Kahalalides V-Y isolated from a Hawaiian collection of the sacoglossan mollusk Elysia rufescens.

Kahalalides V-Y isolated from a Hawaiian collection of the sacoglossan mollusk Elysia rufescens.
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Kahalalides V-Y 从夏威夷的 Sacoglossan 软体动物 Elysia rufescens 中分离出来。

DOI:
10.1021/np070508g
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发表时间:
2008
影响因子:
5.1
通讯作者:
Hamann,MarkT
Hamann,MarkT
中科院分区:
生物学2区
文献类型:
--
作者:
Rao,KarumanchiV;Na,MinKyun;Cook,JenniferC;Peng,Jiangnan;Matsumoto,Rae;Hamann,MarkT

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本文报道了四个新的kahalalides,V(1),W(2),X(3)和Y(4),以及六个已鉴定的kahalalides。奇怪的是,以前弗罗姆. rufescens,被发现基本上没有从这些集合,尽管相同的收集地点和时间与以前的集合。此外,迄今为止仅从Bryopsissp.在这个集合中发现了E。rufescens,这表明这些代谢物的产生可能来自与软体动物和藻类的微生物联合,这种关系随着环境和捕食的变化而不断发展。新肽的结构已经建立在广泛的1D和2D NMR光谱数据分析的基础上。Kahalalide V(1)是Kahalalide D(5)的无环衍生物,而Kahalalide W(2)是由4-羟基-L-脯氨酸取代5中的脯氨酸。Kahalalide C的无环衍生物Kahalalide X(3)的精氨酸残基经测定为L构型。Kahalalide Y(4)中的羟脯氨酸被脯氨酸取代。这是明确的,从这个集合的E。rufescens认为,发现新的卡哈拉利相关代谢物仍然是高度可行的。
Four new kahalalides, V (1), W (2), X (3), and Y (4), as well as six previously characterized kahalalides have been isolated from a two-year collection of the sacoglossan molluskElysia rufescens. Curiously, kahalalide B, previously isolated in high yield fromE. rufescens, was found to be essentially absent from these collections despite identical collection sites and times with previous collections. In addition, kahalalide K, which to date has only been reported fromBryopsissp., was found in this collection ofE. rufescens, suggesting that the production of these metabolites could potentially be from a microbial association with the mollusk and algae, and this relationship is continuously evolving in response to changes in the environment and predation. The structures of new peptides have been established on the basis of extensive 1D and 2D NMR spectroscopic data analysis. Kahalalide V (1) was ascertained to be an acyclic derivative of kahalalide D (5), while kahalalide W (2) was determined to have a 4-hydroxy-l-proline residue instead of the proline in5. The arginine residue of kahalalide X (3), an acyclic derivative of kahalalide C, was determined to have anlconfiguration. Kahalalide Y (4) was found to have anl-proline residue instead of the hydroxyproline in kahalalide K. It is clear from this collection ofE. rufescensthat the discovery of new kahalalide-related metabolites is still highly feasible.