Volatile Constituents of the Flower Concrete of<i>Gardenia taitensis</i>DC

Claude-Lafontaine, Angélina; Raharivelomanana, Phila; Bianchini, Jean‐Pierre; Schippa, Christine; Azzaro, Maurizio; Cambon, A.

doi:10.1080/10412905.1992.9698082

Cited by 9 publications

(4 citation statements)

References 5 publications

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“…Compound 2 has already been isolated from the flower of Gardenia taitensis DC, 2) however no NMR spectral data has been reported. with the IC 50 values ranging from 5.36 to 11.41 mg/ml (Table 2).…”

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COX-1, COX-2 Inhibitors and Antifungal Agents from Croton hutchinsonianus

et al. 2006

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Croton hutchinsonianus HOSSEUS belongs to the family Euphorbiaceae. It is a shrub or small tree reaching 4-5 meters high and native to Thailand,1) where it is commonly called "Plao phae". In this paper, we describe the isolation and structure elucidation of newly isolated 3Ј-(4Љ-hydroxy-3Љ,5Љ-dimethoxyphenyl)-propyl benzoate, 3Ј-(4Љ-hydroxyphenyl)-propyl benzoate and four known compounds [3Ј-(4Љ-hydroxy-3Љ-methoxyphenyl)-propyl benzoate, poilaneic acid, farnesyl acetone and 4-hydroxybenzaldehyde] from the branches of this plant. The complete NMR assignment of 3Ј-(4Љ-hydroxy-3Љ-methoxyphenyl)-propyl benzoate was established for the first time in this paper. The inhibitory activities against the enzymes COX-1 and COX-2 and antifungal activities against Candida albicans were also performed on some of the isolated products. Results and DiscussionCompounds 1-6 were obtained from the ethyl acetate extract of C. hutchinsonianus after purification by Cosmosil C 18 -OPN, Sephadex LH 20 and silica gel column chromatography.HR-FAB-MS of 1 suggested a molecular formula of C 18 H 20 O 5 corresponding to nine degrees of unsaturation present in the molecule. The IR spectrum demonstrated the presence of a hydroxyl group (3446 cm Ϫ1) and a carbonyl group (1708 cm Ϫ1 ). The 1 H-NMR spectral data (Table 1) showed the presence of two benzene rings which was readily confirmed by analysis of the 1 H-1 H COSY, HMQC and HMBC spectral data. The 1 H-NMR spectral data showed three methylene groups (H-1Ј, H-2Ј, H-3Ј) bridging between benzoate and aromatic rings, two methoxyls at d 3.86 (each 3H, s) and one D 2 O-exchageable hydroxyl proton at d 5.40 appearing as a broad singlet suggestive of the phenylpropyl benzoate moiety with the substituents of hydroxyl and methoxyl groups on the aromatic ring. In addition, HMBC data for 1 conclusively demonstrated the correlations of methylene protons H-1Ј to C-1 and H-2Ј to C-1Љ and H-3Ј to C-2Љ and C-1Ј respectively. The 13 C-NMR spectrum showed the signal of carbonyl ester at d 166.6. The positions of two methoxyl groups and one hydroxyl group were established employing the HMBC technique (correlations as shown in Fig. 1). All data are consistent with the structure of 3Ј-(4Љ-hydroxy-3Љ,5Љ-dimethoxyphenyl)-propyl benzoate.Compound 2 has already been isolated from the flower of Gardenia taitensis DC, 2) however no NMR spectral data has been reported. The 1 H-and 13 C-NMR data of 2 are shown in Table 1.Compound 3 had a molecular formula of C 16 H 16 O 3 based on HR-FAB-MS. The 1 H-and 13 C-NMR data of 3 (Table 1) was similar to those of 1 except for the absence of two methoxyl groups at C-5Љ and C-3Љ. The 1 H-NMR spectral data of 3 showed the presence of the para-substituted benzene ring at d 7.08 (2H, d, Jϭ8.4 Hz, H-2Љ, H-6Љ); d 6.77 (2H, d, Jϭ8.4 Hz, H-3Љ, H-5Љ). The 2D NMR experiment on 3 also produced very similar results, indicating that both 1 and 3 were closely related.Compounds 1-3 were tested for antifungal activity against Candida albicans. They showed moderate activity * To whom corresponde...

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COX-1, COX-2 Inhibitors and Antifungal Agents from Croton hutchinsonianus

et al. 2006

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“…We postulated that these are most likely esters of ( Z )‐hex‐3‐en‐1‐ol and geraniol because the corresponding alcohols occur in notable quantities in all samples (1–8.3% and 0.5–0.8%, respectively), whereas their diastereomers are significantly less abundant or entirely absent. Such esters are known natural products, 42–45 but none of the reported RIs matched, 46 suggesting the presence of previously unknown homologs. We estimated that the determined RIs would correlate well with ( Z )‐hex‐3‐en‐1‐yl eicosanoate ( 1 ), ( Z )‐hex‐3‐en‐1‐yl docosanoate ( 2 ) and geranyl heneicosanoate ( 3 ) and subsequently synthesized these three new natural products by simple Steglich esterification procedures.…”

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confidence: 97%

New esters from the essential oil of dry flowers of elder (Sambucus nigra L.)

Raičević,

Mladenović,

Aćimović

et al. 2023

J Sci Food Agric

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BackgroundElder (Sambucus nigra L.) has relevance for the food, fragrance and pharmaceutical industries. Flowers of this species emit a very pleasant scent; for processing purposes, inflorescences are either collected from the wild or harvested from a cultivated crop. The study of elderflower‐derived volatiles bears both phytochemical and commercial importance.ResultsThree samples of dry elderflower essential oil obtained from laboratory‐scale hydrodistillations were analyzed. By use of GC‐MS, synthesis and NMR studies of chromatographic fractions of a distillation water extract prepared in a semi‐industrial scale steam distillation, a total of 252 constituents of the oil were identified; 115 compounds were not previously reported as elderflower volatiles, seven of which were new natural esters. Particularly interesting were those of isosenecioic (3‐methylbut‐3‐enoic) acid, as these were never before found in the plant kingdom.ConclusionWith these identifications, the known essential oil constituents accounted for 89.0–93.0% of the analyzed samples. While the number of known S. nigra flower‐derived volatiles is now quite high, further research, both analytical and olfactory, is needed to unveil all of the relevant contributions to the unique odor of elderflowers.This article is protected by copyright. All rights reserved.

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“…To the best of our knowledge, no pharmacological studies have been published on G. taitensis . However, over 150 volatile compounds have been isolated from the flowerbuds including linalool and isoeugenol (compounds with antimicrobial activities), along with salicylate derivatives (compounds with anti-inflammatory and analgesic activities) [ 138 ]. Altogether, G. taitensis present ethnobotanical and phytochemical evidence of efficacy in inflammatory and infectious skin disorders, while P. glabra present pharmacological evidence of efficacy in inflammatory and anti-infectious disorders.…”

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confidence: 99%

Traditional medical practices for children in five islands from the Society archipelago (French Polynesia)

Chassagne,

Butaud,

et al. 2023

J Ethnobiology Ethnomedicine

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Background Traditional Polynesian medicine for children has been poorly documented, and few data are available on their efficacy and safety. In this context, the aim of this study was to identify traditional practices used for treating children and then assess the efficacy and safety of the most cited remedies by reviewing the literature. Methods In 2022, a semi-structured survey was carried out on five islands from the Society archipelago (Bora Bora, Huahine, Moorea, Raiatea, and Tahiti). A total of 86 participants were interviewed including 19 experts in herbalism. A thorough literature review was performed on the most cited plant species to gather the relevant ethnobotanical, pharmacological, and clinical data of each remedy. Results Participants mentioned using 469 remedies to treat 69 health disorders. The most represented health categories were digestive system, skin disorders, infectious diseases, and respiratory system. A total of 67 plant species (representing 731 use-reports) were mentioned and Annona muricata, Gardenia taitensis, and Hibiscus rosa-sinensis were the main plants reported. Regarding the safety of cited remedies, one plant (Microsorum grossum) showed high risk of toxicity, and its use should be avoided in infants and children. Conclusion Our survey confirms the importance of traditional medical practices for children in the Society Islands. A lack of data in children for most cited remedies demonstrate the need for more pharmacological and toxicological research on Polynesian medicinal plants. Finally, the potential risk of toxicity for some cited plant species reported calls for a better information of traditional medicine users and healers.

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Volatile Constituents of the Flower Concrete ofGardenia taitensisDC

Cited by 9 publications

References 5 publications

COX-1, COX-2 Inhibitors and Antifungal Agents from Croton hutchinsonianus

COX-1, COX-2 Inhibitors and Antifungal Agents from Croton hutchinsonianus

New esters from the essential oil of dry flowers of elder (Sambucus nigra L.)

Traditional medical practices for children in five islands from the Society archipelago (French Polynesia)

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