中国南海山海绵<i>Mycale</i> sp.的化学成分研究

孙佳宝; 王淑萍; 王洁; 刘莉; 韩兵男; 林厚文

doi:10.3969/j.issn.1006-0111.2017.04.006

中国南海山海绵Mycale sp.的化学成分研究

doi: 10.3969/j.issn.1006-0111.2017.04.006

1.
上海交通大学医学院附属仁济医院药学部, 上海 200127
2.
沈阳药科大学中药学院, 辽宁沈阳 110016

基金项目: 国家自然科学基金（81373321）

Study on chemical constituents of sponge Mycale sp. from the South China Sea

1.
Department of Pharmacy, Renji Hospital Affiliated to School of Medicine, Shanghai JiaoTong University, Shanghai 200127, China
2.
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China

摘要: 目的对采自中国南海山海绵Mycale sp.的化学成分进行研究。方法采用硅胶柱色谱、Sephadex LH-20凝胶柱色谱、高效液相色谱等多种色谱学分离手段，对山海绵Mycale sp.的乙酸乙酯萃取层进行分离纯化；应用现代波谱技术，结合理化性质与文献报道对化合物进行结构鉴定；用Cell Counting Kit-8（CCK-8）法对化合物进行体外人乳腺癌细胞株MCF-7及人肺癌细胞株PC9细胞生长抑制活性进行测试。结果共分离得到10个化合物，分别鉴定为：环（脯-异亮）二肽[cyclo-（Pro-Ile）]（ 1 ），环（脯-亮）二肽[cyclo-（Pro-Leu）]（ 2 ），环（异亮-亮）二肽[cyclo-（Ile-Leu）]（ 3 ），环（苯丙-脯）二肽[cyclo-（Phe-Pro）]（ 4 ），环（苯丙-缬）二肽[cyclo-（Phe-Val）]（ 5 ），环（苯丙-亮）二肽[cyclo-（Phe-Leu）]（ 6 ），环（苯丙-异亮）二肽[cyclo-（Phe-Ile）]（ 7 ），2'-deoxythymidine（ 8 ），胸腺嘧啶（thymine）（ 9 ），5-hydroxy-3，4-dimethy-5-pentyl-2（5H）-furanone（ 10 ）。经体外活性筛选发现，这些化合物对MCF-7及PC9未显示明显的生长抑制活性。结论化合物 1 、 2 、 4 、 5 、 6 、 7 和 10 均为首次从该属海绵中分离得到，本研究首次对化合物 1 ~ 10 的抗肿瘤活性进行了评价。
- Mycalesp. /
- 化学成分 /
- 环二肽 /
- 生长抑制活性
Abstract: Objective To investigate the chemical constituents of marine sponge Mycale sp. collected from the South China Sea. Methods The ethyl acetate extract of the marine sponge Mycale sp. was separated and purified by repeated column chromatography on silica gel, Sephadex LH-20 and reversed-phase high-performance liquid chromatography (RP-HPLC). The structures of these compounds were identified by means of various modern spectroscopic techniques and comparison with their physicochemical properties to reported data. The tumor cell growth inhibitory activities of these compounds against human breast cancer cell lines MCF-7 and human lung cancer cell lines PC9 were tested by Cell Counting Kit-8 (CCK-8) method. Results Ten compounds were isolated and identified as cyclo-(Pro-Ile)( 1 ),cyclo-(Pro-Leu)( 2 ),cyclo-(Ile-Leu)( 3 ),cyclo-(Phe-Pro)( 4 ),cyclo-(Phe-Val)( 5 ),cyclo-(Phe-Leu)( 6 ),cyclo-(Phe-Ile)( 7 ), 2'-deoxythymidine ( 8 ), thymine ( 9 ), 5-hydroxy-3,4-dimethyl-5-pentyl-2(5H)-furanone ( 10 ). These compounds showed weak tumor cell growth inhibitory activities toward cells MCF-7 and PC9 in vitro. Conclusion Compounds 1 , 2 , 4 , 5 , 6 , 7 and 10 were isolated from the sponge Mycale sp. for the first time. It is the first time to report the antitumor activity evaluation for compounds 1 ~ 10 .
- Mycale sp. /
- chemical constituents /
- cyclic dipeptide /
- growth inhibitory activity

[1]	Ortega MJ, Zubia E, Carballo JL,et al. New cytotoxic metabolites from the sponge Mycale micracanthoxea[J]. Tetrahedron, 1997, 53(1):331-340.
[2]	Fusetani N, Yasumuro K, Matsunaga S,et al. Mycalolides A-C hybrid macrolides of ulapualides and halichondramide, from a sponge of the genus Mycale[J]. Tetrahedron Lett, 1989, 30(21):2809-2812.
[3]	Capon RJ. Two new norsesterterpene cyclic peroxides from a marine sponge,Mycale (Carmia)cf. spongiosa[J]. J NatProd, 1991, 54(1):190-195.
[4]	Capon RJ, Macleod JK. Structural and stereochemical studies on marine norterpene cyclic peroxides[J]. Tetrahedron, 1985, 41(16):3391-3404.
[5]	Zhou XF, Lin XP, Guo XY,et al. Chemical constituents of the sponge Mycale species from South China Sea[J]. Rec Nat Prod, 2013, 7(2):119-123.
[6]	Nakao Y, Yoshida S, Matsunaga S,et al. Azumamides A-E: histone deacetylase inhibitory cyclic tetrapeptides from the marine sponge Mycale izuensis[J].Angew Chem Int Ed,2006, 45(45):7553-7557.
[7]	Perry NB, Blunt JW, Munro MHG,et al. Mycalamide A, an antiviral compound from a New Zealand sponge of the genus Mycale[J]. J Am Chem Soc, 1988, 110(14):4850-4851.
[8]	Northcote PT, Blunt JW, Munro MHG. Pateamine: a potent cytotoxin from the New Zealand marine sponge, mycale sp.[J]. Tetrahedron Lett, 1991, 32(44):6411-6414.
[9]	West LM, Northcote PT, Battershill CN. Peloruside A: a potent cytotoxic macrolide isolated from the New Zealand marine sponge Mycale sp.[J]. J Org Chem,2000, 65(2):445-449.
[10]	Adamczeski M, Reed AR, Crews P. New and known diketopiperazines from the Caribbean sponge,Calyx cf. podatypa.[J].J NatProd, 1995, 58(2):201-208.
[11]	Zhao PJ, Wang HX, Li GH,et al. Secondary metabolites from endophytic Streptomyces sp. Lz531[J]. Chem Biodivers, 2007, 4(5):899-904.
[12]	Wang S, Tan N, Yang Y, et al. Cyclodipeptides from the roots of Panax notoginseng[J]. Nat Prod Res Dev, 2004, 16:383-386.
[13]	Shu ZP, Li XL, Xu BQ, et al.Piperazine constituents in fruits of Physalis alkekengi var. francheti[J]. Chin Tradit Herbal Drugs, 2014, 45(4):471-475.
[14]	Ouyang MA. A new adenosyl-alkaloid from Ostrea rivularis[J]. Nat Prod Res, 2006, 20(1): 79-83.
[15]	苏丽丽,唐旭利,张婧,等.中国南海海底柏柳珊瑚化学成分研究[J]. 中国海洋药物,2011, 30(5):18-22.
[16]	Degenkolb T, Gams W, Br ckner H. Natural cyclopeptaibiotics and related cyclic tetrapeptides: structural diversity and future prospects[J]. Chem Biodivers, 2008, 5(5):693-706.

[1]	杨贺英, 罗彩萍, 彭婷, 梁文仪, 沈颂章, 苏娟. 花椒生物碱富集纯化工艺优化及其成分分析 . 药学实践与服务, 2025, 43(2): 75-81. doi: 10.12206/j.issn.2097-2024.202404066
[2]	江冼芮, 段雅倩, 刘畅, 张成中. 淫羊藿中黄酮苷类化合物的群体感应抑制作用研究 . 药学实践与服务, 2025, 43(): 1-5. doi: 10.12206/j.issn.2097-2024.202409060
[3]	李惠萍, 陈璐, 张琪金, 黄宝康. 紫苏叶挥发油成分的生物合成、含量测定及生物活性研究进展 . 药学实践与服务, 2025, 43(): 1-6. doi: 10.12206/j.issn.2097-2024.202412058
[4]	张紫璇, 高苑, 张利, 李佳莉, 徐希科, 祖先鹏. 中药防治急性肺损伤的活性成分及其作用机制研究进展 . 药学实践与服务, 2025, 43(): 1-7. doi: 10.12206/j.issn.2097-2024.202404079
[5]	施乔, 韩贵焱, 张俊腾, 刘娜. 新型Hsp90抑制剂的设计合成及其抗真菌和抗肿瘤活性研究 . 药学实践与服务, 2025, 43(3): 1-12. doi: 10.12206/j.issn.2097-2024.202501019
[6]	王新霞, 刘祉君, 吕磊, 张爽, 高守红. 鬼针草降压作用研究及展望 . 药学实践与服务, 2025, 43(): 1-4. doi: 10.12206/j.issn.2097-2024.202408021
[7]	周丽城, 欧已铭, 王园. 玉米须黄酮化学成分与药理作用研究进展 . 药学实践与服务, 2025, 43(2): 51-58. doi: 10.12206/j.issn.2097-2024.202309037
[8]	陈方剑, 骆锦前, 王志君, 胡叶帅, 孙煜昕, 宋洪杰. HPLC-MS/MS同时测定感冒安颗粒中5种黄酮成分的含量 . 药学实践与服务, 2024, 42(9): 402-406. doi: 10.12206/j.issn.2097-2024.202403030
[9]	李丹, 戴贤春, 王芳珍, 陈奕含, 杨萍, 刘继勇. HPLC-MS/MS测定当归六黄汤中4种不同成分的含量 . 药学实践与服务, 2024, 42(6): 248-252, 266. doi: 10.12206/j.issn.2097-2024.202305007
[10]	张艺昕, 关欣怡, 王博宁, 闻俊, 洪战英. 二氢吡啶类钙离子拮抗药物手性分析及其立体选择性药动学研究进展 . 药学实践与服务, 2024, 42(8): 319-324. doi: 10.12206/j.issn.2097-2024.202308062
[11]	戴菲菲, 傅翔, 陈琼年, 俞苏纯. 上海某二级医院革兰阴性菌流行特征的回顾性分析 . 药学实践与服务, 2024, 42(12): 528-532. doi: 10.12206/j.issn.2097-2024.202305005
[12]	刘汝雄, 杨万镇, 涂杰, 盛春泉. 铁死亡调控蛋白GPX4的小分子抑制剂研究进展 . 药学实践与服务, 2024, 42(9): 375-378. doi: 10.12206/j.issn.2097-2024.202312075
[13]	张莲卿, 骆岩, 杨提, 姚佳晨, 李文艳. 基于FAERS数据库的艾塞那肽微球不良事件信号挖掘与研究 . 药学实践与服务, 2024, 42(10): 445-450. doi: 10.12206/j.issn.2097-2024.202403057
[14]	赖立勇, 夏天爽, 徐圣焱, 蒋益萍, 岳小强, 辛海量. 中药青蒿抗氧化活性的谱效关系研究 . 药学实践与服务, 2024, 42(5): 203-210, 216. doi: 10.12206/j.issn.2097-2024.202211012
[15]	毛智毅, 王筱燕, 陈晓颖, 汤逸斐. 度拉糖肽联合二甲双胍对肥胖型2型糖尿病患者机体代谢、体脂成分及血清脂肪因子的影响 . 药学实践与服务, 2024, 42(7): 305-309. doi: 10.12206/j.issn.2097-2024.202305032
[16]	陈静, 何瑞华, 翁月, 徐熠, 刘静, 黄瑾. 基于网络药理学和分子对接技术探究定清片活性成分治疗白血病的作用机制 . 药学实践与服务, 2024, 42(11): 479-486. doi: 10.12206/j.issn.2097-2024.202401073
[17]	白学鑫, 陈玉平, 盛春泉, 武善超. 具核梭杆菌小分子抑制剂的筛选及其抗结直肠癌活性研究 . 药学实践与服务, 2024, 42(12): 503-507. doi: 10.12206/j.issn.2097-2024.202405009
[18]	杨媛媛, 安晓强, 许佳捷, 江键, 梁媛媛. 正极性驻极体联合5-氟尿嘧啶对瘢痕成纤维细胞生长抑制的协同作用 . 药学实践与服务, 2024, 42(6): 244-247. doi: 10.12206/j.issn.2097-2024.202310027

点击查看大图

计量

文章访问数: 4127
HTML全文浏览量: 428
PDF下载量: 877
被引次数: 0

姓名
邮箱
手机号码
标题
留言内容
验证码

留言板

中国南海山海绵Mycale sp.的化学成分研究

doi: 10.3969/j.issn.1006-0111.2017.04.006

Study on chemical constituents of sponge Mycale sp. from the South China Sea

计量

中国南海山海绵Mycale sp.的化学成分研究

doi: 10.3969/j.issn.1006-0111.2017.04.006

1. 上海交通大学医学院附属仁济医院药学部, 上海 200127

2. 沈阳药科大学中药学院, 辽宁沈阳 110016

English Abstract

Study on chemical constituents of sponge Mycale sp. from the South China Sea

1. Department of Pharmacy, Renji Hospital Affiliated to School of Medicine, Shanghai JiaoTong University, Shanghai 200127, China

2. School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China

全文HTML

目录

留言板

中国南海山海绵Mycale sp.的化学成分研究

doi: 10.3969/j.issn.1006-0111.2017.04.006

Study on chemical constituents of sponge Mycale sp. from the South China Sea

计量

出版历程

中国南海山海绵Mycale sp.的化学成分研究

doi: 10.3969/j.issn.1006-0111.2017.04.006

1. 上海交通大学医学院附属仁济医院药学部, 上海 200127 2. 沈阳药科大学中药学院, 辽宁 沈阳 110016

English Abstract

Study on chemical constituents of sponge Mycale sp. from the South China Sea

1. Department of Pharmacy, Renji Hospital Affiliated to School of Medicine, Shanghai JiaoTong University, Shanghai 200127, China 2. School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China

全文HTML

目录

1. 上海交通大学医学院附属仁济医院药学部, 上海 200127

2. 沈阳药科大学中药学院, 辽宁沈阳 110016

1. Department of Pharmacy, Renji Hospital Affiliated to School of Medicine, Shanghai JiaoTong University, Shanghai 200127, China

2. School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China