A triterpenoid saponin isolated from the sea cucumber Cucumaria frondosawith anticancer properties
- Catalog No: APH-05021
- CAS Number: 127367-76-4 (anhydrous)
- Chemical Formula: C60H95NaO29S
- Molecular Weight: 1335.44
- Purity: > 98 % CP
- Appearance: White crystalline solid
- Solubility: Soluble in water
- Stability: Stable as a solid over extended period at -20ºC
- Storage: Store at room temperature
- Shipping: On ice (5ºC)
- Handling: Avoid exposure to oxygen and direct sunlight
Frondoside A, a triterpenoid saponin with a sugar-steroid structure, is derived from the orange-footed sea cucumber, Cucumaria frondosa (Li et al., 2008). C. frondosa is the most common sea cucumber in New England, but it is abundant in the North Atlantic Ocean and Russia’s Barents Sea. Most cultures in East and Southeast Asia regard both fresh and dried sea cucumber (and their sex organs) as a delicacy.
At Aphios®, extraction and purification of this compound is performed using extraction of sea cucumber, after it is harvested for its culinary components, followed by segmentation chromatography.
Frondoside A is of interest as a potential anticancer agent (Li et al., 2008). It has potent cytotoxicity against THP-1 and HeLa tumor cell lines with IC50 values of 4.5 µg/mL and 2.1 µg/mL, respectively (Silchenko et al., 2008). It has been shown to inhibit proliferation and induces apoptosis of human pancreatic cancer xenografts (Li et al., 2008). It has also inhibited the migration and invasion of breast cancer cell line MDA-MB-231 in vitro (Al Marzouqi et al., 2011).
Additionally, Frondoside A strongly decreased the growth of MDA-MB-231 tumor xenografts in athymic mice without any toxic side effects (Al Marzouqi et al., 2011). Another study performed by Ma et al. (2011) has shown that Frondoside A has potent anti-metastatic activity. The glycoside inhibited tumor metastasis in a murine model of metastatic breast cancer, and its mechanism of action is partially attributed to its ability to antagonize prostaglandin E receptors EP4 and EP2 (Ma et al., 2011). All these studies support Frondoside A as a promising novel therapeutic cancer agent.
Al Marzouqi N, Iratni R, Nemmar A, Arafat K, Ahmed Al Sultan M, Yasin J, Collin P, Mester J, Adrian T and Attoub S. (2011). Frondoside A inhibits human breast cancer cell survival, migration, invasion and the growth of breast tumor xenografts. Eur J Pharmacol. 668: 25-34.
Li X, Roginsky A, Ding X, Woodward C, Collin P, Newman R, Bell R and Adrian T. (2008). Review of the apoptosis pathways in pancreatic cancer and the anti-apoptotic effects of the novel sea cucumber compound, Frondoside A. Ann N Y Acad Sci. 1138: 181-198.
Ma X, Kundu N, Collin P, Goloubeva O and Fulton A. (2011). Frondoside A inhibits breast cancer metastasis and antagonizes prostaglandin E receptors EP4 and EP2. Breast Cancer Res Treat. DOI: 10.1007/s10549-011-1675-z.
Silchenko A, Avilov S, Kalinin V, Kalinovsky A, Dmitrenok P, Fedorov S, Stepanov V, Dong Z and Stonik V. (2008). Constituents of the sea cucumber Cucumaria okhotensis. Structures of okhotosides B1-B3 and cytotoxic activities of some glycosides from this species. J Nat Prod. 71: 351-356.