Pseudopterogorgia elisabethae Pseudopterosin

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. 

Scheme 23 Inducible pseudopterosins in the sea whip Pseudopterogorgia elisabethae...

A C9-C14 cycHzation forms the ring C and leads to the amphilectane skeleton which is foimd for instance in pseudopterosins A-F (10, aglycone) [10] isolated from Pseudopterogorgia elisabethae extracts stemming from a Bahamian collection site (Fig. 5). This class of natural products can be characterized as... 

The pseudopterosins and seco-pseudopterosin isolated from Bahamian specimens of Pseudopterogorgia elisabethae display strong anti-inflammatory and analgesic activity. These diterpene glycosides had potencies superior to those of... 

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],... 

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. 

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). 

Sanchez JA, Ortega-Barria E, Gonzalez J. New pseudopterosin 134. and seco-pseudopterosin diterpene glycosides from two Colombian isolates of Pseudopterogorgia elisabethae and their diverse biological activities. J. Nat. Prod. 2004 67 1672-1680. 

A few reports on anti-CMV compounds of marine origin belonging to other structural types have also been found in the literature. Examples included two plastoquinones isolated from the brown alga Sargassum micracanthum which was found to have potent antiviral activity against human CMV [114], and pseudopterosin P, Fig. (9) from the sea whip Pseudopterogorgia elisabethae [98]. 

A comprehensive study of Pseudopterogorgia elisabethae from different regions of the Caribbean Sea and tropical Atlantic areas unveiled a novel class of compounds, known collectively as the pseudopterosins. Pseudopterosins are metabolites which contain diterpene glycoside moieties. Polyhydroxy steroids are another class of compounds commonly isolated from solvent extracts of this specie. 

Pseudopterosins. Diterpene glycosides (P A-L) from the sea whip Pseudopterogorgia elisabethae living in the tropical Atlantic. P occur as aglycones not only in the form shown but also as the 7)8-epimers and the enantiomers. The sugar residue at 0-8 or 0-9 can be D-xylo-, L-fuco-, and D-arabinopyranosyl which may be acetylated in the 2-, 3-, or 4-position. 

Look SA, Fenical W, Jacobs RS, Clardy J (1986) The pseudopterosins anti-inflammatory and analgesic natural products from the sea whip Pseudopterogorgia elisabethae. Proc Natl Acad Sci USA 83 6238-6240... 

Roussis V, Fenical W, Strobel SA, Van Duyne GD, Clardy J (1990) New anti-inflammatory pseudopterosins liom the marine octocoral Pseudopterogorgia elisabethae. J Org Chem 55 4916 922... 

Duque, C., Puyana, M., Narvaez, G., Osorno, O., Kara, N., and Fujimoto, Y. (2004) Pseudopterosins P-V, new compounds from the gorgonian octocoral Pseudopterogorgia elisabethae from Providencia islands, Colombian Caribbean. Tetrahedron, 60,10627-10635. 

Mydlarz, L.D., Jacobs, R.S., Boehnlein, J., and Kerr, R.G. (2003) Pseudopterosin biosynthesis in Symbiodinium sp., the dinoflagellate symbiont of Pseudopterogorgia elisabethae. Chem. Biol., 10, 1051-1056. 

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