专利号:US-2018105838-A1 优先权日:2015-03-11 标 题:Process for de novo microbial synthesis of terpenes 发明人:SCHRADER JENS; BUCHHAUPT MARKUS; SONNTAG FRANK; KRONER CORA; BRÜSER HEIKE; Schröder Hartwig; PELZER RALF 权利人:BASF SE 摘要:The invention relates to microbial terpene production. Known methods for microbial production of terpenes are mostly based on the direct conversion of sugars. Therefore alternative substrates, in particular alternative carbon sources, for use in microbial terpene production were desirable. The invention relates to a methylotrophic bacterium containing recombinant DNA coding for at least one polypeptide with enzymatic activity for heterologous expression in said bacterium, wherein said at least one polypeptide with enzymatic activity is selected from the group consisting an enzyme of a heterologous mevalonate pathway, a heterologous terpene synthase and optionally a heterologous synthase of a prenyl diphosphate precursor. The invention further relates in particular to a method for de novo microbial synthesis of sesquiterpenes or diterpenes from methanol and/or ethanol.
专利号:WO-2024107075-A1 优先权日:2022-11-14 标 题 :Hybrid compounds of sclareol and doxorubicin, their synthesis and application 发明人:PESIC MILICA; OPSENICA IGOR; KOSTIC ANA; TERZIC-JOVANOVIC NATASA 权利人:INSTITUTE FOR BIOLOGICAL RESEARCH SINISA STANKOVIC NATIONAL INSTITUTE OF THE REPUBLIC OF SERBIA UNIV 摘要:The invention represents new hybrid compounds of two natural products sclareol and doxorubicin in the form of their conjugates. These compounds are in the form of conjugates, where doxorubicin and sclareol are covalently linked by a linker in a 1:1 molar ratio. The hybrids have shown to possess anticancer properties and are effective in treating resistant cancer cells that have P-glycoprotein membrane transporter, responsible for resistance to doxorubicin. The hybrids have been tested on different types of cell lines, including human glioblastoma, non-small cell lung carcinoma, and colorectal carcinoma. Also, a method for their preparation and their use in medical products or pharmaceutical preparations has been determined. The results of the study include the cytotoxic activity of single, combined, and conjugated compounds in pairs of sensitive and resistant cancer cells, with and without P-glycoprotein expression. The selectivity towards cancer cells was determined by comparing with commercially available normal human lung fibroblast cells. The study also investigated the nanoparticle nature of hybrid compounds, their intracellular localization and toxicity in vivo.
专利号:US-12163174-B1 优先权日:2023-05-26 标题 :Method for producing sclareol by fermentation of cigar tobacco flower buds 发明人:YU JUN; YANG CHUNLEI; WANG ZHI; CHEN XIONG; LI ZONGPING; YANG JINPENG; LI HAO; YAO LAN; RAO XIONGFEI; PENG HAO; XU SHIPING; WANG WENMING 权利人:TOBACCO RES INSTITUTE OF HUBEI PROVINCE; UNIV HUBEI TECHNOLOGY 摘要:A method for producing sclareol by fermentation of cigar tobacco flower buds is provided, including: mixing cigar tobacco flower buds with deionized water, sterilizing and adding edible yeast, then fermenting at 25-30° C. and 100-300 rpm/min for 24-30 h. This method uses cigar tobacco flower buds as the sole raw material, without adding additional nutrients, and only ferments tobacco flower buds with edible yeast to synthesize sclareol. Meanwhile, this method has extremely high synthesis efficiency.
专利号:US-5473085-A 优先权日:1994-07-22 标题:Production of (-)dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b] furan 发明人:BARTON DEREK H R; TAYLOR DENNIS K; TSE CHI-LAM 权利人:QUEST INT 摘要:Preparation of a methyl ketone intermediate useful in the synthesis of (-)-dodecahydro-3a,6,6, 9a-tetramethyl-naphtho(2,1-b) furan by subjecting (-)-sclareol to ozonolysis in the presence of iodine or iodine-containing compound. The intermediate can be converted to (-)-dodecahydro-3a,6,6,9a-tetramethyl-naphtho(2,1-b) furan by Baeyer-Villiger oxidation followed by reduction of the resulting product in the presence of a Lewis acid.
专利号:US-5463089-A 优先权日:1994-07-22 标 题 :Preparation of ambrox 发明人:BARTON DEREK H R; PAREKH SHYAMAL I; TAYLOR DENNIS K; TSE CHI-LAM 权利人:QUEST INT 摘要:Synthesis of (-)-dodecahydro-3a,6,6,9a-tetramethyl-naphtho(2,1-b)furan from sclareol in a three-stage process.
专利号:US-2006223883-A1 优先权日:2005-04-02 标题 :Novel hydroxylated enantiomers of (-) 3a,6,6,9a-tetramethylperhydronaphtho[2,1-b]furan as perfuming agents derived from a fungal fermentation process. 发明人:RAHMAN ATTAUR; CHOUDHARY MOHAMMAD I; MUSHARRAF SYED G 权利人:RAHMAN ATTAUR; CHOUDHARY MOHAMMAD I; MUSHARRAF SYED G 摘要:(−) 3a,6,6,9a-tetramethylperhydronaphtho[2,1-b]furan (ambrox) is a strong aromatic compound used widely in a variety of perfumery applications and is highly prized for its musky odor. We report novel polar metabolites of (−)3a,6,6,9a-tetramethylperhydronaphtho[2,1-b]furan prepared by a novel process of microbial fermentation using a fungi, Fusarium lini , of unique structures that would be difficult to predict opening up the possibilities of their chemical synthesis. The polar metabolites discovered have stronger aromatic characteristics and offer a new highly prized odiferous characteristic quite different from that of the parent compound and thus can be used in the preparation of perfumes, odor-masking and other odor-management applications.
1: Zhong Y, Huang Y, Santoso MB, Wu LD. Sclareol exerts anti-osteoarthritic activities in interleukin-1β-induced rabbit chondrocytes and a rabbit osteoarthritis model. Int J Clin Exp Pathol. 2015 Mar 1;8(3):2365-74. eCollection 2015. 2: Fujimoto T, Mizukubo T, Abe H, Seo S. Sclareol induces plant resistance to root-knot nematode partially through ethylene-dependent enhancement of lignin accumulation. Mol Plant Microbe Interact. 2015 Apr;28(4):398-407. doi: 10.1094/MPMI-10-14-0320-R. doi: 10.3892/mmr.2015.3325. Epub 2015 Feb 10. doi: 10.1159/000445647. Epub 2016 Jul 11. doi: 10.1007/s10126-015-9610-7. Epub 2015 Jan 30. doi: IJIv10i1A2. doi: 10.1111/jocd.12239. Epub 2016 Jul 28. doi: 10.1186/s12934-015-0246-0. 9: Shakeel-u-Rehman, Rah B, Lone SH, Rasool RU, Farooq S, Nayak D, Chikan NA, Chakraborty S, Behl A, Mondhe DM, Goswami A, Bhat KA. Design and Synthesis of Antitumor Heck-Coupled Sclareol Analogues: Modulation of BH3 Family Members by SS-12 in Autophagy and Apoptotic Cell Death. J Med Chem. 2015 Apr 23;58(8):3432-44. doi: 10.1021/jm501942m. Epub 2015 Apr 9. Chinese. doi: 10.1016/j.bmcl.2015.05.013. Epub 2015 May 14. Chinese. doi: 10.1021/ja307404u. Epub 2012 Nov 7. doi: 10.1016/j.saa.2014.11.049. Epub 2014 Nov 29. doi: 10.1186/1471-2229-12-119.
合成参考文献
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