Chemical constituents of twelve Philippine endemic species of the family cycadaceae

• Main Author: Ng, Vincent Antonio S.
• Format: text
• Language: English
• Published: Animo Repository 2016
• Subjects: Cycadaceae; Species; Cycas; Chemistry
• Online Access: https://animorepository.dlsu.edu.ph/etd_doctoral/1204
• Institution: De La Salle University

Air dried leaves, petiole and rachis, roots, bark, megasporophyll lamina, sclerotesta, and cataphylls as well as freeze dried sarcotesta, endotesta and cone of twelve Philippine endemic Cycas species of the family Cycadaceae were separately grounded and soaked with dichloromethane for three days. The secondary metabolites from the separate crude extracts were isolated by silica gel column chromatography. The isolated compounds were characterized and the structures elucidated using extensive 1D and 2D NMR analyses. The structures of new compounds are confirmed through Mass spectral and HRMS analyses. The twelve endemic species studied were Cycas aenigma, Cycas curanii, Cycas flabellata, Cycas lacrimans, Cycas mindanaensis, Cycas nitida, Cycas riuminiana, Cycas sancti lasellei, Cycas saxatilis, Cycas vespertilio, Cycas wadei, and Cycas zambalensis. Two new compounds were isolated from dichloromethane extract of the Philippine endemic Cycas species namely 2α,18-dihydroxy-9-isopimara-7,15-diene (29) which is an isopimarane-type diterpene from the leaflets of Cycas sancti lasellei and a pterocarpan-type isoflavonoid 3,4-dihydroxy-8-methoxy-pterocarpan which we assign the name wadeiol (36) from the roots of Cycas wadei. The other compounds isolated in the Philippine endemic Cycas plants are pinoresinol (1), fatty alcohols (2), 2-[2-hydroxy-5-(3-hydroxypropyl)-3-methoxyphenyl]-1-(4-hydroxy-3-methoxy phenyl) propane-1,3-diol (3), β-sitoterol (4), stigmasterol (5), triglycerides (6), squalene (7), phytyl fatty acid esters (8), β- sitosteryl fatty acid esters (9), lutein (10), phytol (11), 1-alkene (12), β-sitosterone (13), hydrocarbons (14), isopimaran-19-ol (15), 9αH-isopimara-7,15-diene (16), trans-4-hydroxycinnamate fatty acid esters (17) and cis-4-hydroxycinnamate fatty acid esters (18), β-sitosteryl-3β-glucopyranoside-6'-O-palmitate (19), fatty acid methyl esters (20) monoacylmonogalactosylglycerol (21), α-tocopherol (22), labda-8(17), 13(16), 14-trien-18-ol (23), 18-hydroxy-isopimara-7,15-diene (24), abietatriene (25), sesamin (26), 4-hydroxymethyl-3,5-dimethyldihydrofuranone (27), 8-hydroxypinoresinol (28), unsaturated fatty acids (30), adianenone (31), paulownin (32), lariciresinol (33), α-amyrin acetate (34), lupeol acetate (35), selin-4(15)-en-1β,11-diol (37), trilinolein (38), β-carotene (39), dihydrodehydrodiconiferyl alcohol (40), balanophonin (41), and 3-oxoisopimara-7,15-diene (42)