Loliolide (Synonyms: Loliolid; Digiprolactone)

Name: Loliolide
Brand: MedChemExpress
SKU: HY-118020A
Rating: 4.5 (0 reviews)

Cat. No.: HY-118020A Purity: 99.92%: Data Sheet
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Loliolide (Loliolid) is a β-carotene metabolite. Loliolide reduces caspase 3, 8, 9 expression, enhances PI3K, AKT, SIRT1, inhibits ROS, apoptosis, and blocks NF-κB p65 nuclear translocation. Loliolide protects mitochondria, reduces oxidative stress, and increases cell viability in neuroblastoma cells. Loliolide can be used for the research of UV-induced skin damage and Parkinson’s disease.

For research use only. We do not sell to patients.

Loliolide Chemical Structure

CAS No. : 5989-02-6

Size	Stock	Quantity
1 mg	In-stock	Estimated Time of Arrival: December 31
5 mg	In-stock	Estimated Time of Arrival: December 31
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Caspase 1 Caspase 2 Caspase 3 Caspase 4 Caspase 5 Caspase 6 Caspase 7 Caspase 8 Caspase 9 Caspase 10 Caspase 12 Caspase Caspase 11 Caspase-13

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PI3Kα PI3Kβ PI3Kγ PI3Kδ PI3KC2α PI3KC2β PI3KC2γ Vps34 PI3K PI3KC3 p120γ

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Akt Akt1 Akt2 Akt3

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Sirtuin SIRT1 SIRT2 SIRT3 SIRT6 SIRT5 SIRT7 SIRT4

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NF-κB NF-κB1/p50 RelA/p65 RelB c-Rel

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MMP-1 MMP-2 MMP-3 MMP-8 MMP-9 MMP-13 MMP-14 MMP-17 ADAM10 ADAM17 MMP-7 MMP-12 MMP-10 MMP ADAM8 MMP-19

Biological Activity
Purity & Documentation
References
Customer Review

Description

IC₅₀ & Target^[1]

SIRT1

MMP-9

Caspase 3

Caspase 8

Caspase 9

Cellular Effect

Cell Line	Type	Value	Description	References
A549	IC₅₀	> 10 μM Compound: 19	Antiproliferative activity against human A549 cells assessed as reduction in cell viability after 72 hrs by SRB assay Antiproliferative activity against human A549 cells assessed as reduction in cell viability after 72 hrs by SRB assay	[PMID: 32946697]
HT-29	IC₅₀	> 10 μM Compound: S11	Cytotoxicity against human HT-29 cells assessed as reduction in cell viability after 72 hrs by CellTiter 96 aqueous one solution assay Cytotoxicity against human HT-29 cells assessed as reduction in cell viability after 72 hrs by CellTiter 96 aqueous one solution assay	[PMID: 30057155]
HT-29	IC₅₀	> 10 μM Compound: S11	Inhibition of mitochondrial membrane potential in human HT-29 cells after 3 hrs by JC-1 staining based fluorescence assay Inhibition of mitochondrial membrane potential in human HT-29 cells after 3 hrs by JC-1 staining based fluorescence assay	[PMID: 30057155]
HepG2	IC₅₀	> 20 μg/mL Compound: loliolide	Growth inhibition of HepG2 cells Growth inhibition of HepG2 cells	[PMID: 17547458]
KB	IC₅₀	> 10 μM Compound: 19	Antiproliferative activity against human KB cells assessed as reduction in cell viability after 72 hrs by SRB assay Antiproliferative activity against human KB cells assessed as reduction in cell viability after 72 hrs by SRB assay	[PMID: 32946697]
MCF7	IC₅₀	> 10 μM Compound: 19	Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by SRB assay Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by SRB assay	[PMID: 32946697]
MDA-MB-231	IC₅₀	> 10 μM Compound: 19	Antiproliferative activity against human MDA-MB-231 cells assessed as reduction in cell viability after 72 hrs by SRB assay Antiproliferative activity against human MDA-MB-231 cells assessed as reduction in cell viability after 72 hrs by SRB assay	[PMID: 32946697]
MDA-MB-231	IC₅₀	> 10 μM Compound: S11	Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability after 72 hrs by CellTiter 96 aqueous one solution assay Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability after 72 hrs by CellTiter 96 aqueous one solution assay	[PMID: 30057155]
MDA-MB-435	IC₅₀	> 10 μM Compound: S11	Cytotoxicity against human MDA-MB-435 cells assessed as reduction in cell viability after 72 hrs by CellTiter 96 aqueous one solution assay Cytotoxicity against human MDA-MB-435 cells assessed as reduction in cell viability after 72 hrs by CellTiter 96 aqueous one solution assay	[PMID: 30057155]
OVCAR-3	IC₅₀	> 10 μM Compound: S11	Cytotoxicity against human OVCAR3 cells assessed as reduction in cell viability after 72 hrs by CellTiter 96 aqueous one solution assay Cytotoxicity against human OVCAR3 cells assessed as reduction in cell viability after 72 hrs by CellTiter 96 aqueous one solution assay	[PMID: 30057155]
RAW264.7	CC₅₀	> 100 μM Compound: 11	Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viability measured after 24 hrs by MTT assay Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viability measured after 24 hrs by MTT assay	[PMID: 33667099]
RAW264.7	IC₅₀	56.7 μM Compound: 11	Inhibition of LPS induced NO production in mouse RAW264.7 cells measured after 24 hrs by Griess reagent based assay Inhibition of LPS induced NO production in mouse RAW264.7 cells measured after 24 hrs by Griess reagent based assay	[PMID: 33667099]
RAW264.7	IC₅₀	> 0.4 μM Compound: loliolide	Antiinflammatory activity against mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide release after 24 hrs Antiinflammatory activity against mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide release after 24 hrs	[PMID: 20192236]
RAW264.7	IC₅₀	> 50 μM Compound: 11	Inhibition of LPS-induced IL-1beta production in mouse RAW264.7 cells after 24 hrs by ELISA Inhibition of LPS-induced IL-1beta production in mouse RAW264.7 cells after 24 hrs by ELISA	[PMID: 24963714]
RAW264.7	IC₅₀	> 50 μM Compound: 11	Inhibition of LPS-induced NO production in mouse RAW264.7 cells after 24 hrs by Griess reagent based assay Inhibition of LPS-induced NO production in mouse RAW264.7 cells after 24 hrs by Griess reagent based assay	[PMID: 24963714]
WI-38	IC₅₀	> 20 μg/mL Compound: loliolide	Growth inhibition of WI38 cells Growth inhibition of WI38 cells	[PMID: 17547458]
WI-38 VA13	IC₅₀	> 20 μg/mL Compound: loliolide	Growth inhibition of VA13 cells Growth inhibition of VA13 cells	[PMID: 17547458]

In Vitro

Loliolide (25-100 μM; 24 h) is non-toxic to HaCaT human keratinocytes at concentrations up to 100 μM and dose-dependently recovers UVB-reduced HaCaT cell viability^[1].
Loliolide (25-100 μM; 24 h) dose-dependently inhibits UVB-induced reactive oxygen species generation and DNA damage in HaCaT cells^[1].
Loliolide (50-100 μM; 24 h) reduces UVB-induced apoptosis in HaCaT cells^[1].
Loliolide (25-100 μM; 24 h) dose-dependently inhibits UVB-induced activation of caspase 3, 8, and 9 to reduce apoptosis in HaCaT cells^[1].
Loliolide (25-200 μM; 24 h) dose-dependently inhibits UVB-induced MMP-1, MMP-2, MMP-3, and MMP-9 expression and restores UVB-reduced SIRT1 expression in HaCaT cells^[1].
Loliolide (100 μM; 8-24 h) significantly accelerates scratch wound closure via increased cell migration in HaCaT cells^[1].
Loliolide (25-100 μM; 24-72 h) dose-dependently increases proliferation in HaCaT cells^[1].
Loliolide (25-100 μM; 24 h) dose-dependently upregulates migration factors, growth factor KGF, and wound-healing cytokines, while downregulating inflammation-related genes in scratched HaCaT cells^[1].
Loliolide (25-100 μM; 24 h) dose-dependently activates the PI3K/AKT EGFR signaling pathway in scratched HaCaT human keratinocytes, with maximum activity at 100 μM^[1].
Loliolide (1-100 μM; 24 h) exhibits no cytotoxicity and inhibits 6-hydroxydopamin (6-OHDA)-induced cytotoxicity in SH-SY5Y cells^[2].
Loliolide (50-100 μM; 6 h) reduces 6-OHDA-induced ROS production and Caspase-3 activity, stimulates catalase activity, prevents 6-OHDA-induced mitochondrial membrane depolarization in SH-SY5Y cells^[2].
Loliolide (50-100 μM; 24 h) prevents 6-OHDA-induced nuclear fragmentation and condensation in SH-SY5Y cells^[2].
Loliolide (50-100 μM; 6 h) inhibits 6-OHDA-induced NF-κB p65 translocation from the cytoplasm to the nucleus in SH-SY5Y cells^[2].
Loliolide (50-100 μM; 24 h) is non-cytotoxic to RAW 264.7 cells and does not induce NO production in RAW 264.7 cells^[2].
Loliolide (50-100 μM; 24 h) reduces LPS-induced NO production and reduces LPS (HY-D1056)-induced production of TNF-α and IL-6 in RAW 264.7 cells^[2].
Loliolide (300 μM; 24 h leaf treatment, 5 d mite incubation) reduces the survival rate of Tetranychus urticae and egg deposition in Solanum lycopersicum cv. Micro-Tom leaves ^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Viability Assay^[1]

Cell Line:	HaCaT cells
Concentration:	25; 50; 100 μM
Incubation Time:	24 h
Result:	Showed no effect on HaCaT cell viability at concentrations up to 100 μM under normal culture conditions. Recovered UVB-reduced cell viability in a dose-dependent manner, with 100 μM producing the strongest statistically significant recovery.

Western Blot Analysis^[1]

Cell Line:	HaCaT cells
Concentration:	25; 50; 100 μM
Incubation Time:	24 h
Result:	Dose-dependently reduced UVB-induced expression of cleaved caspase 3, 8, and 9 in HaCaT cells. Dose-dependently increased phosphorylation of PI3K and AKT in scratched HaCaT cells. Showed the strongest activation at 100 μM, while total PI3K and AKT levels remained unchanged.

RT-PCR^[1]

Cell Line:	HaCaT cells
Concentration:	25; 50; 100; 200 μM
Incubation Time:	24 h
Result:	Dose-dependently reduced UVB-induced mRNA expression of MMP-1, MMP-2, MMP-3, and MMP-9 in HaCaT cells. Restored UVB-reduced SIRT1 mRNA expression in HaCaT cells. Dose-dependently increased mRNA expression of migration factors K6, K16, K17, growth factor KGF, and cytokines IL-1, IL-17, IL-22 in scratched HaCaT cells. Dose-dependently reduced mRNA expression of inflammation-related genes TNF-α and MMP-1 in scratched HaCaT cells.

Cell Migration Assay ^[1]

Cell Line:	HaCaT cells
Concentration:	25; 50; 100 μM
Incubation Time:	8, 16, 24 h
Result:	Significantly increased HaCaT cell migration and scratch wound closure at 8, 16, and 24 h post-scratching. Showed statistically significant differences (p<0.01 compared to untreated scratched control) at all time points.

Cell Proliferation Assay^[1]

Cell Line:	HaCaT cells
Concentration:	25-100 μM
Incubation Time:	24, 48, 72 h
Result:	Dose-dependently increased HaCaT cell proliferation over 72 h. Produced statistically significant increases at 72 h for all concentrations, and at 48 h for 100 μM.

Cell Viability Assay^[2]

Cell Line:	SH-SY5Y cells
Concentration:	1; 5; 10; 50;100 μM
Incubation Time:	24 h
Result:	Did not induce cytotoxicity at any tested concentration. Showed cell viability remained close to vehicle control levels.\nIncreased cell viability by 23.70% at 50 μM and 41.06% at 100 μM.

Western Blot Analysis^[2]

Cell Line:	SH-SY5Y cells
Concentration:	50; 100 μM
Incubation Time:	6 h
Result:	Downregulated nuclear NF-κB p65 and upregulated cytosolic levels, with significant inhibition of translocation observed at 100 μM compared to cells treated with 6-OHDA alone.

ELISA Assay^[2]

Cell Line:	RAW 264.7 murine macrophage cells
Concentration:	50; 100 μM
Incubation Time:	24 h
Result:	Reduced TNF-α production by 305% at 50 μM and 238% at 100 μM. Reduced IL-6 production by 197% at 50 μM and 220% at 100 μM compared to cells stimulated with LPS alone. Did not significantly affect IL-10 levels.

Apoptosis Analysis^[1]

Cell Line:	HaCaT cells
Concentration:	50; 100 μM
Incubation Time:	24 h
Result:	Reduced UVB-induced apoptosis in HaCaT cells. Showed stronger activity at 100 μM than 50 μM.

Molecular Weight

196.24

Formula

C₁₁H₁₆O₃

CAS No.

5989-02-6

Appearance

Solid

Color

White to off-white

SMILES

C[C@]12C(C(C)(C[C@@H](C1)O)C)=CC(O2)=O

Structure Classification

Others

Initial Source

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

4°C, protect from light

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Solvent & Solubility

In Vitro:

Methanol : 58.87 mg/mL (299.99 mM; Need ultrasonic and warming)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	5.0958 mL	25.4790 mL	50.9580 mL
5 mM	1.0192 mL	5.0958 mL	10.1916 mL
10 mM	0.5096 mL	2.5479 mL	5.0958 mL

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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Purity & Documentation

Purity: 99.92%

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Data Sheet (285 KB) SDS (394 KB)

COA (249 KB) HNMR (216 KB) LCMS (96 KB)

Handling Instructions (2659 KB)

References

[1]. Park SH, et al. Loliolide Presents Antiapoptosis and Antiscratching Effects in Human Keratinocytes. Int J Mol Sci. 2019;20(3):651. Published 2019 Feb 2.

[2]. Silva J, et al. Loliolide, a New Therapeutic Option for Neurological Diseases? In Vitro Neuroprotective and Anti-Inflammatory Activities of a Monoterpenoid Lactone Isolated from Codium tomentosum. Int J Mol Sci. 2021;22(4):1888. Published 2021 Feb 14.

[3]. Murata M, et al. Loliolide, a Carotenoid Metabolite, Is a Potential Endogenous Inducer of Herbivore Resistance. Plant Physiol. 2019;179(4):1822-1833. [Content Brief]

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

Methanol	1 mM	5.0958 mL	25.4790 mL	50.9580 mL	127.3950 mL
	5 mM	1.0192 mL	5.0958 mL	10.1916 mL	25.4790 mL
	10 mM	0.5096 mL	2.5479 mL	5.0958 mL	12.7395 mL
	15 mM	0.3397 mL	1.6986 mL	3.3972 mL	8.4930 mL
	20 mM	0.2548 mL	1.2740 mL	2.5479 mL	6.3698 mL
	25 mM	0.2038 mL	1.0192 mL	2.0383 mL	5.0958 mL
	30 mM	0.1699 mL	0.8493 mL	1.6986 mL	4.2465 mL
	40 mM	0.1274 mL	0.6370 mL	1.2740 mL	3.1849 mL
	50 mM	0.1019 mL	0.5096 mL	1.0192 mL	2.5479 mL
	60 mM	0.0849 mL	0.4247 mL	0.8493 mL	2.1233 mL
	80 mM	0.0637 mL	0.3185 mL	0.6370 mL	1.5924 mL
	100 mM	0.0510 mL	0.2548 mL	0.5096 mL	1.2740 mL

Loliolide Related Classifications

Help & FAQs

Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

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Loliolide (Synonyms: Loliolid; Digiprolactone)

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