Structure of the 5,6-dihydro-α-pyrone, umuravumbolide

Davies‐Coleman, Michael T.; Rivett, D. E. A.

doi:10.1016/0031-9422(95)93874-f

Cited by 23 publications

(29 citation statements)

References 4 publications

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“…Valued as a traditional remedy throughout its range, this species has been the subject of considerable scientific study. Investigation of secondary chemistry has revealed the presence of diterpenes, for example, ibozol (Zelnik et al, 1978;van Puyvelde et al, 1987) and 7 a-hydroxyroyleanone; a-pyrones, for example, umuravumbolide and tetradenolide (van Puyvelde et al, 1979;Davies-Coleman & Rivett, 1995); and essential oil (1.9%) of which the main components are a-terpineol, fenchone, and b-fenchyl alcohol (Campbell et al, 1997). Some phytosterols have been detected.…”

Section: Lamiaceaementioning

confidence: 99%

A Pharmacognostical Study of 26 South African Plant Species Used as Traditional Medicines

Scott

Springfield

Coldrey

2004

Pharmaceutical Biology

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An estimated 70% of all South Africans use traditional medicines derived from plant species indigenous to the region. In order to formalize the position of these medicines within the state health care system, a necessary first step is the establishment of standards of quality, safety, and efficacy. With this objective in mind, pharmaceutical monographs for 60 plant species used as traditional medicines in South Africa were drawn up according to WHO guidelines. The results of some of this work are reported here, focusing in particular on 26 species belonging to Asteraceae, Geraniaceae, and Lamiaceae, families well represented in indigenous traditional medical practice. Quality standards for the identification of these species, established using high-performance liquid chromatography (HPLC), thin-layer chromatography (TLC), and traditional microscopy, are given. The results of investigations, using the disk assay method, of their efficacy as antimicrobial agents are reported. Secondary chemical profiles, drawn up using standard techniques in pharmacognosy, are shown and discussed with reference to the known bioactivity of each chemical class.

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Section: Lamiaceaementioning

confidence: 99%

A Pharmacognostical Study of 26 South African Plant Species Used as Traditional Medicines

Scott

Springfield

Coldrey

2004

Pharmaceutical Biology

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“…They determined the absolute configuration on the basis of NMR and CD spectral studies and also reported the optical rotations of these compounds. [8] Our continued interest towards the total synthesis of lactone-containing natural products [9] prompted us to undertake the synthesis of demanding targets 1a and 1b. To the best of our knowledge, there is only one report on the synthesis of these natural products by Ramachandran et al [10] who used asymmetric reduction, allylboration, and ring-closing metathesis.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Total Synthesis of Umuravumbolide

Shekhar

Reddy

et al. 2011

Eur J Org Chem

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“…The compounds 8 (14),15-sandaracopimaradiene-2α,18-diol, a diterpenod with antimicrobial activity [5], 5,6-dehydro-α-pyrone (umuravumbolide) [10] and tetradenolide α-pyrone [5] have also been isolated. Although there is broad report on the isolated compounds of T. riparia essential oil, our group still searches for minor constituents that represent a great challenge for researchers.…”

Section: Introductionmentioning

confidence: 99%

New Natural Diterpene-Type Abietane from Tetradenia riparia Essential Oil with Cytotoxic and Antioxidant Activities

et al. 2014

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Tetradenia riparia (Hochstetter) Codd belongs to the Lamiaceae family and it was introduced in Brazil as an exotic ornamental plant. A previous study showed its antimicrobial, acaricidal and analgesic activities. Two compounds were isolated from essential oil of T. riparia leaves and identified as 9β,13β-epoxy-7-abietene (1), a new one, OPEN ACCESSMolecules 2014, 19 515 and 6,7-dehydroroyleanone (2), already reported for another plant. The structure of these compounds was determined by spectroscopic analysis and by comparison with literature data. The cytotoxic activities of the essential oil and compounds 1 and 2 were determined by a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, and by tumor cells MDA-MB-435 (human breast carcinoma), HCT-8 (human colon), SF-295 (human nervous system) and HL-60 (human promyelocytic leukemia). The essential oil and compound 1 showed high cytotoxic potential of the cell lines SF-295 (78.06% and 94.80%, respectively), HCT-8 (85.00% and 86.54%, respectively) and MDA-MB-435 (59.48% and 45.43%, respectively). Compound 2 had no cytotoxic activity. The antioxidant activity was determined by 2,2-diphenyl-1-picryl-hydrazyl (DPPH), β-carotene-linoleic acid system and 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. The inhibitory concentration (IC 50 in µg mL −1 ) for essential oil and compound 2 was, respectively 15.63 and 0.01 for DPPH; 130.1 and 109.6 for β-carotenelinoleic acid and 1524 and 1024 for ABTS. Compound 1 had no antioxidant activity. By fractioning the oil, it was possible to identify two unpublished compounds: 1 with high cytotoxic potential and 2 with high antioxidant potential.

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Structure of the 5,6-dihydro-α-pyrone, umuravumbolide

Cited by 23 publications

References 4 publications

A Pharmacognostical Study of 26 South African Plant Species Used as Traditional Medicines

A Pharmacognostical Study of 26 South African Plant Species Used as Traditional Medicines

Stereoselective Total Synthesis of Umuravumbolide

New Natural Diterpene-Type Abietane from Tetradenia riparia Essential Oil with Cytotoxic and Antioxidant Activities

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