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Terpenoids

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (30 November 2011) | Viewed by 167380

Special Issue Editor

Prof. Dr. Alejandro Fernandez Barrero

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Guest Editor
Department of Organic Chemistry and Institute of Biotechnology, Faculty of Sciences, University of Granada, Avda de Fuentenueva s/n,18071 Granada, Spain
Interests: natural products chemistry; synthesis of bioactive terpenoids; radical strategies; biomimetic cyclizations; new quirons as starting materials; terpenoids from fungi

Special Issue Information

Dear Colleagues,

Terpenoids, including more than 35.000 well defined molecules, probably constitutes the natural products family with the greater structural diversity. Numerous of these compounds possess well known applications as drugs, cosmetics, perfumes, flavours, insecticides, herbicides, phyto-hormones and many others. In recent years a number of advances in terpenoid research have led for example to the discovery of a second biosynthetic pathway, namely methyl-erythritol phosphate pathway (MEP), usually present in bacteria and plants. The knowledge of the structure of both, enzymes and genes involved in this pathway and the detailed mechanism of the specific steps are opening the possibility to develop new selective and efficient molecules with bioactivities against those pathogen micro-organisms responsible of the resistant strains from tuberculosis and malaria. Furthermore we have acquired better understanding of the structure and way of working of the key-enzymes, prenyltransferases and terpenecyclases, which are the principal motive of the uncommon molecular diversity in terpenoids. All this is provoking, among other things a develop of new research lines in order to optimize the biotechnological production of bioactive terpenes through genetic engineering from plants and microorganisms.

Moreover advances in Organic Synthesis, including new biomimetic strategies and the use of natural quirons, are reaching an important role in the development of more efficient syntheses easily scalable to industrial levels. Thus, is remarkable the appearance at antitumor medicament worldwide market of diverse diterpene taxol derivatives thanks to the sustainable farming of Taxus baccata, plant used as natural source for the terpenic backbone in combination with a semisynthetic process.

This special issue attempts to be a meeting point and a discussion forum for the interchange of experiences in terpenoid chemistry. Contributions about all the different steps involved in this field of research: extraction processes; isolation procedures; structural elucidation; direct identification from extracts by chromatographic or spectroscopic techniques; derreplication by HPLC combined with Mass Spectrometry or NMR; biotransformations; partial synthesis or total synthesis will be well received.

Prof. Dr. Alejandro Fernandez Barrero
Guest Editor

Keywords

  • isoprenoids
  • monoterpenes
  • sesquiterpenes
  • diterpenes
  • sesterterpenes
  • triterpenes
  • carotenes
  • meroterpenes
  • structural elucidation
  • terpenecyclases
  • biosynthesis
  • biotransformation
  • biotechnology
  • total synthesis
  • bioactivity
  • allelophaty
  • pesticides
  • drugs

Published Papers (17 papers)

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Research

Jump to: Review

355 KiB  
Article
Self-Organizing Maps of Molecular Descriptors for Sesquiterpene Lactones and Their Application to the Chemotaxonomy of the Asteraceae Family
by Marcus T. Scotti, Vicente Emerenciano, Marcelo J. P. Ferreira, Luciana Scotti, Ricardo Stefani, Marcelo S. Da Silva and Francisco Jaime B. Mendonça Junior
Molecules 2012, 17(4), 4684-4702; https://doi.org/10.3390/molecules17044684 - 20 Apr 2012
Cited by 37 | Viewed by 9266
Abstract
The Asteraceae, one of the largest families among angiosperms, is chemically characterised by the production of sesquiterpene lactones (SLs). A total of 1,111 SLs, which were extracted from 658 species, 161 genera, 63 subtribes and 15 tribes of Asteraceae, were represented and registered [...] Read more.
The Asteraceae, one of the largest families among angiosperms, is chemically characterised by the production of sesquiterpene lactones (SLs). A total of 1,111 SLs, which were extracted from 658 species, 161 genera, 63 subtribes and 15 tribes of Asteraceae, were represented and registered in two dimensions in the SISTEMATX, an in-house software system, and were associated with their botanical sources. The respective 11 block of descriptors: Constitutional, Functional groups, BCUT, Atom-centred, 2D autocorrelations, Topological, Geometrical, RDF, 3D-MoRSE, GETAWAY and WHIM were used as input data to separate the botanical occurrences through self-organising maps. Maps that were generated with each descriptor divided the Asteraceae tribes, with total index values between 66.7% and 83.6%. The analysis of the results shows evident similarities among the Heliantheae, Helenieae and Eupatorieae tribes as well as between the Anthemideae and Inuleae tribes. Those observations are in agreement with systematic classifications that were proposed by Bremer, which use mainly morphological and molecular data, therefore chemical markers partially corroborate with these classifications. The results demonstrate that the atom-centred and RDF descriptors can be used as a tool for taxonomic classification in low hierarchical levels, such as tribes. Descriptors obtained through fragments or by the two-dimensional representation of the SL structures were sufficient to obtain significant results, and better results were not achieved by using descriptors derived from three-dimensional representations of SLs. Such models based on physico-chemical properties can project new design SLs, similar structures from literature or even unreported structures in two-dimensional chemical space. Therefore, the generated SOMs can predict the most probable tribe where a biologically active molecule can be found according Bremer classification. Full article
(This article belongs to the Special Issue Terpenoids)
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321 KiB  
Article
Chemical and Antimicrobial Evaluation of Supercritical and Conventional Sideritis scardica Griseb., Lamiaceae Extracts
by Vanja Tadić, Dragica Bojović, Ivana Arsić, Sofija Đorđević, Ksenija Aksentijevic, Marko Stamenić and Slobodan Janković
Molecules 2012, 17(3), 2683-2703; https://doi.org/10.3390/molecules17032683 - 05 Mar 2012
Cited by 47 | Viewed by 7593
Abstract
Sideritis scardica Griseb., Lamiaceae (ironwort, mountain tea), an endemic plant of the Balkan Peninsula, has been used in traditional medicine in the treatment of antimicrobial infections, gastrointestinal complaints, inflammation and rheumatic disorders. This study reports a comparison between conventional (hydrodistillation HD and solvent [...] Read more.
Sideritis scardica Griseb., Lamiaceae (ironwort, mountain tea), an endemic plant of the Balkan Peninsula, has been used in traditional medicine in the treatment of antimicrobial infections, gastrointestinal complaints, inflammation and rheumatic disorders. This study reports a comparison between conventional (hydrodistillation HD and solvent extraction SE) and alternative (supercritical carbon dioxide SC CO2) extraction methods regarding the qualitative and quantitative composition of the obtained extracts as analyzed by GC and GC-MS techniques and their anitimicrobial activity. Different types of extracts were tested, the essential oil EO obtained by HD, EO-CO2 and AO-CO2 obtained by SC CO2 at different preasures 10 and 30 MPa, at 40 °C, respectively, and the fractions A, B, C and D obtained by successive solvent extraction (SE) A: ethanol, B: diethyl ether, C: ethyl acetate and D: n-butanol). While EO was characterized by the presence of the high percentage of oxygenated monoterpenes and sesquiterpenes (30.01 and 25.54%, respectively), the rest of the investigated samples were the most abundant in fatty acids and their esters and diterpenes (from 16.72 to 71.07% for fatty acids and their esters, and from 23.30 to 72.76%, for diterpenes). Microbial susceptibility tests revealed the strong to moderate activity of all investigated extracts against the tested microorganisms (MIC from 40 to 2,560 μg/mL). Although differences in the chemical compositions determined by GC and GC-MS analysis were established, the displayed antimicrobial activity was similar for the all investigated extracts. Full article
(This article belongs to the Special Issue Terpenoids)
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503 KiB  
Article
Structure-Odor Relationships of α­Santalol Derivatives with Modified Side Chains
by Toshio Hasegawa, Hiroaki Izumi, Yuji Tajima and Hideo Yamada
Molecules 2012, 17(2), 2259-2270; https://doi.org/10.3390/molecules17022259 - 22 Feb 2012
Cited by 11 | Viewed by 6667 | Correction
Abstract
(Z)-α-Santalol, which has a unique woody odor, is a main constituent of sandalwood essential oil. We investigated the structure-odor relationship of (Z)-α-santalol and its derivatives, focusing on the relationship between the structure of the side chain and the odor [...] Read more.
(Z)-α-Santalol, which has a unique woody odor, is a main constituent of sandalwood essential oil. We investigated the structure-odor relationship of (Z)-α-santalol and its derivatives, focusing on the relationship between the structure of the side chain and the odor of the compounds. Various α-santalol derivatives (aldehydes, formates, and acetates) were synthesized from (Z)- and (E)-α-santalol, which were prepared from (+)-3-bromocamphor through modifications of a reported synthetic route. The Z- and E-isomers of α-santalols have different double-bond configurations in the side chain. Analogues with saturated side chains were also prepared from the corresponding α-santalols, and the odors of the all the prepared compounds were evaluated. We found that the odors of the Z-isomers (woody) were similar to those of the corresponding saturated compounds, but clearly different from the odors of the corresponding E-isomers (odorless, fresh, or fatty). These results indicate that the relative configuration of the side chain with respect to the santalane frame plays an important role in the odor of α-santalol. E-configuration in the side chain eliminates the woody odor character of α-santalol and its examined derivatives, whereas the Z-configuration or saturation of the carbon side chain does not. Full article
(This article belongs to the Special Issue Terpenoids)
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187 KiB  
Article
The Incubation of 13a,17-Dihydroxystemodane with Cephalosporium aphidicola
by Braulio M. Fraga, Ricardo Guillermo, Melchor G. Hernández, María C. Chamy and Juan A. Garbarino
Molecules 2012, 17(2), 1744-1750; https://doi.org/10.3390/molecules17021744 - 09 Feb 2012
Cited by 5 | Viewed by 5174
Abstract
The biotransformation of 13a,17-dihydroxystemodane (3) with the fungus Cephalosporium aphidicola afforded 13a,17,18-trihydroxystemodane (4), 3b,13a,17-tri-hydroxystemodane (5), 13a,17-dihydroxy-stemodan-18-oic acid (6), 3b,11β,13a,17-tetra-hydroxystemodane (7), 11β,13a,17,18-tetrahydroxystemodane (8) and 3b,13a,17,18-tetra-hydroxystemodane (9). The hydroxylation at C-18 [...] Read more.
The biotransformation of 13a,17-dihydroxystemodane (3) with the fungus Cephalosporium aphidicola afforded 13a,17,18-trihydroxystemodane (4), 3b,13a,17-tri-hydroxystemodane (5), 13a,17-dihydroxy-stemodan-18-oic acid (6), 3b,11β,13a,17-tetra-hydroxystemodane (7), 11β,13a,17,18-tetrahydroxystemodane (8) and 3b,13a,17,18-tetra-hydroxystemodane (9). The hydroxylation at C-18 of the substrate points to a biosynthetically-directed transformation, because aphidicolin (2) is hydroxylated at this carbon. However, the C-3(b) and C-11(b) hydroxylations seem to indicate a xenobiotic biotransformation. Full article
(This article belongs to the Special Issue Terpenoids)
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350 KiB  
Article
Ergosterol-Induced Sesquiterpenoid Synthesis in Tobacco Cells
by Fidele Tugizimana, Paul A. Steenkamp, Lizelle A. Piater and Ian A. Dubery
Molecules 2012, 17(2), 1698-1715; https://doi.org/10.3390/molecules17021698 - 09 Feb 2012
Cited by 26 | Viewed by 7190
Abstract
Plants have the ability to continuously respond to microbial signals in their environment. One of these stimuli is a steroid from fungal membranes, ergosterol, which does not occur in plants, but acts as a pathogen-associated molecular pattern molecule to trigger defence mechanisms. Here [...] Read more.
Plants have the ability to continuously respond to microbial signals in their environment. One of these stimuli is a steroid from fungal membranes, ergosterol, which does not occur in plants, but acts as a pathogen-associated molecular pattern molecule to trigger defence mechanisms. Here we investigated the effect of ergosterol on the secondary metabolites in tobacco (Nicotiana tabacum) cells by profiling the induced sesquiterpenoids. Suspensions of tobacco cells were treated with different concentrations (0–1,000 nM) of ergosterol and incubated for different time periods (0–24 h). Metabolites were extracted with a selective dispersive liquid-liquid micro-extraction method. Thin layer chromatography was used as a screening method for identification of sesquiterpenoids in tobacco extracts. Liquid chromatography coupled to mass spectrometry was used for quantitative and qualitative analyses. The results showed that ergosterol triggered differential changes in the metabolome of tobacco cells, leading to variation in the biosynthesis of secondary metabolites. Metabolomic analysis through principal component analysis-scores plots revealed clusters of sample replicates for ergosterol treatments of 0, 50, 150, 300 and 1,000 nM and time-dependent variation at 0, 6, 12, 18 and 24 h. Five bicyclic sesquiterpenoid phytoalexins, capsidiol, lubimin, rishitin, solavetivone and phytuberin, were identified as being ergosterol-induced, contributing to the altered metabolome. Full article
(This article belongs to the Special Issue Terpenoids)
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262 KiB  
Article
Four Eremophil-9-en-8-one Derivatives from Cremanthodium stenactinium Samples Collected in China
by Yoshinori Saito, Mayu Ichihara, Yasuko Okamoto, Xun Gong, Chiaki Kuroda and Motoo Tori
Molecules 2011, 16(12), 10645-10652; https://doi.org/10.3390/molecules161210645 - 19 Dec 2011
Cited by 17 | Viewed by 4769
Abstract
Two samples of Cremanthodium stenactinium (Asteraceae) were collected in Sichuan Province, China. From the ethyl acetate extracts of the roots, three new eremophilane-type sesquiterpenoids and one new trinoreremophilane compound were isolated, together with other known eremophilanes. Their structures were determined based on the [...] Read more.
Two samples of Cremanthodium stenactinium (Asteraceae) were collected in Sichuan Province, China. From the ethyl acetate extracts of the roots, three new eremophilane-type sesquiterpenoids and one new trinoreremophilane compound were isolated, together with other known eremophilanes. Their structures were determined based on the spectroscopic data. This is the first report of isolation of eremophilane-type compounds from the genus Cremanthodium. Full article
(This article belongs to the Special Issue Terpenoids)
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235 KiB  
Article
Biotransformation of (1S)-2-Carene and (1S)-3-Carene by Picea abies Suspension Culture
by Marcela Dvorakova, Irena Valterova, David Saman and Tomas Vanek
Molecules 2011, 16(12), 10541-10555; https://doi.org/10.3390/molecules161210541 - 19 Dec 2011
Cited by 12 | Viewed by 5659
Abstract
Biotransformation of (1S)-2-carene and (1S)-3-carene by Picea abies suspension culture led to the formation of oxygenated products. (1S)-2-Carene was transformed slowly and the final product was identified as (1S)-2-caren-4-one. On the other hand, the transformation [...] Read more.
Biotransformation of (1S)-2-carene and (1S)-3-carene by Picea abies suspension culture led to the formation of oxygenated products. (1S)-2-Carene was transformed slowly and the final product was identified as (1S)-2-caren-4-one. On the other hand, the transformation of (1S)-3-carene was rapid and finally led to the formation of (1S)-3-caren-5-one and (1S)-2-caren-4-one as equally abundant major products. The time-course of the reaction indicates that some products abundant at the beginning of the reaction (e.g. (1S,3S,4R)-3,4-epoxycarane and (1R)-p-mentha-1(7),2-dien-8-ol) were consumed by a subsequent transformations. Thus, a precise selection of the biotransformation time may be used for a production of specific compounds. Full article
(This article belongs to the Special Issue Terpenoids)
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207 KiB  
Article
Terpenoids and Bibenzyls from Three Argentine Liverworts
by Fumihiro Nagashima and Yoshinori Asakawa
Molecules 2011, 16(12), 10471-10478; https://doi.org/10.3390/molecules161210471 - 16 Dec 2011
Cited by 12 | Viewed by 5196
Abstract
A new rosane diterpenoid, 3a-hydroxy-5,15-rosadien-11-one (3), was isolated, together with a known rosane diterpenoid, 5,15-rosadiene-3,11-dione (4), and an aromadendrane sesquiterpenoid, ent-cyclocolorenone (5), from the Et2O extract of an unidentified Argentine liverwort Anastrophyllum species. Moreover, [...] Read more.
A new rosane diterpenoid, 3a-hydroxy-5,15-rosadien-11-one (3), was isolated, together with a known rosane diterpenoid, 5,15-rosadiene-3,11-dione (4), and an aromadendrane sesquiterpenoid, ent-cyclocolorenone (5), from the Et2O extract of an unidentified Argentine liverwort Anastrophyllum species. Moreover, four known sesquiterpene lactones 6–9 and two known bibenzyls 10, 11 were isolated from the Et2O extracts of Argentine Frullania brasiliensis and Radula voluta, respectively. The structures of compounds 3–11 were determined by the use of NMR techniques. Full article
(This article belongs to the Special Issue Terpenoids)
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464 KiB  
Article
Synthesis of ent-Kaurane Diterpene Monoglycosides
by Venkata Sai Prakash Chaturvedula, Josef Klucik, Mani Upreti and Indra Prakash
Molecules 2011, 16(10), 8402-8409; https://doi.org/10.3390/molecules16108402 - 03 Oct 2011
Cited by 23 | Viewed by 7794
Abstract
Synthesis of two ent-kaurane diterpene glycosides, steviol 19-O-β-D-glucopyranosiduronic acid (steviol glucuronide, 5), and 13-hydroxy ent-kaur-16-en-19-oic acid-β-D-glucopyranosyl ester (7) has been achieved from a common starting material, steviol, using phase transfer catalyst. Also, synthesis of an additional 17-nor-ent [...] Read more.
Synthesis of two ent-kaurane diterpene glycosides, steviol 19-O-β-D-glucopyranosiduronic acid (steviol glucuronide, 5), and 13-hydroxy ent-kaur-16-en-19-oic acid-β-D-glucopyranosyl ester (7) has been achieved from a common starting material, steviol, using phase transfer catalyst. Also, synthesis of an additional 17-nor-ent-kaurane glycoside, namely 13-methyl-16-oxo-17-nor-ent-kauran-19-oic acid-β-D-glucopyranosyl ester (10) was performed using the starting material isosteviol and similar synthetic methodology. Synthesis of all three steviol glycosides was performed using straightforward chemistry and their structures were characterized on the basis of 1D and 2D NMR as well as mass spectral (MS) data. Full article
(This article belongs to the Special Issue Terpenoids)
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392 KiB  
Article
Antiphytoviral Activity of Sesquiterpene-Rich Essential Oils from Four Croatian Teucrium Species
by Nada Bezić, Elma Vuko, Valerija Dunkić, Mirko Ruščić, Ivica Blažević and Franko Burčul
Molecules 2011, 16(9), 8119-8129; https://doi.org/10.3390/molecules16098119 - 21 Sep 2011
Cited by 51 | Viewed by 7552
Abstract
The purpose of this study was to compare the essential oil profiles of four Croatian Teucrium species (Lamiaceae), as determined by GC and GC/MS, with their antiphytoviral efficiency. A phytochemical analysis showed that T. polium, T. flavum, T. montanum and T. [...] Read more.
The purpose of this study was to compare the essential oil profiles of four Croatian Teucrium species (Lamiaceae), as determined by GC and GC/MS, with their antiphytoviral efficiency. A phytochemical analysis showed that T. polium, T. flavum, T. montanum and T. chamaedrys are characterized by similar essential oil compositions. The investigated oils are characterized by a high proportion of the sesquiterpene hydrocarbons β-caryophyllene (7.1–52.0%) and germacrene D (8.7–17.0%). Other important components were β-pinene from T. montanum and α-pinene from T. flavum. The investigated essential oils were proved to reduce lesion number in the local host Chenopodium quinoa Willd. infected with Cucumber Mosaic Virus (CMV), with reductions of 41.4%, 22.9%, 44.3% and 25.7%, respectively. Full article
(This article belongs to the Special Issue Terpenoids)
436 KiB  
Article
A Short Synthesis of Bisabolane Sesquiterpenes
by Zhen-Ting Du, Shuai Zheng, Gang Chen and Dong Lv
Molecules 2011, 16(9), 8053-8061; https://doi.org/10.3390/molecules16098053 - 19 Sep 2011
Cited by 14 | Viewed by 7071
Abstract
A facile total synthesis of three members of the bisabolane sesquiterpene family, namely (±)-curcumene, (±)-xanthorrhizol and (±)-curcuhydroquinone had been achieved in high overall yield. The synthesis used bromobenzene derivatives as starting materials. The halogen-lithium exchange followed by addition of isoprenylacetone and reduction of [...] Read more.
A facile total synthesis of three members of the bisabolane sesquiterpene family, namely (±)-curcumene, (±)-xanthorrhizol and (±)-curcuhydroquinone had been achieved in high overall yield. The synthesis used bromobenzene derivatives as starting materials. The halogen-lithium exchange followed by addition of isoprenylacetone and reduction of the obtained carbinols are the key steps of the synthetic pathway. This synthetic approach provides a new route to the bisabolane sesquiterpenes. Full article
(This article belongs to the Special Issue Terpenoids)
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Review

Jump to: Research

275 KiB  
Review
Extraction of Volatile Oil from Aromatic Plants with Supercritical Carbon Dioxide: Experiments and Modeling
by Jose P. Coelho, Ana F. Cristino, Patrícia G. Matos, Amélia P. Rauter, Beatriz P. Nobre, Rui L. Mendes, João G. Barroso, Ana Mainar, Jose S. Urieta, João M. N. A. Fareleira, Helena Sovová and António F. Palavra
Molecules 2012, 17(9), 10550-10573; https://doi.org/10.3390/molecules170910550 - 05 Sep 2012
Cited by 46 | Viewed by 8397
Abstract
An overview of the studies carried out in our laboratories on supercritical fluid extraction (SFE) of volatile oils from seven aromatic plants: pennyroyal (Mentha pulegium L.), fennel seeds (Foeniculum vulgare Mill.), coriander (Coriandrum sativum L.), savory (Satureja fruticosa Béguinot [...] Read more.
An overview of the studies carried out in our laboratories on supercritical fluid extraction (SFE) of volatile oils from seven aromatic plants: pennyroyal (Mentha pulegium L.), fennel seeds (Foeniculum vulgare Mill.), coriander (Coriandrum sativum L.), savory (Satureja fruticosa Béguinot), winter savory (Satureja montana L.), cotton lavender (Santolina chamaecyparisus) and thyme (Thymus vulgaris), is presented. A flow apparatus with a 1 L extractor and two 0.27 L separators was built to perform studies at temperatures ranging from 298 to 353 K and pressures up to 30.0 MPa. The best compromise between yield and composition compared with hydrodistillation (HD) was achieved selecting the optimum experimental conditions of extraction and fractionation. The major differences between HD and SFE oils is the presence of a small percentage of cuticular waxes and the relative amount of thymoquinone, an oxygenated monoterpene with important biological properties, which is present in the oils from thyme and winter savory. On the other hand, the modeling of our data on supercritical extraction of volatile oil from pennyroyal is discussed using Sovová’s models. These models have been applied successfully to the other volatile oil extractions. Furthermore, other experimental studies involving supercritical CO2 carried out in our laboratories are also mentioned. Full article
(This article belongs to the Special Issue Terpenoids)
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289 KiB  
Review
Chemistry and Biological Activities of Terpenoids from Copaiba (Copaifera spp.) Oleoresins
by Lidiam Maia Leandro, Fabiano De Sousa Vargas, Paula Cristina Souza Barbosa, Jamilly Kelly Oliveira Neves, José Alexsandro Da Silva and Valdir Florêncio Da Veiga-Junior
Molecules 2012, 17(4), 3866-3889; https://doi.org/10.3390/molecules17043866 - 30 Mar 2012
Cited by 180 | Viewed by 25938
Abstract
Copaiba oleoresins are exuded from the trunks of trees of the Copaifera species (Leguminosae-Caesalpinoideae). This oleoresin is a solution of diterpenoids, especially, mono- and di-acids, solubilized by sesquiterpene hydrocarbons. The sesquiterpenes and diterpenes (labdane, clerodane and kaurane skeletons) are different for each Copaifera [...] Read more.
Copaiba oleoresins are exuded from the trunks of trees of the Copaifera species (Leguminosae-Caesalpinoideae). This oleoresin is a solution of diterpenoids, especially, mono- and di-acids, solubilized by sesquiterpene hydrocarbons. The sesquiterpenes and diterpenes (labdane, clerodane and kaurane skeletons) are different for each Copaifera species and have been linked to several reported biological activities, ranging from anti-tumoral to embriotoxic effects. This review presents all the substances already described in this oleoresin, together with structures and activities of its main terpenoids. Full article
(This article belongs to the Special Issue Terpenoids)
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646 KiB  
Review
Terpenoids as Potential Anti-Alzheimer’s Disease Therapeutics
by Ki-Yeol Yoo and So-Young Park
Molecules 2012, 17(3), 3524-3538; https://doi.org/10.3390/molecules17033524 - 19 Mar 2012
Cited by 109 | Viewed by 15189
Abstract
Alzheimer’s disease (AD) is one of the most well-known neurodegenerative diseases and explains 50–60% of dementia in patients. The prevalence rate of AD is positively correlated with age and AD affects ≥ 40% of those over 85 years old. The major AD therapeutics [...] Read more.
Alzheimer’s disease (AD) is one of the most well-known neurodegenerative diseases and explains 50–60% of dementia in patients. The prevalence rate of AD is positively correlated with age and AD affects ≥ 40% of those over 85 years old. The major AD therapeutics available on the market are acetylcholinesterase inhibitors, such as tacrine and donepezil. New therapeutic agents that can block the disease-inducing mechanisms are essential. Diverse efforts have been made to discover anti-AD agents from natural sources. In this review article, we describe some representative terpenoids such as ginsenosides, gingkolides, and canabinoids as potential anti-AD agents. These compounds exhibit promising in vitro and in vivo biological activities, but are still waiting clinical trials. Additionally, we also discuss some terpenoids including cornel iridoid glycoside, oleanolic acid, tenuifolin, cryptotanshinone, and ursolic acid, which are under investigation for their in vitro and in vivo animal studies. Full article
(This article belongs to the Special Issue Terpenoids)
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248 KiB  
Review
The Artemisia L. Genus: A Review of Bioactive Essential Oils
by María José Abad, Luis Miguel Bedoya, Luis Apaza and Paulina Bermejo
Molecules 2012, 17(3), 2542-2566; https://doi.org/10.3390/molecules17032542 - 02 Mar 2012
Cited by 440 | Viewed by 24675
Abstract
Numerous members of the Anthemideae tribe are important as cut flowers and ornamental crops, as well as being medicinal and aromatic plants, many of which produce essential oils used in folk and modern medicine and in the cosmetics and pharmaceutical industry. Essential oils [...] Read more.
Numerous members of the Anthemideae tribe are important as cut flowers and ornamental crops, as well as being medicinal and aromatic plants, many of which produce essential oils used in folk and modern medicine and in the cosmetics and pharmaceutical industry. Essential oils generally have a broad spectrum of bioactivity, owing to the presence of several active ingredients that work through various modes of action. Due to their mode of extraction, mostly by distillation from aromatic plants, they contain a variety of volatile molecules such as terpenes, phenol-derived aromatic and aliphatic components. The large genus Artemisia L., from the tribe Anthemideae, comprises important medicinal plants which are currently the subject of phytochemical attention due to their biological and chemical diversity. Artemisia species, widespread throughout the world, are one of the most popular plants in Chinese traditional preparations and are frequently used for the treatment of diseases such as malaria, hepatitis, cancer, inflammation and infections by fungi, bacteria and viruses. Extensive studies of the chemical components of Artemisia have led to the identification of many compounds as well as essentials oils. This review summarizes some of the main reports on the chemistry and anti-infective activities of Artemisia. Li. essential oils from the data in the recent literature (2000–2011). Full article
(This article belongs to the Special Issue Terpenoids)
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569 KiB  
Review
Communic Acids: Occurrence, Properties and Use as Chirons for the Synthesis of Bioactive Compounds
by Alejandro F. Barrero, M. Mar Herrador, Pilar Arteaga, Jesús F. Arteaga and Alejandro F. Arteaga
Molecules 2012, 17(2), 1448-1467; https://doi.org/10.3390/molecules17021448 - 06 Feb 2012
Cited by 28 | Viewed by 9883
Abstract
Communic acids are diterpenes with labdane skeletons found in many plant species, mainly conifers, predominating in the genus Juniperus (fam. Cupresaceae). In this review we briefly describe their distribution and different biological activities (anti- bacterial, antitumoral, hypolipidemic, relaxing smooth muscle, etc.). [...] Read more.
Communic acids are diterpenes with labdane skeletons found in many plant species, mainly conifers, predominating in the genus Juniperus (fam. Cupresaceae). In this review we briefly describe their distribution and different biological activities (anti- bacterial, antitumoral, hypolipidemic, relaxing smooth muscle, etc.). This paper also includes a detailed explanation of their use as chiral building blocks for the synthesis of bioactive natural products. Among other uses, communic acids have proven useful as chirons for the synthesis of quassinoids (formal), abietane antioxidants, ambrox and other perfume fixatives, podolactone herbicides, etc., featuring shorter and more efficient processes. Full article
(This article belongs to the Special Issue Terpenoids)
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Review
Terpenoids from Endophytic Fungi
by Jucimar Jorgeane de Souza, Ivo José Curcino Vieira, Edson Rodrigues-Filho and Raimundo Braz-Filho
Molecules 2011, 16(12), 10604-10618; https://doi.org/10.3390/molecules161210604 - 19 Dec 2011
Cited by 58 | Viewed by 8148
Abstract
This work reviews the production of terpenoids by endophytic fungi and their biological activities, in period of 2006 to 2010. Sixty five sesquiterpenes, 45 diterpenes, five meroterpenes and 12 other terpenes, amounting to 127 terpenoids were isolated from endophytic fungi. Full article
(This article belongs to the Special Issue Terpenoids)
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