10233. Pseudopterosins
Description and references
Family of anti-inflammatory diterpene glycosides originally isolated from the marine gorgonian coral, Pseudopterogorgia elisabethae. Isoln of A-D: S. A. Look et al., Proc. Natl. Acad. Sci. USA 83, 6238 (1986) DOI PubMed; idem et al., J. Org. Chem. 51, 5140 (1986) DOI; of E-L: V. Roussis et al., ibid. 55, 4916 (1990) DOI. Total synthesis of A: C. A. Broka et al., ibid. 53, 1584 (1988) DOI; of A and E: E. J. Corey, P. Carpino, J. Am. Chem. Soc. 111, 5472 (1989) DOI. Pharmacological characterization of A and E: A. M. S. Mayer et al., Life Sci. 62, 401 (1998) DOI. Biosynthesis: R. G. Kerr et al., J. Ind. Microbiol. Biotechnol. 33, 532 (2006) DOI PubMed. Review: T. J. Heckrodt, J. Mulzer, Top. Curr. Chem. 244, 1-41 (2005) DOI.
Derivative
Pseudopterosin A.Nomenclature
CAS number: 104855-20-1
(3S,7R,9S,9aR)-2,3,7,8,9,9a-Hexahydro-5-hydroxy-3,6,9-trimethyl-7-(2-methyl-1-propenyl)-1H-phenalen-4-yl-β-d-xylopyranoside. C25H36O6; mol wt 432.55.
C 69.42%, H 8.39%, O 22.19%.
Properties
Amorphous solid. [α]D20 85° (c = 0.69 in chloroform). uv max (methanol): 230, 278, 283 nm (ε 11200, 2060, 2200).Derivative
Pseudopterosin B.Nomenclature
CAS number: 104855-21-2
(3S,7R,9S,9aR)-2,3,7,8,9,9a-Hexahydro-5-hydroxy-3,6,9-trimethyl-7-(2-methyl-1-propenyl)-1H-phenalen-4-yl-β-d-xylopyranoside 2-acetate. C27H38O7; mol wt 474.59.
C 68.33%, H 8.07%, O 23.60%.
Properties
Oil. [α]D20 55.2° (c = 2.1 in chloroform). uv max (methanol): 230-235, 274, 285 nm (ε 6000, 1400, 1600).Derivative
Pseudopterosin C.Nomenclature
CAS number: 104881-78-9
(3S,7R,9S,9aR)-2,3,7,8,9,9a-Hexahydro-5-hydroxy-3,6,9-trimethyl-7-(2-methyl-1-propen-1-yl)-1H-phenalen-4-yl-β-d-xylopyranoside 3-acetate. C27H38O7; mol wt 474.59.
C 68.33%, H 8.07%, O 23.60%.
Properties
Crystals from ethanol + ethyl acetate, mp 113.5-115°. [α]D20 77° (c = 1.09 in chloroform). uv max (methanol): 229, 275, 282 nm (ε 9600, 1500, 1700).Derivative
Pseudopterosin E.Nomenclature
CAS number: 121011-80-1
(1S,3R,7S,9aR)-2,3,7,8,9,9a-Hexahydro-6-hydroxy-1,4,7-trimethyl-3-(2-methyl-1-propenyl)-1H-phenalen-5-yl 6-deoxy-α-l-galactopyranoside. C26H38O6; mol wt 446.58.
C 69.93%, H 8.58%, O 21.50%.