IUPAC/Chemical Name
(4R,4'R,4aR,4'aR,7R)-rel-2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-6,6'-dimethyl-9,9'-dioxo-[7,7'-bi-4aH-xanthene]-4a,4'a-dicarboxylic acid dimethyl ester
InChi Key
NCPFIXCVFFDLAF-UHFFFAOYSA-N
InChi Code
InChI=1S/C32H30O14/c1-11-9-15-21(27(39)23-13(33)5-7-17(35)31(23,45-15)29(41)43-3)25(37)19(11)20-12(2)10-16-22(26(20)38)28(40)24-14(34)6-8-18(36)32(24,46-16)30(42)44-4/h9-10,17-18,33-38H,5-8H2,1-4H3
SMILES Code
O=C1C2=C(C=C(C)C(C3=C(O)C(C(C4=C(O)CCC(O)C4(C(OC)=O)O5)=O)=C5C=C3C)=C2O)OC6(C(OC)=O)C(O)CCC(O)=C61
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Rugulotrosin A is active against the Gram-positive bacteria E. faecalis, B. cereus, B. subtilis, and S. aureus with 99% lethal dose (LD99) values of 1.6, 3.1, 5.5, and 200 μg/ml, respectively.
In vitro activity:
Rugulotrosins A and B displayed significant antibacterial activity against Bacillus subtilis, while rugulotrosin A was also strongly active against Enterococcus faecalis and B. cereus.
Reference: J Nat Prod. 2004 Apr;67(4):728-30. https://pubmed.ncbi.nlm.nih.gov/15104517/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
638.58
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Qin T, Skraba-Joiner SL, Khalil ZG, Johnson RP, Capon RJ, Porco JA Jr. Atropselective syntheses of (-) and (+) rugulotrosin A utilizing point-to-axial chirality transfer. Nat Chem. 2015 Mar;7(3):234-40. doi: 10.1038/nchem.2173. Epub 2015 Feb 2. PMID: 25698333; PMCID: PMC4339264.
2. Stewart M, Capon RJ, White JM, Lacey E, Tennant S, Gill JH, Shaddock MP. Rugulotrosins A and B: Two new antibacterial metabolites from an Australian isolate of a Penicillium sp. J Nat Prod. 2004 Apr;67(4):728-30. doi: 10.1021/np034038b. PMID: 15104517.
In vitro protocol:
1. Qin T, Skraba-Joiner SL, Khalil ZG, Johnson RP, Capon RJ, Porco JA Jr. Atropselective syntheses of (-) and (+) rugulotrosin A utilizing point-to-axial chirality transfer. Nat Chem. 2015 Mar;7(3):234-40. doi: 10.1038/nchem.2173. Epub 2015 Feb 2. PMID: 25698333; PMCID: PMC4339264.
2. Stewart M, Capon RJ, White JM, Lacey E, Tennant S, Gill JH, Shaddock MP. Rugulotrosins A and B: Two new antibacterial metabolites from an Australian isolate of a Penicillium sp. J Nat Prod. 2004 Apr;67(4):728-30. doi: 10.1021/np034038b. PMID: 15104517.
1: Chen J, Li Y, Xiao Z, He H, Gao S. Asymmetric Synthesis of Rugulotrosin A. Org Lett. 2020 Feb 21;22(4):1485-1489. doi: 10.1021/acs.orglett.0c00063. Epub 2020 Feb 10. PMID: 32037839.
2: Smyth JE, Butler NM, Keller PA. A twist of nature--the significance of atropisomers in biological systems. Nat Prod Rep. 2015 Nov;32(11):1562-83. doi: 10.1039/c4np00121d. PMID: 26282828.
3: Qin T, Skraba-Joiner SL, Khalil ZG, Johnson RP, Capon RJ, Porco JA Jr. Atropselective syntheses of (-) and (+) rugulotrosin A utilizing point-to-axial chirality transfer. Nat Chem. 2015 Mar;7(3):234-40. doi: 10.1038/nchem.2173. Epub 2015 Feb 2. PMID: 25698333; PMCID: PMC4339264.
4: Stewart M, Capon RJ, White JM, Lacey E, Tennant S, Gill JH, Shaddock MP. Rugulotrosins A and B: Two new antibacterial metabolites from an Australian isolate of a Penicillium sp. J Nat Prod. 2004 Apr;67(4):728-30. doi: 10.1021/np034038b. PMID: 15104517.
