Solidago altissima L.から単離されたアセチレン類およびテルペン類の特性

[Synopsis] Four acetylenes and three terpenoids were isolated from Solidago altissima L. and characterized by MS, \u27H-NMR and ^C-NMR spectroscopy as methyl (Z)-decaene-4,6,8-triynoate (Zdehydromatricaria ester, 1), methyl 10-[(Z)-2-methyl-2-butenoyloxy]-(2Z,84-2,8-decadiene-4,6-diyoate (2), (4Z-2,4-decadiene-6,8-diyn-4-olide (Z-dehydromatricaria lactone, 3), (4E)-2,4-decadiene-6,8-diyn-4-olide (E-dehydromatricaria lactone, 4), 13E,7 α-acetoxyl kolavenic acid (solidagonic acid, 5), kolavenol (6), and D:C-friedours-7-en-3 β-ol (ilexol, 7). The polyacetylenes could be easily detected as yellowish brown spots on TLC plate following irradiation with blue black light for two to three minutes. The Z and E isomers of dehydromatricaria lactones were easily differentiated based on differences in melting points and chemical shifts of ^1H- and ^C-NMR spectroscopy. Bioassay of these compounds on the germination of lettuce seeds showed that compounds 1, 2, 3, 4, and 5 exhibited growth inhibitory activity, whereas compound 7 did not exhibit the activity. This study presents the first isolation of (E)-dehydromatricaria lactone from Solidago altissima L. in nature. （摘要） Solidago altissima L..から単離した4種のアセチレンおよび3種のテルペン、methyl (z)-decaene-4,6,8-triynoate (Z-dehydromatricaria ester, 1), methyl 10-[(Z)-2-methy 1-2-butenoyloxy]-(2Z,8Z)-2,8-decadiene-4,6-diyoate (2), (4Z)-2,4-decadiene-6,8-diyn-4-olide (Z-dehydromatricaria lactone, 3), (4E)-2,4-decadiene-6,8-diyn-4-olide (E-dehydromatricaria lactone, 4) 13E,7 α-acetoxyl kolavenic acid (solidagonic acid, 5) kolavenol (6), D:C-friedours-7-en-3β-ol (ilexol, 7)について発芽に対する影響をレタスを用いて検討した。その結果、化合物 1,2,3,4 および5は生長阻害作用を示し、化合物7は活性を示さなかった。ポリアセチレンは、TLC上で2, 3分ブルーブラックライトの照射によって黄茶色のスポットとして、容易に確認できた。 Dehydromatricaria lactones のZ体およびE体は、融点の違い、また、^1H-および^C-NMRのケミカルシフトの違いによって、容易に確認できた。なお、単離した成分のうち、（E)-dehydromatricaria lactone (4)は天然物としてSolidago altissima L. から初めて見出した成分である