Flavonoids from Amazonian leguminosae

Phytochemistry
1973.0

Abstract

Identification of the constituents relied upon direct comparison (m.m.p., IR, PMR, co-TLC) of IIIb and of IV resp. with (6S)-dihydromethysticin3 and anibine;2 and upon comparison of m.p. and UV spectra of IIIa and of IIIc with lit. data resp. of dihydrokawain6,7 and tetrahydroiangonin.6,7 Tetrahydro-11-methoxyiangonin (IIId). White plates, m.p. 121-123° (C6H6). v_max (cm-1): 1708, 1694, 1623, 1526, 1412, 1389, 1370, 1281, 1252, 1230, 1220, 1154, 1134, 1040, 1028, 1002, 988, 830, 817, 645. λ_FQY^FQY(nm): 231, 277, 284sh (τ 17 800, 3400, 2800). PMR (CDCl3, τ) of IIIa,b,c,d: 4.88 (s, H-3), 5.40-5.90 (m, H-6), 6.33 (s, OCH3), 7.15–7.35 (m, ArCH2), 7.55–7.75 (m, two H-5), 7.80–8.25 (m, ArCH2CH2). Additional features of the PMR spectra of IIIa: 2.87 (s, five ArH). IIIb: 3.37 (s, three ArH), 4.14 (s, O2CH2). IIIc: 2.90 and 3.20 (approx. doublets, J8 Hz, AA'BB' system), 6.23 (s, OCH3). IIId: 3.30 (s, three ArH), 6.21 (s, OCH3), 6.25 (s, OCH3). MS. IIIa: M 232 (60%), m/e 91 (100%). IIIb: M 276 (97%), m/e 135 (70%). IIIc: M 262 (37%), m/e 121 (100%). IIId: 292 (45%), m/e 151 (100%). ORD (EtOH, c 1.0, 400–210 nm).IIIa: [φ]317 O, [φ]248 O, [φ]248 O, [φ]255 - 20 880. IIIb: [φ]298 O, [φ]260 +12 420, [φ]6 HÄNSEL, R., LANGHAMMER, L. and RIMPLER, H. (1967) Arch. Pharm. 300, 157.7 KLOHS, M. W., KELLER, F., WILLIAMS, R. E., TOEKES, M. I. and KRONHEIM, G. E. (1959) J. Med. Pharm. Chem. 1, 95.

Knowledge Graph

Similar Paper