Novel Steroidal Glycosides from the Whole Plants of &lt;i&gt;Helleborus foetidus&lt;/i&gt;

Iguchi, Tomoki; Uchida, Yuka; Takano, Shingo; Yokosuka, Akihito; Mimaki, Yoshihiro

doi:10.1248/cpb.c19-01037

Cited by 7 publications

(3 citation statements)

References 23 publications

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“…[13,14] Acid hydrolysis of 1 obtained D-glucose and D-apiose, which were identified by by TLC comparison with authentic samples and from the positive sign of the optical rotations. [15,16] The CD spectrum of 1 exhibited a negative Cotton effect at 214 nm, suggesting (2R)-configuration (figure 3). [17] Moreover, protons H-2, H-3, and H-4 appeared as all singlets suggesting that H-2/H-3 and H-3/H-4 are cisconfiguration.…”

Section: Resultsmentioning

confidence: 99%

A previously undescribed phenolic compound from Acanthus ilicifolius L.

Mai,

Huyen,

Hanh

et al. 2023

Vietnam Journal of Chemistry

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The plants Acanthus ilicifolius L. (Acanthaceae) are used in Vietnamese folk medicine for the treatment of stomach pain, hepatitis, asthama, and rheumatism. Phytochemical study on the methanol extract of the aerial parts of this plant led to the isolation of seven phenolic compounds, (2R,3R,4R)‐3,4‐dihydroxy‐7‐methoxyflavan 5‐O‐[β‐D‐apiofuranosyl‐(1→6)]‐β‐D‐glucopyranoside (1), quercitrin (2), isoquercitrin (3), kaempferol 3‐O‐α‐L‐arabinopyranoside (4), kaempferol 3‐O‐α‐L‐rhamnopyranoside (5), kaempferol 3‐O‐β‐D‐glucopyranoside (6), and 6‐O‐vanilloylarbutin (7). Among these isolates, compound 1 was previously undescribed compounds. Their chemical structures and the absolute configurations of the new compound were elucidated by 1D‐, 2D NMR, HR‐ESI‐MS and ECD spectroscopic techniques. The known compounds were identified by comparison their NMR spectral data with those reported in the literature.

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Section: Resultsmentioning

confidence: 99%

A previously undescribed phenolic compound from Acanthus ilicifolius L.

Mai,

Huyen,

Hanh

et al. 2023

Vietnam Journal of Chemistry

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“…Approximately 25% of all new anticancer agents approved by the Food and Drug Administration (FDA) between January 01, 1981, and September 30, 2019, were developed from natural products and natural product derivatives . In our continuous quest for the search for new candidates for anticancer agents from higher plants, we have discovered various cytotoxic steroidal glycosides from Cestrum nocturnum, Ornithogalum thyrsoides, Allium karataviense, Yucca glauca, Dracaena thalioides, Ornithogalum saundersiae, Convallaria majalis, Helleborus foetidus, Withania somnifera, Thevetia neriifolia, Avena sativa, and Digitalis purpurea . Currently, we have focused on the constituents of Agapanthus africanus (L.) Hoffmanns.…”

Section: Introductionmentioning

confidence: 99%

Structure Elucidation of 16 Undescribed Steroidal Glycosides from the Underground Parts of Agapanthus africanus and Apoptosis-Inducing Activity in Small-Cell Lung Cancer Cell

et al. 2023

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To explore new candidates for anticancer agents from natural products, the underground parts of Agapanthus africanus, commonly used as an ornamental plant, were investigated phytochemically. As a result, 16 undescribed steroidal glycosides (1–16) were obtained, and their structures were determined mainly by NMR spectroscopic analysis and chemical transformations. The cytotoxic activities of the isolated compounds (1–16) against SBC-3 human small-cell lung cancer cells, A549 human adenocarcinoma cells, and HL-60 human promyelocytic leukemia cells were evaluated using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2-tetrazolium bromide (MTT) assay. Compound 1, a bisdesmosidic furostanol glycoside, and 10, a bisdesmosidic spirostanol glycoside, were cytotoxic to all three cell lines with IC50 values ranging from 1.2 to 13 μM. As 1 exhibited the most potent cytotoxicity against SBC-3 cells among the isolated compounds, its apoptosis-inducing activity toward SBC-3 cells was examined. Compound 1 arrested SBC-3 cells at the G2/M phase of the cell cycle and effectively induced apoptosis via an intrinsic pathway accompanied by the dissipation of membrane potential and morphological changes in mitochondria.

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“…sativa have been reported to exhibit biological activities including the antimicrobial activity, antiparasitic activity, and cell growth inhibitory activity against HCT-116 and HT-29 human colon cancer cells . In our phytochemical investigations on higher plants, we have isolated numerous cytotoxic steroidal glycosides with a diverse range of structures, including pregnane glycosides, cardenolide glycosides, and bufadienolide glycosides. − This paper reports the structure determination of glycosides 1 – 6 and the cytotoxic activity of the isolated compounds ( 1 – 12 ) against HL-60 human promyelocytic leukemia cells, MIA PaCa-2 human pancreatic carcinoma cells, A549 human lung adenocarcinoma cells, and TIG-3 human lung normal diploid cells. Furthermore, the apoptosis-inducing activity of furospirostan glycoside 1 in HL-60 cells is investigated.…”

Section: Introductionmentioning

confidence: 99%

Steroidal Glycosides from the Aerial Parts of Avena sativa L. and Their Cytotoxic Activity

Yokosuka

Ishihara

Yamada

et al. 2021

J. Agric. Food Chem.

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Twelve steroidal glycosides (1–12) were isolated from the aerial parts of Avena sativa L. (Poaceae). Among the isolated compounds, 1 was directly isolated from the plant for the first time, and 2–6 were new steroidal glycosides. The structures of 1–6 were determined by analysis of their spectroscopic data, chemical transformations, and chromatographic and spectroscopic analyses of the hydrolyzed products. Compounds 5 and 6 were novel steroidal glycosides with a B-ring contracted skeleton (B-nor steroid). Compounds 1, 9, 11, and 12 were cytotoxic to HL-60 human promyelocytic leukemia cells, MIA PaCa-2 human pancreatic carcinoma cells, and A549 human lung adenocarcinoma cells with IC50 values ranging from 0.79 to 13.5 μM. HL-60 cells treated with 1 exhibited apoptotic characteristics, namely, condensed nuclear chromatin, accumulation of sub-G1 cells, and activation of caspase-3. Additionally, the loss of the mitochondrial membrane potential and the release of cytochrome c into the cytoplasm in 1-treated HL-60 cells suggested that 1 induced apoptosis through a mitochondrial-dependent apoptotic pathway.

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Novel Steroidal Glycosides from the Whole Plants of <i>Helleborus foetidus</i>

Cited by 7 publications

References 23 publications

A previously undescribed phenolic compound from Acanthus ilicifolius L.

A previously undescribed phenolic compound from Acanthus ilicifolius L.

Structure Elucidation of 16 Undescribed Steroidal Glycosides from the Underground Parts of Agapanthus africanus and Apoptosis-Inducing Activity in Small-Cell Lung Cancer Cell

Steroidal Glycosides from the Aerial Parts of Avena sativa L. and Their Cytotoxic Activity

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