Valerianine, a Tertiary Monoterpene Alkaloid from Valerian

Abstract

Dedicated to Professor Kurt Mothes on the occasion of his 70th birthdayAlthough it has long been known that valerian (Valerianu officinalis L.), which is used medicinally because of its sedative action, contains alkaloids [21, it is only recently that two quaternary pyridine bases have been isolated from it and their structures determined (31. We now report a new, sedative, tertiary, rnonoterpene alkaloid (8) from Vaferiana officinolis and its total synthesis, which also opens a simple route t o a group of related alkaloids from Actinidiaceae and Bignoniaceae [41.H3c? (8) as it is for numerous monoterpene, isoquinoline, and indole alkaloids [lo].The synthesis of (-)-valerianine is also the first preparation of a derivative of (-)-tecostidine ( 7 ) 1111. Actinidine (6) can also be simply prepared in this way 1131.

Biomedically relevant chemical constituents of Valeriana officinalis

“…Alkaloids are present in amounts of 0.01-0.05% and there are also terpene alkaloids present (Duke 1985). The principal valerian alkaloids are actinidine, chatinine, valerianine, valerine, alpha-methyl pyrryl ketone and naphthyridin methyl ketone (Torssell and Wahlberg 1967, Franck et al 1970, Janot et al 1979. The structures of some valerian alkaloids are shown in Fig.…”

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“…There is little correlation between the content of volatile oils and the plant's clinical effects. 50 Valerian's effects on the central nervous system have been variously attributed to valepotriates, their breakdown products (baldrinals), valerenic acid, valerenal and valeranone, and other constituents in the essential oil 32,[51][52] . [56][57] Other Constituents: Amino acids (e.g.…”

Heterocyclic Compounds in Alkaloid Synthesis

“…Heterocyclic Ring Interconversion. An efficient and general approach to the pyran ring is via a Diels-Alder reaction (Scheme 41) (Wollweber, 1972), and this principle has Franck et al (1970).] Such a process has biogenetic significance since iridoid glycoside monoterpenes coexist in many of the plants from which alkaloids have been isolated (Taylor and Battersby, 1969).…”

“…In the synthesis of 5-hydroxyactinidine (Scheme 40), nitrogen incorporation was simply achieved by reaction of iridodial with a source of ammonia. been adopted in the synthesis of valerianine (Franck et al, 1970). In fact, in some cases, of which gentianine (Fig.…”