22595-48-8Relevant articles and documents
18-OXOFERRUGINOL FROM THE LEAF OF TORREYA NUCIFERA
Harrison, Leslie J.,Asakawa, Yoshinori
, p. 1211 - 1212 (1987)
From the leaf of the conifer Torreya nucifera, a new diterpenoid has been isolated and shown to be 18-oxoferruginol (12-hydroxy-8,11,13-abietatrien-18-al) on the basis of its spectroscopic properties and its chemical conversion to the known 18-hydroxyferruginol (8,11,13-abietatriene-12,18-diol). - Key Word Index: Torreya nucifera; Taxaceae; diterpenoids; abietanes; 18-oxoferruginol.
Synthesis and Biological Studies of (+)-Liquiditerpenoic Acid A (Abietopinoic Acid) and Representative Analogues: SAR Studies
Hamuli?, Damir,Stadler, Marco,Hering, Steffen,Padrón, José M.,Bassett, Rachel,Rivas, Fatima,Loza-Mejía, Marco A.,Dea-Ayuela, M. Auxiliadora,González-Cardenete, Miguel A.
supporting information, p. 823 - 831 (2019/03/19)
The first semisynthesis and biological profiling of the new abietane diterpenoid (+)-liquiditerpenoic acid A (abietopinoic acid) (7) along with several analogues are reported. The compounds were obtained from readily available methyl dehydroabietate (8), which was derived from (-)-abietic acid (1). Biological comparison was conducted according to the different functional groups, leading to some basic structure-activity relationships (SAR). In particular, the ferruginol and sugiol analogues 7 and 10-16 were characterized by the presence of an acetylated phenolic moiety, an oxidized C-7 as a carbonyl, and a different functional group at C-18 (methoxycarbonyl, carboxylic acid, and hydroxymethyl). The biological properties of these compounds were investigated against a panel of six representative human tumor solid cells (A549, HBL-100, HeLa, SW1573, T-47D, and WiDr), five leukemia cellular models (NALM-06, KOPN-8, SUP-B15, UoCB1, and BCR-ABL), and four Leishmania species (L. infantum, L. donovani, L. amazonensis, and L. guyanensis). A molecular docking study pointed out some targets in these Leishmania species. In addition, the ability of the compounds to modulate GABAA receptors (α1β2γ2s) is also reported. The combined findings indicate that these abietane diterpenoids offer a source of novel bioactive molecules with promising pharmacological properties from cheap chiral-pool building blocks.
First synthesis of picealactone C. A new route toward taxodione-related terpenoids from abietic acid
Alvarez-Manzaneda, Enrique,Chahboun, Rachid,Cabrera, Eduardo,Alvarez, Esteban,Alvarez-Manzaneda, Ramón,Lachkar, Mohammed,Messouri, Ibtissam
, p. 989 - 992 (2008/02/04)
A new route to 12-hydroxyabietic acid (10) and related compounds from abietic acid (12), via acetoxyalcohol 15, is reported. Utilizing this, the first synthesis of picealactone C (5) was achieved. The synthesis of natural 12-hydroxydehydroabietic acid (8), 18-hydroxyferruginol (9) and methyl 12α-hydroxyabietate (11) is also reported.