A chemical investigation of the trepang (stychopus Japonicus Selenka): The structure of triterpenoid aglycones obtained from trepang glycosides.

Elyakov, G. B.; Кузнецова, Т. А.; Dzizenko, A. K.; El’kin, Yu. N.

doi:10.1016/s0040-4039(01)87826-6

Cited by 22 publications

(7 citation statements)

References 4 publications

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“…They also have been employed for various medicinal purposes for hundreds of years. Sea cucumber toxins or holotoxins have been isolated in crystalline form and shown to contain a mixture of saponins 70–72 . Some glycosylated triterpenoid saponins have been shown to possess anticancer activity 73–78 .…”

Section: Introductionmentioning

confidence: 99%

Review of the Apoptosis Pathways in Pancreatic Cancer and the Anti‐apoptotic Effects of the Novel Sea Cucumber Compound, Frondoside A

Roginsky

Ding

et al. 2008

Annals of the New York Academy of Sciences

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Pancreatic cancer cells are resistant to the growth-inhibitory and apoptosis-inducing effects of conventional chemotherapeutic agents. There are multiple genetic and epigenetic events during the process of carcinogenesis that enable the cancer cells to avoid normal growth constraints and apoptosis. Investigation of the mechanisms involved has led to multiple strategies that encourage cell death and apoptosis to occur. The pathways involved are summarized in this review, together with some recently developed strategies to promote cell death in this cancer and with a particular focus on the frondoside A, a novel triterpenoid glycoside isolated from the Atlantic sea cucumber, Cucumaria frondosa. Frondoside A inhibited proliferation of AsPC-1 human pancreatic cancer cells in a concentration- and time-dependent manner, as measured by (3)H-thymidine incorporation and cell counting. In concert with inhibition of cell growth, frondoside A induced significant morphological changes consistent with apoptosis. Propidium iodide DNA staining showed an increase of sub-G0/G1 cell population of apoptotic cells induced by frondoside A. Frondoside A-induced apoptosis was confirmed by annexin V binding and TUNEL assay. Furthermore, western blotting showed a decrease in expression of Bcl-2 and Mcl-1, an increase in Bax expression, activation of caspases 3, 7, and 9, and an increase in the expression of the cyclin-dependent kinase inhibitor, p21. These findings show that frondoside A induced apoptosis in human pancreatic cancer cells through the mitochondrial pathway and activation of the caspase cascade. Finally, a very low concentration of frondoside A (10 mug/kg/day) inhibited growth of AsPC-1 xenografts in athymic mice. In conclusion, new chemotherapeutic agents are desperately needed for pancreatic cancer because of the poor responsiveness to currently available treatment options. Frondoside A has potent growth inhibitory effects on human pancreatic cancer cells, and the inhibition of proliferation is accompanied by marked apoptosis. Frondoside A may be valuable for the treatment or chemoprevention of this devastating disease.

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Section: Introductionmentioning

confidence: 99%

Review of the Apoptosis Pathways in Pancreatic Cancer and the Anti‐apoptotic Effects of the Novel Sea Cucumber Compound, Frondoside A

Roginsky

Ding

et al. 2008

Annals of the New York Academy of Sciences

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“…In the methanolic extracts of the Far-Eastern Sea cucumber, the trepang (Stychop#s japonicus Selenka) (84) OH absence of the heteroanular diene system and its replacement by unsaturation at L1 5 • 6 and L1 8 • 9 and, in stichopogenin A 2, the presence of a double bond at C-24 and absence of a C-25 tertiary hydroxyl.…”

Section: Homentioning

confidence: 99%

“…Other Laurencia species (e. g. L. Okamurai Yamada} (ISJ, ISJa) have also yielded aplysin (103), aplysinol (104), debromoaplysin {n8}, and debromolaurinterol (84).…”

Section: (74 C)mentioning

confidence: 99%

Chemistry of Natural Products Derived from Marine Sources

Premuzic

1971

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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“…The original procedure,28 modified to include fast addition of the bromine and ice-water quench after five min, affords a quantitative yield of a 1:1 mixture of 6 and 7. (25fi)-5a-Spirost-23-ene (8).-To a stirred solution in a N2 atmosphere of 23fi-bromo-(25fi)-5a-spirostan (6, 262 mg, 0.546 mmol) in dry benzene (25 ml) and DMSO (18.7 ml) was added (73) Melting points were uncorrected and were determined on the Kofler block except for those labeled "vac" which were run in sealed, evacuated tubes. The infrared spectra were determined in chloroform, unless otherwise noted, on a Perkin-Elmer 421 grating spectrophotometer using sodium chloride cavity cells.…”

Section: Experimental Section73mentioning

confidence: 99%

Side-chain transformations and deuterium labeling in the steroidal sapogenin series

Faul¹,

Failli²,

Djerassi³

1970

J. Org. Chem.

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A chemical investigation of the trepang (stychopus Japonicus Selenka): The structure of triterpenoid aglycones obtained from trepang glycosides.

Cited by 22 publications

References 4 publications

Review of the Apoptosis Pathways in Pancreatic Cancer and the Anti‐apoptotic Effects of the Novel Sea Cucumber Compound, Frondoside A

Review of the Apoptosis Pathways in Pancreatic Cancer and the Anti‐apoptotic Effects of the Novel Sea Cucumber Compound, Frondoside A

Chemistry of Natural Products Derived from Marine Sources

Side-chain transformations and deuterium labeling in the steroidal sapogenin series

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