Synonym
Palmarumycin C3; Palmarumycin-C3;
IUPAC/Chemical Name
(1a'R,7a'S)-3',6'-dihydroxy-1a',7a'-dihydro-7'H-spiro[naphtho[1,8-de][1,3]dioxine-2,2'-naphtho[2,3-b]oxiren]-7'-one
InChi Key
BDXBHYOFNNANPN-RTBURBONSA-N
InChi Code
InChI=1S/C20H12O6/c21-10-7-8-11(22)16-15(10)17(23)18-19(24-18)20(16)25-12-5-1-3-9-4-2-6-13(26-20)14(9)12/h1-8,18-19,21-22H/t18-,19-/m1/s1
SMILES Code
OC1=C2C3([C@]4([C@]([H])(O4)C(C2=C(O)C=C1)=O)[H])OC5=CC=CC6=C5C(O3)=CC=C6
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
>2 years if stored properly
Drug Formulation
To be determined
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:
Palmarumycin C3 is a spirobisnaphthalene fungal metabolite.
In vitro activity:
After addition of 1-hexadecene at 10% to the medium on day 6 of culture, the maximal yields of palmarumycins C2 and C3 were obtained as 0.40 g/L and 1.19 g/L, which were 40.00 fold and 59.50 fold higher, respectively, in comparison with those of the control (0.01 g/L and 0.02 g/L). The results indicated that addition of 1-hexadecene can be an effective strategy for enhancing the production of palmarumycins C2 and C3 in liquid culture of endophytic fungus Berkleasmium sp. Dzf12. Palmarumycin C3 exhibited stronger antimicrobial and antioxidant activities than palmarumycin C2.
Reference: Molecules. 2013 Dec 13;18(12):15587-99. https://pubmed.ncbi.nlm.nih.gov/24352015/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
348.31
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:
Mou Y, Meng J, Fu X, Wang X, Tian J, Wang M, Peng Y, Zhou L. Antimicrobial and antioxidant activities and effect of 1-hexadecene addition on palmarumycin C2 and C3 yields in liquid culture of endophytic fungus Berkleasmium sp. Dzf12. Molecules. 2013 Dec 13;18(12):15587-99. doi: 10.3390/molecules181215587. PMID: 24352015; PMCID: PMC6270283.
In vitro protocol:
Mou Y, Meng J, Fu X, Wang X, Tian J, Wang M, Peng Y, Zhou L. Antimicrobial and antioxidant activities and effect of 1-hexadecene addition on palmarumycin C2 and C3 yields in liquid culture of endophytic fungus Berkleasmium sp. Dzf12. Molecules. 2013 Dec 13;18(12):15587-99. doi: 10.3390/molecules181215587. PMID: 24352015; PMCID: PMC6270283.
1: Mou Y, Meng J, Fu X, Wang X, Tian J, Wang M, Peng Y, Zhou L. Antimicrobial and antioxidant activities and effect of 1-hexadecene addition on palmarumycin C2 and C3 yields in liquid culture of endophytic fungus Berkleasmium sp. Dzf12. Molecules. 2013 Dec 13;18(12):15587-99. doi: 10.3390/molecules181215587. PMID: 24352015; PMCID: PMC6270283.
Krohn, K., Michel, A., Flörke, U., Aust, H. J., Draeger, S., & Schulz, B. (1994). Biologically active metabolites from fungi, 5. Palmarumycins C1–C16 from Coniothyrium sp.: isolation, structure elucidation, and biological activity. Liebigs Annalen der Chemie, 1994(11), 1099-1108.
Hopkins, T. D. (2005). Studies in natural product chemistry: Synthesis of palmarumycin CP1 analogs and total synthesis and structure validation of (+)-bistramide C (Doctoral dissertation, University of Pittsburgh).
