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Loliolid

$655

  • Brand : BIOFRON

  • Catalogue Number : AV-B04101

  • Specification : 98%

  • CAS number : 5989-02-6

  • Formula : C11H16O3

  • Molecular Weight : 196.24

  • PUBCHEM ID : 100332

  • Volume : 5mg

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Catalogue Number

AV-B04101

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

196.24

Appearance

Powder

Botanical Source

Structure Type

Monoterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(CC(CC2(C1=CC(=O)O2)C)O)C

Synonyms

Digiprolactone/loliolide

IUPAC Name

(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one

Applications

590

Density

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

Boiling Point

Melting Point

151-153℃

InChl

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

InChl Key

XEVQXKKKAVVSMW-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:5989-02-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

31610126

Abstract

The liver X receptors (LXRs) are major regulators of lipogenesis, and their reduced activation by an inhibitor could be a treatment strategy for fatty liver disease. Small molecules originating from dietary food are considered suitable and attractive drug candidates for humans in terms of safety. In this study, an edible plant, Lysimachia vulgaris (LV), used as a traditional and medicinal food in East Asia was evaluated for lipogenesis decreasing effects. Activity-guided fractionation was performed, and the isolated compounds were identified using spectroscopic methods. We conducted in vitro real-time polymerase chain reaction (PCR) and Western blotting as well as histological and biochemical analyses following in vivo treatments. Using a high-fat diet animal model, we confirmed that LV extracts (LVE) decreased lipogenic metabolism and restored liver function to control levels. To identify active components, we conducted activity-guided fractionation and then isolated compounds. Two compounds, loliolide and pinoresinol, were identified in the dichloromethane fraction, and they significantly attenuated the expression levels of lipogenic factors including sterol regulatory element-binding protein (SREBP)-1, stearoyl-CoA desaturase 1 (SCD1), fatty acid synthase (FAS), and acetyl-CoA carboxylase (ACC). Importantly, loliolide and pinoresinol significantly accelerated the protein degradation of LXRs by enhanced ubiquitination, which inhibited lipogenesis. These results suggest that loliolide and pinoresinol might be potential candidate supplementary treatments for nonalcoholic fatty liver disease (NAFLD) by reducing lipogenesis through increased ubiquitination of LXRs.

KEYWORDS

Lysimachia vulgaris; lipogenesis; liver X receptors; loliolide; pinoresinol

Title

Reduction of Hepatic Lipogenesis by Loliolide and Pinoresinol from Lysimachia vulgaris via Degrading Liver X Receptors.

Author

Kim SY1, Lee JY2, Jhin C1, Shin JM1,3, Kim M1, Ahn HR2, Yoo G1, Son YJ1, Jung SH2, Nho CW1.

Publish date

2019 Nov 13

PMID

31601058

Abstract

Loliolide is one of the most ubiquitous monoterpenoid compounds found in algae, and its potential therapeutic effect on various dermatological conditions via agent-induced biological functions, including anti-oxidative and anti-apoptotic properties, was demonstrated. Here, we investigated the effects of loliolide on hair growth in dermal papilla (DP) cells, the main components regulating hair growth and loss conditions. For this purpose, we used a threedimensional (3D) DP spheroid model that mimics the in vivo hair follicle system. Biochemical assays showed that low doses of loliolide increased the viability and size of 3D DP spheroids in a dose-dependent manner. This result correlated with increases in expression levels of hair growth-related autocrine factors including VEGF, IGF-1, and KGF. Immunoblotting and luciferase-reporter assays further revealed that loliolide induced AKT phosphorylation, and this effect led to stabilization of β-catenin, which plays a crucial role in the hair-inductive properties of DP cells. Further experiments showed that loliolide increased the expression levels of the DP signature genes, ALP, BMP2, VCAN, and HEY1. Furthermore, conditioned media from loliolide-treated DP spheroids significantly enhanced proliferation and the expression of hair growth regulatory genes in keratinocytes. These results suggested that loliolide could function in the hair growth inductivity of DP cells via the AKT/ β-catenin signaling pathways.

KEYWORDS

AKT; Loliolide; dermal papilla; hair follicle induction; migration; spheroids

Title

Monoterpenoid Loliolide Regulates Hair Follicle Inductivity of Human Dermal Papilla Cells by Activating the Akt/β-Catenin Signaling Pathway.

Author

Lee YR1, Bae S1, Kim JY1,2, Lee J1,2, Cho DH3, Kim HS3,4, An IS2, An S1.

Publish date

2019 Nov 28

PMID

30717391

Abstract

Loliolide is a monoterpenoid hydroxylactone present in freshwater algae that has anti-inflammatory and antiaging activity; however, its effects on ultraviolet-damaged skin have yet to be elucidated. This study investigated the antiapoptosis and wound-healing effects of loliolide using HaCaT cells (a human keratinocyte cell line). Loliolide inhibited the expression of reactive oxygen species (ROS) induced by ultraviolet radiation as well as wrinkle formation-related matrix metalloproteinase genes and increased the expression of the damage repair-related gene SIRT1. The apoptosis signaling pathway was confirmed by Western blot analysis, which showed that loliolide was able to reduce the expression of caspases 3, 8, and 9, which are related to ROS-induced apoptosis. In addition, Western blotting, reverse-transcription polymerase chain reaction (PCR), and real-time PCR analyses showed that loliolide enhanced the expression of the epidermal growth factor receptor signaling pathway (PI3K, AKT) and migration factors, such as K6, K16, and K17; keratinocyte growth factor; and inflammatory cytokines, such as interleukin (IL)-1, IL-17, and IL-22 expressed during the cellular scratching process, suggesting a putative wound-healing ability. Because of the antiapoptosis and antiscratching effects on skin of both loliolide and loliolide-rich Prasiola japonica ethanol extract, we consider the former to be an important compound used in the cosmeceutical industry.

KEYWORDS

antiapoptosis; antioxidant activity; antiscratching effect; antiwrinkling activity

Title

Loliolide Presents Antiapoptosis and Antiscratching Effects in Human Keratinocytes.

Author

Park SH1, Kim DS2, Kim S3,4, Lorz LR5, Choi E6, Lim HY7, Hossain MA8, Jang S9, Choi YI10, Park KJ11, Yoon K12, Kim JH13, Cho JY14,15.

Publish date

2019 Feb 2