Loliolide | CAS#1133-03-5 | Diverse monoterpene lactone

MedKoo Cat#: 599164 | Name: Loliolide

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Loliolide is a monoterpene lactone that has been found in P. urinaria and has diverse biological activities. It scavenges DPPH and peroxide radicals in cell-free assays when used at concentrations ranging from 62.5 to 250 µM and reduces peroxide-induced apoptosis in Vero cells. Loliolide (10 µg/ml) inhibits LPS-induced proliferation of isolated mouse T and B cells. It reduces hepatitis C virus (HCV) infectivity in Huh7.5 cells (EC50 = 2.48 µM) and inhibits HCV binding to Huh7.5 cells when used at concentrations of 10 and 50 µM. Loliolide also increases A. cephalotes preference for control flakes when applied to test flakes at a concentration of 6.8 mg/g of rye, indicating insect repellent activity.

Chemical Structure

Loliolide

CAS#1133-03-5

Theoretical Analysis

MedKoo Cat#: 599164

Name: Loliolide

CAS#: 1133-03-5

Chemical Formula: C11H16O3

Exact Mass: 196.1099

Molecular Weight: 196.25

Elemental Analysis: C, 67.32; H, 8.22; O, 24.46

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 665.00	2 Weeks

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Related CAS #

1133-03-5 5989-02-6

Synonym

Loliolide; (–)-Loliolide; (–) Loliolide; NSC 289632; NSC-289632; NSC289632;

IUPAC/Chemical Name

(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one

InChi Key

XEVQXKKKAVVSMW-WRWORJQWSA-N

InChi Code

InChI=1S/C11H16O3/c1-10(2)5-7(12)6-11(3)8(10)4-9(13)14-11/h4,7,12H,5-6H2,1-3H3/t7-,11+/m0/s1

SMILES Code

O[C@@H](CC1(C)C)C[C@](O2)(C)C1=CC2=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Loliolide is a monoterpene lactone that has been found in P. urinaria and has diverse biological activities.

In vitro activity:

The results showed that (-)-loliolide improved the cell viability by reducing the production of intracellular reactive oxygen species (ROS) in IFN-γ/TNF-α-stimulated HaCaT keratinocytes. In addition, (-)-loliolide effectively decreased the expression of inflammatory cytokines (interleukin (IL)-4 IL-6, IL-13, IFN-γ and TNF-α) and chemokines (CCL11 (Eotaxin), macrophage-derived chemokine (MDC), regulated on activation, normal T cell expressed and secreted (RANTES), and thymus and activation-regulated chemokine (TARC)), by downregulating the expression of epidermal-derived initial cytokines (IL-25, IL-33 and thymic stromal lymphopoietin (TSLP)). Reference: Antioxidants (Basel). 2021 May 27;10(6):856. https://pubmed.ncbi.nlm.nih.gov/34071797/

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 196.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Han EJ, Fernando IPS, Kim HS, Lee DS, Kim A, Je JG, Seo MJ, Jee YH, Jeon YJ, Kim SY, Ahn G. (-)-Loliolide Isolated from Sargassum horneri Suppressed Oxidative Stress and Inflammation by Activating Nrf2/HO-1 Signaling in IFN-γ/TNF-α-Stimulated HaCaT Keratinocytes. Antioxidants (Basel). 2021 May 27;10(6):856. doi: 10.3390/antiox10060856. PMID: 34071797; PMCID: PMC8229944. 2. Fernando IPS, Dias MKHM, Madusanka DMD, Kim HS, Han EJ, Kim MJ, Seo MJ, Ahn G. Effects of (-)-Loliolide against Fine Dust Preconditioned Keratinocyte Media-Induced Dermal Fibroblast Inflammation. Antioxidants (Basel). 2021 Apr 26;10(5):675. doi: 10.3390/antiox10050675. PMID: 33925954; PMCID: PMC8144948.

In vitro protocol:

In vivo protocol:

TBD

1: Han EJ, Fernando IPS, Kim HS, Lee DS, Kim A, Je JG, Seo MJ, Jee YH, Jeon YJ, Kim SY, Ahn G. (-)-Loliolide Isolated from Sargassum horneri Suppressed Oxidative Stress and Inflammation by Activating Nrf2/HO-1 Signaling in IFN-γ/TNF-α-Stimulated HaCaT Keratinocytes. Antioxidants (Basel). 2021 May 27;10(6):856. doi: 10.3390/antiox10060856. PMID: 34071797. 2: Lee D, Kim KH, Jang TS, Kang KS. Identification of bioactive compounds from mulberry enhancing glucose-stimulated insulin secretion. Bioorg Med Chem Lett. 2021 Jul 1;43:128096. doi: 10.1016/j.bmcl.2021.128096. Epub 2021 May 10. PMID: 33984475. 3: Castrosanto MA, Alvarez MR, Salamanez KC, Nacario RC, Completo GC. Barnyard grass [Echinochloa crus-galli (L.) Beauv] leaves extract against tomato pests. J Sci Food Agric. 2021 May 9. doi: 10.1002/jsfa.11298. Epub ahead of print. PMID: 33966279. 4: Uddin Chy MN, Adnan M, Chowdhury MR, Pagano E, Kamal ATMM, Oh KK, Cho DH, Capasso R. Central and peripheral pain intervention by Ophiorrhizarugosa leaves: Potential underlying mechanisms and insight into the role of pain modulators. J Ethnopharmacol. 2021 Aug 10;276:114182. doi: 10.1016/j.jep.2021.114182. Epub 2021 May 5. PMID: 33964360. 5: Xu W, Wang J, Ju B, Lan X, Ying X, Stien D. Seven compounds from Portulaca oleracea L. and their anticholinesterase activities. Nat Prod Res. 2021 Apr 30:1-7. doi: 10.1080/14786419.2021.1916928. Epub ahead of print. PMID: 33926330. 6: Fernando IPS, Dias MKHM, Madusanka DMD, Kim HS, Han EJ, Kim MJ, Seo MJ, Ahn G. Effects of (-)-Loliolide against Fine Dust Preconditioned Keratinocyte Media- Induced Dermal Fibroblast Inflammation. Antioxidants (Basel). 2021 Apr 26;10(5):675. doi: 10.3390/antiox10050675. PMID: 33925954; PMCID: PMC8144948. 7: Chi H, Qi X, Wang X, Wang Y, Han X, Wang J, Wang H. Preparative separation and purification of loliolide and epiloliolide from Ascophyllum nodosum using amine-based microporous organic polymer for solid phase extraction coupled with macroporous resin and prep-HPLC. Anal Methods. 2021 Apr 28;13(16):1939-1944. doi: 10.1039/d1ay00186h. Epub 2021 Apr 8. PMID: 33913944. 8: Vingre da Silva Mota G, Costa FLP. A theoretical study to the loliolide molecule and its isomers: a study by circular dichroism, QTAIM, and NMR theoretical methods. J Mol Model. 2021 Mar 31;27(4):116. doi: 10.1007/s00894-021-04725-0. PMID: 33788017. 9: Silva J, Alves C, Martins A, Susano P, Simões M, Guedes M, Rehfeldt S, Pinteus S, Gaspar H, Rodrigues A, Goettert MI, Alfonso A, Pedrosa R. 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 Feb 14;22(4):1888. doi: 10.3390/ijms22041888. PMID: 33672866; PMCID: PMC7918146. 10: Lee HG, Kim HS, Je JG, Hwang J, Sanjeewa KKA, Lee DS, Song KM, Choi YS, Kang MC, Jeon YJ. Lipid Inhibitory Effect of (-)-loliolide Isolated from Sargassum horneri in 3T3-L1 Adipocytes: Inhibitory Mechanism of Adipose-Specific Proteins. Mar Drugs. 2021 Feb 8;19(2):96. doi: 10.3390/md19020096. PMID: 33567534; PMCID: PMC7915803. 11: Choi YH, Lee JY, Lee JE, Jung YW, Jeong W, Hong SS, Cho YR, Choi CW. Skin- Related Properties and Constituents from the Aerial Parts Extract of Persicaria senticosa. Oxid Med Cell Longev. 2020 Dec 19;2020:6627752. doi: 10.1155/2020/6627752. PMID: 33414895; PMCID: PMC7769672. 12: Duan H, Wang GC, Khan GJ, Su XH, Guo SL, Niu YM, Cao WG, Wang WT, Zhai KF. Identification and characterization of potential antioxidant components in Isodon amethystoides (Benth.) Hara tea leaves by UPLC-LTQ-Orbitrap-MS. Food Chem Toxicol. 2021 Feb;148:111961. doi: 10.1016/j.fct.2020.111961. Epub 2020 Dec 29. PMID: 33385513. 13: Malarz J, Michalska K, Stojakowska A. Stem Lettuce and Its Metabolites: Does the Variety Make Any Difference? Foods. 2020 Dec 29;10(1):59. doi: 10.3390/foods10010059. PMID: 33383824; PMCID: PMC7824169. 14: Moreno JC, Mi J, Alagoz Y, Al-Babili S. Plant apocarotenoids: from retrograde signaling to interspecific communication. Plant J. 2021 Jan;105(2):351-375. doi: 10.1111/tpj.15102. Epub 2021 Jan 8. PMID: 33258195; PMCID: PMC7898548. 15: Gangadhar KN, Rodrigues MJ, Pereira H, Gaspar H, Malcata FX, Barreira L, Varela J. Anti-Hepatocellular Carcinoma (HepG2) Activities of Monoterpene Hydroxy Lactones Isolated from the Marine Microalga Tisochrysis Lutea. Mar Drugs. 2020 Nov 19;18(11):567. doi: 10.3390/md18110567. PMID: 33227960; PMCID: PMC7699183. 16: Kłeczek N, Malarz J, Gierlikowska B, Kiss AK, Stojakowska A. Constituents of Xerolekia speciosissima (L.) Anderb. (Inuleae), and Anti-Inflammatory Activity of 7,10-Diisobutyryloxy-8,9-epoxythymyl Isobutyrate. Molecules. 2020 Oct 23;25(21):4913. doi: 10.3390/molecules25214913. PMID: 33114240; PMCID: PMC7660698. 17: Wang NQ, Kong CH, Wang P, Meiners SJ. Root exudate signals in plant-plant interactions. Plant Cell Environ. 2021 Apr;44(4):1044-1058. doi: 10.1111/pce.13892. Epub 2020 Oct 7. PMID: 32931018. 18: Su SQ, Jiang H, Li QM, Zha XQ, Luo JP. [Study on chemical constituents of Dendrobium huoshanense stems and their anti-inflammatory activity]. Zhongguo Zhong Yao Za Zhi. 2020 Jul;45(14):3452-3458. Chinese. doi: 10.19540/j.cnki.cjcmm.20200423.201. PMID: 32726061. 19: Mohsenian Kouchaksaraee R, Moridi Farimani M, Li F, Nazemi M, Tasdemir D. Integrating Molecular Networking and 1H NMR Spectroscopy for Isolation of Bioactive Metabolites from the Persian Gulf Sponge Axinella sinoxea. Mar Drugs. 2020 Jul 16;18(7):366. doi: 10.3390/md18070366. PMID: 32708620; PMCID: PMC7404180. 20: Feng ZY, Ma YX, Wang H, Chen M. [Studies on chemical constituents of stems of Herpetospermum pedunculosum]. Zhongguo Zhong Yao Za Zhi. 2020 Jun;45(11):2571-2577. Chinese. doi: 10.19540/j.cnki.cjcmm.20200227.201. PMID: 32627491.