Artesin A, a new cage-shaped dimeric guaianolide from Artemisia sieversiana

Zhou, Xu-Dong; Chai, Xingyun; Zeng, Ke‐Wu; Zhao, Ming; Jiang, Yong; Tu, Peng‐Fei

doi:10.1016/j.tetlet.2015.01.081

Cited by 26 publications

(7 citation statements)

References 12 publications

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“…3) and coupling constants. The H-7 of guaiane-type sesquiterpenoids always maintained the α-orientation; [25][26][27] thus, the large coupling constant…”

Section: Resultsmentioning

confidence: 99%

“…3) and coupling constants. The H-7 of guaiane-type sesquiterpenoids always maintained the α-orientation; 25–27 thus, the large coupling constant between H-6 and H-7 ( J = 9.7 Hz) indicated that H-6 was in β-orientation. Similarly, the large coupling constant between H-6′ and H-7′ ( J = 11.0 Hz) indicated that H-6′ was assigned to be β-orientated.…”

Section: Resultsmentioning

confidence: 99%

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Artemongolides A–F, undescribed sesquiterpenoid dimers from Artemisia mongolica and their antihepatic fibrosis activities

et al. 2023

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“…3) and coupling constants. The H-7 of guaiane-type sesquiterpenoids always maintained the α-orientation; [25][26][27] thus, the large coupling constant…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Artemongolides A–F, undescribed sesquiterpenoid dimers from Artemisia mongolica and their antihepatic fibrosis activities

et al. 2023

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“…Up to now, a variety of sesquiterpenoid dimers with potential in the treatment of liver cancer [ 6‐7 ] and antiinflammatory activities have been isolated from Artemisia species. [ 8‐19 ] Guaiane‐type sesquiterpenoid dimers are the main classes of sesquiterpenoid dimers in this genus, predominantly composed of two alike or unlike monomeric sesquiterpene lactone units through different connecting model. Chemical investigations showed that 77 guaiane‐type sesquiterpenoid dimers had been identified from Artemisia plants in the last 40 years, and most of them were generated via intermolecular Diels–Alder reaction to produce an additional cyclohexene moiety.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Artematrovirenolides A—D and Artematrolides S—Z, Sesquiterpenoid Dimers with Cytotoxicity against Three Hepatoma Cell Lines from Artemisia atrovirens

et al. 2021

Chin. J. Chem.

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Comprehensive Summary Inspired by the intriguing structures and remarkable activities of sesquiterpenoid dimers, 12 new sesquiterpenoid dimers, artematrovirenolides A—D (1—4) and artematrolides S—Z (8—12), were isolated from the EtOAc fraction of Artemisia atrovirens through a bioactivity‐guided approach. Their structures were elucidated by comprehensive spectroscopic data and absolute configuration was assigned based on single crystal X‐ray diffraction data and ECD calculations. Structurally, all compounds are presumably formed via [4+2] cycloaddition involving three connecting model. Compounds 1—4 are four novel hetero‐dimeric [4+2] Diels–Alder adducts dimerized from a rotundane‐type unit and a guaiane‐type monomer, and compounds 5—12 are eight new homo‐dimeric [4+2] adducts derived from two guaianolide moieties. A putative biosynthetic pathway for compounds 1—4 was also proposed. Compounds 4, 6, 7, and 10 demonstrated moderate cytotoxicity against HepG2, SMMC‐7721, and Huh7 cell lines with IC50 values ranging from 9.3 to 62.3 μmol/L. Interestingly, compounds 5 and 11 manifested cytotoxicity with IC50 values of 13.6 and 12.8 (HepG2), 18.5 and 13.1 (SMMC‐7721), and 16.5 and 19.4 μmol/L (Huh7), respectively, which were equivalent to the positive control, sorafenib. This investigation suggests that compounds 5 and 11 might be considered as potent antihepatoma candidates and deserve further structural modification and mechanism study.

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“…conclusion, this study investigated chemically the aerial parts of Artemisia sieversiana, which resulted in ten dibenzocyclooctadiene lignans(1)(2)(3)(4)(5)(6)(7)(8)(9)(10), including two unknown ones(1)(2). Their structures were elucidated from extensive spectroscopic analysis, including MS, NMR and circular dichroism experiments.…”

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confidence: 99%

Dibenzocyclooctadiene Lignans from Artemisia sieversiana and Their Nitric Oxide Inhibitory Effects

Zhou¹,

Chen²,

Zheng³

et al. 2020

Preprint

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Two previously undescribed dibenzocyclooctadiene lignans, named sieverlignans D–E (1-2), as well as eight known ones (3-10), were isolated from the aerial parts of Artemisia sieversiana. Their structures were elucidated from extensive spectroscopic analysis, including HRMS, NMR and circular dichroism experiments. This study is the first to report dibenzocyclooctadiene lignans in the genus Artemisia and this plant. All the compounds were evaluated for their anti-neuroinflammatory effects on the lipopolysaccharides (LPS)-induced nitric oxide production in BV-2 murine microglial cells. Compounds 1 and 6 exhibited the moderate activity with their IC50 values of 47.7 and 21.9 μM, compared to a positive control quercetin with the IC50 value of 16.0 μM.

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Artesin A, a new cage-shaped dimeric guaianolide from Artemisia sieversiana

Cited by 26 publications

References 12 publications

Artemongolides A–F, undescribed sesquiterpenoid dimers from Artemisia mongolica and their antihepatic fibrosis activities

Artemongolides A–F, undescribed sesquiterpenoid dimers from Artemisia mongolica and their antihepatic fibrosis activities

Artematrovirenolides A—D and Artematrolides S—Z, Sesquiterpenoid Dimers with Cytotoxicity against Three Hepatoma Cell Lines from Artemisia atrovirens

Dibenzocyclooctadiene Lignans from Artemisia sieversiana and Their Nitric Oxide Inhibitory Effects

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