Frullania tamarisci

Singh, M. and Singh, J., New flavonoids from Frullania tamarisci, Fitoterapia, 62, 187, 1991. 

The liverworts normally associated with woodcutter s eczema are Frullania dilatata Dum., Frullania tamarisci Dum. ssp. nisquallensis Hatt. (syn. F. nisquallensis SuU.) and Frullania tamarisci Dum. ssp. tamarisci (syn. F. tamarisci Dum.) (fam. Jubulaceae). Mitchell et al. (1970) patch tested a patient with a total of 12 different North American Frullania species (as is) (Table 1) only one (F. squarrosa Dum.) failed to elicit a response. 

Connolly JD, Thornton IMS (1973) Sesquiterpenoid lactones from the liverwort Frullania tamarisci. Phytochem 12 631-632 Culberson CF (1969) Chemical and botanical guide to lichen products. University of North Carolina Press, Chapel Hill Dahlquist I, Fregert S (1980) Contact allergy to atranorin in lichens and perfumes. Contact Dermatitis 6 111-119 Dahlquist I, Fregert S (1981) Atranorin and oak moss contact allergy. Contact Dermatitis 7 168-169 Fernandez de Corres L (1984) Contact dermatitis from frullania ... 

Frullanolide, a sesquiterpene lactone, is contained in Frullania tamarisci (l) Dum. (L-Frullanolide) and Frullania dilatata (l) Dum. (o-frullanolide). Sensitivity causes mainly airborne contact dermatitis in forest rangers, lumbermen, sawyers, carpenters, and merchants in rough timber. 

Incubation of (-)-frullanolide (226), obtained from the European liverwort Frullania tamarisci subsp. tamarisci that causes a potent allergenic contact dermatitis, was incubated by A. niger to give dihydrofrullanolide (227), nonallergenic compound in 31.8% yield. In this case, C11-C13 dihydro derivative was not obtained (Hashimoto et al., 2005). 

Connolly ID, Harrison LJ, Rycroft DS 1984 The structure of tamariscol, a new pacifigorgiane sesquiterpenoid alcohol from the liverwort Frullania tamarisci. Tetra Lett 25 1401-1402... 

Frullanolide (338), with a d s-lactone ring, has been isolated from the epiphytic liverwort, Frullania tamarisci. The structure was deduced from its spectral properties (775,255, 287) and confirmed by conversion to l,2-dihydro-6-epi-P-santonin (366) also obtained from 6-epi-P-santonin (367) (775, 287) (Scheme 40). The enantiomer (339) of (338) was isolated from European F, dilatata (30, 175, 287). 

Japanese Frullania tamarisci ssp. obscura is morphologically quite similar to European F. tamarisci. However, the chemical constitution is quite different. Two new eudesmane-type sesquiterpenes, eudesmanal (334), and 4-epi-arbusculin A (351) have been isolated from Japanese material 31). The structures of (334) and (351) were based on spectroscopic evidence ( H-NMR and CD) and chemical correlation with a co-metabolite P-cyclocostunolide (345) as well as y-cyclocostunolide (346) as shown in Scheme 43. The H-NMR spectrum of (351) resembled that of arbusculin... 

Conocephalum conicum Frullania tamarisci ssp. tamarisci Jamesonidla autiimnalis J. undulifolia Marchantia polymorpha Plagiochila asplenioides P. carringtonii... 

In North America and Europe, it has long been known that some occupational allergies are associated with handling of wood on which epiphitic liverworts grow. The hapten of this allergy is a sesquiterpene lactone, (—)-frullanolide (338), isolated from Frullania tamarisci ssp. tamarisci, or ( + )-frullanolide (339) from F. dilatata 14,18, 30, 32,37,175, 255, 287). The isolation of these compounds represented the first discovery in bryophytes of compounds with biological activity in humans. The eudesmanolides (349) and (352) and the eremophilanolide (322) also caused intense allergies. Patients sensitive to Frullania species are all sensitive to at least one of the lactones isolated from F. dilatata 30). 

Frullania tamarisci ssp. obscura Campesterol Stigmasterol Sitosterol... 

Asakawa, Y., G. Ourisson, and T. Aratani New Sesquiterpene Lactones and Aldehyde of Frullania tamarisci subsp. obscura (Hepaticae). Tetrahedron Letters 1975,3957. 

SuiRE, C., and G. Burgeois Les Monoterpenes de Conocephalum conicum, Frullania tamarisci and Porella platyphylla. Phytochem. 16, 284 (1977). 

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