Saccopetrins A and B, Two Novel γ-Lactones from Saccopetalum prolificum

Abstract

Two new γ-lactones, saccopetrin A (1) and saccopetrin B (2), together with 10 known compounds have been isolated from the roots of Saccopetalum prolificum. Their structures were established by spectroscopic and chemical methods. The absolute configuration of 1 was determined by chemical transformation and the Mosher method. Cytotoxic activities were evaluated against several different cell lines. Compound 2 exhibited stronger cytotoxic activities than 1 against KB and HCT-8 cell lines at a concentration of 10^-5 mol/L.

Annonaceae - Saccopetalum prolificum - acetogenin-γ-lactones - saccopetrin A - saccopetrin B

References

• 1 Alali F Q, Liu X X, McLaughlin J L. Annonaceous acetogenins: recent progress. J. Nat.  Prod.. 1999;  62 504-40
• 2 Newman M S, Lee V. Improved procedures for ethynylcarbinol hydration and oxime reduction to amino alcohols. J. Org.  Chem.. 1975;  40 381-2
• 3 Seidel V, Baileul F, Waterman P G. Goniothalamusin, a linear acetogenin from Goniothalamus gardneri .  Phytochemistry. 1999;  52 1101-3
• 4 Jolad S D, Hoffmann J J, Cole J R, Barry III  C E, Bate R B, Linz G S, Konig W A. Desacetyluvaricin from Uvaria accuminata configuration of uvaricin at C-36. J. Nat.  Prod.. 1985;  48 644-5
• 5 Dieser M J, Hui Y H, Rupprecht J K, Kozlowski J F, Wood K V, Hoye T R. Determination of absolute configuration of stereogenic carbinol centers in Annonaceous acetogenins by ¹H- and ¹⁹F-NMR analysis of Mosher ester derivatives. J. Am. Chem.  Soc.. 1992;  114 10 203-13
• 6 Rosa S D, Milone A, Crispino A, Jaklin A, Giulio A D. Absolute configuration of 2, 6-dimethylheptyl sulfate and its distribution in Ascidiacea. J. Nat.  Prod.. 1997;  60 462-3
• 7 Shanghai Institute of Material M edica. Chinese Academy of Science, Handbook of Flavonoid Identification. Science Press China; 1981: 88-176
• 8 Zhang J S, Shabrawy A RO, Shanawany M A, Shiff P L, Slatkin D J. New azafluorene alkaloids from Oxandra xylopioides. J. Nat.  Prod.. 1987;  50 800-6
• 9 Wu Y C, Duh C Y, Wang S K, Chen K S, Yang T H. Two new natural azafluorene alkaloids and a cytoxic aporphine alkaloid from Polyalthia longifolia. J. Nat.  Prod.. 1990;  53 1327-31
• 10 Leboeuf M, Cave A, Tohami M E, Passet J, Forgacs P, Provost J. Alkaloids of Annonaceae. XXXV. Alkaloids of Desmos tiebaghiensis. J. Nat.  Prod.. 1982;  45 617-23
• 11 Guinaudeau M H, Leboeuf M, Cave A R. J. Nat. Prod. Aporphinoid alkaloids, V.  . 1994;  57 1033-135
• 12 Ternai B, Markham K R. Carbon-13 NMR studies of flavonoids - I Flavones and flavonols.  Tetrahedron.. 1976;  32 565-9