Axinyssa

In a recent study, a Fijian sponge, Axinyssa fenestratus, was found to elaborate four isothiocyanatoamorphanes (43-46) [45]. That this series of compounds may be antipodal to 32 from the Hawaiian Halichondria sp. was indicated by the spectral and optical data of 43 [(1 R,6S,1S, 1 OS)- 10-isocyanato-4-amorphene]. 

Isothiocyanatocubebane (128) and 10-isothiocyanatoguaia-6-ene (129) were isolated from a Palau sponge, Axinyssa aplysinoides, which is rich in isocyano-related sesquiterpenoids [44, 49]. The former (128) is apparently related to the amorphanes (Sect. 4.1.3) and the latter (129) to the aromaden-dranes [Sect. 4.1.5]. 

The structure of 5-isothiocyanatopupukeanane (257), a sesquiterpene isothiocyanate from an Axinyssa species from Guam, was determined by X-ray analysis [260]. Two isomeric sesquiterpene thiocyanates, 2-thiocyanatoneopupukeanane (258) and 4-thiocyanatoneopupukeanane (259) were isolated from an unidentified sponge from Pohnpei and from Phycopsis terpnis from Okinawa [261]. A sample of Axinyssa (= Trachyopsis) aplysinoides from Palau yielded a rare thiocyanate, 2-thiocyanatopupukeanane (260), while two specimens from Pohnpei yielded 13-isothiocyanatocubebane (261), 1-isothiocyanatoaromadendrane (262) and 2-thiocyanatoneopupukeanane (258) [262]. This last compound had previously been assigned different stereochemistry at C2 [261]. (-)-4-Thiocyanatoneopupukeanane has been synthesised in an enantiospecific manner (259) [263]. Both enantiomers of 2-thiocyanatoneopupukeanane (258) have been synthesised from (7 )-carvone [264]. 

Three new antiparasitic sesquiterpene isothiocyanates, 4-isothiocyanato-9-amorphene (264), 10-isothiocyanato-4,6-amorphadiene (265) and 10-isothiocyanato-5-amorphen-4-ol (266) were isolated from a Fijian specimen of Axinyssa fenestratus. The compounds were identified by spectral data interpretation [268]. Two isomeric isothiocyanates (267-268) were isolated from Acanthella klethra from the Great Barrier Reef and their structures were determined by X-ray crystallography and spectral data examination [269]. 

A sesquiterpene thiocyanate, cavemothiocyanate (269) was isolated from Acanthella cf. cavernosa and the structure was elucidated on the basis of spectral data. The nudibranch Phyllidia ocellata also contained cavemothiocyanate [270]. Acanthene B (270) is a sesquiterpene isothiocyanate isolated from a British Columbian Acanthella sp. [271]. The sesquiterpene thiol, T-cadinthiol (271) was isolated from Cymbastela hooperi from Kelso Reef on the Great Barrier Reef [272]. A sesquiterpene isothiocyanate that displayed modest in vitro antimalarial activity, (-)-9-isothiocyanatopupukeanane (272) was isolated from an Axinyssa sp. from the Great Barrier Reef [273]. Great Barrier Reef samples of A. cavernosa contained 10-isothiocyanatocadin-4-ene (273) [274],... 

IR,6S, 7S,10S)-10-isothiocyanato-4-amorphene Axinyssa fenestratus [168] Anthelmintic activity... 

Hirota H, Okino T, Yoshimura E, Fusetani N (1998) Five New Antifouling Sesquiterpenes from Two Marine Sponges of the Genus Axinyssa and the Nudibranch Phyllidia pustulosa. Tetrahedron 54 13971... 

Hirota, H., Okino, T., Yoshimura, E., and Fusetani, N., Five new antifouling sesquiterpenes from two marine sponges of the genus Axinyssa and the nudibranch Phyllidia pustuiosa, Tetrahedron, 54, 13971, 1998. 

Sillen LG (1967) How have seawater and air got their present compositions Chem Br 1 291-297 Simpson JS, Garson MJ (2004) Biosynthetic pathways to isocyanides and isothiocyanates precursor incorporation studies on terpene metabohtes in the tropical marine sponges Amphimedon terpenensis and Axinyssa n.sp. J Org Biomol Chem 2 939-948... 

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