Drimane-Type Sesquiterpenoids as Chemosystematic Markers of Canellaceae

Bastos, Jairo Kenupp; Kaplan, M. A. C.; Gottlieb, Otto R.

doi:10.1590/s0103-50531999000200011

Cited by 17 publications

(13 citation statements)

References 14 publications

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“…The relationship ((Warburgia + Capsicodendron/ South American Cinnamodendron) Cinnamosma) is recovered here for the first time ( Fig. 1) and is congruent with the composition of secondary metabolites (Bastos et al, 1999). Thorough morphological re-investigation, possibly including pollen characteristics as well as the inclusion of fossils, in the light of our molecular phylogenetic results, are advisable prior to a genus level revision.…”

Section: Phylogeny Systematics and Morphologysupporting

confidence: 66%

Intercontinental long-distance dispersal of Canellaceae from the New to the Old World revealed by a nuclear single copy gene and chloroplast loci

Müller

Salomo

Salazar

et al. 2015

Molecular Phylogenetics and Evolution

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Canellales, a clade consisting of Winteraceae and Canellaceae, represent the smallest order of magnoliid angiosperms. The clade shows a broad distribution throughout the Southern Hemisphere, across a diverse range of dry to wet tropical forests. In contrast to their sister-group, Winteraceae, the phylogenetic relations and biogeography within Canellaceae remain poorly studied. Here we present the phylogenetic relationships of all currently recognized genera of Canellales with a special focus on the Old World Canellaceae using a combined dataset consisting of the chloroplast trnK-matK-trnK-psbA and the nuclear single copy gene mag1 (Maigo 1). Within Canellaceae we found high statistical support for the monophyly of Warburgia and Cinnamosma. However, we also found relationships that differ from previous studies. Cinnamodendron splitted into two clades, a South American clade and a second clade confined to the Antilles and adjacent areas. Cinnamodendron from the Antilles, as well as Capsicodendron, South American Cinnamodendron and Pleodendron were not monophyletic. Consequently, Capsicodendron should be included in the South American Cinnamodendron clade and the genus Pleodendron merged with the Cinnamodendron clade from the Antilles. We also found that Warburgia (restricted to mainland eastern Africa) together with the South American Cinnamodendron and Capsicodendron are sister to the Malagasy genus Cinnamosma. In addition to the unexpected geographical relationships, both biogeographic and molecular clock analyses suggest vicariance, extinction, and at least one intercontinental long-distance-dispersal event. Our dating result contrasts previous work on Winteraceae. Diversification of Winteraceae took place in the Paleocene, predating the Canellaceae diversification by 13 MA in the Eocene. The phylogenetic relationships for Canellaceae supported here offer a solid framework for a future taxonomic revision of the Canellaceae.

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Section: Phylogeny Systematics and Morphologysupporting

confidence: 66%

Intercontinental long-distance dispersal of Canellaceae from the New to the Old World revealed by a nuclear single copy gene and chloroplast loci

Müller

Salomo

Salazar

et al. 2015

Molecular Phylogenetics and Evolution

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“…Further fractionation of the dichloromethane extract of the stem bark resulted in the isolation of three more drimane lactones, 3acetoxycinnamolide (37a, 37c, 37d), and the previously known mukaadial (55) [30]. Further investigation of the same plant led to the isolation of polygodial (1a), mukaadial (55), caspicodendrin (67), whose structures was revised by our group [20], isopolygodial (2) and polygonone (27), together with cinnamodial (54) [33].…”

mentioning

confidence: 93%

“…W. salutaris) [23][24][25][26][27][28][29][30][31], which is distributed in east Africa, and W. stuhlmannii [25] in South Africa; family Canellaceae. 4) Caspicodendron dinisii [32,33] in South America, Canella winterana [34,35] in the Caribbean and subtropical Florida; family Canellaceae. 5) Tasmannia lanceolata [36,37] in Tasmania and in part of mainland Australia; family Winteraceae.…”

mentioning

confidence: 99%

Distribution of Drimane Sesquiterpenoids and Tocopherols in Liverworts, Ferns and Higher Plants: Polygonaceae, Canellaceae and Winteraceae Species

Asakawa

Ludwiczuk

Harinantenaina

et al. 2012

Natural Product Communications

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The liverwort, Porella vernicosa complex produces a very hot tasting polygodial, a drimane-type sesquiterpene dialdehyde. The same compound has been isolated from two ferns, Thelypteris hispidula and Blechnum fluviatile, as well as from the higher plants Polygonum hydropiper, P. hydropiper f. purpurascens (Polygonaceae), Cinnamosma, Caspicodendron, Canella and Warburgia species (Canellaceae), and Pseudowintera colorata, Tasmannia lanceolata, Drimys and Zygogynum species (Winteraceae). In addition, the liverworts and higher plants which elaborate polygodial and its related pungent drimane dials contain a small amount of -tocopherol, -tocopherol or -tocotrienol. The present paper gives the results of a comparative study on the drimane-type sesquiterpenoids in some liverworts, ferns and higher plants, and the role of tocopherols in these plant groups.

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“…3 The genera Canella (tropical America) and Warburgia (East Africa) are the most studied members of the family, while only limited phytochemical data are available for other genera. 4 A detailed distribution of sesquiterpenes identified from six Canellaceae species (belonging to the genera Canella, Capsicodendron, Cinnamosma, and Warburgia) has listed a total of 19 drimanetype sesquiterpenes plus their derivatives. 5 Each species contained from six to 10 of these compounds.…”

mentioning

confidence: 99%

Phytochemistry and Antifungal Properties of the Newly Discovered Tree Pleodendron costaricense

Amiguet

Petit

et al. 2006

J. Nat. Prod.

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Gas chromatography analysis of the essential oils of leaves and bark collected from the newly discovered tree Pleodendron costaricense identified alpha-pinene, beta-pinene, beta-myrcene, beta-thujene, and beta-caryophyllene as their major constituents. Phytochemical analysis of P. costaricense parts led to the isolation and identification of delta-tocotrienol, beta-sitosterol, four known drimane-type sesquiterpenes, cinnamodial (1), cinnamosmolide (2), polygodial (3), and mukaadial (4), and two new compounds, a drimane-type sesquiterpene, parritadial (5), and an eremophilane-type sesquiterpene, pleodendione (6). Antifungal assays with the two major compounds, 1 and 2, were carried out, and results showed a high activity of 1 against Alternaria alternata (MIC = 3.9 microg/mL), Candida albicans azole-resistant strain D10, and Wangiella dermatitides (MICs = 15.6 microg/mL). Compound 2 showed less potent antifungal activities than 1 but was more effective against Candida albicans azole-resistant strain CN1A (MIC = 23.4 microg/mL) and Pseudallescheria boydii (MIC = 78.1 microg/mL). A combination of the dialdehyde sesquiterpenes with dillapiol showed a synergistic antifungal effect with 1 and an additive effect with 4 and 5.

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Drimane-Type Sesquiterpenoids as Chemosystematic Markers of Canellaceae

Cited by 17 publications

References 14 publications

Intercontinental long-distance dispersal of Canellaceae from the New to the Old World revealed by a nuclear single copy gene and chloroplast loci

Intercontinental long-distance dispersal of Canellaceae from the New to the Old World revealed by a nuclear single copy gene and chloroplast loci

Distribution of Drimane Sesquiterpenoids and Tocopherols in Liverworts, Ferns and Higher Plants: Polygonaceae, Canellaceae and Winteraceae Species

Phytochemistry and Antifungal Properties of the Newly Discovered Tree Pleodendron costaricense

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