cucurbitacin D
19-nor-9-beta,10-alpha-lanosta-5,23-diene-3,11,22-trione, 9-methyl-2-beta,16-alpha,20,25-tetrahydroxy-
Identification
| Name | cucurbitacin D |
| IUPAC | (2S,8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione |
| CAS Number | 3877-86-9 |
| FDA UNII | 5I62H4ORC7 |
| Molecular Formula | C30 H44 O7 |
| Molecular Weight | 516.67508000 |
| MDL Number | MFCD01711333 |
| Nikkaji Number | J8.271F |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 684.00 °C. @ 760.00 mm Hg (est) |
| Flash Point | 719.00 °F. TCC ( 381.40 °C. ) (est) |
| logP (o/w) | 1.480 (est) |
| Soluble in | water, 5.08 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | intravenous-cat LD50 900 ug/kg |
| Dermal Toxicity | subcutaneous-mouse LD50 4600 ug/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | pharmaceuticals / chemical synthisis |
| Recommendation for cucurbitacin D usage levels up to | not for fragrance use. |
| Recommendation for cucurbitacin D flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
cucurbitacine (D)
(2S,8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-
dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
elatericin A
elatericine A
19-nor
lanosta-5,23-diene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (2beta,9beta,10alpha,16alpha,23E)- (9CI)
19-nor-9-beta,10-alpha-
lanosta-5,23-diene-3,11,22-trione, 9-methyl-2-beta,16-alpha,20,25-tetrahydroxy-
PubMed:
Cucurbitacin-D-induced CDK1 mRNA up-regulation causes proliferation arrest of a non-small cell lung carcinoma cell line (NSCLC-N6).
PubMed:
Morphological and physicochemical characterization of liposomes loading cucurbitacin E, an anti-proliferative natural tetracyclic triterpene.
PubMed:
Trichosanthes kirilowii Ethanol Extract and Cucurbitacin D Inhibit Cell Growth and Induce Apoptosis through Inhibition of STAT3 Activity in Breast Cancer Cells.
PubMed:
Cucurbitacin D is a new inflammasome activator in macrophages.
PubMed:
Natural compounds as potential treatments of NF2-deficient schwannoma and meningioma: cucurbitacin D and goyazensolide.
PubMed:
The cucurbitacins E, D and I: investigation of their cytotoxicity toward human chondrosarcoma SW 1353 cell line and their biotransformation in man liver.
PubMed:
Cucurbitacin D induces growth inhibition, cell cycle arrest, and apoptosis in human endometrial and ovarian cancer cells.
PubMed:
[Studies on chemical constituents in roots of Helicteres angustifolia].
PubMed:
Apoptosis induction through proteasome inhibitory activity of cucurbitacin D in human T-cell leukemia.
PubMed:
Cucurbitacin D induces fetal hemoglobin synthesis in K562 cells and human hematopoietic progenitors through activation of p38 pathway and stabilization of the γ-globin mRNA.
PubMed:
Studies toward the total syntheses of cucurbitacins B and D.
PubMed:
New cucurbitane-type triterpenoids from Bryonia aspera.
PubMed:
Interaction of cucurbitacins with human serum albumin: Thermodynamic characteristics and influence on the binding of site specific ligands.
PubMed:
Cucurbitacin D isolated from Trichosanthes kirilowii induces apoptosis in human hepatocellular carcinoma cells in vitro.
PubMed:
Cogniauxia podolaena: bioassay-guided fractionation of defoliated stems, isolation of active compounds, antiplasmodial activity and cytotoxicity.
PubMed:
Phytochemical and biological investigation of Begonia heracleifolia.
PubMed:
Cucurbitane triterpenes from the fruiting bodies and cultivated mycelia of Leucopaxillus gentianeus.
PubMed:
Effect of cucurbitacins on bilirubin-albumin binding in human plasma.
PubMed:
Pregnane, coumarin and lupane derivatives and cytotoxic constituents from Helicteres angustifolia.
PubMed:
[Relationships of Aulacophora beetles feeding behavior with cucurbitacin types in host crops].
PubMed:
A new cucurbitacin D related 16,23-epoxy derivative and its isomerization products.
PubMed:
Inhibition of nitric oxide generation by 23,24-dihydrocucurbitacin D in mouse peritoneal macrophages.
PubMed:
Cytotoxic cucurbitacin constituents from Sloanea zuliaensis.
PubMed:
Cucurbitacins from Trichosanthes kirilowii as the inhibitory components on tyrosinase activity and melanin synthesis of B16/F10 melanoma cells.
PubMed:
Ellagic acid derivatives and cytotoxic cucurbitacins from Elaeocarpus mastersii.
PubMed:
Cucurbitacins are insect steroid hormone antagonists acting at the ecdysteroid receptor.
PubMed:
Cytotoxic constituents ofSorbaria sorbifolia var.stellipila.
PubMed:
Effect of cucurbitacin D on in vitro growth of Xenorhabdus and Photorhabdus spp., symbiotic bacteria of entomopathogenic nematodes.
PubMed:
[Studies on the constituents of "Trichosanthes root". IV. Constituents of roots of Trichosanthes multiloba Miq., Trichosanthes miyagii Hay. and Chinese crude drug "karo-kon"].
PubMed:
[Studies on the constituents of trichosanthes root. III. Constituents of roots of Trichosanthes bracteata Voigt].
PubMed:
[Studies on the constituents of trichosanthes root. I. Constituents of roots of Trichosanthes kirilowii Maxim. var. japonicum Kitam].
PubMed:
Cucurbitacins : Plant-derived defense compounds for diabroticites (Coleoptera: Chrysomelidae).
PubMed:
[Poisoning with a kind of Bitter Edible Gourd].
PubMed:
Pharmaco-dynamic activity of elatericin (cucurbitacin D).