| 汤宣亮,余小青,张毅,等.冈村凹顶藻的倍半萜类化学成分及抗菌活性研究[J].中国海洋药物,2015,34(6):12-22. |
| 冈村凹顶藻的倍半萜类化学成分及抗菌活性研究 |
| Study on the chemical constituents and antimicrobial activities of sesquiterpenes from the red alga Laurencia okamurai Yamada |
| 投稿时间：2015-04-02 修订日期：2015-04-14 |
| DOI： |
| 中文关键词: 冈村凹顶藻 化学成分 倍半萜 抗真菌活性 抗细菌活性 |
| English Keywords:Laurencia okamurai chemical constituents sesquiterpenes antifungal activity antibacterial activity |
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| 中文摘要: |
| 目的 分离鉴定冈村凹顶藻中的倍半萜类成分，供抗菌活性筛选。方法 综合利用各种柱层析方法分离纯化化合物并利用光谱学方法解析化合物结构；选择4株真菌为实验菌株，对6个倍半萜进行体外抗真菌活性测定；选择2株细菌为实验菌株，对所有倍半萜进行体外抗细菌活性测定。结果 分离得到17个倍半萜，分别鉴定为海兔阿普里醇 (1)、劳藻过氧素 (2)、海兔阿普里醛 (3)、 α-异溴花侧伯烯 (4)、α-异花侧伯烯醇 (5)、花侧伯烯醚 (6)、月桂烷-11-烯-10-醇 (7)、劳藻酚 (8)、劳藻酚乙酰化物 (9)、去溴劳藻酚 (10)、异劳藻酚 (11)、异劳藻酚乙酰化物 (12)、约翰斯顿醇 (13)、帕西菲醇 (14)、10-溴-α-花柏烯 (15)、10-溴-β-花柏烯 (16)、9-羟基-3-氯-4,10-二溴-α-花柏烯 (17)，并对所获得的倍半萜进行抗菌活性筛选。结论 化合物5和7为首次从冈村凹顶藻中分离得到；应用1D和2D NMR首次对化合物6的1H和13C NMR数据进行了全归属；化合物5和13对光滑假丝酵母菌显示了明显的抑制作用，其MIC80值分别为1和4 μg/mL，与两性霉素B（2 μg/mL）和氟康唑（1 μg/mL）相当，而化合物2、8和9对新生隐球菌均具有一定的抑制作用；另外，化合物2、8~10、15和17对金黄色葡萄球菌均显示了不同程度的抑制作用，其中化合物8和9具有良好的杀菌活性，其MIC80值分别为2.3和10.5 μg/mL。 |
| English Summary: |
| Objective To isolate and identify sesquiterpenes of the red alga Laurencia okamurai Yamada and to evaluate their antimicrobial activities. Methods Compounds were isolated and purified by means of various chromatographic techniques including silica gel and Sephadex LH-20 column chromatography and reverse phase HPLC, while their structures were elucidated on the basis of spectroscopic analysis. The in vitro antifungal activity of six sesquiterpenes against four fungi (Cryptococcus neoformans, Candida glabrata, Trichophyton rubrum, and Aspergillus fumigatus) and antibacterial activity of all the isolates against two bacteria (Staphylococcus aureus and Pseudomonas aeruginosa) were evaluated using broth micro-dilution method. Results Seventeen known sesquiterpenes were isolated and identified as aplysinol (1), laureperoxide (2), aplysinal (3), α-isobromocuparene (4), α-isocuparenol (5), cuparene-type ether (6), laur-11-en-10-ol (7), laurinterol (8), laurinterol acetate (9), debromolaurinterol (10), isolaurinterol (11), isolaurinterol acetate (12), johnstonol (13), pacifenol (14), 10-bromo-α-chamigrene (15), 10-bromo-β-chamigrene (16), and 4,10-dibromo-3-chloro-9-hydroxy-α-chamigrene (17), respectively. All of the isolated sesquiterpenes were evaluated for antimicrobial activities. Conclusion Compounds 5 and 7 were isolated for the first time from Laurencia okamurai. The full 1H and 13C NMR data were unambiguously assigned by 1D and 2D NMR (1H–1H COSY, HMQC, HMBC, and ROESY) experiments. In in vitro antifungal bioassays, compounds 5 and 13 exhibited potent inhibitory activity against the fungus Candida glabrata with MIC80 values of 1 and 4 μg/mL, respectively, when compared to the positive controls, amphotericin B (MIC80 = 2 μg/mL) and fluconazole (MIC80 = 1 μg/mL), while compounds 2, 8, and 9 showed moderate inhibitory activity against the fungus Cryptococcus neoformans. In addition, compounds 2, 8–10, 15, and 17 displayed different levels of antibacterial activity against the bacterium Staphylococcus aureus. Among them, compounds 8 and 9 exhibited potent antibacterial activity with MIC80 values of 2.3 and 10.5 μg/mL, respectively. |
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