Aplysia kurodai

While little biosynthetic information is available, it has been suggested [38] that 25 and 26 may be formed from AA (24) and EPA (14) via a cyclization mechanism (Scheme 3) similar to that which forms trans-cyclopropyl-containing diol 28 upon treatment of linoleic acid with performic acid [40]. An alternative biogenetic mechanism (Scheme 4), based upon that proposed for the structurally related red algal metabolites constanolactone A and B [41], would involve the formation and opening of an allylic epoxide intermediate created as a result of a 15-/ -LPO acting on either AA or EPA. Related compounds have been isolated from the coral Plexaura homomalla and the mollusc Aplysia kurodai (see below). 

FIGURE 2.3 Glycosaminoglycans resources of some kinds of sea slugs. (A) Melibe viridis, (B) Aplysia kurodai, (C) Gtossodoris rufomarginata. Adapted from http //www.umiushi. info/. 

The brominated alkaloid neoaplaminone sulfate (196) was isolated from the sea hare Aplysia kurodai and its structure was determined by spectral and chemical methods [186]. A. kurodai obtains most, if not all of its metabolites from the red algae on which it feeds [10]. 

From the sea hare Aplysia kurodai, belonging to the subclass Prosobran-chia, two phosphonoglycolipids having complex, carbohydrate chains have also been isolated.143"146 One of the lipids contains one residue each of sphingosine base, fatty acid, glucose, 2-acetamido-2-deoxygalactose, and... 

A collection of Laurencia elata from the coast of Victoria has provided the pyrano[3,2-7>]pyranyl vinyl acetylene elatenyne (666) (772), which is related to the known (Z)-dactomelyne (7). Japonenynes A (667), B (668), and C (669), which possess a furo[3,2-h]pyranyl framework, were isolated from Laurencia japonensis (773). Compound 669 may be an isolation (methanol) artifact although it is isolated as a single compound. The report of aplysiallene from the sea hare Aplysia kurodai (774) is erroneous and this compound is actually a known bromoallene (775) described earlier (7). The Vietnamese Laurencia pannosa contains pannosallene (670), which is closely related to the known laurallene... 

Tsukamoto S, Yamashita Y, Ohta T (2005) New Cytotoxic and Antibacterial Compounds Isolated from the Sea Hare, Aplysia kurodai. Mar Drugs 3 22... 

Okamoto Y, Nitanda N, Ojika M, Sakagami Y (2001) Aplysiallene, a New Bromoallene as an Na, K-ATPase Inhibitor from the Sea Hare, Aplysia kurodai. Biosci Biotechnol Biochem 65 474... 

Aplysia kurodai IC50 = 31 uM F-actin disruption = 0.48ng/mL HeLa S3 human cervical... 

The complete chemical and. ST-ray studies of laurinterol (140) have been published. In addition to laurinterol, debromolaurinterol and isolaurinterol (141) are also found in Laurencia intermedia Yamada. Aplysin (142), isolated from Aplysia kurodai Baba, can be derived from laurinterol by acid-catalysed cyclisation. A synthesis of both aplysin and debromoaplysin, involving suitable elaboration of the alcohol (143) has been reported.The synthesis of the methyl... 

Peribysins C and D were initially reported in 2004 as diastereomers that functioned as potent cell adhesion inhibitors from the fungus Periconia byssoides separated from the sea hare Aplysia kurodai These compounds... 

A potent antitumor compound, aplyronine A (64), was first isolated from the sea hare Aplysia kurodai off the Pacific coast of Mie Prefecture, Japan. Aplyronine A (64) exhibited a high degree of antitumor activity in vivo against P388 murine leukemia (77C 545%, 0.08 mg/kg), Lewis lung carcinoma TIC = 556%,... 

Yamada, K., Ojika, M., Ishigaki, T., Yoshida, Y, Ekimoto, H., and Arakawa, M. (1993). Aplyro-nine A, a potent antitumor substance, and the congeners aplyronines B and C isolated from the sea hare Aplysia kurodai. J. Am. Chem. Soc. 115, 11020-11021. 

Synthesis and antitumor activity of actin-depolymerizing macrolides from the sea hare Aplysia kurodai 06Y1273. 

Aplaminone and Neoaplaminone. Three brominated, cytotoxic alkaloids have been isolated from the marine mollusc, Aplysia kurodai, and their structures elucidated using inverse-detected NMR methods (Kigoshi et al. 1990). The authors report using a combination of COLOC and HMBC spectra for long-range connectivities utilized in the structure elucidation of these molecules. Unfortunately, no details of the correlations actually observed in the HMBC spectrum were given in their communication. The structure of aplaminone (50) is shown. 

R648 F. Morishita, Y. Furukawa and O. Matsushima, NdWFamide A D-Amino Acid Containing Neuropeptide of an Opistobranch Gastropod, Aplysia Kurodai , Hikaku Seiri Seikagaku, 2011, 28, 308. 

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