Phytochemistry of the genus Skimmia (Rutaceae) Author Epifano, Francesco Dipartimento di Farmacia, Università ‘‘ G. D’Annunzio’ ’ Chieti-Pescara, Via dei Vestini 31, 66013 Chieti Scalo, CH, Italy Author Fiorito, Serena Author Genovese, Salvatore Author Granica, Sebastian Author Vitalini, Sara Author Zidorn, Christian text Phytochemistry 2015 2015-07-31 115 1 27 43 http://dx.doi.org/10.1016/j.phytochem.2015.02.014 journal article 285349 10.1016/j.phytochem.2015.02.014 d30e1c4c-6a0f-4e42-97ec-8f9abb4e26ea 1873-3700 10486867 3.3. S. x foremanii S x foremanii , commonly known as ‘‘Japanese skimmia’’ is an up to 1.5 m high evergreen shrub, featuring stellate shaped white flowers arranged in a cyme, ovate leaves, and red fruits. S. x foremanii is a hybrid between S. japonica and S. reevesiana ( Weinstein and Craig, 1971 ) . Weinstein and Craig (1971) investigated the apolar extract obtained from leaves of S. x foremanii and isolated one alkaloid, dictamnine 12 , two coumarins, isoimperatorin 47 and (+)- oxypeucedanin 48 , and two triterpenes, skimmiol (syn. taraxerol) 80 and skimmione (syn. taraxerone) 81 . Compared to other Skimmia taxa the number of secondary metabolites reported from S. x foremanii is very limited and the taxon warrants more attention in the next future both from a phytochemical and pharmacological point of view. Future studies should be focused on both the hybrid HO O O

compound name		R1	R2	R3	R	ε	MW
45	arnocoumarin	H	H	-	-	226
46	bergapten	H	OCH3	H	-	-	202
47	isoimperatorin	H	H	-	-	270
-	-
48	(+)-oxypeucedanin	H	H	286
49	(+)-oxypeucedanin hydrate	H	H	-	-	304
50	(+)-oxypeucedanin methanolate	H	3	H	-	-	318
-	-
51	(+)-saxalin	H	H	323
52	mermesin	H	H	-	saturated bond	246
53	nodakenetin	H	H	-	saturated bond	246
54	isorutarin glucoside 6’-feruloyl ester	OH	H	3	saturated bond	600
55	isorutarin glucoside 6’-sinaponyl ester	OH	H	3	saturated bond	630
3
56	rutarenin	OH	H	-	saturated bond	262
57	xanthotoxin	OCH3	H	H	-	-	202
58	imperatorin	H	H	-	-	270
-	-
59	isogospherol	H	H	286
-	-
60	(+)-heraclenin	H	H	286
-	-
61	(+)-heraclenol	H	H	304
62	isopimpinellin	OCH3	OCH3	H	-	-	246
63	phellopterin	OCH3	H	-	-	300

Fig. 3. Chemical structures and molecular weights of linear furocoumarins – compounds 45–63 . 64 , columbianectin, MW 246 65 , seselin, MW 220 and both its parental species. It will be of particular interest to elucidate whether the secondary metabolite profile of the hybrid taxon contains additive sets of compounds from its parents (i.e. the metabolites found in S. japonica plus the ones found in S. reevesiana ) or only the intersecting set (i.e. only compounds found in both species) and whether this pattern is uniform or diverging for different compound classes (phenolic, coumarins, alkaloids, etc.). Another aspect to be studied in future investigations is whether crosses of male S. japonica and female S. reveesiana plants result in phytochemically identical plants as compared to crosses of female S. japonica and male S. reveesiana plants. Skimmia being a dioecious genus, a comparison of male and female descendants of such crossing experiments is obviously of interest, too.