Hinokinin

ToF-SIMS spectra were acquired in positive ion mode and four different extractives were identified. The two main peaks were assigned to hinokinin (m/z 353) and hinokir-esinol (m/z 252). Lower peaks at m/z 299 and m/z 302 were assigned to hinokione and hinokiol, respectively. These identifications were confirmed by the study of the pure molecules. 

As ToF-SIMS also allows the mapping of the chemical species inside the sample, distributions of the different extractives in the cross-section of the wood are evaluated. They show clearly that hinokinin is predominantly localized in parenchyma cells other extractives are distributed randomly in both parenchyma and tracheid cells (Figure 15.8c). This could be very helpful in understanding the heartwood formation mechanism. 

The main lignan in flaxseed is SDG (Figure 2). Also present are a number of other lignans, that is, matairesinol (MAT), lariciresinol, hinokinin,... 

Honda T, Kimura N et al (1994) Chiral synthesis of lignan lactones, (—)-hinokinin, (—)-deoxypodorhizone, (—)-isohibalactone and (—)-savinin by means of enantioselective deprotonation strategy. J Chem Soc Perkin Trans 1 1043-1046... 

The formation of the endocyclic double bonds of unsaturated lactones has been accomplished via the rDA reaction. The preparation of 2-alkyl-2-butenolactones, such as (179), by a method that incorporates the rDA reaction as a key step has been a q>lied to the synthesis of butyrolactone lignans such as ( >-hinokinin (180) as shown in equation (80). An extensive study of the preparation of substituted 2-bute-nolides (183) has been reported. The mono-, di- and tri-alkyl bicyclobutenolides are prepared by reacting adducts (181) with Grignard reagents or with LDA followed by alkyl halides. Alkylated adducts (182) were then either directly distilled under vacuum or heated in a sealed tube to give the alkylated 2-bute-nolides (183) (equation 81). " ... 

Further general route to 2-alkyl-2-butenolactones via the retro Diels-Alder reaction was developed. Fig, 5, [23]. Hydrolysis of a known lactone (15), subsequent esterification with diazomethane, and treatment with dihydropyran afforded a stereoisomeric mixture of pyranyl ether. Alkylation of the pyranyl ether with various alkyl halide yielded alkylated products (16). The retro Diels-Alder reaction of 16 was performed by heating at 200-280 C in a sealed tube to give 2-alkyl-2-butenolactones (17). The utility of the butenolactones was demonstrated by the synthesis of hinokinin (18) and dehydrolappaol A dimethyl ether (19). Similarly rather mild, simple synthesis of a-methylene-y-alkylbutyrolactones was deviced using dimethylfulvene as a protective group for the double bond, Fig. 6. [24], The... 

Deoxypodophyllotoxin (anthricin), (-)-deoxypodorhizone, nemerosin, morelensin, and (-)-hinokinin from Anthriscus sylvestris (Umbelliferae) showed antiproliferative activities in vitro against MK-1, HeLa, and... 

In their review of lignans MacRae and Towers [9] cited the activity of kobusin and sesamin against silkworm larvae, sesamin and sesamolin against juvenile hormone activity in the milkweed bug, and podophyllotoxins against insect larval growth. On the other hand, sesamin, asarinin, savinin and hinokinin enhanced the toxicity of a wide variety of insecticides. 

A third approach to asymmetric synthesis involving oxidative dimerisation of dihydrocinnamic acid derivatives is shown in scheme 13 ( f. scheme 7) [64,65]. By choosing an appropriate chiral auxiliary, either (-)- or (+)-hinokinin, for example, can be prepared. In either case removal of the chiral auxiliary leads to an anhydride having C2 symmetry which can be reduced to the lactone. 

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