2018
DOI: 10.1021/acs.orglett.8b03306
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Vlasoulamine A, a Neuroprotective [3.2.2]Cyclazine Sesquiterpene Lactone Dimer from the Roots of Vladimiria souliei

Abstract: Vlasoulamine A (1), an unprecedented sesquiterpene lactone dimer featuring a fully hydrogenated pyrrolo[2,1,5-cd]indolizine core, and vlasoulones A and B (2 and 3), a pair of epimeric dimers formed from a proposed Diels−Alder [4 + 2] cycloaddition between a germacrane sesquiterpene lactone and a eudesmane sesquiterpene, were isolated from the roots of Vladimiria souliei. Their structures and absolute configurations were established by NMR, MS, and single-crystal X-ray spectroscopic analysis. Moreover, 1 exhibi… Show more

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Cited by 31 publications
(14 citation statements)
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“…[46] It is,t herefore, possible that natural product scaffolds exist in nature which resemble the structures of the new NP-inspired compound classes resulting from our approach thereby further validating it. In agreement with this notion, very recently and while we developed the principle,t he isolation of the natural product vlasoulamine Awas reported, [47] whose scaffold is structurally related to pseudo-sesquiterpenoid alkaloids 36.…”
Section: Discussionmentioning
confidence: 68%
“…[46] It is,t herefore, possible that natural product scaffolds exist in nature which resemble the structures of the new NP-inspired compound classes resulting from our approach thereby further validating it. In agreement with this notion, very recently and while we developed the principle,t he isolation of the natural product vlasoulamine Awas reported, [47] whose scaffold is structurally related to pseudo-sesquiterpenoid alkaloids 36.…”
Section: Discussionmentioning
confidence: 68%
“…The ED 50 of compound 377 on the production of NO was 5.73, and obviously inhibited LPS-inducediNOS and COX-2 protein expression in a dose-dependent way, and increased HO-1 protein expression at the concentration of 10 µM [92].Three axane sesquiterpenoid isonitrile pictaisonitrile-1 (378), pictaisonitrile-2 (379), and cavernothiocyanate (380) (Figure 11) were extracted from hyllidiapicta collected from Bali, Indonesia [71]. Vlasoulamine A (381) (Figure 11), an unprecedented guaiane sesquiterpene lactone dimerfeaturing a fully hydrogenated pyrrolo[2,1,5-cd] indolizine core, was isolated from the roots of Vladimiria souliei [93]. Moreover, 381 exhibited neuroprotective activity whenevaluated for glutamate-induced cytotoxicity, nuclear Hoechst 33,258 staining, and measuring intracellular reactive oxygen species levels, using a rat pheochromocytoma PC12 cell-based model system [93].…”
Section: Cyclonerane Axane Nardosinane Zizaane Eremophilane and Guaiane Sesquiterpenoidsmentioning
confidence: 99%
“…Vlasoulamine A (381) (Figure 11), an unprecedented guaiane sesquiterpene lactone dimerfeaturing a fully hydrogenated pyrrolo[2,1,5-cd] indolizine core, was isolated from the roots of Vladimiria souliei [93]. Moreover, 381 exhibited neuroprotective activity whenevaluated for glutamate-induced cytotoxicity, nuclear Hoechst 33,258 staining, and measuring intracellular reactive oxygen species levels, using a rat pheochromocytoma PC12 cell-based model system [93]. Clavukoellians A-D (382-385) (Figure 11), highly rearranged nardosinane Sesquiterpenoids with antiangiogenic activity were purified from the marine soft coral Clavularia koellikeri [94].…”
Section: Cyclonerane Axane Nardosinane Zizaane Eremophilane and Guaiane Sesquiterpenoidsmentioning
confidence: 99%
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“…At the same time, we also have separated some rare dimeric sesquiterpenes exhibiting potential neuroprotection activity from Vladimiria souliei in our previous study. 15,16 Therefore, as a continuing investigation on this plant, two C 32 sesquiterpene dimers, vlasoulides A and B (1 and 2), were isolated from the same plant. Herein, we describe the isolation, structural elucidation and neuroprotective activities of two new compounds (Fig.…”
Section: Introductionmentioning
confidence: 99%