Grayanane diterpenoids with diverse bioactivities from the roots of Pieris formosa

Niu, Chang‐Shan; Li, Yong; Liu, Yun‐Bao; Ma, Shuang‐Gang; Liu, Fei; Cui, Li; Yu, Haibo; Wang, Xiaojing; Qu, Jing; Yu, Shi‐Shan

doi:10.1016/j.tet.2017.11.018

Cited by 17 publications

(11 citation statements)

References 17 publications

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“…The dereplication study revealed that molecule at m/z [M+] 592.268 is corresponding to molecular formula (C 35 H 36 N 4 O 5 ) which may be phaeophorbide A that is a chlorophyll degradation product formed by enzymic hydrolysis of phaeophytin A by chlorophyllase. More interestingly, signal at m/z 402.225 is equivalent to molecular formula C 20 H 34 O 8 that may correspond to either taxane or grayanane type of diterpenoid molecule i.e., pierisformosoid which was reported in the literature for its cytotoxic, analgesic and antifeedant properties [ 71 , 72 ]. The PCA and dereplication results matched with the investigated biological activities of the Euphorbia’s crude extracts which emphasized the cytotoxic properties of E .…”

Section: Discussionmentioning

confidence: 99%

Cytotoxic Activity and Metabolic Profiling of Fifteen Euphorbia Species

et al. 2020

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Euphorbia is a large genus of flowering plants with a great diversity in metabolic pattern. Testing the cytotoxic potential of fifteen Euphorbia species revealed highest activity of E. officinarum L. against human colon adenocarcinoma (CACO2) cell line (IC50 7.2 µM) and of E. lactea Haw. against human hepatoma (HepG2) and human breast adenocarcinoma (MCF-7) cell lines (IC50 5.2 and 5.1 µM, respectively). Additionally, metabolic profiling of the fifteen tested species, using LC-HRMS, for dereplication purposes, led to the annotation of 44 natural compounds. Among the annotated compounds, diterpenoids represent the major class. Dereplication approach and multivariate data analysis are adopted in order to annotate the compounds responsible for the detected cytotoxic activity. Results of Principle component analysis (PCA) come in a great accordance with results of biological testing, which emphasized the cytotoxic properties of E. lactea Haw. A similarity correlation network showed that the two compounds with the molecular formula C16H18O8 and C20H30O10, are responsible for cytotoxic activity against MCF-7 and HepG2 cell lines. Similarly, the compound with molecular formula C18H35NO correlates with cytotoxic activity against CACO2.

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Section: Discussionmentioning

confidence: 99%

Cytotoxic Activity and Metabolic Profiling of Fifteen Euphorbia Species

et al. 2020

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“…Diterpenes from the genus Pieris have been highlighted as sources of insect antifeedant compounds [ 98 ]. The compounds pierisformosoid A ( 29 ), D ( 30 ) and I ( 31 ), asebotoxin ( 32 ) and kalmitoxin II ( 33 ) ( Figure 21 ) at a dose of 0.5 mg/mL showed antifeedant activities against Plutella xylostella , with inhibition ratios of 92.3%, 60.2%, 73.7%, 78.8 and 45.7%, respectively [ 102 ]. The diterpenes pierisoid C ( 34 ) and E ( 35 ), together with asebotoxin IV ( 36 ) ( Figure 21 ) exhibited antifeedant activity against the beet armyworm Spodoptera exigua with EC 50 values of 10.91, 33.89, 6.58 µg·cm −2 , respectively [ 98 ].…”

Section: Toxicity Of Diterpenesmentioning

confidence: 99%

An Overview of Biotransformation and Toxicity of Diterpenes

2018

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Diterpenes have been identified as active compounds in several medicinal plants showing remarkable biological activities, and some isolated diterpenes are produced at commercial scale to be used as medicines, food additives, in the synthesis of fragrances, or in agriculture. There is great interest in developing methods to obtain derivatives of these compounds, and biotransformation processes are interesting tools for the structural modification of natural products with complex chemical structures. Biotransformation processes also have a crucial role in drug development and/or optimization. The understanding of the metabolic pathways for both phase I and II biotransformation of new drug candidates is mandatory for toxicity and efficacy evaluation and part of preclinical studies. This review presents an overview of biotransformation processes of diterpenes carried out by microorganisms, plant cell cultures, animal and human liver microsomes, and rats, chickens, and swine in vivo and highlights the main enzymatic reactions involved in these processes and the role of diterpenes that may be effectively exploited by other fields.

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“…This is the first report of the crystal structure of a grayanane diterpenoid glucoside. More importantly, 3- epi -grayanoside B ( 1 ) represents the first example of a 3α-oxygrayanane diterpenoid glucoside, although the first 3α-oxygrayanane diterpenoid aglycone, pierisformosoid E, was recently reported …”

Section: Results and Discussionmentioning

confidence: 99%

“…More importantly, 3-epi-grayanoside B (1) represents the first example of a 3α-oxygrayanane diterpenoid glucoside, although the first 3α-oxygrayanane diterpenoid aglycone, pierisformosoid E, was recently reported. 30 Micranthanoside A (2), colorless prisms (MeOH), mp 133− 134 °C, showed an [M + Na] + ion at m/z 505.2762 in the HRESIMS. Using the 13 C NMR data, the molecular formula of micranthanoside A (2) was determined to be C 26 H 42 O 8 (calcd for C 26 H 42 O 8 Na, 505.2777), which has one less oxygen atom than the known compound grayanoside C (15).…”

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confidence: 99%

Grayanane Diterpenoid Glucosides from the Leaves of Rhododendron micranthum and Their Bioactivities Evaluation

et al. 2018

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Thirteen new grayanane diterpenoid glucosides, 3-epi-grayanoside B (1), micranthanosides A−E (2−6), 7αhydroxygrayanoside C (7), micranthanoside F (8), 14β-acetyoxymicranthanoside F (9), micranthanoside G (10), 14-Oacetylmicranthanoside G (11), 14β-hydroxypieroside A (12), and micranthanoside H (13), and six known analogues (14−19) were isolated from the leaves of Rhododendron micranthum. The structures of 1−19 were elucidated based on spectroscopic analysis, comparison with literature, and chemical methods. The absolute configurations of 3-epi-grayanoside B (1) and micranthanosides A (2) and C (4) were defined by single-crystal X-ray diffraction analysis. This is the first report of the crystal structures of grayanane diterpenoid glucosides. 3-epi-Grayanoside B (1) represents the first example of a 3α-oxygrayanane diterpenoid glucoside, and micranthanosides A−D (2−5) are the first examples of 5α-hydroxy-1-βH-grayanane diterpenoids. In addition, micranthanosides C−F (4−6 and 8) and 14β-acetyoxymicranthanoside F (9) represent the first examples of grayanane glucosides with the glucosylation at C-16.All the grayanane diterpenoid glucosides 1−19 were assayed for their antiinflammatory, antitumor, and PTP1B inhibitory activities, but did not show significant activities at 40 μM. Grayanane diterpenoid glucosides 1−18 were evaluated for their antinociceptive activity, and compounds 2, 3, 7−10, 12, 13, and 16 showed significant antinociceptive effects with percentage inhibitions in excess of 50%.

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Grayanane diterpenoids with diverse bioactivities from the roots of Pieris formosa

Cited by 17 publications

References 17 publications

Cytotoxic Activity and Metabolic Profiling of Fifteen Euphorbia Species

Cytotoxic Activity and Metabolic Profiling of Fifteen Euphorbia Species

An Overview of Biotransformation and Toxicity of Diterpenes

Grayanane Diterpenoid Glucosides from the Leaves of Rhododendron micranthum and Their Bioactivities Evaluation

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