Torreyanic acid
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| Category | Others |
| Catalog number | BBF-05002 |
| CAS | 176260-42-7 |
| Molecular Weight | 692.75 |
| Molecular Formula | C38H44O12 |
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Description
Torreyanic acid is a dimer quinone obtained from the endophytic bacterium Pestalotiopsis microspora. Torreyanic acid is cytotoxic to tumor cells and is 5-10 times more effective in cell lines sensitive to protein kinase C agonists.
Specification
| IUPAC Name | (E)-4-[(2S,4S,6R,11R,12S,16S,18R)-4-[(E)-3-carboxybut-2-enyl]-3,7,15,19-tetraoxo-11,22-dipentyl-5,10,17,21-tetraoxaheptacyclo[11.7.2.02,8.02,12.04,6.014,20.016,18]docosa-8,14(20)-dien-16-yl]-2-methylbut-2-enoic acid |
| Canonical SMILES | CCCCCC1C2C3C(OC=C4C3(C(O1)C5=C2C(=O)C6(C(C5=O)O6)CC=C(C)C(=O)O)C(=O)C7(C(C4=O)O7)CC=C(C)C(=O)O)CCCCC |
| InChI | InChI=1S/C38H44O12/c1-5-7-9-11-21-23-24-25(28(40)32-36(49-32,29(24)41)15-13-18(3)33(42)43)30(48-21)38-20(17-47-22(26(23)38)12-10-8-6-2)27(39)31-37(50-31,35(38)46)16-14-19(4)34(44)45/h13-14,17,21-23,26,30-32H,5-12,15-16H2,1-4H3,(H,42,43)(H,44,45)/b18-13+,19-14+/t21?,22-,23?,26+,30?,31+,32+,36-,37+,38-/m1/s1 |
| InChI Key | DQBVXDMPCDAQGS-YOWCJFHESA-N |
Properties
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
Reference Reading
1. Two ambuic acid dimers derived from homo- endo Diels-Alder reaction from Pestalotiopsis versicolor
Dan-Yi Li, Xiao-Ling Zhang, Zhan-Lin Li J Asian Nat Prod Res. 2022 Oct 20;1-9. doi: 10.1080/10286020.2022.2132480. Online ahead of print.
Two new dimers of ambuic acid, pestaloversicoloric acids A (1) and B (2), and a known derivative, 13(S)-hydroxyambuic acid (3), were isolated from the static fermentation product of Pestalotiopsis versicolor. The structural identification was accomplished via analyses on the data of HR-MS, 1 D and 2 D NMR, and ECD. Different from the well-known exo-type dimer, torreyanic acid, compounds 1 and 2 represent the first example of endo-type product derived from the intermolecular Diels-Alder reaction of two molecules of ambuic acid derivative with the identical absolute stereochemistry.
2. Ambuic acid and torreyanic acid derivatives from the endolichenic fungus Pestalotiopsis sp
Gang Ding, Yan Li, Shaobin Fu, Shuchun Liu, Jiangchun Wei, Yongsheng Che J Nat Prod. 2009 Jan;72(1):182-6. doi: 10.1021/np800733y.
Six new ambuic acid (1) derivatives (2-7) and a new torreyanic acid analogue (8) have been isolated from the crude extract of endophytic fungus Pestalotiopsis sp. inhabiting the lichen Multiclavula [corrected] sp. The structures of these compounds were elucidated primarily by NMR and MS methods, and their absolute configurations were assigned by application of the CD excitation chirality method. Compounds 1 and 2 displayed antimicrobial activity against the Gram-positive bacterium Staphylococcus aureus.
3. Total synthesis of the novel, biologically active epoxyquinone dimer (+/-)-torreyanic acid: a biomimetic approach
Goverdhan Mehta, Subhas Chandra Pan Org Lett. 2004 Oct 28;6(22):3985-8. doi: 10.1021/ol0483551.
[reaction: see text] A total synthesis of the complex, biologically active, dimeric natural product (+/-)-torreyanic acid, which is composed of seven rings and laced with dense, variegated oxy-functionalization, has been accomplished from readily available allyl-substituted p-benzoquinone 8. Our synthetic stratagem involves crafting an epoxyquinone monomer for use in a biomimetic cascade process involving tandem a 6pi electrocyclization and a Diels-Alder dimerization.
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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 ╳
