Constituents of the Trunk Resin ofEperua leucantha

Abstract

Constituents of the Trunk Resin of Eperua leucantha 229 C. patens roots were collected in December, 1983 in lie, Nigeria and steam distilled to yield an essential oil (0.045%). The oil was analysed by GC (DB-5 coated capillary column; 30 m x 0.25 mm i.d.) and GC-MS (3% OV 17 coated stainless steel column; 2 m X 0.5 mm i.d.); oven temperature :70° C-220°C References (1) Dalziel, J. M. (1937) The Useful Plants of West Tropical Africa, p. 3, Crown Agents, London.

A New Clerodane-Type Diterpenoid from Eperua leucantha

“…Anal, found C 75.5, H 10.3%; C21H340, requiresC 75.4, 10.4 %. [<x}25d -10°(r= 0.15, CHC13); ir (KBr) v max 3350, 3000, 2920, 2870, 1720, 1644, 1225, 1150 cm™1; nmr (CDCI3) 0.74 (3H, s, H-I9), 0.81 (3H, dj = 6.3 Hz, H-18), 1.04(3H, s, H-20), 2.15 (3H, d,J= 1.2 Hz, H-16), 3.68(3H, s, OMe), 4.27-4.30 (1H, ddj"," = 12 Hz Jueq = 6 Hz, -7 ), 4.73 (1H, bs, ,-17), 4.92 (1H, bs, Hb-17), 5.64 (1H, bs, H-14); ,3C nmr (CDC13, 75.5 MHz) see Isolation of norhardwikiic acid methyl ester [2],-The least polar compound of the above cited tic was a colorless oil: [ ]25 -70°(r = 0.3, CHCl,); ir (film) v max 2957, 2929, 1731, 1662, 1437, 1239 cm™1; 'H nmr (CDC1,) 300 MHz 0.77 (3H, s, H-20), 0.81 (3H, dJ = 6Hz, H-17), 1.25 (3H, s, H-19), 3.66(3H, s, OMe), 3.68(3H, s, OMe), 6.6(1H, t J= 3 Hz, H-3); i3C nmr(CDCl3, 75.5 Isolation of 16-oxo-15,16H-Hardwikiic acid methyl ester [3].-The same preparative layer afforded another colorless oil: [a]2SD -70°(r= 0.3, CHC13); uv X max (EtOH) 213 nm(loge 3.8); ir (film) v max 3020, 2957, 2930, 1753, 1708, 1435, 1233 cm™'; *H nmr (CDC13 300 MHz 0.77 (3H, s, H-20), 0.82 (3H, d,/ = 7 Hz, H-17), 1.26 (3H, s, H-19), 3.68 (3H, s, OMe), 4.77 (2H, bs, H-15), 6.62 (1H, t,/ = 3 Hz, H-3), 7.12(1H, s, H-16); 13C nmr (CDC13, 75.5 MHz) see Table 1; eims Vz (%) [M]+ (C21H30O4) 346; CM -MeOH]+ 314(100), [M -MeOH -151+ 299 (7), 271 (16), 235 (10), 175 (66), 139(75), 107 (65).…”

Structurally Diverse Labdane Diterpenoids from Leonurus japonicus and Their Anti-inflammatory Properties in LPS-Induced RAW264.7 Cells

“…Five out of six compounds (25−29) with this feature were identified as active (IC 50 < 50 μM), and the only inactive one (24) contains a bulky group connected to C-4. The other favorable fragment (B) highlighted the compounds with no polar substitutions at C-3, C-5, and C-6, and all three compounds containing this substructure (23,27,28) inhibited NO production. The unfavorable substructure was suggested as a furan ring on a C 2 chain connected to the oxygenated carbon at C-9 (C).…”

“…In addition to the above 18 new compounds, 20 known labdane diterpenoids including leojapone B ( 3 ), leojapone A ( 4 ), leojaponin ( 5 ), heteronone B ( 6 ), 6β-hydroxy-15,16-epoxylabda-8,13(16),14-trienone ( 7 ), heteronone A ( 8 ), 15,16-epoxy-6β,9α-dihydroxylabda-13(16),14-diene-3,7-dione ( 9 ), leoheterin ( 10 ), leojapone D ( 13 ), leojaponin C ( 14 ), 6β-15,16-epoxy-15-ethoxy-6,13-dihydroxylabd-8-en-7-one ( 15 ), sibiricinone C ( 22 ), leoheteronin B ( 23 ), leojaponin D ( 25 ), leojaponin B ( 26 ), labda-7,13 E -dien-15-ol ( 27 ), 8(17),13 E -labdien-15-ol ( 28 ), illenol ( 29 ), 1-{(1 S ,3 R ,3a S )-3-[2-(furan-3-yl)­ethyl]-3-methoxy-3a,7,7-trimethyloctahydroisobenzofuran-1-yl}­propan-1-one ( 35 ), and seco -labdane ( 36 ) were also isolated and identified from this plant. Their structures (Figure ) were elucidated by comparison of their NMR and MS data with reported literature.…”

The amide derivative of anticopalic acid induces non-apoptotic cell death in triple-negative breast cancer cells by inhibiting FAK activation

“…Anticopalic acid ( ACP ) known as (+)-copalic acid (Fig. 1 ), is a labdane-type bicyclic diterpenoid previously isolated from several plants including Vitex hemsley 9 , Eperua purpurea 10 , Eperua leucantha 11 , Pinus monticola 12 , 13 , Pinus strobus 13 , and Oxystigma oxyphyllum 14 , 15 . In 2018, our group isolated ACP in large amounts (~ 23%) from the crude extract of the rhizomes of Kaempferia elegans 16 , 17 .…”