Polyacetylene compounds from roots

The acetylene compounds - Panaxynol and falcarindiol, isolated from the roots of Saposhnikovia divaricata (Turcz.) Schischk. (Umbelliferae), selectively inhibited 5-LOX (ICso = 2 pM), leukocyte-type 12-LOX (IC50 = 1 pM), platelet-type 12-LOX (IC50 = 67 pM), and 15-LOX (IC50 = 4 pM). The same compounds had only marginal effects on COX activities with IC50 > 100 pM [126]. Bidens campylotheca Schultz Bip. ssp. campylotheca (Compositae) is a Hawaiian folk medicine for throat, stomach and asthmatic disorders. The polyacetylenes isolated from the aerial parts of the plants, such... 

The roots of Saposhnikovia divaricata ("Bou-hu" in Japan and "Fang-Feng" in China) have been traditionally used as an antiphlogistic, an antipyretic and an analgesic in China and Japan. We isolated three polyacetylene compounds, i.e., falcarindiol, panaxynol and (8E)-heptadeca-l,8-dien-4,6-diyn-3,10-diol "Fig. (32)", from Saposhnikoviae Radix. As shown in "Fig. (33)", these polyacetylene compounds inhibited the formation of cyclooxygenase products HHT and TXB2dose-dependently in human platelets. 

The discovery of junipal focused the attention of Sorensen, who had been investigating the occurrence of polyacetylenes in Com-positae, on the possibility that these acetylenes were accompanied by thiophenes. From Coreopsis grandiflora Hogg ex sweet, 2-phenyl 5-(1-propynyl) thiophene (240) was isolated and its structure confirmed by synthesis of the tetrahydro compound, 2-phenyl-5-n-propyl-thiophene. From the root of tansy, the cis and trans isomers of methyl 5-(l-propynyl)-2-thienylacrylate (241) have been isolated. The total synthesis of trans (241) was achieved by reacting junipal with methylcarbethoxy triphenylphosphonium bromide (Wittig reaction) Several monosubstituted thiophenes, (242), (243), and... 

The root of carrot Daucus carota) is eaten raw or cooked. The characteristic aroma and flavour of carrots are mainly due to volatile compounds, although non-volatile polyacetylenes and isocoumarins contribute significantly to the bitterness of carrots [1,2]. More than 90 volatile compounds have been identified from carrots (Table 7.9) [207-215]. The carrot volatiles consist mainly of terpenoids in terms of numbers and amounts and include monoterpenes, sesquiterpenes and irregular terpenes. Monoterpenes and sesquiterpenes account... 

Japanese workers have isolated the known polyacetylenes artemisia ketone (28) and (29) from the root of the Japanese mugwort Artemisia princeps Pamp). The authors concluded that the Japanese plant was probably a different species from the European plant, Artemisia vulgaris L., since the spiro-compound (29) has not been found in the latter. 

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