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Bioactivity guided separation of Walsura trichostemon stem methanolic extract led to the isolation of four new dammarane (1–4) and two new apotirucallane triterpenoids (5–6), together with one limonoid (7), 11,25-dideacetyltrichostemonate, 12β, 20S, 24R-trihydroxydammar-25-en-3-one and 12β, 20S, 25-trihydroxydammar-23-en-3-one. Compounds 1–7 showed in vitro inhibitory activity on the proliferation of A549, human lung adenocarcinoma cell line. [ABSTRACT FROM AUTHOR]

Ten new triterpenoid compounds with structure diversity of the C-17 side-chain, including nine tirucallanes, named xylocarpols A⁻E (1⁻5) and agallochols A⁻D (6⁻9), and an apotirucallane, named 25-dehydroxy protoxylogranatin B (10), were isolated from the mangrove plants Xylocarpus granatum, Xylocarpus moluccensis, and Excoecaria agallocha. The structures of these compounds were established by HR-ESIMS and extensive one-dimensional (1D) and two-dimensional (2D) NMR investigations. The absolute configurations of 1 and 2 were unequivocally determined by single-crystal X-ray diffraction analyses, conducted with Cu Kα radiation; whereas those of 4, 6⁻8 were assigned by a modified Mosher’s method and the comparison of experimental electronic circular dichroism (ECD) spectra. Most notably, 5, 6, 7, and 9 displayed potent activation effects on farnesoid⁻X⁻receptor (FXR) at the concentration of 10.0 μM; 10 exhibited very significant agonistic effects on pregnane⁻X⁻receptor (PXR) at the concentration of 10.0 nM.

Nine undescribed protolimonoids, including two apotirucallane and seven tirucallane triterpenoids, as well as five known compounds, were isolated from the root bark of Dictamnus dasycarpus Turcz. Their structures were elucidated by extensive spectroscopic analysis. Compounds 4 – 8, with an undescribed 22,25-epoxytirucallene part, were established their absolute configuration by single-crystal X-ray diffraction of 4. Such compounds might provide evidence for the degradation of protolimonoids to limonoids, bridging an oxidative cleavage biogenetic pathway between these structurally diverse triterpenoids. None of them showed anti-inflammatory, hepatoprotective, or monoamine oxidase B inhibitory activity. Nine undescribed protolimonoids together with five known compounds were isolated from the root bark of Dictamnus dasycarpus Turcz. In addition, proposed biosynthetic pathway of protolimonoids C-17 moiety was discussed in this paper [Display omitted] [ABSTRACT FROM AUTHOR]

Extensive phytochemical investigation on the methanol extract of the inflorescences, twigs, and leaves of Brucea javanica led to the isolation and identification of 27 triterpenoids, including21 previously undescribed ones, named brujavanoids A–U (1 – 21). Their structures were determined based on comprehensive spectroscopic analysis and single-crystal X-ray diffraction. Of these compounds, brujavanoid A (1) represents the first apotirucallane-type triterpenoid with a novel 19(10→9) abeo motif, and brujavanoids B and C (2–3) are the first apotirucallane-type triterpenoids with a rarely occurring 14-hydorxy-15,16-epoxy fragment. All the isolates were evaluated for their anti-inflammatory effect in an LPS-activated RAW264.7 cells model. Furthermore, the most active one, brujavanoid E (5), can suppress the transcriptional expression of typical proinflammatory mediators and inhibit the nuclear translocation of NF- κ B p65 in the LPS- activated RAW264.7 cells. [Display omitted] • 27 Apotirucallane-type triterpenoids including 21 undescribed ones were isolated from Brucea javanica. • The absolute configurations of compounds 1 – 2 , 6 , 18 and 11 were established by X-ray diffraction. • Compound 1 represents the first apotirucallane-type triterpenoid with a novel 19(10 → 9)abeo motif. • Compounds 2 and 3 are the first apotirucallane-type triterpenoids with a rarely occurring 14-hydorxy-15,16-epoxy fragment. • Compounds 5 , 7 , 16 , and 20 displayed moderate to significant anti-inflammatory effect. • Compound 5 can suppress the transcriptional expression of typical pro-inflammatory mediators and inhibit the nuclear translocation of NF- κ B p65. Extensive phytochemical investigation on the methanol extract of the inflorescences, twigs, and leaves of Brucea javanica led to the isolation and identification of 27 triterpenoids, including 21 previously undescribed ones, named brujavanoids A–U (1 – 21). Their structures were determined based on comprehensive spectroscopic analysis and single-crystal X-ray diffraction. Of these compounds, brujavanoid A (1) represents the first apotirucallane-type triterpenoid with a novel 19(10 → 9) abeo motif, and brujavanoids B and C (2–3) are the first apotirucallane-type triterpenoids with a rarely occurring 14-hydorxy-15,16-epoxy fragment. All the isolates were evaluated for their anti-inflammatory effect in an LPS-activated RAW264.7 cells model. Furthermore, the most active one, brujavanoid E (5), can suppress the transcriptional expression of typical pro-inflammatory mediators and inhibit the nuclear translocation of NF- κ B p65 in the LPS- activated RAW264.7 cells. [ABSTRACT FROM AUTHOR]

Eight previously undescribed triterpenoids, including four dammarane-type triterpenoids, named meliasenans A−D (1 – 4), four apotirucallane-type triterpenoids, named meliasenans E−H (5 – 8), along with nine known analogues (9 – 17) have been isolated from the stem bark of Melia toosendan. The structures of the new compounds were elucidated by IR, HRESIMS, 1D, 2D NMR, electronic circular dichroism (ECD) calculations, as well as single-crystal X-ray diffraction analysis. The results of bioassay showed that the new compounds 7 and 8 exhibited potential antibacterial effect on Pseudomonas solanacearum and Bacillus gasoformans, with MIC values of 117.2 μg mL−1 and 118 μg mL−1, respectively. Moreover, 8 and 11 showed apparent antibacterial activities against Bacillus subtilis (ATCC 6051) with MIC values of 118 μg mL−1 and 92.1 μg mL−1, respectively. Eight previously undescribed and nine known triterpenoids were isolated from the stem bark of Melia toosendan. [Display omitted] • Eight undescribed and nine known triterpenoids were isolated from Melia toosendan. • Their structures were elucidated by spectroscopic methods and X-ray diffraction. • Meliasenan G and Meliasenan H showed weak antibacterial activity. [ABSTRACT FROM AUTHOR]

A series of previously unreported compounds including seven new apotirucallane protolimonoids, xylogranatumines A-G (1-7), were isolated together with three known analogues (8-10) from the twigs and leaves of the Chinese mangrove, Xylocarpus granatum. The structures of these new compounds were elucidated by extensive spectroscopic analysis including 1D and 2D NMR and high-resolution electrospray ionization mass spectrometry (HRESIMS) and by comparison with those of related known compounds in the literature. Xylogranatumine F (6) exhibited cytotoxic activity against A549 tumor cell in vitro. [ABSTRACT FROM AUTHOR]

Bioassay-directed isolation of Feroniella lucida stem bark yielded three new apotirucallane triterpenoids named feroniellides C-E. The structures of the new compounds were established by extensive analysis of spectroscopic data. Of triterpenoids examined, feroniellides D and E revealed anticancer activity against KB and HeLa cells with IC50 values in range of 3.4–14.2 µg mL−1, which are significantly more potent than feroniellides A-C (IC50 25.5–60.0 µg mL−1). The present investigation suggests that an isovalerate moiety in feroniellides D and E is possibly associated with exerting cytotoxicity against cancer cells. [ABSTRACT FROM AUTHOR]

Abstract: Twenty-three new triterpenoids ( 1–23 ), all having an apotirucallane skeleton, were isolated from the seeds, leaves, and stems of Cedrela sinensis (Meliaceae). Their structures were determined by 2D NMR experiments, X-ray crystallographic analysis, and chemical methods. These triterpenoids showed a moderate cytotoxic activity against P-388 murine leukemia cells (IC50 0.26–9.9μg/mL). [Copyright &y& Elsevier]

Ten new triterpenoid compounds with structure diversity of the C-17 side-chain, including nine tirucallanes, named xylocarpols A–E (1–5) and agallochols A–D (6–9), and an apotirucallane, named 25-dehydroxy protoxylogranatin B (10), were isolated from the mangrove plants Xylocarpus granatum, Xylocarpus moluccensis, and Excoecaria agallocha. The structures of these compounds were established by HR-ESIMS and extensive one-dimensional (1D) and two-dimensional (2D) NMR investigations. The absolute configurations of 1 and 2 were unequivocally determined by single-crystal X-ray diffraction analyses, conducted with Cu Kα radiation; whereas those of 4, 6–8 were assigned by a modified Mosher's method and the comparison of experimental electronic circular dichroism (ECD) spectra. Most notably, 5, 6, 7, and 9 displayed potent activation effects on farnesoid–X–receptor (FXR) at the concentration of 10.0 μM; 10 exhibited very significant agonistic effects on pregnane–X–receptor (PXR) at the concentration of 10.0 nM. [ABSTRACT FROM AUTHOR]