Two Glycosides and Other Constituents from Anemone tomentosa Roots

Two new natural products, i.e., 1‐O,2‐O‐[(1S,2S)‐1‐(3‐acetyl‐2,4,6‐trihydroxyphenyl)‐3‐hydroxypropane‐1,3‐diyl]‐β‐D ‐glucopyranose (=tomentoside I; 1 ) and (3β)‐3‐(acetyloxy)ferruginol 12‐[6‐O‐(4‐hydroxy‐3,5‐dimethoxybenzoyl)‐β‐D ‐glucopyranoside] (=tomentoside II; 2 ), were isolated from the EtOH extract of the root of Anemone tomentosa, together with five known compounds. Their structures were characterized by means of spectroscopic methods, especially by ¹H‐, ¹³C‐, and 2D‐NMR and HR‐MS, as well as by chemical methods and comparison with literature data.     

(±)-16-羟基-6,7-脱氢铁锈醇甲醚及其类似物的合成

采用AC→ABC的合成策略,以α-环柠檬醛为A环起始原料,通过与C环化合物8缩合、选择性还原及分子内环合得到关键中间体11,再经过官能团修饰和转换,合成了16-羟基-6,7-脱氢铁锈醇甲醚及其3个类似物.     

Lateral lithiation in terpenes: synthesis of (+)-ferruginol and (+)-sugiol

This paper describes the use of (−)-sclareol in the synthesis of the tricyclic diterpenes of abietane skeleton, such as (+)-ferruginol and (+)-sugiol, using as key step the lateral lithiation of a dinorditerpene derivative.     

Short syntheses of (+)-ferruginol from (+)-dehydroabietylamine

Short syntheses of bioactive (+)-ferruginol in five or six synthetic steps starting from commercially available (+)-dehydroabietylamine are described. The oxygenated function at C12 was introduced via a Friedel-Crafts acylation of N-phthaloyldehydroabietylamine followed by Baeyer-Villiger oxidation. Then, overall deprotection of functional groups, reductive deamination or biomimetic oxidative deamination, and final Wolff-Kishner reduction provided (+)-ferruginol in 21 and 23% overall yields, respectively.     

Application of ToF-SIMS to the study on heartwood formation in Cryptomeria japonica trees

Influence of gold- and carbon-coating on ToF-SIMS analysis of Cryptomeria japonica (Sugi) wood has been investigated to apply the samples after observing water distribution by cryo-scanning electron microscopy (cryo-SEM) or analyzing distribution of metal elements by SEM with energy dispersive X-ray spectrometer (SEM/EDX) to ToF-SIMS analysis to study the mechanism of heartwood formation of woody plants. The intensities of peaks at the m/z 285 ion in positive mode and the m/z 283 ion in negative mode from gold- and carbon-coated samples were compared with from those of non-coated samples. Those peaks were apparently attributable to ferruginol, a typical heartwood compounds in Sugi tree. From both gold- and non-coated samples, positive m/z 285 ions were generated. On the other hand, in negative mode, the intensity of m/z 283 ion was decreased after coating with gold. From carbon-coated samples, intensities of both positive m/z 285 ion and negative m/z 283 ion were decreased. These results suggest that the samples coated with gold for cryo-SEM could be applied to ToF-SIMS analysis directly to investigate the relation between water distribution and distribution of heartwood substances in heartwood-forming Sugi trees. However, non-coated samples should be used for SEM/EDX before analyzing by ToF-SIMS.