中国南海三种礁栖海洋生物化学成分及生物活性研究
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摘要
海洋生物海绵和珊瑚是珊瑚礁生态系统的重要组成,其物种多样性丰富且富含结构新颖的活性物质,是海洋天然产物研究的热点物种。为了寻找新的生物活性成分,本文对采自我国南海海域的海绵Aaptos suberitoides,粉灰扇软柳珊瑚Subergorgia ornate和聚裂丛柳珊瑚Rumphella aggregata进行了系统的化学成分和生物活性研究。综合运用多种现代色谱分离技术,从以上三种海洋生物样品的甲醇提取物中,共分离得到68个化合物。应用核磁共振(NMR),质谱(MS),红外光谱(IR)、紫外光谱(UV)和圆二色谱(CD)法等现代波谱技术确定了其中55个化合物的化学结构,发现新化合物19个,其余化合物均为首次从上述所研究的海绵或珊瑚中得到。
从南海海绵Aaptos suberitoides中共分离鉴定了23个化合物,化合物类型主要包括20个aaptamine类生物碱(AS-1-AS-15)：8,9,9-trimethoxy-9H-benzo [de][1,6]naphthyridine (AS-1), demethyl(oxy)aaptamine (AS-2), Suberitine A (*AS-3), Suberitine B (*AS-4), Suberitine C (*AS-5), Suberitine D (*AS-6), Suberitine E (*AS-7), Suberitine F (*AS-8), Suberitine G (*AS-9), Suberitine H (*AS-10), Suberitine I (*AS-11), Suberitine J (*AS-12), Suberitine K (*AS-13), Suberitine L (*AS-14), Suberitine M (*AS-15),其中手性聚合体Suberitine E (*AS-7), Suberitine F (*AS-8), Suberitine H (*AS-10), Suberitine J (*AS-12), Suberitine K (*AS-13), Suberitine L (*AS-14), Suberitine M (*AS-15),经手性拆分进一步纯化出(*AS-7a)和(*AS-7b),(*AS-8a)和(*AS-8b),(*AS-10a)和(*AS-10b),(*AS-14a)和(*AS-14b),(*AS-15a)和(*AS-15b)；1个咪唑类化合物：8a-methoxy-imidazo[1,5]-alpyridine-1,3-dione (*AS-16);1个聚酮类化合物：methyl-3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate (AS-17);1个核苷类化合物：胸腺嘧啶-2’-脱氧核苷(AS-18)。从中发现19个新化合物(*标记),特别是化合物AS-3-AS-15为一类全新的具有以罕见的C-3-C-3'、C-3-C-6'或C-3-C-9's键链接多个aaptamine结构单元形成的新骨架聚合型生物碱。此外,根据A. suberitoides中特征成分aaptamine生物碱(AS-1-AS-15)的结构特点并结合文献,推测了聚合型aaptamine生物碱的可能生合成途径,并对该类新颖生物碱进行了初步的化学合成机理及化学半合成探讨。
从粉灰扇软柳珊瑚Subergorgia ornate中共分离鉴定了9个化合物。化合物类型主要包括2个嘧啶类化合物：尿嘧啶(SO-1)、胸腺嘧啶(SO-2)；7个核苷类化合物：尿嘧啶核苷(SO-3)、尿嘧啶-2’-脱氧核苷(SO-4)、胸腺嘧啶核苷(SO-5)、胸腺嘧啶-2’-脱氧核苷(SO-6)、胞嘧啶核苷(SO-7)、次黄嘌呤核苷(So-8)、鸟嘌呤核苷(SO-9)。
从聚裂丛柳珊瑚Rumphella aggregata中共分离鉴定了23个化合物。化合物类型主要包括15个甾醇类化合物：胆甾醇(RA-1),(22E)-胆甾-5,22-二烯-3β-醇(RA-2),(22E)-麦角甾-5,22-二烯-3β-醇(RA-3),麦角甾-5,24(28)-二烯-3β-醇(RA-4),豆甾-5,24(28)-二烯-3β-醇(RA-5),柳珊瑚甾醇(RA-6),3β-羟基胆甾-5-烯-7-酮(RA-7),3β-羟基麦角甾-5-烯-7-酮(RA-8),(22E)-3β-羟基麦角甾-5,22-二烯-7-酮(RA-9),胆甾-7-烯-3β,5a,6β-三醇(RA-10),(22E)-胆甾-7,22-二烯-3β,5a,6β-三醇(RA-11)、麦角甾-7-烯-3β,5a,6β-三醇(RA-12)、(22E)-麦角甾-7,22-二烯-3β,5a,6β-三醇(RA-13)、豆甾-7-烯-3β,5a,6β-三醇(RA-14),(22E)-豆甾-7,22-二烯-3β,5a,6β-三醇(RA-15)；1个嘧啶类化合物：尿嘧啶(RA-16)；1个咖啡碱类化合物：咖啡因(RA-17)；1个类胡萝卜素类化合物：hydratoperidinin(RA-18)；5个脂质类化合物：5Z,8Z,11Z,14Z-四烯-十八碳酸甲酯(RA-19),5Z,8Z-二烯-十七碳酸甲酯(RA-20),5Z,8Z,11Z,14Z,17Z-五烯-二十碳酸甲酯(RA-21),5Z,8Z-二烯-二十碳酸甲酯(RA-22),5Z,8Z,11Z-三烯-十七碳酸甲酯(RA-23)。
选择P388(小鼠白血病细胞)、HeLa(人宫颈癌细胞)和K562(人白血病细胞)三种肿瘤细胞株,分别用MTT法和酶联免疫吸附测定(ELISA)法从细胞和分子水平对部分单体化合物的体外抗肿瘤活性进行了初步评价。活性筛选结果显示结构新颖的聚合型aaptamine生物碱化合物AS-4、AS-6和AS-8对P388(小鼠白血病细胞)肿瘤细胞株表现出潜在的细胞毒活性,IC50值分别为1.8μM、3.5μM和1.6μM；同时化合物AS-8在浓度为10μM时对HeLa(人宫颈癌细胞)和K562(人白血病细胞)肿瘤细胞也显示一定程度的细胞毒活性,对HeLa细胞的IC50值大于10μM,对K562细胞的IC50值为9.3μM；此外,化合物AS-8还是一种潜在的受体酪氨酸激酶c-Met酶活抑制剂,IC50值为5.4,uM。
In order to search for natural products with unique structural features and pronounced biological activities from marine organisms, a marine sponge Aaptos suberitoides and two corals Subergorgia ornate and Rumphella aggregate were collected from South China Sea. An extensive chromatographic examination was resulted in the isolation of63compounds from the selected marine sponge and corals, and55compounds' structures were determined on the basis of MS, NMR, IR, UV, CD method and by comparison with the reported data in literature, including19new ones, as well as36known ones which were discovered from the selected marine sponge and corals for the first time.
Eighteen compounds were isolated from the marine sponge Aaptos suberitoides. These compounds were structurally elucidated as fifteen aaptamine alkloids, namely,8,9,9-trimethoxy-9H-benzo[de][1,6]naphthyridine (AS-1), demethyl(oxy)aaptamine (AS-2), Suberitine A (*AS-3), Suberitine B (*AS-4), Suberitine C (*AS-5), Suberitine D (*AS-6), Suberitine E (*AS-7), Suberitine F (*AS-8), Suberitine G (*AS-9), Suberitine H (*AS-10), Suberitine I (*AS-11), Suberitine J (*AS-12), Suberitine K (*AS-13), Suberitine L (*AS-14), Suberitine M (*AS-15); the chiral compounds Suberitine E (*AS-7), Suberitine F (*AS-8), Suberitine H (*AS-10), Suberitine J (*AS-12), Suberitine K (*AS-13), Suberitine L (*AS-14), Suberitine M (*AS-15) were further purified throuth chiral resolution by HPLC to (*AS-7a) and (*AS-7b),(*AS-8a) and (*AS-8b),(*AS-10a) and (*AS-10b),(*AS-14a) and (*AS-14b),(*AS-15a) and (*AS-15b); and one imidazole, namely,8a-methoxy-imidazo[1,5]-alpyridine-1,3-dione)(*AS-16); and one polyketide, namely, methyl-3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate (AS-17); and one nucleosides, namely,2'-deoxythymidine (AS-18). Among them, there are fourteen new natural products (AS-3-AS-16), and compounds AS-3-AS-15are novel aaptamine alkaloids with two aaptamine skeleton units,8,9,9-trimethoxy-9H-benzo[de][1,6]naphthyridine and demethyl(oxy)aaptamine, linked through a rare C-3-C-3', C-3-C-6'or C-3-C-9'sigma bond between the [1,6]-naphthyridine rings. Moreover, a possible biosynthetic pathways of aaptamine alkloids AS-1-AS-15were postulated according to their structures and literatures, and some chemical synthesis of compounds AS-3-AS-15was also performed in the paper.
From the gorgonian coral Subergorgia ornate, nine compounds were isolated and characterized. The structure types included two miazines, namely, uracil (SO-1), thymine (SO-2); and seven nucleosides, namely, uridine (SO-3),2'-deoxyuridine (SO-4), thymidine (SO-5),2'-deoxythymidine (SO-6), cytidine (SO-7), inosine (SO-8), guanosine (SO-9).
From the gorgonian coral Rumphella aggregata, twenty-three compounds were isolated and characterized. The structure types included fifteen sterols, namely, cholesterol (RA-1),(22E)-cholest-5,22-dien-3β-ol (RA-2),(22E)-ergosta-5,22-dien-3β-ol (RA-3), ergosta-5,24(28)-dien-3β-ol (RA-4), stigmaster-5,24(28)-dien-3β?-ol (RA-5), gorgosterol (RA-6),3β-hydroxycholesta-5-en-7-one (RA-7),3β-hydroxyergosta-5-en-7-one(RA-8),(22E)-3β-hydroxyergosta-5,22-dien-7-one (RA-9), cholest-7-ene-3β,5a,6β-triol (RA-10), cholesta-7,22-dien-3β,5a,6β-triol (RA-11), ergosta-7-ene-3β,5a,6β-triol (RA-12),(22E)-ergosta-7,22-dien-3β,5a,6β-triol (RA-13), stigmaster-7-ene-3β,5a,6βtriol (RA-14),(22E)-stigmaster-7,22-dien-3β,5a,6β-triol (RA-15); and one miazines, namely, uracil (RA-16); and one caffeine (RA-17); and one carotenoid, namely, hydratoperidinin (RA-18); and five lipids, namely,5Z,8Z,11Z,14Z-tetraene-methyloctadecanoate (RA-19),5Z,8Z-diene-methyl heptadecanoate (RA-20),5Z,8Z,11Z,14Z,17Z-pentaene-methyleicosanoate (RA-21),5Z,8Z-diene-methyleicosanoate (RA-22),5Z,8Z,11Z-triene-methylheptadeca noate (RA-23).
Three tumor cell lines P388(murine leukemia cell), HeLa (human cervical carcinoma cells) and K562(chronic myelogenous leukemia cell lines of the original) were selected for in vitro antitumor activity screening with MTT method, and enzyme-linked immunosorbent assay (ELISA) method was used for most single compounds in the vitro antitumor activity of a preliminary evaluation. The results showed that the aaptamine alkloids, compounds AS-4, AS-6and AS-8showed potent cytotoxicity against P388cell lines, with IC50values of1.8μM,3.5μM and1.6μM, respectively. Compound AS-8also had moderate cytotoxicities against K562cell line with IC50values of9.3μM. Furthermore, Compound AS-8was a potent Receptor tyrosine kinase inhibitor, with IC50values of5.4μM, respectively.
从南海海绵Aaptos suberitoides中共分离鉴定了23个化合物,化合物类型主要包括20个aaptamine类生物碱(AS-1-AS-15)：8,9,9-trimethoxy-9H-benzo [de][1,6]naphthyridine (AS-1), demethyl(oxy)aaptamine (AS-2), Suberitine A (*AS-3), Suberitine B (*AS-4), Suberitine C (*AS-5), Suberitine D (*AS-6), Suberitine E (*AS-7), Suberitine F (*AS-8), Suberitine G (*AS-9), Suberitine H (*AS-10), Suberitine I (*AS-11), Suberitine J (*AS-12), Suberitine K (*AS-13), Suberitine L (*AS-14), Suberitine M (*AS-15),其中手性聚合体Suberitine E (*AS-7), Suberitine F (*AS-8), Suberitine H (*AS-10), Suberitine J (*AS-12), Suberitine K (*AS-13), Suberitine L (*AS-14), Suberitine M (*AS-15),经手性拆分进一步纯化出(*AS-7a)和(*AS-7b),(*AS-8a)和(*AS-8b),(*AS-10a)和(*AS-10b),(*AS-14a)和(*AS-14b),(*AS-15a)和(*AS-15b)；1个咪唑类化合物：8a-methoxy-imidazo[1,5]-alpyridine-1,3-dione (*AS-16);1个聚酮类化合物：methyl-3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate (AS-17);1个核苷类化合物：胸腺嘧啶-2’-脱氧核苷(AS-18)。从中发现19个新化合物(*标记),特别是化合物AS-3-AS-15为一类全新的具有以罕见的C-3-C-3'、C-3-C-6'或C-3-C-9's键链接多个aaptamine结构单元形成的新骨架聚合型生物碱。此外,根据A. suberitoides中特征成分aaptamine生物碱(AS-1-AS-15)的结构特点并结合文献,推测了聚合型aaptamine生物碱的可能生合成途径,并对该类新颖生物碱进行了初步的化学合成机理及化学半合成探讨。
从粉灰扇软柳珊瑚Subergorgia ornate中共分离鉴定了9个化合物。化合物类型主要包括2个嘧啶类化合物：尿嘧啶(SO-1)、胸腺嘧啶(SO-2)；7个核苷类化合物：尿嘧啶核苷(SO-3)、尿嘧啶-2’-脱氧核苷(SO-4)、胸腺嘧啶核苷(SO-5)、胸腺嘧啶-2’-脱氧核苷(SO-6)、胞嘧啶核苷(SO-7)、次黄嘌呤核苷(So-8)、鸟嘌呤核苷(SO-9)。
从聚裂丛柳珊瑚Rumphella aggregata中共分离鉴定了23个化合物。化合物类型主要包括15个甾醇类化合物：胆甾醇(RA-1),(22E)-胆甾-5,22-二烯-3β-醇(RA-2),(22E)-麦角甾-5,22-二烯-3β-醇(RA-3),麦角甾-5,24(28)-二烯-3β-醇(RA-4),豆甾-5,24(28)-二烯-3β-醇(RA-5),柳珊瑚甾醇(RA-6),3β-羟基胆甾-5-烯-7-酮(RA-7),3β-羟基麦角甾-5-烯-7-酮(RA-8),(22E)-3β-羟基麦角甾-5,22-二烯-7-酮(RA-9),胆甾-7-烯-3β,5a,6β-三醇(RA-10),(22E)-胆甾-7,22-二烯-3β,5a,6β-三醇(RA-11)、麦角甾-7-烯-3β,5a,6β-三醇(RA-12)、(22E)-麦角甾-7,22-二烯-3β,5a,6β-三醇(RA-13)、豆甾-7-烯-3β,5a,6β-三醇(RA-14),(22E)-豆甾-7,22-二烯-3β,5a,6β-三醇(RA-15)；1个嘧啶类化合物：尿嘧啶(RA-16)；1个咖啡碱类化合物：咖啡因(RA-17)；1个类胡萝卜素类化合物：hydratoperidinin(RA-18)；5个脂质类化合物：5Z,8Z,11Z,14Z-四烯-十八碳酸甲酯(RA-19),5Z,8Z-二烯-十七碳酸甲酯(RA-20),5Z,8Z,11Z,14Z,17Z-五烯-二十碳酸甲酯(RA-21),5Z,8Z-二烯-二十碳酸甲酯(RA-22),5Z,8Z,11Z-三烯-十七碳酸甲酯(RA-23)。
选择P388(小鼠白血病细胞)、HeLa(人宫颈癌细胞)和K562(人白血病细胞)三种肿瘤细胞株,分别用MTT法和酶联免疫吸附测定(ELISA)法从细胞和分子水平对部分单体化合物的体外抗肿瘤活性进行了初步评价。活性筛选结果显示结构新颖的聚合型aaptamine生物碱化合物AS-4、AS-6和AS-8对P388(小鼠白血病细胞)肿瘤细胞株表现出潜在的细胞毒活性,IC50值分别为1.8μM、3.5μM和1.6μM；同时化合物AS-8在浓度为10μM时对HeLa(人宫颈癌细胞)和K562(人白血病细胞)肿瘤细胞也显示一定程度的细胞毒活性,对HeLa细胞的IC50值大于10μM,对K562细胞的IC50值为9.3μM；此外,化合物AS-8还是一种潜在的受体酪氨酸激酶c-Met酶活抑制剂,IC50值为5.4,uM。
In order to search for natural products with unique structural features and pronounced biological activities from marine organisms, a marine sponge Aaptos suberitoides and two corals Subergorgia ornate and Rumphella aggregate were collected from South China Sea. An extensive chromatographic examination was resulted in the isolation of63compounds from the selected marine sponge and corals, and55compounds' structures were determined on the basis of MS, NMR, IR, UV, CD method and by comparison with the reported data in literature, including19new ones, as well as36known ones which were discovered from the selected marine sponge and corals for the first time.
Eighteen compounds were isolated from the marine sponge Aaptos suberitoides. These compounds were structurally elucidated as fifteen aaptamine alkloids, namely,8,9,9-trimethoxy-9H-benzo[de][1,6]naphthyridine (AS-1), demethyl(oxy)aaptamine (AS-2), Suberitine A (*AS-3), Suberitine B (*AS-4), Suberitine C (*AS-5), Suberitine D (*AS-6), Suberitine E (*AS-7), Suberitine F (*AS-8), Suberitine G (*AS-9), Suberitine H (*AS-10), Suberitine I (*AS-11), Suberitine J (*AS-12), Suberitine K (*AS-13), Suberitine L (*AS-14), Suberitine M (*AS-15); the chiral compounds Suberitine E (*AS-7), Suberitine F (*AS-8), Suberitine H (*AS-10), Suberitine J (*AS-12), Suberitine K (*AS-13), Suberitine L (*AS-14), Suberitine M (*AS-15) were further purified throuth chiral resolution by HPLC to (*AS-7a) and (*AS-7b),(*AS-8a) and (*AS-8b),(*AS-10a) and (*AS-10b),(*AS-14a) and (*AS-14b),(*AS-15a) and (*AS-15b); and one imidazole, namely,8a-methoxy-imidazo[1,5]-alpyridine-1,3-dione)(*AS-16); and one polyketide, namely, methyl-3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate (AS-17); and one nucleosides, namely,2'-deoxythymidine (AS-18). Among them, there are fourteen new natural products (AS-3-AS-16), and compounds AS-3-AS-15are novel aaptamine alkaloids with two aaptamine skeleton units,8,9,9-trimethoxy-9H-benzo[de][1,6]naphthyridine and demethyl(oxy)aaptamine, linked through a rare C-3-C-3', C-3-C-6'or C-3-C-9'sigma bond between the [1,6]-naphthyridine rings. Moreover, a possible biosynthetic pathways of aaptamine alkloids AS-1-AS-15were postulated according to their structures and literatures, and some chemical synthesis of compounds AS-3-AS-15was also performed in the paper.
From the gorgonian coral Subergorgia ornate, nine compounds were isolated and characterized. The structure types included two miazines, namely, uracil (SO-1), thymine (SO-2); and seven nucleosides, namely, uridine (SO-3),2'-deoxyuridine (SO-4), thymidine (SO-5),2'-deoxythymidine (SO-6), cytidine (SO-7), inosine (SO-8), guanosine (SO-9).
From the gorgonian coral Rumphella aggregata, twenty-three compounds were isolated and characterized. The structure types included fifteen sterols, namely, cholesterol (RA-1),(22E)-cholest-5,22-dien-3β-ol (RA-2),(22E)-ergosta-5,22-dien-3β-ol (RA-3), ergosta-5,24(28)-dien-3β-ol (RA-4), stigmaster-5,24(28)-dien-3β?-ol (RA-5), gorgosterol (RA-6),3β-hydroxycholesta-5-en-7-one (RA-7),3β-hydroxyergosta-5-en-7-one(RA-8),(22E)-3β-hydroxyergosta-5,22-dien-7-one (RA-9), cholest-7-ene-3β,5a,6β-triol (RA-10), cholesta-7,22-dien-3β,5a,6β-triol (RA-11), ergosta-7-ene-3β,5a,6β-triol (RA-12),(22E)-ergosta-7,22-dien-3β,5a,6β-triol (RA-13), stigmaster-7-ene-3β,5a,6βtriol (RA-14),(22E)-stigmaster-7,22-dien-3β,5a,6β-triol (RA-15); and one miazines, namely, uracil (RA-16); and one caffeine (RA-17); and one carotenoid, namely, hydratoperidinin (RA-18); and five lipids, namely,5Z,8Z,11Z,14Z-tetraene-methyloctadecanoate (RA-19),5Z,8Z-diene-methyl heptadecanoate (RA-20),5Z,8Z,11Z,14Z,17Z-pentaene-methyleicosanoate (RA-21),5Z,8Z-diene-methyleicosanoate (RA-22),5Z,8Z,11Z-triene-methylheptadeca noate (RA-23).
Three tumor cell lines P388(murine leukemia cell), HeLa (human cervical carcinoma cells) and K562(chronic myelogenous leukemia cell lines of the original) were selected for in vitro antitumor activity screening with MTT method, and enzyme-linked immunosorbent assay (ELISA) method was used for most single compounds in the vitro antitumor activity of a preliminary evaluation. The results showed that the aaptamine alkloids, compounds AS-4, AS-6and AS-8showed potent cytotoxicity against P388cell lines, with IC50values of1.8μM,3.5μM and1.6μM, respectively. Compound AS-8also had moderate cytotoxicities against K562cell line with IC50values of9.3μM. Furthermore, Compound AS-8was a potent Receptor tyrosine kinase inhibitor, with IC50values of5.4μM, respectively.
引文
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