Heliantriol B2
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| Category | Bioactive by-products |
| Catalog number | BBF-05488 |
| CAS | 61229-18-3 |
| Molecular Weight | 458.71 |
| Molecular Formula | C30H50O3 |
| Purity | 98% |
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Description
Heliantriol B2 is a natural compound which can be isolated from Chuquiraga erinacea and Monteverdia apurimacensis, etc.
Specification
| Synonyms | Lup-20(29)-ene-3,16,28-triol |
| Storage | Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years) |
| IUPAC Name | 3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-4,9-diol |
| Canonical SMILES | CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)O)C)CO |
| InChI | InChI=1S/C30H50O3/c1-18(2)19-10-15-30(17-31)24(33)16-29(7)20(25(19)30)8-9-22-27(5)13-12-23(32)26(3,4)21(27)11-14-28(22,29)6/h19-25,31-33H,1,8-17H2,2-7H3 |
| InChI Key | TWKNDDJHVQUEJF-UHFFFAOYSA-N |
Properties
| Appearance | Crystal |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 552.9°C at 760 mmHg |
| Melting Point | 300-301°C |
| Density | 1.061 g/cm3 |
| Solubility | Soluble in Chloroform, DMSO, Methanol |
Reference Reading
1. Lupane Triterpenoids and New Derivatives as Antiproliferative Agents Against Prostate Cancer Cells
María Julia Castro, Valeria Pilar Careaga, Paula Alejandra Sacca, María Belén Faraoni, Ana Paula Murray, Juan Carlos Calvo Anticancer Res. 2019 Jul;39(7):3835-3845. doi: 10.21873/anticanres.13533.
Background/aim: This study examined the potential role of natural triterpenoids lupeol, calenduladiol and heliantriol B2, and a set of 19 derivatives, as antiproliferative and antimetastatic agents against prostate cancer cells. Materials and methods: Natural triterpenoids were isolated from Chuqiraga erinaceae. Analogs were obtained by transformations of lupeol and calenduladiol. The effects of compounds on PC-3 and LNCaP cells were determined using the MTT assay. Compounds with half-maximal inhibitory concentration <70 μM were evaluated as antimetastatic agents by a wound-healing assay. Results: Lupeol-3β-sulfate, a new semisynthetic lupane, was the most active compound. In general, sulfated derivatives displayed higher activity than the lead against both cell lines. A new analog, calenduladiol-3β-monosulfate, inhibited the migration of PC-3 cells; heliantriol B2 and 3β-aminolupane inhibited the migration of LNCaP cells in a concentration-dependent manner. Conclusion: Our study provides novel agents with cytotoxic effects on prostate cancer cells, which may represent a potential new therapeutic approach for prostate cancer.
2. Cytotoxic effects induced by combination of heliantriol B2 and dequalinium against human leukemic cell lines
M Soledad Vela Gurovic, A María Díaz Lanza, María del Carmen Boyano Adánez, M Cristina Estañ Omaña, Irene Gañán Gómez, A Paula Murray, Pilar Sancho López Phytother Res. 2011 Apr;25(4):603-10. doi: 10.1002/ptr.3310. Epub 2010 Oct 26.
Natural occurring compounds are considered an important source of antitumoral agents. In the present study, the cytotoxic potential of three pentacyclic triterpenes isolated from Chuquiraga erinacea (Asteraceae), against the human leukemic cell lines NB4 and K562 was assessed. Heliantriol B2 (HB2) showed the highest cytotoxic activity after 24 h treatment showing IC(50) values of 1.98 ± 0.12 µm and 3.52 ± 0.14 µm for NB4 and K562 cells, respectively. This activity was higher than that of the reference compound dequalinium (DQA). Apoptosis and necrosis induced by HB2 in both NB4 and K562 cell lines were analysed by Annexin V/PI labeling. Mitochondrial alterations including reactive oxygen species (ROS) production and mitochondrial transmembrane potential (ΔΨm) were also tested. The results demonstrated that HB2 induced cell death by apoptosis and necrosis and showed enhanced cytotoxic effects in combination with DQA. Besides, HB2 induced ROS overproduction in NB4 cells and a slight decrease of ΔΨm. Consequently, our findings prompt further studies on the HB2 mechanism of action and its selectivity to tumor cells in order to assess the potential of HB2 as an agent for cancer treatment.
3. Triterpenoids with acetylcholinesterase inhibition from Chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae)
María Soledad Gurovic, María Julia Castro, Victoria Richmond, María Belén Faraoni, Marta S Maier, Ana Paula Murray Planta Med. 2010 Apr;76(6):607-10. doi: 10.1055/s-0029-1240582. Epub 2009 Nov 16.
A bioactivity-guided approach was taken to identify the acetylcholinesterase (AChE) inhibitory agents in the ethanolic extract of Chuquiraga erinacea D. Don. subsp. erinacea leaves using a bioautographic method. This permitted the isolation of the pentacyclic triterpenes calenduladiol (1), faradiol (2), heliantriol B2 (3), lupeol (4), and a mixture of alpha-and beta-amyrin ( 5A and 5B) as active constituents. Pseudotaraxasterol (6) and taraxasterol (7) were also isolated from this extract and showed no activity at the same analytical conditions. Compound 1 showed the highest AChE inhibitory activity with 31.2 % of inhibition at 0.5 mM. Looking forward to improve the water solubility of the active compounds, the sodium sulfate ester of 1 was prepared by reaction with the (CH3)3N.SO3 complex. The semisynthetic derivative disodium calenduladiol disulfate (8) elicited higher AChE inhibition than 1 with 94.1 % of inhibition at 0.5 mM (IC (50) = 0.190 +/- 0.003 mM). Compounds 1, 2, 3, 5, 6, and 7 are reported here for the first time in C. erinacea. This is the first report of AChE inhibition from calenduladiol (1) as well as from a sulfate derived from a natural product.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
