Eight new γ-lactam alkaloids from the roots of the Hemerocallis minor Mill

Zhao, Xincai; Xie, Yunying; Fan, Chun‐Lin; Huang, Yingying; Yan, Shaomin; Zhang, Yan; Jin, Hui‐Zi; Zhang, Guoqing

doi:10.1016/j.fitote.2017.03.001

Cited by 8 publications

(2 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Despite significant progress in discovering natural compounds from Styrax species and elucidating their potential pharmacological activities, there is still a need for a comprehensive and focused discussion of this rapidly growing research area. With our continuous interests in natural products discovery and pharmacological research [ 13 , 14 , 15 , 16 ], our aim is to provide researchers with a convenient and comprehensive resource that offers detailed and concise profiles of the Styrax genus. This review encompasses the examination of structural diversity and the pharmacological and biological significance and presents the exciting future research prospects in this field.…”

Section: Introductionmentioning

confidence: 99%

Chemical Constituents and Their Biological Activities from Genus Styrax

Xia

Han

et al. 2023

Pharmaceuticals

Self Cite

View full text Add to dashboard Cite

Plants from the genus Styrax have been extensively used in folk medicines to treat diseases such as skin diseases and peptic ulcers and as an antiseptic and analgesic. Most Styrax species, especially Styrax tonkinensis, which is used as an expectorant, antiseptic, and analgesic in Chinese traditional medicine, could screen resin after external injury. Styrax is also used in folk medicines in Korea to treat sore throat, bronchitis, cough, expectoration, paralysis, laryngitis, and inflammation. Different parts of various Styrax species can be widely employed for ethnopharmacological applications. Moreover, for ethnopharmacological use, these parts of Styrax species can be applied in combination with other folk medicines. Styrax species consist of versatile natural compounds, with some of them exhibiting particularly excellent pharmacological activities, such as cytotoxic, acetylcholinesterase inhibitory, antioxidant, and antifungal activities. Altogether, these exciting results indicate that a comprehensive review of plants belonging to this genus is essential for helping researchers to continuously conduct an in-depth investigation. In this review, the traditional uses, phytochemistry, corresponding pharmacological activities, and structure–activity relationships of different Styrax species are clarified and critically discussed. More insights into potential opportunities for future research are carefully assessed.

show abstract

Section: Introductionmentioning

confidence: 99%

Chemical Constituents and Their Biological Activities from Genus Styrax

Xia

Han

et al. 2023

Pharmaceuticals

Self Cite

View full text Add to dashboard Cite

show abstract

“…This makes them important building blocks in the total syntheses of alkaloids and their non-natural analogs [17][18][19][20][21]. However, the γ-lactam substructure itself is a central fragment of numerous bioactive alkaloids, such as pyrrocidine B (I) [22], fusarin C (II) [23], fusarisetin A (III) [24], pseurotin A (IV) [25], (−)-salinosporamide A (V) [26], parvistemoline (VI) [27], glochidine (VII) [28], and other alkaloids [29][30][31][32][33][34] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

α,γ-Dioxygenated amides via tandem Brook rearrangement/radical oxygenation reactions and their application to syntheses of γ-lactams

Klychnikov¹,

Pohl²,

Cı́sařová

et al. 2021

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

Pyrrolidones are common heterocyclic fragments in various biologically active compounds. Here, a two-step radical-based approach to γ-lactams bearing three to four stereocenters starting from epoxides, N-allylic silylacetamides and TEMPO is reported. The sequence starts with a new tandem nucleophilic substitution/Brook rearrangement/single electron transfer-induced radical oxygenation furnishing orthogonally protected α,γ-dioxygenated N-allylamides with wide scope, mostly good yields, and partly good diastereo- and enantioselectivity for defined combinations of chiral epoxides and chiral amides. This represents a very rare example of an oxidative geminal C–C/C–O difunctionalization next to carbonyl groups. The resulting dioxygenated allylic amides are subsequently subjected to persistent radical effect-based 5-exo-trig radical cyclization reactions providing functionalized pyrrolidones in high yields as diastereomeric mixtures. They converge to 3,4-trans-γ-lactams by base-mediated equilibration, which can be easily further diversified. Stereochemical models for both reaction types were developed.

show abstract

Fulvanines J−K, two rare lactam pyrrole alkaloids from Hemerocallis fulva

Lei,

Wang,

Yaermaimaiti

et al. 2024

Chemistry & Biodiversity

View full text Add to dashboard Cite

Two rare jatropham lactam derivatives, named as fulvanines J‐K (1‐2), together with six known pyrrole alkaloids, 5,5'‐oxydi(3‐methyl‐3‐pyrrolin‐2‐one) (3), (‐)‐5‐hydroxy‐3‐methyl‐3‐pyrrolin‐2‐one (jatropham) (4), (±)‐5‐O‐methyljatropham (5), perlolyrine (6), butyl‐2‐formyl‐5‐(hydroxymethyl)‐1H‐pyrrole‐1‐butanoate (7), and hemerocallisamine II (8), were isolated from the flower of Hemerocallis fulva. Their structures were elucidated on the basis of spectroscopic methods and compared with the NMR spectra data in the literature. All compounds were evaluated for their anti‐complementary activity in vitro, and compounds 1, 4, and 6 exhibited anti‐complement effect with CH50 values from 0.61 to 1.42 mM.

show abstract

Eight new γ-lactam alkaloids from the roots of the Hemerocallis minor Mill

Cited by 8 publications

References 23 publications

Chemical Constituents and Their Biological Activities from Genus Styrax

Chemical Constituents and Their Biological Activities from Genus Styrax

α,γ-Dioxygenated amides via tandem Brook rearrangement/radical oxygenation reactions and their application to syntheses of γ-lactams

Fulvanines J−K, two rare lactam pyrrole alkaloids from Hemerocallis fulva

Contact Info

Product

Resources

About