmacol. 2022 May 2;13:893634.) has reported some monoterpene derivatives with antiviral activity. However, research on the monoterpenes in *Dalbergia odorifera* volatile oils and their antiviral activity remains unclear.

[0035] Based on this, firstly, the present invention provides a monoterpene compound isolated from Dalbergia odorifera, which is based on ( E,E The monoterpene compound has the following structure as its parent nucleus: 2,4-diene-3,7-dimethyloctane. .

[0036] In this configuration, R1, R2, and R3 are each independently hydrogen, hydroxyl, or C1-C5 alkoxy groups, and the stereoconfiguration at the C-6 position is as follows: R type or S type.

[0037] The R1, R2, and R3 groups are each independently a hydroxyl or C1-C2 alkoxy group, and the stereoconfiguration at the C-6 position of the monoterpene compound is as follows: R type or S type.

[0038] The R1, R2, and R3 groups are each independently hydroxyl or ethoxy, and the stereoconfiguration at the C-6 position of the monoterpene compound is as follows: R type or S type.

[0039] The monoterpenoid compounds isolated from *Palmaria rubra* are compound 1, compound 2, or compound 3. Compound 1 is (…). 6R, 2E, 4E )-3,7-dimethyloctane-1-ethoxy-2,4-diene-6,7-diol, in compound 1, R1 group is ethoxy, R2 group is hydroxyl, R3 group is hydroxyl, and the stereoconfiguration at C-6 position is R Type. The structural formula of compound 1 is shown below:

[0040] .

[0041] Compound 2 is ( 6S, 2E, 4E Compound 2, consisting of 3,7-dimethyloctane-2,4-diene-6-ethoxy-1,7-diol, has R1 (hydroxyl), R2 (ethoxy), and R3 (hydroxyl) groups. Its stereoconfiguration at the C-6 position is as follows: S Type. The structural formula of compound 2 is shown below:

[0042] .

[0043] Compound 3 is ( 6R, 2E, 4E Compound 3, 3-dimethyloctane-2,4-diene-1,6,7-triol, has R1, R2, and R3 groups as hydroxyl groups, and its stereoconfiguration at the C-6 position is as follows: R Type. The structural formula of compound 3 is shown below:

[0044] .

[0045] Secondly, this invention provides a method for preparing the above-mentioned monoterpenoid compounds isolated from Dalbergia odorifera, comprising the following steps: S1. Using the branches and leaves of the rosewood as raw material, and ethanol solution as the extractant, an extract solution is obtained.

[0046] S2. After heating the extract solution, extract the extract solution with ethyl acetate as the extractant to obtain ethyl acetate extract. After separation and purification, obtain monoterpenoid compounds based on the separation of Dalbergia odorifera.

[0047] The volume ratio of the branches and leaves of the rosewood to the ethanol solution is 1:2.5~3, and the ethanol solution is an aqueous solution of ethanol with a mass fraction of 95%.

[0048] The hot water dissolution temperature for adding the extract solution is 50℃~60℃.

[0049] The volume ratio of ethyl acetate to the extract solution is 1:1.

[0050] Finally, this invention provides an application of the above-mentioned monoterpenoid compounds isolated from Dalbergia odorifera.

[0051] The specific process of the application is as follows: 24 hours before infection, A549 cells are inoculated at a concentration of 1.5 × 10⁻⁶. 4 Cells were seeded at a density of cells / well in 96-well plates. Two hours prior to infection, a prophylactic treatment was performed by adding 10 μmol / L of a Dalbergia odorifera-based monoterpene compound to the culture medium. Influenza A virus A / WSN / 33 (H1N1) was inoculated into cells at a multiplicity of infection (MOI) of 30. One hour after virus adsorption, the inoculum was removed, and the medium was replaced with maintenance medium containing 10 μmol / L monoterpene compound and 2% fetal bovine serum (FBS). Eight hours after infection, cells underwent digestion, fixation, permeabilization, and immunostaining. Digestion was performed using 0.25% trypsin-EDTA, and fixation was performed using 4% paraformaldehyde at 4°C for 30 min. Permeabilization was performed for 15 min using saponin-based buffer (Hank's balanced salt solution containing 1 g / L saponin, 10 mM 4-hydroxyethylpiperazine ethanesulfonic acid (HEPES) [pH=7.4], and 0.025% sodium azide). Immunostaining was performed by incubating with mouse anti-influenza virus nucleoprotein monoclonal antibody for 90 min, washing three times with permeation buffer, and then incubating with AF647-labeled goat anti-mouse IgG (H+L) secondary antibody for 45 min.

[0052] The following specific examples will provide further explanation.

[0053] Example 1 A monoterpene compound isolated from Dalbergia odorifera is based on ( E,E The core is composed of 2,4-diene-3,7-dimethyloctane. Compounds 1 through 3 have the following structures sequentially:

[0054] , and .

[0055] The above-mentioned method for preparing monoterpenoid compounds isolated from Dalbergia odorifera includes the following steps: S1. Pulverize the dried branches and leaves of the rosewood, and extract them three times with an ethanol solution of 95% by mass at a volume ratio of 1:3. After concentration, obtain the extract.

[0056] S2. Dissolve the ethanol extract in hot water, extract with ethyl acetate, and concentrate to obtain the organic phase, i.e., the ethyl acetate extract.

[0057] S3. The ethyl acetate extract was separated by MCI column chromatography with a water-methanol gradient elution (80:1→0:100) to obtain eight fractions (OHP-A~OPH-H). OPH-C was then purified sequentially by normal-phase silica gel column chromatography, gel column chromatography, and semi-preparative high-performance liquid chromatography (methanol:water = 55:45) to obtain compound 1 (t). R =23min, 8.3mg), compound 2 (t R =24min, 7.7mg) and compound 3 (t R =15min, 4.5mg). Its structure was identified by NMR and MS spectroscopy.

[0058] Structural analysis was performed on compounds 1 and 3 obtained in Example 1.

[0059] Structural identification of compound 1: Compound 1 isolated in Example 1 was a pale yellow oil. D 23.6 +24.7 (c0.05 methanol), HRESIMS ( Figure 6 (Given the molecular ion peak) m / z 237.1456 [M+Na] + (Calculated value C) 12 H 22 O3Na, 237.1466), the molecular formula of this compound was determined to be C 12 H 22 O3 has an unsaturation degree of 2. 1 H NMR, 13 C10 NMR spectrum and HSQC two-dimensional spectrum ( Figure 1 , Figure 2 and Figure 3 The results showed that compound 1 had 12 carbon signals, including three singlet methyl (δ) peaks. H 1.15, 1.15, 1.81; δ C 25.8, 25.4, 12.9), two olefin groups (δ H 5.61, 6.32, 5.81; δ C 128.8, 137.7, 137.3, 129.4), one hydroxymethylene group (δ-hydroxymethylene group). H 4.14; δC 67.9), one hydroxymethyl group (δ) H 3.89; δ C 80.5), a quaternary carbon atom (δ) C 73.7) and an oxyethyl group (δ) H 3.51, q, J =7.0Hz; 1.19, t, J =7.0Hz; δ C (67.9, 15.5). These characteristics indicate that compound 1 is a monoterpene compound containing two double bonds and one ethoxy group.

[0060] In the HMBC two-dimensional spectrum ( Figure 4 The correlation signal between H-1 and C-1 confirms that the oxyethyl group is attached to C-1. H 2 -1 / C-2, H-1 / C-3, C H 3 -10 / C-1、C H 3 -10 / C-2\C H 3 The HMBC-related signals of -10 / C-4, H-2 / C-4, and H-5 / C-3 indicate that the two double bonds are... 2,3 and 4,5 And they are conjugate. The coupling constant between H-4 and H-5 is 15.7 Hz, indicating that... 4,5 The double bond is of type E. NOESY related signals ( Figure 5 C H 2 -1 / C H 3 -10, H-2 / H-4, C H 3 -10 / H-5 can also indicate conjugated double bonds. 2,3 and 4,5 for E Configuration. H-6 with C-4 and C-5, C H 3 -8 or C H 3 -9 exhibits HMBC-related signals with C-6 and C-7, confirming that the two hydroxyl groups are located at C-6 and C-7. Therefore, the planar structure of compound 1 is determined to be ( 2E, 4E )-3,7-dimethyloctane-1-ethoxy-2,4-diene-6,7-diol. To determine the stereoconfiguration of the chiral center C-6, we compared the optical rotation of compound 1 with that of similar compounds in the literature, and used calculations to determine the specific rotation. By comparing the specific rotations of the literature compounds: ( R,E)-8-(allyloxy)-2,6-dimethyloct-6-ene-2,3-diol ( D +26.1) and ( 3S, 4E, 6E )-2-methyldeca-4,6-diene-2,3-diol ( D 27.2), we infer that compound 1 ( D 23.6 The absolute configuration of C-6 is +24.7). R We performed conformational analysis using the Spartan'08 program, optimized the force field using MMFF94, and calculated the 6... S The specific rotation value of -1 is D -49.6, opposite to the direction of the measured value, further confirms that the absolute configuration of C-6 of compound 1 is... R Based on the above analysis, the structure of compound 1 is determined to be ( 6R, 2E, 4E )-3,7-dimethyloctane-1-ethoxy-2,4-diene-6,7-diol. In compound 1, the R1 group is ethoxy, and the R2 and R3 groups are hydroxyl groups. The stereoconfiguration at the C-6 position is... R type.

[0061] Structural identification of compound 2: Compound 2 isolated in Example 1 was a pale yellow oily substance, α D 23.6 -42.8° (c 0.05 methanol), HRESIMS ( Figure 12 The molecular ion peak given m / z 237.1471 [M+Na] + (Calculated value: 237.1466) Same as compound 1, both have the same molecular formula C 12 H 22 O3. Compound 2 and Compound 1 1 H, 13 C and HSQC NMR data are similar ( Figure 7 , Figure 8 and Figure 9 This indicates that the two structures are similar. Analysis of the correlation signals in the HMBC spectrum of compound 2 (…) Figure 10 ), C H 2 -1 / C-2, H-1 / C-3, C H 3 - 10 / C-1, C H 3 -10 / C-2、C H 3-10 / C-4, H-2 / C-4, H-5 / C-3, H-6 / C-4, H-6 / C-5, and C H 3 -8 or C H 3 The correlation signal between -9 and C-6 and C-7 indicates that compound 2 has three oxygen bonds at C-1, C-6 and C-7, and the double bond is located at... 2,3 and 4,5 Monoterpenoid compounds. The coupling constant between H-4 and H-5 is 15.8 Hz, and C... H 2 -1 / C H 3 -10, C H 3 NOESY related signals for -10 / H-5 and H-2 / H-4 ( Figure 11 This indicates that the conjugated double bond is also... E Configuration. Unlike compound 1, compound 2 exhibits an H-1 and C-6 HMBC correlation signal, indicating that the ethoxy group is attached to C-6. Therefore, the structure of compound 2 is determined to be ( 2E, 4E )-3,7-dimethyloctane-2,4-diene-6-ethoxy-1,7-diol. Compared with compound 1, compound 2 has a specific rotation value of (α) D 23.6 -42.8°), indicating that its C-6 may be S Configuration. Calculated using Gaussian09, 6 S The specific rotation value of -2 is α D -13.7, the calculated value and the measured value are in the same direction, further confirming that C-6 of compound 2 is... S Configuration. Therefore, compound 2 was determined to be ( 6S, 2E, 4E )-3,7-dimethyloctane-2,4-diene-6-ethoxy-1,7-diol. In compound 2, R1 and R3 groups are hydroxyl groups, R2 group is an ethoxy group, and the stereoconfiguration at the C-6 position is... S type.

[0062] Structural identification of compound 3: Compound 3 isolated in Example 1 was a pale yellow oily substance, α D 23.6 +35.2 (c 0.05 methanol), HRESIMS ( Figure 16 (Given the molecular ion peak) m / z 209.1142 [M+Na] + (Calculated value C) 10 H 18O3Na, 209.1153), the molecular formula of this compound was determined to be C 10 H 18 O3. 1 H NMR and 13 C NMR spectrum ( Figure 13 and Figure 14 The results showed that compound 3 had 10 carbon signals. Compared with compound 1, compound 3 was essentially identical to compound 1 except for the lack of an ethoxy group signal. Therefore, it was inferred that compound 3 was a deethoxylated derivative of compound 1, and this structure was confirmed by the HMBC correlation signal (…). Figure 15 The structure of compound 3 was further determined. Furthermore, the optical rotation of compound 3 is in the same direction as that of compound 1, thus the structure of compound 3 can be further deduced as (…). 6R, 2E, 4E 3,7-Dimethyloctane-2,4-diene-1,6,7-triol. The R1, R2, and R3 groups of compound 3 are all hydroxyl groups, and the stereoconfiguration at the C-6 position is... R type.

[0063] Then, compounds 1-3 were tested for their application in antiviral drugs, i.e., antiviral activity testing. This specifically included the following steps:

[0064] S1. A549 cells were inoculated at a concentration of 1.5 × 10⁻⁶. 4 Inoculation was performed in 96-well plates at a density of cells / well, with plate formation completed 24 hours prior to infection. Sixteen hours after plate formation (i.e., 2 hours prior to infection, marked as -2hpi), prophylactic treatment was initiated by adding 10 μmol / L of isolated compounds 1–3 to the culture medium, followed by inoculation with influenza A / WSN / 33 (H1N1) virus at a multiplicity of infection (MOI) of 30. One hour after virus adsorption (1hpi), the inoculum was removed and replaced with maintenance medium (DMEM basal) containing 2% FBS and 10 μmol / L of the compounds.

[0065] S2. Eight hours post-infection (8 hpi), cells were digested with 0.25% trypsin-EDTA and fixed with 4% paraformaldehyde (PFA) at 4°C for 30 min. Permeabilization was performed for 15 min using saponin-based buffer (Hank's balanced salt solution containing 1 g / L saponin, 10 mM HEPES [pH=7.4], and 0.025% sodium azide). Immunostaining was performed by incubation for 90 min with mouse anti-influenza virus nucleoprotein (NP) monoclonal antibody (MAB8528, 1:1000 dilution), followed by washing three times with permeabilization buffer and incubation for 45 min with AF647-labeled goat anti-mouse IgG (H+L) (A0473, 1:500 dilution).

[0066] S3. The final cell suspension was resuspended in 100 μL of flow cytometry buffer (PBS + 2% FBS) and analyzed using a Beckman CytoFLEX S flow cytometer. Viral infection efficiency was quantitatively calculated using CytExpert 2.4 analysis software, with a fluorescence intensity higher than that of the uninfected control group as the gating criterion.

[0067] The above tests showed that compounds 1-3, at a concentration of 10 mol / L, resulted in virus infection rates of 16.117%, 18.323%, and 16.609% in A549 cells, respectively, compared to a virus infection rate of 25.446% in the blank control group. This indicates that the compounds obtained in this invention have an inhibitory effect on the binding of influenza A / WSN / 33 (H1N1) virus to host cells A549.

[0068] It should be noted that when numerical ranges are involved in this invention, it should be understood that both endpoints of each numerical range, as well as any value between the two endpoints, can be selected. Since the steps and methods used are the same as in the embodiments, preferred embodiments are described here to avoid redundancy. Although preferred embodiments of this invention have been described, those skilled in the art, once they understand the basic inventive concept, can make other changes and modifications to these embodiments. Therefore, the appended scope of protection is intended to be interpreted as including the preferred embodiments and all changes and modifications falling within the scope of this invention.

[0069] Obviously, those skilled in the art can make various modifications and variations to this invention without departing from its spirit and scope. Therefore, if these modifications and variations fall within the scope of protection of this invention and its equivalents, this invention also intends to include these modifications and variations.

Claims

1. A monoterpene compound isolated from Dalbergia odorifera, characterized in that, The monoterpene compound has the following structure: ； In this context, R1, R2, and R3 groups are each independently hydrogen, hydroxyl, or C1-C5 alkoxy groups.

2. The monoterpenoid compound isolated from Dalbergia odorifera according to claim 1, characterized in that, R1, R2, and R3 groups are each independently a hydroxyl or C1-C2 alkoxy group, and the stereoconfiguration at the C-6 position of the monoterpene compound is as follows: R Type or S type.

3. The monoterpenoid compound isolated from Dalbergia odorifera according to claim 2, characterized in that, R1, R2, and R3 groups are each independently hydroxyl or ethoxy, and the stereoconfiguration at the C-6 position of the monoterpene compound is as follows: R Type or S type.

4. The monoterpene compound isolated from Dalbergia odorifera according to claim 3, characterized in that, The monoterpene compound has the following structure: , or .

5. A method for preparing monoterpenoid compounds isolated from Dalbergia odorifera according to any one of claims 1 to 4, characterized in that, Includes the following steps: Using the branches and leaves of the rosewood as raw materials and ethanol solution as the extraction solvent, an extract was obtained. After dissolving the extract in hot water, the extract solution was extracted with ethyl acetate as the extractant to obtain an ethyl acetate extract. After separation and purification, monoterpenoid compounds based on the extract obtained from Dalbergia odorifera were obtained.

6. The method for preparing monoterpenoid compounds isolated from Dalbergia odorifera according to claim 5, characterized in that, The volume ratio of the branches and leaves of the Dalbergia odorifera to the ethanol solution is 1:2.5~3, and the ethanol solution is a 95% ethanol aqueous solution.

7. The method for preparing monoterpenoid compounds isolated from Dalbergia odorifera according to claim 5, characterized in that, The heating temperature of the extract solution is 50℃~60℃.

8. The method for preparing monoterpenoid compounds isolated from Dalbergia odorifera according to claim 5, characterized in that, The volume ratio of ethyl acetate to the extract solution is 1:

1.

9. The use of a monoterpene compound isolated from Dalbergia odorifera according to any one of claims 1 to 4 in an anti-influenza A virus drug.

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