16 results on '"Mimaki, Yoshihiro"'
Search Results
2. Two new homoisoflavonoids from the bulbs of Bessera elegans.
- Author
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Matsuo Y, Kurihara R, Akagi N, and Mimaki Y
- Subjects
- HL-60 Cells, Humans, Isoflavones chemistry, Isoflavones pharmacology, Antineoplastic Agents, Phytogenic isolation & purification, Isoflavones isolation & purification, Liliaceae chemistry
- Abstract
A further chemical investigation of the bulbs of Bessera elegans (Liliaceae) led to the isolation of a new homoisoflavonoid (1), a new scillascillin-type homoisoflavonoid (2), three known flavonoids (3-5), and two known norlignans (6 and 7). The structures of the new homoisoflavonoids (1 and 2) were determined based on the results of extensive spectroscopic analysis, including two-dimensional NMR data. The isolated compounds (1-7) were evaluated for cytotoxicity against HL-60 human promyelocytic leukemia cells and TIG-3 normal human diploid fibroblasts. Compound 1 exhibited potent tumor-selective cytotoxic activity against HL-60 cells.
- Published
- 2014
3. Steroidal glycosides from the bulbs of Bessera elegans and their cytotoxic activities.
- Author
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Matsuo Y, Akagi N, Hashimoto C, Tachikawa F, and Mimaki Y
- Subjects
- Antineoplastic Agents, Phytogenic chemistry, Apoptosis drug effects, Cell Cycle Checkpoints, Drug Screening Assays, Antitumor, Glycosides chemistry, HL-60 Cells, Humans, Japan, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Plant Roots chemistry, Steroids chemistry, Sterols, Antineoplastic Agents, Phytogenic isolation & purification, Antineoplastic Agents, Phytogenic pharmacology, Glycosides isolation & purification, Glycosides pharmacology, Liliaceae chemistry, Steroids isolation & purification, Steroids pharmacology
- Abstract
Examination of the bulbs of Bessera elegans (Liliaceae) led to isolation of nine new and five known steroidal glycosides. The structures of the nine compounds were determined based on the results of spectroscopic analysis, including two-dimensional NMR, and hydrolysis followed by chromatographic and spectroscopic analysis. The isolated compounds and derivatives were evaluated for cytotoxicity against HL-60 human promyelocytic leukemia cells, A549 human lung adenocarcinoma cells, and TIG-3 normal human diploid fibroblasts. One compound, the pseudo-furostanol glycoside, induced apoptosis in HL-60 and A549 cells in a time-dependent manner and cell-cycle arrest at the G0/G1 phase in A549 cells., (Copyright © 2013 Elsevier Ltd. All rights reserved.)
- Published
- 2013
- Full Text
- View/download PDF
4. New cholestane glycosides and sterols from the underground parts of Chamaelirium luteum and their cytotoxic activity.
- Author
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Yokosuka A, Takagi K, and Mimaki Y
- Subjects
- Antineoplastic Agents chemistry, Antineoplastic Agents isolation & purification, Cell Survival drug effects, Cholestanes chemistry, Cholestanes isolation & purification, Drug Screening Assays, Antitumor, Glycosides chemistry, Glycosides isolation & purification, HL-60 Cells, Humans, Hydrolysis, Inhibitory Concentration 50, Leukemia, Promyelocytic, Acute, Magnetic Resonance Spectroscopy, Molecular Structure, Phytosterols chemistry, Phytosterols isolation & purification, Phytotherapy, Plant Extracts chemistry, Plant Extracts isolation & purification, Plant Extracts pharmacology, Plant Roots chemistry, Plants, Medicinal, Antineoplastic Agents pharmacology, Cholestanes pharmacology, Glycosides pharmacology, Liliaceae chemistry, Phytosterols pharmacology
- Abstract
Six new cholestane glycosides (1, 5, 6, 10, 12, and 13) and two new sterols (9 and 11), along with five known compounds (2-4, 7, and 8), were isolated from the underground parts of Chamaelirium luteum (Liliaceae). The structures of these new compounds were determined by spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds and aglycones were evaluated for their cytotoxic activity against HL-60 human leukemia cells. Compounds 6a, 10a, 12a, 13, and 13a were cytotoxic to HL-60 cells, with IC50 values of 12.8, 9.8, 15.3, 6.2, and 10.2 µM, respectively.
- Published
- 2013
- Full Text
- View/download PDF
5. Chemical constituents of the bulbs of Habranthus brachyandrus and their cytotoxic activities.
- Author
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Jitsuno M, Yokosuka A, Sakagami H, and Mimaki Y
- Subjects
- Cell Line, Tumor, Drug Screening Assays, Antitumor, Flavanones chemistry, Flavanones isolation & purification, Flavanones toxicity, Glucosides chemistry, Glucosides isolation & purification, Glucosides toxicity, HL-60 Cells, Humans, Magnetic Resonance Spectroscopy, Molecular Conformation, Phenols chemistry, Phenols isolation & purification, Phenols toxicity, Plant Roots chemistry, Liliaceae chemistry
- Abstract
The bulbs of Habranthus brachyandrus (Amaryllidaceae) have been extensively analyzed for their chemical constituents, resulting in the isolation of eight flavan derivatives (1-8), four of which are new naturally occurring compounds; a new hydroxybutyric acid glucoside (9); three known phenolic compounds (10-12); and six known alkaloids (13-18). The structures of the new compounds were determined on the basis of spectroscopic analysis, including two-dimensional (2D) NMR data, and chemical evidence. The isolated compounds and a few derivatives were evaluated for their cytotoxic activities against HL-60 human promyelocytic leukemia cells and HSC-2 human oral squamous cell carcinoma cells.
- Published
- 2009
- Full Text
- View/download PDF
6. New steroidal glycosides from rhizomes of Clintonia udensis.
- Author
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Matsuo Y, Watanabe K, and Mimaki Y
- Subjects
- Cell Proliferation drug effects, Glycosides isolation & purification, Glycosides therapeutic use, HL-60 Cells, Humans, Molecular Structure, Steroids isolation & purification, Steroids therapeutic use, Antineoplastic Agents chemistry, Glycosides chemistry, Liliaceae chemistry, Rhizome chemistry, Steroids chemistry
- Abstract
A total of 10 steroidal glycosides, together with three new spirostanol glycosides (6-8), a new furostanol glycoside (9), and a new cholestane glycoside (10), were isolated from the rhizomes of Clintonia udensis (Liliaceae). The structures of the new compounds were determined on the basis of extensive spectroscopic analyses, including 2-D nuclear magnetic resonance (NMR) data, and of hydrolytic cleavage followed by chromatographic or spectroscopic analyses. The isolated glycosides were evaluated for their cytotoxic activity against HL-60 leukemia cells. Spirostanol glycosides 1 and 2, and furostanol glycoside 4 showed cytotoxic activity with IC(50) values of 3.2+/-0.02, 2.2+/-0.12, and 2.2+/-0.06 microg/ml, respectively. Neither the spirostanol and furostanol saponins with a hydroxy group at C-1 (6 and 9) and C-12 (7 and 8) nor cholestane glycosides (5 and 10) exhibited apparent cytotoxic activity at a sample concentration of 10 microg/ml.
- Published
- 2008
- Full Text
- View/download PDF
7. Steroidal glycosides from the rhizomes of Ruscus hypophyllum.
- Author
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Mimaki Y, Aoki T, Jitsuno M, Kiliç CS, and Coşkun M
- Subjects
- Glycosides isolation & purification, Magnetic Resonance Spectroscopy methods, Magnetic Resonance Spectroscopy standards, Molecular Structure, Reference Standards, Species Specificity, Steroids isolation & purification, Glycosides chemistry, Liliaceae chemistry, Rhizome chemistry, Steroids chemistry
- Abstract
Seven steroidal glycosides, along with one known glycoside, were isolated from the rhizomes of Ruscus hypophyllum (Liliaceae). Comprehensive spectroscopic analysis, including 2D NMR spectroscopy, and the results of acid hydrolysis allowed the chemical structures of the compounds to be assigned as (23S,25R)-23-hydroxyspirost-5-en-3beta-yl O-alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranoside (1), 1beta-hydroxyspirosta-5,25(27)-dien-3beta-yl O-alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranoside (2), (22S)-16beta,22-dihydroxycholest-5-en-3beta-yl O-alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranoside (3), (22S)-16beta-[(beta-d-glucopyranosyl)oxy]-22-hydroxycholest-5-en-3beta-yl O-alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranoside (4), (22S)-16beta-[(beta-d-glucopyranosyl)oxy]-22-hydroxycholest-5-en-3beta-yl beta-d-glucopyranoside (5), (22S)-16beta-[(beta-d-glucopyranosyl)oxy]-3beta,22-dihydroxycholest-5-en-1beta-yl O-alpha-l-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl-beta-d-xylopyranoside) (6), and (22S)-16beta-[(beta-d-glucopyranosyl)oxy]-3beta,22-dihydroxycholest-5-en-1beta-yl O-alpha-l-rhamnopyranosyl-(1-->2)-O-[beta-d-xylopyranosyl-(1-->3)]-beta-d-xylopyranoside (7), respectively. This is the first isolation of a series of cholestane glycosides from a Ruscus species.
- Published
- 2008
- Full Text
- View/download PDF
8. 27-norlanostane glycosides from the bulbs of Muscari paradoxum.
- Author
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Kuroda M, Mimaki Y, Ori K, Sakagami H, and Sashida Y
- Subjects
- Antineoplastic Agents, Phytogenic chemistry, Antineoplastic Agents, Phytogenic pharmacology, Drug Screening Assays, Antitumor, Glycosides chemistry, Glycosides pharmacology, Humans, Japan, Lanosterol chemistry, Lanosterol pharmacology, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Tumor Cells, Cultured, Antineoplastic Agents, Phytogenic isolation & purification, Glycosides isolation & purification, Lanosterol analogs & derivatives, Lanosterol isolation & purification, Liliaceae chemistry
- Abstract
Eight 27-norlanostane glycosides (1-8), including five new compounds (3 and 5-8), were isolated from the MeOH extract of the bulbs of Muscari paradoxum. The structures of the new compounds were determined on the basis of extensive spectroscopic analysis, including 2D NMR data, and the results of hydrolytic cleavage. The cytotoxic activity of 1-8 against HSC-2 human oral squamous cell carcinoma cells is also reported.
- Published
- 2004
- Full Text
- View/download PDF
9. Lanosterol and tetranorlanosterol glycosides from the bulbs of Muscari paradoxum.
- Author
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Ori K, Koroda M, Mimaki Y, Sakagami H, and Sashida Y
- Subjects
- Antineoplastic Agents, Phytogenic chemistry, Antineoplastic Agents, Phytogenic isolation & purification, Antineoplastic Agents, Phytogenic pharmacology, Carbohydrate Sequence, Cell Line, Tumor, Glycosides pharmacology, Humans, Hydrolysis, Inhibitory Concentration 50, Lanosterol pharmacology, Molecular Sequence Data, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Plant Extracts chemistry, Glycosides chemistry, Glycosides isolation & purification, Lanosterol chemistry, Lanosterol isolation & purification, Liliaceae chemistry, Plant Structures chemistry
- Abstract
Three tetranorlanostane glycosides, named lucilianosides C-E, and three lanostane glycosides, named scillasaponins E-G, together with a known lanostane glycoside, were isolated from the MeOH extract of Muscari paradoxum (Liliaceae) bulbs, as confirmed by detailed analysis of their 1H, 13C, and two-dimensional NMR spectroscopic data, and by the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activity against HSC-2 human oral squamous cell carcinoma cells.
- Published
- 2003
- Full Text
- View/download PDF
10. Bulbinelonesides A-E, phenylanthraquinone glycosides from the roots of Bulbinella floribunda.
- Author
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Kuroda M, Mimaki Y, Sakagami H, and Sashida Y
- Subjects
- Anthraquinones chemistry, Anthraquinones pharmacology, Antineoplastic Agents, Phytogenic chemistry, Antineoplastic Agents, Phytogenic pharmacology, Carcinoma, Squamous Cell, Cells, Cultured drug effects, Circular Dichroism, Drug Screening Assays, Antitumor, Glycosides chemistry, Glycosides pharmacology, Humans, Inhibitory Concentration 50, Japan, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Plant Roots chemistry, Stereoisomerism, Tumor Cells, Cultured drug effects, Anthraquinones isolation & purification, Antineoplastic Agents, Phytogenic isolation & purification, Glycosides isolation & purification, Liliaceae chemistry, Plants, Medicinal chemistry
- Abstract
The roots of Bulbinella floribunda have been analyzed for the phenolic constituents, resulting in the isolation of five new phenylanthraquinone glycosides, named bulbinelonesides A-E (1-5), along with two known phenylanthraquinones, (+)-M-knipholone (6) and (+)-M-isoknipholone (7). The structures of the new compounds were determined on the basis of extensive spectroscopic analysis, including 2D NMR, and the results of enzymatic hydrolysis. Although the new compounds 3-5, whose absolute stereochemistry of the unsymmetric biaryl moiety was determined to be P by the CD spectrum, did not show apparent cytotoxicity against cultured HSC-2 tumor cells and HPC normal cells, the new compounds 1 and 2, as well as the known compounds 6 and 7, whose biaryl bond was assigned as M, exhibited a tumor-specific cytotoxicity against HSC-2 cells comparable to or slightly weaker than etoposide, used as a positive control.
- Published
- 2003
- Full Text
- View/download PDF
11. Norlanostane and lanostane glycosides from the bulbs of Chionodoxa luciliae and their cytotoxic activity.
- Author
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Ori K, Kuroda M, Mimaki Y, Sakagami H, and Sashida Y
- Subjects
- Carbohydrate Sequence, Glycosides chemistry, Glycosides isolation & purification, Humans, Liliaceae chemistry, Molecular Sequence Data, Plant Extracts chemistry, Plant Extracts isolation & purification, Plant Extracts toxicity, Plant Structures chemistry, Tumor Cells, Cultured, Glycosides toxicity, Liliaceae toxicity, Plant Structures toxicity
- Abstract
Ten lanostane glycosides (1-10), including two new norlanostane glycosides (2 and 7) and a new lanostane glycoside with a spirolactone ring system (9), were isolated from the fresh bulbs of Chionodoxa luciliae (Liliaceae). The structures of the new compounds were determined on the basis of extensive spectroscopic analysis and the results of hydrolytic cleavage to be (23S)-3beta-[(O-beta-D-apiofuranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)-beta-D-glucopyranosyl)oxy]-17alpha,23-epoxy-28,29-dihydroxy-27-norlanost-8-en-24-one (2), (23S)-17alpha,23-epoxy-29-hydroxy-3beta-[(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)-beta-D-glucopyranosyl)oxy]-27-norlanost-8-ene-15,24-dione (7), and (23S,25R)-17alpha,23-epoxy-29-hydroxy-3beta-[(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)-beta-D-glucopyranosyl)oxy]lanost-8-en-23,26-olide (9), respectively. The cytotoxic activity of the isolated compounds against HSC-2 human oral squamous cell carcinoma cells are also reported.
- Published
- 2003
- Full Text
- View/download PDF
12. Steroidal glycosides from the bulbs of Lilium speciosum.
- Author
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Iguchi, Tomoki, Yokosuka, Akihito, Kuroda, Minpei, Takeya, Mayuko, Hagiya, Mizuki, and Mimaki, Yoshihiro
- Abstract
• Eight new spirostanol glycosides and a new cholestane glycoside were isolated from the bulbs of Lilium speciosum. • The isolated compounds and the aglycones were evaluated for their cytotoxic activity against HL-60 and A549 cells. • Compounds 12 , 20 , and 21 exhibited moderate cytotoxic activity. Steroidal glycosides (1 - 21), including eight new spirostanol glycosides (1 - 8) and a new cholestane glycoside (9), were isolated from the bulbs of Lilium speciosum. The structures of the new compounds were determined based on spectroscopic data analysis and hydrolytic cleavage reactions. The isolated compounds and their aglycones (1a , 8a , and 9a) were evaluated for their cytotoxicity against HL-60 human acute promyelocytic leukemia cells and A549 human lung carcinoma cells. Compounds 12 and 21 exhibited moderate cytotoxic activity toward HL-60 and A549 cells, with IC 50 values of 6.9 μM and 5.1 μM against HL-60 cells, and 7.6 μM and 4.4 μM against A549 cells, respectively. Compound 20 only showed moderate cytotoxicity toward A549 cells, with an IC 50 value of 6.7 μM. [ABSTRACT FROM AUTHOR]
- Published
- 2020
- Full Text
- View/download PDF
13. Steroidal glycosides from the underground parts of Trillium erectum and their cytotoxic activity
- Author
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Yokosuka, Akihito and Mimaki, Yoshihiro
- Subjects
- *
GLYCOSIDES , *STEROIDS , *TRILLIUMS , *SPECTRUM analysis , *ANTINEOPLASTIC agents , *LEUKEMIA treatment , *NUCLEAR magnetic resonance - Abstract
Abstract: Six steroidal glycosides, along with 14 known compounds, were isolated from the underground parts of Trillium erectum L. (Liliaceae). The structures of 1–6 were determined on the basis of extensive spectroscopic analysis, including two-dimensional (2D) NMR data, and a few chemical transformations. The isolated compounds were evaluated for their cytotoxic activity against HL-60 human promyelocytic leukemia cells. [Copyright &y& Elsevier]
- Published
- 2008
- Full Text
- View/download PDF
14. Ornithosaponins A–D, four new polyoxygenated steroidal glycosides from the bulbs of Ornithogalum thyrsoides
- Author
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Kuroda, Minpei, Ori, Kazutomo, and Mimaki, Yoshihiro
- Subjects
- *
GLYCOSIDES , *GLUCOSIDES , *HYDROLYSIS , *SUGAR - Abstract
Abstract: By analyzing the steroidal glycoside content of fresh bulbs of Ornithogalum thyrsoides (Liliaceae), we were able to isolate four new polyoxygenated steroidal glycosides, which we named ornithosaponins A–D (1–4). The structures of 1–4 were elucidated on the basis of extensive spectroscopic analysis, including that of 2D NMR data, and the results of acidic or alkaline hydrolysis. The aglycone structure of 1–4 has not been previously reported. It is also notable that ornithosaponins B–D (2–4) have been found to contain 6-deoxy-β-d-gulopyranose as a sugar component, which is rarely encountered in plant glycosides. [Copyright &y& Elsevier]
- Published
- 2006
- Full Text
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15. Karataviosides G–K, five new bisdesmosidic steroidal glycosides from the bulbs of Allium karataviense.
- Author
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Kuroda, Minpei, Ori, Kazutomo, Takayama, Hiroshi, Sakagami, Hiroshi, and Mimaki, Yoshihiro
- Subjects
- *
GLYCOSIDES , *ALLIUM , *STEROIDS , *NUCLEAR magnetic resonance spectroscopy , *HYDROLYSIS , *FUROSTANOL , *ASPARAGACEAE - Abstract
We have analyzed the steroidal glycosides in Allium karataviense bulbs, and isolated five new bisdesmosidic steroidal glycosides: karataviosides G−K ( 1 – 5 ). The structures were elucidated by extensive spectroscopic analysis, including 2D NMR and enzymatic and hydrolytic cleavage. Karatavioside G ( 1 ) is an entirely novel furostanol glycoside, which has an O -β- d -glucopyranosyl-(1 → 6)-β- d -glucopyranosyl-(1 → 6)-β- d -glucopyranosyl unit at C-26 of the aglycone. Although a variety of cholestanol glycosides have been isolated, mainly from Liliaceae and Agavaceae, karataviosides J and K ( 4 and 5 ) are also notable because they are the most polar cholestanol bisdesmosides discovered, in which a lycotetraose is attached to C-3 of the aglycone, and a glucose or O -glucosyl-(1 → 3)-glucose is attached at C-16. The isolated glycosides were also evaluated for their cytotoxic activities against cultured tumor cell lines. [ABSTRACT FROM AUTHOR]
- Published
- 2015
- Full Text
- View/download PDF
16. Steroidal glycosides from the bulbs of Fritillaria meleagris and their cytotoxic activities.
- Author
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Matsuo, Yukiko, Shinoda, Daisuke, Nakamaru, Aina, and Mimaki, Yoshihiro
- Subjects
- *
GLYCOSIDES , *STEROIDS , *FRITILLARIA meleagris , *ANTINEOPLASTIC agents , *APOPTOSIS , *FLOW cytometry , *CASPASES - Abstract
Highlights: [•] 10 New steroidal glycosides were isolated from the bulbs of Fritillaria meleagris. [•] Apoptosis in HL-60 and A549 were evaluated by caspase-3 and flow cytometry. [•] 5β-spirostanol (2) and a cholestane (17a) induced apoptosis through different mechanisms. [•] (22R)-spirosolanol (11) selectively induced apoptosis without affecting caspase-3. [Copyright &y& Elsevier]
- Published
- 2013
- Full Text
- View/download PDF
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