Structures of Novel Sesquiterpene Ketones from<i>Chloranthus serratus</i>(Chloranthaceae)

Kawabata, Jun; Fukushi, Yukiharu; Tahara, Satoshi; Mizutani, Junya

doi:10.1080/00021369.1985.10866891

Cited by 11 publications

(13 citation statements)

References 14 publications

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“…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%

“…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.…”

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

Yim

Hwang

Yun

et al. 2008

Biological & Pharmaceutical Bulletin

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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...

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Section: Resultsmentioning

confidence: 99%

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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

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“…Four of them were new compounds, including one new sesquiterpene dimer, i.e., shizukaol P (1), one new dimeric sesquiterpene glycoside, i.e., 9-O-b-glucopyranosylcycloshizukaol A (2), and two new sesquiterpenes, i.e., shizukanolides G and H (3 and 4, resp.). The other eight known compounds were identified as shizukaol F (5) [18], yinxiancaol (6) [14], chloramultilide B (7) [22], cycloshizukaol A (8) [17], chloranthalactone C (9) [4][9], shizukanolide C (10) [4], shizukanolide F (11) [7], and chloranoside A (12) [10]. Their structures and relative configurations were elucidated on the basis of their spectroscopic data and by comparing with the related compounds reported in the literature.…”

Section: Sesquiterpenes and Dimers Thereof From Chloranthus Fortuneimentioning

confidence: 99%

Sesquiterpenes and Dimers Thereof from Chloranthus fortunei

Wang

Ouyang

et al. 2009

Helvetica Chimica Acta

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Four new compounds, including one new sesquiterpene dimer, i.e., shizukaol P (1), one new dimeric sesquiterpene glycoside, i.e., 9-O-b-glucopyranosylcycloshizukaol A (2), and two new sesquiterpenes, i.e., shizukanolides G and H (3 and 4, resp.), together with eight known compounds, were isolated from the aerial part of Chloranthus fortunei. The structures and relative configurations were elucidated on the basis of spectroscopic data and by comparison with those of the related compounds reported in the literature.Introduction. [25]. Chloranthus fortunei (A. Gray) Solms-Laub has been used in Chinese folk medicine for the treatment of bone fractures [26]. During our ongoing search for biologically active substances from this plant, 13 compounds have been isolated from the aerial part of it. Four of them were new compounds, including one new sesquiterpene dimer, i.e., shizukaol P (1), one new dimeric sesquiterpene glycoside, i.e., 9-O-b-glucopyranosylcycloshizukaol A (2), and two new sesquiterpenes, i.e., shizukanolides G and H (3 and 4, resp.). The other eight known compounds were identified as shizukaol F (5) [7], and chloranoside A (12) [10]. Their structures and relative configurations were elucidated on the basis of their spectroscopic data and by comparing with the related compounds reported in the literature.

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“…1,2 The plant is grown in Vietnam to produce flowers for scenting tea. 1,2 Earlier investigations concerned the sesquiterpene constituents of C. serratus, [3][4][5] C. glaber 6,7 and C. japonicus [8][9][10][11][12][13][14] and the constituents of the volatiles of flowers of C. spicatus growing in China. 15,16 We now report on the constituents of the flower essential oil of C. spicatus of Vietnamese origin.…”

Section: Introductionmentioning

confidence: 99%

Composition of the essential oil of flowers ofChloranthus spicatus (Thunb.) Makino

et al. 2006

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The composition of the essential oil of the flowers of Chloranthus spicatus (Thunb.) Makino (Chloranthaceae) was investigated using capillary GC-GC/MS, preparative GC and NMR techniques. Forty-seven compounds were identified either by comparing their retention indices and mass spectra with a library of authentic samples established under identical experimental conditions or, by isolating the compounds and deriving their structures by one-and two-dimensional NMR investigations. Thus, four minor components, viz. chloranthalactone A (0.5%), isogermafurenolide (0.7%), eudesma-4(15),7(11),9-trien-12-olide (0.5%), and 7α α α α α-hydroxyeudesm-4-en-6-one (3.3%), were isolated for the first time as constituents of the essential oil of the flowers of C. spicatus and their structures established. The major components of the oil include (Z)-β β β β β-ocimene (6.3%), allo-aromadendrene (6.2%), sarisane (2-allyl-4,5-methylenedioxyanisol, 4.2%) and selina-4(15),7(11)-diene (6.4%).

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Structures of Novel Sesquiterpene Ketones fromChloranthus serratus(Chloranthaceae)

Cited by 11 publications

References 14 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.

Sesquiterpenes and Dimers Thereof from Chloranthus fortunei

Composition of the essential oil of flowers ofChloranthus spicatus (Thunb.) Makino

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