图纹白尼参和奇乳海参中生物活性成分研究
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摘要
海洋占地球面积的70％以上，蕴藏着极其丰富的生物资源，如何从海洋生物中找到具有抗肿瘤活性的物质已经成为现代药物研究的一个热点。
海参具有很高的药用价值，自古作为药用，《本草原始》记载：海参具“补肾精、益精髓、消痰涎、摄小便、壮阳、生百脉血、治溃疡”等功效。海参皂苷是海参的主要次生代谢产物，是海参主要活性化学成分，也是迄今为止唯一在动物体内发现的三萜皂苷类成分。药理研究表明，海参皂苷具有细胞毒、抗真菌、溶血等广泛生物活性。
作为本研究中心“海洋天然活性成分研究和新药开发”这一研究方向的子课题，本文主要介绍了图纹白尼参(Bohadschia marmorata Jaeger)和奇乳海参[Holothuria(Microthele)axiloga H．L．Clark]中三萜皂苷类成分的结构及生物活性研究。两种海参均生长分布于我国南海海域。早前日本学者曾对图纹白尼参的同物异名海参(Bohadschiabivittata Mitsukuri)做过研究，得到四个海参皂苷，并考查了其抗真菌活性，但目前尚未见有关奇乳海参体内皂苷类成分的研究报道。在本课题的研究中，作者应用硅胶、反相硅胶、葡聚糖凝胶等多种现代层析分离技术，对图纹白尼参及奇乳海参体内的三萜皂苷类成分进行了系统的分离纯化和药理研究，从图纹白尼参中分离鉴定了36个三萜皂苷化合物，从奇乳海参中分离鉴定了21个三萜皂苷化合物。应用现代光谱技术(尤其是2D-NMR)、ESI-MS技术和化学方法对这些化合物进行结构测定，确定了其化学结构和立体构型。其中新化合物共计26个。
从图纹白尼参中分离鉴定了36个三萜皂苷化合物，其化学结构鉴定如下，BM-1：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)，25(26)-海参烷烯-3β，12α-二醇(命名为：25，26-dehydro bivittoside D)；BM-2：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)，24(25)-海参烷烯-3β，12α，17α-三醇(命名为：17-hydroxyimpatienside A)；BM-3：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)，23(24)-海参烷烯-3β，12α，25-三醇(命名为：marmorosideA)；BM-4：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-25-乙酰氧基-9(11)-海参烷烯-3β，12α-二醇(命名为：25-acetoxy bivittoside D)；BM-5：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)，24(25)-海参烷烯-3β，12α-二醇(impatienside A)；BM-6：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)-海参烷烯-3β，12α-二醇(bivittoside D)；BM-7：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-12-羰基-9(11)-海参烷烯-3β-醇(命名为：marmoroside E)；BM-8：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)，24(25)-海参烷烯-3β，12α，22-三醇(命名为：22-hydroxy impatienside A)；BM-9：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-9(11)-海参烷烯-3β，12α，17α-三醇(命名为：marmoroside D)；BM-10：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)-海参烷烯-3β，12α，17α，25-四醇(命名为：marmoroside F)；BM-11：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基)-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(命名为：marmoro-side G)；BM-12：3-O-{(β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖-(1→4)]-β-D-吡喃木糖基}-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(命名为：marmoroside H)；BM-13：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃葡萄糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)，24(25)-海参烷烯-3β，12α-二醇(命名为：marmoroside I)；BM-14：3-O{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-24-羰基-9(11)-海参烷烯-3β，12α-二醇(命名为：24-one bivittosideD)；BM-15：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-16-乙酰氧基-9(11)，24(25)-海参烷烯-3β，12α，17α-三醇(命名为：marmoroside J)；BM-16：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-22，25-环氧-9(11)-海参烷烯-3β，12α-二醇(命名为：17-dehydroxy marmoroside G)；BM-17：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-9(11)，24(25)-海参烷烯-3β，12α-二醇(命名为：marmoroside K)；BM-18：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-9(11)，24(25)-海参烷烯-3β，12α，17α-三醇(命名为：17-hydroxymarmomside K)；BM-19：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-22，25-环氧-9(11)-海参烷烯-3β，12α-二醇(命名为：17-dehydroxy holothurinoside A)；BM-20：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(holothurinoside A)；BM-21：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22-羰基-9(11)-海参烷烯-3β，12α-二醇(fuscocineroside B)；BM-22：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)4-O-硫酸钠-β-D-吡喃木糖基]-22-羰基-25-乙酰氧基-9(11)-海参烷烯-3β，12α-二醇(fuscocineroside A)；BM-23：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22-羰基-25-乙酰氧基-9(11)-海参烷烯-3β，12α，17α-三醇(命名为：marmoroside C)；BM-24：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-9(11)-海参烷烯-3β，12α-二醇(pervicoside C)；BM-25：3-O[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22-羰基-9(11)-海参烷烯-3β，12α，17α-三醇(命名为：17-hydroxy fuscocineroside B)；BM-26：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基基]-22-羰基-9(11)-海参烷烯-3β，12α，25-三醇(命名为：25-hydroxyfuscocineroside B)；BM-27：3-O-](3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22，25-坏氧-9(11)-海参烷烯-3β，12α，17α-三醇(holothurin A)；BM-28：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22，25-环氧-9(11)-海参烷烯-3β，12α-二醇(fuscocineroside C)；BM-29：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-25-乙酰氧基-9(11)-海参烷烯-3β，12α-二醇(pervicoside A)；BM-30：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-β-D-吡喃木糖基]-9(11)，24(25)-海参烷烯-3β，12α-二醇(命名为：24，25-dehydro marmoroside L)；BM-31：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-β-D-吡喃木糖基]-9(11)-海参烷烯-3β，12α-二醇(命名为：marmoroside L)；BM-32：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-β-D-吡喃木糖基]-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(DS-holothurin A)；BM-33：3-O-[(3-D-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃葡萄糖-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22，25-环氧-9(11)-海参烷烯-3β，12α-二醇(命名为：marmoroside B)；BM-34：3-O-{β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)，24(25)-海参烷烯-3β，12α-二醇(命名为：24，25-dehydro bivittoside B)；BM-35：3-O-{β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)-海参烷烯-3β，12α-二醇(bivittoside B)；BM-36：3-O-[β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(命名为：holothurin B)。
从奇乳海参中分离鉴定了21个三萜皂苷化合物，其化学结构鉴定如下，HA-1：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃木糖基基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-7(8)，25(26)-海参烷烯-3β-醇(stichloroside B2)；HA-2：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃木糖基基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-7(8)-海参烷烯-3β-醇(stichloroside B1)；HA-3：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃木糖基基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-7(8)，25(26)-海参烷烯-3β-醇(stichloroside C2)；HA-4：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃木糖基基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-7(8)-海参烷烯-3β-醇(stichloroside C1)：HA-5：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃木糖基基-(1→4)-β-D-吡喃木糖基基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-7(8)-海参烷烯-3β-醇(命名为：axilogoside B)；HA-6：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃木糖基基-(1→4)-β-D-吡喃葡萄糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-βD-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-7(8)-海参烷烯-3β-醇(命名为：axilogoside C)；HA-7：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(marmoroside G)；HA-8：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃木糖基基-(1→4)-β-D-吡喃木糖基基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-9(11)-海参烷烯-3β，12α-二醇(命名为：axilogoside D)；HA-9：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-9(11)，24(25)-海参烷烯-3β，12α-二醇(marmoroside K)；HA-10：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)，24(25)-海参烷烯-3β，12α-二醇(命名为：axilogoside E)；HA-11：3-O-{(β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-22，25-环氧-9(11)-海参烷烯-3β，12α-二醇(axilogoside F)；HA-12：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)4-O-硫酸钠-β-D-吡喃木糖基]-9(11)-海参烷烯-3β，12α，17α，22-四醇(holothurin A1)；HA-13：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-9(11)-海参烷烯-3β，12α，17α-三醇(echinoside A)；HA-14：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-9(11)-海参烷烯-3β，12α-二醇(pervicoside C)；HA-15：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22-羰基-9(11)-海参烷烯-3β，12α-二醇(fuscocinerosideB)；HA-16：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)4-O-硫酸钠-β-D-吡喃木糖基]-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(holothurin A)；HA-17：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22，25-环氧-9(11)-海参烷烯-3β，12α-二醇(fuscocineroside C)；HA-18：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22-羰基-25-乙酰氧基-9(11)-海参烷烯-3β，12α-二醇(fuscocinero-side A)；HA-19：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-25-乙酰氧基-9(11)-海参烷烯-3β，12α-二醇(pervicoside A)；HA-20：3-O-[β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(holothurin B)；HA-21：3-O-[β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸-β-D-吡喃木糖基]-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(axilogoside A)。
其中BM-1；BM-2；BM-3；BM-4；BM-7；BM-8；BM-9；BM-10；BM-11；BM-12；BM-13；BM-14；BM-15；BM-16；BM-17；BM-18；BM-19；BM-23；BM-25；BM-26；BM-30；BM-31；BM-33；BM-34为从图纹白尼参中得到的新海参皂苷类化合物；HA-5；HA-6；HA-8；HA-10；HA-21为从奇乳海参中得到的新海参皂苷类化合物。
抗真菌活性筛选表明：BM-1；BM-2；BM-5；BM-6；BM-7；BM-13；BM-24；BM-30；BM-31；BM-34；BM-35；HA-13；HA-14对白色念珠菌有很强的抑制活性；BM-1；BM-2；BM-4；BM-5；BM-6；BM-7；BM-13；BM-17；BM-19；BM-20；BM-24；BM-27；BM-30；BM-31；BM-34；BM-35；BM-36；HA-13；HA-14；HA-16；HA-20对新生隐球菌有很强的抑制活性；BM-1；BM-2；BM-5；BM-6；BM-13；BM-17；BM-24；BM-30；BM-31；BM-34；BM-35；HA-13；HA-14对薰烟曲霉菌有很强的抑制活性；BM-1；BM-4；BM-5；BM-6；BM-9；BM-11；BM-17；BM-19；BM-20；BM-24；BM-30；BM-31；BM-32；BM-34；BM-35；HA-13；HA-14对红色毛癣菌有很强的抑制活性；BM-1；BM-2；BM-5；BM-6；BM-7；BM-13；BM-24；BM-30；BM-31；BM-34；BM-35；HA-13；HA-14对热带念珠菌有很强的抑制活性；BM-2；BM-5；BM-6；BM-7；BM-13；BM-24；BM-30；BM-31；BM-34；BM-35；HA-13；HA-14对克鲁斯假丝酵母菌有很强的抑制活性。MIC_(80)值均≤4μg／ml，有进一步研究的价值。
体外细胞毒试验显示：BM-1；BM-2；BM-5和BM-6对A549人肺癌细胞株有强效细胞毒活性，而BM-24则显示弱效。BM-1；BM-2；BM-5和BM-6对MOLT-4人白血病细胞株显示弱效细胞毒活性。
本课题对图纹白尼参和奇乳海参的化学成分及其药理作用进行的系统深入研究，为进一步研制开发新的抗癌和抗真菌药物提供了科学依据和有价值的先导化合物，也为海洋天然产物的研究积累了新的研究资料，对开发利用我国丰富的海参生物资源具有较重要的意义。
Bohadschia marmorata Jaeger and Holothuria (Microthele) axiloga H.L.Clark are abundant sea cucumbers distributed in South China Sea. Japanese researchers had reported the structures and antifungal activityes of four new triterpene glycosides isolated from the sea cucumber Bohadschia bivittata Mitsukuri. But no chemical works have been performedon the sea cucumber Holothuria (Microthele) axiloga H.L.Clark up to date. The antifungalconstituents of B. marmorata and H. axiloga have been investigated by various chromatographymethods including LPLC, MPLC, HPLC on silica gel and ODS respectively. Fifty-seventriterpene glycosides were isolated, then the chemical structures of the twenty-eightnew compounds were elucidated by chemical reactions, spectral analysis (IR, ~1H NMR, ~(13)C NMR, ~1H-~1H COSY, HMQC, HMBC, TOCSY, NOESY) and ESI-MS.
From the ethanolic extracts of B. marmorata, thirty-six triterpene glycosides were isolated and the structures were identified as the below, BM-1: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 25 (26)-holostene-3β, 12α-diol (named: 25,26-dehydro bivittoside D); BM-2: 3-O-{( 3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-gmcopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 24 (25)-holostene-3β, 12α, 17α-triol (named: 17-hydroxy impatiensideA); BM-3: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyr anosyl-(1-4)]-β-D-xylopyranosyl}-9 (11), 23 (24)-holostene-3β, 12a, 25-triol (named: marmoroside A); BM-4: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-25-acetoxy-9 (11)-holostene-3β, 12α-diol (named: 25-acetoxy bivittoside D); BM-5: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3) -β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyran osyl)-(1→3)-β- D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 24 (25)-holostene -3β, 12α-diol(impatienside A); BM-6: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosy 1)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11)-holostene-3β, 12α-diol (bivittoside D); BM-7: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyrano- syl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-12-one-9 (11)-holostene-3β-ol (named: marmoroside E);BM-8: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl -(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glu copyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 24 (25)-holostene-3β,12α, 22-triol (named:22-hydroxy impatienside A); BM-9: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3) -β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyran osyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-9 (11)-holostene-3β,12α, 17α-triol (named: marmoroside D); BM-10: 3-O-{(3-O-methyl-β-D-glucopy-ranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9(11)-holostene-3β,12α, 17α, 25-tetrol (named: marmoroside F); BM-11: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (named: marmoroside G); BM-12: 3-O-{(β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-2 2, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (named: marmoroside H); BM-13: 3-O-{( 3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylop yranosyl}-9 (11), 24 (25)-holostene-3β, 12α-diol (named: marmoroside I); BM-14: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-24-one-9 (11)-holostene-3β, 12α-diol (named: 24-one bivittoside D); BM-15: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-16-acetoxy-9 (11), 24 (25)-holostene-3β, 12α, 17α-triol (named: marmoroside J); BM-16: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D -glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β, 12α-diol (named: 17-dehydroxy marmoroside G); BM-17: 3-O-{(3-O-methyl-β-D-glucopyranosyl) -(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl -(1→4)]-β-D-xylopyranosyl}-23-acetoxy-9 (11), 24 (25)-holostene-3β, 12α-diol (named: marmoroside K); BM-18: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)] -β-D-xylopyrano syl}-23-acetoxy-9 (11), 24 (25)-holostene-3β,12α, 17α-triol (named: 17-hydroxy marmoroside K);BM-19: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xyIopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β,12α-diol (named: 17-dehydroxy holothurinoside A); BM-20:3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (holothurinoside A); BM-21: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-so diumsulfato-β-D-xylopyranosyl]-22-one-9 (11)-holostene-3β,12α-diol (fuscocineroside B );BM-22:3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22-one-25-acetoxy-9 (11)-holostene-3β,12α-diol (fuscocineroside A); BM-23: 3-O-[(3-O-methyl-β-D-gluco-pyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodium sulfato-β-D-xylopyranosyl]-22-one-25-acetoxy-9 (11)-holostene-3β, 12α, 17α-triol (named: marmoroside C); BM-24: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyr anosyl]-9 (11)-holostene-3β, 12α-diol(pervicoside C); BM-25: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-so diumsulfato-β-D-xylopyranosyl]-22-one-9 (11)-holostene-3β,12α, 17α-triol (named: 17-hydroxy fuscocineroside B); BM-26: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22-one-9 (11)-holostene-3β, 12α, 25-triol (named: 25-hydroxy fuscocineroside B); BM-27: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (holothurin A); BM-28: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α-diol (fuscocineroside C); BM-29: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D -quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-25-acetoxy-9 (11)-holostene-3β, 12α-diol (pervicoside A); BM-30: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-β-D-xylopyranosyl]-9 (11), 24 (25)-holostene-3β, 12α-diol (named: 24,25-dehydro marmoroside L); BM-31: 3-O-[(3 -O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-β-D-xylopyranosyl]-9 (11)-holostene-3β, 12α-diol (named: marmoroside L); BM-32:3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D -quinovopyranosyl-(1→2)-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol(DS-holothurin A); BM-33: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D -glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α-diol (named: marmoroside B); BM-34: 3-O-{β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyra nosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 24 (25)-holostene-3β,12α-diol(named: 24, 25-dehydro bivittoside B); BM-35: 3-O-{β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11)-holostene -3β,12α-diol (bivittoside B); BM-36: 3-O-[β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β,12α, 17α-triol (named:holothurin B).
From the ethanolic extracts of H. axiloga, twenty-one triterpene glycosides were isolatedand the structures were identified as the below, HA-1: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-7(8),25 (26)-holostene-3β-ol (stichloroside B2); HA-2: 3-O-{(3-O-methyl-β-D-glucopyranosyl) -(1→3)-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-7 (8)-holostene-3β-ol (stichloroside B1); HA-3: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-xylopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl) -(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-7 (8), 25 (26)-holostene-3β-ol (stichloroside C2); HA-4: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D -xylopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-( 1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-7 (8)-holostene-3β-ol (stichloroside C1); HA-5: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D -glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-7 (8)-holostene-3β-ol (named: axilogoside B); HA-6: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-xylopyranosyl -(1→4)-β-D-glucopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glu- copyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-7 (8)-holostene-3β-ol (named: axilogoside C); HA-7: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D -glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (marmoroside G); HA-8: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-xylopy -ranosyl-(1→4)-β-D-xylopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-9 (11)-holostene-3β,12α-diol (named: axilogoside D); HA-9: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-9 (11), 24 (25)-holostene-3β, 12α-diol (marmoroside K); HA-10: 3-O-{(3-Omethyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 24 (25)-holostene-3β, 12α-diol (named: axilogoside E); HA-11: 3-O-{(β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β, 12α-diol (axilogoside F); HA-12: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3) -β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-9 (11)-holostene-3β, 12α, 17α, 22-tetrol (holothurin A1); HA-13: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-9 (11)-holostene-3β, 12α, 17α-triol (echinoside A); HA-14: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-9(11)-holostene-3β, 12α-diol (pervicoside C); HA-15: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glu-copyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl] -22-one-9 (11)-holostene-3β, 12α-diol(fuscocineroside B); HA-16: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-so diumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (holothurin A);HA-17: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α-diol (ruscocineroside C); HA-18: 3-O-[(3-O-methyl-β-D-glucop-yranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22-one-25-acetoxy-9 (11)-holostene-3β, 12α-diol (fuscocineroside A);HA-19: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-25-acetoxy-9 (11)-holostene-3β, 12α-diol (pervicoside A); HA-20: 3-O-[β-D-quinovopyranosyl-(1→2 )-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (holothurin B); HA-21: 3-O-[β-D-quinovopyranosyl-(1→2)-4-O-sulfo-β-D-xylopyranosyl] -22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (axilogoside A).
BM-1; BM-2; BM-3; BM-4; BM-7; BM-8; BM-9; BM-10; BM-11; BM-12; BM-13; BM-14; BM-15; BM-16; BM-17; BM-18; BM-19; BM-23; BM-25; BM-26; BM-30; B-31; BM-33; BM-34 are novel triterpene glycosides isolated from B. marmorata. HA-5; HA-6; HA-8; HA-10; HA-21 are novel triterpene glycosides isolated from H. axiloga.
The antifungal active assay of these saponins indicated that BM-1; BM-2; BM-5; BM-6; BM-7; BM-13; BM-24; BM-30; BM-31; BM-34; BM-35; HA-13; HA-14 exhibit significant antifungal activities against Candida albicans. BM-1; BM-2; BM-4; BM-5; BM-6; BM-7; BM-13; BM-17; BM-19; BM-20; BM-24; BM-27; BM-30; BM-31; BM-34; BM-35; BM-36; HA-13; HA-14; HA-16; HA-20 exhibit significant antifungal activities against Cryptococcusneoformans. BM-1; BM-2; BM-5; BM-6; BM-13; BM-17; BM-24; BM-30; BM-31; BM-34; BM-35; HA-13; HA-14 exhibit significant antifungal activities against Aspergillusfumigatus. BM-1; BM-4; BM-5; BM-6; BM-9; BM-11; BM-17; BM-19; BM-20; BM-24; BM-30; BM-31; BM-32; BM-34; BM-35; HA-13; HA-14 exhibit significant antifungal activities against Trichophyton rubrum. BM-1; BM-2; BM-5; BM-6; BM-7; BM-13; BM-24; BM-30; BM-31; BM-34; BM-35; HA-13; HA-14 exhibit significant antifungal activities against Candida tropicalis. BM-2; BM-5; BM-6; BM-7; BM-13; BM-24; BM-30; BM-31; BM-34; BM-35; HA-13; HA-14 exhibit significant antifungal activities against Candida krusei, MIC_(80)≤4μg/ml.
The studied of the cytotoxic activities indicated that BM-1; BM-2; BM-5 and BM-6exhibit significant cytotoxic active against A549, while BM-24 exhibit considerable cytotoxicactive. BM-1; BM-2; BM-5 and BM-6 exhibit considerable cytotoxic active against MOLT-4.
Our studies focused on bioactive constituents of B. marmorata and H. axiloga have established a foundation for further research and development of these two sea cucumbers with abundant resources in South China Sea, and provided important leading compounds for the development of new antifungal drugs.
海参具有很高的药用价值，自古作为药用，《本草原始》记载：海参具“补肾精、益精髓、消痰涎、摄小便、壮阳、生百脉血、治溃疡”等功效。海参皂苷是海参的主要次生代谢产物，是海参主要活性化学成分，也是迄今为止唯一在动物体内发现的三萜皂苷类成分。药理研究表明，海参皂苷具有细胞毒、抗真菌、溶血等广泛生物活性。
作为本研究中心“海洋天然活性成分研究和新药开发”这一研究方向的子课题，本文主要介绍了图纹白尼参(Bohadschia marmorata Jaeger)和奇乳海参[Holothuria(Microthele)axiloga H．L．Clark]中三萜皂苷类成分的结构及生物活性研究。两种海参均生长分布于我国南海海域。早前日本学者曾对图纹白尼参的同物异名海参(Bohadschiabivittata Mitsukuri)做过研究，得到四个海参皂苷，并考查了其抗真菌活性，但目前尚未见有关奇乳海参体内皂苷类成分的研究报道。在本课题的研究中，作者应用硅胶、反相硅胶、葡聚糖凝胶等多种现代层析分离技术，对图纹白尼参及奇乳海参体内的三萜皂苷类成分进行了系统的分离纯化和药理研究，从图纹白尼参中分离鉴定了36个三萜皂苷化合物，从奇乳海参中分离鉴定了21个三萜皂苷化合物。应用现代光谱技术(尤其是2D-NMR)、ESI-MS技术和化学方法对这些化合物进行结构测定，确定了其化学结构和立体构型。其中新化合物共计26个。
从图纹白尼参中分离鉴定了36个三萜皂苷化合物，其化学结构鉴定如下，BM-1：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)，25(26)-海参烷烯-3β，12α-二醇(命名为：25，26-dehydro bivittoside D)；BM-2：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)，24(25)-海参烷烯-3β，12α，17α-三醇(命名为：17-hydroxyimpatienside A)；BM-3：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)，23(24)-海参烷烯-3β，12α，25-三醇(命名为：marmorosideA)；BM-4：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-25-乙酰氧基-9(11)-海参烷烯-3β，12α-二醇(命名为：25-acetoxy bivittoside D)；BM-5：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)，24(25)-海参烷烯-3β，12α-二醇(impatienside A)；BM-6：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)-海参烷烯-3β，12α-二醇(bivittoside D)；BM-7：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-12-羰基-9(11)-海参烷烯-3β-醇(命名为：marmoroside E)；BM-8：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)，24(25)-海参烷烯-3β，12α，22-三醇(命名为：22-hydroxy impatienside A)；BM-9：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-9(11)-海参烷烯-3β，12α，17α-三醇(命名为：marmoroside D)；BM-10：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)-海参烷烯-3β，12α，17α，25-四醇(命名为：marmoroside F)；BM-11：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基)-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(命名为：marmoro-side G)；BM-12：3-O-{(β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖-(1→4)]-β-D-吡喃木糖基}-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(命名为：marmoroside H)；BM-13：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃葡萄糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)，24(25)-海参烷烯-3β，12α-二醇(命名为：marmoroside I)；BM-14：3-O{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-24-羰基-9(11)-海参烷烯-3β，12α-二醇(命名为：24-one bivittosideD)；BM-15：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-16-乙酰氧基-9(11)，24(25)-海参烷烯-3β，12α，17α-三醇(命名为：marmoroside J)；BM-16：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-22，25-环氧-9(11)-海参烷烯-3β，12α-二醇(命名为：17-dehydroxy marmoroside G)；BM-17：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-9(11)，24(25)-海参烷烯-3β，12α-二醇(命名为：marmoroside K)；BM-18：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-9(11)，24(25)-海参烷烯-3β，12α，17α-三醇(命名为：17-hydroxymarmomside K)；BM-19：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-22，25-环氧-9(11)-海参烷烯-3β，12α-二醇(命名为：17-dehydroxy holothurinoside A)；BM-20：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(holothurinoside A)；BM-21：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22-羰基-9(11)-海参烷烯-3β，12α-二醇(fuscocineroside B)；BM-22：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)4-O-硫酸钠-β-D-吡喃木糖基]-22-羰基-25-乙酰氧基-9(11)-海参烷烯-3β，12α-二醇(fuscocineroside A)；BM-23：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22-羰基-25-乙酰氧基-9(11)-海参烷烯-3β，12α，17α-三醇(命名为：marmoroside C)；BM-24：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-9(11)-海参烷烯-3β，12α-二醇(pervicoside C)；BM-25：3-O[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22-羰基-9(11)-海参烷烯-3β，12α，17α-三醇(命名为：17-hydroxy fuscocineroside B)；BM-26：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基基]-22-羰基-9(11)-海参烷烯-3β，12α，25-三醇(命名为：25-hydroxyfuscocineroside B)；BM-27：3-O-](3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22，25-坏氧-9(11)-海参烷烯-3β，12α，17α-三醇(holothurin A)；BM-28：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22，25-环氧-9(11)-海参烷烯-3β，12α-二醇(fuscocineroside C)；BM-29：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-25-乙酰氧基-9(11)-海参烷烯-3β，12α-二醇(pervicoside A)；BM-30：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-β-D-吡喃木糖基]-9(11)，24(25)-海参烷烯-3β，12α-二醇(命名为：24，25-dehydro marmoroside L)；BM-31：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-β-D-吡喃木糖基]-9(11)-海参烷烯-3β，12α-二醇(命名为：marmoroside L)；BM-32：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-β-D-吡喃木糖基]-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(DS-holothurin A)；BM-33：3-O-[(3-D-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃葡萄糖-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22，25-环氧-9(11)-海参烷烯-3β，12α-二醇(命名为：marmoroside B)；BM-34：3-O-{β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)，24(25)-海参烷烯-3β，12α-二醇(命名为：24，25-dehydro bivittoside B)；BM-35：3-O-{β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)-海参烷烯-3β，12α-二醇(bivittoside B)；BM-36：3-O-[β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(命名为：holothurin B)。
从奇乳海参中分离鉴定了21个三萜皂苷化合物，其化学结构鉴定如下，HA-1：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃木糖基基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-7(8)，25(26)-海参烷烯-3β-醇(stichloroside B2)；HA-2：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃木糖基基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-7(8)-海参烷烯-3β-醇(stichloroside B1)；HA-3：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃木糖基基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-7(8)，25(26)-海参烷烯-3β-醇(stichloroside C2)；HA-4：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃木糖基基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-7(8)-海参烷烯-3β-醇(stichloroside C1)：HA-5：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃木糖基基-(1→4)-β-D-吡喃木糖基基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-7(8)-海参烷烯-3β-醇(命名为：axilogoside B)；HA-6：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃木糖基基-(1→4)-β-D-吡喃葡萄糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-βD-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-7(8)-海参烷烯-3β-醇(命名为：axilogoside C)；HA-7：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(marmoroside G)；HA-8：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃木糖基基-(1→4)-β-D-吡喃木糖基基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-9(11)-海参烷烯-3β，12α-二醇(命名为：axilogoside D)；HA-9：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-23-乙酰氧基-9(11)，24(25)-海参烷烯-3β，12α-二醇(marmoroside K)；HA-10：3-O-{(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-9(11)，24(25)-海参烷烯-3β，12α-二醇(命名为：axilogoside E)；HA-11：3-O-{(β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃木糖基}-22，25-环氧-9(11)-海参烷烯-3β，12α-二醇(axilogoside F)；HA-12：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)4-O-硫酸钠-β-D-吡喃木糖基]-9(11)-海参烷烯-3β，12α，17α，22-四醇(holothurin A1)；HA-13：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-9(11)-海参烷烯-3β，12α，17α-三醇(echinoside A)；HA-14：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-9(11)-海参烷烯-3β，12α-二醇(pervicoside C)；HA-15：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22-羰基-9(11)-海参烷烯-3β，12α-二醇(fuscocinerosideB)；HA-16：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)4-O-硫酸钠-β-D-吡喃木糖基]-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(holothurin A)；HA-17：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22，25-环氧-9(11)-海参烷烯-3β，12α-二醇(fuscocineroside C)；HA-18：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22-羰基-25-乙酰氧基-9(11)-海参烷烯-3β，12α-二醇(fuscocinero-side A)；HA-19：3-O-[(3-O-甲基-β-D-吡喃葡萄糖基)-(1→3)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-25-乙酰氧基-9(11)-海参烷烯-3β，12α-二醇(pervicoside A)；HA-20：3-O-[β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸钠-β-D-吡喃木糖基]-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(holothurin B)；HA-21：3-O-[β-D-吡喃奎诺糖基-(1→2)-4-O-硫酸-β-D-吡喃木糖基]-22，25-环氧-9(11)-海参烷烯-3β，12α，17α-三醇(axilogoside A)。
其中BM-1；BM-2；BM-3；BM-4；BM-7；BM-8；BM-9；BM-10；BM-11；BM-12；BM-13；BM-14；BM-15；BM-16；BM-17；BM-18；BM-19；BM-23；BM-25；BM-26；BM-30；BM-31；BM-33；BM-34为从图纹白尼参中得到的新海参皂苷类化合物；HA-5；HA-6；HA-8；HA-10；HA-21为从奇乳海参中得到的新海参皂苷类化合物。
抗真菌活性筛选表明：BM-1；BM-2；BM-5；BM-6；BM-7；BM-13；BM-24；BM-30；BM-31；BM-34；BM-35；HA-13；HA-14对白色念珠菌有很强的抑制活性；BM-1；BM-2；BM-4；BM-5；BM-6；BM-7；BM-13；BM-17；BM-19；BM-20；BM-24；BM-27；BM-30；BM-31；BM-34；BM-35；BM-36；HA-13；HA-14；HA-16；HA-20对新生隐球菌有很强的抑制活性；BM-1；BM-2；BM-5；BM-6；BM-13；BM-17；BM-24；BM-30；BM-31；BM-34；BM-35；HA-13；HA-14对薰烟曲霉菌有很强的抑制活性；BM-1；BM-4；BM-5；BM-6；BM-9；BM-11；BM-17；BM-19；BM-20；BM-24；BM-30；BM-31；BM-32；BM-34；BM-35；HA-13；HA-14对红色毛癣菌有很强的抑制活性；BM-1；BM-2；BM-5；BM-6；BM-7；BM-13；BM-24；BM-30；BM-31；BM-34；BM-35；HA-13；HA-14对热带念珠菌有很强的抑制活性；BM-2；BM-5；BM-6；BM-7；BM-13；BM-24；BM-30；BM-31；BM-34；BM-35；HA-13；HA-14对克鲁斯假丝酵母菌有很强的抑制活性。MIC_(80)值均≤4μg／ml，有进一步研究的价值。
体外细胞毒试验显示：BM-1；BM-2；BM-5和BM-6对A549人肺癌细胞株有强效细胞毒活性，而BM-24则显示弱效。BM-1；BM-2；BM-5和BM-6对MOLT-4人白血病细胞株显示弱效细胞毒活性。
本课题对图纹白尼参和奇乳海参的化学成分及其药理作用进行的系统深入研究，为进一步研制开发新的抗癌和抗真菌药物提供了科学依据和有价值的先导化合物，也为海洋天然产物的研究积累了新的研究资料，对开发利用我国丰富的海参生物资源具有较重要的意义。
Bohadschia marmorata Jaeger and Holothuria (Microthele) axiloga H.L.Clark are abundant sea cucumbers distributed in South China Sea. Japanese researchers had reported the structures and antifungal activityes of four new triterpene glycosides isolated from the sea cucumber Bohadschia bivittata Mitsukuri. But no chemical works have been performedon the sea cucumber Holothuria (Microthele) axiloga H.L.Clark up to date. The antifungalconstituents of B. marmorata and H. axiloga have been investigated by various chromatographymethods including LPLC, MPLC, HPLC on silica gel and ODS respectively. Fifty-seventriterpene glycosides were isolated, then the chemical structures of the twenty-eightnew compounds were elucidated by chemical reactions, spectral analysis (IR, ~1H NMR, ~(13)C NMR, ~1H-~1H COSY, HMQC, HMBC, TOCSY, NOESY) and ESI-MS.
From the ethanolic extracts of B. marmorata, thirty-six triterpene glycosides were isolated and the structures were identified as the below, BM-1: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 25 (26)-holostene-3β, 12α-diol (named: 25,26-dehydro bivittoside D); BM-2: 3-O-{( 3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-gmcopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 24 (25)-holostene-3β, 12α, 17α-triol (named: 17-hydroxy impatiensideA); BM-3: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyr anosyl-(1-4)]-β-D-xylopyranosyl}-9 (11), 23 (24)-holostene-3β, 12a, 25-triol (named: marmoroside A); BM-4: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-25-acetoxy-9 (11)-holostene-3β, 12α-diol (named: 25-acetoxy bivittoside D); BM-5: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3) -β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyran osyl)-(1→3)-β- D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 24 (25)-holostene -3β, 12α-diol(impatienside A); BM-6: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosy 1)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11)-holostene-3β, 12α-diol (bivittoside D); BM-7: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyrano- syl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-12-one-9 (11)-holostene-3β-ol (named: marmoroside E);BM-8: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl -(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glu copyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 24 (25)-holostene-3β,12α, 22-triol (named:22-hydroxy impatienside A); BM-9: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3) -β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyran osyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-9 (11)-holostene-3β,12α, 17α-triol (named: marmoroside D); BM-10: 3-O-{(3-O-methyl-β-D-glucopy-ranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9(11)-holostene-3β,12α, 17α, 25-tetrol (named: marmoroside F); BM-11: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (named: marmoroside G); BM-12: 3-O-{(β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-2 2, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (named: marmoroside H); BM-13: 3-O-{( 3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylop yranosyl}-9 (11), 24 (25)-holostene-3β, 12α-diol (named: marmoroside I); BM-14: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-24-one-9 (11)-holostene-3β, 12α-diol (named: 24-one bivittoside D); BM-15: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-16-acetoxy-9 (11), 24 (25)-holostene-3β, 12α, 17α-triol (named: marmoroside J); BM-16: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D -glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β, 12α-diol (named: 17-dehydroxy marmoroside G); BM-17: 3-O-{(3-O-methyl-β-D-glucopyranosyl) -(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl -(1→4)]-β-D-xylopyranosyl}-23-acetoxy-9 (11), 24 (25)-holostene-3β, 12α-diol (named: marmoroside K); BM-18: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)] -β-D-xylopyrano syl}-23-acetoxy-9 (11), 24 (25)-holostene-3β,12α, 17α-triol (named: 17-hydroxy marmoroside K);BM-19: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xyIopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β,12α-diol (named: 17-dehydroxy holothurinoside A); BM-20:3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (holothurinoside A); BM-21: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-so diumsulfato-β-D-xylopyranosyl]-22-one-9 (11)-holostene-3β,12α-diol (fuscocineroside B );BM-22:3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22-one-25-acetoxy-9 (11)-holostene-3β,12α-diol (fuscocineroside A); BM-23: 3-O-[(3-O-methyl-β-D-gluco-pyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodium sulfato-β-D-xylopyranosyl]-22-one-25-acetoxy-9 (11)-holostene-3β, 12α, 17α-triol (named: marmoroside C); BM-24: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyr anosyl]-9 (11)-holostene-3β, 12α-diol(pervicoside C); BM-25: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-so diumsulfato-β-D-xylopyranosyl]-22-one-9 (11)-holostene-3β,12α, 17α-triol (named: 17-hydroxy fuscocineroside B); BM-26: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22-one-9 (11)-holostene-3β, 12α, 25-triol (named: 25-hydroxy fuscocineroside B); BM-27: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (holothurin A); BM-28: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α-diol (fuscocineroside C); BM-29: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D -quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-25-acetoxy-9 (11)-holostene-3β, 12α-diol (pervicoside A); BM-30: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-β-D-xylopyranosyl]-9 (11), 24 (25)-holostene-3β, 12α-diol (named: 24,25-dehydro marmoroside L); BM-31: 3-O-[(3 -O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-β-D-xylopyranosyl]-9 (11)-holostene-3β, 12α-diol (named: marmoroside L); BM-32:3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D -quinovopyranosyl-(1→2)-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol(DS-holothurin A); BM-33: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D -glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α-diol (named: marmoroside B); BM-34: 3-O-{β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyra nosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 24 (25)-holostene-3β,12α-diol(named: 24, 25-dehydro bivittoside B); BM-35: 3-O-{β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11)-holostene -3β,12α-diol (bivittoside B); BM-36: 3-O-[β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β,12α, 17α-triol (named:holothurin B).
From the ethanolic extracts of H. axiloga, twenty-one triterpene glycosides were isolatedand the structures were identified as the below, HA-1: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-7(8),25 (26)-holostene-3β-ol (stichloroside B2); HA-2: 3-O-{(3-O-methyl-β-D-glucopyranosyl) -(1→3)-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-7 (8)-holostene-3β-ol (stichloroside B1); HA-3: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-xylopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl) -(1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-7 (8), 25 (26)-holostene-3β-ol (stichloroside C2); HA-4: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D -xylopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-( 1→3)-β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-7 (8)-holostene-3β-ol (stichloroside C1); HA-5: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D -glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-7 (8)-holostene-3β-ol (named: axilogoside B); HA-6: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-xylopyranosyl -(1→4)-β-D-glucopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glu- copyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-7 (8)-holostene-3β-ol (named: axilogoside C); HA-7: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D -glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (marmoroside G); HA-8: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-xylopy -ranosyl-(1→4)-β-D-xylopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-9 (11)-holostene-3β,12α-diol (named: axilogoside D); HA-9: 3-O-{(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-23-acetoxy-9 (11), 24 (25)-holostene-3β, 12α-diol (marmoroside K); HA-10: 3-O-{(3-Omethyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-9 (11), 24 (25)-holostene-3β, 12α-diol (named: axilogoside E); HA-11: 3-O-{(β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl}-22, 25-epoxy-9 (11)-holostene-3β, 12α-diol (axilogoside F); HA-12: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3) -β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-9 (11)-holostene-3β, 12α, 17α, 22-tetrol (holothurin A1); HA-13: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-9 (11)-holostene-3β, 12α, 17α-triol (echinoside A); HA-14: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-9(11)-holostene-3β, 12α-diol (pervicoside C); HA-15: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glu-copyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl] -22-one-9 (11)-holostene-3β, 12α-diol(fuscocineroside B); HA-16: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-so diumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (holothurin A);HA-17: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α-diol (ruscocineroside C); HA-18: 3-O-[(3-O-methyl-β-D-glucop-yranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-22-one-25-acetoxy-9 (11)-holostene-3β, 12α-diol (fuscocineroside A);HA-19: 3-O-[(3-O-methyl-β-D-glucopyranosyl)-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-quinovopyranosyl-(1→2)-4-O-sodiumsulfato-β-D-xylopyranosyl]-25-acetoxy-9 (11)-holostene-3β, 12α-diol (pervicoside A); HA-20: 3-O-[β-D-quinovopyranosyl-(1→2 )-4-O-sodiumsulfato-β-D-xylopyranosyl]-22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (holothurin B); HA-21: 3-O-[β-D-quinovopyranosyl-(1→2)-4-O-sulfo-β-D-xylopyranosyl] -22, 25-epoxy-9 (11)-holostene-3β, 12α, 17α-triol (axilogoside A).
BM-1; BM-2; BM-3; BM-4; BM-7; BM-8; BM-9; BM-10; BM-11; BM-12; BM-13; BM-14; BM-15; BM-16; BM-17; BM-18; BM-19; BM-23; BM-25; BM-26; BM-30; B-31; BM-33; BM-34 are novel triterpene glycosides isolated from B. marmorata. HA-5; HA-6; HA-8; HA-10; HA-21 are novel triterpene glycosides isolated from H. axiloga.
The antifungal active assay of these saponins indicated that BM-1; BM-2; BM-5; BM-6; BM-7; BM-13; BM-24; BM-30; BM-31; BM-34; BM-35; HA-13; HA-14 exhibit significant antifungal activities against Candida albicans. BM-1; BM-2; BM-4; BM-5; BM-6; BM-7; BM-13; BM-17; BM-19; BM-20; BM-24; BM-27; BM-30; BM-31; BM-34; BM-35; BM-36; HA-13; HA-14; HA-16; HA-20 exhibit significant antifungal activities against Cryptococcusneoformans. BM-1; BM-2; BM-5; BM-6; BM-13; BM-17; BM-24; BM-30; BM-31; BM-34; BM-35; HA-13; HA-14 exhibit significant antifungal activities against Aspergillusfumigatus. BM-1; BM-4; BM-5; BM-6; BM-9; BM-11; BM-17; BM-19; BM-20; BM-24; BM-30; BM-31; BM-32; BM-34; BM-35; HA-13; HA-14 exhibit significant antifungal activities against Trichophyton rubrum. BM-1; BM-2; BM-5; BM-6; BM-7; BM-13; BM-24; BM-30; BM-31; BM-34; BM-35; HA-13; HA-14 exhibit significant antifungal activities against Candida tropicalis. BM-2; BM-5; BM-6; BM-7; BM-13; BM-24; BM-30; BM-31; BM-34; BM-35; HA-13; HA-14 exhibit significant antifungal activities against Candida krusei, MIC_(80)≤4μg/ml.
The studied of the cytotoxic activities indicated that BM-1; BM-2; BM-5 and BM-6exhibit significant cytotoxic active against A549, while BM-24 exhibit considerable cytotoxicactive. BM-1; BM-2; BM-5 and BM-6 exhibit considerable cytotoxic active against MOLT-4.
Our studies focused on bioactive constituents of B. marmorata and H. axiloga have established a foundation for further research and development of these two sea cucumbers with abundant resources in South China Sea, and provided important leading compounds for the development of new antifungal drugs.
引文
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[1]廖玉麟编著：《中国动物志棘皮动物门海参纲》，北京：科学出版社，1997．
[2] Z. R. Zou, Y. H. Yi, Q. Z. Xu, et al. A New Disulfated Triterpene Glycoside from theSea Cucumber Mensamaria intercedens Lam pert. Chinese Chemical Letters 2003,14 (6), 585.
[3] Z. R. Zou, Y. H. Yi, H. M. Wu, et al. Intercedensides A-C, Three New Cytotoxic Triterpene Glycosides from the Sea Cucumber Mensamaria intercedens Lampert. J. Nat. Prod. 2003, 66, 1055.
[4] Z. R. Zou, Y. H. Yi, H. M. Wu, et al. Intercedenol A and B, Two New Triterpenoids from the Sea Cucumber M ensamaria tercedens. Chinese Chemical Letters 2004, 75 (3), 309.
[5] S. L. Zhang, L. Li, Y. H. Yi, et al. Philinopgenin A, B, and C, Three New Triterpenoid Aglycones from the Sea Cucumber Pentacta quadrangulasis. Mar. Drugs 2004, 2, 185.
[6] Z. R. Zou, Y. H. Yi, H. M. Wu, et al. Intercedensides D-I, Cytotoxic Triterpene Glycosides from the Sea Cucumber Mensamaria intercedens Lampert. J. Nat. Prod. 2005, 68, 540.
[7] Y. H. Yi, Q. Z. Xu, L. Li, et al. Philinopsides A and B, Two New Sulfated Triterpene Glycosides from the Sea Cucumber Pentacta quadrangularis. Helvetica Chimica Acta 2006, 89, 54.
[8] S. L. Zhang, L. Li, Y. H. Yi, et al. Philinopsides E and F, two new sulfated triterpene glycosides from the sea cucumber Pentacta quadrangularis. Natural Product Research 2006, 20 (4), 399.
[9] J. Wu, Y. H. Yi, H. F. Tang, et al. Structure and Cytotoxicity of a New Lanostane-Type Tnterpene Glycoside from the Sea Cucumber Holothuria hilla. Chemistry & Biodiversity 2006, 3, 1249.
[10] S. L. Zhang, Y. H. Yi, L. Li, et al. Two new bioactive triterpene glycosides from the sea cucumber Pseudocolochirus violaceus. Journal of Asian Natural Products Research 2006,5(1-2), 1.
[11] S.Y. Zhang, Y.H. Yi, H.F. Tang. Bioactive Triterpene Glycosides from the Sea Cucumber Holothuria fuscocinerea. J. Nat. Prod. 2006, 69, 1492.
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[15] P. Sun, B. S. Liu, Y. H. Yi, et al. A New Cytotoxic Lanostane-Type Triterpene Glycoside from the Sea Cucumber Holothuria impatiens. Chemistry & Biodiversity 2007, 4, 450.
[16] W. H. Yuan, Y. H. Yi, L. Li, et al. Two triterpene glycosides from the sea cucumber Bohadschia marmorata Jaeger. Chinese Chemical Letters 2008,19, 457.
[17] W. H. Yuan, Y. H. Yi, M. Xue, et al. Two Antifungal Active Triterpene Glycosides from the Sea Cucumber Holothuria (Microthele) axiloga. Chin. J. Nat. Med. 2008, 6, 105.
[18] I. Kitagawa, M. Kobayashi, T. Inamoto, et al. Marine nature products XIV. Structures of echinoside A and B, antifungal lanostane-oligosides from the sea cucumber Actinopyga echinites (Jaeger). Chem. Pharm. Bull. 1985, 33, 5214.
[19] I. Kitagawa, M. Kobayashi, M. Hori, et al. Marine Natural Products. ⅩⅧ . Four Lanostane-Type Triterpene Oligoglycosides, Bivittosides A, B, C, and D, from the Okinawan Sea Cucumber Bohadschia bivittata MITSUKURI. Chem. Pharm. Bull. 1989, 37, 61.
[20] E. Breitmaier, W. Voelter Carbon-13 NMR Spectroscopy, VCH, Weinheim, 1987.
[21] I. Kitagawa, M. Kobayashi, B. M. Son, et al. Marine natural products. XIX. Pervico-sides A, B, and C, lanostane-type triterpene-oligoglycoside sulfates from the sea cucumber Holothuria pervicax Chem. Pharm. Bull. 1989, 37, 1230.
[22] J. Rodriguez, R. Castro and R. Riguera. Holothurinosides: New Antitumor Non Sulphated Triterpenoid Glycosides From The Sea Cucumber Holothuria Forskalii. Tetrahedron 1991, 47 (26), 4753.
[23] Stonik VA, Maltsev II, Kalinovaky AI, et al. Glycosides of marine invertebrates. XL Two new triterpene glycosides from sea cucumbers belonging to the family Stichopodidae. Khim. Prir. Soedin., 1982, 194.
[24] I. Kitagawa, M. Kobayashi, T. Inamoto, et al. The structure of six ahtifungal oligoglycosides, stichlorosides A1, A2, B1, B2, C1, and C2, from the sea cucumber Stichopus chloronotus (Brant). Chem. Pharm. Bull. 1981, 29 (8): 2387.
[25] I. I. Maltsev, V. A. Stonik and A. I. kalinovsky. Glycosides of marine invertebrates. Structure of new triterpene glycoside from sea cucumbers belonging to the family Stichopodidae - stichoposide E. Khim. Prir. Soedin., 1983, 308.
[26] G. K. Oleinikova, T. A. Kuznetsova, N.S. Ivanova, et al. Glycosides of marine invertebrates. XV. A new triterpene glycoside - Holothurin A_1 - From Caribbean holothurians of the family Holothuriidae. Chem Nat Comd. 1983,18 (4):430.
[27] V. I. Kalinin and V. A. Stonik. Glycosides of the holothurian Bohadschia graeffei. Chem Nat Comd. 1983,18 (6), 758.
[2] Isao K, Motomasa K, Tatsuya I, et al. Marine nature products XIV. Structures ofechinoside A and B, antifungal lanostane-oligosides from the sea cucumber Actinopygaechinites (Jaeger) [J]. Chem. Pharm. Bull. 1985, 33 (12): 5214.
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[16] Kalinin VI and Stonik VA. Glycosides of the holothurian Bohadschia graeffei [J]. Chem Nat Comd., 1983, 18 (6):758.
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[18] Ivanova NS, Smetanina OF, Kuznetsova TA. Glycosides of marine invertebrates. XXVI. Holothurin A from the Pacific Ocean holothurian Holothvria squamifera [J]. Chem Nat Comd., 1985, 20 (4):422.
[19] Zhang SY, Yi YH, Tang HF. Bioactive triterpene glycosides from the sea cucumber Holothuria fuscocinerea [J]. J Nat Prod., 2006, 69 (10):1492.
[20] Kitagawa I, kobayashi M, Son BW, et al. Marine natural products. XIX. Pervicosides A, B, and C, lanostane-type triterpene-oligoglycoside sulfates from the sea cucumber Holothuria pervicax [J]. Chem Pharm Bull, 1989, 37 (5): 1230.
[21] W. H. Yuan, Y. H. Yi, L. Li, et al. Chin. Chem. Lett. 2008,19, 457.
[22] 翁怡毅,易杨华,李玲,等。Chin. J. Nat. Med. 2007, 5 (2), 96.
[23] P. Sun, B. S. Liu, Y. H. Yi Chemistry & Biodiversity 2007, 4, 450.
[1]廖玉麟编著：《中国动物志棘皮动物门海参纲》，北京：科学出版社，1997．
[2] Z. R. Zou, Y. H. Yi, Q. Z. Xu, et al. A New Disulfated Triterpene Glycoside from theSea Cucumber Mensamaria intercedens Lam pert. Chinese Chemical Letters 2003,14 (6), 585.
[3] Z. R. Zou, Y. H. Yi, H. M. Wu, et al. Intercedensides A-C, Three New Cytotoxic Triterpene Glycosides from the Sea Cucumber Mensamaria intercedens Lampert. J. Nat. Prod. 2003, 66, 1055.
[4] Z. R. Zou, Y. H. Yi, H. M. Wu, et al. Intercedenol A and B, Two New Triterpenoids from the Sea Cucumber M ensamaria tercedens. Chinese Chemical Letters 2004, 75 (3), 309.
[5] S. L. Zhang, L. Li, Y. H. Yi, et al. Philinopgenin A, B, and C, Three New Triterpenoid Aglycones from the Sea Cucumber Pentacta quadrangulasis. Mar. Drugs 2004, 2, 185.
[6] Z. R. Zou, Y. H. Yi, H. M. Wu, et al. Intercedensides D-I, Cytotoxic Triterpene Glycosides from the Sea Cucumber Mensamaria intercedens Lampert. J. Nat. Prod. 2005, 68, 540.
[7] Y. H. Yi, Q. Z. Xu, L. Li, et al. Philinopsides A and B, Two New Sulfated Triterpene Glycosides from the Sea Cucumber Pentacta quadrangularis. Helvetica Chimica Acta 2006, 89, 54.
[8] S. L. Zhang, L. Li, Y. H. Yi, et al. Philinopsides E and F, two new sulfated triterpene glycosides from the sea cucumber Pentacta quadrangularis. Natural Product Research 2006, 20 (4), 399.
[9] J. Wu, Y. H. Yi, H. F. Tang, et al. Structure and Cytotoxicity of a New Lanostane-Type Tnterpene Glycoside from the Sea Cucumber Holothuria hilla. Chemistry & Biodiversity 2006, 3, 1249.
[10] S. L. Zhang, Y. H. Yi, L. Li, et al. Two new bioactive triterpene glycosides from the sea cucumber Pseudocolochirus violaceus. Journal of Asian Natural Products Research 2006,5(1-2), 1.
[11] S.Y. Zhang, Y.H. Yi, H.F. Tang. Bioactive Triterpene Glycosides from the Sea Cucumber Holothuria fuscocinerea. J. Nat. Prod. 2006, 69, 1492.
[12] S. Y. Zhang, H. F. Tang, Y. H. Yi. Cytotoxic triterpene glycosides from the sea cucumber Pseudocolochirus violaceus. Fitoterapia 2007, 78, 283.
[13] Y. Y. Wen, Y. H. Yi, L. Li, et al. 沙海参中的三个海参皂苷. Chin. J. Nat. Med. 2007, 5, 96.
[14] Han H, Yi YH, Li L, et al. A new triterpene glycoside from sea cucumber Holothuria leucospilota. Chinese Chemical Letters 2007,18, 161.
[15] P. Sun, B. S. Liu, Y. H. Yi, et al. A New Cytotoxic Lanostane-Type Triterpene Glycoside from the Sea Cucumber Holothuria impatiens. Chemistry & Biodiversity 2007, 4, 450.
[16] W. H. Yuan, Y. H. Yi, L. Li, et al. Two triterpene glycosides from the sea cucumber Bohadschia marmorata Jaeger. Chinese Chemical Letters 2008,19, 457.
[17] W. H. Yuan, Y. H. Yi, M. Xue, et al. Two Antifungal Active Triterpene Glycosides from the Sea Cucumber Holothuria (Microthele) axiloga. Chin. J. Nat. Med. 2008, 6, 105.
[18] I. Kitagawa, M. Kobayashi, T. Inamoto, et al. Marine nature products XIV. Structures of echinoside A and B, antifungal lanostane-oligosides from the sea cucumber Actinopyga echinites (Jaeger). Chem. Pharm. Bull. 1985, 33, 5214.
[19] I. Kitagawa, M. Kobayashi, M. Hori, et al. Marine Natural Products. ⅩⅧ . Four Lanostane-Type Triterpene Oligoglycosides, Bivittosides A, B, C, and D, from the Okinawan Sea Cucumber Bohadschia bivittata MITSUKURI. Chem. Pharm. Bull. 1989, 37, 61.
[20] E. Breitmaier, W. Voelter Carbon-13 NMR Spectroscopy, VCH, Weinheim, 1987.
[21] I. Kitagawa, M. Kobayashi, B. M. Son, et al. Marine natural products. XIX. Pervico-sides A, B, and C, lanostane-type triterpene-oligoglycoside sulfates from the sea cucumber Holothuria pervicax Chem. Pharm. Bull. 1989, 37, 1230.
[22] J. Rodriguez, R. Castro and R. Riguera. Holothurinosides: New Antitumor Non Sulphated Triterpenoid Glycosides From The Sea Cucumber Holothuria Forskalii. Tetrahedron 1991, 47 (26), 4753.
[23] Stonik VA, Maltsev II, Kalinovaky AI, et al. Glycosides of marine invertebrates. XL Two new triterpene glycosides from sea cucumbers belonging to the family Stichopodidae. Khim. Prir. Soedin., 1982, 194.
[24] I. Kitagawa, M. Kobayashi, T. Inamoto, et al. The structure of six ahtifungal oligoglycosides, stichlorosides A1, A2, B1, B2, C1, and C2, from the sea cucumber Stichopus chloronotus (Brant). Chem. Pharm. Bull. 1981, 29 (8): 2387.
[25] I. I. Maltsev, V. A. Stonik and A. I. kalinovsky. Glycosides of marine invertebrates. Structure of new triterpene glycoside from sea cucumbers belonging to the family Stichopodidae - stichoposide E. Khim. Prir. Soedin., 1983, 308.
[26] G. K. Oleinikova, T. A. Kuznetsova, N.S. Ivanova, et al. Glycosides of marine invertebrates. XV. A new triterpene glycoside - Holothurin A_1 - From Caribbean holothurians of the family Holothuriidae. Chem Nat Comd. 1983,18 (4):430.
[27] V. I. Kalinin and V. A. Stonik. Glycosides of the holothurian Bohadschia graeffei. Chem Nat Comd. 1983,18 (6), 758.
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