A method for extracting iridoid glycosides or benzaldehyde compounds from plants

Abstract

The invention discloses a method for extracting iridoid ether terpenoid glycoside compounds 2-O- p ‑Coumaroyl‑loganin or a method for benzaldehyde compounds 3,5‑dimethoxy‑4‑hydroxybenzaldehyde: it uses dried white flower patrinia as raw material, crushes and extracts with ethanol, and concentrates under reduced pressure to obtain an extract; the extract is dissolved in methanol, a macroporous resin is mixed with a sample column, and water, 20% ethanol, 40% ethanol, 60% ethanol, 80% ethanol and 95% ethanol are used in sequence for gradient elution, and a 40% ethanol elution part is collected and concentrated under reduced pressure to obtain a 40% ethanol part extract; then a silica gel column is passed, and a dichloromethane‑methanol with a volume ratio of 10:1 is eluted to obtain an iridoid glycoside compound; or a silica gel column is passed, and a dichloromethane‑methanol with a volume ratio of 30:1 is eluted to obtain a benzaldehyde compound. The present invention is conducive to better development and utilization of the medicinal and edible dual-purpose plant of white flower patrinia or spotted flower patrinia, and clarifies its pharmacodynamic material basis; the extraction process is simple, the solvent can be recycled, the extraction amount is high, and it is suitable for industrial production.

Description

Technical Field

[0001] The invention belongs to the technical field of plant extraction, and particularly relates to a method for extracting iridoid ether terpenoid glycoside compounds 2-O- p -Coumaroyl-loganin or benzaldehyde compound 3,5-dimethoxy-4-hydroxybenzaldehyde method. Background Art

[0002] Patrinia odorata Patrinia villosa (Thunb.) Juss.), also known as climbing up the steamer, is a member of the genus Valerianaceae. Patrinia Juss . ) plant, mainly distributed in Guizhou, Hunan, Hubei and Henan in China. Patrinia dahurica is bitter and cold in nature. It has the effects of clearing away heat and detoxifying, dispersing blood stasis and reducing swelling, promoting blood circulation and discharging pus. It can be used to treat appendicitis, dysentery, hepatitis, tonsillitis, carbuncle, sore and other diseases.

[0003] The natural compound iridoid glycoside 2-O- p -Coumaroyl-loganin was first extracted and isolated from Patrinia odorata, a plant of the genus Patrinia, and belongs to the class of iridoid glycosides. This class of compounds and their glycosides are widely distributed in plants, and are more common in plants such as Scrophulariaceae, Patriniaceae, and Gentianaceae. According to literature reports, iridoid glycosides have analgesic, anti-inflammatory, and blood pressure-lowering and blood sugar-lowering effects. p -Coumaroyl-loganin has broad application prospects. However, there is no research on extracting 2-O- p -Coumaroyl-loganin reports.

[0004] Patrinia punctata Patriniapunctiflora ) belongs to the genus Valerianaceae ( Patrinia Juss . ) plant. Patrinia scabra has the effects of anti-inflammatory, decongestion, pus discharge and diuresis. People often soak its roots in wine and take it orally to treat bruises, and apply its leaves externally to wash sores.

[0005] The natural compound 3,5-dimethoxy-4-hydroxybenzaldehyde involved in the present invention is extracted and separated from the Patrinia scabra plant Patrinia scabra for the first time, and belongs to the benzaldehyde compound. 3,5-dimethoxy-4-hydroxybenzaldehyde is also known as syringaldehyde. Syringaldehyde is mostly found in the genus Syringa of the family Oleaceae. Syringaldehyde has strong floral, green and sweet fragrances and is a green flower fragrance chemical. It is used in daily chemical flavors, beauty products, soaps, laundry care, household products, and is also used in the preparation of various fruit flavors such as almonds and cherries and vanilla flavors. Modern pharmacology shows that syringaldehyde has antioxidant and anti-inflammatory effects, as well as cardioprotective effects; its cardioprotective effect is achieved by defending against myocardial damage mediated by ROS, lipid peroxidation, and inflammation ISO. Therefore, foods rich in syringaldehyde may help alleviate the effects of ROS in cardiovascular diseases such as myocardial infarction and angina pectoris. Syringaldehyde exerts an anti-hyperglycemic effect in a diabetic rat model induced by streptozotocin. In addition to its antioxidant capacity, syringaldehyde also has anti-inflammatory activity. It was found to inhibit cyclooxygenase-2 (COX-2) in a mouse macrophage cell line in a dose-dependent manner with an IC50 of 3.5 μg / mL. It also provides comprehensive protection against Salmonella-infected mice by reducing the transcription level of hiLD-hiLC-rstA-hiLA regulatory factors to inhibit T3SS function, and may become a potential compound for the treatment of Salmonella infection. 3,5-dimethoxy-4-hydroxybenzaldehyde (syringaldehyde) has broad application prospects, however, there is no report on the extraction of 3,5-dimethoxy-4-hydroxybenzaldehyde from Patrinia plants. Summary of the invention

[0006] In order to overcome the defects of the prior art, the present invention aims to provide a method for extracting iridoid ether terpenoid glycosides 2-O- p The method for preparing 3,5-dimethoxy-4-hydroxybenzaldehyde from 1,2-Coumaroyl-loganin or a benzaldehyde compound is simple in extraction process, the solvent can be recycled, the extraction rate is high, and the method is suitable for industrial production.

[0007] In order to achieve the above object, the present invention adopts the following technical solution:

[0008] A method for extracting iridoid glycosides or benzaldehyde compounds from plants, comprising the following steps:

[0009] 1) Using dried Patrinia dahurica as raw material, crushing and then extracting with ethanol to obtain an extract, and recovering the solvent under reduced pressure to obtain an extract concentrate; dissolving the extract concentrate with methanol, mixing the sample into an appropriate amount of macroporous resin column, loading the column, and eluting with water, 20% ethanol, 40% ethanol, 60% ethanol, 80% ethanol and 95% ethanol in sequence, collecting the 40% ethanol elution part, and recovering the solvent after decompression concentration to obtain a 40% ethanol part extract;

[0010] 2) Dissolve the 40% ethanol extract with methanol and mix the sample into silica gel. Load the sample onto a silica gel column and elute with dichloromethane-methanol in a volume ratio of 10:1. Perform thin layer chromatography detection, combine the same components and recover the solvent under reduced pressure to obtain a crude product of iridoid glycosides.

[0011] or,

[0012] 1) using dried Patrinia punctata as raw material, crushing it and then extracting it with ethanol to obtain an extract, and recovering the solvent under reduced pressure to obtain an extract concentrate; dissolving the extract concentrate with methanol-water solution (preferably methanol-water with a volume ratio of 2:1), loading the extract onto a macroporous resin column, and eluting it with 20% ethanol, 40% ethanol, 60% ethanol and 95% ethanol in a gradient manner in sequence, and collecting the 40% ethanol elution portion;

[0013] 2) Dissolve the 40% ethanol elution portion with methanol, mix the sample and inject it into silica gel column, elute with dichloromethane-methanol in a volume ratio of 30:1, detect by thin layer chromatography, combine the same components and recover the solvent under reduced pressure to obtain the crude benzaldehyde compound.

[0014] Specifically, in step 1), after crushing, ethanol is used for extraction 2-4 times at 20-55°C, the extracts are combined, and the solvent is recovered under reduced pressure to obtain an extract. More preferably, the white flower Patrinia is extracted at room temperature of 20-30°C, and each extraction is 6-7 days; the spotted flower Patrinia is extracted at 45-55°C, and each extraction is 2-4 hours.

[0015] Specifically, in step 1), the volume concentration of ethanol is 70±10%, preferably 70-80%.

[0016] Specifically, in step 2), the 40% ethanol extract or the 40% ethanol elution portion is mixed with 300-400 mesh silica gel at a weight ratio of 1:3-5 and then loaded onto the column, preferably at a weight ratio of 1:3-4.

[0017] Furthermore, in order to obtain a higher purity of the iridoid glycosides, in step 2), the obtained crude iridoid glycosides were dissolved in methanol and then mixed into silica gel, loaded onto a silica gel column, and then eluted with a gradient of dichloromethane-methanol at a volume ratio of 30:1, 20:1, 10:1, 5:1, 3:1, and 1:1, and then combined by thin layer chromatography to obtain 10 components, which were marked as components Fr.1 to Fr.10 in ascending order according to the polarity of the obtained components;

[0018] Component Fr.5 was dissolved in methanol and mixed into silica gel. After loading onto a silica gel column, it was eluted with dichloromethane-methanol in a volume ratio of 10:1. Thin layer chromatography was performed. The same components were combined and the solvent was recovered under reduced pressure to obtain 6 components, which were marked as components Fr.5-1 to Fr.5-6 in order of polarity from small to large.

[0019] The component Fr.5-3 was dissolved in methanol, purified by Sephadex LH-20 gel chromatography column, eluted with methanol, detected by thin layer chromatography, and the same components were combined and the solvent was recovered under reduced pressure to obtain 3 components, which were labeled as components Fr.5-3-1 to Fr.5-3-3 in descending order according to the molecular weight of the obtained components;

[0020] The component Fr. 5-3-2 was dissolved in methanol, mixed and poured into silica gel column, eluted with dichloromethane-methanol in a volume ratio of 25:1, detected by thin layer chromatography, combined with the same components and recovered the solvent under reduced pressure to obtain Fr.5-3-2-1; Fr. 5-3-2-1 was dissolved, purified by Sephadex LH-20 gel chromatography column, eluted with methanol, detected by thin layer chromatography, combined with the same components and recovered the solvent under reduced pressure to obtain Fr. 5-3-2-1-1; Fr. 5-3-2-1-1 was separated and purified by semi-preparative high performance liquid phase separation, eluted with 52% methanol-water, and the peak time t was collected. R The compound with a reaction time of about 23.56 min is the pure product of cyclopentadiene ether terpene glycoside compound.

[0021] The pure iridoid glycosides obtained by extraction and separation of the present invention are 2-O- p-Coumaroyl-loganin, chemical name methyl (1S,4aS,6S,7R,7aS)-1-(((3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-((E)-3-(4-hydroxyphenyl)acryloyl)oxy) tetrahydro-2H-pyran-2-yl)oxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate, molecular formula: C 26 H 32 O 12 , molecular weight: 536.19, its structural formula is as follows:

[0022] .

[0023] Furthermore, in order to obtain a higher purity of benzaldehyde compounds, in step 2), the obtained crude benzaldehyde compounds were mixed with silica gel and loaded on a column, eluted with dichloromethane-methanol in a volume ratio of 30:1, and detected by thin layer chromatography. The same components were combined and the solvent was recovered under reduced pressure to obtain 11 components, which were marked as components Fr.1~11 in order from small to large polarity;

[0024] After dissolving component Fr.1 with methanol, the sample was mixed with silica gel and loaded onto a flash column, and eluted with a gradient of dichloromethane-methanol with a volume ratio of 100:1 to 10:1 (specifically 100:1, 90:1, 80:1, 70:1, 60:1, 50:1, 40:1, 30:1, 20:1, 10:1), and detected by thin layer chromatography. The same components were combined and the solvent was recovered under reduced pressure to obtain 8 components, which were labeled as components Fr.1-1 to Fr.1-8 in order of polarity from small to large.

[0025] Dissolve the components Fr.1-4 in methanol, purify them with a Sephadex LH-20 gel chromatography column, elute with methanol, and detect them with thin layer chromatography. Combine the same components and recover the solvent under reduced pressure to obtain three components, which are labeled as components Fr.1-4-1 to Fr.1-4-3 in descending order according to their molecular weights.

[0026] Dissolve component Fr.1-4-3 in methanol, mix the sample with silica gel, place it on a vacuum column, elute with dichloromethane-methanol in a volume ratio of 100:1, detect by thin layer chromatography, combine the same components and recover the solvent under reduced pressure to obtain pure benzaldehyde compounds.

[0027] The pure benzaldehyde compound obtained by extraction and separation of the present invention is 3,5-dimethoxy-4-hydroxybenzaldehyde, chemical name syringaldehyde, molecular formula: C9H 10 O4, molecular weight: 182, its structural formula is as follows:

[0028] .

[0029] Compared with the prior art, the present invention has the following beneficial effects:

[0030] 1) So far, the present invention is the first to obtain iridoid ether terpenoid glycoside compounds, such as 2-O- p -Coumaroyl-loganin, the present invention provides a method for extracting and separating the iridoid glycosides from Patrinia dasyphylla, which is conducive to better development and utilization of Patrinia dasyphylla as a medicinal plant; at the same time, up to now, there has been no report on extracting the benzaldehyde compound 3,5-dimethoxy-4-hydroxybenzaldehyde from the whole plant of Patrinia dasyphylla. The present invention provides a method for extracting and separating the benzaldehyde compound from Patrinia dasyphylla, which is conducive to better development and utilization of Patrinia dasyphylla as a medicinal plant;

[0031] 2) The extraction process of the present invention has the advantages of being simple, convenient, fast, green and environmentally friendly, having high yield and purity, and the solvent can be recycled, and is suitable for industrial production;

[0032] 3) The iridoid glycoside compounds and benzaldehyde compounds of the present invention have extensive biological activities and are available in abundant raw material sources; the extraction method of the present invention facilitates in-depth research on them and provides a basis for promoting their extensive development in the pharmaceutical industry.

[0033] 4) The extraction process of the present invention is simple and easy to obtain 2-O- p -Coumaroyl-loganin monomer, 3,5-dimethoxy-4-hydroxybenzaldehyde monomer, and the solvent can be recycled, the extraction amount is high, and it is suitable for industrial production. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1 For compound 2-O- p -Coumaroyl-loganin 1 H spectrum (500 MHZ, CD3OD);

[0035] Figure 2 For compound 2-O- p -Coumaroyl-loganin 13 C spectrum (125 MHZ, CD3OD);

[0036] Figure 3 The compound 3,5-dimethoxy-4-hydroxybenzaldehyde 1 H spectrum (500 MHZ, CD3OD);

[0037] Figure 4 The compound 3,5-dimethoxy-4-hydroxybenzaldehyde 13 C spectrum (125 MHZ, CD3OD). DETAILED DESCRIPTION

[0038] In order to make the technical purpose, technical scheme and beneficial effects of the present invention clearer, the technical scheme of the present invention is further described below in conjunction with specific embodiments. However, the embodiments are intended to explain the present invention and cannot be understood as limiting the present invention. If no specific technology or conditions are specified in the embodiments, the technology or conditions described in the literature in the field or the product manual shall be followed.

[0039] In the following examples, the whole herb of Patrinia leucoderma and Patrinia maculata as raw materials were collected from Guiyang City, Guizhou Province; the concentrations of ethanol and methanol are volume concentrations unless otherwise specified.

[0040] Example 1

[0041] A method for extracting iridoid glycosides from the whole herb of Patrinia leucoderma, comprising the following steps:

[0042] 1) 3 kg of dried whole herb of Patrinia leucoderma with roots was used as raw material, crushed and then extracted with 70% ethanol to obtain an extract (immersed and extracted 3 times at 25℃, 7 days each time, and the extracts were combined; the amount of 70% ethanol added in each extraction was 35L), and the solvent was recovered under reduced pressure to obtain an extract concentrate; the extract concentrate was dissolved in methanol, mixed and injected into a D-101 macroporous resin column, loaded on the column, and gradient eluted with water, 20% ethanol, 40% ethanol, 60% ethanol, 80% ethanol and 95% ethanol in sequence, and the 40% ethanol elution portion was collected, concentrated under reduced pressure and then the solvent was recovered to obtain a 40% ethanol extract;

[0043] 2) After dissolving the 40% ethanol extract with methanol, the sample was mixed with 300-400 mesh silica gel at a weight ratio of 1:5 and loaded into a column, eluted with dichloromethane-methanol at a volume ratio of 10:1, and detected by thin layer chromatography. The same components were combined and the solvent was recovered under reduced pressure to obtain a crude product of iridoid glycosides;

[0044] 3) The crude iridoid glycoside compound obtained in step 2) was dissolved in methanol and then mixed into silica gel. After loading onto a silica gel column, the column was eluted with a gradient of dichloromethane-methanol at a volume ratio of 30:1, 20:1, 10:1, 5:1, 3:1, and 1:1. The components were combined and the solvent was recovered under reduced pressure to obtain 10 components, which were marked as components Fr. 1 to 10 in order of polarity from small to large.

[0045] Component Fr.5 was dissolved in methanol and mixed into silica gel. After loading onto a silica gel column, it was eluted with dichloromethane-methanol in a volume ratio of 10:1. Thin layer chromatography was performed. The same components were combined and the solvent was recovered under reduced pressure to obtain 6 components, which were marked as components Fr.5-1 to Fr.5-6 in order of polarity from small to large.

[0046] The component Fr.5-3 was dissolved in methanol, purified by Sephadex LH-20 gel chromatography column, eluted with methanol, detected by thin layer chromatography, and the same components were combined and the solvent was recovered under reduced pressure to obtain 3 components, which were labeled as components Fr.5-3-1 to Fr.5-3-3 in descending order according to the molecular weight of the obtained components;

[0047] The component Fr. 5-3-2 was dissolved in methanol and mixed with the sample and loaded into a silica gel column, eluted with dichloromethane-methanol in a volume ratio of 25:1, detected by thin layer chromatography, combined with the same components and recovered the solvent under reduced pressure to obtain Fr.5-3-2-1; Fr. 5-3-2-1 was dissolved in methanol, purified by Sephadex LH-20 gel chromatography column, eluted with methanol, detected by thin layer chromatography, combined with the same components and recovered the solvent under reduced pressure to obtain Fr.5-3-2-1-1; Fr. 5-3-2-1-1 was separated and purified by semi-preparative high performance liquid phase separation, eluted with 52% methanol-water, and the peak time t was collected. R The compound with a reaction time of about 23.56 min is the pure product of cyclopentadiene ether terpene glycoside compound.

[0048] The pure iridoid ether terpene glycoside compound 2-O- p -Coumaroyl-loganin is a colorless and odorless solid with a yield of about 0.001% and a purity of 90%.

[0049] The above-prepared pure 2-O- p -Coumaroyl-loganin was identified using a variety of spectroscopic techniques, as follows:

[0050] Instruments and materials: UV was measured on a UV-210A spectrometer; 1H, 13C NMR spectra were measured on a Brukeram-500 MHz nuclear magnetic resonance spectrometer. TMS was used as an internal standard. See the spectra at Figure 1 and Figure 2The experimental results are as follows:

[0051] 2-O- p -Coumaroyl-loganin, white solid, m / z : 536 , Molecular formula: C 26 H 32 O 12 , 1 H(CD3OD, 500 MHz) δ H :7.66 (2H, dd, J = 9.1, 2.7 Hz, H-2′′, 6′′), 7.46 (1H, m,H-7′), 7.26 (1H, d, J = 0.9 Hz, H-3), 6.80 (1H, d, J = 13.0 Hz, H-8′ ), 6.72( 2H, dd, J = 9.2, 2.4 Hz, H-3′′, 5′′), 5.36 (1H, d, J = 2.76 Hz, H-1), 4.82(2H, m, H-2′), 4.78 (1H, d, J = 9.30 Hz, H-1′), 3.69 (1H, m, H-7), 3.55 (1H,m, H-3′), 3.47 (3H, s, -COOCH3), 2.94 (1H, m, H-5), 2.08 (1H, m, H-6a), 1.73(1H, m, H-8), 1.64 (1H, m, H-6b), 1.06 (3H, d, J=6.9, H-10). 13 C-NMR (CD3OD, 125 MHz) δ C: 168.9 (C-11), 168.0 (C-9′′), 161.3 (C-4′′), 150.4 (C-3), 146.4(C-7′′), 131.3 (C-2′′, 6′′), 127.2 (C-1′′), 116.8 (C-3′′, 5′′), 115.7 (C-8′′), 115.0 (C-4), 97.6 (C-1′), 96.0 (C-1′), 78.5 (C-5′), 75.9 (C-3′), 75.1(C-7), 74.6 (C-2′7), 71.6 (C-4′), 62.6 (C-6′), 51.4 (-OCH3), 46.4 (C-9), 42.0(C-6), 41.2(C-8), 30.8(C-5), 12.5(C-10).

[0052] Inspection: TLC showed no fluorescence at UV 254 nm. Sulfuric acid colorimetric agent was used for color development at 110°C for 3 minutes, and purple color was observed.

[0053] Example 2

[0054] A method for extracting benzaldehyde compounds from the whole herb of Patrinia punctata, comprising the following steps:

[0055] 1) 15 kg of dried whole herb of Patrinia punctata with roots was used as raw material, crushed and then extracted with 75% ethanol to obtain an extract (immersed and extracted 3 times at 50°C, each time for 3 hours, and the extracts were combined; the amount of 75% ethanol added in each extraction was 50 L), and the solvent was recovered under reduced pressure to obtain an extract concentrate; the extract concentrate was dissolved in methanol-water with a volume ratio of 2:1, loaded on a D-101 macroporous resin column, and gradient eluted with 20% ethanol, 40% ethanol, 60% ethanol and 95% ethanol in sequence, and the 40% ethanol elution portion was collected;

[0056] 2) The 40% ethanol elution portion was mixed with 300-400 mesh silica gel at a weight ratio of 1:4 and loaded into a column, eluted with dichloromethane-methanol at a volume ratio of 30:1, detected by thin layer chromatography, and the same components were combined and the solvent was recovered under reduced pressure to obtain a crude benzaldehyde compound;

[0057] 3) The crude benzaldehyde compound obtained in step 2) was mixed with silica gel and loaded into a column, eluted with dichloromethane-methanol in a volume ratio of 30:1, and detected by thin layer chromatography. The same components were combined and the solvent was recovered under reduced pressure to obtain 11 components, which were marked as components Fr.1-11 in order from small to large polarity;

[0058] Dissolve component Fr.1 with methanol, mix the sample with silica gel and load it onto a flash column, and use a dichloromethane-methanol gradient elution with a volume ratio of 100:1, 90:1, 80:1, 70:1, 60:1, 50:1, 40:1, 30:1, 20:1, and 10:1, and perform thin layer chromatography detection. Combine the same components and recover the solvent under reduced pressure to obtain 8 components, which are labeled as components Fr.1-1 to Fr.1-8 in order of polarity from small to large.

[0059] Dissolve the components Fr.1-4 in methanol, purify them with a Sephadex LH-20 gel chromatography column, elute with methanol, and detect them with thin layer chromatography. Combine the same components and recover the solvent under reduced pressure to obtain three components, which are labeled as components Fr.1-4-1 to Fr.1-4-3 in descending order according to their molecular weights.

[0060] The component Fr.1-4-3 was dissolved in methanol, mixed with silica gel, and then placed on a vacuum column. It was eluted with dichloromethane-methanol in a volume ratio of 100:1, and detected by thin layer chromatography. The same components were combined and the solvent was recovered under reduced pressure to obtain pure benzaldehyde compounds. HPLC analysis showed a purity of 96% at absorption at 254nm and 230nm.

[0061] The pure benzaldehyde compound 3,5-dimethoxy-4-hydroxybenzaldehyde prepared above is in the form of a colorless and odorless oil with a yield of 0.001%.

[0062] The structure of the pure 3,5-dimethoxy-4-hydroxybenzaldehyde prepared above was identified using a variety of spectroscopic techniques, as follows:

[0063] Instruments and materials: UV was measured on a UV-210A spectrometer; 1H, 13C NMR spectra were measured on a Brukeram-500 MHz nuclear magnetic resonance spectrometer. TMS was used as an internal standard. Figure 3 and Figure 4 The experimental results are as follows:

[0064] 1H-NMR (CD3OD, 500 MHz) δ: 9.75 (1H, s, CHO), 7.23 (2H, s, H-2, 6), 4.87 (6H, s, OCH3-3, 5), 13C-NMR (125 MHz, CD3OD) δ: 192.92(CHO), 149.63 (C-3,5), 143.75 (C-4), 129.22 (C-1), 108.28 (C-2, 6), 56.84 (3, 5-OCH3).

[0065] Inspection: TLC, fluorescence at UV 254nm; sulfuric acid colorimetric agent, 110°C for 5 minutes, yellow color.

Claims

1. A method for extracting iridoid glycosides or benzaldehyde compounds from plants, characterized in that: The following steps are involved: 1) Using dried Patrinia dahurica as raw material, crushing and then extracting with ethanol to obtain an extract, and recovering the solvent under reduced pressure to obtain an extract concentrate; dissolving the extract concentrate with methanol, mixing the sample into a macroporous resin column, loading the column, and gradient eluting with water, 20% ethanol, 40% ethanol, 60% ethanol, 80% ethanol and 95% ethanol in sequence, collecting the 40% ethanol elution part, and recovering the solvent after decompression concentration to obtain a 40% ethanol extract; 2) Dissolve the 40% ethanol extract with methanol and mix the sample into silica gel. Load the sample onto a silica gel column and elute with dichloromethane-methanol in a volume ratio of 10:

1. Perform thin layer chromatography detection, combine the same components and recover the solvent under reduced pressure to obtain a crude product of iridoid glycosides. In step 2), the crude product of the iridoid glycosides was dissolved in methanol and then mixed into silica gel. After loading onto a silica gel column, the column was eluted with a gradient of dichloromethane-methanol at a volume ratio of 30:1, 20:1, 10:1, 5:1, 3:1, and 1:

1. The components were combined by thin layer chromatography to obtain 10 components, which were marked as components Fr. 1 to 10 in order of polarity from small to large. Component Fr.5 was dissolved in methanol and mixed into silica gel. After loading onto a silica gel column, it was eluted with dichloromethane-methanol in a volume ratio of 10:

1. Thin layer chromatography was performed. The same components were combined and the solvent was recovered under reduced pressure to obtain 6 components, which were labeled as components Fr.5-1 to Fr.5-6 in order of polarity from small to large. The component Fr.5-3 was dissolved in methanol, purified by Sephadex LH-20 gel chromatography column, eluted with methanol, detected by thin layer chromatography, and the same components were combined and the solvent was recovered under reduced pressure to obtain 3 components, which were labeled as components Fr.5-3-1 to Fr.5-3-3 in descending order according to the molecular weight of the obtained components; The component Fr. 5-3-2 was dissolved in methanol, silica gel was mixed and loaded into a column, and then eluted with dichloromethane-methanol in a volume ratio of 25:1, and detected by thin layer chromatography. The same components were combined and the solvent was recovered under reduced pressure to obtain Fr.5-3-2-1; Fr. 5-3-2-1 was dissolved in methanol, purified by Sephadex LH-20 gel chromatography column, eluted with methanol, detected by thin layer chromatography, and the same components were combined and the solvent was recovered under reduced pressure to obtain Fr. 5-3-2-1-1; Fr. 5-3-2-1-1 was separated and purified by semi-preparative high performance liquid phase separation, eluted with 52% methanol-water, and the pure product of cyclopentadiene ether terpene glycoside compound 2-O- p -Coumaroyl-loganin, the structural formula is as follows: ； or, 1) Using dried Patrinia punctata as raw material, crushing it and then extracting it with ethanol to obtain an extract, and recovering the solvent under reduced pressure to obtain an extract concentrate; dissolving the extract concentrate with methanol aqueous solution, loading it onto a macroporous resin column, and eluting it with 20% ethanol, 40% ethanol, 60% ethanol and 95% ethanol in a gradient manner in sequence, and collecting the 40% ethanol elution portion; 2) Dissolve the 40% ethanol elution portion with methanol and mix the sample into silica gel, elute with dichloromethane-methanol in a volume ratio of 30:1, detect with thin layer chromatography, combine the same components and recover the solvent under reduced pressure to obtain a crude benzaldehyde compound; In step 2), the obtained crude benzaldehyde compound was mixed with silica gel and loaded on a column, eluted with dichloromethane-methanol in a volume ratio of 30:1, and detected by thin layer chromatography. The same components were combined and the solvent was recovered under reduced pressure to obtain 11 components, which were marked as components Fr.1-11 in order from small to large polarity; Dissolve component Fr.1 in methanol, mix the sample with silica gel and load it onto a flash column, elute with a gradient of dichloromethane-methanol in a volume ratio of 100:1 to 10:1, and perform thin layer chromatography detection. Combine the same components and recover the solvent under reduced pressure to obtain 8 components, which are labeled as components Fr.1-1 to Fr.1-8 in order of polarity from small to large. Dissolve the components Fr.1-4 in methanol, purify them with a Sephadex LH-20 gel chromatography column, elute with methanol, and detect them with thin layer chromatography. Combine the same components and recover the solvent under reduced pressure to obtain three components, which are labeled as components Fr.1-4-1 to Fr.1-4-3 in descending order according to their molecular weights. Dissolve component Fr.1-4-3 in methanol, mix the sample with silica gel, put it on a vacuum column, elute with dichloromethane-methanol in a volume ratio of 100:1, detect by thin layer chromatography, combine the same components and recover the solvent under reduced pressure to obtain the pure benzaldehyde compound 3,5-dimethoxy-4-hydroxybenzaldehyde, chemical name syringaldehyde.

2. The method for extracting iridoid glycosides or benzaldehyde compounds from plants according to claim 1, characterized in that: In step 1), after crushing, the mixture is extracted with ethanol at 20-55° C. for 2-4 times, the extracts are combined, and the solvent is recovered under reduced pressure to obtain an extract concentrate.

3. The method for extracting iridoid glycosides or benzaldehyde compounds from plants as claimed in claim 2, characterized in that: In step 1), the volume concentration of ethanol is 70±10%.

4. The method for extracting iridoid glycosides or benzaldehyde compounds from plants according to claim 1, characterized in that: In step 2), the 40% ethanol extract or the 40% ethanol elution portion is mixed with 300-400 mesh silica gel at a weight ratio of 1:3-5 and then loaded into the column.

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