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Six new tirucallane-type triterpenoids, named munropenes A–F (1–6), were extracted from the whole plants of Munronia pinnata using a water extraction method. Their chemical structures were determined based on detailed spectroscopic data. The relative configurations of the acyclic structures at C-17 of munropenes A–F (1–6) were established using carbon–proton spin-coupling constants (2,3JC,H) and inter-proton spin-coupling constants (3JH,H). Furthermore, the absolute configurations of munropenes A–F (1–6) were determined through high-performance liquid chromatography (HPLC), single-crystal X-ray diffraction, and electronic circular dichroism (ECD) analyses. The antiproliferative effects of munropenes A–F were evaluated in five tumor cell lines: HCT116, A549, HepG2, MCF7, and MDAMB. Munropenes A, B, D, and F (1, 2, 4, and 6) inhibited proliferation in the HCT116 cell line with IC50 values of 40.90, 19.13, 17.66, and 32.62 µM, respectively. [ABSTRACT FROM AUTHOR]

The Euphorbiaceae plant Euphorbia neriifolia L. is distributed widely in India, Thailand, Southeastern China, and Taiwan and used as a carminative and expectorant to treat several inflammation-related diseases, such as gonorrhoea, asthma, and cancer. In the course of our search for potential anti-inflammatory agents from the titled plant, 11 triterpenes from the stem of E. neriifolia were isolated and reported in our previous endeavor. Given its rich abundance in triterpenoids, the ethanolic extract in this follow-up exploration has led to the isolation of additional eight triterpenes, including six new euphanes—neritriterpenols H and J–N (1 and 3–7)—one new tirucallane, neritriterpenol I (2), and a known compound, 11-oxo-kansenonol (8). Their chemical structures were elucidated on the basis of spectroscopic data, including 1D- and 2D NMR, and HRESIMS spectra. The absolute stereochemistry of neritriterpenols was determined by single-crystal X-ray diffraction analysis, ICD spectra, and DP4+ NMR data calculations. Compounds 1–8 were also evaluated for their anti-inflammatory activity by using lipopolysaccharide (LPS)-stimulated IL-6 and TNF-α on RAW 264.7 macrophage cells. Intriguingly, the euphane-type triterpenes (1 and 3–8) showed an inhibitory effect on LPS-induced IL-6 but not on TNF-α, while tirucallane-type triterpene 2 showed strong inhibition on both IL-6 and TNF-α.

Six new tirucallane-type triterpenoids, named munropenes A–F (1–6), were extracted from the whole plants of Munronia pinnata using a water extraction method. Their chemical structures were determined based on detailed spectroscopic data. The relative configurations of the acyclic structures at C-17 of munropenes A–F (1–6) were established using carbon–proton spin-coupling constants (2,3JC,H) and inter-proton spin-coupling constants (3JH,H). Furthermore, the absolute configurations of munropenes A–F (1–6) were determined through high-performance liquid chromatography (HPLC), single-crystal X-ray diffraction, and electronic circular dichroism (ECD) analyses. The antiproliferative effects of munropenes A–F were evaluated in five tumor cell lines: HCT116, A549, HepG2, MCF7, and MDAMB. Munropenes A, B, D, and F (1, 2, 4, and 6) inhibited proliferation in the HCT116 cell line with IC50 values of 40.90, 19.13, 17.66, and 32.62 µM, respectively.

The phytochemical investigation of Euphorbia tirucalli L. (Euphorbiaceae) yielded four new compounds, including a rare cadalene-type sesquiterpene (tirucadalenone), two tirucallane triterpenoids, euphorol L and euphorol M, with the latter being described as an epimeric mixture, and a euphane triterpene, namely, euphorol N, together with 7 known compounds. Their structures and absolute configurations were elucidated from analysis of 1D (1H, J-modulated 13C) and 2D NMR (HSQC, HMBC and NOESY), high-resolution mass spectrometry (HRESIMS), optical rotation, and GIAO NMR shift calculation followed by CP3 analysis, along with comparison with literature reports. All these compounds were tested for cytotoxicity against K562, MCF-7 and/or and HepG2 tumor cell lines. Only tirucadalenone displayed a mild cytotoxic activity. Four previously undescribed terpenoids: a cadalene (1), two tirucallanes (2 and 3a / 3b), and a euphane (4) were isolated from Euphorbia tirucalli L. Unlabelled Image [ABSTRACT FROM AUTHOR]

Chemical investigation of the roots of Entandrophragma congoënse (Meliaceae) led to the isolation of two new 3,4- seco -tirucallane triterpenes, namely seco -tiaminic acids B and C ( 1 and 2 ) together with nine known compounds: 3,4-secotirucalla-21-formyl-23-oxo-4(28),7,24-trien-3-oic acid ( 3 ), methyl angolensate ( 4 ), molucensin N ( 5 ), molucensin O ( 6 ), piscidinol A ( 7 ), 7 α ,20( S )-dihydroxy-4,24(28)-ergostadien-3-one ( 8 ), 24-methylene-cholest-5-en-3 β ,7 α -diol ( 9 ), entilin A ( 10 ), and entilin B ( 11 ). Their structures were determined using extensive spectroscopic methods including 1D and 2D NMR, HRMS, and CD analyses; new results were compared to existing data in the literature. The two newly identified seco -tiaminic acids showed moderate antiplasmodial and cytotoxic activities against a chloroquine-sensitive strain of the malaria parasite ( Plasmodium falciparum NF54) and were cytotoxic toward an L6 rat skeletal myoblast cell line, respectively. [ABSTRACT FROM AUTHOR]

Chemical characterization of the dichloromethane extract of Euphorbia retusa aerial parts by chromatographic methods afforded an inseparable mixture of two new tirucallane-type triterpenoids namely (3β, 24 S)- and (3β, 24 R)-tirucalla-7,25-diene-3,24-diol (1a and 1b) respectively, together with nine known compounds including six triterpenoids and three phenylpropanoids. Their structures were established on the basis of spectroscopic analyses, including 1D- and 2D- homo- and heteronuclear NMR experiments and mass spectrometry, as well as comparison with data from related compounds. The chemotaxonomic aspects were also discussed. [Display omitted] • Two new tirucallane-type triterpenoids together with nine known compounds were isolated from Euphorbia retusa. • Their structures were characterized by spectroscopic analysis. • The chemotaxonomic aspects were discussed. [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.

The Euphorbiaceae plant Euphorbia neriifolia L. is distributed widely in India, Thailand, Southeastern China, and Taiwan and used as a carminative and expectorant to treat several inflammation-related diseases, such as gonorrhoea, asthma, and cancer. In the course of our search for potential anti-inflammatory agents from the titled plant, 11 triterpenes from the stem of E. neriifolia were isolated and reported in our previous endeavor. Given its rich abundance in triterpenoids, the ethanolic extract in this follow-up exploration has led to the isolation of additional eight triterpenes, including six new euphanes-neritriterpenols H and J-N ( 1 and 3 - 7 )-one new tirucallane, neritriterpenol I ( 2 ), and a known compound, 11-oxo-kansenonol ( 8 ). Their chemical structures were elucidated on the basis of spectroscopic data, including 1D- and 2D NMR, and HRESIMS spectra. The absolute stereochemistry of neritriterpenols was determined by single-crystal X-ray diffraction analysis, ICD spectra, and DP4+ NMR data calculations. Compounds 1 - 8 were also evaluated for their anti-inflammatory activity by using lipopolysaccharide (LPS)-stimulated IL-6 and TNF-α on RAW 264.7 macrophage cells. Intriguingly, the euphane-type triterpenes ( 1 and 3 - 8 ) showed an inhibitory effect on LPS-induced IL-6 but not on TNF-α, while tirucallane-type triterpene 2 showed strong inhibition on both IL-6 and TNF-α., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2023 Chang, Huang, Wei, Lo, Lin, Chao, Liao, Shen, Chen, Li, Lin, Tai, Kuo and Liaw.)

A new tirucallane, 3β-hydroxy-3-decarbonyl-24-epi-piscidinol A (1), and two new pairs of tetranortriterpene 23-epimers, named thaimoluccepimers A (2) and B (3), were isolated from the seeds of a Thai mangrove,Xylocarpus moluccensis. The structures of these compounds were elucidated by HRESIMS and NMR spectroscopic analysis. [ABSTRACT FROM AUTHOR]

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]

Euphorbia neriifolia L. is widely distributed in India, Thailand, and China and has been used to treat diseases such as rotten sores and asthma as well as for its antidiabetic and anticancer effects. In this study, seven undescribed triterpenes, including six euphanes, neritriterpenols A-B and D-G, and a tirucallane, neritriterpenol C, together with four known triterpenes, were isolated from ethanolic extracts of E. neriifolia stems. Their structures with absolute configurations were determined through detailed spectroscopic data, including 1D and 2D NMR data analyses, single-crystal X-ray diffraction analysis, ECD spectra, and DP4+ NMR data calculations as well as Mo 2 (OAc) 4 -induced ECD analysis. Furthermore, preliminarily evaluation of the anti-inflammatory and anti-proliferative effects of the isolated triterpenes leads to the structure-activity relationship (SAR) studies implying that the unsaturated functional group at the end of the C17 side chain on euphane-type triterpenes may be correlated with the increase of anti-inflammatory and anti-proliferative activities. [Display omitted] • Seven undescribed triterpenes were isolated from ethanolic extracts of Euphorbia neriifolia stems. • Structures were determined by extensive spectroscopic analyses including NMR spectra, X-ray diffraction analysis, ECD spectra, DP4+ NMR data calculations, and Mo 2 (OAc) 4 -induced ECD analysis. • The anti-inflammatory and antiproliferative activities of the isolates were evaluated. [ABSTRACT FROM AUTHOR]

Two new tirucallane-type triterpenoids, (24 Z)-tirucalla-7,24-diene-3 β,11 β,26-triol ( 1) and (3 S,24 R)-tirucall-7-ene-3,24,25-triol ( 2), along with the known compound celastrol ( 3), were isolated from the root barks of Celastrus stylosus Wall. The structures of 1- 3 were established by spectroscopic methods, including extensive 2D NMR and MS analyses. It is the first report on tirucallane-type triterpenoids from the genus Celastrus and may be of vital chemotaxonomic significance. [ABSTRACT FROM AUTHOR]

Various chromatographic separations of the methanolic extract of Paramignya scandens stem and leaves resulted in the isolation of two new tirucallane derivatives, paramignyols A and B (1 and 2). Their structures were established by HR-ESI-MS, 1D and 2D NMR experiments, as well as, comparison with literature data. Compounds 1 and 2 showed significant cytotoxic activity (IC50s ~ 3.55-10.50 µM) on four tested human cancer cell lines: KB (epidermoid carcinoma), SK-Mel-2 (melanoma), LU-1 (lung adenocarcinoma), and MCF7 (breast cancer). This is the first report on chemical constituents and biological activities of P. scandens. [ABSTRACT FROM AUTHOR]

Two new tirucallane-type triterpenoids, 3 α,24 β,25-trihydroxy-21,21-dimethoxy-23-oxo-tirucall-7-ene ( 1) and 3 α-acetoxy-21 β-methoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone ( 2), were isolated from the stem barks of Aphanamixis grandifolia, and their structures were elucidated on the basis of spectroscopic data analysis including 1D, 2D NMR, IR, and ESI-MS spectral methods. The two isolates were evaluated for their cytotoxicities using NCI-H460 and HeLa cell lines. [ABSTRACT FROM AUTHOR]

Abstract: Five tirucallane type C26 triterpenoids, accompanied by two known compounds, 3α-hydroxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone and 3-oxo-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone, were isolated from the stem barks of Aphanamixis grandifolia. Their structures were established mainly by means of a combination of 1D and 2D NMR spectroscopic and mass spectrometry techniques as 3α-hydroxyl-21α-methoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone, 3α-hydroxy-21β-methoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone, 3-oxo-21α-methoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone, 3-oxo-21β-methoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone, and 3-oxo-21α-ethoxy-24,25,26,27-tetranortirucall-7-ene-23(21)-lactone. All isolates were in vitro evaluated for their cytotoxic activities against five tumor cell lines (MCF-7, HeLa, HepG2, SGC-7901 and BGC-823). [ABSTRACT FROM AUTHOR]

Bioassay-guided chromatographic purification of the antitubercular chloroform extract of Pandanus tectorius Soland. var. laevis leaves afforded a new tirucallane-type triterpene, 24,24-dimethyl-5β-tirucall-9(11),25-dien-3-one ( 1), squalene and a mixture of the phytosterols stigmasterol and β-sitosterol. Microplate Alamar Blue Assay (MABA) showed that 1 inhibited the growth of Mycobacterium tuberculosis H37Rv with a MIC of 64 μg/mL, while squalene and the sterol mixture have MICs of 100 and 128 μg/mL, respectively. [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. [ABSTRACT FROM AUTHOR]

A novel series of elemonic acid derivatives were synthesized and evaluated for their inhibitory activity on Pin1. Five compounds displayed significantly improved ability to inhibit Pin1 activity at micromolar levels. Compound 10 with 2-carboxylmethylene was the most active one with an IC50 value of 0.57 μM. The docking models of Pin1 support that introduction of an acidic group to elemonic acid enhance the Pin1 inhibitory activity., (Copyright © 2014. Published by Elsevier Ltd.)