Catalpa ovata

Naphthoquinones Catalpa ovata SiOj Hx - AcOEt UV 254, 366 nm Identification 61 0 q... 

Cc r 0 Wood and tissue cultures of Catalpa ovata (Bignoniaceae) [76] [77],... 

Wood and cell cultures of Catalpa ovata [88-89], wood of Haplophragma adenophyllum [90], Tabebuia guayacan [91] T. pentaphylla [83], Zeyhera tuberculosa [92] Roots of Ekmanianthe longiflora (all Bignoniaceae) [78], Biological Effect inhibition of topoisomerase II [16]. 

OH Wood and cell cultures of Catalpa ovata [88-89] Zeyhera tuberculosa [92]. 

Helianthus annuus (Asteraceae), Catalpa ovata (Bignoniaceae), Arachis hypogaea (Fabaceae), Triticum aestivum (Poaceae), Cimicifuga racemosa, C. spp. (Ranunculaceae) [rhizome], Tamarix aphylla (Tamaricaceae) [leaf]... 

Catalposide (= Catalpin) Catalpa ovata (Bignoniaceae), Veronica Bitter [diuretic, laxativej... 

Radermachera sinica [104] wood and tissue cultures of Catalpa ovata [105-106] Cresenci a cuye/e [107-108], roots of Ekmanianthe longiflora [78] ( all Bignoniaceae), Biological effect antitumoral [78]... 

Wood of Radermachera sinica [104], tissue culture Catalpa ovata [105-106],... 

When [l-carboxy- C]o-succinyl benzoate is administered to plants of Catalpa ovata (Bignoniaceae), it is incorporated into a-lapachones (such as 45), catalponol (46), and catalpalactone (47). Examination of the ratio in catalponol (46) after administration of [l-carboxy- C,2 - H2]o-succinylbenzoate reveals that the two protons at the 2 -posi-tion are both retained in the 3-position of catalponol (Fig. 6.9). Thus, prenylation occurs at the 2-position and does not involve an aromatic compound such as 1,4-dihydroxy-2-naphthoic acid (DHNA) (40) (Inouye and Leistner, 1988). 2-Carboxy-4-oxotetralone (COT) (43) or 2-carboxy-4-hy-droxy-l-tetralone (48) are possible acceptors for the prenyl unit. When 2-carboxy-4-hydroxy-l-tetralone (48), or its methyl ester, was introduced into the plant, the prenyl derivatives of 2-carboxy-4-oxotetralone (COT) (43) and 2-car-boxy-4-hydroxy-l-tetralone (50) were isolated as intermediates (Inouye and Leistner, 1988). 

Fig. 6.9. Biosynthesis of niodified naphthoquinones in Catalpa ovata (modified from Inouye and Leistner, 1988 used with pennission of the copyright owner, John Wiley Sons, Ltd., Chichester).

Ueda, S., K. Inoue, Y. Shiobara, I. Kimura, and H. Inouye Quinones and Related Compounds in Higher Plants. X. Naphtoquinone Derivatives of the Callus Culture of Catalpa ovata. Planta medica 40,168 (1980). 

Vitamin K with only one prenyl unit (XVI) has been isolated from callus tissue of Catalpa ovata. This naphthoquinone is associated with l-hydroxy-2-methylanthraqui-none (XVII) and o succinylbenzoic acid (II) is a precursor of these compounds. During their biosynthesis 2-prenyl-carboxyoxotetralone (XVIII) and catalponone (XIX) are formed. This was established by trapping labelled XVIII and XIX after administration of radioactive o-succinyl-benzoic acid (II) to ovata tissue cultures. The chirality of XVIII and XIX was shown to be 2S (XVIII) and 2R (XIX) respectively. Formation of catalponone (XIX) does not proceed through DHNA (V). The biosynthesis of anthra-quinone in the tissue culture of iC. ovata may therefore be different from the cultures of Rubia, Morinda and Galium in that carboxyoxotetralone (XX) is prenylated instead of... 

Quinones and related compounds in higher plants. Part 11. Role of 2-carboxy-2,3-dihydro-1,4-naphthoquinone and 2-carboxy-2-(3-methyl-but-2-eny1)-2,3-dihydro-1,4-naphthoquinone in the biosynthesis of naphthoquinone congeners of Catalpa ovata callus tissue. J. Chem. Soc., Perkin Trans. I, 1246-1258. 

Inouye H, Okuda T, Hayashi T 1971 Naphtochinonderivate aus Catalpa ovata G. Don. Tetrahedron Lett 39 3615-3618... 

Other interesting phenolic wood constituents of napthoquinone type are the prenylated derivatives (42) in the durable wood of Catalpa ovata (Bignoniaceae) (64). Sesquiterpenes of naphthalene type (cadalene type e.g. 43), which occur in... 

Isol. from Cimicifuga racemosa, Catalpa ovata and other plants. Plates. Mp 233-234°. 

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