12 0 0 0 OA 新任教官紹介
- 著者
- 菅原 孝太郎 北村 嘉章 佐竹 真幸 村田 道雄 橘 和夫
- 出版者
- 天然有機化合物討論会実行委員会
- 雑誌
- 天然有機化合物討論会講演要旨集
- 巻号頁・発行日
- vol.53, pp.433-438, 2011
Our continuous efforts for search of new bioactive compounds led to isolation of a polyene-polyol, prorocentrol, from P. hoffmannianum (CCMP 683). Although a ketone-hemiacetal tautomerism was observed during the course of NMR measurements, NMR measurements in pyridine-d_5/D_2O (6:1) at room temperature gave simplified NMR spectra. Detailed COSY and TOCSY analyses led to four 114 spin-networks, which were constructed to gross structure on the basis of HMBC correlations. The stereoconfigurational analysis of prorocentrol was undertaken by extensive utilization of 2D-NMR methods. The conformation of cyclic ethers in the molecule was analyzed based on NOESY correlations and ^3J_<H,H・> A JBCA method was applied for elucidation of the relative configurations of chiral centers in acyclic portions. Where HETLOC did not give sufficient intensity, qualitative utilization of the relationship between HMBC signal intensity and corresponding ^<2,3>J_<C,H> turned out to be effective especially for the methyl bearing portions. Moreover, the universal NMR database method was also applied on the continuous polyol segments as an alternative way for the JBCA to reveal the relative configuration. As a particular property of prorocentrol, suggestive evidences for an association of prorocentrol and okadaic acid were indicated from chromatographic behaviors and changes of NMR chemical shifts.
1 0 0 0 OA ウシノシタ魚類のサメ忌避物質
- 著者
- 橘 和夫
- 出版者
- The Society of Synthetic Organic Chemistry, Japan
- 雑誌
- 有機合成化学協会誌 (ISSN:00379980)
- 巻号頁・発行日
- vol.45, no.9, pp.898-908, 1987-09-01 (Released:2009-11-13)
- 参考文献数
- 48
- 被引用文献数
- 1 2
Two classes of shark repellent factors have been isolated, guided by their ichthyotoxicity, from the defense secretions of two species of soles. One class comprises series of steroid monoglycosides, namely, pavoninins from a western Pacific species, Pardachirus pavoninus, and mosesins from the other in the Red Sea known as Moses sole, P. marmoratus. The other class consists of a series of surfactant peptides of 33 amino acid residues, pardaxins. This account deals with structure elucidation of these factors, where emphasis is put on the process from inference of chemical structures by spectroscopic and other customary techniques to their establishment by design of unconventional but firmly corroborative experiments. Diverse bioactivity of these factors is also discussed based on rationale with their amphiphilic structures, which are destined to interact with biological lipid bilayer membranes.