An Efficient Method for Determining the Relative Configuration of Furofuran Lignans by 1H NMR Spectroscopy

Shao, Siyuan; Yang, Yanan; Feng, Zi‐Ming; Jiang, Jian‐Shuang; Zhang, Pei‐Cheng

doi:10.1021/acs.jnatprod.8b00044

Cited by 53 publications

(25 citation statements)

References 37 publications

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“…7 The 1D and HSQC NMR data also exhibited the presence of two olefinic groups (δ H /δ C 6.82 (1H, td, J = fraction that showed the highest tyrosinase inhibition activity. 10 These results are consistent with those reported in prior literature. 11 μL of L-tyrosine (1.5 mM) was added to the reaction mixture (300 μL).…”

Section: Resultssupporting

confidence: 93%

α-Glucosidic Hydroquinone Derivatives from Viburnum Erosum

Park

Lee

Jang

et al. 2021

Preprint

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Six new compounds (1−6) were isolated from the leaves of Viburnum erosum along with four known compounds 7−10. The structures were determined by NMR and MS spectroscopic analyses, and their absolute configurations were established by chemical and spectroscopic methods. Compounds 1–6 were α-glucosidic hydroquinone derivatives with different linear monoterpenoid structures. Compounds 1−10 were also evaluated for their tyrosinase inhibitory activities, and 10 showed potent inhibition of tyrosinase enzyme with IC50 of 37.9 μM compared to 47.6 μM of the positive control (β-arbutin).

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Section: Resultssupporting

confidence: 93%

α-Glucosidic Hydroquinone Derivatives from Viburnum Erosum

Park

Lee

Jang

et al. 2021

Preprint

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“…The configuration of furofuran moiety in 1 was to be same as that of (+)-paulownin and (+)-1-hydroxysyringaresinol 1-glucoside based on the NMR data and optical rotation. 10,14) In addition, the trans/trans configuration of 7-H/8-OH and 7′-H/8′-H in the furofuran moiety was confirmed by comparison with the chemical shift differences. 15) Thus, the structure of 1 was determined (Fig.…”

Section: Introductionmentioning

confidence: 80%

“…10,14) In addition, the trans/trans configuration of 7-H/8-OH and 7′-H/8′-H in the furofuran moiety was confirmed by comparison with the chemical shift differences. 15) Thus, the structure of 1 was determined (Fig. 1 Tables 1 and 2) were almost identical to those of 5-methoxybalanophonin, which was isolated from the same plant source, 9) except for the additional glucose moiety [δ .…”

Section: Introductionmentioning

confidence: 80%

Three New Lignan Glycosides from the Firmiana simplex

et al. 2019

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In our quest for structurally intriguing compounds from Korean medicinal plant sources, chromatographic separation of the 80% MeOH extract from Firmiana simplex resulted in the isolation and identification of three new lignan glycosides (1-3), together with six known lignan glycosides (4-9). The structures of 1-3 were determined on the basis of spectroscopic analyses, including extensive 2D-NMR and enzyme hydrolysis. Nitric oxide (NO) production was evaluated in the lipopolysaccharide-activated microglial cell line, BV-2 to investigate the anti-neuroinflammatory effects of the isolated compounds (1-9). Compound 7 marginally inhibited NO levels with IC 50 values of 59.83 µM.

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“…Furofuran lignans have their configuration well established in literature, according to Shao et al [66], the 7, 9 :7 , 9-diepoxi moiety of furofuran lignans of natural origin occurs in the cis-fused configuration. The experiments carried out have demonstrated that chemical deviations of the ∆δH-9 and ∆δH-9 are resulted of relative configurations of the C-7/C-8 and C-7 /C-8 .…”

Section: Isolation and Identification Of Lignansmentioning

confidence: 94%

“…The compounds secoisolariciresinol [63], pinoresinol-4-O-β-d-glucopyranoside [64], pinoresinol-4-O-β-d-apiofuranosyl-(1→2)-β-d-glucopyranoside [65], epipinoresinol-4-O-β-d-glucopyranoside [66] and were isolated from the fractionation of the crude ethanolic extract of thespecies Justicia aequilabris (Nees) Lindau [67] collected in the city of Puxinanã-PB, Brazil, registered in SisGen under the number: A35A42B. The compounds were identified by nuclear magnetic resonance and high-resolution mass spectrometry (HRMS).…”

Section: Isolation and Identification Of Lignansmentioning

confidence: 99%

Virtual Screening and the In Vitro Assessment of the Antileishmanial Activity of Lignans

Maia

Silva

Nunes³

et al. 2020

Molecules

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Leishmaniasis is endemic in at least 98 countries. Due to the high toxicity and resistance associated with the drugs, we chose lignans as an alternative, due to their favorable properties of absorption, distribution, metabolism, excretion, and toxicity (ADMET). To investigate their leishmanicidal potential, the biological activities of a set of 160 lignans were predicted using predictive models that were built using data for Leishmania major and L. (Viannia) braziliensis. A combined analysis, based on ligand and structure, and several other computational approaches were used. The results showed that the combined analysis was able to select 11 lignans with potential activity against L. major and 21 lignans against L. braziliensis, with multitargeting effects and low or no toxicity. Of these compounds, four were isolated from the species Justicia aequilabris (Nees) Lindau. All of the identified compounds were able to inhibit the growth of L. braziliensis promastigotes, with the most active compound, (159) epipinoresinol-4-O-β-d-glucopyranoside, presenting an IC50 value of 5.39 µM and IC50 value of 36.51 µM for L. major. Our findings indicated the potential of computer-aided drug design and development and demonstrated that lignans represent promising prototype compounds for the development of multitarget drugs against leishmaniasis.

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An Efficient Method for Determining the Relative Configuration of Furofuran Lignans by ¹H NMR Spectroscopy

Cited by 53 publications

References 37 publications

α-Glucosidic Hydroquinone Derivatives from Viburnum Erosum

α-Glucosidic Hydroquinone Derivatives from Viburnum Erosum

Three New Lignan Glycosides from the <i>Firmiana simplex</i>

Virtual Screening and the In Vitro Assessment of the Antileishmanial Activity of Lignans

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