Structure and Absolute Configuration of Diterpenoids from Hymenaea stigonocarpa

• Published in: Journal of natural products (Washington, D.C.) Vol. 78; no. 6; pp. 1451 - 1455
• Main Authors: 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: Journal Article
• Language: English
• Published: United States American Chemical Society and American Society of Pharmacognosy 26-06-2015
• Subjects: Brazil; Diterpenes - chemistry; Diterpenes - isolation & purification; Flowers - chemistry; Hymenaea - chemistry; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plant Leaves - chemistry; Brazil
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.5b00166

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.