New Norsesquiterpenoids from Cucubalus baccifer

Abstract

The chemical investigation of Cucubalus baccifer L. afforded three new norsesquiterpenoids, cucubalol, cucubalactone and drummondol-11-O-beta-D-glucopyranoside together with two known related compounds, drummondol and 5,7[E]-megastigmadiene-3 beta,4 alpha,9 xi-triol. Their structures were established based on spectral and chemical evidence. No activity was observed in anti-cancer (CDC25), antibacterial (PEPT) and antifungal (YNG) assays.

Anti-complementary constituents of Anchusa italica

“…13 C NMR (DMSO-d 6 , 101 MHz) δ: 208.7(C-3), 139.6(C-2′), 123.8(C-1′), 85.5(C-8), 80.5(C-5), 76.5(C-7), 66.5(C-3′), 52.9(C-4), 51.9(C-2), 47.5(C-1), 24.2(3′-CH3), 19.0 (5-CH3), 15.2 (1-CH3). It was identified as Drummondol by comparison of the spectral data with those reported (Cheng et al 2002) -29 (c = 0.15, MeOH); 1 H NMR (CD 3 OD, 400 MHz) δ: 2.35 (1H, m, H-2), 2.69 (1H, d, J = 17.6 Hz, H-2), 2.37 (1H, m, H-4), 2.68 (1H, d, J = 17.6 Hz, H-4), 6.07 (1H, m, H-7), 6.18 (1H, dd, J = 15.4, 6.3 Hz, H-8), 4.42 (1H, m, H-9), 1.29 (3H, d, J = 6.4 Hz, H-10), 3.60 (1H, d, J = 7.6 Hz, H-11), 3.87 (1H, dd, J = 7.6, 2.8 Hz, H-11), 0.95 (3H, s, H-12), 1.13 (3H, s, H-13), 4.32 (1H, d, J = 7.8 Hz, H-1′), 3.14 (1H, dt, J = 7.9, 6.6 Hz, H-2′), 3.21 (1H, m, H-3′), 3.21 (1H, m, H-4′), 3.27 (1H, dt, J = 3.3, 1.6 Hz, H-5′), 3.60 (1H, m, H-6′), 3.82 (1H, dd, J = 11.6, 1.6 Hz, H-6′). 13 C NMR (CD 3 OD, 101 MHz) δ: 211.3 (C-3), 139.0 (C-8), 127.2 (C-7), 102.6 (C-1′), 87.4 (C-5), 82.3 (C-6), 78.4 (C-11), 78.0 (C-3′), 77.9 (C-5′), 77.4 (C-9), 75.1 (C-2′), 71.7 (C-4′), 62.8 (C-6′), 54.0 (C-4), 53.1 (C-2), 48.9 (C-1), 21.4 (C-10), 19.1 (C-13), 15.9 (C-12).…”

Ebenamariosides A–D: Triterpene Glucosides and Megastigmanes from the Leaves of <i>Diospyros maritima</i>

“…The 1 H-NMR signal of the H-3 proton of 6d was appeared as a doublet of a doublet, J = 5.7, 5.7 Hz, indicating that the α-hydroxy group formed at the 3-position was in the pseudo axial orientation due to steric hindrance toward the epoxide ring. 19,20) Meanwhile, the NMR spectroscopic data of the minor one (6c) were identical with those of 5 and similarly 6c was subjected to the modified Mosher's method to give (R)-and (S)-α-methoxy-α-trifluoromethylphenylacetic acid (MTPA) esters of 6c, which were the identical compounds with 5a and 5b from 5. Therefore, the absolute configurations of drummondol (6) isolated in this experiment was confirmed to be 1R,5R,6S,9S, which was the same as the aglycone of (9S)-drummondol 9-O-β-D-glucopyranoside from C. spinosa (Fig.…”

Natural sesquiterpenoids

“…27 Cucubalol 28, cucubalactone 29 and drummondol-11-O-β-glucopyranoside 30 are three norsesquiterpenes which have been isolated from Cucubalus baccifer, a plant used for the treatment of pulmonary tuberculosis in Chinese folk medicine. 28 Bakayanolide 31 is a C 11 terpene which has been found in the roots of Melia azedarach. 29 Enantioselective syntheses of both enantiomers of γ-ionone, γ-damascone, karahana lactone and karahana ether have been carrried out.…”