Coral Pseudopterogorgia

Abstract Recent chemical studies on the marine soft corals and terrestrial plants have lesnlted in the isolation of several novel componnds. The soft corals, Pseudopterogorgia elisabethae and Cladiella species yielded several novel terpenoids, exhibiting antimicrobial activities. New steroids were isolated from terrestrial fungi, Mucor plumbeus and Coprims micaceus. Phytochemical studies on the Buxus hyrcana, collected from Iran, have yielded steroidal bases. This revdew describes the new natiual products exhibiting different bioactivities from the aforementioned sources. 

Caribbean coral Pseudopterogorgia elisabethae discovered by Fenical et al. [47], Pseudopterosin E, Fig. (3) is the one with the best pharmacological profile, combining low toxicity and potent antiinflammatory activity. In human neutrophils, pseudopterosin E inhibits degranulation and formation of Ieukotrienes [2], In 1991, phase I clinical trials were initiated with pseudopterosin E as a topical anti-inflammatory agent. Recently, novel anti-inflammatory natural products have been isolated from this Caribbean soft coral [48,49], Japanese researchers reported the isolation of a group of compounds designated helioporins A-E, which are related to the pseudopterosins [1],... 

Rodriguez, A. D. and Boulanger, A., New guaiane metabolites from the Caribbean gorgonian coral, Pseudopterogorgia americana, J. Nat. Prod., 60, 207, 1997. 

Mayer, A. M. S., Jacobson, P. B., Fenical, W., Jacobs, R. S., and Glaser, K. S., Pharmacological characterization of the pseudopterosins novel anti-inflammatory natural products isolated from the Caribbean soft coral, Pseudopterogorgia elisabethae, Pharmacol. Lett., 62, 401, 1998. 

Norzooanemonin (161) was isolated in 1973 by Weinheimer et al. (227), from the Caribbean bark coral Pseudopterogorgia americana. These authors confirmed structure 161 by synthesis. Methylation of imidazole-4-carboxy-lic acid with dimethyl sulfate yielded 85% norzooanemonin, identical to the natural product. 

Recently, Pseudopterosin C, a diterpene riboside isolated from the gorgonian corals Pseudopterogorgia bipinata and P. elisabethae [134] was launched by Estde Lauder as an additive to anti-aging cosmetics. It exhibits potent antiinflammatory and analgesic activities by reversibly affecting both, lipoxygenase and phospholipase A2 [135]. 

Sulfated glycoprotein containing d-G1c, D-Gal, L-Gal, o-Ara, l-Fuc and D-Glucuronic acid residues. Struct, has been partially determined. Isol. from the Caribbean soft coral Pseudopterogorgia americana. Sol. H2O poorly sol. MeOH, hexane. 

Montalvo, D., Amade, P., Eiumel-Le Bon, C., Eernandez, R and Reyes, E. (2006) Acerolide, a new cytotoxic cembranolide from the soft coral Pseudopterogorgia acerosa. Nat. Prod. Res., 20, 548-552. 

Ospina, C.A., Rodriguez, A.D., Sanchez, J.A., Ortega-Barria, E., Capson, T.L., and Mayer, A.M.S. (2005) Caucanolides A-F, unusual antiplasmodial constituents from a Colombian collection of the gorgonian coral Pseudopterogorgia bipinnata. J. Nat. Prod., 68, 1519-1526. 

McEmoe, F.J. and Fenical, W. (1978) Structures and synthesis of some new antibacterial sesquiterpenoids from the gorgonian coral Pseudopterogorgia rigida. Tetrahedron, 34,1661-1664. 

A recent example demonstrates that corals rely on induced biosynthesis of terpenes as a dynamic defense strategy as well. The induction of terpenoid secondary metabolites was observed in the sea whip Pseudopterogorgia elisabethae [162]. Levels of pseudopterosins 89-92, a group of diterpene glycosides with anti-inflammatory and analgesic properties (Scheme 23) [163-165], are increased in response predation by the mollusk Cyphoma gibbosum. First bioassays indicate that these natural products are involved in the chemical defense. 

Buxus hyrcana, Cladiella, Coprinus micaceus, coral, marine, Mucor plumbeus, Pseudopterogorgia elisabethae, steroids, terpenoids, terrestrial... 

Pseudopterosin A (129), which is a diterpene glycoside isolated from the sea whip Pseudopterogorgia elisabethae, shows anti-inflammatory activity by inhibiting release of leukotriene B2 from leukocytes (2, 35). A more interesting class of diter-penes includes sarcodictyn A (130) and elentherobin (131), which were isolated from the soft corals Sarcodictyon roseum and Eleutherobia sp., respectively. These diterpenoids show potent cytotoxicity by stabilizing microtnbnles (2, 35). 

As we have discussed above, a significant fraction of Pseudopterogorgia metabolites have been evaluated in human disease-oriented in vitro testing programs. For instance, several major anti-inflammatory leads have emerged from work on Pseudopterogorgia corals. Most prominent are pseudopterostn A (1), pseudopterosin E... 

The known sterol derivative 61, containing a cyclopropane side chain was isolated in our lab (Adamczeski [8]) from Pseudopterogorgia sp. collection from Indonesia. This compound was first isolated from the soft coral... 

Sea whips encompass widely diverse morphologies among soft-bodied marine invertebrates and are readily abundant in reef environments. As documented by Pawlik [4], and Fenical and coworkers [59], this genus of soft corals has fleshy tissues that appear to be physically unprotected from potential predators, yet seem to be unmolested and have only a few predators. Analysis of the wide spectrum of the potent biologically active metabolites of Pseudopterogorgia presented in table 7 may offer a possible explanation of the seemingly few predators of this specie. 

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