Activity-Guided Isolation of Triterpenoid Acyl CoA Cholesteryl Acyl Transferase (ACAT) Inhibitors from Ilex kudincha

Abstract

Activity-guided fractionation of a methanol extract of the leaves of Ilex kudincha led to the isolation of seven acyl CoA cholesteryl acyl transferase (ACAT) inhibitory triterpenes. Four of them were identified by spectroscopic methods as ulmoidol (4), 23-hydroxyursolic acid (5), 27-trans-p-coumaroyloxyursolic acid (6), and 27-cis-p-coumaroyloxyursolic acid (7), and three were new compounds named ilekudinols A-C (1-3). The structures of these new triterpenoids were elucidated as 2alpha, 3beta-dihydroxy-24-nor-urs-4(23),11-dien-28,13beta- olide (1), 2alpha, 3beta-dihydroxy-24-nor-urs-4(23),12-dien-28-oic acid (2), and 3beta, 24,28-trihydroxylupane (3). Compounds 1-7 showed potent inhibitory activity in the ACAT assay.

Protein tyrosine phosphatase 1B inhibitory activity of 24‐norursane triterpenes isolated from Weigela subsessilis

“…(40 : 60) (YMC SH-843-5 C4 column; 20 × 250 mm; 4 mL/min; UV detection at 210 nm), to afford compounds 1 (6.2 mg) and 2 (15.3 mg). C-NMR spectral data were in accordance with published data (Nishimura et al, 1999). C-NMR spectral data were in accordance with published data (Nishimura et al, 1999).…”

“…C-NMR spectral data were in accordance with published data (Nishimura et al, 1999). C-NMR spectral data were in accordance with published data (Nishimura et al, 1999). PTP1B assay.…”

Palmitoleate (=(9Z)‐Hexadeca‐9‐enoate) Esters of Oleanane Triterpenoids from the Golden Flowers of Tagetes erecta: Isolation and Autoxidation Products

“…This was confirmed by the 13 C-NMR spectrum (Table 2) [12]. The a,bunsaturated-ketone moiety was also substantiated by the HR-EI-MS, which showed two important fragments at m/z 273.2201 (C 19 Autoxidation Products of 1 and 5. The 2D-NMR spectra run for further strengthening of the structure of the new natural product 1 revealed its decomposition to a mixture of compounds by autoxidation (aerial oxidation).…”

Anti-complementary Activity of Ursane-Type Triterpenoids from Weigela subsessilis

“…The structures of seven known compounds (Fig. 1) were identified as ursolic acid (2), 21) ilekudinol A (3), 22) corosolic acid (4), 23) ilekudinol B (5), 22) esculentic acid (6), 24) pomolic acid (7), 25) and asiatic acid (8) 26) by comparing their spectral (IR, 1 H-and ϩ in HR-FAB-MS. Its IR spectrum showed absorption bands deduced to be hydroxy groups at 3400 cm Ϫ1 and a carbonyl group at 1700 cm Ϫ1 attributed to a carboxylic group. The 1 H-NMR spectrum of 1 revealed an olefinic proton at d 5.14 (br s), three methine protons at 27) These findings suggested a tetrahydroxyl substitution on ring A of an ursane-type triterpenoid for 1.…”