Title

Chemical constituents of twelve Philippine endemic species of the family cycadaceae

Date of Publication

2016

Document Type

Dissertation

Degree Name

Doctor of Philosophy in Chemistry

Subject Categories

Chemistry

College

College of Science

Department/Unit

Chemistry

Thesis Adviser

Consolacion Y. Ragasa

Defense Panel Chair

Jaime Raul O. Janairo

Defense Panel Member

Glenn V. Alea
Marissa G. Noel

Abstract/Summary

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)

Abstract Format

html

Language

English

Format

Electronic

Accession Number

CDTG006152

Shelf Location

Archives, The Learning Commons, 12F Henry Sy Sr. Hall

Keywords

Cycadaceae; Species; Cycas

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