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首页> 外文学位 >Chemistry of Caribbean octocorals of the order Gorgonacea: Isolation, structural elucidation, and chemical modification of their secondary metabolites.
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Chemistry of Caribbean octocorals of the order Gorgonacea: Isolation, structural elucidation, and chemical modification of their secondary metabolites.

机译：加勒比八角ace科八角珊瑚的化学性质：其次生代谢产物的分离，结构解析和化学修饰。

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摘要

The study of five Caribbean gorgonian species culminated with the discovery of forty-two (42) new secondary metabolites. Briareum asbestinum, Erythropodium caribaeorum, Eunicea fusca, Plexaura flexuosa, and Pseudopterogorgia elisabethae are common inhabitants of Caribbean waters. The study of their chemical constituents was accomplished on the basis of spectroscopic and chromatographic techniques. After extraction, the crude extracts of these organisms were purified using chromatographic techniques until the pure components were isolated. The structure elucidation of the compounds was performed by exhaustive analyses of the spectroscopic data recorded which included ultraviolet (UV), infrared (IR), nuclear magnetic resonance (NMR), and mass spectrometry (MS) experiments. The application of 2D-NMR techniques and high resolution MS was required to rigorously establish the structures. Also, X-ray diffraction analysis was employed to confirm the structure of crystalline solids.;Briareum asbestinum is well known for its ability to produce asbestinane, eunicellane, and briarane diterpenoids. In our study, we discovered eighteen (18) new briarane diterpenoids from the chloroform extract of B. asbestinum. These metabolites possess a highly oxidized skeleton and are characterized by the presence of multiple ester groups. Although the briarein diterpenoids are known to exhibit a wide array of bioactivities, we have not detected any significant biological properties for these compounds.;Three new fuscosides were discovered from Eunicea fusca, along with two non-glycosidic metabolites. Fuscosides F and G are a pair of glycosilated geometric isomers at Delta11,12. While fuscoside E and fuscanin represent compounds with new carbon skeletons that could stem from the known fuscoside A upon oxidative cleavage, 15-methoxyfuscol is a methoxylated derivative of fuscol. Fuscoside E and fuscanin displayed mild analgesic properties during a series of antiinflammatory assays.;The Caribbean sea whip Pseudopterogorgia elisabethae represents an excellent source of secondary metabolites because of the abundance and structural variety of the compounds isolated from it. As part of this study, we isolated sixteen (16) new metabolites belonging to at least fourteen (14) different structural classes, eight of them representing new carbon skeletons. The new carbon frameworks appear to be biosynthetically related to the serrulatane carbon skeleton upon undergoing further cyclizations and oxidative rearrangements. Some of the new compounds exhibited biological activity.;Cembranoids are among the most common diterpenoids isolated from natural sources. Several cembranoids were isolated from the gorgonian Plexaura flexuosa. The structures of these compounds were elucidated by spectroscopic techniques. Also, chemical modifications were performed to the known cembranolide 12,13-bisepi-ieupalmerin in order to produce synthetic derivatives that would display interesting biological properties. So far, preliminary reports pertaining to the biological activities of such synthetic cembranolide analogs look very promising.
机译：对五种加勒比高粱物种的研究最终达到了发现四十二（42）种新的次生代谢产物的高潮。加勒比海水域常见的动物有：Breaareum asbestinum，Erythropodium caribaeorum，Eunecea fusca，Plexaura flexuosa和Pseudopterogorgia elisabethae。在光谱和色谱技术的基础上完成了对它们化学成分的研究。提取后，使用色谱技术纯化这些生物的粗提物，直到分离出纯净的成分。通过详尽分析所记录的光谱数据进行化合物的结构阐明，这些光谱数据包括紫外线（UV），红外线（IR），核磁共振（NMR）和质谱（MS）实验。严格建立结构需要2D-NMR技术和高分辨率MS的应用。此外，还使用X射线衍射分析来确认晶体固体的结构。天牛果（Briareum asbestinum）以其生产天冬氨酸，松香油和天环烷二萜的能力而闻名。在我们的研究中，我们从山形芽孢杆菌的氯仿提取物中发现了十八（18）种新的芳烃二萜。这些代谢物具有高度氧化的骨架，其特征是存在多个酯基。尽管已知Briariin二萜类化合物具有广泛的生物活性，但我们尚未发现这些化合物具有任何重要的生物学特性。;从真叶草中发现了三种新的岩藻糖苷，以及两种非糖苷代谢物。岩藻糖苷F和G是在Delta11,12处的一对糖基化的几何异构体。岩藻糖苷E和富斯坎宁代表具有新碳骨架的化合物，这些碳骨架可能源自已知的岩藻糖苷A氧化裂解后，而15-甲氧基岩藻糖醇是岩藻糖醇的甲氧基化衍生物。 Fuscoside E和fuscanin在一系列抗炎试验中显示出温和的镇痛作用。加勒比海鞭子Pseudopterogorgia elisabethae是次生代谢产物的极好来源，因为从中分离出的化合物丰富且结构多样。作为这项研究的一部分，我们分离了十六（16）种新代谢产物，它们至少属于十四（14）种不同的结构类别，其中八种代表新的碳骨架。在经历进一步的环化和氧化重排后，新的碳骨架似乎与舒拉拉坦碳骨架生物合成相关。一些新化合物表现出生物活性。蝶形类化合物是从天然来源分离的最常见的二萜类化合物。从高粱的Plexaura flexuosa中分离出了几种类柏树。通过光谱技术阐明了这些化合物的结构。另外，对已知的西巴洛内酯12，13-双isepieupalmerin进行了化学修饰，以产生具有令人感兴趣的生物学特性的合成衍生物。到目前为止，有关这种合成西班诺内酯类似物的生物活性的初步报道看起来非常有前途。

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  • 作者

    Ramirez Melendez, Catherine.;

  • 作者单位

    University of Puerto Rico, Rio Piedras (Puerto Rico).;

  • 授予单位 University of Puerto Rico, Rio Piedras (Puerto Rico).;
  • 学科 Biology Oceanography.;Chemistry Organic.
  • 学位 Ph.D.
  • 年度 2000
  • 页码 211 p.
  • 总页数 211
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类
  • 关键词

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