New pseudopterosin and seco-pseudopterosin diterpene glycosides from two Colombian isolates of Pseudopterogorgia elisabethae and their diverse biological activities.
As part of an ongoing program to explore the chemical constituents of Caribbean marine invertebrates, a family of 13 new diterpene glycosides, pseudopterosins P-Z (1-11) and seco-pseudopterosins H (12) and I (13), have been isolated from the organic extracts of two collections of the sea whip Pseudopterogorgia elisabethae procured near the Colombian Southwestern Caribbean Sea. The structures of compounds 1-13, including absolute stereochemistry, have been proposed on the basis of comprehensive spectral analyses, chemical transformations, specific rotation, and TLC chromatographic analyses. Pseudopterosin Q (2) inhibited thromboxane B2 (TXB2) (IC50 = 4.7 microM) and superoxide anion (O2-) (IC50 = 11.2 microM) generation from E. coli lipopolysaccharide (LPS) activated rat neonatal microglia in vitro. In contrast, pseudopterosins P (1), U (6), V (7), W (8), and X (9) as well as seco-pseudopterosins H (12) and I (13) demonstrated minimal effects on both TXB2 and O2- release. In addition, some of the new compounds displayed strong antituberculosis, antiviral, antimalarial, and anticancer activity.
Rodríguez
Ileana I
II
Department of Chemistry, University of Puerto Rico, PO Box 23346, UPR Station, San Juan, 00931-3346.
Shi
Yan-Ping
YP
García
Oscar J
OJ
Rodríguez
Abimael D
AD
Mayer
Alejandro M S
AM
Sánchez
Juan A
JA
Ortega-Barria
Eduardo
E
González
José
J
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000995:Antitubercular Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D003063:Cnidaria / Q000737:chemistry*; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009792:Oceans and Seas; D051381:Rats
D000894:Anti-Inflammatory Agents, Non-Steroidal; D000962:Antimalarials; D000970:Antineoplastic Agents; D000995:Antitubercular Agents; D000998:Antiviral Agents; D004224:Diterpenes; D006027:Glycosides; C049922:pseudopterosins