Secomultiflorane-type triterpenoid acids from stem bark of Sandoricum koetjape

(+)-23,24-Dinor-3α,9α-epoxy-11-oxo-5β-cholan-22-oic acid: mutual carboxyl-to-ether dimeric hydrogen bonding in a steroidal carboxy–keto ether

“…For keto acids, the five solid-state motifs known, in order of diminishing prevalence, are: acid dimerization , carboxyl-toketone catemerization (Zewge et al, 1998), intramolecular hydrogen-bond formation (Thompson et al, 1996), carboxyl-to-ketone dimerization (Kosela et al, 1995) and acid-to-acid catemerization . For keto acids, the five solid-state motifs known, in order of diminishing prevalence, are: acid dimerization , carboxyl-toketone catemerization (Zewge et al, 1998), intramolecular hydrogen-bond formation (Thompson et al, 1996), carboxyl-to-ketone dimerization (Kosela et al, 1995) and acid-to-acid catemerization .…”

“…Cases of carboxyl-to-ketone dimerization are among the rarest modes of hydrogen bonding in keto acids (Peeters et al, 1983;Abell et al, 1991;Kosela et al, 1995), but in this instance the ketone takes no part in the hydrogen bonding. Cases of carboxyl-to-ketone dimerization are among the rarest modes of hydrogen bonding in keto acids (Peeters et al, 1983;Abell et al, 1991;Kosela et al, 1995), but in this instance the ketone takes no part in the hydrogen bonding.…”

D:C-Friedooleanane-Type Triterpenoids from Lagenaria siceraria and Their Cytotoxic Activity

“…In our preliminary assay, the methanolic extract of the stems of L. siceraria exhibited cytotoxic activity against the SK-Hep-1 cell line (human hepatoma), which led us to investigate its bioactive principles. This resulted in the isolation of four new D:C-friedooleanane-type triterpenes, 3b-O-(E)-feruloyl-D:Cfriedooleana-7,9(11)-dien-29-ol (1), 3b-O-(E)-coumaroyl-D:Cfriedooleana-7,9(11)-dien-29-ol (2), 3b-O-(E)-coumaroyl-D:Cfriedooleana-7,9(11)-dien-29-oic acid (3), and methyl 2b,3b-dihydroxy-D:C-friedoolean-8-en-29-oate (6), together with five known triterpenes with the same skeleton, 3-epikarounidiol (4), 4) 3-oxo-D:C-friedoolena-7,9(11)-dien-29-oic acid (5), 4) bryonolol (7), 5) bryononic acid (8), 6) and 20-epibryonolic acid (9). 7) This paper deals with the extraction, purification, and structural elucidation of those constituents on basis of spectroscopic analysis, as well as the antineoplastic in vitro evaluation of these compounds.…”

Two New Analogues of Trijugin-Type Limonoids from the Leaves of Sandoricum koetjape

“…1,2) A variety of bioactive triterpenoids including limonoids, polyalcohols, meso-inositol and dimethyl mucate have been isolated from this species previously. [3][4][5][6][7][8] In a previous paper, we described the characterization of koetjapic acid and 3-oxo-olean-12-en-29-oic acid as inhibitors against activation of Epstein-Barr virus early antigen induced by tumor promoter and as ichthyotoxic principles, in the bark of S. koetjape. 9) We have also reported the structures of new modified limonoids, sandrapins A (1), B (2) and C (3) isolated from an EtOAc extract of the leaves of the plant.…”