ABSTRACTChemical investigation of Cycas vespertilio A. Lindstr. & K.D. Hill, Cycadaceae, a plant endemic to the Philippines, yielded pinoresinol (1), sesamin (2), paulownin (3), a mixture of β-sitosterol and stigmasterol, and triacylglycerols from the cone base; 1, 3, β-sitosterol, stigmasterol, triacylglycerols, and lariciresinol (4) from the cataphylls; β-sitosterol from the megasporophyll lamina; β-sitosterol and a mixture of trans-4-hydroxycinnamate fatty acid esters (5) and cis-4-hydroxycinnamate fatty acid esters (6) from the unripe sarcotesta; and β-sitosterol and triacylglycerols from the ripe sarcotesta. The structures 1–6 were elucidated by extensive 1D and 2D NMR spectroscopy.

Abstract Chemical investigation of the dichloromethane extracts of the propolis collected from bee (Tetragonula biroi Friese) hives in San Roque, Sorsogon, Philippines afforded propolin A (1), propolin E (2), propolin H (3), glyasperin A (4), squalene, a mixture of lupeol, α-amyrin and β-amyrin, and another mixture of urs-12-en-3-one, olean-12-en-3-one and lup-12-en-3-one. The structures of 2–4 were elucidated by extensive 1D and 2D (COSY, HSQC, and HMBC) NMR spectroscopy, while 1 was identified by comparison of its NMR data with 2.