New antiproliferative 9,11-secosterol from soft coral gersemia fruticosa

9,11-Secosteroids with cytotoxic activity from the South China Sea gorgonian coral Subergorgia suberosa

“…Since the first isolation of 9,11-secosterol from the gorgonian Pseudopterogorgia americana in 1972 [1], the members of this type of interesting sterol have increased very quickly and over scores of them have been discovered up to now, from a great variety of marine organisms involving acidians [2], sponges [3], gorgonians [4][5][6][7][8], and particularly soft corals [9][10][11][12][13][14][15][16][17]. Characterized by bond cleavage between C-9 and C-11, 9,11-secosterols have attracted much attention from chemists and pharmacologists due to their versatile biological effects such as antiviral, antimicrobial, cytotoxic, antiinflammatory activities [2,4,[7][8][9][10][14][15][16][17].…”

“…Characterized by bond cleavage between C-9 and C-11, 9,11-secosterols have attracted much attention from chemists and pharmacologists due to their versatile biological effects such as antiviral, antimicrobial, cytotoxic, antiinflammatory activities [2,4,[7][8][9][10][14][15][16][17].…”

A new 9,11-secosterol with a 1,4-quinone from a Korean marine sponge Ircinia sp.

“…Likewise, 13,14-secosteroids have been isolated from terrestrial plants (Bhandari et al 2006;Kirson et al 1976;Qiu et al 2008) and some of which have been demonstrated to possess anti-inflammatory activities (Qiu et al 2008). 9,11-Secosterols, the third group of secosteroids, are very rare in terrestrial organisms, and are instead of found primarily in marine invertebrates, mainly corals (Huang et al 2012;Cheng et al 2011;Chen et al 2011a, b;Ioannou et al 2009;Minh et al 2007;Epifanio et al 2007;Su et al 2006;Anta et al 2002;Aknin et al 1998;Morris et al 1998;He et al 1995;Lopp et al 1994;Koljak et al 1993;Ochi et al 1991;Fusetani et al 1989;Bonini et al 1983) and sponges (Van Altena et al 1999;De Rosa et al 1999;Rueda et al 1998;Lu and Faulkner 1997;Reddy et al 1997;Adinolfi et al 1994;Li et al 1994;Migliuolo et al 1992, Migliuolo et al 1991Capon and Faulkner 1985). In addition, 9,11-secosterols have been reported to display diverse bioactivities including cytotoxicity against cancer cell lines (Huang et al 2012;Cheng et al 2011;Chen et al 2011a, b;Su et al 2006;Morris et al 1998;Rueda et al 1998), anti-proliferative effects Inho Yang and Hyukjae Choi have contributed equally to this work.…”

“…against cancer cells (Ioannou et al 2009;He et al 1995;Lopp et al 1994;Koljak et al 1993), stimulation of bone formation (Minh et al 2007), fish feeding deterrence for coral and coral-associated algae (Epifanio et al 2007), protein kinase C inhibition (He et al 1995), anti-inflammatory activity (Huang et al 2012;He et al 1995), brine shrimp toxicity (Ochi et al 1991;De Rosa et al 1999), inhibition of starfish embryo cell division (Fusetani et al 1989), antifungal activity (Li et al 1994), and ichthyotoxicity (Capon and Faulkner 1985).…”

Asymmetric synthesis of the 2,2,3-trisubstituted cyclopentanone, D-ring fragment of 9,11-secosterols

“…1,13,14 Our strategy for the total synthesis of secosterol 1 and its analogues 1a and 1b was based on a separate synthesis of the AB-ring and D-ring, and on the coupling of these two fragments (Scheme 1). The synthesis of the AB-ring fragment precursor has been described by our group previously.…”