Structure and Absolute Configuration of Diterpenoids from Hymenaea stigonocarpa

Structure and Absolute Configuration of Diterpenoids from Hymenaea stigonocarpa

Chemical investigations of the ethanolic extracts from the flowers and leaves of Hymenaea stigonocarpa Mart. ex Hayne afforded one new ent-halimane diterpenoid, 18-hydroxy-ent-halima-1­(10),13-(E)-dien-15-oic acid (1), together with five known compounds (2–6). The structural elucidation was performe...

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Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2015-06, Vol.78 (6), p.1451-1455
Hauptverfasser: Monteiro, Afif F, Batista, João M, Machado, Michelle A, Severino, Richele P, Blanch, Ewan W, Bolzani, Vanderlan S, Vieira, Paulo C, Severino, Vanessa G. P
Format: Artikel
Sprache:eng
Schlagworte:
Brazil
Diterpenes - chemistry
Diterpenes - isolation & purification
Flowers - chemistry
Hymenaea - chemistry
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Leaves - chemistry
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Beschreibung
Zusammenfassung:Chemical investigations of the ethanolic extracts from the flowers and leaves of Hymenaea stigonocarpa Mart. ex Hayne afforded one new ent-halimane diterpenoid, 18-hydroxy-ent-halima-1­(10),13-(E)-dien-15-oic acid (1), together with five known compounds (2–6). The structural elucidation was performed by means of NMR (COSY, HSQC, HMBC, and NOESY) and MS analyses. Complete 1H and 13C NMR data assignments are also reported for labd-13-en-8β-ol-15-oic (2) and labd-7,13-dien-15-oic (3) acids. The absolute configurations of 1 and 2 were established by comparison of experimental and calculated Raman optical activity spectra.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.5b00166