Halichondria sponge isothiocyanates from

The structure of a diterpenoid isothiocyanate (276) extracted from a Halichondria sponge, was determined from chemical and spectral data [277]. 

Nakamura, H., Deng, S., Takamatsu, M., Kobayashi, J., Ohizumi, Y, and Hirata, Y. (1991) Structure of halipanidne, a new sesquiterpene isothiocyanate from the Okinawan sponge Halichondria panicea (Pallas). Agric. Biol Chem., 55, 581-583. 

A Halichondria species of sponge from Oahu, Hawaii contained a complex mixture of sesqui- and diterpenoids. The sesquiterpenoids belonged to the a-amorphene (zizanene) series and included an isothiocyanate (239) [248]. 

A species of Halichondria from the Marshall Islands contained an isothiocyanate (249) [255] and an isothiocyanate based on the guai-6-ene skeleton (250) was isolated from an unidentified sponge from Japanese waters [256]. Acanthella pulcherrima from Australia contained two isothiocyanates (251-252), in addition to known sesquiterpenes [257]. 

Two acyclic diterpene tetraene isothiocyanates have been isolated from sponges so far. Famesyl isothiocyanate (220) was obtained from Pseudaxinyssa pitys [184] while compound (+)-221 was isolated from Halichondria sp. [185]. Their structures were elucidated by interpretation of their spectral data. 

Compounds containing the isocyano group have fascinated natural products chemists ever since the first isocyanide xanthocillin was isolated from the fungus Penicillium notatum Westling in 1950 [1]. The existence of sesquiterpene isocyanides was first reported from the Mediterranean sponge Axinella cannabina in 1973 [2], closely followed by sesquiterpene isocyanides from the Mediterranean sponge Acanthella acuta by Minale et al. [3] and the Hawaiian sponge Halichondria sp. by Scheuer et al. [4]. These early reports also documented the presence of isothiocyanate [2] and formamide [4] functionality attached to the same carbon nucleus as the... 

---