四株南海肉芝软珊瑚共附生真菌次级代谢产物及其化学生态作用与药理活性
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摘要
珊瑚礁生态系统是热带海洋中最大的生态系统，种类繁多，数量庞大的海底生物充分利用珊瑚礁生态系统有限的生存资源，且高压、高盐、缺氧、避光等较特殊的海洋生态环境，也使得各种生物对食物、空间的竞争异常激烈。软珊瑚等许多海洋低等无脊椎动物，固着生长，体质柔软，缺乏有效的物理防御手段，却能够在残酷的海洋环境中安然生存，正是依靠其化学防御机制。目前已经从软珊瑚中发现了一批具有拒捕食、防附着、克生、抗微生物等化学防御作用的化合物，有些具有药物开发潜力。值得关注的是，软珊瑚中的化学防御物质不仅具有重要的化学生态学意义，而且部分化合物在药理学方面也表现了较好的活性。因此探讨化学生态作用与药理活性之间的关系，对海洋的新药发现具有一定的启迪作用。研究发现，海洋无脊椎动物中的共附生微生物可能参与了宿主的化学生态学活性化合物的生物合成如海葵毒素，芋螺毒素等。因此，通过比较共附生微生物与宿主次级代谢产物之间的关系，来探讨共附生微生物在宿主化学防御中的作用，已成为海洋化学生态学研究的兴奋点。
本研究对一种中国南海肉芝软珊瑚Sarcophyton sp.(GX-WZ-20080011)中分离获得的15株共附生真菌，在化学防御活性模型指导下，选择4株共附生真菌，链格孢属真菌(Alternaria sp.)，曲霉属真菌(Aspergillus elegans和Aspergillus versicolor)和扁孔腔菌属真菌(Lophiostoma sp.)，进行发酵培养。采用化学防御活性追踪分离的方法，对真菌发酵产物综合运用硅胶柱层析、凝胶柱层析与半制备HPLC等分离手段，利用理化性质和NMR, MS, IR, UV, X-ray和CD等波谱学技术，并结合化学方法，从中分离鉴定了79个化合物(1–79)的结构，其中18个为新化合物。涉及8种结构类型，包括蒽醌类化合物(24个)，苯醌类化合物(5个)，含氮化合物(20个)，萜类化合物(5个)，内酯类化合物(5个)，甾体(7个)，芳香族化合物(11个)和脂肪族化合物(2个)。对显示多种生物活性的蒽醌类化合物10,12和蒽醌二聚体类化合物21,22和24进行了化学修饰，通过乙酰基、甲基、苯甲酰基、苄基及脂肪链取代获得系列衍生物20个(10a–c,12a–g,20a–c,21a–d,24a–b)。通过化学方法Mosher法确定了氢化蒽醌类化合物的绝对构型；通过X-ray单晶衍射确定了化合物8和9的相对构型；发现了蒽醌二聚体类化合物新的连接方式，确定了蒽醌二聚体化合物新的连接方式；同时初步探讨了共附生真菌与宿主软珊瑚代谢产物结构及活性之间的关系。
运用化学生态学活性模型（抗藤壶幼虫附着、抑藻活性、斑马鱼胚胎毒性等）对化合物进行了活性筛选，发现具有生态活性活性化合物12个，如苯醌类化合物25显示较强的抗藤壶附着活性，EC50为0.27μg/mL。并对活性化合物进行了初步构效关系的探讨。在评价化学生态活性同时进行药理活性(细胞毒、抗菌、抗病毒等)评价，并初步探讨化合物的构效关系。在活性测试中，发现化合物10,12和39等化合物不仅显示较好的化学生态学活性，而且还具有较强的药理活性。其中，蒽醌类化合物10对斑马鱼胚胎的48h尾部致畸EC50值达到2.40μg/mL，对斑马鱼72h致死IC50值达到2.91μg/mL；对米氏凯伦藻K.mikimotoi的生长抑制活性达到1.16μg/mL；同时，对5种肿瘤细胞肝癌细胞(HepG2和Hep3B),乳腺癌阿霉素耐药细胞(MCF-7/ADR)，前列腺癌细胞(PC-3)和结肠癌细胞(HT-116)均显示较强的细胞毒性，IC50值达到0.70–2.85μg/mL，其中对HCT-116的IC50值达到0.70μg/mL，接近阳性对照药表阿霉素0.48μg/mL。
本研究在化学生态学作用的指导下，从一种肉芝软珊瑚来源的4株共附生真菌中追踪分离获得多种结构类型的活性天然产物，并对活性蒽醌类化合物进行结构修饰获得系列衍生物；用化学方法确定氢化蒽醌类化合物绝对构型；初步探讨了共附生微生物在宿主肉芝软珊瑚化学防御中的作用，对海洋药物先导化合物的筛选和发现具有启示作用。
The coral reef ecosystem is the largest ecosystem in the tropical ocean, a widerange and a huge number of marine life make full use of limited resources for survivalin the coral reef ecosystems, and the marine ecology have a high pressure, high salt,hypoxia, protected from light and other special environmental characteristics, whichmake the fierce competition between the various marine organisms such as fightingfor biological food and space. Soft corals and many other marine invertebrates havesoft, fleshy and fragile tissues without physical defense capability against theirpotential predators. However, they can survive in the competitive environmentsbecause of their chemical defensive system. In the last few years, many new chemicaldefensive compounds such as antifeeding, antifouling, allelopathy and anti-microbialwere obtained from soft coral, and some of them have shown potentials to beexploited as marine drugs. It is noted that the chemical defense compounds in the softcoral is not only important chemical and ecological significance, and somecompounds also showed potent pharmacological activity. Therefore, to explore therelationship between the chemical ecology activity and pharmacological activity, havea certain enlightening to find new marine drugs. The microorganisms isolated frommarine ivertebrates may be involved in the biosynthesis of active chemical ecologycompounds in the host, such as sea anemone toxins, conotoxins. Consequently,according to comparison the secondary metabolites to research the relationshipbetween microorganisms and the host, and to explore the effect of the microorganismsin the host chemical defense has become the excitement of marine chemical ecology.
In this study,15epiphytic fungi was isolated from the soft coral Sarcophyton sp.(GX-WZ-20080011), which was collected from the South China Sea, under theguidance of the chemical defense activity model, four epiphytic fungi includingAlternaria sp., Aspergillus elegans, Aspergillus versicolor and Lophiostoma sp. wereselect for fermentation. The secondary metabolites were isolated by column chromatography on silica gel, Sephadex LH-20and preparative HPLC, and identifiedby spectroscopy of NMR, MS, IR, UV, X-ray, CD and chemical methods. From theseorganisms,79compounds (1–79) were respectively determined, including18newcompounds. More than8structural types were found, including24anthraquinones,5benzoquinones,20nitrogen compounds,5terpenoids,7steroids,11aromaticcompounds, and2lipids.20derivatives of anthraquinones (10a–b,12a–g,20a–c,21a–c,24a–b) have been prepared by acetylation, methylation, propionyl, benzyl forfurther research on structure and activity relationships.
The chemical ecology effects including antifouling activity against the larvaesettlement of barnacle, growth-inhibition of microalgae and toxicity against zebrafishwere used to find active compounds.13compound were found to have ecologicalactivity, such as benzoquinones25shows strong anti-barnacle adhesion activity, withEC50value of0.27μg/mL.Pharmacological activity were also evluated and to explorethe structure-activity relationship.
Compounds10,12and39were found to have not only significance in chemicalecology but also various pharmacological activities. Such as compound10displayed48h tail teratogenicity of zebrafish at the concentrate of2.4μg/mL,72h death ofzebrafish at the concentrate of2.91μg/mL; and potent growth-inhibition activitytowards microalgae with EC50of1.16μg/mL. In addition to the chemical ecologyactivity, this compound showed strong cytotoxicity toward five tumor cells, ashepatoma cells (HepG2and Hep3B), breast cancer adriamycin-resistant cells(MCF-7/ADR) and prostate cancer (PC-3) and colon cancer cells (HT-116), with theIC50values of0.70–2.85μg/mL, and the IC50value of HCT-116to0.70μg/mL isclose to the positive control drug epirubicin to0.48μg/mL. The structure and activityrelationships of these compound were discussed.
In this study, under the guidance of the chemical ecological models, a variety ofstructural types of bioactive natural products were isolated from four softcoral-derived epiphytic fungi, and the anthraquinones which had potent activity wereprepared to to obtain series of derivatives.
The absolute configuration of the hydrogenated anthraquinones were determinedby chemical methods. The relationship between chemical ecology activity andpharmacological activity of the active compounds was preliminary discussed. It is thefirst time to investigate the the role of microorganisms in the chemical defense ofthe soft coral Sarcophyton sp. All these results provide basis for finding the lead compounds of marine drugs, the further studies on chemical ecology and exploring forfinding new medicinal bioresources.
本研究对一种中国南海肉芝软珊瑚Sarcophyton sp.(GX-WZ-20080011)中分离获得的15株共附生真菌，在化学防御活性模型指导下，选择4株共附生真菌，链格孢属真菌(Alternaria sp.)，曲霉属真菌(Aspergillus elegans和Aspergillus versicolor)和扁孔腔菌属真菌(Lophiostoma sp.)，进行发酵培养。采用化学防御活性追踪分离的方法，对真菌发酵产物综合运用硅胶柱层析、凝胶柱层析与半制备HPLC等分离手段，利用理化性质和NMR, MS, IR, UV, X-ray和CD等波谱学技术，并结合化学方法，从中分离鉴定了79个化合物(1–79)的结构，其中18个为新化合物。涉及8种结构类型，包括蒽醌类化合物(24个)，苯醌类化合物(5个)，含氮化合物(20个)，萜类化合物(5个)，内酯类化合物(5个)，甾体(7个)，芳香族化合物(11个)和脂肪族化合物(2个)。对显示多种生物活性的蒽醌类化合物10,12和蒽醌二聚体类化合物21,22和24进行了化学修饰，通过乙酰基、甲基、苯甲酰基、苄基及脂肪链取代获得系列衍生物20个(10a–c,12a–g,20a–c,21a–d,24a–b)。通过化学方法Mosher法确定了氢化蒽醌类化合物的绝对构型；通过X-ray单晶衍射确定了化合物8和9的相对构型；发现了蒽醌二聚体类化合物新的连接方式，确定了蒽醌二聚体化合物新的连接方式；同时初步探讨了共附生真菌与宿主软珊瑚代谢产物结构及活性之间的关系。
运用化学生态学活性模型（抗藤壶幼虫附着、抑藻活性、斑马鱼胚胎毒性等）对化合物进行了活性筛选，发现具有生态活性活性化合物12个，如苯醌类化合物25显示较强的抗藤壶附着活性，EC50为0.27μg/mL。并对活性化合物进行了初步构效关系的探讨。在评价化学生态活性同时进行药理活性(细胞毒、抗菌、抗病毒等)评价，并初步探讨化合物的构效关系。在活性测试中，发现化合物10,12和39等化合物不仅显示较好的化学生态学活性，而且还具有较强的药理活性。其中，蒽醌类化合物10对斑马鱼胚胎的48h尾部致畸EC50值达到2.40μg/mL，对斑马鱼72h致死IC50值达到2.91μg/mL；对米氏凯伦藻K.mikimotoi的生长抑制活性达到1.16μg/mL；同时，对5种肿瘤细胞肝癌细胞(HepG2和Hep3B),乳腺癌阿霉素耐药细胞(MCF-7/ADR)，前列腺癌细胞(PC-3)和结肠癌细胞(HT-116)均显示较强的细胞毒性，IC50值达到0.70–2.85μg/mL，其中对HCT-116的IC50值达到0.70μg/mL，接近阳性对照药表阿霉素0.48μg/mL。
本研究在化学生态学作用的指导下，从一种肉芝软珊瑚来源的4株共附生真菌中追踪分离获得多种结构类型的活性天然产物，并对活性蒽醌类化合物进行结构修饰获得系列衍生物；用化学方法确定氢化蒽醌类化合物绝对构型；初步探讨了共附生微生物在宿主肉芝软珊瑚化学防御中的作用，对海洋药物先导化合物的筛选和发现具有启示作用。
The coral reef ecosystem is the largest ecosystem in the tropical ocean, a widerange and a huge number of marine life make full use of limited resources for survivalin the coral reef ecosystems, and the marine ecology have a high pressure, high salt,hypoxia, protected from light and other special environmental characteristics, whichmake the fierce competition between the various marine organisms such as fightingfor biological food and space. Soft corals and many other marine invertebrates havesoft, fleshy and fragile tissues without physical defense capability against theirpotential predators. However, they can survive in the competitive environmentsbecause of their chemical defensive system. In the last few years, many new chemicaldefensive compounds such as antifeeding, antifouling, allelopathy and anti-microbialwere obtained from soft coral, and some of them have shown potentials to beexploited as marine drugs. It is noted that the chemical defense compounds in the softcoral is not only important chemical and ecological significance, and somecompounds also showed potent pharmacological activity. Therefore, to explore therelationship between the chemical ecology activity and pharmacological activity, havea certain enlightening to find new marine drugs. The microorganisms isolated frommarine ivertebrates may be involved in the biosynthesis of active chemical ecologycompounds in the host, such as sea anemone toxins, conotoxins. Consequently,according to comparison the secondary metabolites to research the relationshipbetween microorganisms and the host, and to explore the effect of the microorganismsin the host chemical defense has become the excitement of marine chemical ecology.
In this study,15epiphytic fungi was isolated from the soft coral Sarcophyton sp.(GX-WZ-20080011), which was collected from the South China Sea, under theguidance of the chemical defense activity model, four epiphytic fungi includingAlternaria sp., Aspergillus elegans, Aspergillus versicolor and Lophiostoma sp. wereselect for fermentation. The secondary metabolites were isolated by column chromatography on silica gel, Sephadex LH-20and preparative HPLC, and identifiedby spectroscopy of NMR, MS, IR, UV, X-ray, CD and chemical methods. From theseorganisms,79compounds (1–79) were respectively determined, including18newcompounds. More than8structural types were found, including24anthraquinones,5benzoquinones,20nitrogen compounds,5terpenoids,7steroids,11aromaticcompounds, and2lipids.20derivatives of anthraquinones (10a–b,12a–g,20a–c,21a–c,24a–b) have been prepared by acetylation, methylation, propionyl, benzyl forfurther research on structure and activity relationships.
The chemical ecology effects including antifouling activity against the larvaesettlement of barnacle, growth-inhibition of microalgae and toxicity against zebrafishwere used to find active compounds.13compound were found to have ecologicalactivity, such as benzoquinones25shows strong anti-barnacle adhesion activity, withEC50value of0.27μg/mL.Pharmacological activity were also evluated and to explorethe structure-activity relationship.
Compounds10,12and39were found to have not only significance in chemicalecology but also various pharmacological activities. Such as compound10displayed48h tail teratogenicity of zebrafish at the concentrate of2.4μg/mL,72h death ofzebrafish at the concentrate of2.91μg/mL; and potent growth-inhibition activitytowards microalgae with EC50of1.16μg/mL. In addition to the chemical ecologyactivity, this compound showed strong cytotoxicity toward five tumor cells, ashepatoma cells (HepG2and Hep3B), breast cancer adriamycin-resistant cells(MCF-7/ADR) and prostate cancer (PC-3) and colon cancer cells (HT-116), with theIC50values of0.70–2.85μg/mL, and the IC50value of HCT-116to0.70μg/mL isclose to the positive control drug epirubicin to0.48μg/mL. The structure and activityrelationships of these compound were discussed.
In this study, under the guidance of the chemical ecological models, a variety ofstructural types of bioactive natural products were isolated from four softcoral-derived epiphytic fungi, and the anthraquinones which had potent activity wereprepared to to obtain series of derivatives.
The absolute configuration of the hydrogenated anthraquinones were determinedby chemical methods. The relationship between chemical ecology activity andpharmacological activity of the active compounds was preliminary discussed. It is thefirst time to investigate the the role of microorganisms in the chemical defense ofthe soft coral Sarcophyton sp. All these results provide basis for finding the lead compounds of marine drugs, the further studies on chemical ecology and exploring forfinding new medicinal bioresources.
引文
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