Seco-pseudopterosins

Pseudopterosins coexist with the seco-pseudopterosins, suggesting that these two classes of diterpenes are produced from a single cyclase product. Elisabethatriene (42) undergoes aromatization to erogorgiaene (1) presumably a series... 

Scheme 4 Plausible biosynthetic pathway of the seco-pseudopterosins and pseudopterosins...

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... 

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. 

H) seco-Pseudopterosins (compounds reported—13) In June 1980, as part of a NSF(National... 

Fenical and coworkers [19] collected another unidentified, distinctly different taxonomic specie of this genus containing the novel diterpenoids, 8-11, which were also related to the pseudopterosins. The diterpenoids included a unique hydroperoxide, 10, and the quinone, 11, which contain the aglycon moiety found in the seco-pseudopterosins, 7 seco A-D. 

A group of challenging target molecules with important biological activities are the pseudopterosins [23] and the seco-pseudopterosins [24], marine diterpene glycosides with strong anti-inflammatory properties (Fig. 3). 

Scheme 7 Total synthesis of the pseudopterosin aglycone 31 and the seco-pseudopterosin aglycone 42 according to Schmalz...

The helioporins, a group of marine diterpenes with antiviral and cytotoxic properties, are structurally closely related to the (seco-) pseudopterosins and all possess a characteristic benzodioxole unit [29]. Their stereostructure was assigned as shown in Fig. 4 with a cfs-relationship of the two benzylic sidechains at the tetralin nucleus. 

Look, S.A. and Fenical, W. (1987) Seco-pseudopterosins, antiinflammatory diterpene-glycosides from gorgonians octocoral genus Pseudopterogorgia. Tetrahedron, 43, 3363-3370. 

Majdalani, A. and Schmalz, H.G. (1997) Enantioselective synthesis of the aglycones of pseudopterosin and seco-pseudopterosin via a common synthetic intermediate. Synlett, 1303-1305. 

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