Stelleralides A–C, Novel Potent Anti-HIV Daphnane-Type Diterpenoids from <i>Stellera chamaejasm</i>e L.

Asada, Yujiro; Sukemori, Aya; Watanabe, Takashi; Malla, Kuber Jung; Yoshikawa, Takafumi; Li, Wei; Koike, Kazuo; Chen, Chin Ho; Akiyama, Tsuyoshi; Qian, Keduo; Nakagawa‐Goto, Kyoko; Morris‐Natschke, Susan L.; Lee, Kuo Hsiung̀

doi:10.1021/ol200889s

Cited by 83 publications

(82 citation statements)

References 24 publications

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“…As confirmed from the molecular formula, the 1 H and 13 C NMR revealed that the aliphatic chain of compounds 4 and 5 contained two more and four more methylene groups than mellerin B respectively. By detailed MS and NMR data analysis, compound 4 was identified as simplexin, a known compound previously isolated from the genus Pimelea (Thymelaeaceae) including P.simplex and P. elongata and other plant species (Asada et al, 2011;Hayes et al, 2010). Compound 5 was identified as montanin, from its MS and NMR data analysis and also in comparison with data from literature.…”

Section: Characterisation Of Compounds From the Stem Bark Extractmentioning

confidence: 90%

Antiplasmodial compounds from the stem bark of Neoboutonia macrocalyx pax

Namukobe

Kiremire

Boyer

et al. 2015

Journal of Ethnopharmacology

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Section: Characterisation Of Compounds From the Stem Bark Extractmentioning

confidence: 90%

Antiplasmodial compounds from the stem bark of Neoboutonia macrocalyx pax

Namukobe

Kiremire

Boyer

et al. 2015

Journal of Ethnopharmacology

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“…19 The purity of gnidimacrin (>98%) was confirmed by quantitative high-performance liquid chromatography photo-diode array (HPLC-PDA) analysis and 1 H NMR spectroscopic analysis. Prostratin, staurosporin, and enzastaurin were purchased from LC Laboratories, Woburn, MA.…”

Section: Methodsmentioning

confidence: 99%

Gnidimacrin, a Potent Anti-HIV Diterpene, Can Eliminate Latent HIV-1 Ex Vivo by Activation of Protein Kinase C β

Wei¹,

Huang²,

Zhu³

et al. 2015

J. Med. Chem.

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HIV-1 latency-reversing agents, such as histone deacetylase inhibitors (HDACIs), were ineffective in reducing latent HIV-1 reservoirs ex vivo using CD4 cells from patients as a model. This deficiency poses a challenge to current pharmacological approaches for HIV-1 eradication. The results of this study indicated that gnidimacrin (GM) was able to markedly reduce the latent HIV-1 DNA level and the frequency of latently infected cells in an ex vivo model using patients peripheral blood mononuclear cells (PBMC). GM induced approximately 10-fold more HIV-1 production than the HDACI SAHA or romidepsin, which may be responsible for the effectiveness of GM in reducing latent HIV-1 levels. GM achieved these effects at low picomolar concentrations by selective activation of protein kinase C βI and βII. Notably, GM was able to reduce the frequency of HIV-1 latently infected cells at concentrations without global T cell activation or stimulating inflammatory cytokine production. GM merits further development as a clinical trial candidate for latent HIV-1 eradication.

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“…11,19 In particular, certain daphnane and tigliane diterpenoids have shown extremely potent anti-HIV activity at low nanomolar concentrations with relatively low cytotoxicity. 7,10 However, these compounds are very difficult to synthesize because of their complex structure. Accordingly, further analysis of the plant material was conducted to acquire a significant quantity of several known, as well as new, anti-HIV diterpenoids from S. chamaejasme .…”

mentioning

confidence: 99%

Stelleralides D–J and Anti-HIV Daphnane Diterpenes from Stellera chamaejasme

Yan

Chen

et al. 2015

J. Nat. Prod.

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Bioassay-guided fractionation of a petroleum ether extract of the roots of Stellera chamaejasme led to the isolation of seven new (stelleralides D–J, 1–7) and 12 known (8–19) daphnane diterpenoids. The structures and relative configurations of 1–7 were established on the basis of extensive spectroscopic analysis, including HRESIMS and comprehensive NMR techniques. All isolates were evaluated for anti-HIV activity in MT4 cells. All compounds tested, except 2, showed anti-HIV activity, and, especially, five 1α-alkyldaphnane diterpenoids (3, 4, 5, 10, and 11) exhibited extremely potent anti-HIV activity, with EC50 values of 0.06–1.1 nM and selectivity index values of more than 10 000.

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Stelleralides A–C, Novel Potent Anti-HIV Daphnane-Type Diterpenoids from Stellera chamaejasme L.

Cited by 83 publications

References 24 publications

Antiplasmodial compounds from the stem bark of Neoboutonia macrocalyx pax

Antiplasmodial compounds from the stem bark of Neoboutonia macrocalyx pax

Gnidimacrin, a Potent Anti-HIV Diterpene, Can Eliminate Latent HIV-1 Ex Vivo by Activation of Protein Kinase C β

Stelleralides D–J and Anti-HIV Daphnane Diterpenes from Stellera chamaejasme

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