Eremophilanolides and other constituents from the Argentine liverwort Frullania brasiliensis

Bardón, Alicia; Mitre, Graciela Bovi; Kamiya, Norma; Toyota, Masao; Asakawa, Yoshinori

doi:10.1016/s0031-9422(01)00452-6

Cited by 31 publications

(22 citation statements)

References 21 publications

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“…1). AA occurs in lichens and has been isolated from higher plants like Newbouldia laevis (Gormann et al, 2003), Alseodaphne andersonii (Lee et al, 2001), Acer nikense (Nagumo et al, 1996) and Frullania brasiliensis (Bardón et al, 2002). Previously it was found as a degradation product of various natural depsides.…”

Section: The Natural Compounds Aa and Nbbsmentioning

confidence: 99%

The natural compounds atraric acid and N-butylbenzene-sulfonamide as antagonists of the human androgen receptor and inhibitors of prostate cancer cell growth

Roell

Baniahmad

2011

Molecular and Cellular Endocrinology

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International audienceExtracts from the plant are widely used in the therapy of benign prostate hyperplasia (BPH) and in combinational therapy for prostate cancer, the second leading cause of cancer death and the mostly diagnosed form of cancer in men. The androgen receptor (AR) plays a crucial role in the development of the prostate as well as in prostate diseases. Even though the extracts from are considered as beneficial for prostate diseases in clinical trials, and some active compounds for treatment of BPH could be identified, compounds responsible for AR inhibition and the molecular mechanism for inhibition of prostatitis need to be identified. Recently, atraric acid and N-butylbenzene-sulfonamide were isolated from a selective dichlormethane extract of as two novel AR antagonistic compounds. The molecular mechanisms of AR inhibition were analyzed and are summarized here. Both compounds are the first known natural, complete and specific AR antagonist

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Section: The Natural Compounds Aa and Nbbsmentioning

confidence: 99%

The natural compounds atraric acid and N-butylbenzene-sulfonamide as antagonists of the human androgen receptor and inhibitors of prostate cancer cell growth

Roell

Baniahmad

2011

Molecular and Cellular Endocrinology

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“…Compounds of Frullania hamatiloba have been isolated and their structures were determined by a combination of the 1 H-and 13 C-NMR, MS, ultraviolet-visible spectroscopy (UV), IR, and X-ray crystallographic (X-ray) analysis [11]. In another species of this genus, the F. brasiliensis two eremophilanolides were established by NMR and X-ray analysis [12].…”

Section: Introductionmentioning

confidence: 99%

Volatile Metabolites in Liverworts of Ecuador

et al. 2020

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Volatile metabolites from Frullania brasiliensis Raddi, Herbertus juniperoideus (Sw.) Grolle, Leptoscyphus hexagonus (Nees) Grolle, and Syzygiella anomala (Lindenb. & Gottsche) Steph collected in the south of Ecuador were investigated. Volatile secondary metabolites were extracted by hydrodistillation and analyzed by gas chromatography/flame ionization detector (GC/FID) and Gas chromatography/Mass spectrometry (GC/MS). Sixty-seven volatile compounds were identified in the four species, which represent between 80.12–90.17% of the total chemical composition. The major components were τ-muurolol (32.14%) and Germacrene-D (11.98%) in the essential oil of F. brasiliensis, bicyclogermacrene (18.23%), and Caryophyllene oxide (15.29%) in the oil of H. juniperoideus, Cabreuva oxide D (33.77%) and Elemol (18.55%) in the oil of Leptoscyphus hexagonus, and Silphiperfola-5,7(14)-diene (25.22%) and Caryophyllene oxide (8.98%) in the oil of Syzygiella anomala. This is the first report on volatile compounds for the species Herbertus juniperoideus, Leptoscyphus hexagonus, and Syzygiella anomala.

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“…The gem-dimethyl cyclopropane located at C(6) and C(7) of the secoaromadendrane skeleton in compound 1 is a structural feature shared with plagiochilines A and M (2 and 3, resp.). Additionally, the presence of a methyl ester could be inferred from the Me signal at d(C) 51.3 in the 13 C-NMR that correlated with the singlet at d(H) 3.74 in the HMQC spectrum (supporting information). The location of the methyl ester was evident by the cross-peak between the H-atom signals of this Me group, HÀC(3), and HÀC(5) and the 13 C signal at d(C) 166.2 assigned to C(15) of the secoaromadendrane backbone, in the HMBC spectrum ( Table 1).…”

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confidence: 95%

“…Additionally, the presence of a methyl ester could be inferred from the Me signal at d(C) 51.3 in the 13 C-NMR that correlated with the singlet at d(H) 3.74 in the HMQC spectrum (supporting information). The location of the methyl ester was evident by the cross-peak between the H-atom signals of this Me group, HÀC(3), and HÀC(5) and the 13 C signal at d(C) 166.2 assigned to C(15) of the secoaromadendrane backbone, in the HMBC spectrum ( Table 1). Moreover, a signal at d(C) 65.4, which correlated in the HSQC spectrum with the signals at d(H) 4.37 and 4.88, evidenced the presence of the typical AB system of a CH 2 group attached to an ester chain which was assigned to CH 2 (14) (Fig.…”

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confidence: 95%

Insecticidal Constituents from the Argentine Liverwort Plagiochila bursata

Ramirez

Kamiya²,

Popich

et al. 2010

Chemistry & Biodiversity

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The new 2,3-secoaromadendrane 1, together with the known compounds plagiochilines A and M (2 and 3, resp.), fusicogigantone A (4), and 1,4-dimethylazulene (5) were isolated from an Argentine collection of the liverwort Plagiochila bursata. Structures were elucidated by extensive 1D- and 2D-NMR studies. Compounds 2 and 4, incorporated to the larval diet at 100 microg per g of diet, reduced the larval growth of Spodoptera frugiperda (Lepidoptera: Noctuidae) by 66+/-29% and 25+/-8% and produced 55 and 75% larval mortality at early instars and 20 and 25% pupal mortality, respectively. Treatment with compound 2 also produced abdomen and wing malformation in adults leading to impossibility to mate.

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Eremophilanolides and other constituents from the Argentine liverwort Frullania brasiliensis

Cited by 31 publications

References 21 publications

The natural compounds atraric acid and N-butylbenzene-sulfonamide as antagonists of the human androgen receptor and inhibitors of prostate cancer cell growth

The natural compounds atraric acid and N-butylbenzene-sulfonamide as antagonists of the human androgen receptor and inhibitors of prostate cancer cell growth

Volatile Metabolites in Liverworts of Ecuador

Insecticidal Constituents from the Argentine Liverwort Plagiochila bursata

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