Isolation and Structural Elucidation of Four Sesquiterpenes from<i>Chloranthus japonicus</i>(Chloranthaceae)

Kawabata, Jun; Tahara, Satoshi; Mizutani, Junya

doi:10.1080/00021369.1981.10864706

Cited by 27 publications

(57 citation statements)

References 13 publications

(25 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Although various sesquiterpenoids 12,13) and sesquiterpenoid oligomers 14,15) isolated from C. japonicus have biological activities such as cell adhesion inhibition 10) and growth inhibition against Mucor and Rhizopus, 25) this is the first report that a novel sesquiterpene furan compound CJ-01 specifically inhibited the chitin synthase 2 of S. cerevisiae. Therefore, the compound CJ-01 may be a novel lead compound for the development of antifungal agent through the control of chitin synthesis.…”

Section: Resultsmentioning

confidence: 99%

Sesquiterpene Furan Compound CJ-01, a Novel Chitin Synthase 2 Inhibitor from Chloranthus japonicus SIEB.

Yim

Hwang

Yun

et al. 2008

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

Fungal cell walls have essential roles in the life of the fungal cell. They protect mechanically the cell from the environment, prevent osmotic bursting of the cell by the tugor pressure and act as a sieve for large molecules that might harm the cell membrane. 1)Chitin, along with (1,3)-b-D-glucan, represents the main structural components of the fungal cell wall. As a crystalline polymer composed of b-1,4-linked homopolymer of N-acetylglucosamine (GlcNAc), chitin contributes to the rigidity of the cell wall.2) It is synthesized on the cytoplasmic surface of the plasma membrane, extruded perpendicularly to the cell surface as microfibrils and crystallized outside the cell through extensive hydrogen bonding as a-chitin (the polyGlcNAc chains run antiparallel).3) Chitin is synthesized by chitin synthase 1 (ScCHS1p), 2 (ScCHS2p), and 3 (ScCHS3p) in Saccharomyces cerevisiae. 4,5) Among them, chitin synthase 1 is a nonessential repair enzyme, 5) whereas chitin synthase 2 and 3 are essential enzymes in primary septum formation 6) and bud ring formation, 7) respectively. Although the content of chitin in the fungal cell wall varies from species to species, 8) its synthesis constitutes a model for fungal morphogenesis. Thus, specific inhibitors of chitin synthase 2 and 3 might serve as interesting lead compounds for the development of effective antifungal agents.The Chloranthus japonicus (Chloranthaceae) is a perennial herb that grows in the southern part of Korea, Japan, and China. This plant has been long recognized to be useful for boils, dermatopathy, and enteric fever in Korea as a folk remedy.9) Recently, shizukaol B, cycloshizukaol A, and shizukaol F isolated from the roots of Chloranthus japonicus were reported as cell adhesion inhibitors.10) In addition, many plants of the genus Chloranthus have been used in Chinese folk medicine for the treatment of bone fractures.11) A number of sesquiterpenoids 12,13) and sesquiterpenoid oligomers 14,15) have been isolated from the genus Chloranthus, and a quite recent study showed that chlorahololides A and B isolated from Chloranthus holostegius were potent and selective blockers of potassium channel. 16)In the course of search for chitin synthase 2 inhibitors from plant extracts, a novel type of chitin synthase 2 inhibitor was found in the methanol extract of the whole bodies of C. japonicus Sieb. Although the extract of C. japonicus has been long recognized to be useful as a folk remedy in Korea,9) this is the first report that the extract of C. japonicus could be used as antifungal agents by the inhibition of chitin synthase 2. Here, we describe the isolation and structure elucidation of a novel sesquiterpene furan compound CJ-01, and its inhibitory activities against chitin synthase 2 of S. cerevisiae and various human and phytopathogenic fungi. A novel sesquiterpene furan compound CJ-01 was isolated from the methanol extract of the whole plant of Chloranthus japonicus SIEB. by monitoring the inhibitory activity of chitin synthase 2 from Saccharomyces cerevisiae. Based...

show abstract

Section: Resultsmentioning

confidence: 99%

Sesquiterpene Furan Compound CJ-01, a Novel Chitin Synthase 2 Inhibitor from Chloranthus japonicus SIEB.

Yim

Hwang

Yun

et al. 2008

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

show abstract

“…Sesquiterpenoids including ␤-elemene, curcumol, germacrone, curdione and neocurdione are found to be the biological active ingredients in the essential oil [6,7]. Therefore, quantiment takes place in the injector and column [13][14][15]. Therefore, optimization of GC-MS conditions for analysis of volatile oil should be based on the resolution and stability of analytes while their chemical properties were unknown.…”

Section: Introductionmentioning

confidence: 99%

Optimization of GC–MS conditions based on resolution and stability of analytes for simultaneous determination of nine sesquiterpenoids in three species of Curcuma rhizomes

Yang

Zhao

et al. 2007

Journal of Pharmaceutical and Biomedical Analysis

View full text Add to dashboard Cite

“…Some 1 H-NMR and 13C-NMR spectra were obtained on a JEOL FX-200 instrument. (2) and Juranodienone (5). Fresh roots (3.5 kg) of C. japonicus collected at Mt.…”

Section: Methodsmentioning

confidence: 99%

Structures of Novel Sesquiterpene Alcohols fromChloranthus japonicus(Chloranthaceae)

Kawabata

Fukushi

Tahara

et al. 1984

Agricultural and Biological Chemistry

Self Cite

View full text Add to dashboard Cite

Isolation and Structural Elucidation of Four Sesquiterpenes fromChloranthus japonicus(Chloranthaceae)

Cited by 27 publications

References 13 publications

Sesquiterpene Furan Compound CJ-01, a Novel Chitin Synthase 2 Inhibitor from Chloranthus japonicus SIEB.

Sesquiterpene Furan Compound CJ-01, a Novel Chitin Synthase 2 Inhibitor from Chloranthus japonicus SIEB.

Optimization of GC–MS conditions based on resolution and stability of analytes for simultaneous determination of nine sesquiterpenoids in three species of Curcuma rhizomes

Structures of Novel Sesquiterpene Alcohols fromChloranthus japonicus(Chloranthaceae)

Contact Info

Product

Resources

About