Isolation and characterization of six labdane diterpenes and one pregnane steroid of Turraeanthus africanus

Chenda, Laurice Bracine Njanang; Kouam, Siméon F.; Lamshöft, Marc; Kusari, Souvik; Talontsi, Ferdinand Mouafo; Ngadjui, Bonaventure T.; Spiteller, Michael

doi:10.1016/j.phytochem.2014.03.022

Cited by 14 publications

(5 citation statements)

References 19 publications

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“…Ex C.DC.) Pellegr., and Aglaia grandis, respectively [3,6,[59][60][61][62][63][64][65][66]. Another three compounds of this type, 14-hydroxyelemol (37), β-eudesmol (38), and cryptomeridiol (39), have been obtained from the stems of Trichilia claussenii; their structure was elucidated by the basis of spectroscopic analysis [47].…”

Section: Bicyclic Sesquiterpenoidsmentioning

confidence: 99%

Sesquiterpenoids from Meliaceae Family and Their Biological Activities

2023

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Sesquiterpenoids, an important class of natural products possessing three isoprene-derived units, are widely distributed across plants and have a variety of biological activities. All sesquiterpenoids are derived from farnesyl pyrophosphate (FPP), a biosynthesis precursor that can form various carbon skeletons. In order to provide a reference for further research and development of these compounds, this review focused on the increasing number of isolated and volatile sesquiterpenoids found to be produced by plants of the Meliaceae family between 1968 and 2023. The related articles were collected from SciFinder, Google Scholar, and PubMed. According to a literature review, several studies were started for more than 55 years on the plant’s stem barks, twigs, leaves, flowers, seeds, and pericarps, where approximately 413 sesquiterpenoid compounds from several groups such as eudesmane, aromadendrane, cadinane, guaiane, bisabolane, furanoeremophilane, humulene, germacrane, and oppositane-type were isolated and identified with some minor products. Additionally, the hypothetical route of sesquiterpenoids biosynthesis from this family was identified, and eudesmane-type was reported to be 27% of the total compounds. The antimicrobial, antidiabetic, antioxidant, antiplasmodial, antiviral, and cytotoxic activities of the isolated compounds and major volatile sesquiterpenoids constituent on essential oil were also evaluated. The result showed the fundamental of using the sesquiterpenoid compounds from the Meliaceae family in traditional medicine and the discovery of new drugs.

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Section: Bicyclic Sesquiterpenoidsmentioning

confidence: 99%

Sesquiterpenoids from Meliaceae Family and Their Biological Activities

2023

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“…Unfortunately, this possible labdane diterpene which named turraeanin J presents with little available online data and isolated only in one research that identified this compound by high resolution-mass spectrometry and results in m/z 337.2 with no details on the other possible fragments. 24 Another analysis for the isolated C1 compound has been done by FT-IR that reveals several absorptive peaks among which 3375 cm -1 could be related to the O-H stretching, 3088 cm -1 might be for the O-H stretching of carboxylic acid, and 1691 cm -1 the distinctive area of C=O stretching. It is worthy to note that the research mentioned this possible diterpene describing its nature as yellow oil (droplets) and observed after isolation and dryness of the isolated C1 compound.…”

Section: Identification Of Isolated Compound C1mentioning

confidence: 99%

Isolation of Three Secondary Metabolites from the Eucalyptus camaldulensis Dehnh. Plant for the First Time

Al-Tameemi¹,

Hamad²

2022

IJDDT

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Objectives: Phytochemical screening and identification of certain types of secondary metabolites that not separated yet from the Eucalyptus camaldulensis plant. Background: E. camaldulensis Dehnh. (Family: Myrtaceae) is one of the most widely distributed species of eucalyptus trees and the original land of this variety is Australia. E. camaldulensis Dehnh. is the main species that distributed in various regions of Iraq. E. camaldulensis has active constituents rich in pharmacologically significant secondary metabolites with proven activities including anti-bacterial, anti-fungal, anti-viral, anti-oxidant, and others. Methodology: Defatting step of leaves and fruits separately with n-hexane was preceding the extraction process by maceration with 50% acetone followed by subsequent fractionation process and isolation step achieved by thin-layer chromatography (TLC) and high-performance liquid chromatography (HPLC). Results: The resulting three fractions had been undergone preliminary chemical tests suggesting the presence of steroids, terpenoids, and tannins. The isolation process had been given rise to the separation of three phytoconstituents identified by different chromatographic techniques resulting in the confirmation of the non-polar compounds isolated from the hexane fraction comprising the phytosterol stigmasterol and the possible diterpene turraeanin J. The polar secondary metabolite isolated from the ethyl acetate fraction is the dimer tannin oenothein B. Conclusion: The Iraqi E. camaldulensis plant rich in various secondary metabolites presents diverse pharmacological activities. The first isolation might be around the world from the Eucalyptus genus, is the expected diterpene turraeanin J, and the first isolation from the species around the world are oenothein B and stigmasterol.

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“…Many phytochemical studies of this genus have been reported. Several terpenoids, mainly limonoids and protolimonoids, were isolated from Turraea pubescens , − Turraea mannii , − Turraea floribunda , − Turraea africanus , − Turraea wakefieldii , , Turraea parvifolia , − Turraeaholstii , , Turraea obtusifolia, Turraea nilotica , and others. A 50% MeOH/CH 2 Cl 2 extract of T. delphinensis (N133535–O/6) collected in Madagascar exhibited potent cytotoxicity in NCI-60 human tumor cell line screening.…”

mentioning

confidence: 99%

“…Spectroscopic identification revealed that the newly isolated terpenoids presented four skeletons: cycloartanes 1−6, tirucallanes/euphanes 7−10, limonoids 11−13, and sterol 14. The known terpenoids were identified as cneorin-NP 36 (15), 26 tirucalla-7,24-dien-3-one (16), 27 butyrospermol (17), 28 kumuquassin E (18), 29 3-oxotirucalla-7,24-dien-23-ol (19), 27 tirucalla-7,24-dien-3β,23-diol (20), 30 niloticin (21), 31 dihydroniloticin (22), 26 piscidinol A (23), 32 hispidol B (24), 33 bourjotinolone A (25), 34 hispidone (26), 34 dymacrin G (27), 35 24-en-cycloartanone (28), 36 cycloartenol (29), 37 cycloart-24-en-3,23-dione (30), 38 3β-hydroxy-cycloart-24-en-23-one (31), 39 21-carbomethoxy-cycloart-24-en-3-one (32), 40 (23R)-21,23-epoxy-5α-cycloart-24-en-3-one (33), 41 (23S)-21,23-epoxy-5α-cycloart-24-en-3-one (34), 41 21-hydoroxycycloart-24-en-3-one (35), 40 aphagrandinoid D (36), 42 hirtinone (37), 43 25-hydroxycycloart-23-en-3-one (38), 44 (23E)-cycloart-23-en-3α,25-diol (39), 45 3-oxo-5α-cycloart-24en-21-al (40), 41 (23R)-cycloart-24-en-3β,23-diol (41), 46 hydroxydammarenone-I (42), 47 hydroxydammarenone-II (43), 47 β-sitostenone…”

mentioning

confidence: 99%

Isolation, Characterization, and Antiproliferative Activity of Terpenoids from the Tropical Plant Turraea delphinensis

Kouno,

Amuti,

Saito

et al. 2024

J. Nat. Prod.

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The isolation, structure determination, and biological evaluation of constituents from the organic extract of Turraea delphinensis Wahlert (Meliaceae) resulted in the isolation of 51 secondary metabolites, including 14 new terpenoids (six cycloartanes, four tirucallanes/euphanes, three limonoids, and a 7-keto sterol). Among the new compounds, 1 is the first triterpenoid with a trioxaspiro[4.4]nonane side chain, while 11−13 are the first 17-γ-lactone tetranortriterpenoids with four oxygenated functional groups at C-1, -3, -6, and -7. The isolated compounds were evaluated for antiproliferative activity against five human tumor cell lines, including a vinblastineresistant cell line.

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Isolation and characterization of six labdane diterpenes and one pregnane steroid of Turraeanthus africanus

Cited by 14 publications

References 19 publications

Sesquiterpenoids from Meliaceae Family and Their Biological Activities

Sesquiterpenoids from Meliaceae Family and Their Biological Activities

Isolation of Three Secondary Metabolites from the Eucalyptus camaldulensis Dehnh. Plant for the First Time

Isolation, Characterization, and Antiproliferative Activity of Terpenoids from the Tropical Plant Turraea delphinensis

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