Fabiana imbricata

N. K. Richtmyer, The isolation of D-mawio-heptulose, perseitol, D-glycero-D-manno-octulose, and other compounds from Pichi tops (Fabiana imbricata Ruiz Pav.), Carbohydr. Res., 12 (1970) 233-239. 

Present in loaves of Fabiana imbricata, Baiz. et Pav. Needles -f- 2HjO from H[jO. M.p. 226-8°, Sol. hot HjO. Spar. sol. cold org. solvents. Hyd. —> glucose scopoletin. 

Occurs widely in the plant world, for example, the root of Gelsemium sempervirens, Atropa belladonna. Convolvulus scammonia, Ipomaea orizabensis, Prunus serotina, Fabiana imbricata and also Diospyros spp., Peucedanum spp., Heracleum spp., Skimmea spp. Also occurs in the Chinese crude drug Toki(from Angelica acutiloba). Needles or prisms (EtOH). Mp 204°. Reduces Fehling s and Tollen s reagents. 

Isol. from leaves of Fabiana imbricata. Needles -I- 2H2O (H2O). Mp 226-228°. 

A volatile tetrahydroquinoline alkaloid named fabianine (Fig. 5.1) was identified from the aerial part of Fabiana imbricata Ruiz Pav. (Edwards and Elmore 1962). This base is a congener of bicychc, cadinene/norcadinene type sesquiterpenes (see Sect. 7.3.1). Fabianine seems to share a common precursor with a monocyclic (A-free) diketonorcadinene type metabolite. Thus, it may be assumed that the structure of fabianine is characterized by a sesquiterpenoid skeleton (Schmeda-Hirschmann and Papastergiou 1994). 

Schijlen EGWM, Ric de Vos CH, van Tunen AJ, Bovy AG (2004) Modification of flavonoid biosynthesis in crop plants. Phytochemistry 65 2631-2648 Schmeda-Hirschmann G, Jordan M, Gerth A, Wilken D, Hormazabal E, Tapia AA (2004) Secondary metabolite content in Fabiana imbricata plants and in vitro cultures. Z Naturforsch 59c 48-54... 

Schmeda-Hirschmann G, Papastergiou F (1994) Sesquiterpenes from Fabiana imbricata. Phytochemistry 36 1439-1442... 

Occurs naturally as glucosides. Isol. free from Picea glehnii, Apocynum cannabinum, Fabiana imbricata and other plants. Needles (EtOH aq. or Et20). Mp 109°. Bpj 148°. pK 8.05 (25°). 

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