Germacrene D |
| 카탈로그 번호: GC40261 |
Germacrene D는 Bursera 종에서 분리됩니다. Germacrene D는 항균 및 항진균 활성을 가지며 아미노글리코사이드 및 아졸의 적용에서 보조제로 사용될 수 있습니다.
Sample solution is provided at 25 µL, 10mM.
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Germacrene D is a major volatile component of Bursera species and a precursor in sesquiterpene biosynthesis in a variety of plants, including Solidago species.[1],[2]
Reference:
[1]. Noge, K., and Becerra, J.X. Germacrene D, a common sesquiterpene in the genus Bursera (Burseraceae). Molecules 14(12), 5289-5297 (2009).
[2]. Bülow, N., and König, W.A. The role of germacrene D as a precursor in sesquiterpene biosynthesis: Investigations of acid catalyzed, photochemically and thermally induced rearrangements. Phytochemistry 55(2), 141-168 (2000).
| Cas No. | 23986-74-5 | SDF | |
| 동의어 | (-)-Germacrene D | ||
| Chemical Name | (1E)-1-methyl-5-methylene-8S-(1-methylethyl)-1,6E-cyclodecadiene | ||
| Canonical SMILES | C=C1/C=C/[C@H](C(C)C)CC/C(C)=C\CC1 | ||
| Formula | C15H24 | M.Wt | 204.4 |
| 용해도 | Slightly soluble in chloroform or DMSO | Storage | Store at -20°C,protect from light |
| 일반적인 팁 | 높은 용해도를 얻기 위해 튜브를 37℃에서 데운 후 초음파 욕조에서 잠시 흔들어 주십시오. 원액은 -20℃ 이하에서 수개월간 보관할 수 있습니다. | ||
| 배송 조건 | 평가 샘플 솔루션: 블루아이스와 함께 배송합니다. 다른 모든 가능한 크기: 요청 시 RT 또는 블루아이스와 함께 배송합니다. | ||
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Identification of the sesquiterpene synthase AcTPS1 and high production of (-)-germacrene D in metabolically engineered Saccharomyces cerevisiae
Microb Cell Fact 2022 May 18;21(1):89.PMID:35585553DOI:10.1186/s12934-022-01814-4.
Background: The sesquiterpene Germacrene D is a highly promising product due to its wide variety of insecticidal activities and ability to serve as a precursor for many other sesquiterpenes. Biosynthesis of high value compounds through genome mining for synthases and metabolic engineering of microbial factories, especially Saccharomyces cerevisiae, has been proven to be an effective strategy. However, there have been no studies on the de novo synthesis of Germacrene D from carbon sources in microbes. Hence, the construction of the S. cerevisiae cell factory to achieve high production of Germacrene D is highly desirable. Results: We identified five putative sesquiterpene synthases (AcTPS1 to AcTPS5) from Acremonium chrysogenum and the major product of AcTPS1 characterized by in vivo, in vitro reaction and NMR detection was revealed to be (-)-germacrene D. After systematically comparing twenty-one Germacrene D synthases, AcTPS1 was found to generate the highest amount of (-)-germacrene D and was integrated into the terpene precursor-enhancing yeast strain, achieving 376.2 mg/L of (-)-germacrene D. Iterative engineering was performed to improve the production of (-)-germacrene D, including increasing the copy numbers of AcTPS1, tHMG1 and ERG20, and downregulating or knocking out other inhibitory factors (such as erg9, rox1, dpp1). Finally, the optimal strain LSc81 achieved 1.94 g/L (-)-germacrene D in shake-flask fermentation and 7.9 g/L (-)-germacrene D in a 5-L bioreactor, which is the highest reported (-)-germacrene D titer achieved to date. Conclusion: We successfully achieved high production of (-)-germacrene D in S. cerevisiae through terpene synthase mining and metabolic engineering, providing an impressive example of microbial overproduction of high-value compounds.
Germacrene D cyclization: an Ab initio investigation
Int J Mol Sci 2008 Jan;9(1):89-97.PMID:19325722DOI:10.3390/ijms9010089.
Essential oils that contain large concentrations of Germacrene D are typically accompanied by cadinane sesquiterpenoids. The acid-catalyzed cyclization of Germacrene D to give cadinane and selinane sesquiterpenes has been computationally investigated using both density functional (B3LYP/6-31G(*)) and post Hartree-Fock (MP2/6-31G(* *)) ab initio methods. The calculated energies are in general agreement with experimentally observed product distributions, both from acid-catalyzed cyclizations as well as distribution of the compounds in essential oils.
Tissue specificity of (E)-β-farnesene and Germacrene D accumulation in pyrethrum flowers
Phytochemistry 2021 Jul;187:112768.PMID:33932787DOI:10.1016/j.phytochem.2021.112768.
Plant defensive mimicry based on the aphid alarm pheromone (E)-β-farnesene (EβF) was previously shown to operate in Tanacetum cinerariifolium (Asteraceae) flowers. Germacrene D (GD), is another dominant volatile of T. cinerariifolium flowers and may modulate both defense and pollination. Here, we find that the increase in GD/EβF ratio at later developmental stages is correlated with the tissue distribution in the flower head: the total content of EβF and GD is similar, but GD accumulates comparatively more in the upper disk florets. Naphthol and N, N-dimethyl-p-phenylenediamine dihydrochloride (NADI)-stained purple ducts containing EβF and GD, were observed in the five petal lips of the corolla and two-lobed stigma of disk florets. By contrast in the peduncle, EβF accounts for nearly 80% of total terpenes, compared to 5% for GD. EβF is accumulated inside inner cortex cells and parenchyma cells of the pith in young peduncle. This is followed by the formation of terpene-filled axial secretory cavities parallel to the vascular bundles. In conclusion, the observed developmental and diurnal emissions of different EβF/GD ratios appear to be regulated by their tissue distribution.
Germacrene D, a common sesquiterpene in the genus Bursera (Burseraceae)
Molecules 2009 Dec 15;14(12):5289-97.PMID:20032892DOI:10.3390/molecules14125289.
The volatile components of the leaves of five Bursera species, B. copallifera, B. exselsa, B. mirandae, B. ruticola and B. fagaroides var. purpusii were determined by gas chromatography-mass spectrometry (GC-MS). Germacrene D was one of the predominant components (15.1-56.2%) of all of these species. Germacrene D has also been found in other Bursera species and some species of Commiphora, the sister group of Bursera, suggesting that the production of Germacrene D might be an ancient trait in the genus Bursera.
(-)-Germacrene D receptor neurones in three species of heliothine moths: structure-activity relationships
J Comp Physiol A Neuroethol Sens Neural Behav Physiol 2003 Jul;189(7):563-77.PMID:12827423DOI:10.1007/s00359-003-0434-y.
Specificity of olfactory receptor neurones plays an important role in food and host preferences of a species, and may have become conserved or changed in the evolution of polyphagy and oligophagy. We have identified a major type of plant odour receptor neurones responding to the sesquiterpene Germacrene D in three species of heliothine moths, the polyphagous Heliothis virescens and Helicoverpa armigera and the oligophagous Helicoverpa assulta. The neurones respond with high sensitivity and selectivity to (-)-germacrene D, as demonstrated by screening via gas chromatography with numerous mixtures of plant volatiles. Germacrene D was present in both host and non-host plants, but only in half of the tested species. The specificity of the neurones was similar in the three species, as shown by the "secondary" responses to a few other sesquiterpenes. The effect of (-)-germacrene D was about ten times stronger than that of the (+)-enantiomer, which again was about ten times stronger than that of (-)-alpha-ylangene. Weaker effects were obtained for (+)-beta-ylangene, (+)-alpha-copaene, beta-copaene and two unidentified sesquiterpenes. The structure-activity relationship shows that the important properties of (-)-germacrene D in activating the neurones are the ten-membered ring system and the three double bonds acting as electron-rich centres, in addition to the direction of the isopropyl-group responsible for the different effects of the Germacrene D enantiomers.
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