Pregnane glycosides from Adonis amurensis and their bioactivity

Yan, Yonggao; Zhou, Di; Li, Xuezheng; Feng, Yuan; Wen, Xiaoyan; Wang, Yajun; An, Ru; Chen, Gang; Li, Ning

doi:10.1016/j.phytochem.2021.113046

Cited by 4 publications

(4 citation statements)

References 21 publications

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“…The 13 C NMR and DEPT spectroscopic data ( Table 3 ; Figure S2, Supplementary data ) of 1 displayed the signals for six methyls (one methoxy group), eight methylenes, twenty methines (including five olefinic/aromatic and thirteen oxygenated), and seven quaternary carbons (including two olefinic/aromatic and three carbonyls). The aforementioned data showed a similarity to those of periplocoside A [ 13 ], except for the presence of an additional carbonyl ( δ C 211.5), benzoyl group, and sp 3 methyl group ( δ C 12.1); however, the absence of a dioxygenated quaternary carbon ( δ C 115.7) and the C-18 ester carbonyl in 1 indicated that 1 was a typical pregnane glycoside with a benzoyl group and 2 sugar moieties. The changes were confirmed by the key HMBC correlations ( Figure 2 ) from H-6 ( δ H 1.46, m; 1.41, m), H-9 ( δ H 3.29, d, J = 10.0 Hz), and H-7 ( δ H 2.05; 2.22) to C-8 ( δ C 211.5); from H-18 ( δ H 1.19, s) to C-12 ( δ C 81.0), C-13 ( δ C 55.8), and the hemiketal carbon C-14 ( δ C 115.7); and from H-11 ( δ H 5.06) to C-14.…”

Section: Resultsmentioning

confidence: 81%

“…Further elucidation of the 2D NMR spectra confirmed the above assignments. By comparison of the R f values and optical rotations of the acidic-hydrolyzed sugars of compound 3 , the sugars were identified as D-oleandrose and D-glucose [ 8 , 13 , 17 ]. Thus, the structure of compound 3 was defined to be marsdeoside C.…”

Section: Resultsmentioning

confidence: 99%

“…This change was corroborated by the key HMBC correlation from H-12 (δ H 5.62) to C-1′′ ( δ C 166.8) and the 1 H- 1 H COSY correlations of H-3′′/H-4′′/H-5′′/H-6′′/H-7′′ ( Figure 2 ). By comparison of the Rf and optical rotations of the sugars that hydrolyzed from 4 in an acidic condition, the sugars were identified as D-oleandrose and D-glucose [ 8 , 13 , 17 ]. Therefore, the structure of compound 4 was defined to be marsdeoside D.…”

Section: Resultsmentioning

confidence: 99%

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Nine New Pregnane Glycosides from the Cultivated Medicinal Plant Marsdenia tenacissima

et al. 2023

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The ethnobotanical plant Marsdenia tenacissima has been used for hundreds of years for Dai people in Yunnan Province, China. Previously, chemical investigations on this plant have revealed that pregnane glycosides were the main biological constituents. Nine new pregnane glycosides, marsdeosides A–I (1–9), were isolated from cultivated dried stems of the medicinal plant Marsdenia tenacissima in this study. The structures were analyzed by extensive spectroscopic analysis, including 1D, 2D NMR, HRESIMS, and IR spectroscopic analysis. The absolute configurations of the sugar moieties were identified by comparing the Rf values and specific optical rotations with those of the commercially available standard samples and the data reported in the literature. Marsdeosides A (1) featured an unusual 8,14-seco-pregnane skeleton. Compounds 1, 8, and 9 showed activity against nitric oxide production in lipopolysaccharide-activated macrophage RAW264.7, with IC50 values of 37.5, 38.8, and 42.8 μM (L-NMMA was used as a positive control, IC50 39.3 μM), respectively. This study puts the knowledge of the chemical profile of the botanical plant M. tenacissima one step forward and, thereby, promotes the sustainable utilization of the resources of traditional folk medicinal plants.

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Section: Resultsmentioning

confidence: 81%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Nine New Pregnane Glycosides from the Cultivated Medicinal Plant Marsdenia tenacissima

et al. 2023

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“…Adonis amurensis Regel & Radde is an important early spring short-lived herbaceous flower plant member of the Ranunculaceae family. It is principally distributed in Northeastern China, Korea, and Japan, where its organs are widely used as a traditional folk medicine to treat heart palpitations, epilepsy, and edema [ 15 , 16 ]. The sexual reproduction process of early spring short-lived plants includes a long underground development process of flower organs and rapid blossoming after overwintering [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Dynamic transcriptome analysis provides molecular insights into underground floral differentiation in Adonis Amurensis Regel & Radde

Xin,

Zhang,

Wang

et al. 2024

BMC Genom Data

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Understanding flower developmental processes is a prerequisite for improving flowering ‘plants’ production. Adonis amurensis is a fascinating spring ephemeral plant that develops its flower organs underground. Nevertheless, knowledge of the molecular mechanisms driving this particular process is scarce. Herein, we examined transcriptional changes during underground flower differentiation in A. amurensis and unveiled key differently regulated genes and pathways. High-throughput RNA sequencing of meristems at different flower developmental stages, including flower primordium (FP), sepal stage (SE), perianth primordium (PE), stamen stage (ST), and pistil stage (PI), identified 303,234 unigenes that showed 44.79% similarity with sequences in Aquilegia coerulea. Correlations, principal component, and differentially expressed genes (DEGs) analyses revealed that few molecular changes occurred during the transition from PE to ST. Many DEGs exhibited stage-specific regulations. Transcription factor (TF) and phytohormone family genes are critical regulators of the floral differentiation process in A. amurensis. The most differentially regulated TFs were MADS, FAR1, MYBs, AP2/ERF, B3, C2H2, and LOBs. We filtered out 186 candidate genes for future functional studies, including 18 flowering/circadian-related, 32 phytohormone-related, and TF family genes. Our findings deepen our understanding of the underground flower differentiation process and offer critical resources to dissect its regulatory network in A. amurensis. These findings establish a foundational platform for researchers dedicated to exploring the unique phenotypic characteristics of this specific flowering modality and delving into the intricate molecular mechanisms underpinning its regulation and expression.

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Search for new steroidal glycosides with anti-cancer potential from natural resources

Matsuo,

Mimaki

2024

J Nat Med

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Chemical investigations of higher plants, with particular attention paid to their steroidal glycosides, present a promising approach for generating anti-cancer agents from natural products. We conducted a systematic phytochemical investigation of nine higher plants—whole plants and rhizomes of Convallaria majalis, whole plants of Agave utahensis, roots of Adonis amurensis, seeds of Adonis aestivalis, bulbs of Bessera elegans, bulbs of Fritillaria meleagris, seeds of Digitalis purpurea, underground parts of Yucca glauca, and bulbs of Lilium pumilum—which led to the discovery of novel steroidal glycosides. The structures of these new constituents were determined based on spectroscopic data and chemical transformations. The identification of the monosaccharides including their absolute configurations was carried out by direct HPLC analysis of their hydrolysates using an optical rotation detector. Cytotoxicity of the isolated steroidal glycosides was evaluated against various tumor cells (A549, ACHN, HepG-2, HL-60, HSC-2, HSC-3, HSC-4, HSG, and SBC-3) and normal cells (Fa2 N-4, HK-2, and TIG-3 cells). Certain steroidal glycosides exhibit selective cytotoxicity and synergistic effects, making them potential lead compounds for use as anti-cancer agents. We document the isolation of 139 steroidal glycosides from higher plants and assessment their cytotoxic activities. Graphical abstract

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Pregnane glycosides from Adonis amurensis and their bioactivity

Cited by 4 publications

References 21 publications

Nine New Pregnane Glycosides from the Cultivated Medicinal Plant Marsdenia tenacissima

Nine New Pregnane Glycosides from the Cultivated Medicinal Plant Marsdenia tenacissima

Dynamic transcriptome analysis provides molecular insights into underground floral differentiation in Adonis Amurensis Regel & Radde

Search for new steroidal glycosides with anti-cancer potential from natural resources

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