Tirucallane-type triterpenoids: nmr and X-ray diffraction analyses of 24-epi-piscidinol A and piscidinol A

McChesney, James D.; Dou, Jinhui; Sindelar, Robert D.; Goins, D K; Walker, Larry; Rogers, Robin D.

doi:10.1007/bf02575975

Cited by 39 publications

(31 citation statements)

References 17 publications

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“…Comparison with the CD experimental and ECD calculated data, revealed that the established 5R,9R,10R,13S,14R,17R-stereoisomer of 1 and 3R,5R,9R,10R,13S,14R,17S-stereoisomer of 2 are in agreement with the stereochemistries proposed by the NMR data, and consistent with those of related triterpenoids reported previously [22].…”

Section: And Ecdsupporting

confidence: 91%

Spectroscopic characterizations, X-ray studies, and electronic circular dichroism calculations of two alkaloid triterpenoids

et al. 2011

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Two alkaloid triterpenoids formulated as C 26 H 35 NO 3 (1) and C 30 H 45 NO 2 (2) were isolated from the timer tree Aphanamixis grandifolia. The structure of 1 and 2 was determined by IR, HRESIMS, 1D, and 2D-NMR. Compound 1 was confirmed by X-ray single crystal diffraction. Compound 1 crystallizes in the monoclinic, space group C 2 with unit cell parameters a = 53.195(4) Å , b = 7.6339(8) Å , c = 11.202(2) Å , b = 94.6520(2)°. Intermolecular hydrogen bonding and p-p stacking were presented in the molecular packing of 1. The absolute configurations of 1 and 2 were established by comparison of experimental circular dichroism properties with their electronic circular dichroism predicted by molecular modeling DFT calculations.

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Section: And Ecdsupporting

confidence: 91%

Spectroscopic characterizations, X-ray studies, and electronic circular dichroism calculations of two alkaloid triterpenoids

et al. 2011

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“…However, the assignment of a relative configuration of the side chain with three OH groups represented a special problem. Fortunately, a few compounds, especially the four-ring triterpenoid and steroid with the same problem, have been recently resolved by X-ray, chemical methods, and using the coupling constant of H and C, [20][21][22]. The relative configurations of OH-23 and OH-24 should be threo or erythro, and each configuration should show the same NMR pattern.…”

Section: Resultsmentioning

confidence: 99%

Cycloartane Triterpenoids fromCassia occidentalis

Li¹,

Di²,

Luo³

et al. 2012

Planta Med

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A phytochemical investigation of the whole plants of Cassia occidentalis led to the isolation of two new cycloartane triterpenoids, cycloccidentalic acids A and B (1 and 2), and five new related saponins, cycloccidentalisides I-V (3-7), together with sixteen known compounds. The structures of the isolated compounds were elucidated through detailed spectroscopic analyses, including 1D and 2D NMR techniques, and chemical methods. Compounds 2 and 5 showed modest anti-HIV-1 activities with EC₅₀ values of 2.23 µM and 4.36 µM, respectively, in comparison to the positive control.

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“…Compounds 10-15 were identified as sapelin E acetate, 5) grandifoliolenone, 6) azadirone, 7) bourjotinolone A, 8) piscidinol A, 9) and hispidol B, 10) respectively, by the analysis of their spectroscopic data. Full 1 H-and 13 C-NMR data for 10 and 11 are provided in Experimental.…”

Section: H-mentioning

confidence: 99%

Apotirucallane and Tirucallane Triterpenoids from Cedrela sinensis

Mitsui

Saito

Yamamura

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Cedrela sinensis JUSS. (Meliaceae) has been used in mainland China and Korea as a traditional medicine for the treatment of enteritis, dysentery, and itching. Previously, from the seeds, leaves, stems, and cortex of this plant, we reported on five obacunone-type limonoids, 1) twenty-three apotirucallane-type triterpenoids, 2) and seven gedunin-type limonoids.3) In the present study, from the cortex of this plant, we isolated nine new apotirucallane and tirucallane triterpenoids along with six known compounds and determined their structures (Fig. 1).By a series of column chromatography including Diaion HP-20, activated charcoal, and ODS column chromatogra- Nine new triterpenoids, 1-9, were isolated from the cortex of Cedrela sinensis (Meliaceae), together with six known compounds, sapelin E acetate, grandifoliolenone, azadirone, bourjotinolone A, piscidinol A, and hispidol B. The structures of 1-9 were determined by the 2D NMR experiments, chemical methods, and X-ray crystallography.

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Tirucallane-type triterpenoids: nmr and X-ray diffraction analyses of 24-epi-piscidinol A and piscidinol A

Cited by 39 publications

References 17 publications

Spectroscopic characterizations, X-ray studies, and electronic circular dichroism calculations of two alkaloid triterpenoids

Spectroscopic characterizations, X-ray studies, and electronic circular dichroism calculations of two alkaloid triterpenoids

Cycloartane Triterpenoids fromCassia occidentalis

Apotirucallane and Tirucallane Triterpenoids from Cedrela sinensis

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