Phenylpyropenes E and F: new meroterpenes from the marine-derived fungus Penicillium concentricum ZLQ-69

Ding, Zhuang; Zhang, Lianqing; Fu, Jing; Che, Qian; Li, Dehai; Gu, Qianqun; Zhu, Tianjiao

doi:10.1038/ja.2015.64

Cited by 20 publications

(7 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Phenylpyropenes E (407) and F (408) and seven known phenylpyropenes and pyripyropenes, were characterized from the marine-derived fungus Penicillium concentricum ZLQ-69 (seawater, Bohai Sea coast, China) [134]. In the bioassay of the three strains of HTCLs, only 407 and phenylpyropene C showed moderate cytotoxicity toward MGC-803 cells (IC 50 = 19.1 and 13.6 µM, respectively) [134].…”

Section: Aspergillus Spmentioning

confidence: 99%

A Review of Terpenes from Marine-Derived Fungi: 2015–2019

Jiang

Guo

et al. 2020

Marine Drugs

View full text Add to dashboard Cite

Marine-derived fungi are a significant source of pharmacologically active metabolites with interesting structural properties, especially terpenoids with biological and chemical diversity. In the past five years, there has been a tremendous increase in the rate of new terpenoids from marine-derived fungi being discovered. In this updated review, we examine the chemical structures and bioactive properties of new terpenes from marine-derived fungi, and the biodiversity of these fungi from 2015 to 2019. A total of 140 research papers describing 471 new terpenoids of six groups (monoterpenes, sesquiterpenes, diterpenes, sesterterpenes, triterpenes, and meroterpenes) from 133 marine fungal strains belonging to 34 genera were included. Among them, sesquiterpenes, meroterpenes, and diterpenes comprise the largest proportions of terpenes, and the fungi genera of Penicillium, Aspergillus, and Trichoderma are the dominant producers of terpenoids. The majority of the marine-derived fungi are isolated from live marine matter: marine animals and aquatic plants (including mangrove plants and algae). Moreover, many terpenoids display various bioactivities, including cytotoxicity, antibacterial activity, lethal toxicity, anti-inflammatory activity, enzyme inhibitor activity, etc. In our opinion, the chemical diversity and biological activities of these novel terpenoids will provide medical and chemical researchers with a plenty variety of promising lead compounds for the development of marine drugs.

show abstract

Section: Aspergillus Spmentioning

confidence: 99%

A Review of Terpenes from Marine-Derived Fungi: 2015–2019

Jiang

Guo

et al. 2020

Marine Drugs

View full text Add to dashboard Cite

show abstract

“…Two sesquiterpene α-pyrones, phenylpyropenes E and F ( 126 – 127 ) ( Figure 20 ), were isolated from the marine-derived fungus P. concentricum ZLQ-69 and displayed moderate and selective cytotoxicity against MGC-803 cells (human gastric cancer) with IC 50 values of 19.1 and 13.6 μM, respectively (doxorubicin was used as a positive control with an IC 50 value of 0.37 μM) [ 81 ]. Furthermore, the marine sediment-derived fungus Penicillium sp.…”

Section: Terpenes Meroterpenes and Steroidsmentioning

confidence: 99%

“… Marine (not clear) Meroterpene A549, SKOV-3, SKMEL-2, XF498, HCT-15 (25.44, 37.29, 18.41, 38.07, 42.56) μg/mL [ 79 ] Penicillone A ( 125 ) Penicillium sp. F11 Marine (not clear) Meroterpene HT1080, Cne2 (45.8, 46.2) μM [ 80 ] Phenylpyropene E ( 126 ) P. concentricum ZLQ-69 Sea water Sesquiterpene MGC-803 19.1 μM [ 81 ] Phenylpyropene F ( 127 ) P. concentricum ZLQ-69 Sea water Sesquiterpene MGC-803 13.6 μM [ 81 ] Penicillipyrone A ( 128 ) Penicillium sp. F446 Marine sediment Sesquiterpene K562, A549 (28, 15) μM [ 82 ] Penicillipyrone B ( 129 ) …”

Section: Table A1mentioning

confidence: 99%

Marine-Derived Penicillium Species as Producers of Cytotoxic Metabolites

Liu

Song

et al. 2017

Marine Drugs

View full text Add to dashboard Cite

Since the discovery of penicillin, Penicillium has become one of the most attractive fungal genera for the production of bioactive molecules. Marine-derived Penicillium has provided numerous excellent pharmaceutical leads over the past decades. In this review, we focused on the cytotoxic metabolites * (* Cytotoxic potency was referred to five different levels in this review, extraordinary (IC50/LD50: <1 μM or 0.5 μg/mL); significant (IC50/LD50: 1~10 μM or 0.5~5 μg/mL); moderate (IC50/LD50: 10~30 μM or 5~15 μg/mL); mild (IC50/LD50: 30~50 μM or 15~25 μg/mL); weak (IC50/LD50: 50~100 μM or 25~50 μg/mL). The comparative potencies of positive controls were referred when they were available). produced by marine-derived Penicillium species, and on their cytotoxicity mechanisms, biosyntheses, and chemical syntheses.

show abstract

“…Their structures were contained in three parts: a pyridine/phenyl ring, an α-pyrone, and a sesquiterpene motif. Subsequently, they were first isolated in 1994, 19 pyripyropenes were exhibit to be effective as acyl-CoA/cholesterol acyltransferase (ACAT) inhibitors and are thought to be beneficial in the avoidance and treatment of hypercholesterolemia and atherosclerosis [55][56][57][58][59][60]. In the marine environment, meroterpenes are compounds of assorted biosynthesis, essentially quinone or hydroquinones bonded with a terpenoid portion differing from one to nine isoprene units.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Meroterpenes: A Review

2020

J Pharmacol Pharm Res

View full text Add to dashboard Cite

Meroterpenes are mixed natural products. They consist of one terpene and one polyketide skeletons. Due to their structural varieties, meroterpenoids display diverse bioactivities, like anticancer, anti-inflammatory, antibiotic , and antifibrotic activities. Our aim is to highlight the importance of the meroterpenes which have been the most studied on and reported among the bioactive natural products last years. According to our literature survey, the three most effective meroterpene groups have been determined. One group is the meroterpenes isolated from the brown alga Sargassum siliquastrum: Sargachromanol E, D, and P have exerted strong cytotoxicity against AGS (gastric cancer cells), HT-29 (colorectal adenocarcinoma cancer cell), and HT-1080 (human fibrosarcoma cells) cell lines, with IC 50 values varying from 0.5 to 5.7 μg/mL [100]. The other most effective meroterpene is Eucalypglobulusal F, which is isolated from E. globulus fruit, has shown cytotoxicity against the human acute lymphoblastic cell line (CCRF-CEM) with an IC 50 value of 3.3 μM [89]. Also, the last one is 11-dehydroxy epoxyphomalin A (4), from the endophytic fungus Peyronellaea coffeae-arabicae FT238, which was obtained from the native Hawaiian plant Pritchardia lowreyana showed a strong antiproliferative effect with an IC 50 of 0.5 μM against OVCAR3 (Ovarian carsinoma cells) [102]. Conclusively, meroterpenes have potential nominees as an anticancer drug. Moreover, the structure of naturally isolated meroterpenes has a moderate anticancer activity that can easliy be modified by semi-synthetic ways due to their simple structures comparing to other natural compounds such as triterpenes or phenolic compounds.

show abstract

Phenylpyropenes E and F: new meroterpenes from the marine-derived fungus Penicillium concentricum ZLQ-69

Cited by 20 publications

References 27 publications

A Review of Terpenes from Marine-Derived Fungi: 2015–2019

A Review of Terpenes from Marine-Derived Fungi: 2015–2019

Marine-Derived Penicillium Species as Producers of Cytotoxic Metabolites

Cytotoxic Meroterpenes: A Review

Contact Info

Product

Resources

About