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

Chu R, Wan LS, Peng XR, Yu MY, Zhang ZR, Zhou L, Li ZR, Qiu MH - Nat Prod Bioprospect (2016)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China.

ABSTRACT
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.

No MeSH data available.


Related in: MedlinePlus

Key correlations in 2D NMR spectra of compound 4
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Fig3: Key correlations in 2D NMR spectra of compound 4

Mentions: 20-nor-cofaryloside I (4) a white amorphous powder, displayed a [M + Na]+ 357.2032 (calcd for 357.2036) in HREIMS, consistent with the molecular formula of C20H30O4, indicating 6 degrees of unsaturation. The compound 4 displayed similar characteristic signals to 10α,16α,17-trihydroxy-9α-methyl-15-oxo-20-nor-kauran-19-oic acid γ-lactone (A) [16, 17] except for the absence of the carbonyl groups at C-15. This was confirmed by the chemical shift at C-15 (δC 50.9) in 4 which was upfield shifted comparing to that in A (δC 224.0). Besides, the HMBC correlations from H2-15 (δH 1.39, 2.02) to C-16 (δC 84.9) and C8 (δC 43.5) also supported these change. On biogenetic grounds, compound 4 as an ent-kaurane with the configuration of H-5 and H-9 being β-orientated, while OH-10 being α-orientated. Its ROESY correlations showed cross peaks of H-5 (δH 1.94)/Me-18 (δH 1.06), H-5/Me-20 (δH 1.16), Me-20/H-15b (δH 2.02), H-15b/H2-17 (δH 3.64, 3.70), revealing that the orientation of C-18, C-20 and C-17 was β-orientated (Fig. 3). Thereupon, the structure of 4 was identified as 10α,16α,17-trihydroxy-9β-methyl-20-nor-ent-kauran-19-oic acid γ-lactone, and named 20-nor-cofaryloside I.Fig. 3


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

Chu R, Wan LS, Peng XR, Yu MY, Zhang ZR, Zhou L, Li ZR, Qiu MH - Nat Prod Bioprospect (2016)

Key correlations in 2D NMR spectra of compound 4
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4940257&req=5

Fig3: Key correlations in 2D NMR spectra of compound 4
Mentions: 20-nor-cofaryloside I (4) a white amorphous powder, displayed a [M + Na]+ 357.2032 (calcd for 357.2036) in HREIMS, consistent with the molecular formula of C20H30O4, indicating 6 degrees of unsaturation. The compound 4 displayed similar characteristic signals to 10α,16α,17-trihydroxy-9α-methyl-15-oxo-20-nor-kauran-19-oic acid γ-lactone (A) [16, 17] except for the absence of the carbonyl groups at C-15. This was confirmed by the chemical shift at C-15 (δC 50.9) in 4 which was upfield shifted comparing to that in A (δC 224.0). Besides, the HMBC correlations from H2-15 (δH 1.39, 2.02) to C-16 (δC 84.9) and C8 (δC 43.5) also supported these change. On biogenetic grounds, compound 4 as an ent-kaurane with the configuration of H-5 and H-9 being β-orientated, while OH-10 being α-orientated. Its ROESY correlations showed cross peaks of H-5 (δH 1.94)/Me-18 (δH 1.06), H-5/Me-20 (δH 1.16), Me-20/H-15b (δH 2.02), H-15b/H2-17 (δH 3.64, 3.70), revealing that the orientation of C-18, C-20 and C-17 was β-orientated (Fig. 3). Thereupon, the structure of 4 was identified as 10α,16α,17-trihydroxy-9β-methyl-20-nor-ent-kauran-19-oic acid γ-lactone, and named 20-nor-cofaryloside I.Fig. 3

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China.

ABSTRACT
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.

No MeSH data available.


Related in: MedlinePlus