Sesquiterpenoids from the wood of Roxb; partial synthesis of t-muurolol, t-cadinol and cubenol; structures of δ -cadinene and δ -cadinol

Nagasampagi, B. A.; Yankov, L.; Dev, Sukh

doi:10.1016/s0040-4039(01)99055-0

Cited by 39 publications

(20 citation statements)

References 18 publications

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“…In addition, γ-cadinene is more abundant in these essential oils than α-cadinene. α-Cadinene has been shown to undergo acid-catalyzed rearrangement to give β-cadinene [16,30], which in turn, has been found to isomerize to ω-cadinene [16,[30][31][32], in agreement with the calculated energies; β-cadinene and ω-cadinene are lower in energy than α-cadinene by 1.88 kcal/mole and 2.90 kcal/mol, respectively. Bülow and König [16,24] reported that ω-cadinene can be formed from δ-cadinene in a 1.4:1 ratio, consistent with the nearly equal calculated energies.…”

Section: Discussionsupporting

confidence: 73%

Chemical compositions of the essential oil and calculation the biophysicochemical coefficients of the components of Hymenocrater longiflorus Benth. of Iran

Maroofi¹,

Changizi²,

Shoushtari³

et al. 2011

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The volatile constituents of the essential oil of Hymenocrater longiflorus Benth. growing wild in Kurdistan-Iran were investigated using the GC and GC/MS techniques. Fifteen compounds, representing twenty (97.03%) of the total oil were identified. The main components were: α-Pinene (22.47%), β-Caryophyllene (18.05%), β-Eudesmol (14.92%), α-Copaene (9.84%), γ-Elemene (6.79%), δ-Cadine-ne (6.13%), (-)Bornyl acetate (5.61%), α-Amorphene (3.84%), α-Fenchyl acetate (2.35%) and β-Pinene (2.07%). Some of the physicochemical properties like the logarithm of calculated Octanol-Water partitioning coefficients (log K ow ) , total biodegradation and (TB d in mol/h and gr./h), water solubility (S w , mg.L -1 at 25ºC) and median lethal concentration 50 (LC 50 ) were calculated for the 15 components of Hymenocrater longiflorus Benth.

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Section: Discussionsupporting

confidence: 73%

Chemical compositions of the essential oil and calculation the biophysicochemical coefficients of the components of Hymenocrater longiflorus Benth. of Iran

Maroofi¹,

Changizi²,

Shoushtari³

et al. 2011

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“…Of these sequiterpenes only α-copaene and β-elemene were found in the present study. The second case is more interesting since the literature registers the occurrence of only α-copaene in T. ciliata 20 . The oils of C. fissilis had not been analysed previously.…”

Section: Trans-farnesyl Derivativesmentioning

confidence: 99%

Essential oils of Toona and Cedrela Species (Meliaceae): taxonomic and ecological implications

Maia¹,

Paula²,

Santana³

et al. 2000

J. Braz. Chem. Soc.

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Os óleos essenciais de Toona ciliata, Cedrela odorata e C. fissilis foram analisados por CG-EM. Cedrela apresentou em maior percentagem sesquiterpenos formados a partir do precursor pirofosfato de cis-e trans-farnesila. Já Toona mostra uma tendência em produzir principalmente sesquiterpenos derivados do pirofosfato de trans-farnesila. Estes resultados confirmam que a classificação destes dois gêneros em uma mesma tribo, Cedreleae, continua problemática. As respostas em eletroantenogramas médios (EAGs) dos óleos essenciais de T. ciliata e C. odorata, em fêmeas de Hypsipyla grandella, foram significativamente maiores que aquelas obtidas em machos, sugerindo que as fêmeas utilizariam os odores destes óleos para a seleção da planta hospedeira (gêneros de Swietenioidea) e na escolha de locais para oviposição.The essential oils of Toona ciliata, Cedrela odorata and C. fissilis have been analysed by GC-MS. Cedrela contains the main sesquiterpenes formed from the cis-and trans-farnesyl pyrophosphate. In contrast, Toona tend to produce mainly sesquiterpenes formed from the trans-precursor. These results show that the affiliation of Toona in the tribe Cedreleae together with Cedrela is still rather problematic. Mean electroantennogram responses (EAGs) to the essential oils from T. ciliata and C. odorata, in Hypsipyla grandella females were significantly greater than those obtained for males, suggesting that females would use attractant odours messages from the host-plant (genera of Swietenioideae) as search strategy behaviour for habitat location and oviposition.

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“…1). Therefore, the MeOH fraction was further separated on a silica gel column eluted with stepwise gradients of nhexane-EtOAc and then purified by HPLC to give compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) as shown in Fig. 2 .…”

Section: Resultsmentioning

confidence: 99%

“…Two new compounds (1, 2) and seventeen known compounds (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) were isolated from the leaves of B. dracunculifolia and the chemical structures were determined by spectroscopic means. Cytotoxicity testing of the compounds isolated in this study revealed the monoterpene phenols like compounds 4, 6, and 17 (dimer) and the sesquiterpene alcohols such as compounds 8, 10, 11, 13, and 16 exhibited strong cytotoxicity.…”

Section: Resultsmentioning

confidence: 99%

“…Our biological studies of the alcoholic extracts of the leaves found that the extracts exhibited potent cytotoxic activity against leukemia cells (L 1210). In this paper, we describe the isolation and structure elucidation of two new compounds, baccharisketone (1) and p-methoxythymol acetate (2), along with seventeen known compounds; caryophyllene oxide (3), 6) thymol (4), 7) carvacrol (5), 8) p-methoxythymol (6), 8) 4-isopropyl-2-methylphenol (7), 7) spathulenol (8), 9) p-cymene-2,3-diol (9), 10) bisacumol (10), 11) 2-methyl-6-(4Ј-methylphenyl)-3-hepten-2-ol (11), 12) 1b-hydroxyeudesma-4(15),7-diene (12), 13) cadinol (13), 14) an oppositanetype sesquiterpene (14), 15) germacra-1(11),5(12),6(E)-trien-2-ol (15), 16) a tricyclic sesquiterpene (16), 15) 3,4,3Ј,4Ј-tetrahydroxy-5,5Ј-diisopropyl-2,2Ј-dimethylbiphenyl (17), 17) 3-acetoxy-4Ј,5-dihydroxy-7-methoxyflavanone (18), 18) and naringenin (19), 19) and discuss their growth inhibitory activities against L 1210.…”

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confidence: 99%

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Studies on the Constituents of the Leaves of Baccharis dracunculifolia (Asteraceae) and their Cytotoxic Activity

Fukuda

Ohkoshi

Makino

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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A new sesquiterpene, named baccharisketone (1), and a new monoterpene, p-methoxythymol acetate (2), were isolated from the leaves of Baccharis dracunculifolia along with seventeen known compounds (3-19). The structures of the new compounds were determined by spectroscopic means. The growth inhibitory activity of the isolated compounds against leukemia cells (L 1210) was tested and three terpene phenols (4, 6, 17) and five sesquiterpene alcohols (8, 10, 11, 13, 16) were found to exhibit strong cytotoxic activity.

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Sesquiterpenoids from the wood of Roxb; partial synthesis of t-muurolol, t-cadinol and cubenol; structures of δ -cadinene and δ -cadinol

Cited by 39 publications

References 18 publications

Chemical compositions of the essential oil and calculation the biophysicochemical coefficients of the components of Hymenocrater longiflorus Benth. of Iran

Chemical compositions of the essential oil and calculation the biophysicochemical coefficients of the components of Hymenocrater longiflorus Benth. of Iran

Essential oils of Toona and Cedrela Species (Meliaceae): taxonomic and ecological implications

Studies on the Constituents of the Leaves of Baccharis dracunculifolia (Asteraceae) and their Cytotoxic Activity

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