Oldhamiphylline A: a Novel Hexacyclic Alkaloid from <i>Daphniphyllum oldhami</i>

Chen, Xin; Zhan, Zha‐Jun; Yue, Jian‐Min

doi:10.1002/cbdv.200490111

Cited by 25 publications

(17 citation statements)

References 25 publications

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“…Since we published the first chemical studies on D subverticillatum in 2003, a total of 194 structurally complex alkaloids have been isolated from 9 species of Daphniphyllum in our research group, 72 of which were novel structures. Among the novel compounds, 14 of them had new skeletons or possessed rearranged carbon frameworks [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] . Some alkaloids showed strong cytotoxic activity [16] .…”

Section: Structurally Diverse and Novel Alkaloidsmentioning

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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Section: Structurally Diverse and Novel Alkaloidsmentioning

confidence: 99%

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

Shi

Yue

2012

Acta Pharmacol Sin

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“…Na 2 CO 3 soln., and then extracted with CHCl 3 to obtain crude alkaloids (8.0 g). The crude alkaloids were subjected to CC (SiO 2 ; CHCl 3 Daphnilongertone (= (4S*,4aR*,8R*,8aR*,11aR*,11bR*)- 1,2,3,4,4a,5,8,8a,9,11a-Decahydro-11a-hydroxy-2-methyl-4a-(4-methyl-3-oxopentyl)-7H-4,11-ethano-8,11b-methanocyclopenta [5,6]oxocino [4,3- 13 C-, and 2D-NMR: see Table 1 3,4,5,5',6,6',7,8,8a,9,10-Dode-A C H T U N G T R E N N U N G cahydro-6,6'-dihydroxy-2-methyl-6'-(1-methylethyl)-1H,4'H-spiro [4,10a-methanopentaleno [1,6-cd] …”

Section: D(h) D(c)mentioning

confidence: 99%

“…Since the 9-OH function had to be on the opposite side of the seven-membered lactone ring, it was a-oriented. From these data, the structure of daphnilongertone (1) was identified as (4S*,4aR*,8R*,8aR*,11-aR*,11bR*)-1,2,3,4,4a,5,8,8a,9,11a-decahydro-11a-hydroxy-2-methyl-4a-(4-methyl-3oxopentyl)-7H-4,11-ethano-8,11b-methanocyclopenta [5,6]oxocino [4,3-c]pyridin-7one.…”

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confidence: 95%

New Alkaloids fromDaphniphyllum longeracemosumRosenth.

et al. 2006

HCA

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“…It has been shown to be an anthocyanin-rich, biofunctional food that contains various alkaloid compounds. [8][9][10][11][12][13] Its leaf and stalk have been traditionally used in China and Korea as a crude drug for treating wet pleurisy and peritonitis, and also as a diuretic. However, few reports have described the biological activities of D. macropodum, and in particular, none have described any antidiabetic effects.…”

Section: Introductionmentioning

confidence: 99%

Anti-diabetic properties ofDaphniphyllum macropodumfruit and its active compound

Koo

Kwak

Kang

2014

Bioscience, Biotechnology, and Biochemistry

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We evaluated in vitro anti-diabetic activities of 497 native plants of Jeju Island (South Korea) by measuring the induction of adipocyte differentiation. Among the plants, Daphniphyllum macropodum fruit extract (DME) had the highest peroxisome proliferatoractivated receptor γ (PPARγ) agonist activity and was therefore selected as a potential source of antidiabetic agents. To elucidate the active components of DME, constituent compounds were purified and their effects on the adipocyte differentiation were studied. Using activity-guided fractionation, four compounds were isolated from DME and their adipogenic effects were evaluated. Among the compounds isolated, 5,7-dihydroxychromone potently induced the differentiation of mouse 3T3-L1 preadipocytes. DME and 5,7-dihydroxychromone increased PPARγ and liver X receptor α (LXRα) mRNA expression levels. To determine whether the adipogenic effects we observed might affect serum glucose levels, we undertook in vivo experiment using streptozotocin-/high-fat diet-induced type 2 diabetes mouse model. DME supplementation reduced serum glucose, total cholesterol, and triacylglycerol levels in diabetes mice. These results suggest that DME may be useful for the prevention and treatment of type 2 diabetes mellitus. Moreover, it was proposed that 5,7-dihydroxychromone isolated from DME is one of the active compounds that may contribute to regulate blood glucose levels.

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Oldhamiphylline A: a Novel Hexacyclic Alkaloid from Daphniphyllum oldhami

Cited by 25 publications

References 25 publications

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

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

New Alkaloids fromDaphniphyllum longeracemosumRosenth.

Anti-diabetic properties ofDaphniphyllum macropodumfruit and its active compound

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