Department of Biology, University of Massachusetts Boston, MA 02125, USA.
Mar Drugs. 2010 Dec 6;8(12):2906-35. doi: 10.3390/md8122906.
The amino acid, tyrosine, and its hydroxylated product, 3,4-dihydroxyphenylalanine (dopa), plays an important role in the biogenesis of a number of potentially important bioactive molecules in marine organisms. Interestingly, several of these tyrosyl and dopa-containing compounds possess dehydro groups in their side chains. Examples span the range from simple dehydrotyrosine and dehydrodopamines to complex metabolic products, including peptides and polycyclic alkaloids. Based on structural information, these compounds can be subdivided into five categories: (a) Simple dehydrotyrosine and dehydrotyramine containing molecules; (b) simple dehydrodopa derivatives; (c) peptidyl dehydrotyrosine and dehydrodopa derivatives; (d) multiple dehydrodopa containing compounds; and (e) polycyclic condensed dehydrodopa derivatives. These molecules possess a wide range of biological activities that include (but are not limited to) antitumor activity, antibiotic activity, cytotoxicity, antioxidant activity, multidrug resistance reversal, cell division inhibition, immunomodulatory activity, HIV-integrase inhibition, anti-viral, and anti-feeding (or feeding deterrent) activity. This review summarizes the structure, distribution, possible biosynthetic origin, and biological activity, of the five categories of dehydrotyrosine and dehydrodopa containing compounds.
氨基酸酪氨酸及其羟基化产物 3,4-二羟基苯丙氨酸（多巴）在海洋生物中许多潜在重要生物活性分子的生物合成中发挥着重要作用。有趣的是，这些含酪氨酸和多巴的化合物中有几种在其侧链中含有脱氢基团。这些例子从简单的脱羟酪氨酸和脱羟多巴胺到复杂的代谢产物，包括肽和多环生物碱，涵盖了广泛的范围。根据结构信息，这些化合物可以分为五类：（a）含简单脱羟酪氨酸和脱羟酪胺的分子；（b）简单脱羟多巴衍生物；（c）肽基脱羟酪氨酸和脱羟多巴衍生物；（d）多种含脱羟多巴的化合物；和（e）多环缩合脱羟多巴衍生物。这些分子具有广泛的生物学活性，包括（但不限于）抗肿瘤活性、抗生素活性、细胞毒性、抗氧化活性、多药耐药逆转、细胞分裂抑制、免疫调节活性、HIV 整合酶抑制、抗病毒和抗食（或拒食）活性。本文综述了五类含脱羟酪氨酸和脱羟多巴的化合物的结构、分布、可能的生物合成来源和生物学活性。
