Melipatulinones A–C, Three Lignan–Phloroglucinol Hybrids from Melicope patulinervia

• Published in: Organic letters Vol. 22; no. 4; pp. 1380 - 1384
• Main Authors: Vu, Van-Tuan, Chen, Xin-Lin, Kong, Ling-Yi, Luo, Jian-Guang
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 21.02.2020; Amer Chemical Soc
• Subjects: chemical reactions; chemical structure; Chemistry; Chemistry, Organic; circular dichroism spectroscopy; enzyme inhibition; leaves; Melicope; organic compounds; Physical Sciences; Science & Technology; triacylglycerol lipase; X-ray diffraction; TETRAHYDROFURAN LIGNANS; ECBALLIUM-ELATERIUM-L; CONSTITUENTS
• ISSN: 1523-7060; 1523-7052; 1523-7052
• DOI: 10.1021/acs.orglett.9b04680

(±)-Melipatulinones A–C (1–3), three unique enantiomeric pairs of lignan–phloroglucinol hybrids along with the biogenetically related compound melipatulignan A (4), were isolated from the leaves of Melicope patulinervia. Melipatulinones A (1) and B (2) share a novel spiro­[hydrobenzo­furan-2,3′-furan] 5/5/6 tricyclic ring system, while melipatulinone C (3) features an unprecedented spiro­[cyclo­penta­[b]­hydro­furan-2,3′-furan] 5/5/5 tricyclic framework. Their structures were determined by spectroscopic methods, electronic circular dichroism (ECD) calculations, and X-ray diffraction. Compounds 1–3 exhibited a pancreatic lipase inhibitory effect.