The sesquiterpene constituents of the liverwort Preissia quadrata

König, Wilfried Α.; Bülow, Nils; Fricke, Christiane; Melching, Stephanie; Rieck, Angela; Muhle, Hermann

doi:10.1016/0031-9422(96)00354-8

Cited by 51 publications

(15 citation statements)

References 11 publications

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“…The sesquiterpenes 10 -12 obtained in the present work were found to be identical in their spectral data with spathulenol (data compared with those of an authentic sample), alismol 17,18 and alismoxide, 17 respectively. Direct comparison of the spectral data of 13 with those of 4β,10α-aromadendranediol proved their identity.…”

Section: Resultssupporting

confidence: 50%

Terpenoid constituents from leaves of Guarea kunthiana

Garcez¹,

Garcez²,

Silva³

et al. 2004

J. Braz. Chem. Soc.

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sesquiterpenos (alismol, alismóxido, espatulenol e 4β,10α-aromadendranodiol), poliprenol-12 e α-e δ-tocoferóis. Kolavenal está sendo relatado pela primeira vez como produto natural, assim como a ocorrência de diterpenos do tipo cembrano e ent-caurano na família Meliaceae.From leaves of Guarea kunthiana one new kaurene diterpene (ent-kaur-16-en-2-one) was isolated along with eight known diterpenes (ent-kaur-16-ene, ent-3α-and 3β-hydroxykaur-16-ene, kolavelool, kolavenol, kolavenal, ent-13-epi-manoyloxide and (-)-nephthenol), four sesquiterpenes (alismol, alismoxide, spathulenol and 4β,10α-aromadendranediol), polyprenol-12 and α-and δ-tocopherols. Kolavenal is reported for the first time as a natural product, as well as the occurrence of cembrane-and ent-kaurane-type diterpenes in the Meliaceae.

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Section: Resultssupporting

confidence: 50%

Terpenoid constituents from leaves of Guarea kunthiana

Garcez¹,

Garcez²,

Silva³

et al. 2004

J. Braz. Chem. Soc.

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“…8C). This finding is interesting because the ( R )-enantiomer is known to occur widely in early vascular plants such as liverworts, but was thought to be less prevalent in angiosperms (König et al, 1996). …”

Section: Resultsmentioning

confidence: 95%

Biosynthesis of sesquiterpenes in grape berry exocarp of Vitis vinifera L.: Evidence for a transport of farnesyl diphosphate precursors from plastids to the cytosol

2013

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The participation of the mevalonic acid (MVA) and 1-deoxy-D-xylulose 5-phosphate/2-C-methyl-D-erythritol-4-phosphate (DOXP/MEP) pathways in sesquiterpene biosynthesis of grape berries was investigated. There is an increasing interest in this class of terpenoids, since the oxygenated sesquiterpene rotundone was identified as the peppery aroma impact compound in Australian Shiraz wines. To investigate precursor supply pathway utilization, in vivo feeding experiments were performed with the deuterium labeled, pathway specific, precursors [5,5-2H2]-1-deoxy-D-xylulose and [5,5-2H2]-mevalonic acid lactone. Head Space-Solid Phase Micro Extraction-Gas Chromatography-Mass Spectrometry (HS-SPME-GC-MS) analysis of the generated volatile metabolites demonstrated that de novo sesquiterpene biosynthesis is mainly located in the grape berry exocarp (skin), with no detectable activity in the mesocarp (flesh) of the Lemberger variety. Interestingly, precursors from both the (primarily) cytosolic MVA and plastidial DOXP/MEP pathways were incorporated into grape sesquiterpenes in the varieties Lemberger, Gewürztraminer and Syrah. Our labeling data provide evidence for a homogenous, cytosolic pool of precursors for sesquiterpene biosynthesis, indicating that a transport of precursors occurs mostly from plastids to the cytosol. The labeling patterns of the sesquiterpene germacrene D were in agreement with a cyclization mechanism analogous to that of a previously cloned enantioselective (R)-germacrene D synthase from Solidago canadensis. This observation was subsequently confirmed by enantioselective GC-MS analysis demonstrating the exclusive presence of (R)-germacrene D, and not the (S)-enantiomer, in grape berries.

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“…Although the absolute configurations of most of these products have not been described, ␤-caryophyllene from plants has been believed to have a (Ϫ) form. Some liverworts produce "unusual" (ϩ)-␤-caryophyllene (34,35). In bacteria, marine arctic strains of the Cytophaga-Flavobacterium-Bacteroides group produce ␤-caryophyllene, although the absolute configuration has not been determined (36).…”

Section: Discussionmentioning

confidence: 99%

Characterization of a Novel Sesquiterpene Cyclase Involved in (+)-Caryolan-1-ol Biosynthesis in Streptomyces griseus

Nakano

Horinouchi²,

Ohnishi

2011

Journal of Biological Chemistry

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Most terpenoids have been isolated from plants and fungi and only a few from bacteria. However, an increasing number of genome sequences indicate that bacteria possess a variety of terpenoid cyclase genes. We characterized a sesquiterpene cyclase gene (SGR2079, named gcoA) found in Streptomyces griseus. When expressed in Streptomyces lividans, gcoA directed production of a sesquiterpene, isolated and determined to be (؉)-caryolan-1-ol using spectroscopic analyses. (؉)-Caryolan-1-ol was also detected in the crude cell lysate of wild-type S. griseus but not in a gcoA knockout mutant, indicating that GcoA is a genuine (؉)-caryolan-1-ol synthase. Enzymatic properties were characterized using N-terminally histidine-tagged GcoA, produced in Escherichia coli. As expected, incubation of the recombinant GcoA protein with farnesyl diphosphate yielded (؉)-caryolan-1-ol. However, a small amount of another sesquiterpene was also detected. This was identified as the bicyclic sesquiterpene hydrocarbon (؉)-␤-caryophyllene by comparison with an authentic sample using GC-MS. Incorporation of a deuterium atom into the C-9 methylene of (؉)-caryolan-1-ol in an in vitro GcoA reaction in deuterium oxide indicated that (؉)-caryolan-1-ol was synthesized by a proton attack on the C-8/C-9 double bond of (؉)-␤-caryophyllene. Several ␤-caryophyllene synthases have been identified from plants, but these cannot synthesize caryolan-1-ol. Although caryolan-1-ol has been isolated previously from several plants, the enzyme responsible for its biosynthesis has not been identified previously. GcoA is thus the first known caryolan-1-ol synthase. Isolation of caryolan-1-ol from microorganisms is unprecedented.Terpenoids are the largest family of natural products, including over 24,000 known compounds. They have various biological functions and act as flavorings, pigments, antibiotics, hormones, and antitumor agents. Most terpenoids have been isolated from plants and fungi and only a few from bacteria. All terpenoids are derived from the C 5 precursors isopentenyl diphosphate and dimethylallyl diphosphate. The successive condensation of isopentenyl diphosphate and dimethylallyl diphosphate gives rise to linear isoprenyl diphosphate precursors of various chain lengths, such as geranyl diphosphate (C 10 ), farnesyl diphosphate (FPP, 2 C 15 ), and geranylgeranyl diphosphate (C 20 ). These linear substrates are generally cyclized by terpenoid cyclases to produce the parent skeletons of monoterpenes (C 10 ), sesquiterpenes (C 15 ), diterpenes (C 20 ), and other homologs. Terpenoid cyclases are therefore the first key enzymes in pathways leading to the diverse range of terpenoids. A large number of terpenoid cyclases have been reported from eukaryotes, and these have been studied extensively (1, 2). In contrast, at present there are only a small number of reports of bacterial terpenoid cyclases. Most of the bacterial terpenoid cyclases reported are sesquiterpene cyclases (SCs). Bacterial SCs show no significant amino acid sequence identity with eukaryotic S...

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The sesquiterpene constituents of the liverwort Preissia quadrata

Cited by 51 publications

References 11 publications

Terpenoid constituents from leaves of Guarea kunthiana

Terpenoid constituents from leaves of Guarea kunthiana

Biosynthesis of sesquiterpenes in grape berry exocarp of Vitis vinifera L.: Evidence for a transport of farnesyl diphosphate precursors from plastids to the cytosol

Characterization of a Novel Sesquiterpene Cyclase Involved in (+)-Caryolan-1-ol Biosynthesis in Streptomyces griseus

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