Cytotoxic sesterterpenes

Rudi, A. Yosief, T. Schl er, M. Kashman, Y. (1999A) Bilosespenes A and B two novel cytotoxic sesterterpenes from the marine sponge Dysidea cinerea. Org. Lett., 1,471-2. 

Several other marine sponges have been investigated in the last decade, in the search for novel bioactive sesterterpene molecules. A sample of the sponge Dysidea herbacea from the Red Sea is unique in that it contains cytotoxic sesterterpenes with a scalarin skeleton, e.g., scalardysin, Fig. (16) and the C2i-fiiranoterpene fiirospongolide, Fig. (17). 

From the Maldives Black marine sponge Hyrtios erectci, several cytotoxic sesterterpenes were isolated, such as the penytacyclic sesterterpenes designated sesterstatins [125-127] and puupehenone, Fig. (18) with a quinone-methide system [128], Three novel cytotoxic nor-sesterterpenes, rhopaloic acid A, Fig. (19), B and C, were recently isolated from the sponge Rhopciloeides sp. 

In the same year Tsuda et al. (27) reported the isolation of cytotoxic sesterterpenes from the Okinawan marine sponge Luffariella sp. among which was a compound with a 5,6-dihydro-a-pyrone moiety, luffariolide E. This compound showed cytotoxicity against murine leukaemia LI210 cells (IC50 1.1-7.8 pg/ml) in vitro. The original structure, which rested on chemical and spectroscopic evidence, has been corrected by synthesis to (24) (28). 

Wei, H., Itoh, T., Kinoshita, M., Nakai, Y, Kurotaki, M., and Kobayashi, M. (2004) Cytotoxic sesterterpenes, 6-epi-ophiobolin G and 6-epi-ophiobolin N, from marine derived fungus Emericdla variecolor GFIO. Tetrahedron, 60, 6015-6019. 

Aurorals 1-4 are cytotoxic sesterterpenes derived from iso-malabaricane and similar to jaspiferals. They were all isolated from Rhabdastrella bosteUata, harvested in New Caledonia (Bourguet-Kondradd et al., 2000). Most of the stellettins A-M were isolated from species of the genus Stdletta, especially Stdletta tenuis (Su et al., 1994 lin et al., 2007), but some were also isolated also from Rhabdastrella bostdlata. 

Alea, G.V, Carroll, A.R., and Bowdert, B.F. (1994) Cosdrtoquinol, a new cytotoxic sesterterpene from a Dictyoceratid sponge, Coscinoderma sp. Aust. J. Chem., 47,191-194. 

He, H., Kulanthaivel, P., and Baker, B.J. (1994) New cytotoxic sesterterpenes from the marine sponge Spongia sp. Tetrahedron Lett., 35, 7189-7192. 

New cytotoxic sesterterpenes from the New Caledonian marine sponge Petrosaspongia nigra (Bergquist). Tetrahedron, 53, 10451-10458. 

Ueoka, R., Nakao, Y, Fujii, S., Van Soest, R.W.M., and Matsunaga. S. (2008b) Aplysinophdes A-C, cytotoxic sesterterpenes from the marine sponge Aplysinopsis digitata. J. Nat. Prod., 71, 1089-1091. 

These types of compounds also showed other interesting properties, such as antineoplasic and cytotoxic activity reported from scalarane-type sesterterpenes of the Indian Ocean sponge Hyrtios erecta [109,110], and antituberculosis properties [111]. 

This compound also showed antispasmodic activity [122], A variety of cytotoxic compounds was isolated, including a bishomosesterterpene and dysidiolide from another Dysideci sp., a sulfated sesterterpene hydroquinone from a Hippospongia sp., and two new sesterterpenes, lintenolides F and G from the Caribbean sponge Cacospongia linteiformis [123,124],... 

A new sesterterpene epoxide-diol, aspergilloxide 25, was isolated from the extract of a cultured marine-derived fungus (strain CNM-713), a member of the genus Aspergillus 25 showed little in vitro cytotoxicity toward HCT-116 human colon carcinoma. 

Two new sesterterpenes, 6-epi-ophiobolin G 49 and 6-epi-ophiobolin N 50, were isolated from the extraets of the fungus, Emericella variecolor GFIO obtained from marine sediment/ These eompounds showed cytotoxicity against the neuroblastoma cell line, Neuro 2A. 

From the Japanese nudibranch Chromodoris inornata were isolated two sesterterpenes, inorolides A (236) and B (237) with a new carbon skeleton. Both compounds exhibited cytotoxic activity against L1210 (IC50 1.9 and 0.72 pg/ml for 236 and 237, respectively) and KB (IC50 3.4 and 2.2 pg/ml for 236 and 237, respectively) cell lines [163],... 

Sesterterpenes Variabilin (271) Sponge, Ircinta sp. Sarcotragus sp. HSV Cytotoxicity [202]... 

The novel sesterterpene salmahyrtisol A and three other new sca-larane-type sesterterpenes (salmahyrtisol, 3-acetyl sesterstatin 1, and 19-acetyl sesterstatin 3), isolated from the Red Sea sponge Hyrtios erecta, have significant cytotoxicity against human lung carcinoma, human colon carcinoma, and murine lukemia. Halorosellinic acid, an... 

Irciformonines A-K are an original series of trinor-sesterterpenes at C22, aU isolated from the species Ircinia formosana harvested in Taiwan. These derivatives do not contain tetronic add and are only moderately cytotoxic (Shen et al, 2006, 2009). 

There are some atypical sesterterpenes, such as the luffariellins, lintenone and the cacospongionolides, that have anti-inflammatory, antibiotic or cytotoxic properties. 

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