Sesquiterpenoid lactones from the liverwort Frullania tamarisci

Connolly, Joseph D.; Thornton, Ian M. S.

doi:10.1016/s0031-9422(00)84456-8

Cited by 31 publications

(10 citation statements)

References 6 publications

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“…A number of allergens were isolated from the Frullania species. They were all α‐methylene‐γ‐butyrolactone sesquiterpenes 17,18. As an example, Knoche et al isolated frullanolide from Frullania tamarisci (L.) Dum 19.…”

Section: Allergic Contact Dermatitis To α‐Methylene‐γ‐butyrolactonesmentioning

confidence: 99%

α‐methylene‐γ‐butyrolactones: versatile skin bioactive natural products

Lepoittevin

Berl

Giménez‐Arnau

2009

The Chemical Record

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Natural products containing an alpha-methylene-gamma-butyrolactone moiety, mainly of the sesquiterpene type, are widely observed in plants, which upon coming into contact with skin, will induce major skin toxicological side effects or phytodermatitis. Indeed two main dermatological pathologies have been associated with a skin exposure to molecules containing an alpha-methylene-gamma-butyrolactone moiety: allergic contact dermatitis (ACD) and chronic actinic dermatitis (CAD). ACD is an immunologically based disease resulting from modifications of epidermal proteins by sensitizers or haptens. Indeed, alpha-methylene-gamma-butyrolactones are highly electrophilic structures that can act as Michael acceptors towards nucleophilic residues of proteins. Cysteine and lysine are the most modified residues leading, in the case of enantiomerically pure lactones, to the formation of diastereomeric adducts. This chemical enantioselectivity induces an enantiospecificity of the allergic reaction, i.e., an individual sensitized to one enantiomer will not develop clinical symptoms when exposed to the other enantiomer and vice versa. Sesquiterpene lactones have been also associated with another pathology that involves UV irradiation and DNA modifications. Interestingly, it was found that alpha-methylene-gamma-butyrolactones, in addition to their electrophilic properties, were highly photoreactive molecules able to react with thymine/thymidine to form [2 + 2] photoadducts in very high yields. In all cases a syn regioselectivity was observed, probably associated with the polarization of the exomethylenic bond. This high photoreactivity of alpha-methylene-gamma-butyrolactones towards thymidine could be an explanation of the progressive evolution of allergic contact dermatitis towards chronic actinic dermatitis.

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Section: Allergic Contact Dermatitis To α‐Methylene‐γ‐butyrolactonesmentioning

confidence: 99%

α‐methylene‐γ‐butyrolactones: versatile skin bioactive natural products

Lepoittevin

Berl

Giménez‐Arnau

2009

The Chemical Record

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“…For this reason, the volatile secondary metabolites found in liverworts are well‐documented, most of them are terpene compounds (mono‐, sesqui‐ and diterpenoids) and small aromatic compounds . Volatile components of Frullania were mostly identified in solvent extracts and to our knowledge, only one study deals with the composition of F. tamarisci essential oil . Seven chemical compositions were described from the ether extracts of 83 Frullania species and according to the considered subspecies; F. tamarisci was characterized by diterpenes with labdane skeleton (subsp.…”

Section: Introductionmentioning

confidence: 99%

“…Among them, frullanolide, an eudesmane‐type sesquiterpene lactone, was considered as a taxanomical marker of Frullania genus whereas (−)‐frullanolide is known to cause strong allergenic contact dermatitis . The others sesquiterpene lactones identified in Frullania were 4‐epi‐arbusculine A, α‐cyclocostunolide and β‐cyclocostunolide, a dimer of 4‐epi‐arbusculine A and 4α,6α‐dihydroxy‐11(13)‐eudesman‐12‐al, γ‐cyclocostunolide and costunolide . In addition, some hydrocarbon sesquiterpenes as hinesene, β‐caryophyllene, β‐elemene, 4,5‐di‐epi‐aristolochene, bicyclogermacrene, α‐humulene and eremophilene were identified …”

Section: Introductionmentioning

confidence: 99%

New advances in the volatile metabolites of Frullania tamarisci

Pannequin

Tintaru

Desjobert

et al. 2017

Flavour & Fragrance J

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The chemical composition of Frullania tamarisci essential oil from Corsica was investigated using GC‐FID, GC–MS and NMR analyses. The essential oil compositions were further studied analyzing samples prepared from three different Corsican locations and during a seasonal vegetative cycle. 40 components, which accounted for 78.3–89.8% of the total amount of F. tamarisci essential oils were identified. The main components were tamariscol coeluted with pacifigorgiol (30.4–41.5%), germacra‐1(10)E,5E–dien‐11‐ol (3.6–7.1%), γ‐cylocostunolide (1.8–20.1%), γ‐dihydrocyclocostunolide (1.2–8.0%) and frullanolide (1.7–4.9%). Among them, germacra‐1(10)E,5E–dien‐11‐ol was never reported in the Frullania genus and pacifigorgiol, a tamariscol GC‐overlapped compound, was for the first time reported in Bryophytes. Finally using 1D and 2D NMR experiments, we reported γ‐dihydrocyclocostunolide as a new natural compound. Two Corsican F. tamarisci essential oils with different GC profiles were assessed for their phytotoxic behavior against onion seeds and seedling in order to evaluate their capacity to inhibit germination and alter the development of plantlets. According to the essential oil‐compositions, a stimulation of the onion seedling was observed when sesquiterpene lactones amount was higher, whilst the inhibition of roots growth occurs when sesquiterpene alcohols were predominantly.

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“…the species that have been investigated are!.. :_ nisquallensis (Su11) (3), f.:._ tamarisci (6,7), .E. !_ brittonia (Evans) (7,8), and I:_ dilatata (7,8).…”

Section: Introductionmentioning

confidence: 99%

Isolation and characterization of frullanolide from Frullania franciscana (Howe)

Sass¹

2000

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Sesquiterpenoid lactones from the liverwort Frullania tamarisci

Cited by 31 publications

References 6 publications

α‐methylene‐γ‐butyrolactones: versatile skin bioactive natural products

α‐methylene‐γ‐butyrolactones: versatile skin bioactive natural products

New advances in the volatile metabolites of Frullania tamarisci

Isolation and characterization of frullanolide from Frullania franciscana (Howe)

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