Hyrtios sponge

Rogers, S. D. and Paul, V. J., Chemical defenses of three Glossodoris nudibranchs and their dietary Hyrtios sponges, Mar. Ecol. Prog. Ser., 77, 221, 1991. 

Pina, I.C., Sanders, M.L., and Crews, P. (2003) Puupehenone congeners from an Indo-Pacific Hyrtios sponge. J. Nat. Prod., 66, 2-6. 

Kirsch G Koeng GM, Wright AD, Kamisnky RA. (2000) New bioactive sesterterpene and antiplasmodial alkaloids from marine sponge Hyrtios. JNat Prod 63 825-829. 

Kobayashi, M. Aoki, S. Gato, K. Matsunami, K. Kurosu, M. Kitagawa, I. (1994) Trisindoline, a new antibiotic indole trimer, produced by a bacterium of Vibrio sp. separated from the marine sponge Hyrtios altum. Chem. Pharm. Bull., 42, 2449-51. 

Utkina, N. K. (2009). Antioxidant activity of aromatic alkaloids from marine sponges Aaptos aaptos and Hyrtios sp. Chem. Nat. Compd. 6, 849-853. 

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]. 

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. 

Manzamine-type alkaloids were also reported in another samples of marine sponges, eg., the Okinawan Amphimedon sp. [252-254], Pachypellina sp. [255], and a novel alkaloid called hyrtiomanzamine from Hyrtios erecta, with interesting immunosuppressive activity [256]. From... 

The New Zealand bryozoan Cribicellina cribraria was the source of several P-carboline alkaloids. One of these examples, compound 34, has a unique methylsulfone substituent. Spectroscopic studies identified 34 as 1-ethyl-4-methylsulfone-P-carboline [34]. Hyrtiomanzamine (35) represents the first example of a 6-OH-P-carboline ring associated with a betaine unit to be obtained from a natural source. This compound was isolated from the Red Sea sponge Hyrtios erecta and its structure was determined on the basis of its spectral data [35]. Compound 35 displayed immunosuppressive activity with an ED50 of 2 mg/ml in the B lymphocytes reaction assay. The lack of cytotoxicity against KB cells indicated that the immunosuppressive activity of 35 is specific and not due to a general cytotoxic effect. 

The Hawaiian sponge Hyrtios sp. from Oahu has furnished 21-chloropuupehe-nol (430), while the same sponge from Maui contains molokinenone (431) (619). The absolute configuration of these drimane-phenolic metabolites has been assigned as shown based on that of puupehenone (620). The South Georgia Island soft coral Alcyonium paessleri produces several novel illudalane sesquiterpenoids, including the chlorinated alcyopterosins A (432), D (433), K (434), and L (435) (621). 

Nasu SS, Yeung BKS, Hamann MT, Scheuer PJ, Kelly-Borges M, Goins K (1995) Puupehenone-Related Metabolites from Two Hawaiian Sponges, Hyrtios spp. J Org Chem 60 7290... 

Aoki S, Ye Y, Higuchi K, Takashima A, Tanaka Y, Kitagawa I, Kobayashi M (2001) Novel Neuronal Nitric Oxide Synthase (nNOS) Selective Inhibitor, Aplysinopsin-Type Indole Alkaloid, from Marine Sponge Hyrtios erecta. Chem Pharm Bull 49 1372... 

Sata N, Galario MA, Sitachitta N, Scheuer PJ, Kelly M (2005) Poipuol, a New Metabolite from a Hawaiian Sponge of Genus Hyrtios. J Nat Prod 68 262... 

Idiadione (56) was synthesized from citronellal, establishing the stere-ogenic center as S [31], Cytotoxic sesterterpenoid cacospongionolide D (57) was isolated from Fasciospongia cavernosa from the Bay of Naples [32]. Thorectolide monoacetate (58), obtained from a New Caledonian marine sponge identified as a Hyrtios species [33], in contrast possessed antiinflammatory properties. The bicyclic lactone astakolactin (59) was obtained... 

Hainan Is., China) contained 12o -0-acetylhyrtiolide (197) [103]. A new scalarane-type pentacyclic sesterterpene, sesterstatin 6 (198), was isolated from the Republic of Maldives marine sponge Hyrtios erecta. The structure was elucidated by analyses with HRMS and high-field 2-D NMR spec-... 

Another large group of brominated tryptophan-derived marine alkaloids are the aplysinopsins and several new examples have been reported. The sponge Hyrtios erecta has furnished 20 and 21[26], while a New Zealand asddian is the source of kottamides A-E, for example A (22) [27] and E (23) [28], The stony coral Tubastraea sp. contains the structurally complex and unprecedented bisindole tubastrindole A (24) [29]. 

The Okinawan ascidian Lissodinum sp. produces the cytotoxic diterpene alkaloids haterumaimides J (99) and K (100) [86[. The incredibly prolific cyanobacterium Lyngbya majuscula has furnished the quinoline alkaloid 101 [87[. The new quinolones 102 and 103 were isolated from the sponge Hyrtios erecta [26[. 

Kobayashi, M., Aoki, S., Sakai, H., Kawazoe, K., Kihara, N., Sasaki, T., and Kitagawa, I. (1993). Altohyrtin A, a potent anti-tumor macrolide from the Okinawan marine sponge Hyrtios altum. Tetrahedron Lett. 34, 2795-2798. 

From the Fijian sponge Fascaplysinopis reticulata were isolated two sesterterpenoids related to luffariellolide, wodehydro-luffariellolide (69) and dehydro-luffariellolide diacid (70). Ao-dehydro-luffariellolide inhibited at 1 mg/ml 81% of the HIV-1 reverse transcriptase activity [90] and reduced the activity of p56lck tyrosine kinase at 0.5 mM to 45% in ELISA based assays [91]. Hyrtiolide (71) was isolated from the Fijian sponge Hyrtios erecta together with its correlated wo-dehydro-... 

From the Okinawan sponge Hyrtios erectus was isolated hyrtiosal (154), possessing a novel rearranged tricarbocyclic skeleton (hyrtiosane) [164], Its structure was confirmed by total synthesis [165], This compound exhibited in vitro antiproliferative activity against KB cells with an IC50 of 3.0 pg/ml [164],... 

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