Caldoramide is a pentapeptide[1] isolated from the
cyanobacteriaCaldora penicillata.[2] It has
cytotoxic effects on cancer cells and has been the subject of extensive oncological research.[3] It is structurally analogous to
belamide A and
dolastatin 15. Its appearance is that of a powdery, white, substance.[3]
Structure
The N-terminus for Caldoramide is N,N-dimethylvaline which is attached to a valine which is attached to an N-Me-valine connected to an N-Me-isoleucine which is attached to the C-terminus. The molecule can also be written as N,N-diMe-Val-Val-N-Me-Val-N-Me-Ile-3-O-Me-4-benzylpyrrolinone.[3]
Extraction
Freeze-dried samples of Caldora penicillata had
EtOAc−
MeOH and H2O−
EtOH applied to them in order to extract Caldoramide. The extracts were partitioned with
n-BuOH and H2O and then fractions were taken based on solubility in either EtOAc or BuOH. Caldoramide was extracted from the BuOH soluble fraction.[3]
Pharmacological activity
Caldoramide has been found to be cytotoxic against
HCT116 colorectal cancer cell lines.[3]
^Wunder A, Rothemund M, Schobert R (2018). "Synthesis and anticancer activity of the proposed structure of caldoramide, an N-peptidyltetramate from the cyanobacterium Caldora penicillata". Tetrahedron. 74 (38): 5138–5142.
doi:
10.1016/j.tet.2018.04.004.
S2CID103025376.