Sesquiterpene hydrocarbons in the liverwort dumortiera hirsuta

Saritas, Yücel; Bülow, Nils; Fricke, Christiane; König, Wilfried Α.; Muhle, Herman

doi:10.1016/s0031-9422(97)00484-6

Cited by 33 publications

(19 citation statements)

References 12 publications

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“…The achiral, monocyclic sesquiterpene 5 is abundant in many essential oils and was reported from different sources such as the liverwort Dumortiera hirsuta [19]. Its ( Z )-configured exocyclic double bond has also attracted the attention of synthetic chemistry for a diastereoselective total synthesis [20–22].…”

Section: Resultsmentioning

confidence: 99%

Stereochemical investigations on the biosynthesis of achiral (Z)-γ-bisabolene in Cryptosporangium arvum

Rinkel

Dickschat

2019

Beilstein J. Org. Chem.

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A newly identified bacterial (Z)-γ-bisabolene synthase was used for investigating the cyclisation mechanism of the sesquiterpene. Since the stereoinformation of both chiral putative intermediates, nerolidyl diphosphate (NPP) and the bisabolyl cation, is lost during formation of the achiral product, the intriguing question of their absolute configurations was addressed by incubating both enantiomers of NPP with the recombinant enzyme, which resolved in an exclusive cyclisation of (R)-NPP, while (S)-NPP that is non-natural to the (Z)-γ-bisabolene synthase was specifically converted into (E)-β-farnesene. A hypothetical enzyme mechanistic model that explains these observations is presented.

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Section: Resultsmentioning

confidence: 99%

Stereochemical investigations on the biosynthesis of achiral (Z)-γ-bisabolene in Cryptosporangium arvum

Rinkel

Dickschat

2019

Beilstein J. Org. Chem.

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“…Dumortiera hirsuta grows on wet rocks and is widespread over China. Previous studies on this species led to the isolation of several novel sesquiterpenoids and some bisbibenzyls [5,6]. In this paper, we report the isolation and characterization of four new monoterpene esters (1-4) from C. conicum in addition to seven known compounds including 5 from C. conicum and 6-11 from D. hirsute.…”

Section: Introductionmentioning

confidence: 89%

Terpenoids and bisbibenzyls from Chinese liverwortsConocephalumconicumandDumortierahirsuta

Fan

et al. 2006

Journal of Asian Natural Products Research

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Four new monoterpene esters, 2alpha,5beta-dihydroxybornane-2-cinnamate (1), 2alpha,5beta-dihydroxybornane-5-acetyl-2-cinnamate (2), 2alpha,5beta-dihydroxybornane-2-p-hydroxycinnamate (3) and 2alpha,5beta-dihydroxy-bornane-2-cis-p-hydroxycinnamate (4), together with a known compound 3,4-dimethoxystyrene (5) were isolated from Chinese liverwort Conocephalum conicum and six known compounds, 5,7-dihydroxycalamenene (6), 7-hydroxycalamenene (7), lunularin (8), riccardin C (9), marchantin C (10) and riccardin D (11) were isolated from Dumortiera hirsuta. Their structures were elucidated by extensive spectral analysis and chemical correlations. Compounds 1 and 8 showed moderate cytotoxicity against human HepG2 cells with IC50 4.5 microg/ml and 7.4 microg/ml, respectively, while compound 8 also showed antimicrobacterial activity against Pseudomonas aeruginosa with minimum inhibitory concentration at 64 microg/ml.

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“…Sesquiterpenoids are the most characteristic compounds of D. hirsuta species identified so far, which have been reported mainly for samples from Asia and the American continent [6]. Saritas et al [16], by using gas chromatography, identified β-caryophyllene, αcubebene, valencene, α-guaiene, γ-gurjunene, in samples of D. hirsuta from Brazil. These components were also found in D. hirsuta subsp.…”

Section: Extraction Of the Volatile And Semivolatile Compounds Of Thementioning

confidence: 99%

An Analysis of Volatile Components of the Liverworts Dumortiera hirsuta subsp. hirsuta and Dumortiera hirsuta subsp. nepalensis (Dumortieraceae) from Panama and Taxonomic Observations on the Species

Durant-Archibold

Allen

Garrido

et al. 2018

Natural Product Communications

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We report for the first time the chemical composition of volatile components (VOCs) of two subspecies, D. hirsuta subsp. hirsuta and D. hirsuta subsp. nepalensis, of the liverwort Dumortiera hirsuta from Panama by using headspace-solid phase microextraction-gas chromatography-mass spectrometry in order to assess distinguishing markers between the two species. Forty VOCs were identified in total for both subspecies. Of these, 34 are reported for the first time in D. hirsuta. Furthermore, both subspecies showed clear differences in the type and amount of VOCs. The major compounds in D. hirsuta subsp. hirsuta were α-gurjunene, β-selinene, α-guaiene, α-humulene and β-caryophyllene; while in D. hirsuta subsp. nepalensis were ledene, α-gurjunene, β-caryophyllene and α-guaiene, respectively. Two oxygenated sesquiterpenes, globulol and nerolidol, could be considered as possible distinguishing chemical markers between these two subspecies. We conclude that both morphotypes of D. hirsuta are chemically different.

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Sesquiterpene hydrocarbons in the liverwort dumortiera hirsuta

Cited by 33 publications

References 12 publications

Stereochemical investigations on the biosynthesis of achiral (Z)-γ-bisabolene in Cryptosporangium arvum

Stereochemical investigations on the biosynthesis of achiral (Z)-γ-bisabolene in Cryptosporangium arvum

Terpenoids and bisbibenzyls from Chinese liverwortsConocephalumconicumandDumortierahirsuta

An Analysis of Volatile Components of the Liverworts Dumortiera hirsuta subsp. hirsuta and Dumortiera hirsuta subsp. nepalensis (Dumortieraceae) from Panama and Taxonomic Observations on the Species

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