Halichondria genus

The first marine isocyano metabolite was appropriately named axisonitrile-1 (1) based on the trivial name isonitrile and the genus of the sponge, Axinella cannabina, which also furnished axisothiocyanate-1 (2) [1] and, subsequently, a minor constituent, axamide-1 (3) [5]. This observation that isonitriles are often accompanied by isothiocyanates (-N=C=S) and formamides (-NHCHO) was later duplicated by the Hawaiian researchers working with a Halichondria sp. In... 

Tachibana, K., et al., Okadaic acid, a cytotoxic polyether from two marine sponges of the genus Halichondria, JACS, 103, 2469, 1981. 

Halistanol sulfate (532) from Halichondria cf. moorei is a tris-sodium sulfate salt, which possesses antimicrobial, hemolytic, and ichthyotoxic activity [444]. It was later isolated from two sponges of the genus Topsentia as the free sterol and found to inhibit pp60v-src protein tyrosine kinase activity [445]. The tris(2-aminoimidazolium) salt of halistanol sulfate (533) was isolated from Topsentia sp. from Japan and is also antimicrobial [446]. 

The antifungal macrolide halichondramide (3), isolated from the Kwajalein sponge of the genus Halichondria, showed significant insecticidal activity at 3 ppm, especially against tobacco budworm. We isolated swinholides A (4) and B (5), from the Red Sea sponge The-onella swinhoei. 

Tachibana, K., Scheuer, P.J., Tsukitani, Y, Kikuchi, H., Van Engen, D, Clardy, I, Gopichand, Y, and Schmitz, EJ. 1981. Okadaic acid, a cytotoxic polyether from two marine sponges of the genus Halichondria. J Am Chem Soc 103, 2469-2471. 

The sponge Halichondria okadai contains a polyether metabohte named okadaic acid (16) that was also isolated as a causative agent of diarrhetic shellfish poisoning (DSP) from mussels and other bivalves (14). However, the real producers are dinoflagellates of the genus Dinophysis. It is a potent cancer promoter that was found to be caused by inhibition of protein phosphatases 1 and 2A at nanomolar levels. Pectenotoxins are also involved in DSP and are produced by Dinophysis spp. pectenotoxin 2 (17) inhibits actin polymerization (14). 

In 1988 the Faulkner group reported the results of a comprehensive study of the macrocyclic metabolites of the nudibranch Hexabranchus sanguineus and sponges of the genus Halichondria. Specimens of the nudibranch collected from subtidal reefs at Kwajalein Atoll, Marshal Islands, were found to contain (76) dihydrohalichondramide [92], tetrahydrohalichondramide [93] and kabiramide C [91]. Both 92 and 93 were also found in the eggmasses of the nudibranch (77). It is noteworthy... 

The antifungal macrolide halichondramide (3), isolated by Kernan et al. from the Kwa-jalein sponge of the genus Halichondria, showed the most significant in vitro activity of the compounds tested. With 50% inhibitory concentration (IC50) values approaching those for compounds used clinically, this marine natural product is a potential lead for the development of alternative chemotherapy for the treatment of malaria. 

Tachibana K, Scheuer PJ, Tsukitani Y, Kikuchi H, Vanengen D, Clardy J, Gopichand Y, Schmitz EJ (1981) Okadaic Acid, a Cytotoxic Polyether from Two Marine Sponges of the Genus Halichondria. J Am Chem Soc 103 2469... 

It was in an association between a bacterium of the genus Pseudomonas (KK10206C strain), and the hahchon-drid sponge Halichondria okadai that a C50 carotenoid, okadaxanthin, was isolated (Mild et al, 1994). 

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... 

Topsentolide Ai is the first of a series of oxylipins isolated from an imdetermined spedes of genus Topsentia of Korean origin. This derivative has structural similarities with halicholactone, first isolated from the Japanese spedes Halichondria okadai and subsequently found in the brown alga Laminaria sinclairii, but does not include cydopropane (see Chapter 14). The presence of an epoxy may explain the anti-tumor properties of topsentolide Ai (Luo et al., 2006b). The absolute configuration of topsentolide Al was determined by synthesis (Kobayashi, Ishigami, and Watanabe, 2010). 

Among the new structures it is worth mentioning halidonin A, isolated from a Korean Halidona sp. with a new carbon skeleton neopetrosiamine A from the Caribbean Neopetrosia proxima with a new tetracydic bis-piperidine skeleton and three new alkaloids related to halidonacydamine, but isolated from an Indonesian Halichondrid sponge of the genus Halichondria. 

G., Munro, M.H.G., Bernhardt, P.V., and Garson, M.J. (2010) Structure and absolute configuration of 3-alkylpiperidine alkaloids from an Indonesian sponge of the genus Halichondria. Tetrahedron, 66,2752-2760. 

Kernan, M.R., Molinski, T.F., and Faulkner. D.J. (1988) Macrocydic antifungal metabolites from the Spanish dancer nudibrandi Hexabranchus sanguineus and sponges of the genus Halichondria. ]. Org. Chem., 53, 5014-5020. 

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