Prenylated acetophenones from Melicope obscura and Melicope obtusifolia ssp. obtusifolia var. arborea and their distribution in Rutaceae

Four prenylated acetophenones 2,6-dihydroxy-4-geranyloxyacetophenone (1), 4-geranyloxy-2,6,β-trihydroxyacetophenone (2), 2,6-dihydroxy-4-geranyloxy-3-prenylacetophenone (3), and 4-geranyloxy-3-prenyl-2,6,β-trihydroxyacetophenone (4) have for the first time been isolated from Melicope obscura (1 and 2) and Melicope obtusifolia ssp. obtusifolia var. arborea (3 and 4). The distribution of prenylated acetophenones in Rutaceae is reviewed and the results, including the new records, indicate that prenylated acetophenones are valuable as chemotaxonomic markers for the subfamily Rutoideae, tribe Xanthoxyleae sensu Engler.     

Methylenedioxy- and methoxyflavones from Melicope coodeana syn. Euodia simplex

Three new natural products, 3,8-dimethoxy-5,7-dihydroxy-3′,4′-methylenedioxyflavone, 3,6,8-trimethoxy-5,7-dihydroxy-3′,4′-methylenedioxyflavone and 3,6,8,3′,4′-pentamethoxy-5,7-dihydroxyflavone were isolated from Melicope coodeana syn. Euodia simplex (Rutaceae) along with 3,6,3′-trimethoxy-5,7,4′-trihydroxyflavone and 3,3′-dimethoxy-5,7,4′-trihydroxyflavone. The structural assignments are based on ¹H and ¹³C NMR data, including discussion of the chemical shifts of C-2 in 3,5-dihydroxy- and 3-methoxy-5-hydroxyflavones. The presence of highly methoxylated and methylenedioxyflavones is characteristic of the genus Melicope, and the present findings support the recent transfer of Euodia simplex to Melicope.     

Euodionosides A-G: megastigmane glucosides from leaves of Euodia meliaefolia

From a 1-BuOH-soluble fraction of the MeOH extract of leaves of Euodia meliaefolia, collected in Okinawa, seven megastigmane glucosides, named euodionosides A-G, were isolated together with three known megastgmane glucosides, and two aliphatic and three phenolic compounds. Their structures were elucidated through a combination of spectroscopic analyses and application of the modified Mosher's method.     

楝叶吴茱萸和臭辣树种子油中十八碳链不饱和脂肪酸成分的分析鉴定

用＂远端羧基的化学修饰＂、色谱－质谱方法分离鉴定了楝叶吴茱萸和臭辣树种子油中的十八碳不饱和脂肪酸,含常见的亚油酸和不常见的１０－十八碳烯酸,以及在植物中首次发现的９,１３,１５－十八碳三烯酸．楝叶吴株萸和臭辣树种子油的脂肪酸组成（％）分别为：棕榈酸１０．１,１０．７;硬脂酸１．０,１．９;棕榈油酸２１．２,２０．７;１０－十八碳烯酸２８．５,３１．７;亚油酸２４．２,１７．５;９,１３,１５－十八碳三烯酸１５．０,１４．９．     

Contribution of molecular cladistics to the taxonomy of Rutaceae in China*

The treatment of Rutaceae in the Chinese flora chose to follow Engler in recognizing Rutoideae and Toddalioideae as two separate subfamilies. Morphological and chemical comparisons, however, suggested grouping those two subfamilies in one subfamily, Rutoideae. This move has received support from molecular phylogenetic analyses, which also showed that the Chinese taxa in Euodia should be placed in Tetradium and Melicope following Hartley. Investigations into the chemistry and molecular phylogeny of Murraya also indicated that the species in the section Bergera without yuehchukene should be removed from Murraya. These findings clearly show the value of molecular cladistics to the taxonomy of Rutaceae in China and also directions for further investigations.     

Methylenedioxy- and methoxyflavones from Melicope coodeana syn. Euodia simplex

Three new natural products, 3,8-dimethoxy-5,7-dihydroxy-3′,4′-methylenedioxyflavone, 3,6,8-trimethoxy-5,7-dihydroxy-3′,4′-methylenedioxyflavone and 3,6,8,3′,4′-pentamethoxy-5,7-dihydroxyflavone were isolated from Melicope coodeana syn. Euodia simplex (Rutaceae) along with 3,6,3′-trimethoxy-5,7,4′-trihydroxyflavone and 3,3′-dimethoxy-5,7,4′-trihydroxyflavone. The structural assignments are based on ¹H and ¹³C NMR data, including discussion of the chemical shifts of C-2 in 3,5-dihydroxy- and 3-methoxy-5-hydroxyflavones. The presence of highly methoxylated and methylenedioxyflavones is characteristic of the genus Melicope, and the present findings support the recent transfer of Euodia simplex to Melicope.     

Contribution of molecular cladistics to the taxonomy of Rutaceae in China

The treatment of Rutaceae in the Chinese flora chose to follow Engler in recognizing Rutoideae and Toddalioideae as two separate subfamilies. Morphological and chemical comparisons, however, suggested group-ing those two subfamilies in one subfamily, Rutoideae. This move has received support from molecular phyloge-netic analyses, which also showed that the Chinese taxa in Euodia should be placed in Tetradium and Melicope following Hartley. Investigations into the chemistry and molecular phylogeny of Murraya also indicated that the species in the section Bergera without yuehchukene should be removed from Murraya. These findings clearly show the value of molecular cladistics to the taxonomy of Rutaceae in China and also directions for further inves-tigations.