13902-54-0Relevant academic research and scientific papers
Synthesis of 6-epi-tuberiferin and the biological activities of tuberiferin, dehydrobrabrachylaenolide, 6-epi-tuberiferin, and their synthetic intermediates
Li, Dan,Higuchi, Yohsuke,Kobayashi, Takafumi,Shimoma, Fumito,Bai, Yuhua,Ando, Masayoshi
, (2021/02/02)
Tuberiferin, 6-epi-tuberifelin, dehydrobrachylaenolide and two series of eudesmanolides, eudesmane-12,6 α-lactones and eudesmane-12,6β-lactones, were synthesized for the studies of the structure–activity relationships to explore novel anti-inflammatory, a
Biotransformation of 6α-santonin and 1,2-dihydro-α-santonin by Acremonium chrysogenum PTCC 5271 and Rhizomucor pusillus PTCC 5134
Gandomkar, Somayyeh,Habibi, Zohreh
, p. 59 - 63 (2015/01/08)
Biotransformation of 6α-santonin (1) and 1,2-dihyro-α-santonin (2) by two fungal strains Acremoniumchrysogenum (Cephalosporium chrysogenum) and Rhizomucor pusillus has been investigated for the firsttime. After 8 days of incubation of 1 by A. chrysogenum, four known metabolites including 1,2-dihydro-α-santonin (2) (30%), 8α-hydroxyl-α-santonin (3) (22%), 15-hydroxy-α-santonin (4) (15%) and 4,5-dihydro-α-santonin (5) (10%) were obtained. Incubation of 1 by R. pusillus afforded two metabolites 2 (45%) and 3(20%). Biotransformation of 1,2-dihyro-α-santonin by A. chrysogenum produced tetrahydro-α-santonin(6) with 52% yield and tetrahydroartemisin (7) with 33% yield. By R. pusillus, the yields of 6 and 7 were32% and 21%, respectively. The structures of the products were identified on the basis of spectroscopic data.
Identification of natural-product-derived inhibitors of 5-lipoxygenase activity by ligand-based virtual screening
Franke, Lutz,Schwarz, Oliver,Müller-Kuhrt, Lutz,Hoernig, Christina,Fischer, Lutz,George, Sven,Tanrikulu, Yusuf,Schneider, Petra,Werz, Oliver,Steinhilber, Dieter,Schneider, Gisbert
, p. 2640 - 2646 (2008/02/06)
A natural product collection and natural-product-derived combinatorial libraries were virtually screened for potential inhibitors of human 5-lipoxygenase (5-LO) activity. We followed a sequential ligand-based approach in two steps. First, similarity searc
Synthesis of a structurally constrained endoperoxide having antimalarial activity from α-santonin
Van Der Westhuyzen,Parkinson
, p. 41 - 45 (2007/10/03)
α-Santonin 3 was successfully converted into a biologically active compound 5b containing an endoperoxide group through a photo-oxygenation approach as a single isomer. It was found that the singlet oxygen afforded the isomer produced by attack from the sterically-hindered face of cyclohexadiene derivative 4. Evidence to this end is presented based on NOE results and the products formed in the photo-oxygenation reaction, as well as the in vitro testing of 5b for antimalarial activity.
Synthesis of (+)-8-Deoxyvernolepin
Hernandez, Rosendo,Valazquez, Silvia M.,Suarez, Ernesto,Rodriguez, Maria S.
, p. 6395 - 6403 (2007/10/02)
A short and efficient synthesis of (+)-8-deoxyvernolepin (2) from (-)-α-santonin (8), by functionalization of the angular methyl from a 2β- or 6β-alkoxy radical generated by reaction of the alcohol 6 or 7 with diphenylhydroxyselenium acetate and iodine and 1,4-fragmentation of the γ-hydroxystannane 35 using hypervalent organoiodine reagents as the key steps, is described.The most important structural features of this compound and other vernolepin congeners, the δ-valerolactone cis-fused to ring B moiety and the angular vinyl group, are introduced in the same step.
SYNTHESIS OF A NATURAL NOR-SESQUITERPENE-γ-LACTONE
Rossi, Carlo,Papi, Concetta,Barbetti, Paolo
, p. 107 - 110 (2007/10/02)
A five-step synthesis of 3-oxo-5α-H,4,6β-H-11-hydroxyeudesm-1(2),7(11)-dien-6,13-olide, 1, a novel nor-sesquiterpene-γ-lactone isolated from Crepis pygmaea (Compositae), is reported.
STRUCTURE AND SYNTHESIS OF BISSANTANOLIDES
Inayama, Seiichi,Ohsaka, Tetsushi,Shibata, Tetsuichi,Hirose, Tadaaki,Kawamata, Takeshi,et al
, p. 861 - 864 (2007/10/02)
2-Hydroxy-hexahydro-λ-α-santonins (1) and (2) were transformed in reasonable yield to the corresponding bissantanolides (3) and (4) using p-toluenesulfonic acid, respectively.The structures and conformations of (3) and (4) were determined on the basis of their spectral data and X-ray crystallographic analysis of (3).
Preparation, Decarboxylation and Absolute Configuration of (+)-11α-Carboxy- and (+)-11β-Carboxy-3α,4β,5α,6βH-hexahydrosantonin, and (-)-11β-Carboxysantonin
Inayama, Seiichi,Kawamata, Takeshi,Hirose, Tadaaki
, p. 288 - 295 (2007/10/02)
A simple and stereoselective preparation of (-)-11β-carboxysantonin (8a) was achieved by carboxylation of l-α-santonin (5b), based on the non-stereoselective two-step method described earlier. (+)-11β-Carboxy- (3a) and (+)-11α-carboxy-3α,4β,5α,6βH-hexahydrosantonin (3b) were prepared in a ratio of 3:1 by alkoxycarbonylation of 3α,4β,5α,6β,11βH-hexahydrosantonin (HHS) (1a), followed by hydrolysis. The absolute configurations at C-11 in the three optically active 11-carboxysantonins have now been confirmed on the basis of the stereochemistry of the fourth new stereoisomer, (-)-11β-carboxysantonin (8a).The complete structure of 8a was established by its transformation to (+)-11β-carboxy-4β,5α,6βH-tetrahydrosantonin (7a), correlating with 3a.The proton magnetic resonance (PMR) signals of 6β-hydrogens in 11β-carboxy- or 11β-methoxycarbonyl-HHS (2a-4a) are anisotropically shifted further downfield compared to those in the 11α-oriented epimers (2b-4b).A similar result was obtained for the pairs of epimers in the 4β,5α,6β,11βH-tetrahydrosantonin (THS) series (6a,7a and 6b,7b). The stereospecific decarboxylation of the 11β- and 11α-carboxylactone derivatives (3a,7a,8a and 3b,7b,8b) afforded the thermodynamically more stable 11α-methyl lactone analogs (1a,5a,5b), and not the 11β-methyl epimers (1c,5c,5d).The rate of decarboxylation of the former lactone acids was faster than that of the latter, supporting the foregoing assignments, based on spectral data, for the configurations of the 11β- and 11α-carboxyl groups. Keywords---(-)-11β-carboxysantonin; (+)-11β-carboxysantonin; (-)-11α-carboxysantonin; (+)-11α-carboxysantonin; (+/-)-11β-carboxysantonin; (+/-)-11α-carboxysantonin; (+)-11β-carboxy-3α,4β,5αH-hexahydrosantonin; (+)-11α-carboxy-3α,4β,5αH-hexahydrosantonin; stereoselective preparation; stereospecific decarboxylation
