Terrein, a fungal metabolite, inhibits the epidermal proliferation of skin equivalents

Kim, Dong-Seok; Cho, Hyun-Joo; Lee, Hyun-Kyung; Lee, Woonghee; Park, Eun-Sang; Youn, Sung Won; Park, Kyoung-Chan

doi:10.1016/j.jdermsci.2006.11.011

Cited by 24 publications

(20 citation statements)

References 8 publications

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“…However, the biological effects of 2 have been almost unknown. Recently, 2 was reported to inhibit the melanogenesis [20] and the epidermal proliferation of skin equivalents [21]. Although whether 2 affects the angiogenesis-related factors has been unknown before, we have shown here that 1 and 2 inhibited angiogenin secretion from LNCaP-CR cells with IC 50 values of 13 mM, respectively (Table 3).…”

Section: Effect Of 1 and 2 On Angiogenin Secretion From Prostatesupporting

confidence: 50%

A New Terrein Glucoside, a Novel Inhibitor of Angiogenin Secretion in Tumor Angiogenesis

et al. 2008

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Angiogenesis is a critical step for the tumor therapy. Many angiogenic factors are involved in the tumor angiogenesis. In the course of our screening for inhibitors of angiogenin secretion, one of angiogenic factors, we have isolated a new terrein glucoside (1) and terrein (2) from the fermentation broth of fungal strain Aspergillus sp. PF1381. The structure and absolute stereochemistry of 1 was determined to be (4S,5R)-5-[(a -D-glucopyranosyl)oxy]-4-hydroxy-3-(E-1-propenyl)-2-cyclopenten-1-one on the basis of spectral and enzymatic analyses. Compounds 1 and 2 equally inhibited angiogenin secretion from androgendependent prostate cancer cells, LNCaP-CR, with IC 50 values of 13 mM. However, both compounds did not affect VEGF secretion, another angiogenic factor. Furthermore, both compounds inhibited tube formation of human umbilical vein endothelial cells (HUVEC). These results suggested that 1 and 2 act as angiogenesis inhibitors through the inhibition of angiogenin secretion.

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Section: Effect Of 1 and 2 On Angiogenin Secretion From Prostatesupporting

confidence: 50%

A New Terrein Glucoside, a Novel Inhibitor of Angiogenin Secretion in Tumor Angiogenesis

et al. 2008

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“…Terrein is a fungal metabolite which has already been shown to have valuable bioactivity in the fields of medicine, cosmetology and agriculture without any cytotoxic effects (22)(23)(24)(25)(26)(27)(28)(29)(30). In the present study, we separated terrein from the fermentation broth of sponge-derived fungus with high efficiency and purity, showing it to be an economic and environmentally-friendly drug candidate (31).…”

Section: Discussionmentioning

confidence: 71%

“…Terrein (4,5-dihydroxy-3-[(E)-1'-propenyl]-2-cyclopenten-l-one, C 8 H 10 O 3 ) was first isolated from Aspergillus terreus Thom in 1935 (22), and has since been tested in several applications across different fields, including the fields of medicine, cosmetology and agriculture (23)(24)(25)(26)(27)(28)(29). However, the biological function of terrein in targeting human diseases has not been extensively investigated.…”

Section: Introductionmentioning

confidence: 99%

“…However, the biological function of terrein in targeting human diseases has not been extensively investigated. Studies have demonstrated the strong anti-proliferative effects of terrein on skin equivalents through the induction of G 2 /M cell cycle arrest (27,30), suggesting its potential as a valuable candidate for treating hyper-proliferative skin diseases. However, the antitumor activity of terrein remains to be investigated.…”

Section: Introductionmentioning

confidence: 99%

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The marine-derived fungal metabolite, terrein, inhibits cell proliferation and induces cell cycle arrest in human ovarian cancer cells

Chen

Wang

Shen

et al. 2014

International Journal of Molecular Medicine

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Abstract. The difficulties faced in the effective treatment of ovarian cancer are multifactorial, but are mainly associated with relapse and drug resistance. Cancer stem-like cells have been reported to be an important contributor to these hindering factors. In this study, we aimed to investigate the anticancer activities of a bioactive fungal metabolite, namely terrein, against the human epithelial ovarian cancer cell line, SKOV3, primary human ovarian cancer cells and ovarian cancer stem-like cells. Terrein was separated and purified from the fermentation metabolites of the marine sponge-derived fungus, Aspergillus terreus strain PF26. Its anticancer activities against ovarian cancer cells were investigated by cell proliferation assay, cell migration assay, cell apoptosis and cell cycle assays. The ovarian cancer stem-like cells were enriched and cultured in a serum-free in vitro suspension system. Terrein inhibited the proliferation of the ovarian cancer cells by inducing G 2 /M phase cell cycle arrest. The underlying mechanisms involved the suppression of the expression of LIN28, an important marker gene of stemness in ovarian cancer stem cells. Of note, our study also demonstrated the ability of terrein to inhibit the proliferation of ovarian cancer stem-like cells, in which the expression of LIN28 was also downregulated. Our findings reveal that terrein (produced by fermention) may prove to be a promising drug candidate for the treatment of ovarian cancer by inhibiting the proliferation of cancer stem-like cells.

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“…This metabolite has been already reported to inhibit cell proliferation, to induce cell cycle arrest in human ovarian tumor cells (SKOV3,) and to inhibit the proliferation of ovarian cancer stem-like cells [217], to inhibit the epidermal proliferation of skin [218], as well as to inhibit melanogenesis [219]. It also displayed a strong cytotoxicity against breast cancer (MCF-7) cell and suppressed the growth of MCF-7 expressing BCRP cells by inducing apoptosis caspase-7 pathway, and inhibiting the Akt signaling pathway [220].…”

Section: Terreinmentioning

confidence: 96%

Marine Natural Products as Models to Circumvent Multidrug Resistance

et al. 2016

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Multidrug resistance (MDR) to anticancer drugs is a serious health problem that in many cases leads to cancer treatment failure. The ATP binding cassette (ABC) transporter P-glycoprotein (P-gp), which leads to premature efflux of drugs from cancer cells, is often responsible for MDR. On the other hand, a strategy to search for modulators from natural products to overcome MDR had been in place during the last decades. However, Nature limits the amount of some natural products, which has led to the development of synthetic strategies to increase their availability. This review summarizes the research findings on marine natural products and derivatives, mainly alkaloids, polyoxygenated sterols, polyketides, terpenoids, diketopiperazines, and peptides, with P-gp inhibitory activity highlighting the established structure-activity relationships. The synthetic pathways for the total synthesis of the most promising members and analogs are also presented. It is expected that the data gathered during the last decades concerning their synthesis and MDR-inhibiting activities will help medicinal chemists develop potential drug candidates using marine natural products as models which can deliver new ABC transporter inhibitor scaffolds.

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Terrein, a fungal metabolite, inhibits the epidermal proliferation of skin equivalents

Cited by 24 publications

References 8 publications

A New Terrein Glucoside, a Novel Inhibitor of Angiogenin Secretion in Tumor Angiogenesis

A New Terrein Glucoside, a Novel Inhibitor of Angiogenin Secretion in Tumor Angiogenesis

The marine-derived fungal metabolite, terrein, inhibits cell proliferation and induces cell cycle arrest in human ovarian cancer cells

Marine Natural Products as Models to Circumvent Multidrug Resistance

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