Alkyl phenols, alkenyl cyclohexenones and other phytochemical constituents from Lannea rivae (chiov) Sacleux (Anacardiaceae) and their bioactivity

Okoth, Dorothy A.; Akala, Hoseah M.; Johnson, Jacob; Koorbanally, Neil A.

doi:10.1007/s00044-016-1521-2

Cited by 15 publications

(14 citation statements)

References 72 publications

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“…Compound 1 (61 mg) was isolated as a yellow oil. The 1 H and 13 C NMR data (Tables 1 and 2) of 1 were consistent with those reported by Okoth et al (2016) for the cardanol, 3-heptadec-12 -Z-enyl phenol [16]. Its molecular formula was obtained as C O, 329.2844).…”

Section: Chemistry Of Isolated Compoundssupporting

confidence: 85%

New Alk(en)ylhydroxycyclohexanes with Tyrosinase Inhibition Potential from Harpephyllum caffrum Bernh. Gum Exudate

Bodede

Moodley

et al. 2022

Molecules

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This work presents the first report on the phytochemical investigation of Harpephyllum caffrum Bernh. gum exudate. A known cardanol, 3-heptadec-12′-Z-enyl phenol (1) and three new alk(en)ylhydroxycyclohexanes, namely, (1R,3R)-1,3-dihydroxy-3-[heptadec-12′(Z)-enyl]cyclohexane (2) (1S,2S,3S,4S,5R)-1,2,3,4,5-pentahydroxy-5-[octadec-13′(Z)-enyl]cyclohexane (3) and (1R,2S,4R)-1,2,4-trihydroxy-4-[heptadec-12′(Z)-enyl]cyclohexane (4) were isolated from the gum. The structures of the compounds were determined by extensive 1D and 2D NMR spectroscopy and HR-ESI-MS data. The ethanolic extract of the gum was found to be the most potent tyrosinase inhibitor with IC50 of 11.32 µg/mL while compounds 2 and 3, with IC50 values of 24.90 and 26.99 µg/mL, respectively, were found to be potential anti-tyrosinase candidates from the gum. Gum exudate may be a potential source for non-destructive harvesting of selective pharmacologically active compounds from plants. The results also provide evidence that H. caffrum gum may find application in cosmetics as a potential anti-tyrosinase agent.

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Section: Chemistry Of Isolated Compoundssupporting

confidence: 85%

New Alk(en)ylhydroxycyclohexanes with Tyrosinase Inhibition Potential from Harpephyllum caffrum Bernh. Gum Exudate

Bodede

Moodley

et al. 2022

Molecules

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“…The 13 C NMR spectrum of 1 (Table 1) exhibited signals for six aromatic carbons (δ C 110.9, 116.0, 122.9, 135.4, 147.9, 163.7), two olefinic carbons (2 × δ C 130.0), one methyl (δ C 14.1), and one carboxylic (δ C 176.1). These data closely resembled those of 3-(14′Z-nonadecenyl)phenol (2) [3], which isolated from the same extract, except for the presence of with those of literature data [3,4]. The configuration of the Δ 14′(15′) double bond was assigned to be Z-configuration on the basis of the 13 C NMR chemical shifts of the methylene carbons adjacent to the double bond [5].…”

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confidence: 83%

A New Alkenylphenol from the Propolis of Stingless Bee Trigona minor

Nguyen

et al. 2018

Natural Product Communications

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A new alkenylphenol, 2-hydroxyl-6-(14' Z -nonadecenyl)benzoic acid (1), was isolated from the ethanolic extract of Vietnamese stingless bee propolis Trigona minor (Meliponini, Apidae), together with two known compounds (2 and 3). Their chemical structures were determined by extensive NMR spectroscopic analysis. All compounds were tested for preferential cytotoxicity against the PANC-1 human pancreatic cell line under nutrition-deprived conditions (NDM). Compound 1 exhibited the strongest preferential cytotoxicity, with a PC50 value of 2.4 μM.

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“…The pure compounds were assayed using a non-radioactive assay technique as described by Smilkstein et al, 2004 [ 32 ] with modifications given in the literature [ 12 , 33 ].…”

Section: Methodsmentioning

confidence: 99%

Four Prenylflavone Derivatives with Antiplasmodial Activities from the Stem of Tephrosia purpurea subsp. leptostachya

et al. 2017

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Four new flavones with modified prenyl groups, namely (E)-5-hydroxytephrostachin (1), purleptone (2), (E)-5-hydroxyanhydrotephrostachin (3), and terpurlepflavone (4), along with seven known compounds (5–11), were isolated from the CH2Cl2/MeOH (1:1) extract of the stem of Tephrosia purpurea subsp. leptostachya, a widely used medicinal plant. Their structures were elucidated on the basis of NMR spectroscopic and mass spectrometric evidence. Some of the isolated compounds showed antiplasmodial activity against the chloroquine-sensitive D6 strains of Plasmodium falciparum, with (E)-5-hydroxytephrostachin (1) being the most active, IC50 1.7 ± 0.1 μM, with relatively low cytotoxicity, IC50 > 21 μM, against four cell-lines.

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Alkyl phenols, alkenyl cyclohexenones and other phytochemical constituents from Lannea rivae (chiov) Sacleux (Anacardiaceae) and their bioactivity

Cited by 15 publications

References 72 publications

New Alk(en)ylhydroxycyclohexanes with Tyrosinase Inhibition Potential from Harpephyllum caffrum Bernh. Gum Exudate

New Alk(en)ylhydroxycyclohexanes with Tyrosinase Inhibition Potential from Harpephyllum caffrum Bernh. Gum Exudate

A New Alkenylphenol from the Propolis of Stingless Bee Trigona minor

Four Prenylflavone Derivatives with Antiplasmodial Activities from the Stem of Tephrosia purpurea subsp. leptostachya

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