Bengalensol, a New 16-epicafestol Derivative from the Leaves of<i>Coffea Bengalensis</i>

Hasan, Choudhury M.; Huda, Quamrul; Lavaud, Catherine; Connolly, Joseph D.; Haque, Md. Enamul

doi:10.1080/10575639408043935

Cited by 8 publications

(4 citation statements)

References 7 publications

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“…The identity was confirmed by UPLC-ToF-MS and NMR experiments. The spectroscopic data were in excellent accordance with the published data . UV (H 2 O/ACN/formic acid 67/32.9/0.1, v/v/v) 280 nm; UPLC-ToF-MS (ESI + ) found m / z 329.1753, calcdd 329.1753 (Δ 0.1 mDa) for C 20 H 25 O 4 ([M + H] + ); 1 H NMR (MeOD, 500 MHz) δ 1.05 (3H, s, H20), 1.33 (1H, m, H12a), 1.50–1.68 (4H, m, H6a, H7a, H15a, H15b), 1.82 (1H, m, H7b), 1.89 (1H, m, H14a), 2.02 (1H, m, H9), 2.08–2.15 (2H, m, H12b, H14b), 2.55–2.57 (2H, m, H1a, H13), 2.66 (1H, d, J = 16.0 Hz, H1b), 2.91 (1H, dd, J = 12.2, 2.1 Hz, H5), 3.60 (1H, d, J = 11.8 Hz, H17a), 3.69 (1H, d, J = 11.8 Hz, H17b), 4.44 (1H, bs, H11), 6.60 (1H, d, J = 1.7 Hz, H18), 7.80 (1H, d, J = 1.7 Hz, H19); 13 C NMR (MeOD, 125 MHz) δ 16.1 (C20, CH3), 22.2 (C6, CH2), 36.8 (C7, CH2), 40.3 (C14, CH), 42.4 (C13, CH2), 43.3 (C10, C), 43.6 (C12, CH2), 44.7 (C8, C), 45.9 (C5, CH), 52.9 (C15, CH2), 53.9 (C1, CH2), 56.1 (C9, CH), 65.1 (C17, CH2), 77.5 (C11, CH), 90.0 (C16, C), 110.8 (C18, CH), 143.0 (C4, C), 146.0 (C3, C), 149.5 (C19, CH), 186.0 (C2, C).…”

Section: Methodssupporting

confidence: 86%

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Numerous Compounds Orchestrate Coffee’s Bitterness

Lang

Pizio

et al. 2020

J. Agric. Food Chem.

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Coffee is one of the most consumed hot beverages worldwide and is highly regarded because of its stimulating effect despite having a pronounced bitterness. Even though numerous bitter ingredients have been identified, the detailed molecular basis for coffee’s bitterness is not well understood except for caffeine, which activates five human bitter taste receptors. We elucidated the contribution of other bitter coffee constituents in addition to caffeine with functional calcium imaging experiments using mammalian cells expressing the cDNAs of human bitter taste receptors, sensory experiments, and in silico modeling approaches. We identified two human bitter taste receptors, TAS2R43 and TAS2R46, that responded to the bitter substance mozambioside with much higher sensitivity than to caffeine. Further, the structurally related bitter substances bengalensol, cafestol, and kahweol also activated the same pair of bitter taste receptors much more potently than the prototypical coffee bitter substance caffeine. However, for kahweol, a potent but weak activator of TAS2R43 and TAS2R46, we observed an inhibitory effect when simultaneously applied together with mozambioside to TAS2R43 expressing cells. Molecular modeling experiments showed overlapping binding sites in the receptor’s ligand binding cavity that suggest that the partial agonist kahweol might be useful to reduce the overall bitterness of coffee-containing beverages. Taken together, we found that the bitterness of coffee is determined by a complex interaction of multiple bitter compounds with several human bitter taste receptors.

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Section: Methodssupporting

confidence: 86%

“…The spectroscopic data were in excellent accordance with the published data. 18 UV (H 2 O/ACN/formic acid 67/32.9/0. Functional Calcium Mobilization Assay.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Numerous Compounds Orchestrate Coffee’s Bitterness

Lang

Pizio

et al. 2020

J. Agric. Food Chem.

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“…With the exception of the glycoside moiety, the connecting carbon C11 (74.5 ppm), and the quaternary carbon C16 (83.8 ppm), the chemical shifts of target compound 3 were in good accordance with those reported for bengalensol, which has been isolated from the leaves of Coffea bengalensis. 20 Considering the glycosidic nature of 3, the HDMS data of both intact and fragmented pseudomolecular ion, and the NMR spectroscopic data, compound 3 was unequivocally identified as the furokaurane glucoside 11-O-(β-D-glucopyranosyl)-cafestol-2one, also reported as mozambioside (cf. Figure 3), which has been isolated from seeds of C. arabica 21 as well as the wild coffee species Coffea pseudozanguebariae.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Mozambioside Is an Arabica-Specific Bitter-Tasting Furokaurane Glucoside in Coffee Beans

Lang

Klade

Beusch

et al. 2015

J. Agric. Food Chem.

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Sensory-guided fractionation of a roasted coffee beverage revealed a highly polar, bitter-tasting subfraction, from which the furokaurane glucoside mozambioside was isolated and identified in its chemical structure by means of HDMS and NMR spectra. Sensory evaluation revealed a bitter taste recognition threshold of 60 (± 10) μmol/L. UPLC-HDMS quantitation of raw coffee beans showed that Arabica coffees contained 396-1188 nmol/g mozambioside, whereas only traces (<5 nmol/g) were detected in Robusta coffees, thus suggesting that mozambioside can be used as an analytical marker for Arabica coffee. Roasted Arabica contained a substantially reduced concentration (232 ± 37 nmol/g), indicating partial degradation of mozambioside during coffee roasting. Mozambioside was nearly quantitatively extracted into the aqueous brew during coffee-making (86-98%).

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“…Seven known diterpenoids were also obtained from this genus, bengalensol [18], villanovane [10], tricalysione A [14], 2 β ,16 α ,17-trihydroxy- ent -kauran-19 α -oic acid [19], 2-O-(2-O-isovaleryl- β - d -gluco-pyranosyl)-4 α -atractyligenin [20], 2-O-(2-O-isovaleryl- β - d -gluco-pyranosyl)-4 β -atrac- tyligenin [20], 3-O- β - d -glucopyranosyl-2-O-(2-O-isovaleryl- β - d -gluco-pyranosyl)-4 β -atracty ligenin [20]. Their structures were identified by comparison of their NMR data with literature data.…”

Section: Resultsmentioning

confidence: 99%

Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans

Chu

Wan

Peng

et al. 2016

Nat. Prod. Bioprospect.

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Five new ent-kaurane diterpenoids, named mascaroside III–V (1–3), and 20-nor-cofaryloside I–II (4–5), together with seven known diterpenoids, were isolated from methanol extracts of the green coffee beans of Yunnan Arabica Coffee. Their chemical structures were elucidated by extensive spectroscopic analyses. Meanwhile, cytotoxicity assay against HL-60, A-549, SMMC-7721, MCF-7 and SW480 cell lines showed that they have not evident inhibition of cytotoxicity.Graphical AbstractElectronic supplementary materialThe online version of this article (doi:10.1007/s13659-016-0099-1) contains supplementary material, which is available to authorized users.

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Bengalensol, a New 16-epicafestol Derivative from the Leaves ofCoffea Bengalensis

Cited by 8 publications

References 7 publications

Numerous Compounds Orchestrate Coffee’s Bitterness

Numerous Compounds Orchestrate Coffee’s Bitterness

Mozambioside Is an Arabica-Specific Bitter-Tasting Furokaurane Glucoside in Coffee Beans

Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans

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