Halichondria species

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]. 

A sterol disulfate (534) and a sterol trisulfate (535), both closely related to halistanol, have been found in a species of Halichondria [447] and in Trachyopsis halichondrioides [448] respectively. 

A Japanese species of Epipolasis contained five sterol sulfates named halistanol sulfates A-E (536-540), which differ from the original halistanol sulfate (532) from Halichondria moorei [449]. Structures were elucidated by spectroscopic and chemical techniques. Halistanol sulfates F-H (541-543) are three additional sterol sulfates from Pseudaxinyssa digitata that inhibit HIV in vitro [450]. 

The tridecapeptide polydiscamide A (309) was obtained from an unidentified Caribbean species of Discodermia [220], while discodermins A-H (298-305) were isolated from D. kiiensis. The structures deduced previously for discodermins A-E [221, 222] were later revised on the basis of NMR data and protein sequence analysis [223]. A number of closely related compounds, the tetradecapeptides halicylindramides A-C (306-308) [224], the tridecapeptide halicylindramide D (310) [225], and the truncated linear peptide halicylindramide E [225] (311) were obtained from the sponge Halichondria cylindrata. A microbial origin for these compounds was suggested [226]. 

Amagata T, Doi M, Ohta T, Minoura K, Numata A (1998) Absolute Stereostructures of Novel Cytotoxic Metabolites, Gymnastatins A-E, from a Gymnascella Species Separated from a Halichondria Sponge. J Chem Soc Perkin Trans 1 3585... 

One sponge species found in many coastal zones is the breadcrumb sponge (Halichondria panicea). Green to yellow crusts of the sponge creep across rocks and can cover an area of several feet. Breadcrumb sponges can be found as thin mats in the energetic surf zones, but in quiet tide pools, they form thicker masses. 

The common crust of bread sponge, Halichondria panicea, was found to contain large amounts of sulfur compounds, notably dimethyl trisulfide (171), to such an extent that the organism was considered hazardous to handle by the fishermen in the area. Samples of this species collected at other localities were found to contain trace amounts of the sulfur compounds. 

Hahchondrins, and in particular halichondrin B, homo-hahchondrin B, and iso-homohalichondrin B, have been observed only in fotir sponge species Halichondria okadai (1986), Axinella sp. (1991), Phakdlia carteri (1993), and the... 

Amagata, T, Doi, M., Ohta, T, Minoura, K and Numata, A. (1998c) Absolute stereostructure of novel cytotoxic metabolites, gynmastatins A-E, from a Gymnascella species separated from a Halichondria sponge. J. Chem. Soc. Perkin Trans. /, 3585-3599. 

Amagata, T, Tanaka, M., Yamada, T., Minoiua, K., and Nmnata, A. (2008) Gymnastatins and dankastatins, growth inhibitory metabolites of a Gymnascella species from a Halichondria sponge. /. Nat. Prod., 71, 340-345. 

Halichonadin A is a rare example of a sesquiterpene dimer (eudesmane) associated with a molecule of urea. This compound has been isolated from an imdetermined species of the genus Halichondria of Japanese origin (Okinawa) with halichonadins B-D, which contain the... 

A few halidiondrid sponges, such as Pseudaxinyssa sp., contain sterols substituted at 24 with an isopropyl group (Figure 19.20), and this relatively rare feature of the side chains occurs in an Epipolasis sp. harvested in Japan and in Ciocalypta sp. collected in Senegal (Do et al, 2009). This species contains polasterol A, polasterol B sulfate and 24-isopropylcholesterol, as well as halistanol sulfate, which was isolated in 1981 from Halichondria sp., also of... 

Concerning sulfur-containing compounds, it is worth mentioning halichondria sulfonic acid, an rmusual derivative of the rare N-methyltaurine and guanidine but already known as a synthetic compormd. This derivative was isolated from the Chinese species Halichondria rugosa. Isolated along with hahstanol sulfate, halichondria sulfonic acid is an HIV-1 inhibitor (Jin et al., 2006). 

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