Three New Megastigmane Glycosides from Hylomecon vernalis

Lee, Seung Young; Choi, Sang Un; Lee, Kang Ro

doi:10.5012/bkcs.2011.32.10.3813

Cited by 13 publications

(9 citation statements)

References 13 publications

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“…longituba with anti-neurodegenerative effects remain large unknown. In this study, nine terpenoids (1)(2)(3)(4)(5)(6)(7)(8)(9) including five new compounds (1)(2)(3)(4)(5) were isolated and characterized from G. hederacea var. longituba (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

“…Structures of these compounds were established by 1D and 2D NMR and HR-ESIMS, comparison of experimental and calculated ECD data, and hydrolysis. Herein, the isolation and structural elucidation of the isolated compounds (1)(2)(3)(4)(5)(6)(7)(8)(9) and assessment for their anti-neuroinflammatory activity on NO production in lipopolysaccharide (LPS)-activated BV-2 cells, NGF secretion-stimulation activities in C6 glioma cells, and cytotoxic activities are described.…”

Section: Introductionmentioning

confidence: 99%

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Terpenoids from Glechoma hederacea var. longituba and Their Biological Activities

Kim¹,

Khan²,

Kim³

et al. 2022

Preprint

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Glechoma hederacea var. longituba (common name: ground-ivy) has been used for the treatment of asthma, bronchitis, cholelithiasis, colds, and inflammation. In the present study, three new sesquiterpene glycosides (1–3), two new diterpene glycosides (4–5), and four known compounds (6–9) were isolated from its MeOH extract. Structure elucidation was performed for the five new compounds (1–5) using 1D and 2D NMR, HRESIMS, ECD calculation, and chemical methods. All the isolates (1–9) were assessed for their anti-neuroinflammatory activity on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated BV-2 cells, nerve growth factor (NGF) secretion stimulation activity in C6 glioma cells, and cytotoxic activity against four human cancer cell lines (A549, SK-OV-3, SK-MEL-2, and HCT15). Compounds 2 and 5–7 exhibited inhibitory effects on NO production with IC50 values of 52.21, 47.90, 61.61, and 25.35 μM, respectively. Compound 5 also exhibited a significant stimulating effect on NGF secretion (122.77 ± 8.10%). Compound 9 showed potent cytotoxic activity against SK-OV-3 (IC50 3.76 μM) and SK-MEL-2 (IC50 1.48 μM) cell lines, while 7 displayed a strong cytotoxic activity against SK-MEL-2 (IC50 9.81 μM) cell line

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Terpenoids from Glechoma hederacea var. longituba and Their Biological Activities

Kim¹,

Khan²,

Kim³

et al. 2022

Preprint

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“…Its roots have been used as a traditional Chinese medicine for the treatment of rheumatism and injuries [ 1 ]. Although a variety of chemical constituents, including alkaloids, flavonoids, and megastigmoids, were previously isolated from H. japonica , and pharmacological studies on its anti-inflammatory properties, antibacterial activities, and antitumor action have been reported [ 2 , 3 , 4 , 5 , 6 , 7 ], the investigation of saponins in H. japonica has not been reported until now. As part of our study on the plants of Papaveraceae family, we have been carrying out an investigation of saponins in H. japonica .…”

Section: Introductionmentioning

confidence: 99%

New Triterpenoid Saponins from the Herb Hylomecon japonica

Gao

Wang

et al. 2017

Molecules

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Background: Hylomecon japonica, a plant of the Papaveraceae family which is well-known for the alkaloids they produce, is a perennial plant widely distributed in the northeast, central and east regions of China. Although a variety of chemical constituents, including alkaloids, flavonoids, and megastigmoids, have been isolated from H. japonica, the investigation of saponins in H. japonica has not been reported until now. Methods: Various separation techniques, including polyporous resin column chromatography, silica gel column chromatography and hemi-preparative HPLC were applied to the isolation of triterpenoid saponins, and chemical methods such as acid hydrolysis and spectroscopic methods including HRESIMS and NMR were applied to their structure elucidation, and the XTT reduction method was used to assay cytotoxicity. Results: Two new triterpenoid saponins, named hylomeconoside A (1) and B (2) which were identified as 3-O-β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyl-gypsogenin-28-O-β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-β-d-quinovopyranoside (1) and 3-O-β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyl-gypsogenin-28-O-β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside (2), and two known triterpenoid saponins identified as dubioside C (3) and lucyoside P (4) on the basis of spectroscopic and chemical evidence, were isolated from H. japonica. Compound 1 exhibited moderate cytotoxicity on MGC-803 and HL-60 cells, with IC50 values of 43.8 and 32.4 μg·mL−1, respectively. Conclusions: Compounds 1 and 2 are new saponins, and 1 is considered to be one of the antitumor principles in this plant. This is the first time that triterpenoid saponins have been isolated from plants of the Papaveraceae family.

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“…The 1 H-and 13 C-NMR (including DEPT) and 2D-NMR ( 1 H, 1 H-COSY, HMQC, HMBC, and ROESY) spectra of 1 revealed the presence of a xylose unit [13] (1'')), 74.5 (C(4'')), 72.2 (C(2'')), 72.0 (C(3'')), 69.9 (C(5'')), and 18.8 (C(6''))). The coupling constant (J ¼ 7.5) of the xylose anomeric H-atom suggested a b-form [13]. The configuration of rhamnose was determined to be a by comparing the 13 C-NMR data of C(3'') (d(C) 72.0) and C(5'') (d(C) 69.9) (a-form: d(C) 72.5, 69.0; b-form: d(C) 73.8, 73.1 [14]).…”

mentioning

confidence: 99%

“…(18) (14)), 42.0 (C(9)), 35.6 (C(8)), 31.8 (C(5)), and 27.6 (C(25)); nine CH 2 groups at d(C) 40.3 (C(12)), 34.2 (C(15)), 32.2 (C(11)), 27.3 (C(2)), 26.4 (C(4)), 26.3 (C(24)), 26.2 (C(7) and C(23)), and 21.5 (C(6)), and three quaternary C-atoms at d(C) 109.6 (C (22)), 40.6 (C(13)), and 39.3 (C(10)), suggesting that 1 was a spirostane-type steroid derivative [12]. The 1 H-and 13 C-NMR (including DEPT) and 2D-NMR ( 1 H, 1 H-COSY, HMQC, HMBC, and ROESY) spectra of 1 revealed the presence of a xylose unit [13] (1'')), 74.5 (C(4'')), 72.2 (C(2'')), 72.0 (C(3'')), 69.9 (C(5'')), and 18.8 (C(6''))). The coupling constant (J ¼ 7.5) of the xylose anomeric H-atom suggested a b-form [13].…”

mentioning

confidence: 99%

Two New Cytotoxic Spirostane‐Steroidal Saponins from the Roots of Bletilla striata

Park

Woo

Choi

et al. 2014

Helvetica Chimica Acta

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Two new spirostane-steroidal saponins, bletilnoside A (1) and bletilnoside B (2), together with five known compounds, 3 -7, were isolated from the roots of Bletilla striata (Thunb.) Reichb. F. The structures of the new compounds were determined based on their 1D-and 2D-NMR spectral data. The isolated compounds 1 -7 were tested for cytotoxicity against four human tumor cells (A549, SK-OV-3, SK-MEL-2, and HCT15) in vitro using a sulforhodamin B bioassay, and compounds 1, 2, and 5 showed significant cytotoxicities against all tested tumor cell lines with IC 50 values ranging from 3.98 AE 0.16 to 12.10 AE 0.40 mm.

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Three New Megastigmane Glycosides from Hylomecon vernalis

Cited by 13 publications

References 13 publications

Terpenoids from Glechoma hederacea var. longituba and Their Biological Activities

Terpenoids from Glechoma hederacea var. longituba and Their Biological Activities

New Triterpenoid Saponins from the Herb Hylomecon japonica

Two New Cytotoxic Spirostane‐Steroidal Saponins from the Roots of Bletilla striata

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