536 0009-3130/16/5203-0536  2016 Springer Science+Business Media New York Chemistry of Natural Compounds, Vol. 52, No. 3, May, 2016 TERPENOIDS AND STEROLS FROM Cycas vespertilio Consolacion Y. Ragasa, 1,2* Vincent Antonio S. Ng, 2 Esperanza Maribel G. Agoo, 3 and Chien-Chang Shen 4 Cycas vespertilio A. Lindstr. & K. D. Hill of the family Cycadaceae is one of the 12 cycad species found in the Philippines. Ten of these species are endemic to the Philippines, namely C. aenigma K. D. Hill & Lindstrom, C. curranii (J. Schust.) K. D. Hill, C. lacrimans Lindstrom & K. D. Hill, C. nitida K. D. Hill & Lindstrom, C. riuminiana Porte ex Regel, C. saxatilis K. D. Hill & Lindstrom, C. sancti-lasallei Agoo & Madulid, C. wadei Merr., C. vespertilio Lindstrom & K. D. Hill, and C. zambalensis Madulid & Agoo [1–3]. C. edentata de Laub. is not Philippine endemic, while C. revoluta is an introduced species from Japan and Taiwan. We earlier reported the isolation of pinoresinol, lariciresinol, mixtures of -amyrin acetate and lupeol acetate, -sitosterol and stigmasterol, triglycerides, and fatty alcohols from the male cone of C. vespertilio [4]. We also reported the isolation of pinoresinol, sesamin, paulownin, a mixture of -sitosterol and stigmasterol, triacylglycerols, and lariciresinol from the cataphylls; -sitosterol from the megasporophyll lamina; -sitosterol and a mixture of trans-4-hydroxycinnamate fatty acid esters and cis-4-hydroxycinnamate fatty acid esters from unripe sarcotesta, and -sitosterol and triacylglycerols from the ripe sarcotesta of C. vespertilio [5]. Chemical investigation of Cycas vespertilio, a plant endemic to the Philippines, led to the isolation of 9H-isopimara-7,15-diene (1), squalene (2), -sitosterol (3), and stigmasterol (4) from the bark; 2, 3 and phytyl fatty acid ester (5) from the petiole and rachis; 3–5 and triglycerides (6) from the endotesta; 1–3, 6 and adianenone (7) from the roots; 3, 4, 6 and chlorophyll a from the leaflets; and 3 and 6 from the sclerotesta. The structures of 1, 5, and 7 were elucidated by extensive 1D and 2D NMR spectroscopy. This is the first report on the occurrence of 7 in the genus Cycas and the family Cycadaceae. NMR spectra were recorded on a Varian VNMRS spectrometer in CDCl 3 at 600 MHz for 1 H NMR and 150 MHz for 13 C NMR spectra. Column chromatography was performed with silica gel 60 (70–230 mesh). Thin-layer chromatography was performed with plastic-backed plates coated with silica gel F 254 , and the plates were visualized by spraying with vanillin/H 2 SO 4 solution followed by warming. Cycas vespertilio A. Lindstr. & K. D. Hill bark, petiole and rachis, endotesta, roots, leaves, and sclerotesta were collected from Iloilo, Panay Island, Philippines in April 2013. Voucher specimens were collected and authenticated by one of the authors (EMGA) and deposited in the De La Salle University-Manila Herbarium (DLSUH 3112). The crude extracts were fractionated by silica gel chromatography eluted with increasing proportions of acetone in CH 2 Cl 2 at 10% increment. A glass column 18 inches in height and 1.0 inch internal diameter was used for the fractionation of the crude extracts. Ten-milliliter fractions were collected. Fractions with spots of the same R f values were combined and rechromatographed in appropriate solvent systems until TLC pure isolates were obtained. A glass column 12 inches in height and 0.5 inch internal diameter was used for the rechromatography. Five-milliliter fractions were collected. Final purifications were conducted using Pasteur pipettes as columns. One-milliliter fractions were collected. 1) Chemistry Department, De La Salle University Science & Technology Complex, Leandro V. Locsin Campus, Binan City, 4024, Laguna, Philippines; 2) Chemistry Department and Center for Natural Sciences and Ecological Research, De La Salle University, 2401 Taft Avenue, 1004, Manila, Philippines, fax: (+0632) 536 02 30, e-mail: consolacion.ragasa@dlsu.edu.ph; 3) Biology Department and Center for Natural Sciences and Ecological Research, De La Salle University, Manila, Philippines; 4) National Research Institute of Chinese Medicine, 155-1, Li-Nong St., Sec. 2, 112, Taipei, Taiwan. Published in Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2016, pp. 464–466. Original article submitted July 23, 2014. DOI 10.1007/s10600-016-1702-8