Terrecyclic acid
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| Category | Antibiotics |
| Catalog number | BBF-03500 |
| CAS | 83058-94-0 |
| Molecular Weight | 248.32 |
| Molecular Formula | C15H20O3 |
| Purity | >95% by HPLC |
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Description
Terrecyclic acid is an antibiotic produced by Asptrgillus terreus No. 14. It has weak anti-Gram-positive bacteria and fungus activity, and has an inhibitory effect on leukemia cells P388.
Specification
| Synonyms | Terrecyclic acid A; (+)-terrecyclic acid A |
| Storage | -20°C |
| IUPAC Name | (1S,5R,6R,9R)-11,11-dimethyl-2-methylidene-3-oxotricyclo[4.3.2.01,5]undecane-9-carboxylic acid |
| Canonical SMILES | CC1(CC23C(CCC1C2CC(=O)C3=C)C(=O)O)C |
| InChI | InChI=1S/C15H20O3/c1-8-12(16)6-11-9-4-5-10(13(17)18)15(8,11)7-14(9,2)3/h9-11H,1,4-7H2,2-3H3,(H,17,18)/t9-,10+,11-,15-/m1/s1 |
| InChI Key | SMAWCSOVJJHIOI-JNIYBQFBSA-N |
| Source | Aspergillus terreus |
Properties
| Appearance | White Crystal Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi |
| Boiling Point | 413.4°C at 760 mmHg |
| Melting Point | 122°C |
| Density | 1.18 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. |
Reference Reading
1. Molecular structure of terrecyclodiol: a derivative of the antifungal metabolite terrecyclic acid A from Aspergillus terreus
B W Skelton, A H White, E L Ghisalberti, F Almassi J Nat Prod . 1996 Jan;59(1):59-61. doi: 10.1021/np960008f.
A strain of Aspergillus terreus, which was isolated from organic mulch and inhibited the growth of the plant pathogen Phytophthora cinnamomi, produces an antifungal metabolite when grown in liquid culture. This metabolite was isolated by bioassay-guided fractionation and identified as terrecyclic acid A (1). X-ray diffraction studies and spectroscopic details of the derived terrecyclodiol (2) are described.
2. Cytotoxic constituents of Aspergillus terreus from the rhizosphere of Opuntia versicolor of the Sonoran Desert
Zhongge Zhang, Hans D VanEtten, Louise M Canfield, A A Leslie Gunatilaka, Leland S Pierson 3rd, Donna Bigelow, Luke Whitesell, Thomas J Turbyville, E M Kithsiri Wijeratne J Nat Prod . 2003 Dec;66(12):1567-73. doi: 10.1021/np030266u.
A novel cyclopentenedione, asterredione (1), two new terrecyclic acid A derivatives, (+)-5(6)-dihydro-6-methoxyterrecyclic acid A (2) and (+)-5(6)-dihydro-6-hydroxyterrecyclic acid A (3), and five known compounds, (+)-terrecyclic acid A (4), (-)-quadrone (5), betulinan A (6), asterriquinone D (7), and asterriquinone C-1 (8), were isolated from Aspergillus terreus occurring in the rhizosphere of Opuntia versicolor, using bioassay-guided fractionation. Acid-catalyzed reaction of 2 under mild conditions afforded 4, whereas under harsh conditions 2 yielded 5 and (-)-isoquadrone (9). Catalytic hydrogenation and methylation of 4 afforded 5(6)-dihydro-terrecyclic acid A (10) and (+)-terrecyclic acid A methyl ester (11), respectively. The structures of 1-11 were elucidated by spectroscopic methods. All compounds were evaluated for cytotoxicity in a panel of three sentinel cancer cell lines, NCI-H460 (non-small cell lung cancer), MCF-7 (breast cancer), and SF-268 (CNS glioma), and were found to be moderately active. Cell cycle analysis of 2, 4, and 5 using the NCI-H460 cell line indicated that 4 is capable of disrupting the cell cycle through an apparent arrest to progression at the G(1) and G(2)/M phases in this p53 competent cell line. A pathway for the biosynthetic origin of asterredione (1) from asterriquinone D (7) is proposed.
3. Studies on the biosynthesis of terrecyclic acid A, an antitumor antibiotic from Aspergillus terreus
R L Chapman, J M Beale Jr, J P Rosazza J Antibiot (Tokyo) . 1984 Nov;37(11):1376-81. doi: 10.7164/antibiotics.37.1376.
The biosynthesis of terrecyclic acid A was investigated using 13C-labeled acetates and mevalonate. 13C NMR spectral analysis of isolated labeled terrecyclic acid demonstrated that the structure is assembled via an isoprene pathway.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
