109 results on '"OLEACEAE"'
Search Results
2. The genus Fraxinus L. (Oleaceae): A review of botany, traditional and modern applications, phytochemistry, and bioactivity.
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Guo J, Zhang SS, Gao J, Guo Y, Ho CT, and Bai N
- Abstract
Fraxinus L., a member of the Oleaceae family with approximately 60 species worldwide, is widely distributed in the warm temperate zone of the northern hemisphere. It is not only used as a folk medicine for treating various illnesses but is also documented in medical books. The traditional Chinese medicine "Qin Pi" originated from this genus and is known for its efficacy in treating conditions such as intestinal inflammation, redness and pain in the eyes, abomination of redness and leucorrhoea, and bacterial infections. This paper aims to fill the gap in the existing literature by providing a comprehensive review and critical analysis of the Fraxinus genus plant. The discussion in this paper covers various aspects of the plant, including its botany, traditional and modern applications, phytochemistry, bioactivity, role in ecosystems, phytogenetic evolution, economic benefits, and future challenges. By synthesizing this information, the review aims to offer valuable insights for the advancement, utilization, and further research of the Fraxinus spp.. Phytochemical studies have identified a total of 281 chemical constituents in Fraxinus spp., including secoiridoids, coumarins, and flavonoids. These Fraxinus spp. plants exhibit a wide range of biological activities, such as anti-inflammatory, antioxidant, and antibacterial properties. Furthermore, this paper delves into potential research directions within the genus and addresses the challenges associated with achieving a comprehensive understanding of Fraxinus spp. This paper provides a comprehensive overview of Fraxinus spp., highlighting their bioactivity mechanism and the opportunity to facilitate the advancement of new pharmaceuticals., Competing Interests: Declaration of competing interest The authors declare that there are no competing interests or that could influence the work described in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.) more...
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- 2024
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Catalog
3. Dimeric eremophilane-type sesquiterpenoids from the peeled stems of Syringa pinnatifolia.
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Sun, Jingjing, Li, Anni, Jiao, Shungang, Liu, Changxin, Zhang, Zefeng, Chen, Hongying, Liang, Yana, Gao, Xiaoli, Cao, Lan, Bai, Changcai, and Chai, Xingyun
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CHEMICAL shift (Nuclear magnetic resonance) , *SESQUITERPENES , *ANALYTICAL chemistry , *X-ray diffraction , *DIMERS , *DATA analysis , *ETHANOL - Abstract
A continued phytochemical investigation guided by 1H NMR and LC-MS data on the ethanol extract from the peeled stems of Syringa pinnatifolia Hemsl. led to the isolation of 16 undescribed dimeric eremophilane sesquiterpenoids, namely syringenes R–Z (1 – 9) and A 1 –G 1 (10 – 16). These structures were elucidated by extensive analysis of spectroscopic data, including HRESIMS, NMR, quantum-mechanics-based computational analysis of NMR chemical shifts, and single-crystal X-ray diffraction analyses, and a concise rule for determination of relative configuration of angular methyl was proposed. The results of the cardioprotective assay demonstrated that 3 exhibits a protective effect against hypoxia-induced injuries in H9c2 cells. This effect was observed at a concentration of 10 μM, with a protective rate of 28.43 ± 11.80%. Sixteen undescribed dimeric eremophilane sesquiterpenoids were isolated from Syringa pinnatifolia. A concise rule for relative configuration of angle methyls of eremophilane dimers was proposed. [Display omitted] • Sixteen undescribed dimeric eremophilane sesquiterpenoids were isolated from Syringa pinnatifolia. • The absolute configurations were determined by analyzing its spectroscopic and single-crystal X-ray diffraction data. • A concise rule for relative configuration of angle methyls of eremophilane dimers was proposed. • Syringene T exhibits a protective effect against hypoxia-induced injuries in H9c2 cells. [ABSTRACT FROM AUTHOR] more...
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- 2024
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4. 9,9′-epoxylignans from Syringa pinnatifolia: A typical case of stereochemical assignment by a quantum chemical calculation with MAEΔΔδ parameter.
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Jiao, Shungang, Liu, Changxin, Chen, Panlong, Li, Junjun, Sun, Jingjing, Gao, Xiaoli, and Chai, Xingyun
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STEREOCHEMISTRY , *STEREOISOMERS , *NEOLIGNANS , *CHEMICAL species , *X-ray diffraction , *DATA analysis , *LIGNANS - Abstract
In the current study, twenty-two stereochemical 9,9′-epoxylignans including 19 undescribed ones were isolated from the ethanol extract of Syringa pinnatifolia in our continuing effort to understand the overall chemical spectrum of this species. These isolates were structurally elucidated by extensive spectroscopic data analysis, X-ray diffraction, modified Mosher's method, and quantum chemical calculations. Meanwhile, the utilization of 13C NMR calculation and the MAE ΔΔ δ parameter facilitated the stereochemical assignment of groups of lignan stereoisomers. The 13C NMR data were corrected by the averaged errors at each corresponding carbon position in groups of lignan stereoisomers, which improved the theoretic 13C NMR calculation. The finding of the stereochemical structures of 9,9′-epoxylignans is significant. It is helpful to determine the absolute configurations of molecules with the similar core. In addition, these lignans exhibited potential cardioprotective activities on H9c2 cardiomyocytes in vitro and presented significant antioxidant effect. Nineteen undescribed 9,9′-epoxylignans and three known ones were isolated from the stems of Syringa pinnatifolia. The utilization of 13C NMR calculation and the MAE ΔΔ δ parameter facilitated their stereochemical assignments. [Display omitted] • 21 lignans including 19 undescribed ones were isolated from Syringa pinnatifolia. • Stereochemistry was assigned by NMR calculations with MAE ΔΔδ parameter. • Systematical errors were eliminated by the averaged errors. • These lignans exhibited cadioprotective and antioxidant effects. [ABSTRACT FROM AUTHOR] more...
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- 2024
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5. Diplofuranoxin, a disubstituted dihydrofuranone, was produced together with sphaeropsidin A and epi-sphaeropsidone by Diplodia subglobosa, an emerging ash (Fraxinus excelsior L.) pathogen in Europe
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Marco Masi, Roberta Di Lecce, Umberto Calice, Benedetto Teodoro Linaldeddu, Lucia Maddau, Stefano Superchi, Antonio Evidente, Masi, Marco, Di Lecce, Roberta, Calice, Umberto, Linaldeddu, Benedetto Teodoro, Maddau, Lucia, Superchi, Stefano, and Evidente, Antonio more...
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Diplodia subglobosa ,Oleaceae ,Biological activities ,Biological activitie ,Fraxinus excelsior ,Plant Disease ,Canker and dieback ,Plant Science ,General Medicine ,Horticulture ,Invasive pathogen ,Biochemistry ,Europe ,Phytotoxin ,Ascomycota ,Fraxinus ,Botryosphaeriaceae ,Invasive pathogens ,Phytotoxins ,Diterpenes ,Diterpene ,Molecular Biology ,Plant Diseases - Abstract
An undescribed disubstituted dihydrofuranone, named diplofuranoxin, was isolated, together with the six well known metabolites sphaeropsidins A and C, epi-sphaeropsidone, mellein and cis- and trans-4-hydroxymelleins, from the fungal species Diplodia subglobosa, an emerging pathogen involved in the ash dieback aetiology in Europe. Currently, the disease represents the main threat to European ash heritage and the wood associated industry. Diplofuranoxin, was characterized essentially by NMR and HRESIMS spectra as (3Z)-3-(2,3-dihydroxybutylidene)-5-methyldihydrofuran-2(3H)-one. Its relative and absolute configuration was determined by joining NOESY NMR experiments and computational analysis of electronic circular dichroism spectrum. All the metabolites were screened for phytotoxic, antioomycetes and zootoxic activities and only sphaeropsidin A and epi-sphaeropsidone were active in two out of three bioassays performed. In addition, sphaeropsidin A completely inhibited mycelium growth of Phytophthora cambivora, whereas the inhibition rate of epi-sphaeropsidone was less than 50% at the higher concentration used. Both metabolites were inactive in the Artemia salina assay. Results obtained in this study have allowed to characterize for the first time the main metabolites produced in vitro by D. subglobosa and to increase the knowledge on the metabolic profile of Botryosphaeriaceae for a correct taxonomic classification of the strains belonging to this family. more...
- Published
- 2022
6. Chemical constituents from the fruits of Ligustrum japonicum and their inhibitory effects on T cell activation.
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Ngo, Quynh-Mai Thi, Lee, Hyun-Su, Nguyen, Van Thu, Kim, Jeong Ah, Woo, Mi Hee, and Min, Byung Sun
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PRIVETS , *T cells , *GLYCOSIDES , *MITOGEN-activated protein kinases , *PHOSPHORYLATION - Abstract
A previously undescribed nor-dammarane, 3 β ,20,23-trihydroxy-24,25,26,27-tetranordammarane; three previously undescribed secoiridoid glycosides, ligujaponosides A–B, and iso-oleonuzhenide; and twenty three known compounds, were isolated from the fruits of Ligustrum japonicum Thunb. Their chemical structures were elucidated by extensive spectroscopic analyses, including 1D and 2D NMR, and HRMS. The isolated compounds were screened for immunosuppressive effects on T activated cells by evaluating interleukin-2 (IL-2) production. Among them, sesamin inhibited IL-2 production in Jurkat T cells with an IC 50 value of 38 ± 2 μM. In addition, sesamin inhibited the phosphorylation of extracellular signal-regulated protein kinase (ERK), a member of the mitogen-activated protein kinase (MAPK) family, in phorbol 12-myristate 13-acetate (PMA)/A23187-stimulated T cells. Therefore, sesamin was demonstrated to inhibit T cell activation via regulation of MAPK phosphorylation pathway. [ABSTRACT FROM AUTHOR] more...
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- 2017
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7. Scent from Jasminum grandiflorum flowers: Investigation of the change in linalool enantiomers at various developmental stages using chemical and molecular methods.
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Pragadheesh, V.S., Chanotiya, Chandan S., Rastogi, Shubhra, and Shasany, Ajit K.
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JASMINE , *LINALOOL , *ENANTIOMERS , *FLOWERS , *CYCLODEXTRINS , *FATTY acid derivatives , *GENE expression , *POLYMERASE chain reaction - Abstract
Jasminum species are among the most preferred fresh cut flowers in India since ancient times. The plant produces small and fragrant flowers, which are of great demand in the preparation of fragrant garlands and also in perfume industries. Floral volatile of Jasminum grandiflorum L. (Family: Oleaceae) was extracted using solid-phase microextraction and analyzed in enantioselective gas chromatography. Chemical classes of identified volatiles revealed the presence of terpenoids, phenylpropanoids, and fatty acid derivatives. Marker constituent of flower volatiles, linalool was selected for analytical characterization on ethyl- and acetyl-β-cyclodextrin stationary phase. ( R )-(˗)-Linalool was found as major enantiomer in volatiles of floral buds whereas ( S )-(+)-linalool predominated in the volatiles of matured flowers. Simultaneously, a quantitative real-time PCR was performed to find the gene expression of linalool synthase to investigate the mechanism of enantiomeric inversion. The emission pattern of ( R )-(˗)-linalool at different flower developmental stages was well correlated ( P = 0.01) with the gene expression of the cloned linalool synthase from J. grandiflorum . We observed that the successive change in ( R )- to ( S )-linalool ratio from bud to mature flower was mainly due to the enantio- specific transformation and temporal decline of ( R )-linalool producing gene in J. grandiflorum . This enantiomeric change also leads to the difference in flower aroma. Furthermore, this is probably the reason behind consumer's acceptance for jasmine buds rather than bloomed flowers in cut flower segments. [ABSTRACT FROM AUTHOR] more...
- Published
- 2017
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8. Diverse lignans with protective effect against hypoxia/oxidative injuries to H9c2 cells from Syringa pinnatifolia Hemsl.
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Jiao, Shungang, Gao, Xiaoli, Li, Junjun, Zhang, Ruifei, Wuken, Shana, Liu, Changxin, Chen, Suyile, Tu, Pengfei, Huang, Luqi, and Chai, Xingyun
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LIGNANS , *MYOCARDIAL ischemia , *NEOLIGNANS , *CORONARY disease , *HYPOXEMIA , *TRADITIONAL medicine - Abstract
A bioactivity-guided fractionation on the phenolic fractions from the peeled stems of Syringa pinnatifolia Hemsl., one of representative Mongolian folk medicine in China, led to the isolation and structural determination of 11 undescribed lignans and 12 known ones. These lignans cover diverse types, among them syringanones A and B represent an unprecedented carbon skeleton (proposed syringanane) and alashanenol A possesses a rare bicyclo [3.3.1]nonadienemethanol core. Their structures were established by extensive spectroscopic data analysis, X-ray diffraction, and quantum chemical calculations. All isolates were evaluated for their cardioprotective activities on H9c2 cardiomyocytes in vitro. The results showed that five lignans exhibited the protective effects against hypoxia-induced injury at the concentrations of 1.2–40 μM and six lignans exhibited anti-oxidative stress injury at 10–40 μM. These findings account to some extend for the traditional therapeutic effects of S. pinnatifolia for the treatment of ischemic heart diseases in clinic. Eleven undescribed lignans and twelve known ones were isolated from the stems of Syringa pinnatifolia Hemsl. by a bioactivity-guided approach. Their cadioprotective activities on H9c2 cells were evaluated. [Display omitted] • Eleven undescribed lignans were isolated from the stems of Syringa pinnatifolia. • Their structures with absolute configurations were completely resolved. • Syringanones A and B represent an unprecedented carbon skeleton. • Alashanenol A possesses a rare bicyclo [3.3.1]nonadienemethanol core. • These lignans exhibited cadioprotective effects on H9c2 cells. [ABSTRACT FROM AUTHOR] more...
- Published
- 2023
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9. Isolation and structural elements of a water-soluble free radical scavenger from Nyctanthes arbor-tristis leaves.
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Ghosh, Kanika, Ray, Sayani, Bera, Kaushik, and Ray, Bimalendu
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FREE radical scavengers , *AYURVEDIC medicine , *PHYTOCHEMICALS , *ANTIOXIDANTS , *POLYSACCHARIDES , *OLEACEAE - Abstract
The leaves of Nyctanthes arbor-tristis L. (Oleaceae) are used in Ayurvedic medicine for the management of a range of diseases, but reports on its phytochemicals and pharmacological properties are inadequate. Herein, we report purification of an antioxidative polysaccharide (F2) extracted from its leaves by water. The presence of a highly branched polysaccharide (75 kDa) containing esterified phenolic acids was revealed by chemical, chromatographic and spectroscopic analyses. Particularly, ESMS analysis of per acetylated oligomeric fragments derived by Smith degradation provides important structural information on a spectrum of glycerol tagged oligosaccharides. This polysaccharide showed dose dependent free radical scavenging capacity as evidenced by DPPH and Ferric reducing power assay. This pharmacologically active compound (F2) formed a water soluble complex with bovine serum albumin over pH 4.0–7.4. Accordingly, traditional aqueous extraction method provides a molecular entity that induces a pharmacological effect: this could epitomize a smart approach in phytotherapeutic management. [ABSTRACT FROM AUTHOR] more...
- Published
- 2015
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10. Iridoid glucosides in the endemic Picconia azorica (Oleaceae).
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Gousiadou, Chrysoula, Kokubun, Tetsuo, Martins, José, Gotfredsen, Charlotte H., and Jensen, Søren R.
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IRIDOIDS , *ENDEMIC plants , *GLUCOSIDES , *CARBOCYCLIC compounds , *MONOTERPENOIDS , *OLEACEAE - Abstract
In our continued investigation of plants from the family Oleaceae we have now investigated Picconia azorica endemic to the Azores. Like most species within the family it contains the oleoside-based secoiridoid glucosides ligstroside and oleuropein as the main compounds and in addition verbascoside and echinacoside. As with the previously investigated Picconia excelsa , it also contained the carbocyclic iridoid glucosides involved in the biosynthetic pathway to the oleoside derivatives. However, while P. excelsa contained loganin esterified with some monoterpenoid acids, P. azorica contains similar esters of 7- epi -loganic acid named Picconioside A and B. In addition were found the two 7- O - E / Z -cinnamoyl esters of 7- epi -loganic acid named Picconioside C and D. [ABSTRACT FROM AUTHOR] more...
- Published
- 2015
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11. Electrophysiological responses of Philaenus spumarius and Neophilaenus campestris females to plant volatiles
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Eirini Anastasaki, Panagiotis Milonas, Aikaterini Psoma, Dimitrios P. Papachristos, and George K. Partsinevelos
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Volatile Organic Compounds ,biology ,Philaenus spumarius ,Sabinene ,Plant Science ,General Medicine ,Horticulture ,biology.organism_classification ,Xylella ,Biochemistry ,Polygala myrtifolia ,Terpene ,Europe ,Hemiptera ,chemistry.chemical_compound ,Cistus creticus ,chemistry ,Olea ,Oleaceae ,Botany ,Animals ,Female ,Xylella fastidiosa ,Molecular Biology ,Plant Diseases - Abstract
The spittlebugs Philaenus spumarius and Neophilaenus campestris (Hemiptera: Aphrophoridae) are xylem-feeder insects that have been identified as vectors of Xylella fastidiosa in Europe. In the present study, we aim to identify volatile organic compounds (VOCs) that may act as semiochemicals for these species. Using the dynamic headspace technique, we collected VOCs from Olea europaea L. and Polygala myrtifolia L., highly susceptible plant species to X. fastidiosa, Pinus halepensis Mill., a common plant where N. campestris is found during summer, and from host plant species that are used as cover crops or exist as natural vegetation in olive orchards, such as Cistus creticus L., Medicago sativa L., Cynodon dactylon (L.) Pers., Lolium arundinaceum (Schreb.) Darbysh., Apium graveolens L. and Petroselinum crispum (Mill.) Fuss. We tested the response of female antennae on those blends with Gas Chromatography-Electroantennographic Detection (GC-EAD). The chemical profile of C. creticus and P. halepensis was rich in terpenes, alcohols, aldehydes, and esters. In the O. europaea profile, the main compounds were terpenes. As for P. myrtifolia, the volatile profile consisted mostly of alkanes and their substitutes. In the volatile profile of M. sativa, C. dactylon and L. arundinaceum, common volatile compounds were detected. Petroselinum crispum and Apium graveolens chemical profiles were dominated by terpenes. Several compounds elicited a consistent response to the female antennae of both species. In total, 65 compounds elicited consistent EAD responses for P. spumarius and 16 compounds for N. campestris. α-pinene was found in all tested plants and elicited consistent EAD responses of P. spumarius in five plants. In addition, antennae of P. spumarius females responded to camphor, limonene, 4-methyl octane and sabinene. These compounds were found in the volatile profile of at least 5 out of 8 examined plant species. Behavioral bioassays using Y-tube olfactometry were performed on volatiles that elicited antennal responses during electrophysiological studies. Among the compounds tested in behavioral studies, namely (-)-α-pinene, (+)-α-pinene, sabinene, (-)-S-limonene and (1R)-(+)-camphor, only the last one elicited a significant attraction response by P. spumarius females. The results achieved shed light on the VOCs from selected host plant species of X. fastidiosa that are perceived by two important insect vectors and a non-host plant, P. crispum. The identification of semiochemicals for manipulating spittlebugs' behavior contribute to the development of efficient monitoring tools for X. fastidiosa vectors. more...
- Published
- 2021
12. Diplofuranoxin, a disubstituted dihydrofuranone, was produced together with sphaeropsidin A and epi-sphaeropsidone by Diplodia subglobosa, an emerging ash (Fraxinus excelsior L.) pathogen in Europe.
- Author
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Masi, Marco, Di Lecce, Roberta, Calice, Umberto, Linaldeddu, Benedetto Teodoro, Maddau, Lucia, Superchi, Stefano, and Evidente, Antonio
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EUROPEAN ash , *WOOD ash , *PHYTOTOXINS , *CIRCULAR dichroism , *BOTRYOSPHAERIACEAE - Abstract
An undescribed disubstituted dihydrofuranone, named diplofuranoxin, was isolated, together with the six well known metabolites sphaeropsidins A and C, epi -sphaeropsidone, mellein and cis - and trans -4-hydroxymelleins, from the fungal species Diplodia subglobosa , an emerging pathogen involved in the ash dieback aetiology in Europe. Currently, the disease represents the main threat to European ash heritage and the wood associated industry. Diplofuranoxin, was characterized essentially by NMR and HRESIMS spectra as (3Z)-3-(2,3-dihydroxybutylidene)-5-methyldihydrofuran-2(3 H)-one. Its relative and absolute configuration was determined by joining NOESY NMR experiments and computational analysis of electronic circular dichroism spectrum. All the metabolites were screened for phytotoxic, antioomycetes and zootoxic activities and only sphaeropsidin A and epi -sphaeropsidone were active in two out of three bioassays performed. In addition, sphaeropsidin A completely inhibited mycelium growth of Phytophthora cambivora , whereas the inhibition rate of epi -sphaeropsidone was less than 50% at the higher concentration used. Both metabolites were inactive in the Artemia salina assay. Results obtained in this study have allowed to characterize for the first time the main metabolites produced in vitro by D. subglobosa and to increase the knowledge on the metabolic profile of Botryosphaeriaceae for a correct taxonomic classification of the strains belonging to this family. [Display omitted] • Diplodia subglobosa is the causal agent of ash diseases. • A disubstituted dihydrofuranone was isolated from its culture filtrates. • It was characterized by NMR and HRESIMS spectra and named diplofuranoxin. • Other six phytotoxins were isolated and identified. [ABSTRACT FROM AUTHOR] more...
- Published
- 2022
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13. Antioxidant and anti-inflammatory caffeoyl phenylpropanoid and secoiridoid glycosides from Jasminum nervosum stems, a Chinese folk medicine.
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Guo, Zhi-yong, Li, Ping, Huang, Wen, Wang, Jian-jun, Liu, Yu-jing, Liu, Bo, Wang, Ye-ling, Wu, Shi-Biao, Kennelly, Edward J., and Long, Chun-lin
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ANTIOXIDANTS , *ANTI-inflammatory agents , *PHENYLPROPANOIDS , *SECOIRIDOIDS , *GLYCOSIDES , *CHINESE medicine , *JASMINE - Abstract
Eight compounds including four caffeoyl phenylpropanoid glycosides, jasnervosides A–D ( 1 – 4 ), one monoterpenoid glycoside, jasnervoside E ( 5 ), and three secoiridoid glycosides, jasnervosides F–H ( 10 – 12 ), were isolated from the stems of Jasminum nervosum Lour. (Oleaceae), along with four known compounds, poliumoside ( 6 ), verbascoside ( 7 ), α- l -rhamnopyranosyl-(1→3)- O -(α- l -rhamnopyranosyl(1→6)-1- O - E -caffeoyl-β- d -glucopyranoside ( 8 ), and jaspolyanthoside ( 9 ). Their structures were elucidated on the basis of their physicochemical and spectroscopic properties. Compounds 1 , 2 , 4 and 11 displayed potent antioxidant activities in the DPPH assay, while 2 and 3 displayed good activities against LPS-induced TNF-α and IL-1β production in BV2 cells. Compounds 1 – 5 and 10 – 12 were evaluated for their cytotoxic activities against three human cancer cell lines (A-549, Bel-7402, and HCT-8), but none displayed significant activity. [ABSTRACT FROM AUTHOR] more...
- Published
- 2014
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14. Phenolic and lipophilic metabolite adjustments in Olea europaea (olive) trees during drought stress and recovery
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Diana C. G. A. Pinto, Maria Celeste Dias, Catarina Figueiredo, Artur M. S. Silva, and Conceição Santos
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0106 biological sciences ,Metabolite ,Plant Science ,Horticulture ,01 natural sciences ,Biochemistry ,Trees ,Terpene ,chemistry.chemical_compound ,Phenols ,Oleuropein ,Olea ,Food science ,Molecular Biology ,biology ,010405 organic chemistry ,Chemistry ,General Medicine ,biology.organism_classification ,0104 chemical sciences ,Olive trees ,Droughts ,Plant Leaves ,Metabolic pathway ,Oleaceae ,Kaempferol ,010606 plant biology & botany - Abstract
The frequency of combined stress events is increasing due to climate change and represents a new threat to olive (Olea europaea) culture. How olive plants modulate their profile of metabolites under multiple stressing agents remains to unveil, although several metabolites affect plants' resilience, and olive production and quality. Young olive plants were exposed to a water deficit (WD) for 30 days and then exposed to a shock of heat and high UVB-radiation (WDHS+UVB treatment) for 2 days. Then, plants were re-watered and grown under optimal conditions (recovery) for 30 days. Leaves were collected after stress and recovery, analysed by liquid and gas chromatography, and the lipophilic and phenolic profiles were characterized. Except for the oleuropein derivatives, the qualitative metabolite profile was similar during stress and recovery. Metabolite increases or decreases in response to stress were stronger when WD was followed by WDHS+UVB treatment. Phenolic compounds (luteolin-7-O-glucoside, quercetin-3-O-rutinoside, apigenin-7-O-glucoside, chrysoeriol-7-O-glucoside, kaempferol derivatives, oleuropein, and lucidumoside C) were the most involved after WD and WDHS+UVB, possibly acting as reactive oxygen species (ROS) scavengers. Lipophilic compounds were more relevant during the recovery period. The catabolism of fatty acids and carbohydrates may provide the necessary energy for plant performance reestablishment, and sterols, long-chain alkanes, and terpenes metabolic pathways may be shifted for the production of compounds with a more important stress protection role. This work highlights for the first time that tolerance mechanisms activated by WD in olive plants are related to metabolite changes, that are adjusted when other stressors are overlapped (WDHS+UVB), and also help the plants recover. This metabolites' plasticity represents an essential contribution to understanding how dry-farming olive orchards may deal with drought combined with high UV-B or heat. more...
- Published
- 2020
15. Feeding by emerald ash borer larvae induces systemic changes in black ash foliar chemistry
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Chen, Yigen, Whitehill, Justin G.A., Bonello, Pierluigi, and Poland, Therese M.
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EMERALD ash borer , *INSECT feeding & feeds , *INSECT larvae , *PHOTOSYNTHATES , *SEEDLINGS , *SALICYLATES , *INSECT-plant relationships - Abstract
Abstract: The exotic wood-boring pest, emerald ash borer (EAB), Agrilus planipennis Fairmaire (Coleoptera: Buprestidae), has been threatening North American ash (Fraxinus spp.) resources, this being recognized since its first detection in Michigan, USA and Ontario, Canada in 2002. Ash trees are killed by larval feeding in the cambial region, which results in disruption of photosynthate and nutrient translocation. In this study, changes in volatile and non-volatile foliar phytochemicals of potted 2-yr-old black ash, Fraxinus nigra Marshall, seedlings were observed in response to EAB larval feeding in the main stem. EAB larval feeding affected levels of six compounds [hexanal, (E)-2-hexenal, (Z)-3-hexenyl acetate, (E)-β-ocimene, methyl salicylate, and (Z,E)-α-farnesene] with patterns of interaction depending upon compounds of interest and time of observation. Increased methyl salicylate emission suggests similarity in responses induced by EAB larval feeding and other phloem-feeding herbivores. Overall, EAB larval feeding suppressed (Z)-3-hexenyl acetate emission, elevated (E)-β-ocimene emission in the first 30days, but emissions leveled off thereafter, and generally increased the emission of (Z,E)-α-farnesene. Levels of carbohydrates and phenolics increased overall, while levels of proteins and most amino acids decreased in response to larval feeding. Twenty-three amino acids were consistently detected in the foliage of black ash. The three most abundant amino acids were aspartic acid, glutamic acid, glutamine, while the four least abundant were α-aminobutyric acid, β-aminoisobutyric acid, methionine, and sarcosine. Most (16) foliar free amino acids and 6 of the 9 detected essential amino acids decreased with EAB larval feeding. The ecological consequences of these dynamic phytochemical changes on herbivores harbored by ash trees and potential natural enemies of these herbivores are discussed. [Copyright &y& Elsevier] more...
- Published
- 2011
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16. Secoiridoid glucosides and unusual recyclized secoiridoid aglycones from Ligustrum vulgare
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Tanahashi, Takao, Takenaka, Yukiko, Okazaki, Naoaki, Koge, Megumi, Nagakura, Naotaka, and Nishi, Toyoyuki
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GLUCOSIDES , *MONOTERPENES , *PRIVETS , *PYRAN , *LACTONES , *PHYTOCHEMICALS , *HYDROLYSIS , *ENZYMES - Abstract
Abstract: Phytochemical investigation of the dried leaves and twigs of Ligustrum vulgare has led to the isolation of the secoiridoid glucosides, (2′′R)- and (2′′S)-10-hydroxy-2′′-methoxyoleuropeins (1 and 2), and the secoiridoid aglycones, ligustrohemiacetals A (3) and B (4). Their structures were elucidated by spectroscopic and chemical means. Enzymatic hydrolysis of 10-hydroxyoleuropein to the analog of ligustrohemiacetals A and B led to the structural revision of jasmolactones. [Copyright &y& Elsevier] more...
- Published
- 2009
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17. Secoiridoid components from Jasminum grandiflorum
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Sadhu, Samir Kumar, Khan, Md. Sojib, Ohtsuki, Takashi, and Ishibashi, Masami
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GLYCOSIDES , *CARBOHYDRATES , *PHENOLS , *OPTICAL polarization - Abstract
Abstract: Secoiridoid glucosides, 2″-epifraxamoside and demethyl-2″-epifraxamoside, and the secoiridoid, jasminanhydride were isolated from Jasminum grandiflorum together with four previously known phenolics and a triterpene. Structures were elucidated by detailed spectroscopic analysis. Stereochemistry of the compounds was determined by differential NOE experiment. [Copyright &y& Elsevier] more...
- Published
- 2007
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18. Oligomeric secoiridoid glucosides from Jasminum abyssinicum
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Gallo, Francesca Romana, Palazzino, Giovanna, Federici, Elena, Iurilli, Raffaella, Monache, Franco Delle, Chifundera, Kusamba, and Galeffi, Corrado
- Subjects
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GLYCOSIDES , *OLIGOMERS , *JASMINE , *SPECTRUM analysis - Abstract
Abstract: From the root bark of Jasminum abyssinicum (Oleaceae) collected in Congo was isolated tree oligomeric secoiridoid glucosides named craigosides A–C. The three compounds are esters of a cyclopentanoid monoterpene with an iridane skeleton, esterified with three, two and two, respectively, units of oleoside 11-methyl ester. The structures were elucidated by spectroscopic methods and chemical correlations. [Copyright &y& Elsevier] more...
- Published
- 2006
- Full Text
- View/download PDF
19. Molecular cloning and characterization of genes encoding two microsomal oleate desaturases (FAD2) from olive
- Author
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Hernández, M. Luisa, Mancha, Manuel, and Martínez-Rivas, José M.
- Subjects
- *
AMINO acids , *OLEIC acid , *SEED pods , *CLONE cells , *GENE expression - Abstract
Abstract: Two different cDNA sequences, designated OepFAD2-1 and OepFAD2-2, encoding two microsomal oleate desaturases (FAD2) have been isolated from olive (Olea europaea cv. Picual) using a PCR approach. Both deduced amino acid sequences showed the three histidine boxes characteristic of all membrane-bound desaturases, and possess a C-terminal endoplasmic reticulum retention signal. Phylogenetic analysis shows that OepFAD2-1 and OepFAD2-2 are grouped with other plant FAD2 sequences. Functional expression of the corresponding FAD2 cDNAs in yeast confirmed that they encode microsomal oleate desaturases. Genomic Southern blot analysis is consistent with the presence of at least two copies of each OepFAD2 gene in the olive genome. OepFAD2-1 transcript was strongly detected in very young seeds and in leaves, showing low levels in mesocarps, while the transcript of the OepFAD2-2 gene was moderately expressed in developing seeds, ripening mesocarp and leaves. These expression data suggest differential functions for the two olive microsomal oleate desaturase genes, with FAD2-1 possibly responsible for the desaturation of reserve lipids in the young seed, while FAD2-2 may be mainly involved in storage lipid desaturation in the mature seeds and the mesocarp. [Copyright &y& Elsevier] more...
- Published
- 2005
- Full Text
- View/download PDF
20. Chemotaxonomy of the Oleaceae: iridoids as taxonomic markers
- Author
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Jensen, Søren Rosendal, Franzyk, Henrik, and Wallander, Eva
- Subjects
- *
GLUCOSIDES , *PHYLOGENY , *NESTEGIS - Abstract
The distribution and biosynthesis of iridoid glucosides in the Oleaceae is reviewed and five distinct biosynthetic pathways to iridoids have been identified in the family, deoxyloganic acid apparently being a common intermediate. Likewise, the distributions of caffeoyl phenylethanoid glycosides (CPGs), i.e. verbascoside and its analogues, as well as cornoside are listed. Iridoid glucoside data exist for 17 genera of Oleaceae and the occurrence of iridoids from the different biosynthetic pathways correlate extremely well with the phylogenetic classification inferred from recent chloroplast DNA sequence data. Thus the tribe Fontanesieae (Fontanesia) contains “normal” secoiridoids, Forsythieae (Abeliophyllum, Forsythia) contains cornoside and/or iridoids from the forsythide pathway, Myxopyreae (Myxopyrum, Nyctanthes) have iridoids from the myxopyroside pathway, and finally, the two tribes Jasmineae and Oleeae (the remaining genera) both contain iridoids from the oleoside pathway. Within Jasmineae, one group of Jasminum sp. is characterized by the presence of jasminin or similar compounds, while another group of Jasminum species and Menodora display derivatives of 10-hydroxyoleoside, compounds not present in the other group. CPGs are reported from about half of the species investigated. With regard to taxonomy at the order level, the chemical data might support a position within or close to Lamiales due to the common presence of CPGs, the iridoids being of less significance since they are of a type that are barely found elsewhere. [Copyright &y& Elsevier] more...
- Published
- 2002
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- View/download PDF
21. Secoiridoid and iridoid glucosides from Syringa afghanica
- Author
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Takenaka, Yukiko, Okazaki, Naoaki, Tanahashi, Takao, Nagakura, Naotaka, and Nishi, Toyoyuki
- Subjects
- *
LILACS , *OLEACEAE , *GLUCOSIDES - Abstract
Phytochemical investigation of the dried leaves of Syringa afghanica, has led to the isolation of nine secoiridoid glucosides, safghanosides A–H and 2″-epi-frameroside, as well as an iridoid glucoside, syringafghanoside along with nineteen known compounds. The structures were elucidated by spectroscopic and chemical means. [Copyright &y& Elsevier] more...
- Published
- 2002
- Full Text
- View/download PDF
22. Labdane diterpenoids from Forsythia suspensa with anti-inflammatory and anti-viral activities
- Author
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Sheng-Jun Dai, Rong-Xia Liu, Shu-Min Zhang, Kang-Lin Xiang, Lin Zhao, and Ze-Ping Xie
- Subjects
0106 biological sciences ,Circular dichroism ,Stereochemistry ,medicine.drug_class ,Anti-Inflammatory Agents ,Plant Science ,Horticulture ,01 natural sciences ,Biochemistry ,Virus ,Anti-inflammatory ,Labdane ,chemistry.chemical_compound ,Influenza A Virus, H1N1 Subtype ,medicine ,Animals ,Molecular Biology ,Forsythia ,EC50 ,Forsythia suspensa ,biology ,Molecular Structure ,010405 organic chemistry ,General Medicine ,biology.organism_classification ,In vitro ,0104 chemical sciences ,Rats ,chemistry ,Oleaceae ,Diterpenes ,010606 plant biology & botany - Abstract
Five previously undescribed labdane diterpenoids, named Forsypensins A-E, were isolated from the fruits of Forsythia suspensa. The structures and relative configurations of the compounds were elucidated via extensive spectroscopic methods, and their absolute configurations were fully confirmed by single crystal X-ray diffraction analyses using Cu Kα radiation and electronic circular dichroism data. The five labdane diterpenoids showed in vitro anti-inflammatory activity in rat polymorphonuclear leukocytes, inhibiting the rates of β-glucuronidase release by 43.6%–49.2% at concentrations of 10 μM. The compounds also had anti-viral activity against influenza A (H1N1) virus and respiratory syncytial virus (RSV), with IC50 values in the range 21.8–27.4 μM, and EC50 values in the range 10.5–15.4 μM, respectively. more...
- Published
- 2019
23. Ecological fitting: Chemical profiles of plant hosts provide insights on selection cues and preferences for a major buprestid pest
- Author
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James H. Tumlinson, Katalin Böröczky, Donnie L. Peterson, and Don Cipollini
- Subjects
0106 biological sciences ,Agrilus ,Fraxinus nigra ,Oleaceae ,Oviposition ,Plant Science ,Horticulture ,Fraxinus ,01 natural sciences ,Biochemistry ,Emerald ash borer ,Chionanthus ,Botany ,Animals ,Molecular Biology ,biology ,010405 organic chemistry ,Host (biology) ,Green leaf volatiles ,General Medicine ,biology.organism_classification ,0104 chemical sciences ,Coleoptera ,Larva ,Female ,PEST analysis ,Cues ,010606 plant biology & botany - Abstract
Specific cues used by emerald ash borer (EAB, Agrilus planipennis) to select hosts are largely unknown. Attractants are likely general and the use of novel host plants provides an opportunity to investigate the commonality of these cues. We examined volatile profiles emitted by five plants that can host EAB and estimated their importance in explaining known oviposition preferences. Foliage volatiles were collected from potted black ash (Fraxinus nigra), Manchurian ash (F. mandshurica), blue ash (F. quadrangulata), white fringetree (Chionanthus virginicus), and olive (Olea europaea) and analyzed using GC-MS. Fifty-nine compounds were detected including eight green leaf volatiles (GLV), 12 monoterpenes, and 21 sesquiterpenes. Ordination plots show separation of species by full foliage profiles, monoterpenes, sesquiterpenes, and known antennally active compounds, but GLVs were similar across hosts. Random Forest (RF) analysis revealed eight compounds that separated plant species with an error rate of ~19%, consisting mostly of sesquiterpenes. Similarity of GLV profiles among known hosts suggests they serve as general cues for host selection. Manchurian ash, a resistant host, produced the highest quantities and variety of sesquiterpenes indicating that some of these chemicals may be antixenotic. All compounds identified by RF have been implicated as deterrents or attractants to woodborers in other studies and should be investigated for adult antennal activity and attraction. more...
- Published
- 2019
24. Electrophysiological responses of Philaenus spumarius and Neophilaenus campestris females to plant volatiles.
- Author
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Anastasaki, Eirini, Psoma, Aikaterini, Partsinevelos, George, Papachristos, Dimitrios, and Milonas, Panagiotis
- Subjects
- *
TALL fescue , *OLIVE , *ELECTROPHYSIOLOGY , *CELERY , *XYLELLA fastidiosa , *TERPENES , *ALEPPO pine , *BERMUDA grass - Abstract
The spittlebugs Philaenus spumarius and Neophilaenus campestris (Hemiptera: Aphrophoridae) are xylem-feeder insects that have been identified as vectors of Xylella fastidiosa in Europe. In the present study, we aim to identify volatile organic compounds (VOCs) that may act as semiochemicals for these species. Using the dynamic headspace technique, we collected VOCs from Olea europaea L. and Polygala myrtifolia L. , highly susceptible plant species to X. fastidiosa, Pinus halepensis Mill., a common plant where N. campestris is found during summer, and from host plant species that are used as cover crops or exist as natural vegetation in olive orchards, such as Cistus creticus L. , Medicago sativa L., Cynodon dactylon (L.) Pers. , Lolium arundinaceum (Schreb.) Darbysh., Apium graveolens L. and Petroselinum crispum (Mill.) Fuss. We tested the response of female antennae on those blends with Gas Chromatography-Electroantennographic Detection (GC-EAD). The chemical profile of C. creticus and P. halepensis was rich in terpenes, alcohols, aldehydes, and esters. In the O. europaea profile, the main compounds were terpenes. As for P. myrtifolia, the volatile profile consisted mostly of alkanes and their substitutes. In the volatile profile of M. sativa, C. dactylon and L. arundinaceum, common volatile compounds were detected. Petroselinum crispum and Apium graveolens chemical profiles were dominated by terpenes. Several compounds elicited a consistent response to the female antennae of both species. In total, 65 compounds elicited consistent EAD responses for P. spumarius and 16 compounds for N. campestris. α –pinene was found in all tested plants and elicited consistent EAD responses of P. spumarius in five plants. In addition, antennae of P. spumarius females responded to camphor, limonene, 4-methyl octane and sabinene. These compounds were found in the volatile profile of at least 5 out of 8 examined plant species. Behavioral bioassays using Y-tube olfactometry were performed on volatiles that elicited antennal responses during electrophysiological studies. Among the compounds tested in behavioral studies, namely (−)- α- pinene, (+)- α -pinene, sabinene, (−)- S -limonene and (1 R)-(+)-camphor, only the last one elicited a significant attraction response by P. spumarius females. The results achieved shed light on the VOCs from selected host plant species of X. fastidiosa that are perceived by two important insect vectors and a non-host plant, P. crispum. The identification of semiochemicals for manipulating spittlebugs' behavior contribute to the development of efficient monitoring tools for X. fastidiosa vectors. Electrophysical responses of Philaenus spumarius and Neophilaenus campestris adults , vectors of Xylella fastidiosa, were recorded on volatiles collected from 9 different plants. Olfactometer bioassays showed significant attraction to camphor for P. spumarius females. [Display omitted] • VOCs from significant plants in the epidemiology of X. fastidiosa were identified. • Electrophysiological responses of spittlebugs were recorded by GC-EAD. • Several compounds elicited EAD responses for P. spumarius and N. campestris. • Behavioral experiments with electrophysiological active compounds were conducted. • P. spumarius females significantly chose the camphor odor in a Y-tube olfactometer. [ABSTRACT FROM AUTHOR] more...
- Published
- 2021
- Full Text
- View/download PDF
25. Alkaloids bearing rare skeletons from Forsythia suspensa with anti-inflammatory and anti-viral activities in vitro.
- Author
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Zhao, Lin, Li, Wei, Dai, Sheng-Jun, Liu, Rong-Xia, Xie, Ze-Ping, Zhang, Shu-Min, and Yue, Xi-Dian
- Subjects
- *
ALKALOIDS , *RESPIRATORY syncytial virus , *CHINESE medicine , *INFLUENZA A virus, H1N1 subtype , *ISOQUINOLINE alkaloids , *SKELETON , *INFLUENZA A virus - Abstract
Five alkaloids, including two previously undescribed alkaloids, named forsyshiyanines A and B, attributable to the rare skeletons 4b,5,6,7,8,8a,9,10-octahydrobenzo[ f ]quinoline and (6,7-dihydro-5 H -cyclopenta[ c ]pyridin-7-yl)methyl, respectively, along with three known ones (3 – 5), were isolated from the ripe fruits of Forsythia suspensa. The chemical structures including absolute configurations of two undescribed compounds were established using integrated spectroscopic techniques, electronic circular dichroism calculations, and single-crystal x-ray diffraction analysis. In vitro , five alkaloids showed anti-inflammatory activities, with the inhibition rates of the release of β -glucuronidase from polymorphonuclear leukocytes of rats being in the range 47.9%–56.0% at a concentration of 10 μ M. Moreover, five compounds exhibited anti-viral activities against influenza A virus and respiratory syncytial virus, with IC 50 values in the range of 7.3–32.5 μM and EC 50 values in the range 3.7–14.1 μM. The fruit of Forsythia suspensa is a traditional Chinese medicine with good anti-inflammatory and anti-viral activities. [Display omitted] • Two undescribed alkaloids were isolated from the fruits of Forsythia suspensa. • The absolute configurations of two undescribed alkaloids were determined. • Five alkaloids showed significant anti-inflammatory activities. • Five alkaloids showed anti-viral activities against the H1N1 virus and RSV. [ABSTRACT FROM AUTHOR] more...
- Published
- 2021
- Full Text
- View/download PDF
26. Phenolic and lipophilic metabolite adjustments in Olea europaea (olive) trees during drought stress and recovery.
- Author
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Dias, Maria Celeste, Pinto, Diana C.G.A., Figueiredo, Catarina, Santos, Conceição, and Silva, Artur M.S.
- Subjects
- *
OLIVE , *REACTIVE oxygen species , *DROUGHTS , *PLANT performance , *PHENOLS , *FOREST declines - Abstract
The frequency of combined stress events is increasing due to climate change and represents a new threat to olive (Olea europaea) culture. How olive plants modulate their profile of metabolites under multiple stressing agents remains to unveil, although several metabolites affect plants' resilience, and olive production and quality. Young olive plants were exposed to a water deficit (WD) for 30 days and then exposed to a shock of heat and high UVB-radiation (WDHS+UVB treatment) for 2 days. Then, plants were re-watered and grown under optimal conditions (recovery) for 30 days. Leaves were collected after stress and recovery, analysed by liquid and gas chromatography, and the lipophilic and phenolic profiles were characterized. Except for the oleuropein derivatives, the qualitative metabolite profile was similar during stress and recovery. Metabolite increases or decreases in response to stress were stronger when WD was followed by WDHS+UVB treatment. Phenolic compounds (luteolin-7- O -glucoside, quercetin-3- O -rutinoside, apigenin-7- O -glucoside, chrysoeriol-7- O -glucoside, kaempferol derivatives, oleuropein, and lucidumoside C) were the most involved after WD and WDHS+UVB, possibly acting as reactive oxygen species (ROS) scavengers. Lipophilic compounds were more relevant during the recovery period. The catabolism of fatty acids and carbohydrates may provide the necessary energy for plant performance reestablishment, and sterols, long-chain alkanes, and terpenes metabolic pathways may be shifted for the production of compounds with a more important stress protection role. This work highlights for the first time that tolerance mechanisms activated by WD in olive plants are related to metabolite changes, that are adjusted when other stressors are overlapped (WDHS+UVB), and also help the plants recover. This metabolites' plasticity represents an essential contribution to understanding how dry-farming olive orchards may deal with drought combined with high UV-B or heat. [Display omitted] • WD and WDHS+UVB activate the same metabolite responses. • WDHS+UVB induce a stronger metabolite quantity change. • Polyphenols are the most involved to counteract the stress negative effects. • Lipophilic metabolites are more involved in physiological reestablishment after stress. [ABSTRACT FROM AUTHOR] more...
- Published
- 2021
- Full Text
- View/download PDF
27. Isolation and structural elements of a water-soluble free radical scavenger from Nyctanthes arbor-tristis leaves
- Author
-
Kaushik Bera, Kanika Ghosh, Bimalendu Ray, and Sayani Ray
- Subjects
Nyctanthes ,DPPH ,Oleaceae ,Plant Science ,Horticulture ,Polysaccharide ,Biochemistry ,Antioxidants ,chemistry.chemical_compound ,Phenols ,Polysaccharides ,Glycerol ,medicine ,Organic chemistry ,Bovine serum albumin ,Nuclear Magnetic Resonance, Biomolecular ,Molecular Biology ,chemistry.chemical_classification ,Aqueous solution ,biology ,Water ,Serum Albumin, Bovine ,Free Radical Scavengers ,General Medicine ,Free radical scavenger ,biology.organism_classification ,Plant Leaves ,Solubility ,chemistry ,biology.protein ,Ferric ,medicine.drug - Abstract
The leaves of Nyctanthes arbor-tristis L. (Oleaceae) are used in Ayurvedic medicine for the management of a range of diseases, but reports on its phytochemicals and pharmacological properties are inadequate. Herein, we report purification of an antioxidative polysaccharide (F2) extracted from its leaves by water. The presence of a highly branched polysaccharide (75 kDa) containing esterified phenolic acids was revealed by chemical, chromatographic and spectroscopic analyses. Particularly, ESMS analysis of per acetylated oligomeric fragments derived by Smith degradation provides important structural information on a spectrum of glycerol tagged oligosaccharides. This polysaccharide showed dose dependent free radical scavenging capacity as evidenced by DPPH and Ferric reducing power assay. This pharmacologically active compound (F2) formed a water soluble complex with bovine serum albumin over pH 4.0–7.4. Accordingly, traditional aqueous extraction method provides a molecular entity that induces a pharmacological effect: this could epitomize a smart approach in phytotherapeutic management. more...
- Published
- 2015
- Full Text
- View/download PDF
28. Labdane diterpenoids from Forsythia suspensa with anti-inflammatory and anti-viral activities.
- Author
-
Xiang, Kang-Lin, Liu, Rong-Xia, Zhao, Lin, Xie, Ze-Ping, Zhang, Shu-Min, and Dai, Sheng-Jun
- Subjects
- *
DITERPENES , *H1N1 influenza , *RESPIRATORY syncytial virus , *SINGLE crystals , *CIRCULAR dichroism , *ANTIVIRAL agents - Abstract
Five previously undescribed labdane diterpenoids, named Forsypensins A-E, were isolated from the fruits of Forsythia suspensa. The structures and relative configurations of the compounds were elucidated via extensive spectroscopic methods, and their absolute configurations were fully confirmed by single crystal X-ray diffraction analyses using Cu Kα radiation and electronic circular dichroism data. The five labdane diterpenoids showed in vitro anti-inflammatory activity in rat polymorphonuclear leukocytes, inhibiting the rates of β -glucuronidase release by 43.6%–49.2% at concentrations of 10 μ M. The compounds also had anti-viral activity against influenza A (H1N1) virus and respiratory syncytial virus (RSV), with IC 50 values in the range 21.8–27.4 μ M, and EC 50 values in the range 10.5–15.4 μ M, respectively. Image 104160 • Five undescribed labdane diterpenoids were isolated from the fruits of Forsythia suspensa. • The discovery of undescribed labdane diterpenoids is a further illustration to the diverse constituents of Forsythia. • Five undescribed labdane diterpenoids were found to show anti-inflammatory and anti-viral activities. [ABSTRACT FROM AUTHOR] more...
- Published
- 2020
- Full Text
- View/download PDF
29. The antioxidant system in Olea europaea to enhanced UV-B radiation also depends on flavonoids and secoiridoids.
- Author
-
Dias, Maria Celeste, Pinto, Diana C.G.A., Freitas, Helena, Santos, Conceição, and Silva, Artur M.S.
- Subjects
- *
OLIVE , *HYDROXYCINNAMIC acids , *ACID derivatives , *GLUTATHIONE reductase , *RADIATION , *SECOIRIDOIDS - Abstract
The Mediterranean crop Olea europaea is often exposed to high UV-B irradiation conditions. To understand how this species modulates its enzymatic and non-enzymatic antioxidant system under high UV-B radiation, young O. europaea plants (cultivar "Galega Vulgar") were exposed, for five days, to UV-B radiation (6.5 kJ m−2 d−1 and 12.4 kJ m−2 d−1). Our data indicate that UV-doses slightly differ in the modulation of the antioxidant protective mechanisms. Particularly, superoxide dismutase (SOD), guaiacol peroxidase (GPox) and catalase (CAT) activities increased contributing to H 2 O 2 homeostasis, being more solicited by higher UV-B doses. Also, glutathione reductase (Gr) activity, ascorbate (AsA) and reduced glutathione (GSH) pools increased particularly under the highest dose, suggesting a higher mobilization of the antioxidant system in this dose. The leaf metabolites' profile of this cultivar was analysed by UHPLC-MS. Interestingly, high levels of verbascoside were found, followed by oleuropein and luteolin-7- O -glucoside. Both UV-B treatments affected mostly less abundant flavonoids (decreasing 4ʹ-methoxy luteolin and 4ʹ or 3ʹ-methoxy luteolin glucoside) and hydroxycinnamic acid derivatives (HCAds, increasing β-hydroxyverbascoside). These changes show not only different mobilization with the UV-intensity, but also reinforce for the first time the protective roles of these minor compounds against UV-B, as reactive oxygen species (ROS) scavengers and UV-B shields, in complement with other antioxidant systems (e.g. AsA/GSH cycle), particularly for high UV-B doses. Secoiridoids also standout in the response to both UV-B doses, with decreases of oleuropein and increases 2ʹʹ-methoxyoleuropein. Being oleuropein an abundant compound, data suggest that secoiridoids play a more important role than flavonoids and HCAds, in O. europaea protection against UV-B, possibly by acting as signalling molecules and ROS scavengers. This is the first report on the influence of UV-B radiation on the secoiridoid oleuropein, and provides a novel insight to the role of this compound in the O. europaea antioxidant defence mechanisms. Image 1 • Moderate and high UV-B doses activated similar antioxidant protective mechanisms. • High UV-B dose promote higher activation of the antioxidant enzymes and AsA/GSH. • Flavonoids, secoiridoids and HCAds respond similarly to 6.5 and 12.4 kJ m−2d−1 UV-B • UV-B treatments reduce some protective compounds level, such as oleuropein. [ABSTRACT FROM AUTHOR] more...
- Published
- 2020
- Full Text
- View/download PDF
30. Scent from Jasminum grandiflorum flowers: Investigation of the change in linalool enantiomers at various developmental stages using chemical and molecular methods
- Author
-
V.S. Pragadheesh, Chandan S. Chanotiya, Ajit Kumar Shasany, and Shubhra Rastogi
- Subjects
0106 biological sciences ,0301 basic medicine ,Chromatography, Gas ,Jasminum ,Acyclic Monoterpenes ,Plant Science ,Cut flowers ,Flowers ,Horticulture ,Real-Time Polymerase Chain Reaction ,01 natural sciences ,Biochemistry ,03 medical and health sciences ,Jasminum grandiflorum ,chemistry.chemical_compound ,Linalool ,Gene Expression Regulation, Plant ,Botany ,Molecular Biology ,Aroma ,Hydro-Lyases ,Solid Phase Microextraction ,Volatile Organic Compounds ,biology ,fungi ,food and beverages ,Gene Expression Regulation, Developmental ,Stereoisomerism ,General Medicine ,biology.organism_classification ,Terpenoid ,Perfume ,Transformation (genetics) ,030104 developmental biology ,chemistry ,Oleaceae ,Odorants ,Monoterpenes ,Gas chromatography ,010606 plant biology & botany - Abstract
Jasminum species are among the most preferred fresh cut flowers in India since ancient times. The plant produces small and fragrant flowers, which are of great demand in the preparation of fragrant garlands and also in perfume industries. Floral volatile of Jasminum grandiflorum L. (Family: Oleaceae) was extracted using solid-phase microextraction and analyzed in enantioselective gas chromatography. Chemical classes of identified volatiles revealed the presence of terpenoids, phenylpropanoids, and fatty acid derivatives. Marker constituent of flower volatiles, linalool was selected for analytical characterization on ethyl- and acetyl-β-cyclodextrin stationary phase. (R)-(˗)-Linalool was found as major enantiomer in volatiles of floral buds whereas (S)-(+)-linalool predominated in the volatiles of matured flowers. Simultaneously, a quantitative real-time PCR was performed to find the gene expression of linalool synthase to investigate the mechanism of enantiomeric inversion. The emission pattern of (R)-(˗)-linalool at different flower developmental stages was well correlated (P = 0.01) with the gene expression of the cloned linalool synthase from J. grandiflorum. We observed that the successive change in (R)- to (S)-linalool ratio from bud to mature flower was mainly due to the enantio- specific transformation and temporal decline of (R)-linalool producing gene in J. grandiflorum. This enantiomeric change also leads to the difference in flower aroma. Furthermore, this is probably the reason behind consumer's acceptance for jasmine buds rather than bloomed flowers in cut flower segments. more...
- Published
- 2017
31. Effect of different environmental stresses on the expression of oleate desaturase genes and fatty acid composition in olive fruit
- Author
-
María Nieves Padilla, M. Dolores Sicardo, M. Luisa Hernández, José Manuel Martínez-Rivas, and Manuel Mancha
- Subjects
Fatty Acid Desaturases ,FAD2 ,Linoleic acid ,Time Factors ,FAD6 ,Palmitic Acid ,Plant Science ,Horticulture ,Biology ,Biochemistry ,chemistry.chemical_compound ,Stress, Physiological ,Olea ,Gene expression ,Escherichia coli ,Phosphatidylcholine desaturase ,Molecular Biology ,chemistry.chemical_classification ,Wound Healing ,Temperature ,Olive ,Fatty acid ,Palmotolinoleic acid ,General Medicine ,biology.organism_classification ,Lipids ,Oleic acid ,Olea europaes ,Enzyme ,chemistry ,Fruit ,Olea desaturase ,Oleaceae ,Microsome ,Oleae - Abstract
The regulation of microsomal and plastidial oleate desaturases by low and high temperature, darkness, and wounding was investigated. To this end, their gene expression levels and the fatty acid composition was determined in the mesocarp tissue of olive fruit from the Picual and Arbequina varieties subjected to the corresponding stress treatments. Firstly, a plastidial oleate desaturase from olive was cloned and its functional identity was confirmed by overexpression in Escherichia coli. The results showed that temperature and light regulate olive oleate desaturase genes at transcriptional level. However, no correlation between their expression levels and the linoleic acid content in microsomal and plastidial lipids was found. In addition, the involvement of microsomal but not plastidial oleate desaturases in the wounding response of olive fruit mesocarp is demonstrated. The fatty acid analysis revealed the appearance of palmitolinoleic acid only in microsomal lipids, reaching a maximum 3 h after wounding. © 2010 Elsevier Ltd. All rights reserved., This work was supported by Research Projects AGL2004-02060 from MEC (Spain) and P06-AGR-02151 from Junta de Andalucía (Spain). more...
- Published
- 2011
- Full Text
- View/download PDF
32. Ecological fitting: Chemical profiles of plant hosts provide insights on selection cues and preferences for a major buprestid pest.
- Author
-
Peterson DL, Böröczky K, Tumlinson J, and Cipollini D
- Subjects
- Animals, Cues, Female, Larva, Oviposition, Coleoptera, Fraxinus, Oleaceae
- Abstract
Specific cues used by emerald ash borer (EAB, Agrilus planipennis) to select hosts are largely unknown. Attractants are likely general and the use of novel host plants provides an opportunity to investigate the commonality of these cues. We examined volatile profiles emitted by five plants that can host EAB and estimated their importance in explaining known oviposition preferences. Foliage volatiles were collected from potted black ash (Fraxinus nigra), Manchurian ash (F. mandshurica), blue ash (F. quadrangulata), white fringetree (Chionanthus virginicus), and olive (Olea europaea) and analyzed using GC-MS. Fifty-nine compounds were detected including eight green leaf volatiles (GLV), 12 monoterpenes, and 21 sesquiterpenes. Ordination plots show separation of species by full foliage profiles, monoterpenes, sesquiterpenes, and known antennally active compounds, but GLVs were similar across hosts. Random Forest (RF) analysis revealed eight compounds that separated plant species with an error rate of ~19%, consisting mostly of sesquiterpenes. Similarity of GLV profiles among known hosts suggests they serve as general cues for host selection. Manchurian ash, a resistant host, produced the highest quantities and variety of sesquiterpenes indicating that some of these chemicals may be antixenotic. All compounds identified by RF have been implicated as deterrents or attractants to woodborers in other studies and should be investigated for adult antennal activity and attraction., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2020 Elsevier Ltd. All rights reserved.) more...
- Published
- 2020
- Full Text
- View/download PDF
33. Oligomeric secoiridoid glucosides from Jasminum abyssinicum☆
- Author
-
Raffaella Iurilli, Francesca Romana Gallo, Elena Federici, Corrado Galeffi, Franco Delle Monache, Giovanna Palazzino, and Kusamba Chifundera
- Subjects
Iridoid ,Jasminum ,medicine.drug_class ,Stereochemistry ,Monoterpene ,Iridoid Glucosides ,Plant Science ,Horticulture ,Plant Roots ,Biochemistry ,chemistry.chemical_compound ,Glucoside ,medicine ,Organic chemistry ,Iridoids ,Molecular Biology ,Molecular Structure ,biology ,Jasminum abyssinicum ,Chemistry ,General Medicine ,biology.organism_classification ,Secoiridoid Glucosides ,Oleaceae ,visual_art ,Plant Bark ,visual_art.visual_art_medium ,Bark - Abstract
From the root bark of Jasminum abyssinicum (Oleaceae) collected in Congo was isolated tree oligomeric secoiridoid glucosides named craigosides A-C. The three compounds are esters of a cyclopentanoid monoterpene with an iridane skeleton, esterified with three, two and two, respectively, units of oleoside 11-methyl ester. The structures were elucidated by spectroscopic methods and chemical correlations. more...
- Published
- 2006
- Full Text
- View/download PDF
34. Chemotaxonomy of the Oleaceae: iridoids as taxonomic markers
- Author
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Eva Wallander, Henrik Franzyk, and Søren Rosendal Jensen
- Subjects
Nyctanthes ,Iridoid ,medicine.drug_class ,Oleaceae ,Iridoid Glucosides ,Plant Science ,Horticulture ,Biochemistry ,chemistry.chemical_compound ,Verbascoside ,Glucosides ,Botany ,medicine ,Iridoids ,Menodora ,Molecular Biology ,Nestegis ,Phylogeny ,Pyrans ,biology ,General Medicine ,Classification ,biology.organism_classification ,Abeliophyllum ,chemistry - Abstract
The distribution and biosynthesis of iridoid glucosides in the Oleaceae is reviewed and five distinct biosynthetic pathways to iridoids have been identified in the family, deoxyloganic acid apparently being a common intermediate. Likewise, the distributions of caffeoyl phenylethanoid glycosides (CPGs), i.e. verbascoside and its analogues, as well as cornoside are listed. Iridoid glucoside data exist for 17 genera of Oleaceae and the occurrence of iridoids from the different biosynthetic pathways correlate extremely well with the phylogenetic classification inferred from recent chloroplast DNA sequence data. Thus the tribe Fontanesieae (Fontanesia) contains "normal" secoiridoids, Forsythieae (Abeliophyllum, Forsythia) contains cornoside and/or iridoids from the forsythide pathway, Myxopyreae (Myxopyrum, Nyctanthes) have iridoids from the myxopyroside pathway, and finally, the two tribes Jasmineae and Oleeae (the remaining genera) both contain iridoids from the oleoside pathway. Within Jasmineae, one group of Jasminum sp. is characterized by the presence of jasminin or similar compounds, while another group of Jasminum species and Menodora display derivatives of 10-hydroxyoleoside, compounds not present in the other group. CPGs are reported from about half of the species investigated. With regard to taxonomy at the order level, the chemical data might support a position within or close to Lamiales due to the common presence of CPGs, the iridoids being of less significance since they are of a type that are barely found elsewhere. more...
- Published
- 2002
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35. Secoiridoid and iridoid glucosides from Syringa afghanica
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Naoaki Okazaki, Takao Tanahashi, Naotaka Nagakura, Yukiko Takenaka, and Toyoyuki Nishi
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Magnetic Resonance Spectroscopy ,Iridoid ,Traditional medicine ,Chemistry ,medicine.drug_class ,Oleaceae ,Iridoid Glucosides ,Plant Science ,General Medicine ,Horticulture ,Biochemistry ,Plant Leaves ,chemistry.chemical_compound ,Glucosides ,Phytochemical ,Glucoside ,Secoiridoid Glucosides ,Botany ,medicine ,Iridoids ,Molecular Biology ,Pyrans - Abstract
Phytochemical investigation of the dried leaves of Syringa afghanica, has led to the isolation of nine secoiridoid glucosides, safghanosides A-H and 2"-epi-frameroside, as well as an iridoid glucoside, syringafghanoside along with nineteen known compounds. The structures were elucidated by spectroscopic and chemical means. more...
- Published
- 2002
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36. Iridoid glucosides in the endemic Picconia azorica (Oleaceae)
- Author
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Tetsuo Kokubun, José Martins, Charlotte Held Gotfredsen, Søren Rosendal Jensen, and Chrysoula Gousiadou
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Iridoid Glycosides ,Oleaceae ,Iridoid Glucosides ,Picconia azorica ,Plant Science ,Horticulture ,Biochemistry ,chemistry.chemical_compound ,Verbascoside ,Glucosides ,Phenols ,Oleuropein ,Botany ,Iridoids ,Glycosides ,Molecular Biology ,Azores ,Pyrans ,biology ,Molecular Structure ,Loganin ,General Medicine ,biology.organism_classification ,Picconia excelsa ,chemistry - Abstract
In our continued investigation of plants from the family Oleaceae we have now investigated Picconia azorica endemic to the Azores. Like most species within the family it contains the oleoside-based secoiridoid glucosides ligstroside and oleuropein as the main compounds and in addition verbascoside and echinacoside. As with the previously investigated Picconia excelsa, it also contained the carbocyclic iridoid glucosides involved in the biosynthetic pathway to the oleoside derivatives. However, while P. excelsa contained loganin esterified with some monoterpenoid acids, P. azorica contains similar esters of 7-epi-loganic acid named Picconioside A and B. In addition were found the two 7-O-E/Z-cinnamoyl esters of 7-epi-loganic acid named Picconioside C and D. more...
- Published
- 2014
37. Four secoiridoid glucosides from fraxinus insularis
- Author
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Takao Tanahashi, Hiroshi Kuwajima, Naotaka Nagakura, Parida, Yukiko Takenaka, Kenichiro Inoue, and Chen-Chang Chen
- Subjects
Iridoid ,biology ,medicine.drug_class ,Stereochemistry ,Plant Science ,General Medicine ,Horticulture ,biology.organism_classification ,Biochemistry ,chemistry.chemical_compound ,Glucoside ,chemistry ,Secoiridoid Glucosides ,Oleaceae ,Botany ,medicine ,Molecular Biology ,Fraxinus insularis - Abstract
Investigation of the leaves of Fraxinus insularis has led to the isolation of four new secoiridoid glucosides, insularoside-3′- O - β - d -glucoside, insularoside-3′, 6‴-di- O - β - d -glucoside, insuloside and desrhamnosyloleoacteoside, together with ligstroside. The structures of the new compounds were determined on the basis of spectroscopic methods. more...
- Published
- 1998
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38. Monoterpenoid glycosides from ligustrum robustum
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Jun Tian, Hongjie Zhang, De-Yuan Chen, Han-Dong Sun, Lu-Tai Pan, and Pin Yao
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chemistry.chemical_classification ,Ligustrum robustum ,biology ,Stereochemistry ,Monoterpene ,Glycoside ,Plant Science ,General Medicine ,Horticulture ,biology.organism_classification ,Biochemistry ,Terpenoid ,chemistry.chemical_compound ,chemistry ,Oleaceae ,Botany ,Molecular Biology ,Geraniol - Abstract
Eight new monoterpenoid glycosides named ligurobustosides A, B, C, E, F, I, J and K were isolated from the leaves of Ligustrum robustum. Their structures were established as geraniol (3'-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside), geraniol (3'-O-alpha-L-rhamnopyranosyl-4'-caffeoyl-beta-D-glucopyranoside), geraniol (3'-O-alpha-L-rhamnopyranosyl-4'-p-coumaroyl-beta-D-glucopyranoside), geraniol (3'-O-alpha-L-rhamnopyranosyl-6'-O-p-coumaroyl-beta-D-glucopyranoside), 6-hydroxy-3:7-dimethyl-2E,7-octadienyl-(3'-O-alpha-L-rhamnopyranosyl-6'-O-p-coumaroyl-beta-D-glucopyranoside), 7-hydroxy-3,7-dimethyl-2E,5E-octadienyl-(3'-O-alpha-L-rhamnopyranosyl-4'-O-p-coumaroyl)-beta-D-glucopyranside), geraniol-[(3 "-O-alpha-L-rhamnopyranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl)-(4'-O-p-coumaroyl-beta-D-glucopyranoside], 6,7-dihydroxy-3,7-dimethyl-2E-octadienyl-(3'-O-alpha-L-rhamnopyranosyl-4'-O-p-coumaroyl-beta-D-glucopyranoside) respectively, by spectroscopic and chemical methods. (C) 1998 Elsevier Science Ltd. All rights reserved. more...
- Published
- 1998
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39. Analysis of volatiles from callus cultures of olive Olea europaea
- Author
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Mark Williams, Maria T. Morales, John L. Harwood, and Ramón Aparicio
- Subjects
chemistry.chemical_classification ,biology ,food and beverages ,Plant Science ,General Medicine ,Horticulture ,biology.organism_classification ,Biochemistry ,Lipoxygenase ,chemistry ,Olea ,Callus ,Oleaceae ,Botany ,biology.protein ,Cultivar ,Food science ,Gas chromatography ,Molecular Biology ,Aroma ,Polyunsaturated fatty acid - Abstract
The lipoxygenase pathway in olive fruit gives rise to volatile products which influence the aroma of the harvested oil. In this study dynamic headspace gas chromatography was used in order to investigate volatile production by different olive cultivars. Olive callus cultures were used as a model for this purpose, because of the ease of standardising the growth conditions of the calli compared to working with field-grown material. The cultures contained substantial amounts of the polyunsaturated fatty acids, linoleate and α-linolenate, which are the normal substrates for lipoxygenases. Most of the major volatiles that characterise virgin olive oil were also produced by the cultures, especially the unsaturated and saturated C6 aldehydes, alcohols and their acetyl esters. Moreover, by means of ANOVA test, a strong effect of cultivar on volatile production in olive cultures was clearly established. This agreed with data for olive oils from different cultivars, which are also easily distinguished by headspace gas liquid chromatography. We have also demonstrated that changing the culture conditions for temperature and pH produced qualitative and quantitative alterations in volatile production. more...
- Published
- 1998
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40. Monoterpene alkaloids, iridoids and phenylpropanoid glycosides from Osmanthus austrocaledonica
- Author
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Yvonne Ranarivelo, François Tillequin, Alexios-Leandros Skaltsounis, Rabah Benkrief, Jacques Pusset, Thierry Sevenet, and Michel H. J. Koch
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chemistry.chemical_classification ,Osmanthus ,Iridoid ,biology ,medicine.drug_class ,Stereochemistry ,Alkaloid ,Monoterpene ,Flavonoid ,Glycoside ,Plant Science ,General Medicine ,Horticulture ,biology.organism_classification ,Biochemistry ,chemistry.chemical_compound ,chemistry ,Oleaceae ,medicine ,Organic chemistry ,Phenols ,Molecular Biology - Abstract
Six monoterpene alkaloids have been isolated from the aerial parts of Osmanthus austrocaledonica. Two of these, dihydrojasminine and austrodimerine, are novel compounds. Their structures have been elucidated on the basis of their spectral data and molecular modeling. Seven iridoids and six phenolic compounds have been also isolated from the same plant. Two of these, austrosmoside and 6′-O-β-(E)-cinnamoylverbascoside, are novel compounds. Their structures have been deduced from their spectral data and confirmed by chemical correlations. more...
- Published
- 1998
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41. Secoiridoid glucosides from Jasminum urophyllum
- Author
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Ya-Ching Shen and Pei-Wen Hsieh
- Subjects
Folk medicine ,Iridoid ,medicine.drug_class ,Urophyllum ,Plant Science ,General Medicine ,Horticulture ,Biology ,biology.organism_classification ,Biochemistry ,chemistry.chemical_compound ,Glucoside ,chemistry ,Secoiridoid Glucosides ,Oleaceae ,Botany ,medicine ,Molecular Biology - Abstract
The three new secoiridoid glucosides, jasurosides E, F and G, have been isolated from the leaves and stems of Jasminum urophyllum, and their structures established.
- Published
- 1997
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- View/download PDF
42. Three secoiridoid glucosides from Jasminum lanceolarium
- Author
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Ya-Ching Shen, Shao-Ling Lin, and Chyh-Chung Chein
- Subjects
Iridoid ,biology ,medicine.drug_class ,Chemistry ,Stereochemistry ,Plant Science ,General Medicine ,Horticulture ,biology.organism_classification ,Biochemistry ,Chemical correlation ,Dimethyl ester ,chemistry.chemical_compound ,Glucoside ,Secoiridoid Glucosides ,Oleaceae ,medicine ,Spectral analysis ,Molecular Biology ,Jasminum lanceolarium - Abstract
Three new secoiridoid glycosides, jaslanceosides C-E, in addition to jaslanceosides A and B, 10-hydroxyoleoside dimethyl ester and jasminoside were isolated from the leaves and stems of Jasminum lanceolarium. The structures of these compounds were elucidated on the basis of spectral analysis and chemical correlation with known compounds. more...
- Published
- 1997
- Full Text
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43. Antioxidant and anti-inflammatory caffeoyl phenylpropanoid and secoiridoid glycosides from Jasminum nervosum stems, a Chinese folk medicine
- Author
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Ping Li, Jianjun Wang, Yujing Liu, Wen Huang, Bo Liu, Edward J. Kennelly, Shi-Biao Wu, Chunlin Long, Zhiyong Guo, and Ye-Ling Wang
- Subjects
Antioxidant ,medicine.drug_class ,Stereochemistry ,DPPH ,Jasminum ,medicine.medical_treatment ,Anti-Inflammatory Agents ,Plant Science ,Horticulture ,Biochemistry ,Anti-inflammatory ,Antioxidants ,chemistry.chemical_compound ,Verbascoside ,Jasminum nervosum ,Cell Line, Tumor ,medicine ,Humans ,Molecular Biology ,chemistry.chemical_classification ,biology ,Phenylpropanoid ,Molecular Structure ,Glycoside ,General Medicine ,biology.organism_classification ,chemistry ,Oleaceae ,Iridoid Glycosides ,Drugs, Chinese Herbal - Abstract
Eight compounds including four caffeoyl phenylpropanoid glycosides, jasnervosides A-D (1-4), one monoterpenoid glycoside, jasnervoside E (5), and three secoiridoid glycosides, jasnervosides F-H (10-12), were isolated from the stems of Jasminum nervosum Lour. (Oleaceae), along with four known compounds, poliumoside (6), verbascoside (7), alpha-L-rhamnopyranosyl-(1 -> 3)-O-(alpha-L-rhamnopyranosyl(1 -> 6)-1-O-E-caffeoyl-beta-D-glucopyranoside (8), and jaspolyanthoside (9). Their structures were elucidated on the basis of their physicochemical and spectroscopic properties. Compounds 1,2,4 and 11 displayed potent antioxidant activities in the DPPH assay, while 2 and 3 displayed good activities against LPS-induced TNF-alpha and IL-1 beta production in BV2 cells. Compounds 1-5 and 10-12 were evaluated for their cytotoxic activities against three human cancer cell lines (A-549, Bel-7402, and HCT-8), but none displayed significant activity. (C) 2014 Elsevier Ltd. All rights reserved. more...
- Published
- 2013
44. A secoiridoid glucoside from Fraxinus angustifolia
- Author
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Mohammed Hosny, Ihsan Calis, and Mohammed F. Lahloub
- Subjects
biology ,Iridoid ,medicine.drug_class ,Plant Science ,General Medicine ,Fraxinus angustifolia ,Nuezhenide ,Horticulture ,biology.organism_classification ,Biochemistry ,chemistry.chemical_compound ,Glucoside ,chemistry ,Oleaceae ,Botany ,medicine ,Spectral data ,Molecular Biology - Abstract
The known glucoside nuezhenide, and a new secoiridoid glucoside, angustifolioside C [ 6′-O-β- d - glucopyranosyl)-neooleuropein ], were isolated from a methanolic extract of the leaves of Fraxinus angustifolia . Their structures were elucidated on the basis of chemical and spectral data. more...
- Published
- 1996
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45. Biosynthesis of iridoids in Forsythia spp
- Author
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Søren Damtoft, Søren Rosendal Jensen, and Henrik Franzyk
- Subjects
biology ,Chemistry ,Iridoid Glucosides ,Plant Science ,General Medicine ,Deuterium labelled ,Horticulture ,biology.organism_classification ,Biochemistry ,Deoxyloganic acid ,chemistry.chemical_compound ,Forsythia ,Biosynthesis ,Forsythia europaea ,Genus ,Oleaceae ,Botany ,Molecular Biology - Abstract
The biosynthesis of the carbocyclic iridoid glucosides present in the genus Forsythia has been investigated. Deuterium labelled deoxyloganic acid
- Published
- 1994
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46. Secoiridoid glucosides from Fraxinus malacophylla
- Author
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Kenichiro Inoue, Yang Chong-ren, Shinichi Ueda, Masako Akaji, He Zheng-Dan, and Tetsuro Fujita
- Subjects
Iridoid ,biology ,medicine.drug_class ,Stereochemistry ,Plant Science ,General Medicine ,Horticulture ,biology.organism_classification ,Biochemistry ,Tyrosol ,chemistry.chemical_compound ,Fraxinus malacophylla ,Verbascoside ,Glucoside ,chemistry ,Secoiridoid Glucosides ,Oleaceae ,medicine ,Molecular Biology - Abstract
Two new secoiridoid glucosides, butyl isoligustrosidate and fraximalacoside, were isolated from the leaves pf Fraxinus malacophylla, together with the known constituents, isoligustroside, fraxiformoside, isoligustrosidic acid, 1'''-0-beta-D-glucosylfraxiformoside, verbascoside, cosmosiin, sitosterol-beta-D-glucoside and tyrosol. Their structures have been elucidated by chemical and spectroscopic methods. more...
- Published
- 1993
- Full Text
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47. A secoiridoid glucoside and a phenolic compound from Fraxinus ornus bark
- Author
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Tanya Iossifova, Ivanka Kostova, and Bozhana Mikhova
- Subjects
Iridoid ,biology ,medicine.drug_class ,Fraxinus ornus ,Plant Science ,General Medicine ,Horticulture ,biology.organism_classification ,Biochemistry ,Tyrosol ,chemistry.chemical_compound ,chemistry ,Glucoside ,visual_art ,Oleaceae ,Botany ,visual_art.visual_art_medium ,medicine ,Bark ,Phenols ,Molecular Biology - Abstract
A new secoiridoid glucoside named ornoside and a new tyrosol derivative named ornosol have been isolated from Fraxinus ornus bark, along with the k
- Published
- 1993
- Full Text
- View/download PDF
48. Biosynthesis of secoiridoid glucosides in oleaceae
- Author
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Søren Damtoft, Søren Rosendal Jensen, and Henrik Franzyk
- Subjects
Iridoid ,medicine.drug_class ,Plant Science ,General Medicine ,Horticulture ,Biology ,biology.organism_classification ,Biochemistry ,chemistry.chemical_compound ,Phillyrea latifolia ,chemistry ,Biosynthesis ,Glucoside ,Oleuropein ,Oleaceae ,medicine ,Organic chemistry ,Molecular Biology ,Ligustrum ovalifolium ,Syringa josikaea - Abstract
The biosynthesis of the oleoside-type of glucosides (oleosides) has been investigated in two species of Oleaceae, namely Fraxinus excelsior and Syringa josikaea . Deuterated analogues of deoxyloganic acid, 8-epi-deoxyloganic acid, 7-epi-loganic acid and loganic acid were prepared. On administration of the above compounds high incorporations of deoxyloganic acid as well as of loganic acid and its 7-epimer were obtained, strongly implying that 7-ketologanic acid is an intermediate in the biosynthesis of oleosides. The incorporations were measured by 2 H NMR in several isolated secoiridoids all belonging to the oleosides. In addition, the content of acidic iridoids (both carbocyclic and seco-type) in two additional species of Oleaceae, namely Ligustrum ovalifolium and Phillyrea latifolia , were examined. Based on these results, a plausible biosynthetic route from deoxyloganic acid, 7-epi-loganic acid, 7-ketologanic acid, 8-epi-kingisidic acid, oleoside 11-methyl ester, 7-β-1- d -glucopyranosyl 11-methyl oleoside and ligstroside to oleuropein can now be presented. more...
- Published
- 1993
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49. Secoiridoids from Fraxinus angustifolia
- Author
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Sansei Nishibe, Mohammed Hosny, Ihsan Calis, and Taha I. Khalifa
- Subjects
Iridoid ,biology ,medicine.drug_class ,Stereochemistry ,Plant Science ,General Medicine ,Fraxinus angustifolia ,Horticulture ,biology.organism_classification ,Biochemistry ,chemistry.chemical_compound ,chemistry ,Glucoside ,Oleuropein ,Secoiridoid Glucosides ,Oleaceae ,Botany ,medicine ,Molecular Biology - Abstract
A new nonglycosidic secoiridoid, ligstral, and two new secoiridoid diglucosides, angustifolioside A [6″- O -(β- d -glucopyranosyl)-oleuropein] and angustifolioside B [6″- O -(β- d -glucopyranosyl)-ligstroside], were isolated from the methanolic extract of the leaves of Fraxinus angustifolia along with the two known secoiridoid glucosides, ligstroside and oleuropein. The chemical structures of the isolated compounds were established by chemical and spectral evidence. more...
- Published
- 1993
- Full Text
- View/download PDF
50. A secoiridoid glucoside from Fraxinus insularis
- Author
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Hiroshi Kuwajima, Takao Tanahashi, Naotaka Nagakura, Chen Cheng-Chang, Atsuko Shimada, Kenichiro Inoue, and Kiyokazu Takaishi
- Subjects
biology ,Iridoid ,medicine.drug_class ,Plant Science ,General Medicine ,Horticulture ,biology.organism_classification ,Biochemistry ,chemistry.chemical_compound ,Glucoside ,chemistry ,Oleaceae ,Botany ,medicine ,Molecular Biology ,Biogenesis ,Fraxinus insularis - Abstract
A new secoiridoid glucoside, insularoside, was isolated from Fraxinus insularis . The structural elucidation of insularoside by spectroscopic and chemical studies is described. The biogenesis of this glucoside is also briefly discussed. more...
- Published
- 1993
- Full Text
- View/download PDF
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