Micranthanosides I and II, two novel 1,10-secograyanane diterpenoids and their antinociceptive analogues from the leaves and twigs of <i>Rhododendron micranthum</i>

Zhu, Yuxun; Yan, Huimin; Wang, Xiaojing; Zhang, Zhaoxin; Zhang, Huanping; Chai, Li-Sha; Li, Li; Qu, Jing; Li, Yong

doi:10.1039/c9ra01736d

Cited by 14 publications

(1 citation statement)

References 28 publications

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“…Cells were seeded in 96 well culture plates, and pretreated with the tested compounds (50 µM) and stimulated with LPS (1 μg/mL) for 24 h. The supernatant was mixed with an equal volume of Griess reagent (1% sulfanilamide, 0.1% naphthylethylenediamine dihydrochloride, and 2.5% phosphoric acid) and incubated at room temperature for 24 h. The concentration of nitrite was measured by reading the absorbance at 570 nm. 21,22 L-NMMA was used as a positive control.…”

Section: Methodsmentioning

confidence: 99%

Artemisiaside A: A new Lignan Glycoside and its Analogues From the Aerial Parts of Artemisia argyi

Tong

Tao

Zhang

et al. 2022

Natural Product Communications

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Chemical analysis of the aerial parts of Artemisia argyi H. Lév. & Vaniot led to the isolation of 6 lignans, including a new lignan glycoside, artemisiaside A, using various chromatographic techniques. Detailed spectroscopic (including 1D, 2D- nuclear magnetic resonance) and high resolution mass spectroscopy procedures, and electronic circular dichroism were used to ascertain the structural orientations of these compounds. The anti-inflammatory activities of compounds 1 to 6 were evaluated by measuring their inhibitory effects on lipopolysaccharide (LPS) -induced nitric oxide (NO) production in RAW264.7 LPS-activated macrophages. At 50 μM, compound 1 showed moderate anti-inflammatory activity with an inhibition rate of 61.2%.

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Section: Methodsmentioning

confidence: 99%

Artemisiaside A: A new Lignan Glycoside and its Analogues From the Aerial Parts of Artemisia argyi

Tong

Tao

Zhang

et al. 2022

Natural Product Communications

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Epoxymicranthols A—N, 5,9‐Epoxygrayanane Diterpenoids as Potent Analgesics from Rhododendron micranthum

Jin

Yuan

et al. 2021

Chin. J. Chem.

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Main observation and conclusion Fifteen 5,9‐epoxygrayanane diterpenoids (1—15) including fourteen new ones, epoxymicranthols A—N (1—14), were isolated from the leaves extract of Rhododendron micranthum. Their structures were elucidated via extensive spectroscopic methods and 13C NMR‐DP4+ analysis, and the absolute configurations of 1, 3—10, 14, and 15 were confirmed by single‐crystal X‐ray diffraction analysis. Epoxymicranthols A—C (1—3) represent the first examples of 14α‐hydroxygrayanane diterpenoids, and epoxymicranthols C—F (3—6) are the first examples of 10β‐hydroxy‐5,9‐epoxygrayanane diterpenoids. Meanwhile, epoxymicranthols K (11) and N (14) represent the first examples of 13‐hydroxy‐5,9‐epoxygrayanane and 5,9‐epoxygrayan‐3‐one diterpenoids, respectively. All the diterpenoids (1—15) were assayed for their analgesic activities, and all of them exhibited significant analgesic activities at a dose of 5.0 mg/kg. Among them, compounds 2, 7, 8, and 10 also exhibited significant analgesic activities even at lower doses of 1.0 and 0.2 mg/kg. More importantly, epoxymicranthol G (7) still expressed potent analgesic activity at a lower dose of 0.04 mg/kg. A preliminary structure‐activity relationship for the analgesic effects of 5,9‐epoxygrayanane diterpenoids 1—15 is discussed. These results not only enlarged the structural diversity of 5,9‐epoxygrayanane diterpenoids, but also provided a basis to develop novel potent analgesics.

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Structurally diverse diterpenoids from Pieris japonica as potent analgesics

Zheng

Jin

Huang

et al. 2020

Bioorganic Chemistry

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Micranthanosides I and II, two novel 1,10-secograyanane diterpenoids and their antinociceptive analogues from the leaves and twigs of Rhododendron micranthum

Abstract: Two unusual diterpenoids with a new 1,10-secograyanane skeleton and thirteen new analogues from the leaves and twigs of Rhododendron micranthum were obtained.

Cited by 14 publications

References 28 publications

Artemisiaside A: A new Lignan Glycoside and its Analogues From the Aerial Parts of Artemisia argyi

Artemisiaside A: A new Lignan Glycoside and its Analogues From the Aerial Parts of Artemisia argyi

Epoxymicranthols A—N, 5,9‐Epoxygrayanane Diterpenoids as Potent Analgesics from Rhododendron micranthum

Structurally diverse diterpenoids from Pieris japonica as potent analgesics

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