33R- 34R= 36R CO.Nle CO:Me OH 37 20:3)and the a-hydroxy fatty acid chain (C19-C24).Four of 第骨 the major met cora corresponded to the ophidiacerebrosides A-Disolated from the Three novel halogenated azulenes (28-30),along with N.N- SperOharcropAimfomteBa an-guiazulenylmethane (31).were isolated from HO、R OH the yellow pigment (32),was isolated as a minor metabolite of the gorgonian Placogorgia sp.retrieved from the same a8 入R OH 38R.Raalphetic chain A furthe specin of D contain the novel (20R)-2E-cholesta4-diene-3.6-dione (39) together with three known 3-keto steroids. 39 30 R:=H.Ra Br Deep-water corals belonging to the genus Lophelia (Fig.1)and Ma ca Io he Indian described from a deep-water scleractinian coral were the nov cholic-acid-type 3-keto steroids 33-37 isolated from the Pacific ith the nove along with othe steroids 33-37,three ther known steroidal natural products rcobatndh be noted that all comp ounds apart from 80m depth.gave0 and 42 The same group found that the Mediterranean scleractinian coral Dendrophyllia cornigera contained a complex mixture of Deltocyathus magnificus(depth 463 m).Stephanocyatus spiniger 1136|Nat.Prod.Rep,.2008,25,1131-1166 This journal isThe Royal Society of Chemistry 2008 Three novel halogenated azulenes (28–30), along with N,N￾dimethylamino-3-guaiazulenylmethane (31), were isolated from a blue gorgonian (Paramuriceidae family), collected from Oahu, Hawaii, at 350 m depth using a submersible,111,112 while the yellow pigment (32), was isolated as a minor metabolite of the gorgonian Placogorgia sp., retrieved from the same location.113 Order Scleractinia. The scleractinian stony corals are reef￾building corals with around 800 species described world-wide, predominantly from shallow waters.3 Scleractinians have a wide distribution and have been recorded from Antarctica to Norway, and down to depths of 6200 m.114 The first secondary metabolites described from a deep-water scleractinian coral were the novel cholic-acid-type 3-keto steroids 33–37 isolated from the Pacific coral species Deltocyathus magnificus collected by trawling near the Loyalty Islands at a depth of 463 m.114 Along with the novel steroids 33–37, three other known steroidal natural products were obtained. It should be noted that all compounds apart from 33 were obtained after diazomethane treatment. The same group found that the Mediterranean scleractinian coral Dendrophyllia cornigera contained a complex mixture of b-glucosylceramides (b-GlcCer) (38) with a high degree of heterogeneity in both the sphingoid moiety (D18:2, 19:2, 20:2, 20:3) and the a-hydroxy fatty acid chain (C19–C24).115 Four of the major b-GlcCer metabolites of the dendrophylliid coral, collected by dredging at 162 m in northern Corsica, Ligurian Sea, corresponded to the ophidiacerebrosides A–D isolated from the shallow-water sea star Ophidiaster ophidiamus from the Balearic Islands, Spain.116 A further specimen of D. cornigera, collected at a depth of 80 m near the island of Serifos, Mediterranean Sea, was found to contain the novel (20R)-22E-cholesta-4,22-diene-3,6-dione (39), together with three known 3-keto steroids.117 Deep-water corals belonging to the genus Lophelia (Fig. 1) and Madrepora are found at depths of 50 to 2000 m, ranging from the Atlantic to the Indian Ocean, and have been well studied, in terms of their range, distribution and phylogeny.118,119 A spec￾imen of Madrepora oculata recovered near St. Paul Island (S Indian Ocean) by trawling at a depth of 290 m, has yielded the novel 10-hydroxydocosapolyenoic acids 40–42, along with other known 10-hydroxydocosa- and 8-hydroxyeicosa-polyenoic acids,120 while the same coral species collected in Trondheimsf￾jord, Norway, by dredging at 350–380 m depth, gave 40 and 42. Of the other deep-water scleractinians surveyed in the same study, including Letepsammia formosissima (depth 430 m), Deltocyathus magnificus (depth 463 m), Stephanocyatus spiniger 1136 | Nat. Prod. Rep., 2008, 25, 1131–1166 This journal is ª The Royal Society of Chemistry 2008