红树植物红海榄系列化学组分分析及生物活性研究
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摘要
红树植物(Mangrove plants)是热带、亚热带红树林区特有的潮间带高等木本植物,也是世界上珍稀濒危的植物之一,不仅具有很高的观赏和科考价值,而且还具有抵御风浪、保护海岸、降解污染、调节气候、维持海洋生物多样性等非常重要的生态功能。目前国内外对红树林的研究主要围绕在生态学、生态生理学、植物分类学、群落分布等方面,而有关某种红树植物的化学组分和生物活性的研究相对零散。由于红树植物化学组分的构成与生态环境之间存在着一定的内在联系,为了揭示红树植物化学组成规律,进一步研究红树植物自身代谢产物与环境之间的相互关系、维系良好的海岸生态环境以及保护和科学合理利用红树植物资源提供科学参考,本文以在广东湛江分布较广的代表性红树植物红海榄(Rhizophora stylosa Griff.)为研究对象,采用多种交叉学科手段,较系统地分析测定了红海榄基本化学成分(水分、灰分、酸不溶物、S、粗蛋白、粗脂肪)、微量元素、蛋白氨基酸、水解氨基酸梅拉德反应产物、挥发油、脂肪酸、多糖和黄酮类化合物等系列化学组分的构成和含量,并研究了其黄酮提取物的体外抑菌活性、抗肿瘤活性和枯萎叶中镰刀菌酸毒素与Cu~(2+)配合物的结构及其抗肿瘤活性。
本文研究工作及结果如下:
1.对红树植物红海榄叶的基本化学成分进行了测定,测得各基本化学成分的含量分别为:水分(69.18%)、灰分(3.04%)、酸不溶物(0.094%)、S(以SO_4~(2-)计)(0.052%)、粗蛋白(7.91%)和粗脂肪(7.41%)。红海榄各基本化学成分与陆生植物存在不同程度的差异性。
2.采用电感耦合等离子体原子发射光谱法(ICP-AES)对红海榄叶和果实的13种微量元素(Al、As、Ba、Cd、Cr、Cu、Fe、Mn、Ni、Pb、Sr、Ti、Zn)进行了含量测定。其中Zn、Fe、Cu在红海榄叶中含量较高,Zn、Fe、Cr在红海榄果实中含量较高。发现锌在两者所测得的微量元素中含量均最高,叶中达183.0mg/kg,果实中达218.4mg/kg。两者含锌量均远高于常见陆生粮油作物。
3.采用高效液相色谱法测得了红海榄叶中含有17种蛋白氨基酸,其总含量为10.7g/kg,其中人体必需氨基酸有7种(Thr、Val、Met、Ile、Leu、Phe、Lys),占所含蛋白氨基酸总量的25.75%;其中含量最高的为天门冬氨酸,达2.69g/kg。采用离子交换色谱-积分脉冲安培法(HPIC-IPAD)测得红海榄果实中含有14种氨基酸,其总含量为149g/kg,其中6种为人体的必需氨基酸,占氨基酸总量的46.15%,8种为非必需氨基酸。其中谷氨酸、苯丙氨酸、精氨酸、缬氨酸含量较高,分别为36.56g/kg、34.42g/kg、22.33g/kg、15.47g/kg。
4.将红海榄叶经水解所得混合氨基酸分别与葡萄糖和蔗糖在105～108℃下反应6h,得梅拉德反应产物。用乙醚为溶剂萃取出产物中的醚溶性成分,再利用气相色谱—质谱联用仪(GC-MS)对醚溶性成分进行分离和鉴定,各鉴定出9种化合物。两种组分既有相似性又有差异性,产物都有致香物质存在。表明非还原性蔗糖也可以发生梅拉德反应。
5.采用水蒸气蒸馏法提取红海榄叶和果实挥发油,再利用GC-MS进行分析检测。结果表明,从红海榄叶挥发油中共分离出40种化合物,鉴定出31种,占挥发油含量的83.62%,其中含量最高的是BHT。4-羟基-2-甲基苯甲酸甲酯、四十一醇、2,6,10,15,19,23-六甲基二十四烷首次在该植物叶中发现。从红海榄果实挥发油中共分离出29种化合物,鉴定出29种,其中3-甲氧基-1,2-丙二醇含量最高,占挥发油相对含量的26.39%。其中N-N'-二苯甲酰氧基庚二酰氨、2,3-二氢苯并呋喃、一氢咪唑-2-甲醛、榄香素、3,7,11-三甲基-1,6,10十二碳三烯-3-醇、2,8-二甲基-4,6-壬二酮等首次在该植物果实中发现。
6.利用索氏提取法对红海榄叶和果实中的脂肪酸进行提取,得率分别为3.272%和2.530%。甲酯化后利用GC-MS对脂肪酸成分进行分离和鉴定。结果从红海榄叶中鉴定出12种脂肪酸,占脂肪酸提取物总量的84.95%,其中主要包括十六酸(棕榈酸)(40.49%),9-十八碳烯酸(油酸)(17.24%)和9,12-十八碳二烯酸(亚油酸)(11.14%)等;从红海榄果实中鉴定出8种脂肪酸,其中棕榈酸、8,11,14-二十碳三烯酸、亚油酸的含量较高,分别占脂肪酸提取物总量的7.59%、4.25%、3.22%。叶中不饱和脂肪酸(UFA)和饱和脂肪酸(SFA)的相对含量均远高于果实,但UFA与SFA的比值叶低于果实。并首次发现在果实中存在8,11,14-二十碳三烯酸。
7.从红海榄叶中提取出多糖,多糖的得率为2%。用溴化钾压片法进行红外光谱测试,红外光谱分析表明红海榄多糖具有杂多糖的特征;再通过完全酸水解、糖腈乙酸酯衍生化以及GC-MS分析,得出此多糖由赤藓糖、D-阿拉伯糖以及葡萄糖组成。结果表明红海榄多糖属杂多糖。
8.采用醇提法提取红海榄叶中的黄酮,所得黄酮粗提物分离纯化得针状晶体,通过理化性质及UV、IR、MS、元素分析等综合分析鉴定,证实该晶体为芦丁,其分子式为C_(27)H_(30)O_(16),分子量为610.5。采用紫外分光光度法测定了红海榄叶黄酮粗提物中总黄酮的含量为58.29%。
9.采用平板打孔扩散法研究了红海榄叶黄酮提取液对金黄色葡萄球菌(Staphylococcus aureus)、大肠杆菌(Escherichia coli)、立枯丝核菌(Rhizotonia solani)、香蕉炭疽菌(Colletotrichum musae)、香蕉枯萎病菌(Fusarium oxysporum f.sp.cubense)、黄瓜枯萎病菌(F.f sp Cucumerinum)、富贵竹炭疽菌(Colletotrichum sp.)和黑曲霉(Aspergillus niger)八种菌的体外抑菌活性。结果表明:红海榄叶黄酮提取液对细菌和植物病原真菌有不同程度的抑制作用,对大肠杆菌、香蕉枯萎菌和香蕉炭疽菌有明显的抑菌效果,对富贵竹炭疽菌、立枯丝核菌和金黄色葡萄球菌有较弱的抑制效果,而对黄瓜枯萎病菌和黑曲霉无明显的抑菌效果。采用打孔法测定了红海榄黄酮提取液对抑菌效果较好的大肠杆菌、香蕉枯萎菌和香蕉炭疽菌的最低抑菌浓度(MIC),红海榄黄酮提取液对香蕉枯萎菌和香蕉炭疽菌的MIC较小。
10.为了对红海榄黄酮提取物体外抗肿瘤活性进行评价,以人肝癌细胞NCI-H460为对象,采用MTT法做了红海榄黄酮提取物体外抗肿瘤活性实验,结果表明,红海榄黄酮提取物对人肝癌细胞NCI-H460的生长有较好的抑制活性。
11.从红海榄枯萎叶的镰刀菌酸粗提物中,采用“单晶诱导法”,用Cu~(2+)诱导镰刀菌酸与铜离子配位形成单晶体,再利用X-单晶衍射仪对其结构进行测试和表征,结果表明该配合物为Cu(C_(10)H_(12)NO_2)_2,其晶体属三斜晶系,空间群为P(?),晶胞参数为a=5.50520(10)(?),b=8.0683(3)(?),c=11.3008(5)(?),α=70.338(3)°,β=89.399(2)°,γ=78.7060(10)°。V=462.70(3)(?)~3,Z=1,M_r=419.95,D_x=1.507mg·m~(-3),μ=1.020mm~(-1),F(000)=219,最终R=0.040,wR=0.107。证实了该配合物的配体是镰刀菌酸(C_(10)H_(13)NO_2)。从而确定了枯萎叶中含有镰刀菌酸。通过体外抗肿瘤活性实验,首次发现镰刀菌酸铜配合物对人肝癌BEL-7402细胞的生长有较好的抑制活性。
Mangrove plants are higher woody plants especially growing on the tidal flat of tropical and sub-tropical mangrove.They are one of rare or endangered species in the world.Mangrove plants not only have great ornamental value and scientific research value, but also play an important role in defending coastline against the strong wind and big waves,degradating pollution,regulating climate,keeping marine biodiversity,and so on. Many studies on mangroves have been mainly focused on ecology,ecological physiology, plant taxonomy and ecological community.However,there are only a few scattered studies on chemical composition and biological activities of a certain mangrove plant.Because there are some internal connections between what comprises the mangrove plant and the ecosystem environment it grows in.In order to reveal internal laws of chemical composition of mangrove plants to provide a scientific basis for further research on relationship between metabolites and the environment,preserving good ecosystem environment and protection and rational use of mangrove plant resources,the representative mangrove plant of Rhizophora stylosa,collected from Zhanjiang, Guangdong,China,was elected as subject.The contents of moisture,ash,acid infusible ash, sulphide,crude proteins and crude fats,trace elements,protein amino acids,the Maillard reaction products from the hydrolyzed amino acids,volatile oils,fatty acids, ploysaccharides and flavones were more systemically determined and analyzed. Meanwhile,inhibitory effect and anti-tumor activity of flavonoids extract in Rhizophora stylosa leaves and anti-tumor activity of the complex of Cu~(2+) and fusarium wilt toxins from blasted leaves of Rhizophora stylosa were studied.
Main studies and conclusions summarized as follows:
1.The basic chemical composition of leaves from Rhizophora stylosa were studied. The percentage contents of moisture,ash,acid infusible ash,sulphide,crude proteins and crude fats in leaves of Rhizophora stylosa were 69.18%,3.04%,0.094%,0.052%,7.91% and 7.41%respectively.Each of them is different from some terrestrial plants in varying degrees.
2.Thirteen elements of A1,As,Ba,Cd,Cr,Cu,Fe,Mn,Ni,Pb,Sr,Ti and Zn of the leaves and fruits of Rhizophora stylosa were analyzed by ICP-AES.And the contents of the elements of them were determined.Zn,Fe,Cu and Zn,Fe,Cr are the comparatively rich elements in the leaves and fruits of Rhizophora stylosa respectively.The content of Zn, amounting to 183.0 mg/kg in the leaves and 218.4 mg/kg in the fruits,is the highest among the trace elements determined.The content of zinc in both of them are far more than common oil-bearing crops.
3.Seventeen protein amino acids in leaves of Rhizophora stylosa with total content of 10.7g/kg were determined by HPLC,seven among which are essential amino acids, amounting to 25.75%of the total amino acids.They are Thr,Val,Met,Ile,Leu,Phe and Lys.Asp,amounting to 2.69 g/kg,was determined as the optimum amino acid.Forteen protein amino acids in fruits of Rhizophora stylosa with total content of 149g/kg were determined by HPIC-IPAD,six among which are essential amino acids,amounting to 46.15%of the total amino acids.And eight among which are unessential amino acids.The content of Glu,Phe,Arg and Val,amounting to 36.56g/kg,34.42g/kg,22.33g/kg and 15.47g/kg respectively were determined as the optimum amino acids.
4.The Maillard reaction products were obtained from the reaction of complex amino acids from leaves of Rhizophora stylosa hydrolysised by concentrated hydrochloric acid and glucose and sucrose for six hours under the temperature between degree centigrade 105 and 108 respectively.The ether-soluble materials from the reaction product were extracted by ethyl ether and determined by GC-MS.There are some different components in both of the nine components.Both products have aromatic substances.The results presented that Maillard reactions can take place by sucrose without reductive character.
5.The volatile oils from the leaves and fruits of mangrove plant Rhizophora stylosa were extracted by steam distillation and analyzed by GC-MS.Thirty-one volatile compounds in forty one separated from leaves of Rhizophora stylosa were identified, which accounted for 83.62%of the total volatile oil.BHT was determined as the optimum composition.2-Hydroxy-4-methylbenzoate,hentetracontyl alcohol and 2,6,10,15,19,23-hexamethyl tetracosane were discovered for the first time in the volatile oils from the leaves of Rhizophora stylosa.And all the volatile compositions separated from fruits of Rhizophora stylosa were identified,among which,3-Methoxy-1,2-propanediol,taking the proportion of 26.39%,was determined as the optimum composition.The six compounds of N,N'-di-benzoyloxy heptanediamide,2,3-Dihydro-benzofuran,1H-Imidazole-2-carboxaldehyde, Elemicin,3,7,11-Trimethyl-1,6,10-Dodecatrien-3-ol and 2,8-Dimethyl-4,6-nonanedione were discovered for the first time in the volatile oils from the fruits of mangrove plant Rhizophora stylosa.
6.The fatty acids,with the yield of 3.272%and 2.530%respectively,were extracted by Soxhlet extraction from the leaves and the fruits of mangrove plant Rhizophora stylosa. The extracted fatty acids were esterified and analyzed by gas chromatography-mass spectrometry.Twelve fatty acids were detected and identified,amounting to 84.95%of the total fatty acids from the leaves of Rhizophora stylosa.The compounds mainly includ palmitic acid(40.49%),oleic acid(17.24%) and linoleic acid(11.14%).Eight fatty acids, mainly including palmitic acid,8,11,14-eicosatrienoic acid and linoleic acid,respectively amounting to 7.59%,4.25%and 3.22%were identified from the fruits of Rhizophora stylosa.And 8,11,14-eicosatrienoic acid was discovered for the first time.
7.The polysaccharide,with the yield of 2%,was extracted from Rhizophpra stylosa leaves.And the polysaccharide extracted was tested and analyzed by IR.The IR spectrum indicates that there are characteristic absorption peaks of polysaccharides.Analyses by complete acid hydrolysis and aldoononitrile acetate derivatives and GC-MS indicated that it is composed of erythrose,D-arabinose and glucose.The results presented that the polysaccharide from Rhizophpra stylosa belongs to heteropolysaccharide.
8.The extract of crud flavonoids in Rhizophora stylosa leaves were extracted by ethanol and then separated and purified by extraction,polyamide packed chromatography and crystallization and needle crystal compound separated out.The needle crystal compound was identified structurally by UV,IR,MS and element analyzing combined with physical and chemical property as rutin.The molecular formula of Rhizophora stylosa rutin is C_(27)H_(30)O_(16) and its molecular weight is 610.5.The total flavonoids content of the crude flavonoids extract was determined as 58.29%by UV-spectrophotometry.
9.The in vitro antimicrobial activity experiments of total flavonoids extract from the mangrove plant Rhizophora stylosa were studied by the plate diluting method.The results presented that the total flavonoids extract had varied inhibitory effects on the bacteria and plant pathogenic fungi.The extract was more distinctly sensitive to Escherichia coli, Colletotrichum musae and Fusarium oxysporum f.sp.cubense,and less to Colletotrichum sp.,Rhizotonia solani and Staphylococcus aureus and no to Aspergillus niger.The minimal inhibitory concentrations(MIC) were determined by plate diluting method.
10.To evaluate anti-tumor activity of flavonoid extraction from Rhizophora stylosa, the anti-tumor activity of flavonoid extraction from Rhizophora stylosa against human lung cancer cell NCI-H460 were determined by MTT method.The result of the anti-tumor experiment presented that the flavonoid extraction from Rhizophora stylosa showed significant anti-tumor activity on human lung cancer cell NCI-H460 in vitro.
11.A single crystal was obtained from the wilt leaves of Rhizophora stylosa by crystal induction method with Cu~(2+).The single crystal's structure information and the crystal data were present by X-Ray difference reflection technology.The single crystal belongs to the triclinic system with the molecular formula of Cu(C_(10)H_(12)NO_2)_2.It's space group is PI and the crystal data presented as follows:a=5.50520(10),(?),b=8.0683(3)(?), c=11.3008(5)(?),α=70.338(3)°,β=89.399(2)°,γ=78.7060(10)°,V=462.70(3)(?)~3,Z=1, M_r=419,95,D_x=1.507mg·m~(-3),μ=1.020mm~(-1),F(000)=219,R=0.040,wR=0.107.It is proved that a ligand of the obtained complex is fusaric acid(C_(10)H_(13)NO_2).Then it is concluded the one of the reasons of the phenomenon is fusaric acid.The result of the anti-tumor experiment presented that the complex of fusaric acid and Cu~(2+) showed significant anti-tumor activity on human hepatoma cells BEL-7402 in vitro.
本文研究工作及结果如下:
1.对红树植物红海榄叶的基本化学成分进行了测定,测得各基本化学成分的含量分别为:水分(69.18%)、灰分(3.04%)、酸不溶物(0.094%)、S(以SO_4~(2-)计)(0.052%)、粗蛋白(7.91%)和粗脂肪(7.41%)。红海榄各基本化学成分与陆生植物存在不同程度的差异性。
2.采用电感耦合等离子体原子发射光谱法(ICP-AES)对红海榄叶和果实的13种微量元素(Al、As、Ba、Cd、Cr、Cu、Fe、Mn、Ni、Pb、Sr、Ti、Zn)进行了含量测定。其中Zn、Fe、Cu在红海榄叶中含量较高,Zn、Fe、Cr在红海榄果实中含量较高。发现锌在两者所测得的微量元素中含量均最高,叶中达183.0mg/kg,果实中达218.4mg/kg。两者含锌量均远高于常见陆生粮油作物。
3.采用高效液相色谱法测得了红海榄叶中含有17种蛋白氨基酸,其总含量为10.7g/kg,其中人体必需氨基酸有7种(Thr、Val、Met、Ile、Leu、Phe、Lys),占所含蛋白氨基酸总量的25.75%;其中含量最高的为天门冬氨酸,达2.69g/kg。采用离子交换色谱-积分脉冲安培法(HPIC-IPAD)测得红海榄果实中含有14种氨基酸,其总含量为149g/kg,其中6种为人体的必需氨基酸,占氨基酸总量的46.15%,8种为非必需氨基酸。其中谷氨酸、苯丙氨酸、精氨酸、缬氨酸含量较高,分别为36.56g/kg、34.42g/kg、22.33g/kg、15.47g/kg。
4.将红海榄叶经水解所得混合氨基酸分别与葡萄糖和蔗糖在105～108℃下反应6h,得梅拉德反应产物。用乙醚为溶剂萃取出产物中的醚溶性成分,再利用气相色谱—质谱联用仪(GC-MS)对醚溶性成分进行分离和鉴定,各鉴定出9种化合物。两种组分既有相似性又有差异性,产物都有致香物质存在。表明非还原性蔗糖也可以发生梅拉德反应。
5.采用水蒸气蒸馏法提取红海榄叶和果实挥发油,再利用GC-MS进行分析检测。结果表明,从红海榄叶挥发油中共分离出40种化合物,鉴定出31种,占挥发油含量的83.62%,其中含量最高的是BHT。4-羟基-2-甲基苯甲酸甲酯、四十一醇、2,6,10,15,19,23-六甲基二十四烷首次在该植物叶中发现。从红海榄果实挥发油中共分离出29种化合物,鉴定出29种,其中3-甲氧基-1,2-丙二醇含量最高,占挥发油相对含量的26.39%。其中N-N'-二苯甲酰氧基庚二酰氨、2,3-二氢苯并呋喃、一氢咪唑-2-甲醛、榄香素、3,7,11-三甲基-1,6,10十二碳三烯-3-醇、2,8-二甲基-4,6-壬二酮等首次在该植物果实中发现。
6.利用索氏提取法对红海榄叶和果实中的脂肪酸进行提取,得率分别为3.272%和2.530%。甲酯化后利用GC-MS对脂肪酸成分进行分离和鉴定。结果从红海榄叶中鉴定出12种脂肪酸,占脂肪酸提取物总量的84.95%,其中主要包括十六酸(棕榈酸)(40.49%),9-十八碳烯酸(油酸)(17.24%)和9,12-十八碳二烯酸(亚油酸)(11.14%)等;从红海榄果实中鉴定出8种脂肪酸,其中棕榈酸、8,11,14-二十碳三烯酸、亚油酸的含量较高,分别占脂肪酸提取物总量的7.59%、4.25%、3.22%。叶中不饱和脂肪酸(UFA)和饱和脂肪酸(SFA)的相对含量均远高于果实,但UFA与SFA的比值叶低于果实。并首次发现在果实中存在8,11,14-二十碳三烯酸。
7.从红海榄叶中提取出多糖,多糖的得率为2%。用溴化钾压片法进行红外光谱测试,红外光谱分析表明红海榄多糖具有杂多糖的特征;再通过完全酸水解、糖腈乙酸酯衍生化以及GC-MS分析,得出此多糖由赤藓糖、D-阿拉伯糖以及葡萄糖组成。结果表明红海榄多糖属杂多糖。
8.采用醇提法提取红海榄叶中的黄酮,所得黄酮粗提物分离纯化得针状晶体,通过理化性质及UV、IR、MS、元素分析等综合分析鉴定,证实该晶体为芦丁,其分子式为C_(27)H_(30)O_(16),分子量为610.5。采用紫外分光光度法测定了红海榄叶黄酮粗提物中总黄酮的含量为58.29%。
9.采用平板打孔扩散法研究了红海榄叶黄酮提取液对金黄色葡萄球菌(Staphylococcus aureus)、大肠杆菌(Escherichia coli)、立枯丝核菌(Rhizotonia solani)、香蕉炭疽菌(Colletotrichum musae)、香蕉枯萎病菌(Fusarium oxysporum f.sp.cubense)、黄瓜枯萎病菌(F.f sp Cucumerinum)、富贵竹炭疽菌(Colletotrichum sp.)和黑曲霉(Aspergillus niger)八种菌的体外抑菌活性。结果表明:红海榄叶黄酮提取液对细菌和植物病原真菌有不同程度的抑制作用,对大肠杆菌、香蕉枯萎菌和香蕉炭疽菌有明显的抑菌效果,对富贵竹炭疽菌、立枯丝核菌和金黄色葡萄球菌有较弱的抑制效果,而对黄瓜枯萎病菌和黑曲霉无明显的抑菌效果。采用打孔法测定了红海榄黄酮提取液对抑菌效果较好的大肠杆菌、香蕉枯萎菌和香蕉炭疽菌的最低抑菌浓度(MIC),红海榄黄酮提取液对香蕉枯萎菌和香蕉炭疽菌的MIC较小。
10.为了对红海榄黄酮提取物体外抗肿瘤活性进行评价,以人肝癌细胞NCI-H460为对象,采用MTT法做了红海榄黄酮提取物体外抗肿瘤活性实验,结果表明,红海榄黄酮提取物对人肝癌细胞NCI-H460的生长有较好的抑制活性。
11.从红海榄枯萎叶的镰刀菌酸粗提物中,采用“单晶诱导法”,用Cu~(2+)诱导镰刀菌酸与铜离子配位形成单晶体,再利用X-单晶衍射仪对其结构进行测试和表征,结果表明该配合物为Cu(C_(10)H_(12)NO_2)_2,其晶体属三斜晶系,空间群为P(?),晶胞参数为a=5.50520(10)(?),b=8.0683(3)(?),c=11.3008(5)(?),α=70.338(3)°,β=89.399(2)°,γ=78.7060(10)°。V=462.70(3)(?)~3,Z=1,M_r=419.95,D_x=1.507mg·m~(-3),μ=1.020mm~(-1),F(000)=219,最终R=0.040,wR=0.107。证实了该配合物的配体是镰刀菌酸(C_(10)H_(13)NO_2)。从而确定了枯萎叶中含有镰刀菌酸。通过体外抗肿瘤活性实验,首次发现镰刀菌酸铜配合物对人肝癌BEL-7402细胞的生长有较好的抑制活性。
Mangrove plants are higher woody plants especially growing on the tidal flat of tropical and sub-tropical mangrove.They are one of rare or endangered species in the world.Mangrove plants not only have great ornamental value and scientific research value, but also play an important role in defending coastline against the strong wind and big waves,degradating pollution,regulating climate,keeping marine biodiversity,and so on. Many studies on mangroves have been mainly focused on ecology,ecological physiology, plant taxonomy and ecological community.However,there are only a few scattered studies on chemical composition and biological activities of a certain mangrove plant.Because there are some internal connections between what comprises the mangrove plant and the ecosystem environment it grows in.In order to reveal internal laws of chemical composition of mangrove plants to provide a scientific basis for further research on relationship between metabolites and the environment,preserving good ecosystem environment and protection and rational use of mangrove plant resources,the representative mangrove plant of Rhizophora stylosa,collected from Zhanjiang, Guangdong,China,was elected as subject.The contents of moisture,ash,acid infusible ash, sulphide,crude proteins and crude fats,trace elements,protein amino acids,the Maillard reaction products from the hydrolyzed amino acids,volatile oils,fatty acids, ploysaccharides and flavones were more systemically determined and analyzed. Meanwhile,inhibitory effect and anti-tumor activity of flavonoids extract in Rhizophora stylosa leaves and anti-tumor activity of the complex of Cu~(2+) and fusarium wilt toxins from blasted leaves of Rhizophora stylosa were studied.
Main studies and conclusions summarized as follows:
1.The basic chemical composition of leaves from Rhizophora stylosa were studied. The percentage contents of moisture,ash,acid infusible ash,sulphide,crude proteins and crude fats in leaves of Rhizophora stylosa were 69.18%,3.04%,0.094%,0.052%,7.91% and 7.41%respectively.Each of them is different from some terrestrial plants in varying degrees.
2.Thirteen elements of A1,As,Ba,Cd,Cr,Cu,Fe,Mn,Ni,Pb,Sr,Ti and Zn of the leaves and fruits of Rhizophora stylosa were analyzed by ICP-AES.And the contents of the elements of them were determined.Zn,Fe,Cu and Zn,Fe,Cr are the comparatively rich elements in the leaves and fruits of Rhizophora stylosa respectively.The content of Zn, amounting to 183.0 mg/kg in the leaves and 218.4 mg/kg in the fruits,is the highest among the trace elements determined.The content of zinc in both of them are far more than common oil-bearing crops.
3.Seventeen protein amino acids in leaves of Rhizophora stylosa with total content of 10.7g/kg were determined by HPLC,seven among which are essential amino acids, amounting to 25.75%of the total amino acids.They are Thr,Val,Met,Ile,Leu,Phe and Lys.Asp,amounting to 2.69 g/kg,was determined as the optimum amino acid.Forteen protein amino acids in fruits of Rhizophora stylosa with total content of 149g/kg were determined by HPIC-IPAD,six among which are essential amino acids,amounting to 46.15%of the total amino acids.And eight among which are unessential amino acids.The content of Glu,Phe,Arg and Val,amounting to 36.56g/kg,34.42g/kg,22.33g/kg and 15.47g/kg respectively were determined as the optimum amino acids.
4.The Maillard reaction products were obtained from the reaction of complex amino acids from leaves of Rhizophora stylosa hydrolysised by concentrated hydrochloric acid and glucose and sucrose for six hours under the temperature between degree centigrade 105 and 108 respectively.The ether-soluble materials from the reaction product were extracted by ethyl ether and determined by GC-MS.There are some different components in both of the nine components.Both products have aromatic substances.The results presented that Maillard reactions can take place by sucrose without reductive character.
5.The volatile oils from the leaves and fruits of mangrove plant Rhizophora stylosa were extracted by steam distillation and analyzed by GC-MS.Thirty-one volatile compounds in forty one separated from leaves of Rhizophora stylosa were identified, which accounted for 83.62%of the total volatile oil.BHT was determined as the optimum composition.2-Hydroxy-4-methylbenzoate,hentetracontyl alcohol and 2,6,10,15,19,23-hexamethyl tetracosane were discovered for the first time in the volatile oils from the leaves of Rhizophora stylosa.And all the volatile compositions separated from fruits of Rhizophora stylosa were identified,among which,3-Methoxy-1,2-propanediol,taking the proportion of 26.39%,was determined as the optimum composition.The six compounds of N,N'-di-benzoyloxy heptanediamide,2,3-Dihydro-benzofuran,1H-Imidazole-2-carboxaldehyde, Elemicin,3,7,11-Trimethyl-1,6,10-Dodecatrien-3-ol and 2,8-Dimethyl-4,6-nonanedione were discovered for the first time in the volatile oils from the fruits of mangrove plant Rhizophora stylosa.
6.The fatty acids,with the yield of 3.272%and 2.530%respectively,were extracted by Soxhlet extraction from the leaves and the fruits of mangrove plant Rhizophora stylosa. The extracted fatty acids were esterified and analyzed by gas chromatography-mass spectrometry.Twelve fatty acids were detected and identified,amounting to 84.95%of the total fatty acids from the leaves of Rhizophora stylosa.The compounds mainly includ palmitic acid(40.49%),oleic acid(17.24%) and linoleic acid(11.14%).Eight fatty acids, mainly including palmitic acid,8,11,14-eicosatrienoic acid and linoleic acid,respectively amounting to 7.59%,4.25%and 3.22%were identified from the fruits of Rhizophora stylosa.And 8,11,14-eicosatrienoic acid was discovered for the first time.
7.The polysaccharide,with the yield of 2%,was extracted from Rhizophpra stylosa leaves.And the polysaccharide extracted was tested and analyzed by IR.The IR spectrum indicates that there are characteristic absorption peaks of polysaccharides.Analyses by complete acid hydrolysis and aldoononitrile acetate derivatives and GC-MS indicated that it is composed of erythrose,D-arabinose and glucose.The results presented that the polysaccharide from Rhizophpra stylosa belongs to heteropolysaccharide.
8.The extract of crud flavonoids in Rhizophora stylosa leaves were extracted by ethanol and then separated and purified by extraction,polyamide packed chromatography and crystallization and needle crystal compound separated out.The needle crystal compound was identified structurally by UV,IR,MS and element analyzing combined with physical and chemical property as rutin.The molecular formula of Rhizophora stylosa rutin is C_(27)H_(30)O_(16) and its molecular weight is 610.5.The total flavonoids content of the crude flavonoids extract was determined as 58.29%by UV-spectrophotometry.
9.The in vitro antimicrobial activity experiments of total flavonoids extract from the mangrove plant Rhizophora stylosa were studied by the plate diluting method.The results presented that the total flavonoids extract had varied inhibitory effects on the bacteria and plant pathogenic fungi.The extract was more distinctly sensitive to Escherichia coli, Colletotrichum musae and Fusarium oxysporum f.sp.cubense,and less to Colletotrichum sp.,Rhizotonia solani and Staphylococcus aureus and no to Aspergillus niger.The minimal inhibitory concentrations(MIC) were determined by plate diluting method.
10.To evaluate anti-tumor activity of flavonoid extraction from Rhizophora stylosa, the anti-tumor activity of flavonoid extraction from Rhizophora stylosa against human lung cancer cell NCI-H460 were determined by MTT method.The result of the anti-tumor experiment presented that the flavonoid extraction from Rhizophora stylosa showed significant anti-tumor activity on human lung cancer cell NCI-H460 in vitro.
11.A single crystal was obtained from the wilt leaves of Rhizophora stylosa by crystal induction method with Cu~(2+).The single crystal's structure information and the crystal data were present by X-Ray difference reflection technology.The single crystal belongs to the triclinic system with the molecular formula of Cu(C_(10)H_(12)NO_2)_2.It's space group is PI and the crystal data presented as follows:a=5.50520(10),(?),b=8.0683(3)(?), c=11.3008(5)(?),α=70.338(3)°,β=89.399(2)°,γ=78.7060(10)°,V=462.70(3)(?)~3,Z=1, M_r=419,95,D_x=1.507mg·m~(-3),μ=1.020mm~(-1),F(000)=219,R=0.040,wR=0.107.It is proved that a ligand of the obtained complex is fusaric acid(C_(10)H_(13)NO_2).Then it is concluded the one of the reasons of the phenomenon is fusaric acid.The result of the anti-tumor experiment presented that the complex of fusaric acid and Cu~(2+) showed significant anti-tumor activity on human hepatoma cells BEL-7402 in vitro.
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