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SML0415

Alantolactone

Name: Alantolactone
Brand: SIGMA

≥98% (HPLC), activin/SMAD3 signaling inducer, powder

Synonym(s):

(+)-Alantolactone., 3aR,5S,8aR,9aR)-3a,5,6,7,8,8a,9,9a-Octahydro-5,8a-dimethyl-3-methylene-naphtho[2,3-b]furan-2(3H)-one, Alant camphor, Elecampane camphor, Eupatal, Inula camphor, NSC 333843, NSC 93131

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₂₀O₂

CAS Number:

546-43-0

Molecular Weight:

232.32

NACRES:

NA.77

PubChem Substance ID:

329825410

UNSPSC Code:

51111800

EC Number:

208-899-3

MDL number:

MFCD00274568

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

Storage condition:

desiccated, protect from light

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Product Name

Alantolactone, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated, protect from light

color

white to beige

solubility

DMSO: 15 mg/mL (clear solution)

storage temp.

−20°C

SMILES string

C[C@H]1CCC[C@]2(C)C[C@H]3OC(=O)C(=C)[C@H]3C=C12

InChI

1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h7,9,11,13H,2,4-6,8H2,1,3H3/t9-,11+,13+,15+/m0/s1

InChI key

PXOYOCNNSUAQNS-AGNJHWRGSA-N

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Bioactive Small Molecules

General description

Alantolactone is a compound produced by Inula helenium. Alantolactone has antibacterial, antifungal, anti-inflammatory and anticancer properties. It suppresses signal transducer and activator of transcription 3 (STAT3) activation in liver and breast cancer cells. Alantolactone induces apoptosis in A549 lung cancer cells.

Application

Alantolactone has been used:

in cell viability assay
to examine the percentage of multicentrosomal mitosis in low and high passage human embryonic stem cells (hESC)
in assessment of degranulation

Biochem/physiol Actions

Alantolactone is a sesquiterpene lactone disrupts the Cripto-1/ActRII complexes, resulting in an induction of activin/SMAD3 signaling. Alantolactone inhibits proliferation in cancer cells with no affect on normal cells.

Alantolactone is an inducer of activin/SMAD3 signaling.

pictograms

GHS07

signalword

Warning

hcodes

H317

pcodes

P261 - P272 - P280 - P302 + P352 - P333 + P313 - P362 + P364

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

0000487851

0000513612

0000451513

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Alantolactone induces activation of apoptosis in human hepatoma cells.

Jia-Chuan Lei et al.

Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 50(9), 3313-3319 (2012-06-23)

Alantolactone, a sesquiterpene lactone, possesses anti-inflammatory property. In this study, we provide evidence that it could be developed as a novel agent against human liver cancer. We observed that alantolactone treatment to HepG2, Bel-7402 and SMMC-7721 cells, human liver cancer

Interactions between the circadian clock and TGF-β signaling pathway in zebrafish.

Hadas E Sloin et al.

PloS one, 13(6), e0199777-e0199777 (2018-06-26)

TGF-β signaling is a cellular pathway that functions in most cells and has been shown to play a role in multiple processes, such as the immune response, cell differentiation and proliferation. Recent evidence suggests a possible interaction between TGF-β signaling

Structure-activity relationship studies on derivatives of eudesmanolides from Inula helenium as toxicants against Aedes aegypti larvae and adults.

Charles L Cantrell et al.

Chemistry & biodiversity, 7(7), 1681-1697 (2010-07-27)

An Aedes aegypti larval toxicity bioassay was performed on compounds representing many classes of natural compounds including polyacetylenes, phytosterols, flavonoids, sesquiterpenoids, and triterpenoids. Among these compounds, two eudesmanolides, alantolactone, and isoalantolactone showed larvicidal activities against Ae. aegypti and, therefore, were

Alantolactone induces apoptosis in glioblastoma cells via GSH depletion, ROS generation, and mitochondrial dysfunction.

Muhammad Khan et al.

IUBMB life, 64(9), 783-794 (2012-07-28)

Glioblastoma multiforme (GBM) is the most malignant and aggressive primary brain tumor in adults. Despite concerted efforts to improve current therapies, the prognosis of glioblastoma remains very poor. Alantolactone, a sesquiterpene lactone compound, has been reported to exhibit antifungal, antibacteria

Sesquiterpene lactone contact sensitivity: clinical patterns of Compositae dermatitis and relationship to chronic actinic dermatitis.

J S Ross et al.

Contact dermatitis, 29(2), 84-87 (1993-08-01)

A mix of 3 sesquiterpene lactones (SL) (SL mix 0.1%) was evaluated over a 4-year period. Of 7420 patients with eczema investigated by patch testing, 135 (68 male, 67 female) (1.8%) demonstrated positive reactions, 114 (84%) considered clinically relevant. Females

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Global Trade Item Number

SKU	GTIN
SML0415-25MG	04061833222720
SML0415-5MG	04061833222737

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