| Rapeseed refers to the seed of Cruciferous Brassica campestris L., and it is officially recorded in Compendium of Materia Medica that rapeseed has the therapeutic effects of blood activating, stasis dispersing, swelling diminishing, hard lump resolving, bowel relaxing, stagnant relieving, blooding circulation promoting, etc. Rapeseed can be either orally taken to cure postpartum lochiorrhea, abdominalgia with blood stasis, rheumatism, arthralgia, migraine, constipation, etc., or externally used to eliminate carbuncle and erysipelas, and is a kind of Chinese traditional medicine not commonly used in clinical treatment. Rape is one of the main oil crops and honey crops in China, while rapeseed is one of the main raw materials with numerous output for producing grease. Rapeseed meal, as the major byproduct after rapeseed processing, is fairly rich in resources. Besides rich natural vegetable proteins, rapeseed meal also contains many anti-nutritional substances, such as glucosinolate, phytic acid, tannins, etc. The rapeseed meal was restrictedly developed and utilized once upon a time, and was used as cheap fodder and fertilizer only for a long time, which results in huge resource wastes. Therefore, we systematically analyzed the chemical components of the rapeseed meal from the perspectives of resource recycling in this paper, aiming to find useful bioactive components for the modern medical industry so as to provide theoretical basis for further development of rapeseed meal and provide theoretical foundation for preliminary study on the pharmacodynamic material basis of the rapeseed by comparing with and making reference to the components of rapeseed. In this paper, there were82chemical compounds isolated and obtained in total by using macroporous ALCC, Sephadex LH-20, ODS Column Chromatography, Slica column chromatography, preparative HPLC and the crystallization process in combination. After applying the spectroscopy technology as well as the physical and chemical property analysis, the structures of the85chemical compounds isolated and obtained were identified as follows:1-undecanol (CZP-1),1-icosanol (CZP-2), palmatic acid (CZP-3), campestrol (CZP-4), Daucosterol (CZP-5),7-oxo-stigmasterol (CZP-6), crinosterol (CZP-7), oleic acid (CZP-8),7a-hydroxyl-stigmasterol (CZP-9), β-sitosterol (CZP-10),9,12-Octadecadienoic acid (Z,Z)-,2,3-dihydroxypropyl ester (CZP-11), Trans-sinapic acid (CZP-12),Trans-Sinapic acid methylester (CZP-13), Trans-Sinapic acid ethylester (CZP-14), Vinylsyringol (CZP-15),1-ethoxyethyl-3-(4-hydroxy-3,5-dimethoxyphenyl)(CZP-16),4-ethyl syringol (CZP-17),(2E)-ethyl3-(4-hydroxy-3,5-dimethoxyphenyl)propionic (CZP-18), Acetosyringone (CZP-19), Syringaldehyde (CZP-20),2,5-dihydroxybenzoic acid (CZP-21), Vanillic acid (CZP-22), protocatechuic acid methyl ester (CZP-23),3,5-dimethoxy-4-hydroxylbenzoic acid (CZP-24), protocatechuic aldehyde (CZP-25),1-(S)-Methoxy-1-(3,5-dimethoxy-4-hydroxyphenyl) ethane (CZP-26), p-Hydroxybenzoic acid (CZP-27), protocatechuic acid (CZP-28), p-Hydroxybenzaldehyde (CZP-29), dihydrosinapic acid (CZP-30),(6R,9S)-9-hydroxymegastigman-4-en-3-one (CZP-31),(S)-2-sinapoly-4-pentenenitrile (CZP-32), Succinic acid (CZP-33),(1H)-Indole-3-acetonitrile (CZP-34),(R)-(-)-dehydrovomifoliol (CZP-35), Ethyl2-oxo-1,2,3,4-tetrahydroquinoline-4-carboxylate (CZP-36),1H-indole-3-carbaldehyde (CZP-37),4-hydroxy-1H-indole-3-carbaldehyde (CZP-38),6-hydroxy-1H-indole-3-carboxylic acid (CZP-39),5-vinylthiazole-2-dione (CZP-40),5-hydroxy-4(1H)-quinazolinone (CZP-41),4-hydroxy-2-quinolinone (CZP-42),5-hydroxy-quinazoline-2(1H),4(3H)-dione (CZP-43), Coixspirolactam C (CZP-44),(-)-Eudesmin (CZP-45),(+)-Magnolin (CZP-46), Yangambin (CZP-47), Isolariciresinol (CZP-48), descurainolide B (CZP-49),1,2-di-O-sinapoyl-β-D-glucopyranose (CZP-50), Spicatolignan B (CZP-51), erythro-guaiacylglycerol-β-ferulic acid ether (CZP-52), Sinapic acid5-hydroxymethylfurfural ester (CZP-53),5-Hydroxymethylfurfuiral (CZP-54), Dibutyl phthalate (CZP-55),(6R,9R)-9-hydroxymegastigman-4-en-3-one (CZP-56), blumenol A (CZP-57),3,9-dihydroxy-5,7-megastigmadien-4-one (CZP-58),(5Z,7E)-4,4-dimethyl-5-acetyl-5,7-nonadienoic acid (CZP-59),2-β-D-glucopyranosylsulfanyl-1H-indole-3-acetonitrile (CZP-60), Kaempferol (CZP-61), Kaempferol-3-β-D-glucopyranoside (CZP-62), Isorhamnetin-3-β-D-glucopyr- anoside (CZP-63), Kaempferol-7-β-D-glucopyranoside (CZP-64),6-oxo-octadecanedioic acid (CZP-65), Kaempferol-3-O-β-D-glucopyranosyl-(1â†'2)-β-D-glucopyranoside.(CZP-66), Kaempferol3,7,4’-tri-O-β-D-glucopyranoside (CZP-67), Kaempferol-3-O-β-D-glucopyranosyl-(1â†'2)-β-D-glucopyranosyl-7-O-β-D-glucopyranoside (CZP-68), Isorhamnetin-3,7,4’-tri-β-O-glucopyranoside (CZP-69), Kaempferol-3-O-(2-O-sinapoyl)-β-D-glucopyranosyl-(1â†'2)-β-D-glucopyranoside-7-O-β-D-glucopyranoside(CZP-70), Kaempferol-3-O-6-sinapoyl)-β-D-glucopyranosyl-(1â†'2)-O-β-D-glucopyranoside-7-O-β-D-glucopyranoside (CZP-71), Kaempferol-4’-O-(6-sinapoyl)-β-D-glucopyranoside-3,7-di-O-β-D-glucopyranoside(CZP-72), Kaempferol-3-O-(3-sinapoyl)-β-D-glucopyranosyl-(1-2)-O-β-D-glucopyranoside-7-O-β-D-glucopyranoside (CZP-73),5,6-dihydro-6-hydroxy-2-(1’,5’-dihydro-4’-(2"-hydroxyethyl)-3’5’-dimethyl-(1’H)-pyrrol-2’-one)-3-methyl-cyclopenta[b]-pyrrol-4(1H)-one (CZP-74), β-D-frueofuranosyl-α-D-(6-sinapoyl)-glucopyranosid (CZP-75), nicotinic acid (CZP-76),(2R*,3R*,4S*,5R*)-dimethyl2,5-bis(4-hydroxy-3,5-dimethoxyphenyl) tetrahydrothiophene-3,4-dicarboxylate1-oxide(CZP-77),(2R*,3R*,4R*)-methyl4-(bis(4-hydroxy-3,5-dimethoxyphenyl) methyl)-2-methoxy-5-oxotetrahydrofuran-3-carboxylate (CZP-78),1-(S)-hydroxy-1-(3,5-dimethoxy-4-hydroxyphenyl) ethane (CZP-79),7S,8R,8’R-(-)-lariciresinol-4,4’-O-bis-β-D-glucopyranoside(CZP-80),7S,8R,8’R-(-)-lariciresinol-4-O-β-D-glucopyranoside (CZP-81),1-methyl-6-((4-methyl amio)-methyl benzoate)-2,3-diketopiperazine (CZP-82),5-allyloxazolidin-2-one (CZP-83), Adenosine (CZP-84), Isorhamnetin-3-O-(6-sinapoyl)-β-D-glucopyranosyl-(1-2)-O-β-D-glucopyranoside (CZP-85). The compound CZP-71, CZP-72, CZP-73, CZP-74, CZP-77, CZP-78, CZP-82, CZP-60, CZP-32, CZP-59were new compounds, CZP-36, CZP-83were the new natural produtcs and most of the compounds were isolated from the rapeseed meal for the first time.In addition, based on the studies on the chemical components, we conducted the antioxidant activity screening of17monomeric compounds among the82chemical compounds isolated and obtained in this paper. The experimental results showed that the flavonoids monomers had significant effects against the damage from oxidative stress, and CZP-70, CZP-61and CZP-64had the most obvious antioxidation effects, while some lignanoids monomers (CZP-45～47) can reduce LDH activity of cell culture supernatants to different degrees with excellent antioxidation effects. And in this paper,75%ethanol extract of rapeseed and rapeseed meals were analyzed and evaluation by using LC-MS", and10of16kinds of chemical constituents were identified respectively, which have laid the foundation for study of the Chinese medicine efficacy material base for Brassica campestris L. |
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