Cytotoxic Phenylpropanoid Glycosides from the Stems of Smilax china

Kuo, Yao‐Haur; Hsu, Ya-Wen; Liaw, Chia‐Ching; Lee, Jiun Kuan; Huang, Hui‐Chi; Kuo, Li Jen

doi:10.1021/np050109q

Cited by 42 publications

(27 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…By using bioassay-guided fractionation together with repeated chromatographic and spectroscopic methods, 13 6.12) were in good accordance with three pairs of trans-olefinic protons in the R, -unsaturated carbonyl systems of the feruloyl units in 1. 14,15 The 1 H and 13 C NMR spectrum (Tables 1 and 2) of 1 showed an R-anomeric resonance at δ H 5.53 with a small coupling constant (d, J ) 3.6 Hz, H-1′) due to a gauche conformation, according to the Karplus relation, 16 together with 12 oxygenated carbon signals at δ C 62.4-105.8. These data implied that 1 is a disaccharide containing both a pentose and a hexose moiety.…”

Section: Resultsmentioning

confidence: 96%

Antioxidant and Anti-inflammatory Phenylpropanoid Derivatives from Calamus quiquesetinervius

et al. 2010

Self Cite

View full text Add to dashboard Cite

Eight new phenylpropanoid derivatives [quiquesetinerviusides A (1), B (2), C (3), D (4), and E (5), as well as quiquesetinerviusins A (6), B (7), and C (8)] and seven known compounds (8-15), were isolated from an EtOAc extract of Calamus quiquesetinervius stems. The structures of 1-8 were elucidated on the basis of 1D- and 2D-NMR spectroscopic data analysis. Bioassay results showed that 1-5 possess weak DPPH (2,2-diphenyl-1-picrylhydrazyl) scavenging activity, but potent (·)OH radical scavenging activity (IC(50) 3.6-8.4 μM). Of the tested isolates, compounds 4-6 and 9 showed potent inhibition (IC(50) 9.2-29.5 μM) of LPS-stimulated NO production when compared with a positive control substance, quercetin (IC(50) 34.5 μM).

show abstract

Section: Resultsmentioning

confidence: 96%

Antioxidant and Anti-inflammatory Phenylpropanoid Derivatives from Calamus quiquesetinervius

et al. 2010

Self Cite

View full text Add to dashboard Cite

show abstract

“…e; Table S4). These two metabolites were previously identified as smilaside A (3,6 diferuloyl‐3′,6′‐diacetylsucrose) in Smilax china (Kuo et al ., ) and smiglaside C (3,6 ‐ diferuloyl‐2′,3′,6′‐triacetylsucrose) in Smilax glabra (Chen et al ., ).…”

Section: Resultsmentioning

confidence: 99%

Ethylene signaling regulates natural variation in the abundance of antifungal acetylated diferuloylsucroses and Fusarium graminearum resistance in maize seedling roots

et al. 2018

View full text Add to dashboard Cite

Summary The production and regulation of defensive specialized metabolites play a central role in pathogen resistance in maize (Zea mays) and other plants. Therefore, identification of genes involved in plant specialized metabolism can contribute to improved disease resistance. We used comparative metabolomics to identify previously unknown antifungal metabolites in maize seedling roots, and investigated the genetic and physiological mechanisms underlying their natural variation using quantitative trait locus mapping and comparative transcriptomics approaches. Two maize metabolites, smilaside A (3,6‐diferuloyl‐3′,6′‐diacetylsucrose) and smiglaside C (3,6‐diferuloyl‐2′,3′,6′‐triacetylsucrose), were identified that could contribute to maize resistance against Fusarium graminearum and other fungal pathogens. Elevated expression of an ethylene signaling gene, ETHYLENE INSENSITIVE 2 (ZmEIN2), co‐segregated with a decreased smilaside A : smiglaside C ratio. Pharmacological and genetic manipulation of ethylene availability and sensitivity in vivo indicated that, whereas ethylene was required for the production of both metabolites, the smilaside A : smiglaside C ratio was negatively regulated by ethylene sensitivity. This ratio, rather than the absolute abundance of these two metabolites, was important for maize seedling root defense against F. graminearum. Ethylene signaling regulates the relative abundance of the two F. graminearum‐resistance‐related metabolites and affects resistance against F. graminearum in maize seedling roots.

show abstract

“…However, many Smilax species from other parts of the world such as Smilax china have been submitted to numerous chemical and biological studies due to their interesting properties. These species have been shown to contain steroidal saponins and phenolic compounds Sashida et al, 1992;Bernardo et al, 1996;Shu et al, 2002;Sautour et al, 2006;Xu et al, 2006) and have demonstrated interesting anti-inflammatory, anti-conceptive, cytotoxic, antioxidant, immunomodulatory, anticancer, hypoglycaemic, uricosuric and antifungal activities (Giachetti et al, 1988;Suh et al, 1996;Fukunaga et al, 1997;Lee et al, 2001;Jiang and Xu, 2003;Cox et al, 2005;Kuo et al, 2005;Sautour et al, 2005;Thabrew et al, 2005;Xu et al, 2005;Chu and Ng, 2006;Huang et al, 2006;Wang et al, 2006;Li et al, 2007).…”

Section: Introductionmentioning

confidence: 99%