Scilla scilloides

Ganoderic acids, for example S, are found in the above- and under-ground parts of the fungus Ganoderma lucidum which is used in traditional Chinese and Japanese medicine for tonic preparations to increase vitality. 27-Norlanostanes, for example (-)-17,23-epoxy-28-hydroxy-27-norlanost-8-ene-3,24-dione, are isolated from the bulbs of some Mediterranean grape hyacinths such as Muscari comosum and Scilla scilloides (Liliaceae). 

Another source of homoisoflavanones is Scilla scilloides Druce. Kouno et al. (44) have described the isolation and identification of 3,9-dihydro-eucomnalin along with the structurally related compounds scillascillin and 2-hydroxy-7-0-methylscillascillin. The new structural feature of these substances is a 3-spirocyclobutene ring system. The name scil-lascillins was adopted for this group of compounds. 

The co-occurrence of the 3-benzylchroman-4-one derivative 3,9-dihydroeucomnalin (13), scillascillin (19) and 2-hydroxy-7-0-methyl-scillascillin (20) in Scilla scilloides opened a discussion on their possible biogenetic relationship (19). Starting from the 3,3 -dioxy compound (98), cyclization to the spirocyclic intermediate (99) and formation of the scillascillin skeleton (101) may easily take place. In a similar manner... 

Kouno, I., T. Komori, and T. Kawasaki Zur Struktur der neuen Typen Homoisoflavanone aus Bulben von Scilla scilloides Druce. Tetrahedron Letters 1973, 4569. 

Fig. 3. Two-dimensional chromatograms of bulb wax phenolics of (A) Chionodoxa gigantea, (B) Ch. tmoli, (C) Scilla bifolia, (D) Ch. luciliae, (E) Ch. sardensis, and (F) S. scilloides (see text)...

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