Volatile Components of "San-shion"

Mitsuyo, Okazaki; Ishizaki, Yoshihiro; Tanahashi, Yoshiaki; Harada, Hiroshi; Takahashi, Takeyoshi

doi:10.1248/yakushi1947.94.7_881

Cited by 9 publications

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“…Its absolute configuration was resolved by the chemical correlation through its hydrogenation product that was identical to a material derived from 129 by dehydration with POCl 3 and hydrogenation [352, 353] . The (−)‐enantiomer of 138 was later isolated from several other plants [177, 349, 354–367] . Full 1 H‐ and 13 C‐NMR data in CDCl 3 and C 6 D 6 have been reported [367, 368] …”

Section: Cyclised and Rearranged Guaianesmentioning

confidence: 96%

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Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Dickschat

2020

Chemistry A European J

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This review summarises known sesquiterpenes whose biosyntheses proceed through the intermediate germacrene A. First, the occurrencea nd biosynthesis of germacrene Ai nN ature and its peculiar chemistry will be highlighted , followed by ad iscussion of 6-6 and 5-7 bicyclic compounds and their more complex derivatives. For each compound the absolutec onfiguration, if it is known,a nd the reasoning for its assignment is presented. 2. Germacrene A 2.1. Occurrence in Nature (À)-Germacrene A(1,S cheme 2) was first isolated in 1970 from the gorgonian Eunicea mammosa. [7] Its absolute configuration was established as (S)-(À)-1 through its Cope rearrangement to (+ +)-b-elemene (2)f or which the configurational assignment was performed by chemical correlation of (À)-elemol(3)t o (À)-2. [8, 9] Compound (À)-1 is also believed to occur in the soft coral Lobophytum, [10] andi st he alarm pheromone of the aphid Terioaphis maculata. [11, 12] In the course of this work it was noticed that the optical rotation([ a] D 25 = À26.8, c 1.0, CCl 4)w as significantly highert han initially reported ([a] D 25 = À3.2, c 14.4, CCl 4), [7] which is explainableb yapartial rearrangement of purified (À)-1 to (+ +)-2,o ra lternatively, 1 isolated from E. mammosa was not enantiomerically pure. However,the opticalrotation of (+ +)-2 ([a] D 25 =+15.1, neat) reported in this initial study [7] matches the reported value for (À)-2 ([a] D 25 = À15.8, c 0.50, CHCl 3)o btainedb yC ope rearrangement of (+ +)-1, [13] thus disfa-Scheme1.Te rpene cyclisation modes for FPP. Scheme2.Structure of 1 and its absolute configurationbyc hemicalcorrelation.

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Section: Cyclised and Rearranged Guaianesmentioning

confidence: 96%

“…[352,353] The (À)enantiomer of 138 was later isolated from several other plants. [177,349,[354][355][356][357][358][359][360][361][362][363][364][365][366][367] Full 1 H-and 13 C-NMRd ata in CDCl 3 and C 6 D 6 have been reported. [367,368]…”

Section: Compounds From J3mentioning

confidence: 98%

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Dickschat

2020

Chemistry A European J

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“…(Asteraceae) in China is a highly diversified genus, with a rich chemical biodiversity. In addition, some Ligularia species are known to exhibit biological activities [1] [2]. L. latihastata (W. W. Smith) Hand.-Mazz.…”

Section: Chemical and Genetic Diversity Of Ligularia Latihastata And mentioning

confidence: 99%

“…Another aim was to examine the relation of L. latihastata to a San-shion sample studied some 30 years ago. One of us (H. H.) and co-workers had previously isolated several guaiane sesquiterpenes such as 5,11-expoxyguaiane from the dried roots of a putative Sanshion sample imported from China to Japan as a herbal medicine [2] [11]. However, the identity of the plant had been unknown at that time, because the material consisted solely of roots.…”

Section: Chemical and Genetic Diversity Of Ligularia Latihastata And mentioning

confidence: 99%

Chemical and Genetic Diversity of Ligularia latihastata and Ligularia villosa in Yunnan Province of China

Kuroda

Kiuchi

Torihata

et al. 2007

Chemistry & Biodiversity

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The chemical constituents of the root extracts and the nucleotide sequences of the atpB-rbcL intergenic region of Ligularia latihastata and L. villosa, collected in northwestern Yunnan Province, were studied. In the twelve collected samples of L. latihastata, two major benzofurans, 5,6-dimethoxy-2-(1-methylethenyl)-1-benzofuran (1) and euparin (2) were detected as major components. The minor compound (2R*,3S*)-5-acetyl-2,3-dihydro-6-hydroxy-2-(1-methylethenyl)-1-benzofuran-3-yl (2Z)-2-[(acetoxy)methyl]but-2-enoate (4) was found to be susceptible to artifact formation upon extraction with EtOH. The intra-specific diversity in chemical composition of the samples was small, but the diversity in the atpB-rbcL sequence was fairly large. Compounds 1 and 2 were also found in the three collected samples of L. villosa, indicating that the two species are chemically close to each other, in agreement with morphological taxonomy.

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“…The guaiane type oxide, LB (139) was isolated (it was also detected in sample 9). [18][19][20][21] LB (139) was first isolated from the Chinese drug 'San Sion,' imported from China, purchased through the Oriental drug store, the original plant of which was unclear at that time. Since then LB has not been isolated; at least no report has been found.…”

Section: )mentioning

confidence: 99%

Terpenoid Composition and Base Sequences of <i>Ligularia virgaurea</i> (Asteraceae) Grown in the Hengduan Mountain Area in China and a Comment on Drawing Structures

Tori

2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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A chemical analysis of 30 samples of Ligularia virgaurea (Asteraceae) collected in Sichuan province and its adjacent territories in China was reviewed. These samples afforded 146 compounds, 73 of which were novel, and the chemical constituents were classified into 8 categories: (1) simple eremophilanes (without ring C) and eudesmanes including nor-derivatives, (2) furanoeremophilanes and lactones with a 1(10)-saturated bond, (3) furanoeremophilanes and lactones with a 1(10)-unsaturated bond, 1,10-epoxide, or 10-ol, (4) furanoeremophilanes and lactones with 1(10)-en-2-one, 1(10)-en-2-ol, or 1-en-3-one, (5) furanoeremophilanes and lactones with 1(10)-en-9-one, 1(10)-en-9-ol, or 1,10-epoxy-9-one, (6) cacalol and their derivatives, (7) bakkanes and their derivatives, and (8) others, as shown in Tables 1-7. In these studies, five chemotypes were identified in addition to three clades from the DNA sequences of L. virgaurea. The structural determination of some compounds was also discussed and a comment on how to express the real structure was proposed, particularly for spiro compounds.

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Volatile Components of "San-shion"

Cited by 9 publications

References 0 publications

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Chemical and Genetic Diversity of Ligularia latihastata and Ligularia villosa in Yunnan Province of China

Terpenoid Composition and Base Sequences of <i>Ligularia virgaurea</i> (Asteraceae) Grown in the Hengduan Mountain Area in China and a Comment on Drawing Structures

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