A New Stereoisomeric Acetogenic Glycoside from the Flower Buds of Buddleja officinalis

Lee, Chul; Hwang, Kwang-Woo; Park, Soyoung

doi:10.5012/bkcs.2014.35.7.2159

Cited by 8 publications

(3 citation statements)

References 16 publications

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“…Compound 12 (peak 12 in Figure 2 B): ESI-MS ( m / z ): 245 [M + Na] + , 223 [M + H] + ; molecular formula C 13 H 18 O 3 , M = 222; 1 H-NMR (CD 3 OD- d 6 , 600 MHz) δ: 2.32 (3H, s, 10-CH 3 ), 1.08 (3H, s, 11-CH 3 ), 1.04 (3H, s, 12-CH 3 ), 1.92 (3H, d, J = 1.2 Hz, 13-CH 3 ), 2.29 (1H, d, J = 16.8 Hz, 2b-H), 2.62 (1H, d, J = 17.4 Hz, 2a-H), 5.95 (1H, m, 4-H), 6.45 (1H, d, J = 16.2 Hz, 8-H), 7.01 (1H, d, J = 15.6 Hz, 7-H); 13 C-NMR (CD 3 OD- d 6 , 150 MHz) δ: 41.2 (C-1), 49.1 (C-2), 198.9 (C-3), 126.6 (C-4), 163.3 (C-5), 78.6 (C-6), 146.9 (C-7), 130.3 (C-8), 199.3 (C-9), 26.3 (C-10), 22.1 (C-11), 23.4 (C-12), 17.8 (C-13). Comparing the above data with the literature [ 33 ], compound 12 was identified as (+)-dehydrovomifoliol.…”

Section: Methodssupporting

confidence: 55%

Chemical Constituents of the Ethyl Acetate Extract from Diaphragma juglandis Fructus and Their Inhibitory Activity on Nitric Oxide Production In Vitro

Wang

Dong

et al. 2017

Molecules

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Diaphragma juglandis fructus contains various bioactive constituents. Fourteen compounds were isolated from Diaphragma juglandis fructus by preparative high performance liquid chromatography (pre-HPLC) and high-speed counter-current chromatography (HSCCC). Their structures were identified by nuclear magnetic resonance (NMR) and electrospray ionization mass spectrometry (ESI-MS). Compounds (+)-dehydrovomifoliol (12), (6R,9R)-9-hydroxymegastigman-4-en-3-one (13) and (6R,9S)-9-hydroxymegastigman-4-en-3-one (14) are found from Juglans regia L. for the first time. Compounds dihydrophaseic acid (2), blumenol B (3) and (4S)-4-hydroxy-1-tetralone (11) are isolated from Diaphragma juglandis fructus for the first time. The anti-inflammatory effects of isolated compounds were evaluated by an in vitro model of lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. Compounds gallic acid (1), ethyl gallate (9) and (+)-dehydrovomifoliol (12) exhibited inhibitory activity on the nitric oxide production of RAW 264.7 at a concentration of 25 μM. The result indicated that the combination HSCCC with pre-HPLC is an effective way for compound separation and purification. And Diaphragma juglandis fructus constituents have the potential for the treatment of inflammatory-related diseases.

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Section: Methodssupporting

confidence: 55%

Chemical Constituents of the Ethyl Acetate Extract from Diaphragma juglandis Fructus and Their Inhibitory Activity on Nitric Oxide Production In Vitro

Wang

Dong

et al. 2017

Molecules

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“…In addition, it has also been used as a natural food dye to color yellow rice in southwestern China [6]. More recently, studies have shown that Buddlejae Flos contains flavonoids, phenylethanoid glycosides, terpenoids, saponins, alkaloids, and iridoids, which have various biological activities, including antioxidant, anti‐inflammatory, antibacterial, anti‐atherosclerosis, and neuroprotective effects [5,7‐11]. Our previous research indicated that acteoside (AC) and linarin (LIN) are the major bioactive ingredients of Buddlejae Flos, which have high contents and excellent properties [9] (Fig.…”

Section: Introductionmentioning

confidence: 99%

Separation of acteoside and linarin from Buddlejae Flos by high‐speed countercurrent chromatography and their anti‐inflammatory activities

GuangHui

Yang

Wei

et al. 2020

J of Separation Science

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Buddleja officinalis Maxim., a deciduous, flowering shrub, is used as a traditional Chinese medicine; the bioactivity of B. officinalis is primarily due to flavonoids and phenylethanoid glycosides. In the study, acteoside and linarin were successfully isolated from B. officinalis by high-speed countercurrent chromatography with a twophase solvent system composed of ethyl acetate: n-butanol: water (5:0.8:5, v/v/v). The purities of acteoside and linarin were determined to be 97.3 and 98.2%, respectively, using one-step high-speed countercurrent chromatography separation. The chemical structures of the two compounds were identified by electrospray ionization-mass spectrometry and nuclear magnetic resonance. After separation, the anti-inflammatory effects of the two compounds were evaluated using lipopolysaccharide-induced human umbilical vein endothelial cells. Acteoside and linarin inhibited the expression of nitric oxide, tumor necrosis factor α and interleukin 1β, which demonstrated that acteoside and linarin possessed anti-inflammatory activity. K E Y W O R D Sacteoside, anti-inflammatory, high-speed countercurrent chromatography, linarin, traditional Chinese medicine 1450

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“…The flower buds and inflorescences of this medicinal plant are commonly used for the treatment of eye diseases, including conjunctival congestion and soreness, photophobia, delacrimation, and cloudy and blurred vision, as well as hepatic asthenia [ 1 ]. Recent research has shown that the main components of B. officinalis are flavonoids, phenethyl alcohol glycosides, and saponins [ 2 , 3 , 4 , 5 ], although alkaloids and carotenoids are also present in the plant. Linarin is the major flavone and an important bioactive constituent of this plant, and it was used as the index component of B. officinalis in the 2015 edition of the Chinese Pharmacopeia.…”

Section: Introductionmentioning

confidence: 99%

Optimization of the Extraction Conditions for Buddleja officinalis Maxim. Using Response Surface Methodology and Exploration of the Optimum Harvest Time

GuangHui

Han

et al. 2017

Molecules

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The Box-Behnken design was used to evaluate the effects of the methanol concentration (60–100%), liquid to solid ratio (20:1 to 40:1 mL/g) and extraction time (20–40 min) on the yield of 11 constituents from Buddleja officinalis Maxim using ultrasound-assisted extraction. The Derringer’s desirability function approach showed that the modified optimum extraction conditions were: 76% methanol concentration, 33 min extraction time and a 34:1 mL/g solvent to solid ratio. Under these conditions, the experimentally measured yields of the compounds were in good agreement with the predicted values. An accurate and sensitive method was also established using high-performance liquid chromatography with diode-array detection for the simultaneous determination of the 11 compounds in Buddleja officinalis. The newly developed method was used to determine the amounts of bioactive components in Buddleja officinalis during four different growth stages. According to these results, we recommend that the full blossom stage is the best time for harvesting this plant to obtain the highest yield of crude materials.

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A New Stereoisomeric Acetogenic Glycoside from the Flower Buds of Buddleja officinalis

Cited by 8 publications

References 16 publications

Chemical Constituents of the Ethyl Acetate Extract from Diaphragma juglandis Fructus and Their Inhibitory Activity on Nitric Oxide Production In Vitro

Chemical Constituents of the Ethyl Acetate Extract from Diaphragma juglandis Fructus and Their Inhibitory Activity on Nitric Oxide Production In Vitro

Separation of acteoside and linarin from Buddlejae Flos by high‐speed countercurrent chromatography and their anti‐inflammatory activities

Optimization of the Extraction Conditions for Buddleja officinalis Maxim. Using Response Surface Methodology and Exploration of the Optimum Harvest Time

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