A new sesquiterpene, bicyclogermacrene

Nishimura, K.; Shinoda, Naoko; Hirose, Yoshio

doi:10.1016/s0040-4039(01)88358-1

Cited by 86 publications

(39 citation statements)

References 2 publications

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“…Casbene synthetase was not detected in seedlings maintained under sterile conditions throughout the period of growth. Levels as low as 10-4 unit/mg of protein would have been detected, so at least a 1,000-fold increase in casbene synthetase activity was seen 14 hr after inoculation. It seems that an interaction of the fungus and the plant is required before the seedlings acquire a significant capacity for casbene synthesis.…”

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confidence: 97%

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Biosynthesis of the Diterpene Phytoalexin Casbene

Dueber¹,

Adolf²,

West³

1978

Plant Physiol.

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Casbene synthetase from 67-hour seedings of Rkcihs communis L. which had been treated with Rhzp_5 stolonffer spores was prified 700-fold by a combination of ammonium sulfate fractionation, QAE A-50 Sephadex chromatography, and G-100 Sephadex chromatography. Polyacrylamide disc gel electrophoresis revealed that the purified fraction was heterogeneous. No casbene synthetase was detected in extracts of seedlings which had not been exposed to the fungal spores; maximum activity was obtained from seedlings 14 hours after exposure to spores.The pardally purified enzyme exbibited a broad pH optimum from pH 7.5 to 9.0 with half-maximal activty at pH 6.0 and 9.8. Chromatography on a calibrated Sephadex G-100 column nicated a molecular weight of 53,000 ± 3,000 for casbene synthetase. Concentrations of Mg2' above 5 mm gave maximal stimulation of the activity. Mn2+ was much less effective and was inhibitory at concentrations above 0.2 IM. The Km for geranylgeranyl pypsphate was estimated as 1.9 FM. The activity was inhibited 50% by 2.5 mm N-ethylmaleimlde; 10 mM iodoacetamide was not inhibitory. N,N-Dimethylaminoethyl-2,phenylpentanoate (SKF-525A) and the growth retardant 2'-Isopropyl-4'4trmethylammonum chloride)-5'-methylphenyl piperdi1ne--carboxylate (Amo-1618) were ineffective inhibitors of casbene synthetase, but the growth retardant tributyl-2,4-dichlorobenzylphosphonlum chloride (Phospbon D) at a concentration of 5 pM inhibited the activity by 55%.A cell-free system containing soluble enzymes from castor beans has been shown to synthesize five diterpene hydrocarbons from both mevalonic acid and geranylgeranyl pyrophosphate (17,18 system to produce casbene is greatly increased when the seedlings are exposed to cultures of Aspergillus niger or Rhizopus stolonifer (23) or to a partiafly purified elicitor isolated from culture filtrates of R stolonifer (24). In addition, casbene at a concentration of 10 ,ug/ml is inhibitory toward the growth of A. niger (23). It seems that casbene possesses some of the major characteristics of a phytoalexin as originally defined (6,13). None among the other known phytoalexins are hydrocarbons, and the momilactones are the only other diterpenoid substances proposed as phytoalexins (4).Most of the pathways postulated for the biosynthesis of known phytoalexins are complex with many steps involved. However, casbene is a product of a single enzyme-catalyzed transformation of GGPP, which serves as a branchpoint metabolite for several biosynthetic pathways in the castor bean. Thus, the castor bean system is ideal for the study of the enzymology and regulatory features of the production of a stress metabolite. Very little work has been reported on the enzymology associated with phytoalexin production, and none on an enzyme whose product is the phytoalexin itself. Uritani's group (15,25,26) has partially purified and measured changes in activities of some of the enzymes in the early part of the pathway leading to the sesquiterpenoid phytoalexin ipomeamarone. A recent paper by Gustine et al...

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“…7). Car-2-ene (II) is a monoterpene (22) and bicyclogermacrene (III) is a sesquiterpene (14) which also contain a fused cyclopropane substituted with gem-dimethyls. Each of these three substances probably arises in analogous fashion from an intramolecular cyclization of the appropriate acyclic prenyl pyrophosphate precursor.…”

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Biosynthesis of the Diterpene Phytoalexin Casbene

Dueber¹,

Adolf²,

West³

1978

Plant Physiol.

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“…Compound 8 has been identified on the basis of its spectroscopic and physical data as (À)-bicyclogermacrene [23] [24], which has been isolated for the first time from a marine organism, the soft coral Sinularia mayi [25].…”

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Furanocembranoids from the Soft Corals Sinularia asterolobata and Litophyton arboreum

Grote

Dahse

Seifert

2008

Chemistry & Biodiversity

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The new cembranoid diterpene danielid (1) along with 3alpha-ethoxyfuranocembranoid 2, pukalide (3), 13alpha-acetoxypukalide (4), furanocembranoid 5, and furanosesquiterpene 6 have been isolated from the soft coral Sinularia asterolobata. The furanocembranoid diterpene 11beta,12beta-epoxypukalide (7) and the sesquiterpene (-)-bicyclogermacrene (8) have been obtained from the soft coral Litophyton arboreum. The structures were elucidated primarily by NMR spectroscopy. The furanocembranoids 2, 4, and 5 show good antiproliferative activities against the cell lines L-929 and K-562, and weak cytotoxic effects on HeLa cells.

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“…The increase in the relative percentages of the sesquiterpene alcohols could to some extent be attributed to possible reactions with the germacrene hydrocarbons. It is suggested that the possible isomerization of bicyclogermacrene to tricyclic sesquiterpenes, such as aromadendrene and allo-aromadendrene and the subsequent oxidation of these isomers, could also have led to the formation of spathulenol (Nishimura, et al, 1969) (Fig. 3).…”

Section: Resultsmentioning

confidence: 99%

“…The volatile compounds of yuzu oil have been investigated by many researchers (Kusunose and Sawamura, 1980;Nishimura et al, 1969;Njoroge et al, 1994;Shinoda et al, 1970;Tajima et al, 1990;Yang et al, 1992), who report large variations in the composition of identified compounds. For instance, bicyclogermacrene, germacrene D, and germacrene B were first isolated in yuzu cold-pressed oil (CPO) by Yoshihara et al (1969), but have not been widely reported by other researchers, who have instead identified bicycloelemene, T-cadinol, spathulenol, globulol, and eudesmol as the prominent sesquiterpenoids.…”

Section: Introductionmentioning

confidence: 99%

Compositional Changes in Yuzu (Citrus junos) Steam-Distilled Oil and Effects of Antioxidants on Oil Quality during Storage

Kashiwagi

Phi

Sawamura³

2010

FSTR

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Changes in 44 compounds of yuzu (Citrus junos Sieb. ex Tanaka) steam-distilled peel oil (SDO) and possible artifacts that accrue during storage at 25℃ were investigated after 1, 2, 3, 4, 8 and 12 weeks. Changes in SDO composition during storage took place more rapidly than in cold-pressed oil. Total monoterpene hydrocarbons decreased markedly, with major losses of limonene and γ-terpinene and notable increases in p-cymene, as well as alcohols. Bicyclogermacrene, the main sesquiterpene hydrocarbon of the fresh oil, practically disappeared. (-)-Spathulenol, the main artifact, was converted from bicyclogermacrene. Antioxidants such as α-tocopherol, β-carotene and 2,6-di-tert-butyl-4-hydroxytoluene (BHT) slowed the formation of oxidation products, such as p-cymene, (-)-spathulenol by inhibiting the formation of oxidative products. This suggests that the antioxidants can be used to maintain yuzu oil quality.

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A new sesquiterpene, bicyclogermacrene

Cited by 86 publications

References 2 publications

Biosynthesis of the Diterpene Phytoalexin Casbene

Biosynthesis of the Diterpene Phytoalexin Casbene

Furanocembranoids from the Soft Corals Sinularia asterolobata and Litophyton arboreum

Compositional Changes in Yuzu (Citrus junos) Steam-Distilled Oil and Effects of Antioxidants on Oil Quality during Storage

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