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黑指纹海兔Aplysia dactylomela中的萜类化合物及其抗炎和细胞毒活性
邓家珍1,2, 彭翰阳2,3, 曾艳波1,2
1.海南大学 海洋生物与水产学院, 海南 海口 570228;2.中国热带农业科学院 热带生物技术研究所 海南省海洋生物资源功能性成分研究与利用重点实验室, 海南 海口 571101;3.南京中医药大学 药学院, 江苏 南京 210023
摘要:
本研究首次以中国三沙市七连屿的黑指纹海兔Aplysia dactylomela为研究对象,对其化学成分及生物活性进行研究。运用硅胶柱层析、Sephadex LH-20凝胶柱层析和半制备型高效液相色谱等分离技术对黑指纹海兔A.dactylomela的次生代谢物进行分离纯化,结合核磁共振波谱和质谱等波谱数据,并与文献数据进行比对,对所分离到的化合物进行结构鉴定。从黑指纹海兔A.dactylomela中分离鉴定了11个化合物,其结构分别鉴定为:palisadin A (1)、(−)-aplysistatin (2)、5β-acetoxypalisadin A (3)、5-acetoxypalisadin B (4)、luzodiol (5)、pileaterpene C (6)、isoaplysin-20(7)、isoconcinndiol (8)、cis-pachydictyol B (9)、dictytriol (10)和brevisnoside A (11)。其中,化合物1~5、7~8为溴化萜类化合物,化合物6、9~11为萜类化合物。抗炎和细胞毒活性测试结果显示,化合物1~4、6和10均具有不同程度的抗炎活性,且无细胞毒性。其中化合物2(IC50值为(3.42±0.25)μmol/L)的抗炎活性比阳性对照槲皮素的抗炎活性(IC50值为(9.98±1.14)μmol/L)更强。化合物1和4对人慢性髓原白血病细胞(K562)具有中等抑制作用,其IC50值分别为(27.82±0.06)和(19.99±1.96)μmol/L。
关键词:  黑指纹海兔  化学成分  溴化萜类化合物  抗炎活性  细胞毒活性
DOI:10.11759/hykx20240821001
分类号:O629
基金项目:国家自然科学基金(41776093);中国热带农业科学院国家热带农业科学中心科技创新团队项目(CATASCXTD202416)
Terpenoids with anti-inflammatory and cytotoxicity activities from the sea hare Aplysia dactylomela
DENG Jiazhen1,2, PENG Hanyang2,3, ZENG Yanbo1,2
1.College of Marine Biology and Fisheries, Hainan University, Haikou 570228, China;2.Hainan Provincial Key Laboratory for Functional Components Research and Utilization of Marine Bio-resources, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China;3.College of Pharmaceutical Sciences, Nanjing University of Chinese Medicine, Nanjing 210023, China
Abstract:
This study investigated the chemical components and their biological activities of the sea hare Aplysia dactylomela, which was collected from Qi Lian Yu, Sansha, Hainan. The secondary metabolites of A. dactylomela were isolated and purified through silica gel chromatography, octadecylsilyl, Sephadex LH-20 gel column chromatography, and semipreparative high-performance liquid chromatography. Their structures were identified by nuclear magnetic resonance spectroscopy and mass spectrometry data and compared with literature data. Eleven terpenoids were identified from the sea hare A. dactylomela, including palisadin A (1), (−)-aplysistatin (2), 5b-acetoxypalisadin A (3), 5-acetoxypalisadin B (4), luzodiol (5), pileaterpene C (6), isoaplysin-20 (7), isoconcinndiol (8), cis-pachydictyol B (9), dictytriol (10), and brevisnoside A (11). The results of anti-inflammatory and cytotoxicity activity tests showed that compounds 1–4, 6, and 10 had different levels of anti-inflammatory activity and no cell toxicity. Specifically, the anti-inflammatory activity of compound 2 (with an IC50 value of (3.42 ± 0.25) µmol/L) was more pronounced than the anti-inflammatory activity of positive control quercetin (with an IC50 value of (9.98 ± 1.14) µmol/L). Compounds 1 and 4 had medium cytotoxicity activity on human chronic myeloid leukemia cells (K562), with IC50 values of (27.82 ± 0.06) and (19.99 ± 1.96) µmol/L, respectively.
Key words:  Aplysia dactylomela  chemical constituent  terpenoid bromide  anti-inflammatory activity  cytotoxicity activity
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