New dimeric phenanthrene and flavone from<i>Spiranthes sinensis</i>

Li, Congying; Liu, Jing; Su, Xue‐Hui; Yuan, Zhi‐Peng; Zhong, Yu‐Jiao; Li, Yanfang; Liang, Bing

doi:10.1080/10286020.2013.764868

Cited by 14 publications

(8 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Most of the dimers isolated from the family Orchidaceae are considered to be formed by the coupling of the commonly occurring monomers of Orchidaceae species, e.g., lusianthridin ( 172 , 175 , 176 , 179 , 181 , 190 , 196 – 199 ), ,,,,,, lusianthrin ( 198 , 199 , 212 ), coelonin ( 171 , 172 , 178 , 189 , 191 , 193 – 195 ), ,,, 6-methoxycoelonin ( 186 , 188 ), , flavanthrinin ( 191 , 192 , 206 – 208 ), ,, orchinol ( 182 ), nudol ( 186 , 196 , 197 , 205 , 209 , 210 ), ,,, and 2-hydroxy-4,7-dimethoxyphenathrene ( 187 – 190 , 193 – 195 , 209 , 211 ). ,, Monbarbatains B ( 198 ) and C ( 199 ) are both derived by the coupling of lusianthridin with lusianthrin and differ only in the positions of their linkages . In the case of compound 207 , the recently isolated aerosanthrene ( 89 ) serves as a monomer. , Symmetrical dimers can also be found among the isolated compounds of Orchidaceae species, for example, in a diphenanthrene ( 170 ) obtained from Bletilla yunnanensis , in which two O -methylorchinol monomers are linked at C-1 and C-1′ .…”

Section: Compound Structural Diversity and Biological Activitymentioning

confidence: 99%

See 1 more Smart Citation

Phenanthrenes: A Promising Group of Plant Secondary Metabolites

2017

View full text Add to dashboard Cite

Although phenanthrenes are considered to constitute a relatively small group of natural products, discovering new phenanthrene derivatives and evaluating their prospective biological activities have become of great interest to many research groups worldwide. Based on 160 references, this review covers the phytochemistry and pharmacology of 213 naturally occurring phenanthrenes that have been isolated between 2008 and 2016. More than 40% of the 450 currently known naturally occurring phenanthrenes were identified during this period. The family Orchidaceae is the most abundant source of these compounds, although several new plant families and genera have been involved in the search for phenanthrenes. The presence of certain substituent patterns may be restricted to specific families; vinyl-substituted phenanthrenes were reported only from Juncaceae plants, and prenylated derivatives occur mainly in Euphorbiaceae species. Therefore, these compounds also can serve as chemotaxonomic markers. Almost all of the newly isolated compounds have been studied for their biological activities (e.g., potential cytotoxic, antimicrobial, anti-inflammatory, and antioxidant effects), and many of them showed multiple activities. According to the accumulated data, denbinobin, with a novel mechanism of action, has great potential as a lead compound for the development of a new anticancer agent.

show abstract

Section: Compound Structural Diversity and Biological Activitymentioning

confidence: 99%

“…Homodimers of lusianthridin, named phochinenin G ( 176 ) and phoyunnanin C ( 181 ), have also been reported. , Monbarbatain A ( 212 ) is a 1,1′-linked dimer of lusianthrin and its unsaturated form, lusianthridin . Compound 182 is a symmetrical 3,3′-linked homodimer of orchinol …”

Section: Compound Structural Diversity and Biological Activitymentioning

confidence: 99%

Phenanthrenes: A Promising Group of Plant Secondary Metabolites

2017

View full text Add to dashboard Cite

show abstract

“…Column chromatography of the EtOAc fraction led to the isolation of five known and six novel dihydrophenanthrenes [10]. The traditional Chinese medicine 'Panlongshen' is derived from the dried root or the whole plant of S. sinensis, which is an Orchidaceae plant [15].…”

Section: Anti-hepatoma Cellmentioning

confidence: 99%

Pharmacological and Chemical Potential of Spiranthes sinensis (Orchidaceae): A Narrative Review

Kuo

Pei

Chao

2022

Plants

View full text Add to dashboard Cite

Orchidaceae is one of the largest families of flowering plants with more than 27,000 accepted species, and more than 31,000–35,000 species are estimated to exist in total. The orchid Spiranthes sinensis (Pers.) Ames, having ornamental and medicinal value, is widely distributed throughout Asia and Oceania. S. sinensis (Shou Tsao) is also known as Panlongshen among the common folk herbs. It has a fleshy root similar to ginseng, and the entire plant is widely used in traditional Chinese medicine. Owing to overexploitation and habitat destruction in recent years, the wild population has become scarce. The traits of this species show obvious differences in different countries. In the Taiwanese climate, it flowers during the Ching Ming Festival, also called the ching ming tsao. Previous investigations into S. sinensis have revealed the presence of flavonoids, homocyclotirucallane, dihydrophenanthrenes, ferulic acid, and 3,4-dihydroxybenzaldehyde. Phenolic constituents of structural and biological interest, including phenanthrenes and flavonoids, have been isolated and identified from S. sinensis. This natural product possesses extensive bioactivity, including anti-tumor, anti-inflammatory, and antioxidant effects. In this review, we outline the herbal medicine formulations and plant-derived natural products of S. sinensis.

show abstract

“…Therefore, isolation of anti-adipogenic compounds from medicinal plants can provide therapeutic and preventive strategies for the development of new applications. S. sinensis contains various types of bioactive compounds, such as phenanthrenes, flavonoids, coumarins, and steroids [ 13 , 14 , 15 , 16 ]. Among them, phenanthrene is the major chemical component [ 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Sinensol-C Isolated from Spiranthes sinensis Inhibits Adipogenesis in 3T3-L1 Cells through the Regulation of Adipogenic Transcription Factors and AMPK Activation

et al. 2020

View full text Add to dashboard Cite

Obesity is an abnormal medical condition caused by accumulation of body fat that presents negative health impacts. Adipocyte hyperplasia, also known as adipogenesis, is one of the major manifestations of obesity. In the present study, we isolated six phenanthrene derivatives (compounds 1–6) from the ethyl acetate fraction of Spiranthes sinensis and investigated their anti-adipogenic activity. We found that among the six phenanthrene derivatives, compound 6 (sinensol-C) exhibited strong inhibitory activity against intracellular lipid accumulation in 3T3-L1 adipocytes, with an IC50 value of 12.67 μM. Sinensol-C remarkably suppressed the accumulation of lipid droplets and adipogenesis, via down-regulation of adipogenic transcription factors, including peroxisome proliferator-activated receptor γ (PPARγ), CCAAT/enhancer binding protein α (C/EBPα), sterol regulatory element binding protein-1 (SREBP-1c), fatty acid synthase (FAS), and fatty acid binding protein 4 (FABP4), during adipocyte differentiation in 3T3-L1 cells. In addition, treatment with sinensol-C significantly increased the adenosine monophosphate-activated protein kinase (AMPK) activity in 3T3-L1 cells. Taken together, these data strongly suggest that sinensol-C regulates adiogenesis via down-regulation of adipogenic transcription factors and up-regulation of AMPK. Furthermore, this is the first study that demonstrates that sinensol-C has the capacity to modulate adipogenesis.

show abstract

New dimeric phenanthrene and flavone fromSpiranthes sinensis

Cited by 14 publications

References 10 publications

Phenanthrenes: A Promising Group of Plant Secondary Metabolites

Phenanthrenes: A Promising Group of Plant Secondary Metabolites

Pharmacological and Chemical Potential of Spiranthes sinensis (Orchidaceae): A Narrative Review

Sinensol-C Isolated from Spiranthes sinensis Inhibits Adipogenesis in 3T3-L1 Cells through the Regulation of Adipogenic Transcription Factors and AMPK Activation

Contact Info

Product

Resources

About