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肉桂子化学成分及其生物活性的研究
郭若洛·音登芝
Subtype博士
Thesis Advisor阿吉艾克拜尔·艾萨、姚广民
2018-06-02
Degree Grantor中国科学院大学
Place of Conferral北京
Degree Discipline有机化学
Keyword肉桂子 化学成分 二萜 倍半萜 抑菌活性
Abstract

肉桂子为樟科樟属植物肉桂(Cinnamomum cassia Presl.)的干燥未成熟带宿萼的果实,是一种民族医常用的药材,也是大众常见的调味品。据《中华本草》-维吾尔药卷记载,其主要功能为生干生热,祛寒补心,芳香开窍,温中开胃,增强消化。主治湿寒性或黏液质性心脏和肠胃疾病。根据文献调研,未见到关于肉桂子的化学成分的研究以及生物活性方面的研究报道,因此,本文首次对肉桂子的化学成分进行了分离鉴定工作。运用正相硅胶,反相硅胶,Sephadex LH-20以及RP HPLC等多种现代色谱分离技术,从肉桂子乙醇提取物的甲醇部位和乙酸乙酯部位分离得到47个化合物。借助核磁共振,紫外,高分辨质谱等方法确定了47个化合物的结构,其中8个新化合物,化合物1–3, 5和6为二萜类新化合物,13–15为倍半萜类新化合物。化合物的结构类型包括倍半萜,二萜,单萜,酚苷,醇苷,苯丙素类等化合物。其中,二萜类新化合物1–3命名为cinnamomol G,cinnamomol H, cinnamomol I,新化合物5命名为20-nor-cinncassiol A,新化合物6命名为4-hydroxy-cinncassiol A 19-O-β-D-glucopyranoside,倍半萜类新化合物13命名为cinnamosim A,化合物14命名为cinnamosim B,化合物15命名为xylcarpin F。新化合物1的衍生物化合物12命名为Cinnamomol A 19-O-4- Bromobenzoyl。其余已知化合物被鉴定为cinnamomol A (4),anhydrocinnzeylanine (7),cinncassiol A 19-O-β-D-glucopyranoside (8),cinncassiol A (9),cinnzeylanol (10),cinncassiol D2 (11),(7R*)-Oppsit-4(15)-ene-1β,7α-diol (16),oppsit-4(15)-ene-1β,11-diol (17),4(15)-eudesmene-1β,7α,11-triol (18),6α-dihydroxyeudesm-4(15)-ene (19),(1β,4β,6β)-gorgonane-1,4,11-triol (20),aromadendrane-4β,10α-diol (21),aromadendrane-4α,10α-diol (22),1-epimer-aromadendrane-4β, 10α-diol (23),caryolane-1,9β-diol (24),4α-10α-dihydroxy-5β-H-guaja-6-ene (25),4α,10β,11-trihydroxy-1,5-trans-guaiane-6,7-ene (26),Turpinionoside A (27),3,7-dimethyl-1-octene-3,6,7-triol (28, 29),3,7-dimethyl-oct-1-en-3,6,7-triol-6-O-β-D-glucopyranoside (30, 31),trans-Linalool-3,6-oxide-β-D-glucopyranoside (32),1,6,7-trihdroxy-3,7-dimethyloct-2-ene (33),phenylmethanol O-α-L-arabinofuranosyl (1→6)-β-D-glucopyranoside (34),Icariside F2 (35),Icariside DC (36),2-phenylethyl-O-β-D-glucoside (37),2-O-β-D-glucosyl-(1S)-phenylethylee glycol (38),Isotachioside (39),cinnacassides F (40),cinnacassides G (41),1-(4-hydroxy-3-methoxyphenyl)-1,2,3-propanetriol (42),cinnamic acid (43),butan-2-O-β-D-glucopyranoside (44),butan-2-O-β-D-glucopyranoside-(1-6)-O-β-D-apiofuranosyl (45),5-Phenylpentyl β-D-Glucopyranoside (46),2,3,4,5-Tetrahydroxybenzyl alcohol (47)。肉桂具有多方面的活性,其中包括效果显著的抗菌作用,因此,本文评价了倍半萜类化合物13–14和16–25对三种致病菌白色念珠菌,金黄色葡萄球菌,大肠杆菌的抗菌活性。结果表明:新化合物13 和14对白色念珠菌均具有良好的抑制作用,已知化合物19和22对三种菌均具有较好的抑制作用。因此,肉桂子中倍半萜类化合物可作为防腐抑菌的具有潜力的候选药物,对于天然产物防腐抗菌剂的研究提供了新的方向。

Other Abstract
The dried Cassia buds (the immature fruits of Cinnamomum cassia) are widely used as seasoning, and also applied in traditional medicine to treat cardiothoracic pains, cold pain in the stomach and abdomen, nausea, vomiting, belch, hiccup, cough, and dyspnea. In this study, the chemical constituents of the cassia buds were investigated for the first time, and the researches about the pharmacological were no reported.With repeated extensive column chromatographies (silica gel, YMC gel, Sephadex LH-20, HPLC), 47 compounds were isolated from the MeOH and EtOAc part of the fruits of C. cassia. According to the NMR, MS, HRESIMS, UV spectroscopic analysis, the structures of these compounds were established, including 8 new compounds. The compound 1-3, 5 and 6 were new diterpenes, and 13-15 were new sesquiterpenes. Among them, the new deterpenoids 1-3 named as cinnamomol G, cinnamomol H, cinnamomol I, the new compound 5 named as 20-nor-cinncassiol A, the new compound 6 named as 4-hydroxy-cinncassiol A 19-O-β-D-glucopyranoside, the new sesquiterpenoid compound 13 named as cinnamosim A, compound 14 named as cinnamosim B, compound 15 named as xylcarpin F. The derivative of compound 1, compound 12 named as Cinnamomol A 19-O-4- Bromobenzoyl. The other known compounds were established as cinnamomol A (4),anhydrocinnzeylanine (7),cinncassiol A 19-O-β-D-glucopyranoside (8),cinncassiol A (9),cinnzeylanol (10),cinncassiol D2 (11),(7R*)-Oppsit-4(15)-ene-1β,7α-diol (16),oppsit-4(15)-ene-1β,11-diol (17),4(15)-eudesmene-1β,7α,11-triol (18),6α-dihydroxyeudesm-4(15)-ene (19),(1β,4β,6β)-gorgonane-1,4,11-triol (20),aromadendrane-4β,10α-diol (21),aromadendrane-4α,10α-diol (22),1-epimer-aromadendrane-4β, 10α-diol (23),caryolane-1,9β-diol (24),4α-10α-dihydroxy-5β-H-guaja-6-ene (25),4α,10β,11-trihydroxy-1,5-trans-guaiane-6,7-ene (26),Turpinionoside A (27),3,7-dimethyl-1-octene-3,6,7-triol (28, 29),3,7-dimethyl-oct-1-en-3,6,7-triol-6-O-β-D-glucopyranoside (30, 31),trans-Linalool-3,6-oxide-β-D-glucopyranoside (32),1,6,7-trihdroxy-3,7-dimethyloct-2-ene (33),phenylmethanol O-α-L-arabinofuranosyl (1→6)-β-D-glucopyranoside (34),Icariside F2 (35),Icariside DC (36),2-phenylethyl-O-β-D-glucoside (37),2-O-β-D-glucosyl-(1S)-phenylethylee glycol (38),Isotachioside (39),cinnacassides F (40),cinnacassides G (41),1-(4-hydroxy-3-methoxyphenyl)-1,2,3-propanetriol (42),cinnamic acid (43),butan-2-O-β-D-glucopyranoside (44),butan-2-O-β-D-glucopyranoside-(1-6)-O-β-D-apiofuranosyl (45),5-Phenylpentyl β-D-Glucopyranoside (46),2,3,4,5-Tetrahydroxybenzyl alcohol (47)。C. cassia. has been reported with remarkable antimicrobial activities, however, there was no report about the immature fruits of C. cassia. Therefore, the sesquiterpene compounds 13-14 and 16-25 were evaluated for their antimicrobial activities against three representative microbials Candida albicans, Escherichia coli, and Staphylococcus aureus. The new compound 13 and 14 showed antifungal activity against C. albicans with the diameter of inhibitory zones of 11 mm and 10 mm. Compounds 19 and 22 exhibited inhibitory effects against all of test bacterium. As a result, the new compound 13 and 14 were potential candidates for fungicide, and providing the possibility to find the new type antibacterial natural product.
Document Type学位论文
Identifierhttp://ir.xjipc.cas.cn/handle/365002/5458
Collection资源化学研究室
Recommended Citation
GB/T 7714
郭若洛·音登芝. 肉桂子化学成分及其生物活性的研究[D]. 北京. 中国科学院大学,2018.
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