• Natural Product Sciences
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• v.22 no.2
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• pp.134-139
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• 2016

Phytochemicals were isolated from leaves of the fiber crop, ramie (Boehmeria nivea, Bn), using open column chromatography and medium pressure liquid chromatography. Their structures were identified as ${\beta}$-sitosterol, (-)-loliolide, rutin, and pyrimidinedione by MS, $^1H$-, and $^{13}C$-NMR spectroscopic analysis. Among them, (-)-loliolide was isolated for the first time from B. nivea. A content analysis of (-)-loliolide in B. nivea collected from different regions and harvest times was conducted by HPLC. The highest content of (-)-loliolide was found in Bn-23 harvested in September. These results will be helpful to use the plant which harvest in September as a high content phytochemical additive in food, health supplements, and medicinal products.

• Journal of Microbiology and Biotechnology
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• v.29 no.11
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• pp.1830-1840
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• 2019

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 three-dimensional (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 pathway.

• ALGAE
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• v.26 no.2
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• pp.201-208
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• 2011

A monoterpene lactone, loliolide was successively isolated from brown seaweed, Sargassum ringgoldianum subsp. coreanum using column chromatography and high-performance liquid chromatography. The structure of the isolated compound was determined by comparison of EIMS and NMR spectral data with the previously published data. The antioxidant activities of loliolide were also evaluated by DPPH and $H_2O_2$ radical and intracellular reactive oxygen species scavenging assays, and it showed moderate activities in all antioxidant assays. Furthermore, loliolide was found to exert positive dose-dependent effects in the protective effects against $H_2O_2$-induced cell damage which were determined via MTT, Hoechst staining assays and cell cycle analysis. This is the first study on chemical constituent of this seaweed according to our best knowledge. These results clearly indicated that loliolide isolated from Sargassum ringgoldianum subsp. coreanum can protect the cells against $H_2O_2$-induced cell damage or apoptosis.

• Journal of Microbiology and Biotechnology
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• v.33 no.9
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• pp.1250-1256
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• 2023

Herein, different extracts of Scenedesmus deserticola JD052, a green microalga, were evaluated in vitro as a potential anti-aging bioagent. Although post-treatment of microalgal culture with either UV irradiation or high light illumination did not lead to a substantial difference in the effectiveness of microalgal extracts as a potential anti-UV agent, the results indicated the presence of a highly potent compound in ethyl acetate extract with more than 20% increase in the cellular viability of normal human dermal fibroblasts (nHDFs) compared with the negative control amended with DMSO. The subsequent fractionation of the ethyl acetate extract led to two bioactive fractions with high anti-UV property; one of the fractions was further separated down to a single compound. While electrospray ionization mass spectrometry (ESI-MS) and nuclear magnetic resonance (NMR) spectroscopy analysis identified this single compound as loliolide, its identification has been rarely reported in microalgae previously, prompting thorough systematic investigations into this novel compound for the nascent microalgal industry.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.50 no.spc1
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• pp.208-210
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• 2005

Four compounds were isolated from Suaeda japonica by repeated column chromatography. Their structures were identified as 2'-hydroxy-6,7-methylenedioxy-isoflavone (1), loliolide (2), dehydrovomifoliol (3), and uridine (4) by spectral analysis and comparison with the published data. All compounds were isolated for the first time from this plant.

• YAKHAK HOEJI
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• v.34 no.1
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• pp.64-68
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• 1990

Three non-alkaloidal constituents, (-)-loliolide as an iridoid, friedelin as a triterpenoid, and ${\beta}-sitosterol$ as a steroid, were isolated by fractional extraction and silica gel column chromatography from the herb of Commelina communis L. (Commelinaceae). The structures of the native components were elucidated on the basis of physical and spectral (UV, IR, PMR, CMR, and mass spectra) data.

• Korean Journal of Pharmacognosy
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• v.33 no.2 s.129
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• pp.81-84
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• 2002

Three norisoprenoids (2, 4 and 5) were isolated from the aerial parts of Cirsium rhinoceros (Compositae) together with three flavonoids, pectolinarigenin (1), apigenin (3) and cirsimaritin (6). The structures of norisoprenoids were identified as dehydrovomifoliol (2), (+)-loliolide (4) and (-)-epiloliolide (5) on the basis of physico-chemical and spectral evidences. These norisoprenoids were first repoted from Cirsium species.

• Journal of the Korean Chemical Society
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• v.48 no.4
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• pp.394-398
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• 2004

From Sargassum thunbergii which is widely distributed in coastal area of Korea, three norisoprenoids, (+)-epiloliolide (1), (-)-loliolide (2), and apo-9'-fucoxanthinone (3) were isolated by using column chromatography and reverse-phase HPLC. Compound 1, 2 and 3 were for the first time isolated from the Brown Alga Sargassum thunbergii. Particularly, Compound 1 was for the first time isolated the marine organism although it was reported from the terrestrial plant. Their structures have been determined by extensive 2-D NMR experiments such as $^1H COSY, NOESY, HMQC$, and HMBC and by comparison with the reported data in the literature.

• Applied Biological Chemistry
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• v.46 no.1
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• pp.55-59
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• 2003

Three terpenoids were isolated from the leaves of Chrysanthemum coronarium L. by silica gel chromatography and recrystalization. The structure of compounds 1, 2, and 3, using various spectroscopic data, were identified as to be terpenoid derivatives of dihydrotulipinolide, loliolide, and $5{\alpha},8{\alpha}-peroxyergosterol$, respectively. The presence of these 3 is the first time reported in this plant. The cytotoxic activity of $5{\alpha},8{\alpha}-peroxyergosterol$ showed strong activities against human cancer cell lines such as A549, PC-3, and HCT 116.

• Natural Product Sciences
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• v.15 no.4
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• pp.246-249
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• 2009

Column chromatographic separation of the MeOH extract from the aerial parts of Thesium chinense TURCZ led to the isolation of two norsesquiterpenes (1 - 2), two phenylpropanes (3 - 4) and four flavonoids (5 - 8). Their structures were determined by spectroscopic means to be 5,6-epoxy-3-hydroxy-7-megastigmen-9-ene (1), (-)-loliolide (2), methyl-p-hydroxycinnamate (3), methyl caffeate (4), kaempferol (5), kaempferol-3-O-${\beta}$-Dglucopyranoside (6), kaepmferol-3,7-di-O-${\beta}$-D-glucopyranoside (7) and kaempferol-3-O-${\beta}$-D-glucopyranoside-6''-(3-hydroxy-3-methylglutarate) (8). Compounds 1 - 4, 7 and 8 were first isolated from this source. The isolated compounds were evaluated for their cytotoxicty in vitro using the sulforhodamin B bioassay (SRB).