Campestrisine (C25H31O4N3) and application thereof

Abstract

The invention discloses campestrisine (C25H31O4N3) and application thereof, belonging to the field of food, health products and medicines. According to the invention, campestrisine is extracted from rape pollen or rape bee pollen with an ethanol solution, and macroporous resin, MCI column chromatography and ODS-C18 reversed-phase column chromatography are employed for separation so as to obtain a pure campestrisine product. The compound, i.e., campestrisine, is determined to be C25H31O4N3 according to analysis results of mass spectra, 1HNMR spectra, 13CNMR spectra, DEPT-135 spectra, heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond coherence (HMBC) and has a structure as defined in the specification. A mouse model of prostatitis caused by carrageenan is used for in-vivo anti-prostatitis test, and test results show that campestrisine (C25H31O4N3) has inhibitory effect on prostatitis. Thus, campestrisine (C25H31O4N3) provided by the invention can be efficiently used for preparation of drugs capable of resisting prostatitis and used for food and health food.

Description

technical field

[0001] The invention relates to a kind of rape flower alkali and its application, belonging to the fields of food, health products and medicine. Background technique

[0002] Rapeseed pollen is pollen of oilseed rape (Brassica campestris L.), and rape bee pollen (beepollen) is pollen balls collected by bees from the anthers of rapeseed plants. Rapeseed pollen and rapeseed bee pollen have a variety of physiological functions, especially for benign prostatic hyperplasia and prostatitis. If its functional components can be extracted from rape pollen and its structure identified, it is hoped that it can be used to prepare drugs, or the substance can be synthesized by chemical methods to prepare drugs. However, the current chemical components in rape pollen and rape bee pollen In most of the reports, the crude extract with the above effects is obtained from rapeseed pollen, but it is still unclear what kind of substance is the functional ingredient that inhibits ...

Examples

Embodiment 1

[0020] Get 5kg rape bee pollen, pulverize, pass through a 40-mesh sieve, take the under-sieve powder, crush the over-sieve again through a 40-mesh sieve, take the under-sieve powder, place the under-sieve powder in a 50-liter extraction tank, add 40 1 liter of ethanol aqueous solution with a volume fraction of 80%, extracted at room temperature for 3 hours, filtered, took the filtrate, and repeated extraction of the filter residue twice to obtain 115 liters of filtrate, concentrated under reduced pressure to 6 liters, poured into the extraction tank, and added 6 liters of Degrease with n-hexane, stir at 60r / min for 40 minutes, let it stand for 5 hours, separate the n-hexane phase, repeat the degreasing once more, take the sample after the second degreasing, add 6 liters of deionized water, open the cover and stir at 50°C The residual normal hexane was volatilized in 40 minutes, and then passed through the macroporous resin column AB-8 (10×150cm) post, and was first eluted with ...

Embodiment 2

[0022] Embodiment 2 Identification of the structure of rapeseed

[0023] HREI-MS gives molecular mass [M+1]=438.2397 (calculated value is 438.2393), 1 H and 13 C NMR data are shown in Table 1.

[0024] Table 1. Rapeseed alkaloids 1 H and 13 C NMR data

[0025]

[0026] 1 H-NMR (DMSO-d 6 , 500MHz) spectrum, there should be two proton signals of the AA'BB' system at δ6.78, 7.39, and 7.30, and one proton signal at δ6.49, 6.55, 7.31, and 7.34, which are ene hydrogen protons Signals, J = 11 and 11.5 indicate the presence of two cis double bonds in the compound. δ1.48~δ3.25 are the signals of protons on saturated carbons or protons connected to heteroatoms. 13 The C-NMR spectrum shows that δ166.0, 166.4 is the carbonyl carbon signal, and the carbonyl is connected in the p-π conjugated system. δ159.4, 159.3 are the oxygen carbon signals on the benzene ring, δ116.2, 129.4, 129.6 are the carbon signals of the benzene ring AA'BB' system, and 1 The H-NMR spectral data are co...

Embodiment 3

[0027] Example 3 Brassica alkaloid anti-prostatitis activity evaluation

[0028] Using the model of prostatitis induced by carrageenan in rats, the anti-prostatitis test of rapeseed was carried out in vivo, and the four indexes of prostate wet weight, prostate index, IL-8 and spleen index were used to detect the effect of rapeseed on prostatitis. , and the results are shown in Table 2.

[0029] Table 2. Inhibitory effect of rapeseed alkaloids on prostatic inflammation in rats induced by carrageenan

[0030]

[0031] n=10; * indicates that there is a significant difference compared with the model group, P<0.05; ** indicates that there is a very significant difference compared with the model group, P<0.01

[0032] The above results showed that the wet weight and prostate index of the model group increased significantly (P<0.01). It can be seen that the prostate tissue was infiltrated and edematized by a large number of inflammatory cells due to the inflammatory reaction, fol...

technical field

[0001] The invention relates to a kind of rape flower alkali and its application, belonging to the fields of food, health products and medicine. Background technique

[0002] Rapeseed pollen is pollen of oilseed rape (Brassica campestris L.), and rape bee pollen (beepollen) is pollen balls collected by bees from the anthers of rapeseed plants. Rapeseed pollen and rapeseed bee pollen have a variety of physiological functions, especially for benign prostatic hyperplasia and prostatitis. If its functional components can be extracted from rape pollen and its structure identified, it is hoped that it can be used to prepare drugs, or the substance can be synthesized by chemical methods to prepare drugs. However, the current chemical components in rape pollen and rape bee pollen In most of the reports, the crude extract with the above effects is obtained from rapeseed pollen, but it is still unclear what kind of substance is the functional ingredient that inhibits ...

Examples

Embodiment 1

[0020] Get 5kg rape bee pollen, pulverize, pass through a 40-mesh sieve, take the under-sieve powder, crush the over-sieve again through a 40-mesh sieve, take the under-sieve powder, place the under-sieve powder in a 50-liter extraction tank, add 40 1 liter of ethanol aqueous solution with a volume fraction of 80%, extracted at room temperature for 3 hours, filtered, took the filtrate, and repeated extraction of the filter residue twice to obtain 115 liters of filtrate, concentrated under reduced pressure to 6 liters, poured into the extraction tank, and added 6 liters of Degrease with n-hexane, stir at 60r / min for 40 minutes, let it stand for 5 hours, separate the n-hexane phase, repeat the degreasing once more, take the sample after the second degreasing, add 6 liters of deionized water, open the cover and stir at 50°C The residual normal hexane was volatilized in 40 minutes, and then passed through the macroporous resin column AB-8 (10×150cm) post, and was first eluted with ...

Embodiment 2

[0022] Embodiment 2 Identification of the structure of rapeseed

[0023] HREI-MS gives molecular mass [M+1]=438.2397 (calculated value is 438.2393), 1 H and 13 C NMR data are shown in Table 1.

[0024] Table 1. Rapeseed alkaloids 1 H and 13 C NMR data

[0025]

[0026] 1 H-NMR (DMSO-d 6 , 500MHz) spectrum, there should be two proton signals of the AA'BB' system at δ6.78, 7.39, and 7.30, and one proton signal at δ6.49, 6.55, 7.31, and 7.34, which are ene hydrogen protons Signals, J = 11 and 11.5 indicate the presence of two cis double bonds in the compound. δ1.48~δ3.25 are the signals of protons on saturated carbons or protons connected to heteroatoms. 13 The C-NMR spectrum shows that δ166.0, 166.4 is the carbonyl carbon signal, and the carbonyl is connected in the p-π conjugated system. δ159.4, 159.3 are the oxygen carbon signals on the benzene ring, δ116.2, 129.4, 129.6 are the carbon signals of the benzene ring AA'BB' system, and 1 The H-NMR spectral data are co...

Embodiment 3

[0027] Example 3 Brassica alkaloid anti-prostatitis activity evaluation

[0028] Using the model of prostatitis induced by carrageenan in rats, the anti-prostatitis test of rapeseed was carried out in vivo, and the four indexes of prostate wet weight, prostate index, IL-8 and spleen index were used to detect the effect of rapeseed on prostatitis. , and the results are shown in Table 2.

[0029] Table 2. Inhibitory effect of rapeseed alkaloids on prostatic inflammation in rats induced by carrageenan

[0030]

[0031] n=10; * indicates that there is a significant difference compared with the model group, P<0.05; ** indicates that there is a very significant difference compared with the model group, P<0.01

[0032] The above results showed that the wet weight and prostate index of the model group increased significantly (P<0.01). It can be seen that the prostate tissue was infiltrated and edematized by a large number of inflammatory cells due to the inflammatory reaction, fol...

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