红树植物无瓣海桑果实的化学成分研究

doi:10.11978/j.issn.1009-5470.2015.01.011

热带海洋学报 ›› 2015, Vol. 34 ›› Issue (1): 77-82.doi: 10.11978/j.issn.1009-5470.2015.01.011CSTR: 32234.14.j.issn.1009-5470.2015.01.011

红树植物无瓣海桑果实的化学成分研究

曹雷雷^{1, 2}, 田海妍², 王友绍³, 周雪峰¹, 江仁望², 刘永宏¹

1. 中国科学院南海海洋研究所, 广东省海洋药物重点实验室, 广东广州 510301;
2. 暨南大学药学院, 中药及天然药物研究所, 广东省高校重点实验室, 广东广州 510632;
3.中国科学院南海海洋研究所, 大亚湾海洋生物综合实验站, 广东深圳 518121

收稿日期:2013-06-24 修回日期:2014-07-22 出版日期:2015-02-10 发布日期:2015-02-10
作者简介:曹雷雷(1987~), 男, 陕西省宝鸡市人, 硕士研究生, 研究方向为中药及天然药物活性成分研究。E-mail: caoleilei222@163.com
基金资助:
国家自然科学基金资助项目(31270402)

Chemical constituents in the fruits of mangrove plant Sonneratia apetala Buch. Ham.

CAO Lei-lei, TIAN Hai-yan, WANG You -shao, ZHOU Xue-feng, JIANG Ren-wang, LIU Yong-hong

1. Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China;
2. Guangdong Province Key Laboratory, Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou 510632, China;
3. Marine Biology Research Station at Daya Bay, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Shenzhen518121, China

Received:2013-06-24 Revised:2014-07-22 Online:2015-02-10 Published:2015-02-10
Contact: 刘永宏(1972~), 男, 博导, 研究员, 研究方向为海洋天然产物化学。E-mail: yonghongliu@scsio.ac.cn

摘要/Abstract

摘要： 采用多种色谱和波谱技术从无瓣海桑(Sonneratia apetala Buch. Ham)果实的95%乙醇提取物中共分离鉴定了16个化合物(1~16a/16b)。其中, 甾醇类化合物1个, β-谷甾醇 (β-sitosterol, 1); 三萜类化合物1个, 白桦脂酸 (betulinic acid, 2); 酚酸类化合物8个, 顺式异扁柏脂素 (cis-hinkiresinol, 3)、4°-甲氧基顺式异扁柏脂素 (4°-O-methyl-cis-hinokiresinol, 4)、香草酸 (vanillic acid, 5)、没食子酸甲酯 (methyl gallate, 6)、3-甲氧基没食子酸 (3-O-methyl gallic acid, 7)、丁香醛 (syringaldehyde, 8)、丁香酸 (syringic acid, 9)、对羟基苯甲酸甲酯 (methylparaben, 10); 苹果酸酯类化合物9个, 4-ethoxy- 3-hydroxy-4-oxobutanoic acid (11)、苹果酸二甲酯 (dimethyl malate, 12)、苹果酸甲基乙基酯 (ethylmethyl malate, 13a/13b)、苹果酸乙基正丁基酯(butylethyl malate, 14a/14b)、苹果酸二正丁基酯 (bibutyl malate, 15)、苹果酸甲基正丁基酯 (butylmethyl malate, 16a/16b)。化合物14a/14b为新化合物; 化合物11为新天然产物; 化合物3~16a/16b为首次从无瓣海桑植物中分离得到; 化合物3、5~16a/16b为首次从海桑属植物中分离得到。

关键词: 无瓣海桑, 三萜, 酚酸类, 苹果酸酯, 化学成分

Abstract: A total of 95% ethanol extract from the fruits of Sonneratia apetala Buch. Ham was isolated by a variety of chromatographic methods, and the structures of the isolated compounds (1~16a/16b) were elucidated by a series of spectroscopic techniques. These structures were identified, including one phytosterols, β-sitosterol (1); one triterpenoid, (betulinic acid, 2); eight phenolic acids, cis-hinkiresinol (3), 4°-O-methyl-cis-hinokiresinol (4), vanillic acid (5), methyl gallate (6), 3-O-methyl gallic acid (7), syringaldehyde (8), syringic acid (9), methylparaben (10); and nine malate compounds, 4-ethoxy-3-hydroxy-4-oxobutanoic acid (11), dimethyl malate (12), ethylmethyl malate (13a/13b), butylethyl malate (14a/14b), bibutyl malate (15), butylmethyl malate (16a/16b). The compounds 14a/14b were new; compound 11 was a new natural product; the compounds 3~16a/16b were obtained from S. Apetala for the first time; and the compounds 3, 5~16a/16b were obtained from genus Sonneratia for the first time.

Key words: Sonneratia apetala Buch. Ham, triterpenoid, phenolic acids, malate, chemical constituents

曹雷雷, 田海妍, 王友绍, 周雪峰, 江仁望, 刘永宏. 红树植物无瓣海桑果实的化学成分研究[J]. 热带海洋学报, 2015, 34(1): 77-82.

CAO Lei-lei^{1, 2}, TIAN Hai-yan², WANG You -shao³, ZHOU Xue-feng¹, JIANG Ren-wang², LIU Yong-hong¹. Chemical constituents in the fruits of mangrove plant Sonneratia apetala Buch. Ham.[J]. Journal of Tropical Oceanography, 2015, 34(1): 77-82.

参考文献

[1] .纪卿飞, 林文翰, 李军, 等. 2005. 中国红树林植物-无瓣海桑的化学成分研究[J]. 中国中药杂志, 30(16): 1258-1260.
[2] .李海燕, 王祝年. 2010. 海杧果化学成分研究[D]. 海口: 海南大学: 31-32.
[3] .徐文, 周光雄. 2009. 木荷的化学成分研究[D]. 广州: 暨南大学: 23-25.
[4] .杨文强, 张晓琦. 2012. 槟榔与五倍子的化学成分研究[D]. 广州: 暨南大学: 43-44.
[5] .郑吉吉, 裴月湖. 2007. 中国南海红树林植物卵叶海桑的化学成分研究[D]. 沈阳: 沈阳药科大学: 27-28.
[6] .DIAS C, DIAS M, BORGES C, et al. 2003. Structural elucidation of natural 2-hydroxy di- and tricarboxylic acids and esters, phenylpropanoid esters and a ?avonoid from Autonoe madeirensis using gas chromatographic/electron ionization, electrospray ionization and tandem mass spectrometric techniques[J]. J Mass Spectrom, 38: 1240-1244.
[7] .FAN X M, CHEN G, SU S S, et al. 2011. Isolation and identification of constituents from fruit of Trichosanthes kirilowii Maxim [J]. Shenyang Yaoke Daxue Xuebao, 28(12): 947-948.
[8] .MILLERM J, BAJWA J S, MATTINGLY P G. 1982. Enantioselective syntheses of 3-substituted (alkoxycarbonyl)- 2-azetidinones from malic acid[J]. J Org Chem, 47: 4928-4933.
[9] .NAIK K M, NANDIBEWOOR S T. 2013. Spectral characterization of the binding and conformational changes of bovine serum albumin upon interaction with an anti-fungal drug, methylparaben[J]. Spectrochim Acta A: Mol Biomol Spectrosc, 105: 418-423.
[10] .SAMOYLENKO V, ZHAO J, DUNBAR D C, et al. 2006. New constituents from Noni (Morindacitrifolia) fruit juice[J]. J Agric Food Chem, 54: 6398-6402.
[11] .SUN Q, SUN A, LIU R. 2006. Preparative isolation and puriﬁcation of four compounds from the Chinese medicinal herb Rhizoma Anemarrhenae by high-speed counter-current chromatography[J]. J Chromatogr A, 1104: 69-74.
[12] .XING R, WU L, FEI Z, et al. 2013. Palladium phthalocyaninesulfonate functionalized mesoporous polymer: A highly efficient photocatalyst for degradation of 4-chlorophenol under visible light irradiation[J]. J Mol Catal A: Chem, 371: 15-20.
[13] .YANG Y, LIU Z, FENG Z, et al. 2012. Lignans from the root of Rhodiola crenulata [J]. J Agric Food Chem, 60: 964-972.

红树植物无瓣海桑果实的化学成分研究

Chemical constituents in the fruits of mangrove plant Sonneratia apetala Buch. Ham.

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