CN113087758B - Derivatives of carbocylic compounds derived from turnip and application thereof - Google Patents
Derivatives of carbocylic compounds derived from turnip and application thereof Download PDFInfo
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Abstract
The invention relates to the technical field of carbocyclic compounds derived from natural plants, in particular to a carbocylic compound derivative derived from turnip and application thereof, wherein the derivative has a structural formula shown in a formula (1) of the application, and the preparation process mainly comprises the following steps: the method comprises the steps of decocting, concentrating and drying the turnip to obtain a turnip dry paste, extracting the turnip dry paste with alcohol, extracting with ethyl acetate and ethyl acetate-methanol mixed solution, performing silica gel column chromatographic separation and semi-preparative liquid chromatographic separation to obtain a carbocylic compound from the turnip, and reacting the carbocylic compound with 3-bromomethyl-oxetane to obtain the derivative.
Description
Technical Field
The invention relates to the technical field of re-development and utilization of carbocyclic compounds derived from natural plants, in particular to derivatives of carbocyclic compounds derived from turnip and application thereof.
Background
The Brassica napus is dry root tuber and seed of Brassica napus (Brassica rapa L.) belonging to Brassica of Brassicaceae, collected in autumn when the root tuber and seed are mature, has sweet taste and warm nature, and has effects of dispelling pathogenic wind, generating red bar, nourishing, removing toxic substance, and treating bacon disease, dragon disease, asthenia and poisoning. The Tibetan medicine is named as "Niuma" (a four-part medical dictionary), and the Tibetan medicine is commonly named as "turnip" and "round root" (or "yuankanin" and "Yuan root"). In the Uygur family, Brassica is also known as "Brassica", and refers only to the root tuber of the plant Brassica rapa. Turnip in Tibetan and Uygur has a long history of homology of medicine and food, and Uygur doctors think that turnip is sweet, pungent and bitter in taste and warm in nature, has the effects of opening the chest and guiding qi downward, invigorating stomach and helping digestion and detoxifying, and is used for diseases such as chest distress, abdominal distention and pain, inappetence, sore and furuncle and pyogenic infections. In the Tibetan, the four medical classics: to relieve various toxicosis. "eight branches": for 'bacon' and 'dragon' diseases, generating 'Chiba'. "New compiled Tibetan medicine": it can be used for treating various toxicities and various toxicities. Modern medical research also shows that the turnip has the effects of resisting anoxia, aging and tumors, improving immunity and the like.
At present, the medicinal mode of the turnip is mainly to prepare turnip extract by a decoction method and then use the turnip extract to mix with other medicinal materials for preparing the medicine. For example, the Tibetan medicine Renzi Qingchangxi is prepared by using the Brassica napus extract. However, the turnip extract extracted in the prior art is troublesome to store, easy to breed microorganisms, easy to deteriorate, not beneficial to storage and transportation and control of dosage, and the stability and effectiveness of the medicine need to be improved. Therefore, how to improve the stability and effectiveness of the rutabaga medicament and make the product convenient for storage and transportation is a technical problem to be solved at present. In addition, the extractum medicinal mode of the rutabaga is rough at present, and the development of the rutabaga extract and derivatives thereof is necessary to achieve a more accurate and efficient medicinal mode.
The above background disclosure is intended to aid in understanding the inventive concepts and aspects of the invention, and is not necessarily prior art to the present application, and should not be used to assess novelty or inventiveness of the present application without providing explicit evidence that the above disclosure is made at the filing date of the present application.
Disclosure of Invention
Technical problem to be solved
The application provides a carbocycle compound derivative derived from turnip, which has the advantages of simple preparation method, easily controlled process, high yield and excellent effect of inhibiting the activity of pancreatic lipase, thereby achieving the purpose of losing weight without dieting.
The application also provides application of the derivatives of the carbocylic compound derived from the turnip in preparing anti-pulmonary fibrosis preparations, wherein the derivatives have excellent anti-pulmonary fibrosis effect, can reduce the degree of pulmonary fibrosis induced by BLM, and expand the medical application value of the carbocylic compound derived from the turnip and the derivatives thereof.
The invention aims to solve the problems that the prior-stage extract is inconvenient to transport and store, is easy to breed microorganisms, is difficult to accurately control the dosage, has low standardization level, seriously restricts the modernization construction of Tibetan medicines and the like in the background art, can effectively solve the problems and improve the standardization level of the Tibetan medicines.
(II) technical scheme
In order to solve the above technical problems or achieve the above technical object, the present invention provides the following technical solutions.
A derivative of a carbocylic compound derived from Brassica napus, said derivative having the formula shown in formula (1):
pancreatic lipase is the most important enzyme for hydrolyzing dietary fat, the development of the pancreatic lipase is not only related to age, but also regulated by dietary structure, endocrine hormone and the like, the change of the expression of the pancreatic lipase is closely related to metabolic diseases such as obesity, and the regulation of the pancreatic lipase is probably the target for treating the metabolic diseases such as obesity. Through experimental research, the inventor of the application finds that the bioavailability of the derivatives of the carbocycle compound derived from the turnip, shown in the formula (1), is remarkably improved, the derivatives of the carbocycle compound derived from the turnip have an excellent effect of inhibiting the activity of pancreatic lipase, can further prevent lipolysis by inhibiting the activity of pancreatic lipase, further enables fat to be directly discharged out of a body through a digestive tract, and achieves the purpose of losing weight without dieting, so the derivatives of the carbocycle compound derived from the turnip can be applied to the aspects of pancreatic lipase activity inhibitors, weight-losing preparations and the like.
Use of a derivative of a carbocylic compound derived from Brassica napus represented by the aforementioned formula (1) comprising:
1) preparing a pancreatic lipase inhibitor as an active ingredient; and/or
2) Can be used as active ingredient for preparing weight reducing preparation.
The carbocylic compound derived from Brassica napus has a structural formula shown in formula (2):
the derivatives of carbocylic compounds derived from Brassica napus, represented by the formula (1), are prepared by the following method: sequentially adding a carbocycle compound derived from the turnip shown in the formula (2) and sodium bicarbonate into enough dimethyl sulfoxide, dropwise adding 3-bromomethyl-oxetane, stirring and reacting at room temperature for at least 24h, then adding enough water, extracting with ethyl acetate for at least 3 times, merging organic phases, concentrating under reduced pressure to obtain a crude product, and purifying by silica gel column chromatography to obtain the product.
The carbocylic compound derived from cyanine and 3-bromomethyl-oxetane have a weight ratio of 3: 1.3-1.7.
The addition amount of the sodium bicarbonate is 1/5-1/2 of the weight of the carbocylic compound derived from the turnip.
The dropping speed of the 3-bromomethyl-oxetane is 2-4 s/drop.
The stirring speed during the stirring reaction is 150-600 r/min.
The eluent for silica gel column chromatography was petroleum ether-ethyl acetate (volume ratio 9: 1).
The carbocylic compound derived from turnip shown in the formula (2) and 3-bromomethyl-oxetane are subjected to substitution reaction to obtain the derivative shown in the formula (1), the preparation method is simple, the reaction mechanism is clear, the reaction process is easy to control, the yield of the derivative shown in the formula (1) is higher, the bioavailability of the derivative is remarkably improved compared with that of the carbocylic compound derived from turnip shown in the formula (2), the derivative has an excellent effect of inhibiting the activity of pancreatic lipase, fat is prevented from being decomposed and digested by an organism and directly discharged out of the body through a digestive tract, and the purpose of losing weight without dieting is achieved.
The carbocylic compound derived from rutabaga represented by the formula (2) is prepared by the following method:
A. decocting radix Brassicae Rapae, concentrating, and drying to obtain dry extract; adding ethanol solution into the turnip dry extract, reflux-extracting, recovering the extract under reduced pressure until no alcohol smell exists, adding water for dilution, filtering, and concentrating the filtrate to obtain extract;
B. decolorizing the extract with petroleum ether, extracting the lower layer liquid with ethyl acetate, collecting the lower layer liquid to obtain crude extractive solution, concentrating under reduced pressure, and extracting with ethyl acetate-methanol mixed solvent to obtain extractive solution;
C. b, concentrating the extract liquor in the step B, removing the solvent, dissolving the extract liquor in methanol, performing silica gel column chromatographic separation, equivalently collecting 50 parts, detecting each fraction by TLC, and collecting spot components by taking 5% sulfuric acid-ethanol solution as a color developing agent;
D. mixing the spot components, performing liquid chromatography separation in the first half under the conditions of detection wavelength of 205nm and mobile phase of 90 vol% methanol-water, and lyophilizing.
In the step A, the material-to-liquid ratio of the turnip dry paste to the ethanol solution is 1: 15-20, and the volume fraction of the ethanol solution is 85-90 vol%.
In the step A, the ethanol solution contains 0.8-1.2 vol% of oxalic acid.
In the step A, the heating reflux extraction is to heat the extract to 40-60 ℃ for reflux extraction for 3 times, and each time lasts for 1-2 hours.
In step B, the volume ratio of ethyl acetate to methanol was 8: 2.
In the step C, the mesh number of the silica gel for mixing the sample is 60-80 meshes.
In the step C, an eluent for silica gel column chromatographic separation is dichloromethane-methanol-water, and the volume ratio is 20:1: 0.1-10: 1: 0.1.
Compared with the method for preparing the carbocyclic compound by directly extracting the brassica napus, the method for preparing the carbocyclic compound by using the brassica napus has the advantages that the yield of the target compound can be remarkably improved by carrying out alcohol extraction on the brassica napus after decocting, concentrating and drying the brassica napus medicinal material to obtain a dry paste of the brassica napus, the yield of the target compound can be improved to be more than 2.5mg/kg from less than 1mg/kg of the brassica napus medicinal material by doping a small amount of oxalic acid into an ethanol solution during the alcohol extraction, the impurity content is extremely low during the chromatographic separation in the later period, the purity of the target compound is higher, and the utilization degree of the brassica napus medicinal material is remarkably improved; the precursor state for preparing the target compound is the dry extract of the rutabaga, and the rutabaga is smaller in volume, easy to store and transport and lower in storage cost.
The turnip dry paste is prepared by the following steps:
1) decocting and filtering the turnip medicinal material with water to obtain a filtered liquid medicine;
2) stirring and concentrating the filtered liquid medicine to obtain an extract;
3) decocting and concentrating the extract, and controlling the decocting temperature according to the density change of the extract to obtain a dry extract semi-finished product;
4) and standing the semi-finished dry paste, taking out, and drying to obtain the turnip dry paste.
The step 1) for preparing the turnip dry paste specifically comprises the following steps:
adding the turnip medicinal material into water with the amount being 9-11 times of the medicinal material amount for first decoction and filtration to obtain residue I and liquid I;
adding the residue I into water 7-9 times the amount of the medicinal materials, and performing second decoction and filtration to obtain residue II and liquid medicine II;
wrapping the medicine residue II with a fine gauze bag and squeezing forcibly to obtain medicine residue III and medicine liquid III; the liquid medicine III is used separately;
mixing the liquid medicine I, the liquid medicine II and the liquid medicine III to obtain filtered liquid medicine.
Wherein the first decoction is carried out at the decoction temperature of 180 ℃ for 180-200 min, and the first decoction is stirred for 1-2 min at the speed of 60-180 r/min every 20 min.
Wherein the decocting temperature of the second decocting is 180 ℃, the decocting time is 110-130 min, and the stirring is carried out for 1-2 min at the speed of 60-180 r/min every 20 min.
The step 2) for preparing the turnip dry paste specifically comprises the following steps:
and (4) stirring, concentrating and filtering the liquid medicine until the density reaches 1.05-1.06 g/mL, and concentrating.
Wherein the temperature for stirring and concentration is 180 ℃, and the stirring is carried out for 1-2 min at the speed of 60-180 r/min every 10 min.
The step 3) for preparing the turnip dry paste specifically comprises the following steps:
decocting and concentrating the extract at a decoction temperature of 180-200 ℃, stirring, and detecting the density of the extract;
the decoction temperature is adjusted downwards according to the density change of the extract, and the method specifically comprises the following steps:
when the density of the extract is 1.05-1.13 g/mL, controlling the decoction temperature to be 180 ℃;
when the density of the extract is 1.14-1.39 g/mL, controlling the decoction temperature to be 140 ℃;
when the density of the extract reaches 1.40g/mL or more, controlling the decoction temperature to be 120 ℃;
when the extract has no steam, the decoction and the concentration are finished.
Wherein the temperature for decoction and concentration is 180 ℃, the stirring is carried out for 1-2 min at the speed of 60-180 r/min every 10-20 min, the stirring frequency is gradually accelerated along with the increase of the density of the extract, and the stirring is continuously carried out until the density of the extract reaches 1.14 g/mL.
In step 4) of the present application for preparing the rutabaga dry paste:
the standing time of the dry paste semi-finished product is 12 h;
the drying mode is electrothermal blowing drying or vacuum drying or natural drying in the shade.
Preferably, the drying temperature of the electric heating forced air drying is 60-80 ℃, and the drying time is 1-3 d.
Preferably, the drying temperature of the vacuum drying is 40-60 ℃, and the drying time is 3-12 h.
Preferably, the drying time of the natural drying in the shade is 3-15 d.
By applying the technical scheme, the turnip medicinal material is added with water for decoction and filtration to obtain filtered liquid medicine, the filtered liquid medicine is stirred and concentrated to obtain an extract, the extract is decocted and concentrated, the decocting temperature is controlled according to the density change of the extract until no steam emerges from the extract to obtain a semi-finished dry paste, the semi-finished dry paste is taken out after standing, and the dried semi-finished dry paste is dried to obtain the turnip dry paste. The turnip dry paste prepared by the invention can replace turnip extract for use, is convenient to store and transport, can accurately control the dosage, has a simple preparation method, is easy to popularize, and can improve the stability and effectiveness of the medicine. The turnip dry paste provided by the application can replace a turnip extract in the prior art or be mixed with other medicines for preparing medicines, for example, the turnip dry paste provided by the application can be used for preparing Tibetan medicine kernel constant sensation instead of the turnip extract. Therefore, the turnip dry paste of the application mainly has the following advantages;
storage advantages: the turnip dry paste can be stored conveniently to a great extent, the storage time is prolonged, the utilization rate of raw medicinal materials is improved, and the defects that the extract is troublesome to store, is easy to breed microorganisms, is easy to deteriorate and the like are avoided;
transportation advantages are as follows: the turnip dry paste is convenient to transport, the loss in the transport process is reduced, and meanwhile, the transport distance and the transport time can be increased on the premise of ensuring the quality of medicinal materials;
the medicine is accurate: the turnip dry paste can be accurately used according to a prescription, and various parameters such as the dosage, the medication concentration and the like can be accurately controlled, so that the uniform and stable quality of the medicine is ensured.
The advantages are beneficial to ensuring the stability and effectiveness of Tibetan medicine medicinal materials, improving the product quality, ensuring the uniform and stable medicine quality, and the preparation method of the rutabaga dry paste provided by the application is simple and easy to popularize.
The use of the cyanine-derived carbocyclic compound derivative of the formula (1) as described above further includes:
3) can be used as active ingredient for preparing anti-pulmonary fibrosis preparation.
The use further comprises reducing ALB, ALP or LDH content in alveolar lavage fluid.
The use further comprises reducing glutathione content in lung tissue.
The inventor of the application discovers that the carbocylic compound derived from the turnip and the derivative thereof have therapeutic value on Bleomycin (BLM) induced pulmonary fibrosis (rat model) and can reduce the degree of the BLM induced pulmonary fibrosis, thereby further expanding the medical application value of the carbocylic compound derived from the turnip and the derivative thereof, namely preparing the anti-pulmonary fibrosis preparation by using the carbocylic compound as an active ingredient.
The above-described preferred conditions may be combined with each other to obtain a specific embodiment, in accordance with common knowledge in the art.
The raw materials or reagents involved in the invention are all common commercial products, and the operations involved are all routine operations in the field unless otherwise specified.
(III) advantageous effects
The technical scheme of the invention has the following advantages:
1) the bioavailability of the derivatives of the carbocycle compound derived from the turnip, which are shown in the formula (1), is remarkably improved, the derivatives of the carbocycle compound derived from the turnip have an excellent effect of inhibiting the activity of pancreatic lipase, can further prevent lipolysis by inhibiting the activity of the pancreatic lipase, further enable fat to be directly discharged out of a body through a digestive tract, and achieve the purpose of losing weight without dieting, so that the derivatives can be applied to the aspects of pancreatic lipase activity inhibitors, weight-losing preparations and the like;
2) the preparation method of the derivatives of the carbocylic compound derived from the turnip shown in the formula (1) is simple, the process is easy to control, the yield of the derivatives is high, and the bioavailability of the derivatives is remarkably improved compared with that of the carbocylic compound derived from the turnip shown in the formula (2); when the carbocycle compound derived from the turnip shown in the formula (2) is prepared, the turnip medicinal material is decocted, concentrated and dried to obtain a turnip dry paste, and then alcohol extraction is carried out, so that the yield of the target compound can be remarkably improved, the yield of the target compound can be improved to be more than 2.5mg/kg from less than 1mg/kg of the turnip medicinal material, and the deep utilization degree of the turnip is remarkably improved;
3) when the medicinal effectiveness and safety of the cynanchum plaster are researched, the carbocylic compound derived from the cynanchum and the derivatives thereof have therapeutic value on Bleomycin (BLM) -induced pulmonary fibrosis (rat model), and the degree of BLM-induced pulmonary fibrosis can be reduced, so that the medical application value of the carbocylic compound derived from the cynanchum and the derivatives thereof is further expanded, namely the carbocylic compound derived from the cynanchum and the derivatives thereof can be used as active ingredients to prepare anti-pulmonary fibrosis preparations;
4) the turnip medicinal material is decocted and filtered to obtain filtered liquid medicine, the filtered liquid medicine is stirred and concentrated to obtain extract, the extract is decocted and concentrated to obtain a semi-finished dry paste, and the semi-finished dry paste is dried to obtain the turnip dry paste.
The invention adopts the technical scheme for realizing the purpose, makes up the defects of the prior art, and has reasonable design and convenient operation.
Drawings
These and/or other objects, features, advantages and embodiments of the present invention will become more apparent from the following detailed description of the invention when taken in conjunction with the accompanying drawings in which:
FIG. 1 is a schematic structural diagram of a cyanine-derived carbocyclic compound derivative of the present invention;
FIG. 2 is a schematic structural representation of a carbocylic compound derived from Brassica napus according to the present invention;
FIG. 3 is a flow chart of the process for preparing an extract according to example 1 of the present invention;
FIG. 4 is a flow chart of a process for preparing a dry paste proposed in example 1 of the present invention;
FIG. 5 is a graph of the density of the extract according to the invention in example 1 as a function of temperature;
FIG. 6 is a hydrogen spectrum of a carbocylic compound derived from Brassica napus prepared in example 2 of the present invention;
FIGS. 7 and 8 are statistical graphs of yields of carbocylic compounds derived from Brassica napus according to embodiments of the present invention;
FIG. 9 is a graph showing the inhibition rate of orlistat on pancreatic lipase in the experimental examples of the present invention;
FIG. 10 is a graph showing the inhibition of pancreatic lipase by derivatives of Brassica napus-derived carbocyclic compounds in accordance with the present invention;
FIG. 11 is a graph showing Glutathione (GSH) content in rat lung tissue in an animal model according to an experimental example of the present invention.
Detailed Description
Unless otherwise indicated, all amounts, ratios, and parts recited herein are by weight, with the exception that "mol%" is a mole percentage and "vol%" is a volume percentage.
The following describes in detail specific embodiments of the present invention. It should be understood that the detailed description and specific examples, while indicating the present invention, are intended for purposes of illustration and explanation only and are not intended to limit the scope of the invention.
The present invention is described in detail below.
Example 1: a dried turnip paste:
as shown in fig. 3 and 4, this example prepared a turnip dry paste by the following steps:
1) cleaning 6.6kg of turnip medicinal material, slicing, air drying and other pretreatment, adding 63.58L of water into a 500L jacketed kettle, carrying out first decoction, wherein the decoction temperature is 180 ℃, the decoction time is 190min, stirring at 120r/min every 20min for 1min, and filtering with a 100-mesh sieve to obtain medicine residue I and medicine liquid I; adding 57.4L water into the residue I, decocting at 180 deg.C for 120min in a jacketed kettle of 500L volume, and stirring at 120r/min for 1min every 20 min; filtering with a 100-mesh sieve to obtain medicine residue II and medicine liquid II; wrapping the residue II with a fine gauze bag, and squeezing to obtain residue III and medicinal liquid III, wherein the residue III is used separately; mixing the liquid medicine I, the liquid medicine II and the liquid medicine III to obtain filtered liquid medicine;
2) adding the filtered liquid medicine into a 300L jacketed kettle for concentration, wherein the concentration temperature is 180 ℃, stirring for 1min at 120r/min every 10min, and when the density of the filtered liquid medicine is measured to reach 1.06g/mL, completing concentration to obtain an extract;
3) decocting and concentrating the extract in 300L jacketed kettle at 180 deg.C for 2min at 120r/min every 20min, detecting, and adjusting the decocting temperature according to the density change of the extract, wherein the density and temperature control table of the extract is shown in Table 1, and the temperature-dependent density curve of the extract is shown in FIG. 5;
TABLE 1 relationship between extract density and temperature
| Temperature (. degree.C.) | 180 | 140 | 120 |
| Density (g/mL) | 1.06 | 1.14 | 1.40 |
In particular, the method comprises the following steps of,
when the density of the extract reaches 1.06g/mL, controlling the decoction temperature to be 180 ℃;
when the density of the extract reaches 1.14g/mL, controlling the decoction temperature to be 140 ℃;
when the density of the extract reaches 1.40g/mL, controlling the decoction temperature to be 120 ℃;
when the extract has no steam, the decoction and the concentration are finished;
the higher the density of the extract is, the faster the stirring frequency is, the stirring frequency can be properly adjusted according to the density, when the density of the extract reaches 1.14g/mL, the stirring frequency is continuous stirring, and when no steam emerges from the extract, the decoction and concentration are completed to obtain a semi-finished product of dry extract; it should be noted that the density and temperature control table of the extract is a preferred embodiment of the present application, and can be adjusted according to specific implementation scenarios, and other ways of adjusting the decocting temperature according to the density change of the extract all belong to the protection scope of the present application;
4) standing the semi-finished product of the dry paste for 12h, taking out, drying by electric heating forced air, drying at 80 deg.C for 2d, and collecting the paste after drying to obtain the Brassica napus dry paste.
The Brassica napus dry extract provided by the preferred embodiment can be used for replacing a Brassica napus extract in the prior art or being mixed with other medicines for preparing medicines, for example, the Brassica napus dry extract provided by the application is used for preparing the Tibetan medicine Renqing juxie instead of the Brassica napus extract. It mainly has the following advantages;
storage advantages: the turnip dry paste can be stored conveniently to a great extent, the storage time is prolonged, and the utilization rate of the raw medicinal materials is improved. The defects of troublesome storage, easy breeding of microorganisms, easy deterioration and the like of the extractum are avoided.
Transportation advantages are as follows: the turnip dry paste can be conveniently transported, and the loss in the transportation process is reduced. Meanwhile, the transportation distance and the transportation time can be increased on the premise of ensuring the quality of the medicinal materials.
The medicine is accurate: the turnip dry paste can be accurately taken according to a prescription, and various parameters such as the dosage, the medication concentration and the like can be accurately controlled, so that the uniformity and the stability of the quality of the medicine are ensured.
The advantages are beneficial to ensuring the stability and effectiveness of Tibetan medicine medicinal materials, improving the product quality, ensuring the uniform and stable medicine quality, and the preparation method of the rutabaga dry paste provided by the application is simple and easy to popularize.
Example 2: carbocyclic compounds derived from rutabaga:
this example, starting from the dry extract of rutabaga obtained in example 1, prepares a carbocyclic compound derived from rutabaga of formula (2) by the following specific steps:
A. taking the dry paste of the turnip in the example 1, adding 88 vol% ethanol solution with the weight being 16 times that of the dry paste, wherein the ethanol solution contains 1.0 vol% oxalic acid, heating to 50 ℃, carrying out reflux extraction for 3 times, each time for 1.5h, combining the extracting solutions, recovering the ethanol solution under reduced pressure until no alcohol smell exists, adding water for dilution, filtering by medium-speed filter paper, and concentrating the filtrate to 1/10 volumes at 50 ℃ to obtain an extract;
B. decolorizing the extract with petroleum ether for 2 times, extracting the lower layer liquid with ethyl acetate for 2 times, collecting the lower layer liquid to obtain crude extractive solution, concentrating under reduced pressure, and extracting with ethyl acetate-methanol mixed solvent (volume ratio of 8:2) to obtain extractive solution;
C. concentrating at 50 ℃ until the dry paste is subjected to solvent removal, dissolving the dry paste with methanol, performing 80-mesh silica gel column chromatographic separation, equivalently collecting 50 parts of eluent which is dichloromethane-methanol-water with the volume ratio of 20:1: 0.1-10: 1:0.1, detecting each fraction by TLC, and collecting spot components by taking 5% sulfuric acid-ethanol solution as a color developing agent;
D. mixing the spot components, performing liquid chromatography separation in the first half under the conditions of detection wavelength of 205nm and mobile phase of 90 vol% methanol-water, and lyophilizing. The hydrogen spectrum of the carbocylic compound derived from turnip is shown in FIG. 6, and the carbon spectrum data is shown in Table 2.
TABLE 2,13C NMR(CDCl3，150MHz)
| |
1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 |
| δ | 45.6 | 70.3 | 75.5 | 44.3 | 47.9 | 19.3 | 34.2 | 41.0 | 50.1 | 38.9 |
| C | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 |
| δ | 22.6 | 25.9 | 137.5 | 32.6 | 37.5 | 70.5 | 55.6 | 127.8 | 43.0 | 33.8 |
| C | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 |
| δ | 37.2 | 27.3 | 21.5 | 66.9 | 17.8 | 18.2 | 26.3 | 178.6 | 32.5 | 27.6 |
The carbocylic compound derived from the turnip belongs to white needle-shaped crystals, the Libermann Berchard and Molish are both positive, and the carbocylic compound is heated to 105 ℃ under a TLC thin layer chromatography 5% sulfuric acid-ethanol solution to be purple red, which indicates that the carbocylic compound is triterpenes. ESI-MS M/z 503.35[ M-H ]]-、527.35[M+Na]+Molecular weight 504, molecular formula C30O6H48And unsaturation 7. From1Signal delta in H-NMR spectrumH0.8 to 1.2 of which each represents 6 methyl groups, deltaH3.5-5.2 shows 5 continuous oxygen hydrogen signals. Bonding of13C NMR and DEPT 135 °, the 30 carbon signal of a carbocyclic compound contains 6 primary, 10 secondary, 5 tertiary and 9 quaternary carbons. DeltaC178.6 shows carbonyl, deltaC137.5, 127.8 show olefinic double bonds, while the hydrogen spectrum has no olefinic signals, indicating that the olefinic hydrogens are fully substituted.δ C70.3, 75.5, 70.5, 66.9 in low field shows oxygen linked carbon signal, which is presumed to be hydroxyl. The nuclear magnetic data is consistent with the research on two novel triterpene compounds in the turnip and the anticancer activity thereof (Dulin and the like, a pharmacology report), so the determined structure is shown as a formula (2).
Example 3: carbocyclic compounds derived from rutabaga:
this example, starting from the dry extract of rutabaga obtained in example 1, prepares a carbocylic compound derived from rutabaga represented by the formula (2) of the present application by the following specific steps:
A. taking the dry paste of the turnip in the example 1, adding 88 vol% ethanol solution with the weight being 16 times that of the dry paste, heating to 50 ℃, carrying out reflux extraction for 3 times, each time for 1.5h, combining the extracting solutions, decompressing, recovering until no alcohol smell exists, adding water for dilution, filtering by medium-speed filter paper, and concentrating the filtrate to 1/10 volume at 50 ℃ to obtain an extract;
B. the same procedure as in step B of example 2;
C. same as step C in example 2
D. Same as step D in example 2.
Example 4: carbocyclic compounds derived from rutabaga:
this example, starting from the dry extract of rutabaga obtained in example 1, prepares a carbocylic compound derived from rutabaga represented by the formula (2) of the present application by the following specific steps:
A. taking the dry paste of the turnip in the example 1, adding 88 vol% ethanol solution with the weight being 16 times that of the dry paste, wherein the ethanol solution contains 0.2 vol% oxalic acid, heating to 50 ℃, carrying out reflux extraction for 3 times, each time for 1.5h, combining the extracting solutions, recovering the ethanol solution under reduced pressure until no alcohol smell exists, adding water for dilution, filtering by medium-speed filter paper, and concentrating the filtrate to 1/10 volumes at 50 ℃ to obtain an extract;
B. the same procedure as in step B of example 2;
C. same as step C in example 2
D. Same as step D in example 2.
Example 5: carbocyclic compounds derived from rutabaga:
this example, starting from the dry extract of rutabaga obtained in example 1, prepares a carbocylic compound derived from rutabaga represented by the formula (2) of the present application by the following specific steps:
A. taking the dry paste of the turnip in the example 1, adding 88 vol% ethanol solution with the weight being 16 times that of the dry paste, wherein the ethanol solution contains 0.5 vol% oxalic acid, heating to 50 ℃, carrying out reflux extraction for 3 times, each time for 1.5h, combining the extracting solutions, recovering the ethanol solution under reduced pressure until no alcohol smell exists, adding water for dilution, filtering by medium-speed filter paper, and concentrating the filtrate to 1/10 volumes at 50 ℃ to obtain an extract;
B. the same procedure as in step B of example 2;
C. same as step C in example 2
D. Same as step D in example 2.
Example 6: carbocyclic compounds derived from rutabaga:
this example, starting from the dry extract of rutabaga obtained in example 1, prepares a carbocylic compound derived from rutabaga represented by the formula (2) of the present application by the following specific steps:
A. taking the dry paste of the turnip in the example 1, adding 88 vol% ethanol solution with the weight being 16 times that of the dry paste, wherein the ethanol solution contains 1.5 vol% oxalic acid, heating to 50 ℃, carrying out reflux extraction for 3 times, each time for 1.5h, combining the extracting solutions, recovering the ethanol solution under reduced pressure until no alcohol smell exists, adding water for dilution, filtering by medium-speed filter paper, and concentrating the filtrate to 1/10 volumes at 50 ℃ to obtain an extract;
B. the same procedure as in step B of example 2;
C. same as step C in example 2
D. Same as step D in example 2.
Example 7: carbocyclic compounds derived from rutabaga:
this example, starting from the dry extract of rutabaga obtained in example 1, prepares a carbocylic compound derived from rutabaga represented by the formula (2) of the present application by the following specific steps:
A. taking the dry paste of the turnip in the example 1, adding 88 vol% ethanol solution with the weight being 16 times that of the dry paste, wherein the ethanol solution contains 2.0 vol% oxalic acid, heating to 50 ℃, carrying out reflux extraction for 3 times, each time for 1.5h, combining the extracting solutions, recovering the ethanol solution under reduced pressure until no alcohol smell exists, adding water for dilution, filtering by medium-speed filter paper, and concentrating the filtrate to 1/10 volumes at 50 ℃ to obtain an extract;
B. the same procedure as in step B of example 2;
C. same as step C in example 2
D. Same as step D in example 2.
Example 8: carbocyclic compounds derived from rutabaga:
in this example, a carbocylic compound derived from Brassica napus, represented by formula (2) of the present application, is prepared from Brassica napus, and includes the following specific steps:
A. taking the same batch of turnip medicinal materials as in example 1, carrying out pretreatment such as cleaning, slicing, airing and the like as in example 1, then adding 88 vol% ethanol solution with the weight being 16 times that of the turnip medicinal materials, heating the ethanol solution to 50 ℃ to carry out reflux extraction for 3 times, wherein the ethanol solution contains 1.0 vol% oxalic acid, carrying out 1.5h each time, combining extracting solutions, carrying out reduced pressure recovery until no alcohol smell exists, adding water to dilute, filtering through medium-speed filter paper, and concentrating the filtrate to 1/10 volume at 50 ℃ to obtain an extract;
B. same as step B in example 2;
C. same as step C in example 2
D. Same as step D in example 2.
Example 9: carbocyclic compounds derived from rutabaga:
in this example, a carbocylic compound derived from turnip represented by formula (2) of the present application is prepared from turnip medicinal materials, and the specific steps include:
A. taking the same batch of turnip medicinal materials as in example 1, carrying out pretreatment such as cleaning, slicing, airing and the like as in example 1, then adding 88 vol% ethanol solution with the weight being 16 times that of the turnip medicinal materials, heating the ethanol solution to 50 ℃ to carry out reflux extraction for 3 times, wherein the ethanol solution contains 0.2 vol% oxalic acid, carrying out 1.5h each time, combining extracting solutions, carrying out reduced pressure recovery until no alcohol smell exists, adding water to dilute, filtering through medium-speed filter paper, and concentrating the filtrate to 1/10 volume at 50 ℃ to obtain an extract;
B. the same procedure as in step B of example 2;
C. same as step C in example 2
D. Same as step D in example 2.
Experimental example 1: detection of yield of carbocyclic compound derived from Brassica napus:
quantitative statistics is respectively carried out on the carbocycle compounds derived from the rutabaga obtained in each technical scheme in the embodiments 2-9, and the statistical results are shown in fig. 7 according to the statistics of the yield of the carbocycle compounds relative to the rutabaga medicinal material. As can be seen from fig. 7, compared with the method for directly preparing the target carbocyclic compound from the rutabaga medicinal material, in the preferred embodiment 2 of the present application, the yield of the target carbocyclic compound prepared from the rutabaga dry extract can be significantly increased, and in the comparative examples 2 to 7 and the comparative examples 2 and 8 to 9, no matter from the rutabaga medicinal material or the rutabaga dry extract, the addition of an appropriate amount of oxalic acid into the ethanol solution for preparing the target carbocyclic compound by extracting the rutabaga or the dry extract facilitates the increase of the yield of the target carbocyclic compound from less than 1mg/kg of the rutabaga medicinal material to more than 2.5mg/kg, thereby significantly increasing the utilization degree of the deep layer of the rutabaga. Based on example 2, the dry paste of rutabaga obtained in the same batch of example 1 is used as a raw material, only the oxalic acid content in the ethanol solution during the alcohol extraction is changed to obtain a series of target carbocyclic compounds, and the statistical yield is shown in fig. 8, which indicates that when the oxalic acid content is between 0.8 to 1.2 vol%, the yield of the compounds is not lower than 2.5mg/kg, which indicates that the yield of the target compounds can be increased from less than 1mg/kg of the rutabaga medicinal material to more than 2.5mg/kg by extracting the rutabaga in the form of dry paste and adding a certain amount of oxalic acid into the alcohol solution during the alcohol extraction, thereby significantly increasing the deep utilization degree of the rutabaga.
Example 10: derivatives of carbocylic compounds derived from turnip:
this example further prepares derivatives from the carbocyclic compounds obtained in example 2, including: 1g of the carbocylic compound derived from turnip obtained in example 2 and 0.3g of sodium bicarbonate are sequentially added into 15mL of dimethyl sulfoxide, 0.5g of 3-bromomethyl-oxetane is dropwise added at the speed of 2 s/drop, the mixture is stirred at room temperature for 24 hours at 300r/min, then 20mL of water is added, extraction is carried out for 3 times by ethyl acetate, the organic phases are combined and then concentrated under reduced pressure to obtain a crude product, petroleum ether-ethyl acetate (volume ratio 9:1) is used as an eluent, the crude product is purified by silica gel column chromatography and dried at 50 ℃ to constant weight to obtain 825.7mg of white powder, and the yield is about 72%. HR-EI-MS m/z 574.39 was detected to infer that molecular weight 574 increased 4 carbon signals relative to carbocyclic compounds and that 3-bromomethyl-oxetane reacted with the carboxyl group of carbocyclic compounds in a substitution reaction of formula C34O7H54The structural formula is shown as formula (1).
Experimental example 2: inhibition of pancreatic lipase activity:
this experimental example was conducted to examine the inhibitory effect of a cyanine-derived carbocyclic compound derivative described in formula (1) of the present application on pancreatic lipase activity, and the specific procedures were as follows:
1) adding 1.36g of potassium dihydrogen phosphate into 79mL of 0.1mol/L sodium hydroxide solution, adding water to dilute to 200mL after dissolution to obtain Phosphate Buffer Solution (PBS), dissolving by using the PBS and preparing 5mmol/L p-nitrophenol mother solution, diluting to obtain 0.050mmol/L, 0.075mmol/L, 0.100mmol/L, 0.150mmol/L and 0.200mmol/L diluent, respectively taking 200 mu L of p-nitrophenol solution with each concentration into a 96-well plate, measuring absorbance under 405nm by using a microplate reader, and drawing a standard curve by using the concentration of the p-nitrophenol solution as a horizontal coordinate and the absorbance as a vertical coordinate to obtain an equation: 3.26885X +0.02532, R2＝0.9995；
2) Dissolving a derivative of the carbocycle compound derived from the turnip shown in the formula (1) by using a small amount of dimethyl sulfoxide, adding PBS (phosphate buffer solution) for ultrasonic dissolution, and preparing derivative solutions with the mass concentrations of 0.05mg/L, 0.25mg/L, 0.50mg/L, 1.00mg/L and 1.50mg/L respectively, wherein the content of the dimethyl sulfoxide is not higher than 1%;
3) dissolving orlistat in a small amount of dimethyl sulfoxide, adding PBS (phosphate buffer solution) for ultrasonic dissolution, and preparing orlistat solutions with mass concentrations of 0.03mg/L, 0.06mg/L, 0.12mg/L, 0.18mg/L and 0.24mg/L respectively, wherein the content of the dimethyl sulfoxide is not higher than 1%;
4) dissolving 50mg of pig pancreatic lipase by PBS, fixing the volume to 50mL, centrifuging at 10000r/min for 5min, taking supernatant and diluting to obtain pancreatic lipase solution of 0.25 mg/mL;
5) weighing 5 mu mol of p-nitrophenylpalmitate, fully dissolving the p-nitrophenylpalmitate in 400 mu L of isopropanol, heating to 45 ℃ to fully dissolve the p-nitrophenylpalmitate, and then diluting the p-nitrophenylpalmitate with PBS to 0.5mmol/L substrate solution;
6) adding PBS, a derivative solution and a pancreatic lipase solution into a 96-well plate, wherein the adding amount is shown in the table 3, incubating for 10min at 37 ℃, adding a substrate solution to start reaction, incubating for 30min at 37 ℃, then measuring the absorbance at 405nm by using an enzyme-labeling instrument, reducing the pancreatic lipase activity reacting with orlistat or the derivative, reducing the yield of p-nitrophenol and the absorbance, and obtaining the inhibition rate of the inhibitor substance on the pancreatic lipase by contrasting with a p-nitrophenol standard curve, wherein the formula is shown as the formula (3):
in the formula (3), A1Is the absorbance of the control experiment, A0Is the absorbance of a control blank, B1Is the absorbance of the sample test group, B0Is the absorbance of the sample blank.
TABLE 3 addition of reactants in the reaction System
Statistical results show that orlistat and a derivative of a carbocylic compound derived from Brassica napus represented by formula (1) of the present application inhibit pancreatic lipase as shown in FIGS. 9 and 10, respectively, and it can be seen from a combination of FIGS. 9 and 10 that a derivative of a carbocylic compound derived from Brassica napus represented by formula (1) of the present application has excellent inhibitory activity on pancreatic lipase, and the inhibitory activity shows a positive correlation with concentration, and it can be seen that an IC of pancreatic lipase is determined from the derivative of a carbocylic compound derived from Brassica napus represented by formula (1) of the present application50About 0.8mg/L, and therefore, a pancreatic lipase inhibitor and/or a slimming agent can be produced based on it as an active ingredient.
Experimental example 3: anti-pulmonary fibrosis effect:
this experimental example was conducted to examine the effect of Bleomycin (BLM) -induced pulmonary fibrosis of a derivative of a carbocylic compound derived from rutabaga as described in formula (1) of the present application, according to the prior art, and the specific procedures were as follows:
1) animal model: male SPF-grade SD rats 50 with a body mass of about 220g were randomly divided into five groups: a control group, a model group, a positive drug group (50mg/kg of pirfenidone), a derivative high dose group (50mg/kg) and a derivative low dose group (25mg/kg), wherein each group comprises 10 drugs;
2) molding: injecting chloral hydrate into abdominal cavity of all rats at 400mg/kg for anesthesia, fixing in supine position, performing oral intubation through trachea, injecting 0.2mL of normal saline into control group through intubation, injecting 0.2mL of bleomycin into the rest rats through intubation at 5mg/kg of dosage, erecting and rotating the rats to uniformly distribute the medicine in lung; the medicine is taken on the third day after operation, and the positive medicine group, the derivative high-dose group and the derivative low-dose group are correspondingly taken until the time reaches 21 days;
3) item measurement: after the last administration, 360mg/kg chloral hydrate is injected into the abdominal cavity for anesthesia, organs are separated after neck twisting sacrifice, and the indexes of each item are determined according to the following list:
3.1, lung coefficient: separating lung, weighing wet lung weight (mg), measuring tibia length (mm), and calculating lung coefficient according to wet lung weight/tibia length;
3.2, wet/dry mass ratio of lung tissue: taking left lung tissue, sucking dry surface liquid by filter paper, and weighing to obtain wet weight W; placing the mixture in an oven at 80 ℃ to dry until the mass is constant, weighing the mixture to obtain a dry weight D, and calculating a W/D ratio;
3.3, oxygen partial pressure: after the last administration, blood is taken from the aorta of the abdominal cavity for blood gas analysis, and the oxygen partial pressure is measured;
3.4, relevant indices in bronchoalveolar lavage fluid (BALF): separating lung, irrigating lung with 37 deg.C sterile physiological saline, collecting BALF, centrifuging at 1500r/min for 10min, subpackaging, freezing at-80 deg.C, and determining Albumin (ALB), alkaline phosphatase (ALP), and Lactate Dehydrogenase (LDH) index content in BALF according to kit method;
3.5, content of Glutathione (GSH) in lung tissue: 0.1g of lung tissue is taken and added into 1mLNS for homogenization, the homogenate is centrifuged at 1500r/min for 10min, and then supernatant is taken, and the content of GSH is detected according to a kit method.
The measurement results of the items are shown in tables 4 to 5 and FIG. 11.
TABLE 4 Lung coefficient and oxygen partial pressure statistics
| Group of | Lung factor (mg/mm) | W/D | Oxygen partial pressure (kPa) |
| Control group | 54.4 | 5.2 | 15.3 |
| Model set | 73.6 | 7.1 | 10.9 |
| Positive drug group | 63.9 | 5.3 | 13.8 |
| High dose group of derivatives | 64.2 | 5.4 | 13.2 |
| Derivative low dose group | 69.8 | 6.5 | 11.8 |
As can be seen from Table 4, the lung coefficient and the wet/dry mass ratio of the lung tissue of the model group are higher than those of the control group, and the oxygen partial pressure is lower than that of the control group, which indicates that the molding is successful; when the positive drug group and the derivative group are compared, the effect of the derivative of the carbocylic compound derived from the rutabaga in the formula (1) on the lung coefficient and the oxygen partial pressure value are weaker than those of the positive drug, while the wet/dry mass ratio of the lung tissue of the derivative high-dose group is equal to that of the positive drug, and the derivative has a certain BLM-induced pulmonary fibrosis effect.
TABLE 5 ALB, ALP, LDH index content statistics
| Group of | ALB content (U/L) | ALP content (U/L) | LDH content (U/L) |
| Control group | 6.45 | 90.26 | 554.85 |
| Model set | 8.36 | 180.33 | 866.41 |
| Positive drug group | 6.60 | 118.45 | 559.53 |
| High dose group of derivatives | 6.71 | 122.52 | 576.31 |
| Derivative low dose group | 7.44 | 148.69 | 645.88 |
The pulmonary interstitial fibrosis is mainly caused by alveolitis in the early stage, the ALB, ALP and LDH content in BALF is obviously increased at the stage and participates in lung tissue repair and local immune epidemic prevention reaction together, so that the increase of the index content can indirectly reflect the damage degree of inflammation; during pulmonary interstitial fibrosis, pulmonary alveolar epithelial cells are damaged, so that pulmonary active oxygen is pathologically aggravated, and pulmonary interstitial fibrosis is aggravated through peroxidation damage, protein damage, cytokine network imbalance and other ways, GSH is an important antioxidant existing in pulmonary alveoli, and the damage of the pulmonary alveolar epithelial cells caused by the increase of the release amount of oxygen free radicals is aggravated due to the lack of local GSH in the lung. As can be seen from table 5, the BALF-related index of the model group showed a significantly increasing trend compared to the control group, indicating that BLM induces pulmonary fibrosis, while the positive drug group and the derivative group showed a significantly decreasing trend compared to the model group, indicating that both the positive drug and the derivative have the effect of inhibiting and/or repairing pulmonary fibrosis; specifically, as can be seen from fig. 11, the GSH content of the positive drug group and the derivative group is significantly reduced compared to the model group, and the foregoing reduction in the ALB, ALP, LDH and GSH content indicates that both the positive drug and the derivative described in the present application exert a positive effect on repairing pulmonary interstitial cellulose, indicating that the derivative of the carbocylic compound derived from rutabaga described in formula (1) in the present application has an excellent anti-Bleomycin (BLM) -induced pulmonary fibrosis effect.
Conventional techniques and schemes not described in detail in the above embodiments are well known in the art, and thus are not described in detail herein.
In addition, any combination of the various embodiments of the present invention is also possible, and the same should be considered as the disclosure of the present invention as long as it does not depart from the spirit of the present invention.
Claims (5)
1. A derivative of a carbocylic compound derived from Brassica napus, said derivative having the formula shown in formula (1):
2. the derivative according to claim 1, characterized in that it has the effect of inhibiting pancreatic lipase and of combating pulmonary fibrosis.
3. A process for the preparation of a derivative of a carbocylic compound derived from rutabaga as claimed in claim 1 or 2, characterized in that it comprises the following steps: sequentially adding a carbocycle compound derived from turnip shown in the formula (2) and sodium bicarbonate into enough dimethyl sulfoxide, dropwise adding 3-bromomethyl-oxetane, stirring and reacting at room temperature for at least 24 hours, then adding enough water, extracting with ethyl acetate for at least 3 times, merging organic phases, concentrating under reduced pressure to obtain a crude product, and purifying by silica gel column chromatography to obtain the compound;
4. the method of claim 3, wherein: the carbocylic compound derived from cyanine and 3-bromomethyl-oxetane have a weight ratio of 3: 1.3-1.7.
5. Use of a derivative of a carbocylic compound derived from Brassica napus according to claim 1 or 2, characterized in that it is:
preparing a pancreatic lipase inhibitor as an active ingredient;
preparing an anti-pulmonary fibrosis preparation as an active ingredient;
preparing an agent that reduces ALB, ALP or LDH content in alveolar lavage fluid; or
Preparing the preparation for reducing the content of the glutathione in the lung tissue.
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