Alcyonium

Isopr. DITERP. 3.7-cvclized cembrane coralloidolide C (Alcyonium [= Parerythmpodium] coralloides Pallas, 1766, Alcyonacea, Cnid. from East Pyrenean waters D Ambrosio 1990) TRITERP. soualene derived testudinariol Pleurobranchus testudinarius, Notaspidea, Moll, from the Thyrrenian Sea Spinella 1997) raspacionins Raspaciona aculeata, Axinel., Porif. from eastern Pyrenean waters Cimino 1993) STEROIDS AB-nor incisterol Dictyonella incisa, Halichon., Porif from the Ligurian Sea Ciminiello 1990). 

Soft coral, Alcyonia alcyonium, whole Plumose anemone, Metridium senile, whole Various species, whole Uncontaminated areas Noncontaminated areas Contaminated areas... 

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). 

Palermo JA, Brasco MFR, Spagnuolo C, Seldes AM (2000) Illudalane Sesquiterpenoids from the Soft Coral Alcyonium paessleri The First Natural Nitrate Esters. J Org Chem 65 4482... 

The typical secondary metabolites of soft corals are diterpenoids, although some species also produce sesquiterpenoids. The sesquiterpene portion of furoquinol (Structure 2.102) is labeled by [2-3H]mevalonolactone in Sinularia capillosa,m while Heteroxenia sp. converts acetate and meva-lonate into cubebol (Structure 2.103) and clavukerin A (Structure 2.104).188 In contrast, acetate is used for cetyl palmitate synthesis in Alcyonium molle, but not for de novo diterpene biosynthesis.188... 

Dai, M. C., Garson, M. J., and Coll, J. C., Biosynthetic processes in soft corals. I. A comparison of terpene biosynthesis in Alcyonium molle (Alcyoniidae) and Heteroxenia sp. (Xeniidae), Comp. Bio-chem. Physiol., 99B, 775, 1991. 

Alcyonium carneumy L. Agassiz. Southwest of Stellwagen Bank, off... 

The potential anti-inflammatory properties of southern African soft coral metabolites were further exemplified by the isolation of five diterpene esters valdivones A (101), B (102), their corresponding methoxy ketals (103, 104) and dihydrovaldivone A (105) from Alcyonium valdivae (Family Alcyoniidae) collected off Coffee Bay on the warm temperate east coast of southern Africa (Figure 1) [94]. The structures of these compounds were determined from analysis of their 2D-NMR data with coupling constant analysis and nOe data providing the relative stereochemistry of 101 and 102. Valdivones A and B showed fairly strong inhibition of chemically-induced inflammation in the mouse ear assay (93% and 72% inhibition at 50 pg/ear respectively) but did not significantly inhibit bee venom phospholipase A2 (ca. 43% at 16 pgmL1) [94]. 

An unusual intraspecific variation in the structures of the diterpene metabolites produced by the soft coral Eleutherobia aurea (formerly Alcyonium aurea) has been observed from several collections of this species made from the Aliwal Shoal and Sodwana Bay regions [95]. The Sodwana Bay specimens yielded antheliatin (106), zahavins A and B (107,108) [96], sarcodictyin A (109) and eleuthosides A and B (110, 111) [95], In addition to 107, other xenicane diterpenes including 9-deacetoxy-14,15-deepoxyxeniculin (112), 7,8-epoxyzahavin A (113) and xeniolide C (114) were isolated from the Aliwal Shoal specimens of E. aurea [97]. Sarcodictyon A and 9-deacetoxy-14,15-deepoxyxeniculin were isolated previously from the stoloniferous octocoral Sarcodictyon roseum [98] and the soft coral Xenia obscuronata [99]. 

A similar assay was used to examine the effects of extracts from three soft corals Alcyonium paessleri, Clavularia frankliniana, and Gersemia antarctica, against three species of marine bacteria (Slattery et al. 1995). In this assay, replicate 20-g soft coral samples were extracted in 200 ml of solvent and then diluted to tissue level concentrations. Twenty-five microliters of each soft coral extract or a solvent control were then spotted onto glass microscope slide cover-slips. The coverslips were placed into individual wells of tissue culture plates that contained 2 ml of sterile-filtered seawater seeded with 50 Lil of a bacterial suspension (7.5 x 10 cells/ml). Following a 48-h incubation, the coverslips were washed with sterile-filtered seawater to remove unattached cells and stained with DAPI (4,6-diamidino-2-phenylindole). The number of cells in each of five replicate microscope fields per coverslip were counted using epifluorescence microscopy. Bacterial attachment was found in this study to be inhibited by the chloroform extracts of both A. paessleri and G. antarctica and the methanol extract of G. antarctica. The active chloroform extracts did not display antimicro-... 

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