468-68-8Relevant articles and documents
Practical isolation of polygodial from Tasmannia lanceolata: A viable scaffold for synthesis
Just, Jeremy,Jordan, Timothy B.,Paull, Brett,Bissember, Alex C.,Smith, Jason A.
, p. 11200 - 11207 (2015)
Polygodial, a valuable sesquiterpene dialdehyde featuring an epimerizable stereocenter was efficiently extracted and isolated in gram-scale quantities (3.3% w/w) from Tasmannia lanceolata (Tasmanian native pepper) via a recently developed rapid pressurised hot water extraction (PHWE) technique that utilises an unmodified household espresso machine. This method was compared to the maceration of T. lanceolata under a range of conditions. Polygodial was used to achieve semi-syntheses of closely related sesquiterpene natural products drimendiol, (-)-drimenol, (+)-euryfuran, and some non-natural derivatives.
Elimination of C-8-functional groups from driman-8α,11-diol-11- monoacetate and-diacetate
Kuchkova,Aryku,Barba,Vlad
, p. 412 - 416 (2007)
The dehydration products of driman-8α,11-diol-11-monoacetate that are formed upon reaction with several dehydrating agents and the products from elimination of the C-8 acetoxy group in driman-8α,11-diol diacetate were investigated in detail. A new effective synthesis of drimenylacetate from driman-8α, 11-diol-11-monoacetate by its regioselective dehydration using methanesulfonic acid trimethylsilyl ether was developed.
Synthesis and bio-inspired optimization of drimenal: Discovery of chiral drimane fused oxazinones as promising antifungal and antibacterial candidates
Li, Dangdang,Zhang, Shasha,Song, Zehua,Li, Wei,Zhu, Feng,Zhang, Jiwen,Li, Shengkun
, p. 558 - 567 (2017/12/07)
The synthesis of antifungal natural product drimenal was accomplished. Bio-inspired optimization protruded chiral 8-(R)-drimane fused oxazinone D as a lead, considering favorable physicochemical profiles for novel pesticides. The improved scalable synthesis of scaffold D was implemented by Hofmann rearrangment under mild conditions. Detailed structural optimization was discussed for both antifungal and antibacterial exploration. Substituted groups (SGs) with C3～C5 hydrocarbon chain are recommended for exploration of antifungal agents, while substituents with C4～C6 carbon length are preferred for antibacterial ingredients. The chiral drimane fused oxazinone D8 was selected as a promising antifungal candidate against Botrytis cirerea, with an EC50 value of 1.18 mg/L, with the enhancement of up to >25 folds and >80 folds than the mother compound D, and acyclic counterpart AB5, respectively. The in vivo bioassay confirmed much better preservative effect of D8 than that of Carbendazim. The chiral oxazinone variant D10 possessed prominent antibacterial activity, with MIC values of 8 mg/L against both Bacillus subtilis and Ralstonia solanacearum, showing advantages over the positive control streptomycin sulfate.
Synthesis and structure-activity relationships for cytotoxicity and apoptosis-inducing activity of (+)-halichonine B
Hayakawa, Ichiro,Nakamura, Tomomi,Ohno, Osamu,Suenaga, Kiyotake,Kigoshi, Hideo
, p. 9969 - 9976 (2015/10/12)
Halichonine B is a sesquiterpene alkaloid isolated from the marine sponge Halichondria okadai Kadota. Halichonine B has exhibited cytotoxicity against mammalian cancer cells and induced apoptosis in the human leukemia cell line HL60. Here we established a practical route for the synthesis of halichonine B and its analogues, and we evaluated their biological activities. It was revealed that the secondary amino groups in the side chain portion are important for the strong cytotoxicity of halichonine B and that the N11-prenyl group is unimportant. Halichonine B and its analogues were also observed to induce apoptosis in HL60 cells.
