中国南海侧扁软柳珊瑚化学成分及生物活性研究
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摘要
软柳珊瑚属（Subergorgia）侧扁软柳珊瑚（S. suberosa）在我国南海海域分布广泛,用药历史悠久。该物种中所含有的次生代谢成分类型多样，主要包括倍半萜类、甾醇类、生物碱类等化合物。部分化合物显示出有意义的抗肿瘤、抗菌、抗捕食等活性。为了寻找结构新颖、具有抗肿瘤活性的化学成分，本论文选择采自中国南海海域的侧扁软柳珊瑚（S. suberosa）作为研究对象，以体外抗肿瘤活性（细胞毒）为导向，综合运用HPLC等多种色谱分离技术及核磁共振（1D及2D NMR），质谱（MS），红外光谱（IR）、紫外光谱（UV）等现代波谱技术从该珊瑚的氯仿-甲醇提取物中分离鉴定了51个化合物，其中包括17个新化合物，另有19个化合物为首次从该种珊瑚中发现。
这些化合物主要包括16个9,11-开环甾醇类化合物（CBR-1~CBR-11,CBR-17~CBR-21）：subergorgol A（CBR-1），subergorgol B（CBR-2），subergorgolC（CBR-3），subergorgol D（CBR-4）， subergorgol E（CBR-5），subergorgol F（CBR-6），subergorgol G（CBR-7），subergorgol H（CBR-8），subergorgol I（CBR-9）， subergorgol J （CBR-10）， subergorgol K （CBR-11），9,11-seco-3β,6α,11-trihydroxy-5α-cholest-7-en-9-one（CBR-17），9,11-seco-3β,6α,11-trihydroxy-24-methylene-5α-cholest-7-en-9-one （CBR-18），24-nor-9,11-seco-3β,6α,11-trihydroxy-5α-cholest-7,22(E)-dien-9-one（CBR-19），3β,6α,11-trihydroxy-24-methyl-5α-cholest-9,11-seco-7,22(E)-diene-9-one （CBR-20），和3β,6α,11-trihydroxy-24-methyl-5α-cholest-9,11-seco-7-en-9-one （CBR-21）,其中化合物CBR-1~CBR-11为新化合物；10个生物碱类化合物（CBR-12~CBR-16，CBR-22~CBR-26）：subergorgine A（CBR-12），subergorgine B（CBR-13），subergorgine C（CBR-14），subergorgine D（CBR-15），subergorgine E（CBR-16），尿嘧啶（CBR-22），胸腺嘧啶（CBR-23），尿嘧啶核苷（CBR-24），胸腺嘧啶核苷（CBR-25），次黄嘌呤核苷（CBR-26)，其中化合物CBR-12~CBR-16为新化合物；3个脂肪酸和聚酮类化合物：油酸（CBR-27），正十六烷酸（CBR-28）及methyl-3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate（CBR-29）；14个甾醇类化合物：24(β)-甲基-胆甾-5,22-二烯-3β-醇（CBR-30），24(α)-甲基-胆甾-5,22-二烯-3β-醇（CBR-31），胆甾醇（CBR-32），麦角甾-5,24(28)-二烯-3β-醇（CBR-33），胆甾-5,22-二烯-3β-醇（CBR-34），孕甾-3β-羟基-20-酮（CBR-35），孕甾-3β-乙酰氧基-20-酮（CBR-36），孕甾-3,20-二酮（CBR-37），孕甾-4-烯-3,20-二酮（CBR-38），孕甾-1-烯-3,20-二酮（CBR-39），孕甾-1,4-二烯-3,20-二酮（CBR-40），孕甾-6β-羟基-4-烯-3,20-二酮（CBR-41），孕甾-1,4-二烯-3-酮-20-羧酸甲酯（CBR-42），(3β,5α,6β,22E)-麦角甾-7,22-二烯-3,5,6-三醇（CBR-43）；五个倍半萜类化合物suberosenol A（CBR-44），suberosanone（CBR-45），柳珊瑚酸（CBR-46），Subergorgic acid methyl ester（CBR-47），Subergorgic acid ethylester（CBR-48）；两个甘油醚：鲨甘醇（CBR-49），3-(二十烷氧基)丙烷-1,2-二醇（CBR-50)；一个脂肪醇：正十七醇（CBR-51）。
发现的9,11-开环甾醇化合物均具有特征的3β,6α,11-trihydroxy-7-en-9-one-5α-9,11-secosteroid母核，新化合物CBR-1~CBR-11呈现新颖多样的侧链衍生特性，其中化合物CBR-1~CBR-5的20位羟基化，CBR-6和CBR-7的侧链氧化形式为首次发现。新化合物CBR-12~CBR-16则为罕见的嘌呤类倍半萜生物碱，倍半萜母核均为subergane型，碱基部分为嘌呤衍生物，CBR-16的碱基为次黄嘌呤脱氧核苷。新化合物CBR-48推测为部分样品在乙醇中浸泡过程中得到的人工产物。
选择人宫颈癌细胞（HeLa）、人乳腺癌细胞株（MDA-MB-231）和人白血病细胞（K562）三种肿瘤细胞株，分别用MTT法和SRB法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CBR-9对K562及MDA-MB-231细胞株有较强的抑制活性，IC50值分别为5.5，6.2μM；CBR-10对K562细胞株也有很好的抑制作用，IC50值为6.5μM。初步显示出该物种潜在的天然药物研究意义。5个嘌呤类倍半萜生物碱的生物活性检测尚在进行中。
The gorgonian Subergorgia suberosa is widely distributed in the Indo-Pacificwaters and has been found to contain structurally diverse secondary metabolitesincluding sesquiterpenes,9,11-secosteroids, pregnane derivatives and alkaloids. Someof these metabolites were reported to exhibit diverse biological activities, e.g.,cytocoxic, antimicrobial or anti-cholinesterase effects.
In order to search for biologically active metabolites from marine organisms, amarine gorgonian S. suberosa collected from South China Sea was studied. Ourinvestigation of CHCl-MeOH (1:1, v/v) extract of S. suberosa has now led to theisolation of51compounds whose structures were determined mainly on the basis ofMS, NMR, IR, UV techniques and by comparison with the reported data in literature.
Of the51(CBR-1~CBR-51) compounds,16were structurally elucidated as9,11-secosteroids, namely, subergorgol A (CBR-1)， subergorgol B (CBR-2)，subergorgol C (CBR-3)，subergorgol D (CBR-4)， subergorgol E (CBR-5)，subergorgol F (CBR-6)， subergorgol G (CBR-7)， subergorgol H (CBR-8)，subergorgol I (CBR-9)， subergorgol J (CBR-10)， subergorgol K (CBR-11)，9,11-seco-3β,6α,11-trihydroxy-5α-cholest-7-en-9-one (CBR-17),9,11-seco-3β,6α,11-trihydroxy-24-methylene-5α-cholest-7-en-9-one (CBR-18),24-nor-9,11-seco-3β,6α,11-trihydroxy-5α-cholest-7,22(E)-dien-9-one (CBR-19),3β,6α,11-trihydroxy-24-methyl-5α-cholest-9,11-seco-7,22(E)-diene-9-one (CBR-20) and3β,6α,11-trihydroxy-24-methyl-5α-cholest-9,11-seco-7-en-9-one (CBR-21)。All of them shairthe same3β,6α,11-trihydroxy-7-en-9-one-5α-9,11-secosteroid core structure withdiverse side chains and CBR-1~CBR-11are new compounds. In particular,compounds CBR1~5possess side chains hydroxylated at C-20, and compounds CBR6~7feature a unique steroid side chain with20(22) E–double bond and23-methoxyfunctional groups. New compounds subergorgine A-E (CBR-12~CBR-16) are raresesquiterpene-alkaloids with both purine and subergane–type sesquiterpene moieties,and the key differences are among link locations between two moieties. Other compounds are uracil (CBR-22), thymine (CBR-23), uridine (CBR-24), thymidine(CBR-25), inosine (CBR-26), oleic acid (CBR-27), palmitic acid (CBR-28),methyl-3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate (CBR-29),24β–melthyl-cholest-5,22-dine-3β-ol (CBR-30),24(α)–melthyl-cholest-5,22-dine-3β-ol (CBR-31),cholesterol (CBR-32), ergosta-5,24(28)-diene-3β-ol (CBR-33), cholest-5,22-diene-3β-ol (CBR-34),3β-hydroxy-5α-pregnan-20-one (CBR-35),3β-acetoxy-5α-pregnan-20-one (CBR-36),5α-pregnan-3,20-dione (CBR-37),5α-pregnan-4-ene-3,20-dione (CBR-38),5α-pregnan-1-ene-3,20-dione (CBR-39),5α-pregnan-1,4-diene-3,20-dione (CBR-40),6β-hydroxy-4-ene-pregnen-3,20-dione(CBR-41),pregnan-1,4-diene-3-one-20-carboxylic methyl ether (CBR-42),(3β,5α,6β,22E)-ergosta-7,22-diene-3,5,6-triol (CBR-43), suberosenol A (CBR-44)，suberosanone (CBR-45), subergorgic acid (CBR-46), subergorgic acid methyl ester(CBR-47), subergorgic acid ethyl ester (CBR-48), batyl alcohol (CBR-49),3-(icosyloxy)propane-1,2-diol (CBR-50), and heptadecanol (CBR-51), respectively.
Three tumor cell lines of human cervical carcinoma cells (HeLa), human breastcancer cells (MDA-MB-231) and chronic myelogenous leukemia cell lines (K562)were selected for testing antitumor activity in vitro with MTT or SRB method.Compound CBR-9showed significant cytotoxicities toward both K562andMDA-MB-231cell lines with IC50values of5.5and6.2μM, respectively, andcompound CBR-10also showed significant inhibitory activity against K562cell linewith an IC50value of6.5μM.
这些化合物主要包括16个9,11-开环甾醇类化合物（CBR-1~CBR-11,CBR-17~CBR-21）：subergorgol A（CBR-1），subergorgol B（CBR-2），subergorgolC（CBR-3），subergorgol D（CBR-4）， subergorgol E（CBR-5），subergorgol F（CBR-6），subergorgol G（CBR-7），subergorgol H（CBR-8），subergorgol I（CBR-9）， subergorgol J （CBR-10）， subergorgol K （CBR-11），9,11-seco-3β,6α,11-trihydroxy-5α-cholest-7-en-9-one（CBR-17），9,11-seco-3β,6α,11-trihydroxy-24-methylene-5α-cholest-7-en-9-one （CBR-18），24-nor-9,11-seco-3β,6α,11-trihydroxy-5α-cholest-7,22(E)-dien-9-one（CBR-19），3β,6α,11-trihydroxy-24-methyl-5α-cholest-9,11-seco-7,22(E)-diene-9-one （CBR-20），和3β,6α,11-trihydroxy-24-methyl-5α-cholest-9,11-seco-7-en-9-one （CBR-21）,其中化合物CBR-1~CBR-11为新化合物；10个生物碱类化合物（CBR-12~CBR-16，CBR-22~CBR-26）：subergorgine A（CBR-12），subergorgine B（CBR-13），subergorgine C（CBR-14），subergorgine D（CBR-15），subergorgine E（CBR-16），尿嘧啶（CBR-22），胸腺嘧啶（CBR-23），尿嘧啶核苷（CBR-24），胸腺嘧啶核苷（CBR-25），次黄嘌呤核苷（CBR-26)，其中化合物CBR-12~CBR-16为新化合物；3个脂肪酸和聚酮类化合物：油酸（CBR-27），正十六烷酸（CBR-28）及methyl-3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate（CBR-29）；14个甾醇类化合物：24(β)-甲基-胆甾-5,22-二烯-3β-醇（CBR-30），24(α)-甲基-胆甾-5,22-二烯-3β-醇（CBR-31），胆甾醇（CBR-32），麦角甾-5,24(28)-二烯-3β-醇（CBR-33），胆甾-5,22-二烯-3β-醇（CBR-34），孕甾-3β-羟基-20-酮（CBR-35），孕甾-3β-乙酰氧基-20-酮（CBR-36），孕甾-3,20-二酮（CBR-37），孕甾-4-烯-3,20-二酮（CBR-38），孕甾-1-烯-3,20-二酮（CBR-39），孕甾-1,4-二烯-3,20-二酮（CBR-40），孕甾-6β-羟基-4-烯-3,20-二酮（CBR-41），孕甾-1,4-二烯-3-酮-20-羧酸甲酯（CBR-42），(3β,5α,6β,22E)-麦角甾-7,22-二烯-3,5,6-三醇（CBR-43）；五个倍半萜类化合物suberosenol A（CBR-44），suberosanone（CBR-45），柳珊瑚酸（CBR-46），Subergorgic acid methyl ester（CBR-47），Subergorgic acid ethylester（CBR-48）；两个甘油醚：鲨甘醇（CBR-49），3-(二十烷氧基)丙烷-1,2-二醇（CBR-50)；一个脂肪醇：正十七醇（CBR-51）。
发现的9,11-开环甾醇化合物均具有特征的3β,6α,11-trihydroxy-7-en-9-one-5α-9,11-secosteroid母核，新化合物CBR-1~CBR-11呈现新颖多样的侧链衍生特性，其中化合物CBR-1~CBR-5的20位羟基化，CBR-6和CBR-7的侧链氧化形式为首次发现。新化合物CBR-12~CBR-16则为罕见的嘌呤类倍半萜生物碱，倍半萜母核均为subergane型，碱基部分为嘌呤衍生物，CBR-16的碱基为次黄嘌呤脱氧核苷。新化合物CBR-48推测为部分样品在乙醇中浸泡过程中得到的人工产物。
选择人宫颈癌细胞（HeLa）、人乳腺癌细胞株（MDA-MB-231）和人白血病细胞（K562）三种肿瘤细胞株，分别用MTT法和SRB法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CBR-9对K562及MDA-MB-231细胞株有较强的抑制活性，IC50值分别为5.5，6.2μM；CBR-10对K562细胞株也有很好的抑制作用，IC50值为6.5μM。初步显示出该物种潜在的天然药物研究意义。5个嘌呤类倍半萜生物碱的生物活性检测尚在进行中。
The gorgonian Subergorgia suberosa is widely distributed in the Indo-Pacificwaters and has been found to contain structurally diverse secondary metabolitesincluding sesquiterpenes,9,11-secosteroids, pregnane derivatives and alkaloids. Someof these metabolites were reported to exhibit diverse biological activities, e.g.,cytocoxic, antimicrobial or anti-cholinesterase effects.
In order to search for biologically active metabolites from marine organisms, amarine gorgonian S. suberosa collected from South China Sea was studied. Ourinvestigation of CHCl-MeOH (1:1, v/v) extract of S. suberosa has now led to theisolation of51compounds whose structures were determined mainly on the basis ofMS, NMR, IR, UV techniques and by comparison with the reported data in literature.
Of the51(CBR-1~CBR-51) compounds,16were structurally elucidated as9,11-secosteroids, namely, subergorgol A (CBR-1)， subergorgol B (CBR-2)，subergorgol C (CBR-3)，subergorgol D (CBR-4)， subergorgol E (CBR-5)，subergorgol F (CBR-6)， subergorgol G (CBR-7)， subergorgol H (CBR-8)，subergorgol I (CBR-9)， subergorgol J (CBR-10)， subergorgol K (CBR-11)，9,11-seco-3β,6α,11-trihydroxy-5α-cholest-7-en-9-one (CBR-17),9,11-seco-3β,6α,11-trihydroxy-24-methylene-5α-cholest-7-en-9-one (CBR-18),24-nor-9,11-seco-3β,6α,11-trihydroxy-5α-cholest-7,22(E)-dien-9-one (CBR-19),3β,6α,11-trihydroxy-24-methyl-5α-cholest-9,11-seco-7,22(E)-diene-9-one (CBR-20) and3β,6α,11-trihydroxy-24-methyl-5α-cholest-9,11-seco-7-en-9-one (CBR-21)。All of them shairthe same3β,6α,11-trihydroxy-7-en-9-one-5α-9,11-secosteroid core structure withdiverse side chains and CBR-1~CBR-11are new compounds. In particular,compounds CBR1~5possess side chains hydroxylated at C-20, and compounds CBR6~7feature a unique steroid side chain with20(22) E–double bond and23-methoxyfunctional groups. New compounds subergorgine A-E (CBR-12~CBR-16) are raresesquiterpene-alkaloids with both purine and subergane–type sesquiterpene moieties,and the key differences are among link locations between two moieties. Other compounds are uracil (CBR-22), thymine (CBR-23), uridine (CBR-24), thymidine(CBR-25), inosine (CBR-26), oleic acid (CBR-27), palmitic acid (CBR-28),methyl-3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate (CBR-29),24β–melthyl-cholest-5,22-dine-3β-ol (CBR-30),24(α)–melthyl-cholest-5,22-dine-3β-ol (CBR-31),cholesterol (CBR-32), ergosta-5,24(28)-diene-3β-ol (CBR-33), cholest-5,22-diene-3β-ol (CBR-34),3β-hydroxy-5α-pregnan-20-one (CBR-35),3β-acetoxy-5α-pregnan-20-one (CBR-36),5α-pregnan-3,20-dione (CBR-37),5α-pregnan-4-ene-3,20-dione (CBR-38),5α-pregnan-1-ene-3,20-dione (CBR-39),5α-pregnan-1,4-diene-3,20-dione (CBR-40),6β-hydroxy-4-ene-pregnen-3,20-dione(CBR-41),pregnan-1,4-diene-3-one-20-carboxylic methyl ether (CBR-42),(3β,5α,6β,22E)-ergosta-7,22-diene-3,5,6-triol (CBR-43), suberosenol A (CBR-44)，suberosanone (CBR-45), subergorgic acid (CBR-46), subergorgic acid methyl ester(CBR-47), subergorgic acid ethyl ester (CBR-48), batyl alcohol (CBR-49),3-(icosyloxy)propane-1,2-diol (CBR-50), and heptadecanol (CBR-51), respectively.
Three tumor cell lines of human cervical carcinoma cells (HeLa), human breastcancer cells (MDA-MB-231) and chronic myelogenous leukemia cell lines (K562)were selected for testing antitumor activity in vitro with MTT or SRB method.Compound CBR-9showed significant cytotoxicities toward both K562andMDA-MB-231cell lines with IC50values of5.5and6.2μM, respectively, andcompound CBR-10also showed significant inhibitory activity against K562cell linewith an IC50value of6.5μM.
引文
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