The Nitrogenous Hamigerans: Unusual Amino Acid-Derivatized Aromatic Diterpenoid Metabolites from the New Zealand Marine Sponge Hamigera tarangaensis
The Nitrogenous Hamigerans: Unusual Amino Acid-Derivatized Aromatic Diterpenoid Metabolites from the New Zealand Marine Sponge Hamigera tarangaensis
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DOI：
10.1021/jo502370b
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发表时间：
2015-01-02
影响因子：
3.6
通讯作者：
Northcote, Peter T.
中科院分区：
文献类型：
--
作者：
Dattelbaum, Jonathan D.;Singh, A. Jonathan;Northcote, Peter T.
描述了来自新西兰海洋海绵 Hamigera tarangaensis 的九种新含氮 hamigeran 二萜化合物的 NMR 指导分离和结构解析。该组的特色是含恶唑的 hamigeran M (4) 和八种与 hamigeran D (1) 结构相关的化合物（5a-6a 和 7a-8c）。据报道，七种新化合物在低微摩尔范围内对 HL-60 早幼粒细胞白血病细胞系具有中等细胞毒性。这些化合物的结构性质表明它们的加合物源自氨基酸源，并且允许将原型化合物 hamigeran D 的 C-18 构型从 1a 修改为 1b。 hamigeran Q (8a-8c) 的三种结构相同形式的存在需要同种异亮氨酸立体异构体的参与，并表明这些不寻常的次级代谢产物的部分原核生物发生的有趣可能性。
The NMR-directed isolation and structure elucidation of nine new nitrogenous hamigeran diterpenoids from the New Zealand marine sponge Hamigera tarangaensis are described. Featured in this set are the oxazole-containing hamigeran M (4) and eight compounds (5a-6a and 7a-8c) related to the constitutional structure of hamigeran D (1). Moderate cytotoxicity in the low-micromolar range against the HL-60 promyeloid leukemic cell line is reported for seven of the new compounds. The structural nature of these compounds suggests that their adducts are derived from an amino acid source and has allowed for revision of the configuration about C-18 of the archetypal compound, hamigeran D, from 1a to 1b. The existence of three constitutionally identical forms of hamigeran Q (8a-8c) requires the involvement of an allo-isoleucine stereoisomer and suggests the intriguing possibility of partial prokaryotic biogenesis of these unusual secondary metabolites.