Polyoxygenated Cyclohexene Derivatives fromUvaria rufa

Zhang, Chuan‐Rui; Yang, S.‐L.; Liao, Shang‐Gao; Wu, Yan; Yue, Jian‐Min

doi:10.1002/hlca.200690140

Cited by 33 publications

(19 citation statements)

References 16 publications

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“…3) exhibited a negative cotton effect at 230 nm (De 230 À1.37) due to exciton coupling ( Fig. 2) between the benzoyl group at C-3 and the nearby C¼C bond (allylic benzoate) (Harada et al, 1981;Zhang et al, 2006). Thus, the absolute configuration of Dulcisene A (1) was identified as 1R,2S,3R,6R.…”

Section: Resultsmentioning

confidence: 92%

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Cyclohexene long-chain fatty acid esters from Uvaria dulcis (Dunal)

Kaweetripob

Mahidol

Prawat

et al. 2015

Phytochemistry Letters

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Section: Resultsmentioning

confidence: 92%

“…The isolation of (-À)-zeylenol derivatives from U. dulcis in present study could serve as a chemotaxonomic marker for Uvaria genus (Jolad et al, 1981;Pan et al, 1996;Zhang et al, 2006).…”

Section: Discussionmentioning

confidence: 93%

Cyclohexene long-chain fatty acid esters from Uvaria dulcis (Dunal)

Kaweetripob

Mahidol

Prawat

et al. 2015

Phytochemistry Letters

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“…The relative configuration of 3 was assigned on the basis of the NOESY correlations and the coupling constant data. The NOESY correlations between H-2/H-3 and H-3/H-4 ( Figure 2b) and the coupling constants J 2,3 = 3.7 Hz and J 3,4 = 1.8 Hz (Table 2) 21,22 suggesting the spatial orientation of two benzoates at C-3 and C-7 to be in a counterclockwise fashion. 22 Therefore, the absolute configuration of uvaridacol A (3) was proposed as 2S, 3R, 4R, and 5R.…”

Section: ■ Results and Discussonmentioning

confidence: 93%

“…Uvaridacol D (7) displayed a negative Cotton effect Figure S16), attributable to exciton coupling between the benzoyl group at C-4 and the allylic benzoate. 21 Thus, the absolute configuration of 7 was concluded to be 2S, 3S, 4R, and 5R. Grandifloracin (8) was isolated as a white, amorphous solid.…”

Section: ■ Results and Discussonmentioning

confidence: 99%

Antiausterity Agents from Uvaria dac and Their Preferential Cytotoxic Activity against Human Pancreatic Cancer Cell Lines in a Nutrient-Deprived Condition

et al. 2012

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Human pancreatic cancer cell lines are known for their inherent tolerance to nutrition starvation, which enables them to survive under a hypovascular (austerity) tumor microenvironment. The search for agents that preferentially retard the survival of cancer cells under low nutrition conditions (antiausterity agent) is a novel approach to anticancer drug discovery. In this study, it was found that a dichloromethane extract of the stem of Uvaria dac preferentially inhibited PANC-1 human pancreatic cancer cells survival under nutrition-deprived conditions at a concentration of 10 μg/mL. Workup of this bioactive extract led to the discovery of (+)-grandifloracin (8) as a potent antiausterity agent as evaluated in a panel of four human pancreatic cancer cell lines, PANC-1 (PC(50), 14.5 μM), PSN-1 (PC(50), 32.6 μM), MIA PaCa-2 (PC(50), 17.5 μM), and KLM-1 (32.7 μM). (+)-Grandifloracin (8) has been isolated from a natural source for the first time. Its absolute stereochemistry was established by single-crystal X-ray crystallography and circular dichroism spectroscopic analysis. In addition to this, seven other new highly oxygenated cyclohexene derivatives, named uvaridacanes A (1) and B (2), uvaridacols A-D (3, 4, 6, 7), and uvaridapoxide A (5), were also isolated and structurally characterized.

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“…Among them, approximately 60 were new compounds, and 6 had new carbon skeletons ( Figure 6). In particular, 48 of these compounds showed significant biological activities in a variety of bioassays and provided a scientific foundation for the use of a number of traditional Chinese herbs [103][104][105][106][107][108][109][110][111][112][113][114] .…”

Section: Miscellaneousmentioning

confidence: 99%

Discovery of structurally diverse and bioactive compounds from plant resources in China

Shi

Yue

2012

Acta Pharmacol Sin

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This review describes the major discoveries of structurally diverse and/or biologically significant compounds from plant resources in China, mainly from the traditional Chinese medicines (TCMs) since the establishment of our research group in 1999. In the past decade, a large array of biologically significant and novel structures has been identified from plant resources (or TCM) in our laboratory. The structural modification of several biologically important compounds led to more than 400 derivatives, some of which exhibited significantly improved activities and provided opportunities to elucidate the structure-activity relationship of the related compound class. These findings are important for drug discovery and help us understand the biological basis for the traditional applications of these plants in TCM.

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Polyoxygenated Cyclohexene Derivatives fromUvaria rufa

Cited by 33 publications

References 16 publications

Cyclohexene long-chain fatty acid esters from Uvaria dulcis (Dunal)

Cyclohexene long-chain fatty acid esters from Uvaria dulcis (Dunal)

Antiausterity Agents from Uvaria dac and Their Preferential Cytotoxic Activity against Human Pancreatic Cancer Cell Lines in a Nutrient-Deprived Condition

Discovery of structurally diverse and bioactive compounds from plant resources in China

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