Dictamnol, a New Trinor-Guaiane Type Sesquiterpene, from the Roots of Dictamnus dasycarpus Turcz.

Takeuchi, Naoki; Fujita, Takashi; Goto, Kaori; Morisaki, Naomi; Osone, Naoko; Tobinaga, Seisho

doi:10.1248/cpb.41.923

Cited by 36 publications

(24 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…(Rutaceae) is used in Chinese traditional medicine for the treatment of various ailments, such as jaundice, cough, eczema, rubella, scabies, some skin disease, and rheumatism (Lei et al, 2008). There have been chemical studies of the D. dasycarpus such as limonoids (Hu et al, 1989;Wang et al, 1992), furoquinoline alkaloids (Storer and Young, 1972), flavonoids (Souleles, 1989a(Souleles, , 1989b, coumarins (Reisch et al, 1967), sesquiterpene (Takeuchi et al, 1993), and sesquiterpene glycosides (Zhao et al, 1998(Zhao et al, , 1999. Among them, the alkoloids and limonoids were the major bioactive compounds (Yu et al, 1992;Jung et al, 2000).…”

Section: Introductionmentioning

confidence: 99%

Neuroprotective effects of constituents of the root bark of Dictamnus dasycarpus in mouse hippocampal cells

Jeong

Byun

et al. 2010

Arch. Pharm. Res.

View full text Add to dashboard Cite

Glutamate-induced oxidative injury causes neuronal degeneration related to many central nervous system diseases, such as Parkinson's disease, Alzheimer's disease, epilepsy and ischemia. The bioassay-guided fractionation of the EtOH extract of the root bark of Dictamnus dasycarpus Trucz. provided one neuroprotective limonoid, obacunone, together with a degraded limonoid, fraxinellone and two alkaloids, dictamine and haplopine. At concentrations of 100-150 microM, obacunone showed the potent neuroprotective effects on glutamateinduced neurotoxicity and induced the expression of heme oxygenase (HO)-1 in the mouse hippocampal HT22 cells. In addition, we found that obacunone increased p38 MAPK phosphorylation and induced HO-1 expression via p38 MAPK pathway. These results suggest that obacunone isolated from the root bark of D. dasycarpus increases cellular resistance to glutamate-induced oxidative injury in mouse hippocampal HT22 cells, presumably through the p38 MAPK pathway-dependent HO-1 expression. These results suggest that obacunone could be the effective candidates for the treatment of ROS-related neurological diseases.

show abstract

Section: Introductionmentioning

confidence: 99%

Neuroprotective effects of constituents of the root bark of Dictamnus dasycarpus in mouse hippocampal cells

Jeong

Byun

et al. 2010

Arch. Pharm. Res.

View full text Add to dashboard Cite

show abstract

“…[160] However, a structural reassignment that involves a much smaller alteration to the molecular architecture can throw a synthetic approach into a similar degree of disarray. [165][166][167] Similarly, in an age driven by the use of asymmetric reactions to establish stereocenters, a stereochemical error in another part of the molecule could have an impact on the strategy/catalyst design. In 1975, the research group of Nakanishi correctly determined most of its architecture based exclusively on spectroscopic methods and proposed structure 53 (Figure 7).…”

Section: Methodsmentioning

confidence: 99%

Chasing Molecules That Were Never There: Misassigned Natural Products and the Role of Chemical Synthesis in Modern Structure Elucidation

2005

View full text Add to dashboard Cite

Over the course of the past half century, the structural elucidation of unknown natural products has undergone a tremendous revolution. Before World War II, a chemist would have relied almost exclusively on the art of chemical synthesis, primarily in the form of degradation and derivatization reactions, to develop and test structural hypotheses in a process that often took years to complete when grams of material were available. Today, a battery of advanced spectroscopic methods, such as multidimensional NMR spectroscopy and high-resolution mass spectrometry, not to mention X-ray crystallography, exist for the expeditious assignment of structures to highly complex molecules isolated from nature in milligram or sub-milligram quantities. In fact, it could be argued that the characterization of natural products has become a routine task, one which no longer even requires a reaction flask! This Review makes the case that imaginative detective work and chemical synthesis still have important roles to play in the process of solving nature's most intriguing molecular puzzles.

show abstract

“…(Rutaceae) is used in Chinese folk medicine for the treatment of jaundice, cough, rheumatism and some skin diseases, and its water extract was reported to inhibit the growth of many kinds of human pathogenic fungi in vitro [1]. Several kinds of compounds including limonoids [2], [3], furoquinoline alkaloids [4], flavonoids [5], [6], coumarins [7], sesquiterpene [8], and sesquiterpene glycosides [9], [10] have been isolated from D. dasycarpus. Zhao et al [11] reported six compounds inhibitory to the plant pathogenic fungus Cladosporium cucumerinum from the dichloromethane extract of D. dasycarpus.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Terpenoid and Immunosuppressive Phenolic Glycosides from the Root Bark of Dictamnus dasycarpus

Chang

Liu

et al. 2002

Planta med

View full text Add to dashboard Cite

Five new compounds, two degraded terpene glycosides, dasycarpusides A and B (1, 2), and three phenolic glycosides, 2-methoxy-4-hydroxymethylphenol 1-O-alpha-rhamnopyranosyl-(1"-->6')- beta-glucopyranoside ( 3), 2-methoxy-4-acetylphenol 1-O-alpha-rhamnopyranosyl-(1"-->6')-beta-glucopyranoside (4), and 2-methoxy-4-(8-hydroxyethyl)-phenol 1-O-alpha-rhamnopyranosyl-(1"-->6')-beta-glucopyranoside (5), were isolated from the water-soluble constituents of the root bark of Dictamnus dasycarpus Turcz.(Rutaceae). Their structures were elucidated by spectroscopic analysis and chemical evidence. Moreover, it was found that dasycarpuside A (1) showed weak cytotoxic activity against A-549 (human lung adenocarcinoma) cell line, while 4 and 5 showed more remarkable activity of inhibiting the proliferation of T-cells in vitro.

show abstract

Dictamnol, a New Trinor-Guaiane Type Sesquiterpene, from the Roots of Dictamnus dasycarpus Turcz.

Cited by 36 publications

References 0 publications

Neuroprotective effects of constituents of the root bark of Dictamnus dasycarpus in mouse hippocampal cells

Neuroprotective effects of constituents of the root bark of Dictamnus dasycarpus in mouse hippocampal cells

Chasing Molecules That Were Never There: Misassigned Natural Products and the Role of Chemical Synthesis in Modern Structure Elucidation

Cytotoxic Terpenoid and Immunosuppressive Phenolic Glycosides from the Root Bark of Dictamnus dasycarpus

Contact Info

Product

Resources

About