Bioactive diarylheptanoids and stilbenes from the rhizomes of Dioscorea septemloba Thunb

Zhang, Yi; Ruan, Jing; Li, Jian; Chao, Li-Ping; Shi, Wenzhong; Yu, Haiyang; Gao, Xiumei; Wang, Tao

doi:10.1016/j.fitote.2017.01.004

Cited by 13 publications

(4 citation statements)

References 9 publications

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“…Then, the active parts were quickly locked by MRCC separation and activity screening, which was further separated under HSCCC of optimized conditions. Seven steroidal saponins, dioscoresides C (2), methyl protodioscin (4), pseudoprotodioscin ( 5), protogracillin (6), protodioscin (10), gracillin (11), dioscin (12), four diphenylethyl compounds, annulatomarin…”

Section: Discussionmentioning

confidence: 99%

“…This herb medicine is mainly planted in Zhejiang, Fujian, and Jiangxi Provinces, China, which has been famous for its application of the treatments of gonorrhea white turbid, excessive leucorrhea, damp heat sore poison, waist and knee arthralgia, and so on [2][3][4][5][6]. Chemical studies of D. spongiosa have indicated the main chemical constituents as steroids, triterpenoid saponins, diarylheptanes, flavonoids, and lignans, with the first two kinds being the major ones [7][8][9][10], which showed various pharmacological activities including lowering uric acid, anti-diabetic, anti-inflammation, anti-tumor, anti-atherosclerosis, regulating blood lipids, anti-oxidation, antibacterial [11]. Commonly, active compounds were usually obtained firstly by chromatographic techniques including silica gel column chromatography, macroporous resin column chromatography (MRCC), high-pressure preparative column chromatography, and preparative high-performance liquid chromatography, and then subjected to the activity assays by pharmacological tests.…”

Section: Introductionmentioning

confidence: 99%

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Efficient discovery of active isolates from Dioscorea spongiosa by the combination of bioassay‐guided macroporous resin column chromatography and high‐speed counter‐current chromatography

Wang,

Yu,

Zhao

et al. 2024

J of Separation Science

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In the present study, twelve compounds from Dioscorea spongiosa were successfully purified by an efficient technique combined bioassay‐guided fractionation macroporous resin column chromatography (MRCC) pretreatment and high‐speed counter‐current chromatography (HSCCC) separation for the first time. Then, D101 MRCC was used to fractionate the crude extract into five parts, which further applied the bioassay‐guided fractionation strategy to screen the active fractions of 2 and 4. As for the separation, 200 mg Fr.2 was purified by HSCCC using EtOAc/n‐BuOH/H2O (2:2:3, v/v), leading to annulatomarin (1), dioscoresides C (2), diosniponol C (3), methyl protodioscin (4), pseudoprotodioscin (5), protogracillin (6), as well as 200 mg Fr.4 yielding montroumarin (7), dioscorone A (8), diosniponol D (9), protodioscin (10), gracillin (11), and dioscin (12) using CH2Cl2/MeOH/H2O (3:3:2, v/v) with the purities over 95.0%. Finally, the isolates were assayed for their anti‐inflammatory, urico‐lowering, and anti‐diabetic activities in vitro, which indicated that the steroidal saponins of 5, 6, and 11 showed all these three activities.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Efficient discovery of active isolates from Dioscorea spongiosa by the combination of bioassay‐guided macroporous resin column chromatography and high‐speed counter‐current chromatography

Wang,

Yu,

Zhao

et al. 2024

J of Separation Science

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“…Gingerols, including shogaols, paradols, and gingerone, are the main flavoring substances and core medicinal ingredients of ginger [10]. Diarylheptanoids are a class of derivatives that consist of a 1,7-diarylheptane skeleton and include curcuminoids [11]. In addition to these compounds, flavonoids are reported to show antioxidant, anticancer, and other pharmacological activities [12,13].…”

Section: Introductionmentioning

confidence: 99%

Metabolomic analysis of bioactive compounds in mature rhizomes and daughter rhizomes in ginger (Zingiber officinale)

Chen

Tang

et al. 2019

Preprint

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Background The bioactive compounds of ginger (Zingiber officinale), such as gingerols, diarylheptanoids, and flavonoids, are of importance to human health because of their anticancer, antioxidant, and anti-inflammatory properties. The daughter rhizomes arise from mature rhizomes, but the pungency and pharmacological quality of the two rhizome types differ substantially.Results In this study, a metabolomic analysis was performed to investigate the biosynthesis of major bioactive compounds in the mature rhizome (R) and daughter rhizome (DR) in ginger. A total of 1212 differentially accumulated metabolites with p < 0.05 and |fold change| ≥ 1 were identified, of which 399 metabolites were more highly accumulated in R samples than in DR samples, whereas 211

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“…This is the first report of the isolation of diarylnonanoids from the Dioscorea genus. Although the diarylheptanoids are similar in structure, and have been previously isolated from the Dioscoreaceae family, − diarylnonanoids have a 9-carbon chain linking the two aromatic systems. Structurally similar compounds have been isolated from the Myristica genus in the plant family Myristicaceae. − Mosher ester analysis was used to deduce the absolute configuration of the chiral center (C-5) in compound 1 .…”

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confidence: 99%

Constituents of Two Dioscorea Species That Potentiate Antibiotic Activity against MRSA

2020

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The isolation of two diarylnonanoids from Dioscorea cotinifolia possessing antibiotic-potentiating activity against resistant strains of S. aureus are reported. The diarylnonanoids are a class of natural products similar in structure to the diarylheptanoids, which have a wide spectrum of reported biological activities. One of the diarylnonanoids (1) isolated possesses a chiral center and to deduce its configuration, the modified Mosher ester method was used. Using both 1D and 2D NMR data, as many protons as possible were assigned to both the Rand S-MTPA esters, and the configuration of the chiral center in 1 was determined to be R. Both the chiral and achiral diarylnonanoid (2) exhibited potent antibiotic-potentiating activity with the chiral natural product showing a greater tetracycline-potentiating activity than 2. Interestingly, 2 gave a higher norfloxacinpotentiating activity with a resultant higher efflux pump inhibitory activity. Manipulation of the structure of the diarylnonanoids through synthesis could lead to improved biological activity.

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Bioactive diarylheptanoids and stilbenes from the rhizomes of Dioscorea septemloba Thunb

Cited by 13 publications

References 9 publications

Efficient discovery of active isolates from Dioscorea spongiosa by the combination of bioassay‐guided macroporous resin column chromatography and high‐speed counter‐current chromatography

Efficient discovery of active isolates from Dioscorea spongiosa by the combination of bioassay‐guided macroporous resin column chromatography and high‐speed counter‐current chromatography

Metabolomic analysis of bioactive compounds in mature rhizomes and daughter rhizomes in ginger (Zingiber officinale)

Constituents of Two Dioscorea Species That Potentiate Antibiotic Activity against MRSA

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