Chemical Constituents of Essential Oil of Chamaecyparis Obtusa(SIEB. et ZUCC.)

Fujise, Yutaka; Maruta, Isao; Itô, Shô; Nozoe, Tetsuo

doi:10.1248/cpb.12.991

Cited by 10 publications

(5 citation statements)

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“…(Kuromatsu) (Japanese Black Pine) although no analyses were given (SHINOZAKI, 1918;AKIYOSHI 1937;AKT-YOSHI et al 1960). In contrast, detailed analyses have been presented (PAULY et al, 1973;GLEIZES, 1976) (fam. Cupressaceae; Alaskan Yellow or Nootka Cedar) have been subject to intense study (CHENG and VON RUDLOFF, 1970;ANDERSEN and SYNDAL, 1970): in the first case no longibornanes were reported from the needle oil, although the latter yielded a little longifolene (0.8010 w/w oil).…”

Section: Resultsmentioning

confidence: 99%

Distribution of Longibornane Sesquiterpenes

Banthorpe¹,

Duprey²,

Janes³

et al. 1977

Planta Med

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Essentially complete analyses are reported of the sesquiterpene fractions from the leaf oils of Pinus l o n g i f o l i a , P. pinaster, P. t h u n b e r g i i , P. d e n s iflora, C h a m a e c y p a r i s n o o t k a t e n s i s and C. o b t u s a and of oil from the liverwort S cap a n ia u n d u 1 a t a. These species have been recorded as sources of longi/olene and related compounds but the present results differ considerably from those of the previous (often incomplete) analyses. The best sources of longifolene and its relatives were P. p i n a st e r and S. u n d u 1 at a (1 6; 46 O/o of the steam volatile oil respectively) and enantiomorphic compounds were found in the two species. lntroduction Longifolene (I: decahydro-4,8,8-trimethyl-9-methylene-1,4-methanoazulene) is a sesquiterpene with an unusual skeleton that occurs in the natural orders Pinales, Cupressales, and Podocarpales (cf. AKIYOSHI et al., 1960;ZAVARIN et al., 1968); its main source, namely Pinus longifolia, is used in the Indian subcontinent in folk medicine (CHAUDHRY, 1974). Related sesquiterpenes which by analogy with monoterpenes may be classified as members of the longibornane series, are longi-borne01 (11), longicamphor (111), longicyclene (IV) and a-longipinene (V) (cf. VON SCHANTZ and JUVONEN, 1967;SMEDMAN et al. 1969 a, b;and NAYAK and DEV, 1963); these are infrequently found in nature and are always present in smaller proportions than the co-occurring longifolene (Figure 1).

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Section: Resultsmentioning

confidence: 99%

Distribution of Longibornane Sesquiterpenes

Banthorpe¹,

Duprey²,

Janes³

et al. 1977

Planta Med

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“…Studies show that the composition of essential oils is significantly influenced not only by the part of the plant, but also by its place of origin. Fujise et al compared oil obtained from the leaves and wood of C. obtusa and indicated differences from commercial oil [ 27 ]. Another class of compounds, similar to terpenes, are the terpenoids, where the ‘isoprene rule’ is not required to be followed and the compounds may have other functional groups [ 28 ].…”

Section: Phytochemistry Of Chamaecyparis Obtusamentioning

confidence: 99%

The Precious Potential of the Sacred Tree Chamaecyparis obtusa (Siebold & Zucc.) Endl. as a Source of Secondary Metabolites with Broad Biological Applications

Górski,

Kowalczyk,

Picot

et al. 2024

IJMS

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Chamaecyparis obtusa (Siebold & Zucc.) Endl., which belongs to the Cupressaceae family, occurs naturally in North America and Asia, especially in Korea, Taiwan and Japan, where it is an evergreen, coniferous, sacred, ethnic tree. It has many useful varieties that are widespread throughout the world and grown for decorative purposes. It is most commonly used as an ornamental plant in homes, gardens or parks. It is also widely used in many areas of the economy; for example, its wood is used in architecture as well as furniture production. In addition, oil extracted from Chamaecyparis obtusa is increasingly used in cosmetology for skin care. Due to its wide economic demand, mainly in Japan, it represents the largest area of plantation forest. Despite this, it is on the red list of endangered species. Its use in ethnopharmacology has led to more and more research in recent years in an attempt to elucidate the potential mechanisms of its various biological activities, such as antimicrobial, antioxidant, anticancer, antidiabetic, antiasthmatic, anti-inflammatory, antiallergic, analgesic and central nervous system effects. It has also been shown that Chamaecyparis obtusa can be used as an insect repellent and an ingredient in plant disease treatment. This thesis provides a comprehensive review of the biological studies to date, looking at different areas of the economic fields of potential use of Chamaecyparis obtusa.

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“…Its reaction with MeMgI via protection of the alcohol functions as tetrahydropyranyl (THP) ethers yielded 11, the same triol that was also obtained through hydroboration and oxidation of 2. [25] Elemol (2) was later reisolated from various plants including Juniperus sabina and J. scopulorum, [26,27] Chamaecyparis obtusa, [28] Citrus sinensis and C. nobilis, [29][30][31] Saussurea lappa, [32] Cinnamomum camphora, [33] Fokiena hodginsii, [34] Calycanthus floridus, [35] Bunium cylindricum, [36] Gingko biloba, [37] Amyris balsamifera, [38] Canarium zeylanicum, [39] Bothriocloa intermedia, [40] Commiphora abyssimica, [41] Santolina oblongifolia, [42] Cymbopogon proximus, [43] Eremophila flaccida, [44] Piper ribesioides, [45] Monocyclanthus vignei, [46] Neocallitropsis pancheri, [47] Cryptomeria japonica, [48] and Eucalyptus maculata, [49] which demonstrates the widespread occurrence of 1 in nature. After its first report from H. angustifolia, [23] compound 1 was subsequently also isolated from the undistilled oils of the plants Phebalium ozothamnoides, [50] Rubus rosifolius, [51] Thujopsis dolabrata, [52] Thymus praecox, [53] Cryptomeria japonica and C. fortunei, [54] and Chamaecyparis obtusa.…”

Section: Structure Elucidation and Occurrence In Naturementioning

confidence: 99%

“…[120] The isomer 27 was first obtained as a synthetic material [121] followed by its isolation from Alpinia japonica ([α] D = À 14.9). [122] (À )-Hinesol (28) was first reported from Atractylodes lancea ([α] D = À 40.2) and shown to be a constituent of "atractylol" that was initially believed to be a pure compound. [123] Its structure was initially wrongly assigned, [124] but later corrected with a suggested absolute configuration based on its co-occurrence with (+)-β-eudesmol (15).…”

Section: Eudesmols From Cation I1mentioning

confidence: 99%

Hedycaryol – Central Intermediates in Sesquiterpene Biosynthesis, Part II

Dickschat

2022

Chemistry A European J

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The known sesquiterpenes that arise biosynthetically from hedycaryol are summarised. Reasonings for the assignments of their absolute configurations are discussed. The analysis provided here suggests that reprotonations at the C1=C10 double bond of hedycaryol are directed toward C1 and generally lead to 6–6 bicyclic compounds, while reprotonations at the C4=C5 double bond occur at C4 and result in 5–7 bicyclic compounds. Read more in the Review by H. Xu and J. S. Dickschat (DOI: 10.1002/chem.202200405).

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Chemical Constituents of Essential Oil of Chamaecyparis Obtusa(SIEB. et ZUCC.)

Cited by 10 publications

References 0 publications

Distribution of Longibornane Sesquiterpenes

Distribution of Longibornane Sesquiterpenes

The Precious Potential of the Sacred Tree Chamaecyparis obtusa (Siebold & Zucc.) Endl. as a Source of Secondary Metabolites with Broad Biological Applications

Hedycaryol – Central Intermediates in Sesquiterpene Biosynthesis, Part II

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