Shizukaol a, a sesquiterpene dimer from Chloranthus japonicus

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

doi:10.1016/0031-9422(90)83065-9

Cited by 101 publications

(80 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Therefore, 1 appeared to be a lindenane dimer from the genus Chloranthus. The NMR data (Table 1) of 1 were quite similar to those of shizukaol F (5) [18], a significant difference was that 1 had a OH substituent at C(15) (d(C) 65.2), which could be confirmed by the HMBC correlations observed between HÀC(3), HÀC(4), HÀC(5), HÀC (15), and HÀC(9') ( Fig.). Thus, the structure of 1 was established as 15-hydroxyshizukaol F. The relative configuration of 1 was elucidated from ROESY correlations, including HÀC(1)/HÀC(3), HÀC(1)/H a ÀC(2), HÀC(1')/HÀC(3'), HÀC(1')/H a ÀC(2'), H a ÀC(2')/HÀC(3'), HÀC(1)/HÀC(9), HÀC(9)/HÀC(5'), which were a-oriented, so the 9-OH was b-oriented.…”

supporting

confidence: 69%

See 1 more Smart Citation

Sesquiterpenes and Dimers Thereof from Chloranthus fortunei

Wang

Ouyang

et al. 2009

Helvetica Chimica Acta

View full text Add to dashboard Cite

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.

show abstract

supporting

confidence: 69%

“…The other ROESY correlations of HÀC(6)/Me(13), HÀC(6)/Me (14), H b ÀC(6')/Me(14'), HÀC(9')/Me(14') were also observed. The ROESY interactions of HÀC (15)/H a ÀC(1') and H a ÀC(3')/CH 2 (15') suggested that HOÀC (15) and HOÀC(4') were both b-oriented. Hence, the structure of 1 was determined to be as shown and named shizukaol P.…”

mentioning

confidence: 95%

Sesquiterpenes and Dimers Thereof from Chloranthus fortunei

Wang

Ouyang

et al. 2009

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

“…Homodimeric terpenes as possible Diels-Alder cycloadducts. [78][79][80][81] stand in xylene at room temperature for 10 days, the cycloadducts 169 and 170 were obtained, not the natural product 167 (Scheme 35). On the other hand, when 171 was treated with acid, the product 167 was formed at room temperature within 30 minutes.…”

Section: Culantraraminementioning

confidence: 97%

“…A recent example of a Diels-Alder-cyclized quinone dimer is longithorone (163), isolated from a marine tunicate. [78] Other examples include shizukaol A (164), [79] cyclodione (165), [80] and maytenone (166; Scheme 34).…”

Section: Longithorone and Other Homodimer Terpenoidsmentioning

confidence: 99%

Chemistry and Biology of Biosynthetic Diels–Alder Reactions

2003

View full text Add to dashboard Cite

Nature's repertoire of biosynthetic transformations has recently been recognized to include the Diels-Alder cycloaddition reaction. Evidence now exists that there are enzymes that mediate the Diels-Alder reaction in secondary metabolic biosynthetic pathways. 2002 marked the 100th anniversary of Alder's birth and 75 years since the discovery of the Diels-Alder reaction. It would appear that living systems discovered and made use of this ubiquitously useful ring-forming reaction eons ago for the construction of complex natural products. In this Review an overview is given of all of the known classes of natural products (polyketides, isoprenoids, phenylpropanoids, alkaloids) that have been speculated to arise by a biological Diels-Alder reaction.

show abstract

“…Herein, we report the first phytochemical investigation of the roots of this plant. Three new sesquiterpenes and two new diterpenes, chloraniolide A (1), (3R)-3-hydroxyatractylenolide III (2), 8-hydroxy-1-oxoeudesma-3,7(11)-dien-12,8a-olide (3), (12R,13E)-15-(acetoxy)-12-hydroxylabda-8(20),13-dien-19-oic acid (4), and (12S,13E)-15-(acetoxy)-12-hydroxylabda-8(20),13-dien-19-oic acid (5), together with 17 known compounds, were isolated and identified. Their structures were elucidated by 1D-and 2D-NMR, and other spectroscopic analyses, as well as chemical conversions.…”

mentioning

confidence: 99%

Sesquiterpenoids and Diterpenoids from Chloranthus anhuiensis

Tang

Tan

et al. 2010

Chemistry & Biodiversity

View full text Add to dashboard Cite

A phytochemical investigation of the roots of Chloranthus anhuiensis afforded three new sesquiterpene lactones, chloraniolide A (1), (3R)-3-hydroxyatractylenolide III (2), and 8beta-hydroxy-1-oxoeudesma-3,7(11)-dien-12,8alpha-olide (3), and two new diterpenoids, (12R,13E)-15-(acetoxy)-12-hydroxylabda-8(20),13-dien-19-oic acid (4) and (12S,13E)-15-(acetoxy)-12-dihydroxylabda-8(20),13-dien-19-oic acid (5), as well as 17 known sesquiterpenoid and diterpenoid compounds. Their structures were established on the basis of 1D- and 2D-NMR, and other spectroscopic analyses.

show abstract

Shizukaol a, a sesquiterpene dimer from Chloranthus japonicus

Cited by 101 publications

References 8 publications

Sesquiterpenes and Dimers Thereof from Chloranthus fortunei

Sesquiterpenes and Dimers Thereof from Chloranthus fortunei

Chemistry and Biology of Biosynthetic Diels–Alder Reactions

Sesquiterpenoids and Diterpenoids from Chloranthus anhuiensis

Contact Info

Product

Resources

About