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PubMed2001

Recent advances in phytochemistry of bryophytes-acetogenins, terpenoids and bis(bibenzyl)s from selected Japanese, Taiwanese, New Zealand, Argentinean and European liverworts.

Bryophytes contain a large number of terpenoids and phenolic compounds. Recent topics relating to the chemical constituents found in 36 Japanese, 3 New Zealand, 2 European, 1 Argentinean and 1 Taiwanese liverworts and 2 Japanese mosses and their biological activity are discussed. The chemosystematics of some liverworts as well as the chemical relationship between liverworts and mosses, and bryophytes and ferns are also discussed.

Bibenzyls↗
PubMed1994

The phytochemistry of the Myoporaceae.

The secondary metabolites isolated from members of the Myoporaceae are reviewed. More than 200 compounds, whose structures have been elucidated, are listed together with their source in the Appendix.

Carbohydrate Sequence↗
PubMed2002

Integration of ethnobotany and phytochemistry. dream or reality?

The major challenge of this paper comprises an attempt to compare the wealth of folk-information based on "traditional knowledge" with the efficacy of a chemo-biological background based on scientific knowledge. Surprisingly, correlations between plant uses (as food and medicine) and evolutionary status according to morphology (as assigned by Sporne indices) and metabolism (as assigned by diversity of phytochemicals) obey strikingly uniform systematic and evolutionary trends. The resulting patterns suggest a dynamic chemical mechanism for the bioactivity in plants regulated by the antagonistic gallate/caffeate pair. This finding is an important step toward the construction of a coherent chemo-biological language by a dynamic holistic quantitative methodology, one of the most potent prospects for understanding the functioning of nature.

Biological Evolution↗
PubMed2003

Plant metabolomics: large-scale phytochemistry in the functional genomics era.

Metabolomics or the large-scale phytochemical analysis of plants is reviewed in relation to functional genomics and systems biology. A historical account of the introduction and evolution of metabolite profiling into today's modern comprehensive metabolomics approach is provided. Many of the technologies used in metabolomics, including optical spectroscopy, nuclear magnetic resonance, and mass spectrometry are surveyed. The critical role of bioinformatics and various methods of data visualization are summarized and the future role of metabolomics in plant science assessed.

Computational Biology↗
PubMed2003

Phytochemistry of the mopane, Colophospermum mopane.

The polyphenolic pool of the heartwood of the mopane, Colophospermum mopane Kirk ex J. Leonard, exhibits extreme diversity and complexity. It comprises a variety of monomeric flavonoids, e.g. flavan-3-ols, flavan-3,4-diols including the mopanols and peltogynols, flavonols, dimeric proanthocyanidins, e.g. proguibourtinidins, profisetinidins, promopanidins, propeltogynidins, and a variety of profisetinidin-type triflavanoids. The di- and tri-meric proanthocyanidins are accompanied by several functionalized tetrahydropyrano- and hexahydrodipyrano-chromenes (phlobatannins) that originate from the bi- and tri-flavanoids, respectively, via rearrangement of the pyran heterocycle(s). Owing to the predominance of the 5-deoxy (A-ring) flavan-3-ols, the chain terminating moieties in the biosynthesis of oligo- and poly-meric proanthocyanidins, the di- and tri-meric analogs also exhibit diversity as far as interflavanyl bonding positions are concerned. Such heterogeneity results from the reduced nucleophilicity of the A-rings of 5-deoxy flavan-3-ols, compared to the A-rings of the 5-oxy analogs (catechins), hence permitting alternative centers to participate in proanthocyanidin formation. Biomimetic-type syntheses were extensively utilized to unequivocally establish constitution and absolute stereochemistry of both the conventional and pyran ring rearranged-type di- and tri-meric compounds. Comprehension of the intricate mechanistic and stereochemical course of the pyran ring rearrangement reactions also contributed significantly to unambiguous structure elucidations. The aerial parts of the mopane are rich in essential oils that comprise mainly alpha-pinene and limonene, which are presumably responsible for the strong turpentine odor of the pods. The leaves also contain significant concentrations of beta-sitosterol and stigmasterol which are apparently the source of sterols in various organs of the mopane moth, Gonimbrasia belina. Three diterpenes, dihydrogrindelic acid, labd-13E-en-15-oate and dihydrogrindelaldehyde are present in the bark and seeds, the latter compound exhibiting significant cytotoxicity against a human breast cancer cell line.

Antineoplastic Agents↗
PubMed2000

Ethnopharmacology, phytochemistry and pharmacology: a successful combination in the study of Croton cajucara.

Phytochemical and pharmacological studies of Croton cajucara were oriented by traditional medicine. The stem bark of the mature plant is a rich source of clerodane-type diterpenes: trans-dehydrocrotonin (DCTN), trans-crotonin (CTN), cis-cajucarin B, cajucarin A, cajucarinolide and two novel clerodanes, trans-cajucarin B and sacacarin. In young (18-month-old) plants, the triterpene acetyl aleuritolic acid (AAA) was the major stem bark component and in these the diterpene DCTN was not present. The highest concentration of DCTN (1.4% of dry bark) was detected in 4-6 year-old plants, while 3-year-old plants contained only 0.26% of this diterpene. Three steroids (beta-sitosterol, stigmasterol and sitosterol-3-O-beta-glucoside), two flavonoids (kaempferol 3,4', 7-trimethyl ether and 3,7-dimethyl ether) and one diterpene (cajucarinolide) were isolated from the leaves of this Croton. The main pharmacological activity was correlated with DCTN. This clerodane produced anti-inflammatory and antinociceptive effects and a significant hypoglycemia in alloxan-induced diabetic rats. The compound also reduced the index of gastric lesions induced by restraint-in-cold. Dose-related DCTN and CTN inhibited in vivo the basal acid secretion in pylorus-ligature rats and oxyntic glands isolated from rabbit gastric mucosa, DCTN, CTN or AAA decreased in vitro uptake basal acid secretion induced by histamine and measured with the 14C-aminopyrine uptake method. Uniquely DCTN inhibited 14C-AP uptake induced by bethanechol. The terpenoids, DCTN and AAA, and the chloroform extract of 6-month-old plants reduced gastrointestinal transit in mice. The effects of DCTN and CTN on the survival of mice bearing Sarcoma 180 and Ehrlich carcinoma ascitic tumors, on the proliferation of cultured cells and TNFalpha were determined. DCTN was also evaluated for a possible antioestrogenic activity using the immature rat as a model system for bioassay of oestrogen and for an anti-implantation effect in regularly cycling rats. The biological experiments, using the plant extracts and the terpenoids DCTN, CTN and AAA, are herein discussed.

Animals↗
PubMed2006

Phytochemistry and antifungal properties of the newly discovered tree Pleodendron costaricense.

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.

Allyl Compounds↗
PubMedDate not supplied

Chemistry of acronycine IV. Minor constituents of acronine and the phytochemistry of the genus Acronychia.

In the course of isolating acronycine (1) from an alkaloid fraction of the bark of Acronychia baueri (Rutaceae), five alkaloids, 1,2,3-trimethoxy-10-methyl-acridone (9), 1,3,4-trimethoxy-10-methyl-acridone (10), des-N-methyl acronycine (14), normelicopine (5), and noracronycine (2), were isolated. Four of the isolates are new to the genus, and phytochemical analysis of the genus Acronychia is presented.

Alkaloids↗
PubMed2001

Effects of genotype, nutrient availability, and defoliation on aspen phytochemistry and insect performance.

Genetic and environmental variability, and their interactions, influence phytochemical composition and, in turn, herbivore performance. We evaluated the independent and interactive effects of plant genotype, nutrient availability, and defoliation on the foliar chemistry of quaking aspen (Populus tremuloides) and consequences for performance of gypsy moths (Lymantria dispar). Saplings of four genotypes were grown under two conditions of nutrient availability and subjected to three levels of artificial defoliation. Concentrations of all secondary and primary metabolites evaluated responded to at least one or more of the experimental treatments. Of the secondary metabolites, phenolic glycosides were affected strongly by genotype, less so by nutrient availability, and not induced by defoliation. Condensed tannins were strongly dependent upon genotype, soil nutrient availability, and their interaction, and, in contrast to phenolic glycosides, were induced by artificial defoliation. Of the primary metabolites, foliar nitrogen was affected by genotype and soil nutrient availability. Starch concentrations were affected by genotype, nutrient availability, defoliation and interactions among these factors. Foliar water content responded to genotype, nutrient availability, and defoliation, and the effect of nutrient availability depended on genotype. Herbivore performance on these plants was strongly influenced by plant genotype and soil nutrient availability, but much less so by defoliation. Although several of the compound types (condensed tannins, starch, and water) responded to defoliation, quantitative variation in these compounds did not contribute to substantive changes in herbivore performance. Rather, the primary source of variation in insect performance was due to plant genotype (phenolic glycoside levels), while nutrient availability (foliar nitrogen levels) was of secondary importance. These results suggest that genetic variation in aspen plays a major role in determining patterns of insect performance, whereas environmental variation, such as was tested, here is of negligible importance.

Animals↗