Acoradiene, (-)-beta-
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| Category | Others |
| Catalog number | BBF-05118 |
| CAS | 28477-64-7 |
| Molecular Weight | 204.35 |
| Molecular Formula | C15H24 |
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Specification
| Synonyms | Spiro[4.5]dec-7-ene, 1-isopropenyl-4,8-dimethyl-, (1S,4R,5R)-(+)- (8CI) |
| IUPAC Name | (1R,4S,5R)-1,8-dimethyl-4-prop-1-en-2-ylspiro[4,5]dec-8-ene |
| Canonical SMILES | CC1CCC(C12CCC(=CC2)C)C(=C)C |
| InChI | InChI=1S/C15H24/c1-11(2)14-6-5-13(4)15(14)9-7-12(3)8-10-15/h7,13-14H,1,5-6,8-10H2,2-4H3/t13-,14+,15+/m1/s1 |
| InChI Key | DVBSKQAFCDJNSL-ILXRZTDVSA-N |
Properties
| Boiling Point | 273.1±20.0°C (Predicted) |
| Density | 0.89±0.1 g/cm3 (Predicted) |
Reference Reading
1. Ectomycorrhizal Influence on the Dynamics of Sesquiterpene Release by Tricholoma vaccinum
Marycolette Ndidi Ezediokpu, Katrin Krause, Maritta Kunert, Dirk Hoffmeister, Wilhelm Boland, Erika Kothe J Fungi (Basel). 2022 May 24;8(6):555. doi: 10.3390/jof8060555.
Tricholoma vaccinum is an ectomycorrhizal basidiomycete with high host specificity. The slow-growing fungus is able to produce twenty sesquiterpenes, including α-barbatene, sativene, isocaryophyllene, α-cuprenene, β-cedrene, ß-copaene, 4-epi-α-acoradiene, and chamigrene in axenic culture. For the three major compounds, Δ6-protoilludene, β-barbatene, and an unidentified oxygenated sesquiterpene (m/z 218.18), changed production during co-cultivation with the ectomycorrhizal partner tree, Picea abies, could be shown with distinct dynamics. During the mycorrhizal growth of T. vaccinum-P. abies, Δ6-protoilludene and the oxygenated sesquiterpene appeared at similar times, which warranted further studies of potential biosynthesis genes. In silico analyses identified a putative protoilludene synthesis gene, pie1, as being up-regulated in the mycorrhizal stage, in addition to the previously identified, co-regulated geosmin synthase, ges1. We therefore hypothesize that the sesquiterpene synthase pie1 has an important role during mycorrhization, through Δ6-protoilludene and/or its accompanied oxygenated sesquiterpene production.
2. Reprogramming the chemodiversity of terpenoid cyclization by remolding the active site contour of epi-isozizaene synthase
Ruiqiong Li, Wayne K W Chou, Julie A Himmelberger, Kevin M Litwin, Golda G Harris, David E Cane, David W Christianson Biochemistry. 2014 Feb 25;53(7):1155-68. doi: 10.1021/bi401643u. Epub 2014 Feb 11.
The class I terpenoid cyclase epi-isozizaene synthase (EIZS) utilizes the universal achiral isoprenoid substrate, farnesyl diphosphate, to generate epi-isozizaene as the predominant sesquiterpene cyclization product and at least five minor sesquiterpene products, making EIZS an ideal platform for the exploration of fidelity and promiscuity in a terpenoid cyclization reaction. The hydrophobic active site contour of EIZS serves as a template that enforces a single substrate conformation, and chaperones subsequently formed carbocation intermediates through a well-defined mechanistic sequence. Here, we have used the crystal structure of EIZS as a guide to systematically remold the hydrophobic active site contour in a library of 26 site-specific mutants. Remolded cyclization templates reprogram the reaction cascade not only by reproportioning products generated by the wild-type enzyme but also by generating completely new products of diverse structure. Specifically, we have tripled the overall number of characterized products generated by EIZS. Moreover, we have converted EIZS into six different sesquiterpene synthases: F96A EIZS is an (E)-β-farnesene synthase, F96W EIZS is a zizaene synthase, F95H EIZS is a β-curcumene synthase, F95M EIZS is a β-acoradiene synthase, F198L EIZS is a β-cedrene synthase, and F96V EIZS and W203F EIZS are (Z)-γ-bisabolene synthases. Active site aromatic residues appear to be hot spots for reprogramming the cyclization cascade by manipulating the stability and conformation of critical carbocation intermediates. A majority of mutant enzymes exhibit only relatively modest 2-100-fold losses of catalytic activity, suggesting that residues responsible for triggering substrate ionization readily tolerate mutations deeper in the active site cavity.
3. Volatiles of Helichrysum italicum (Roth) G. Don from Croatia
Sanja Ćavar Zeljković, Marija Edita Šolić, Milka Maksimović Nat Prod Res. 2015;29(19):1874-7. doi: 10.1080/14786419.2015.1009458. Epub 2015 Feb 12.
Helichrysum italicum (Roth) G. Don is a flowering plant of the family Asteraceae. It is rich in oil that is used for different medicinal purposes and in fragrance industry. Volatile profile of four populations of H. italicum, collected from natural habitat in Dalmatia (Croatia), was analysed by capillary GC-MS. Sample from BraČ Island had α-trans-bergamotene (10.2%) and β-acoradiene (10.1%) as the majors, whereas sample collected on Biokovo Mt. was rich in neryl acetate (8.1%). β-Acoradiene was also the main constituent of sample collected near Tijarica, whereas rosifoliol (8.5%) was the most abundant constituent in sample collected near Makarska. Presented results show the influence of environmental conditions on chemical differentiation of the volatiles of H. italicum from Croatia.
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Bio Calculators
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