目的 研究红树植物海芒果(Cerbera manghas L)果实的化学成分。方法 利用硅胶柱色谱、制备薄层色谱、Sephadex LH-20凝胶色谱等色谱技术对海芒果果实的体积分数95%乙醇提取物进行分离纯化,根据波谱数据和理化性质对化合物进行结构鉴定。结果 从海芒果果实中分离得到了15个化合物,其中酚酸类化合物11 个,为苯甲酸(benzoic acid, 1),香草酸(vanillic acid, 2),香草醛(vanillin, 3),对羟基苯甲醛(p-hydroxybenzaldehyde, 4),间醛基苯甲酸(isophthalaldehydic acid, 5),β-hydroxypropiovanillone(6),ficusol(7),楝叶吴萸素B(evafolin B, 8),3,4′-dihydroxypropiophenone(9),对羟基苯甲酸(p-hydroxybenzoic acid, 10),原儿茶酸(protocatechuic acid, 11);单萜类化合物1个,为海芒果醛(cerbinal, 12); 强心苷类化合物2个,为17-β-neriifolin(13)、cerberin(14);三萜类化合物1个,为熊果酸(ursolic acid, 15)。结论 除化合物13,14外其他均为首次从海芒果果实中分离得到,化合物5为一新天然产物,化合物1,3,6～9,15为首次从海芒果属植物中分离得到。
Abstract
Objective To investigate the chemical constituents in the fruits of Cerbera manghas Linn.Methods Silica gel column, HPTLC, and Sephadex LH-20 chromatography were applied to isolate the chemical constituents. The structures of the isolated compounds were elucidated by spectroscopic techniques and physicochemical properties. Results Fifteen compounds were isolated and identified including eleven phenolic acids, i.e., benzoic acid(1), vanillic acid(2), vanillin(3), p-hydroxybenzaldehyde(4), isophthalaldehydic acid(5), β-hydroxygpropiovanillone(6), ficusol(7), evofolin B(8), 3,4′-dihydroxypropiophenone(9), p-hydroxybenzoic acid(10), protocatechuic acid(11), one monoterpene, i.e., cerbinal(12), two cardiac glycosides, i.e., 17-β-neriifolin(13) and cerberin(14), and one triterpenoid, i.e., ursolic acid(15). Conclusion All the compounds except compound 13 and 14 are obtained from the fruits for the first time. Compound 5 is a new natural product, and compounds 1, 3, 6-9, and 15 are obtained from genus Cerbera for the first time.
关键词
海芒果 /
酚酸类 /
强心苷 /
单萜 /
三萜
{{custom_keyword}} /
Key words
Cerbera manghas L /
phenolic acid /
monoterpene /
cardiac glycoside /
triterpenoid
{{custom_keyword}} /
中图分类号：
R284
{{custom_clc.code}}
({{custom_clc.text}})
{{custom_sec.title}}
{{custom_sec.title}}
{{custom_sec.content}}
参考文献
[1] WANG Z N, LI H Y, WANG J R, et al. Advances in studies on chemical constituents of Cerbera manghas and their pharmacological activities . Chin Tradit Herb Drugs (中草药), 2009, 40(12): 2011-2012.
[2] DU S J, ZHU W. Progress in study on toxicity of Cerbera manghas and its exploitation . Subtropical Plant Science (亚热带植物学), 2006, 35(4): 79-81.
[3] CHEN R H, PU J, DAI Y Y, et al. Effects of nerifolin,an isolate from seeds of Cerbera manghas L on proliferation and apoptosis of human hepatocellular carcinoma HepG2 cells . Chin J Cancer Biother(中国肿瘤生物治疗杂志), 2011, 18(1): 51-54.
[4] ZHUANG L K, YANG Y, ZHU W. Studies on antifungal activity of Cerbera manghas leaves extraction . Modern Agrochem (现代农药), 2008, 7(5):46-48.
[5] MOORE B S, PORALLA K, FLOSS H G. Biosynthesis of the cyclohexanecarboxylic acid starter unit of w-cyclohexyl fatty acids in alicyclobacillus acidocaldarius . J Am Chem Soc, 1993, 115(1993):5267-5274.
[6] LI H Y, WANG Z N. Study on the chemical constitutents of Cerbera manghas . Haikou: Univ. of Hainan, 2010.
[7] ZHENG Z, PEI Y H. Study on the chemical constitunts of Sonneratia ovata from south China sea . Shenyang: Univ. of Shenyang pharm, 2007.
[8] ZHANG X P, PEI Y H, LIU M S, et al. Chemical constituents from the leaves of Cerbera manghas . Asian Pacific J Trop Med, 2010,(1):109-111.
[9] SIMONIS H. Aromatic aldehyde acids . Bericht Deut Chem Gesellschaft, 1912,(7):1584-1592.
KARONEN M, HAMAAINEN M, NIEMINEN R, et al. Phenolic extractives from the bark of Pinus sylvestris L.and their effects on inflammatory mediators nitric oxide and prostaglandin E2. J Agric Food Chem, 2004, 52(25): 7532-7540.
LI Y C, KUO Y H. A monoterpenoid and two simple phenols from heartwood of Ficus microcarpa . Phytochemistry, 1998, 49(8): 2417-2419.
WU T S, YEH J H, WU P L. The heartwood constituents of Tetradium glabrifolium . Phytochemisry, 1995, 40(1): 121-124.
GAO G C, TAO S H, QI S H, et al. Study on the chemical constitunts of Catunar egam spinosa(П) . Chin Tradit Herb Drugs (中草药), 2010, 41(4): 539-541.
RUDOLF T, ARTUR H, GUENTER W. 3,4′-Dihydroxypropiophenone -3-β-D- glucopyranoside from Betula alba . Phytochemistry, 1974, 13(2): 518-519.
O′CONNOR C J, MCLENNAN D J, CULVERT D J, et al. Substituent effects on the N.M.R. spectra of carboxylic acid derivatives.IV13C-NMR spectra of para-substituted phenols, phenylureas and phenyl propionates . Aust J Chem, 1987, 40:677-686.
LI X, ZHANG Y F, YANG L, et al. Studies of phenolic acid constituents from the whole plant of Sarcandra glabra . Tradit Chin Drug Res Clin Pharm(中药新药与临床药理), 2012, 23(3): 295-298.
ZHANG X P, ZHANG J Q, LIU M S, et al. Study on the chemical constitunts of stem and bark from Cerbera manghas . Chin Tradit Herb Drugs (中草药), 2008, 39(8): 1138-1140.
YAMAUCHI T, ABE F, WAN A S C. Cardenolide monoglycosides from the leaves of Cerbera odollam and Cerbera manghas(Cerbera. III). Chem Pharm Bull, 1987, 35: 2744-2749.
ZHENG Z, PEI Y H. Chemical constitunts from Sonneratia ovata . J Shenyang Pharm Univ (沈阳药科大学学报), 2008, 25(1): 35-38.
{{custom_fnGroup.title_cn}}
脚注
{{custom_fn.content}}
PDF(608 KB)
