Terpenoids from the Deep-Sea-Derived Fungus Penicillium thomii YPGA3 and Their Bioactivities.

Abstract:

:A chemical study of the ethyl acetate (EtOAc) extract from the deep-sea-derived fungus Penicilliumthomii YPGA3 led to the isolation of a new austalide meroterpenoid (1) and seven known analogues (28), two new labdane-type diterpenoids (9 and 10) and a known derivative (11). The structures of new compounds 1, 9, and 10 were determined by comprehensive analyses via nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data. The absolute configurations of 1, 9, and 10 were determined by comparisons of experimental electronic circular dichroism (ECD) with the calculated ECD spectra. Compound 1 represented the third example of austalides bearing a hydroxyl group at C-5 instead of the conserved methoxy in other known analogues. To our knowledge, diterpenoids belonging to the labdane-type were discovered from species of Penicillium for the first time. Compound 1 showed cytotoxicity toward MDA-MB-468 cells with an IC50 value of 38.9 M. Compounds 2 and 11 exhibited inhibition against α-glucosidase with IC50 values of 910 and 525 M, respectively, being more active than the positive control acarbose (1.33 mM).

journal_name

Mar Drugs

journal_title

Marine drugs

authors

Cheng Z,Liu W,Fan R,Han S,Li Y,Cui X,Zhang J,Wu Y,Lv X,Zhang Y,Luo Z,Alias SA,Xu W,Li Q

doi

10.3390/md18030164

subject

Has Abstract

pub_date

2020-03-16 00:00:00

issue

3

issn

1660-3397

pii

md18030164

journal_volume

18

pub_type

杂志文章
  • Spirulina maxima Derived Pectin Nanoparticles Enhance the Immunomodulation, Stress Tolerance, and Wound Healing in Zebrafish.

    abstract::In this study, Spirulina maxima derived pectin nanoparticles (SmPNPs) were synthesized and multiple biological effects were investigated using in vitro and in vivo models. SmPNPs were not toxic to Raw 264.7 cells and zebrafish embryos up to 1 mg/mL and 200 µg/mL, respectively. SmPNPs upregulated Il 10, Cat, Sod 2, Def...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md18110556

    authors: Rajapaksha DC,Edirisinghe SL,Nikapitiya C,Dananjaya S,Kwun HJ,Kim CH,Oh C,Kang DH,De Zoysa M

    更新日期:2020-11-07 00:00:00

  • Spiromastixones Inhibit Foam Cell Formation via Regulation of Cholesterol Efflux and Uptake in RAW264.7 Macrophages.

    abstract::Bioassay-guided evaluation shows that a deep sea-derived fungus, Spiromastix sp. MCCC 3A00308, possesses lipid-lowering activity. Chromatographic separation of a culture broth resulted in the isolation of 15 known depsidone-based analogues, labeled spiromastixones A-O (1-15). Each of these compounds was tested for its...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md13106352

    authors: Wu C,Chen R,Liu M,Liu D,Li X,Wang S,Niu S,Guo P,Lin W

    更新日期:2015-10-14 00:00:00

  • Angiotensin-I Converting Enzyme (ACE) Inhibitory and Anti-Hypertensive Effect of Protein Hydrolysate from Actinopyga lecanora (Sea Cucumber) in Rats.

    abstract::Food protein hydrolysates are known to exhibit angiotensin converting enzyme (ACE) inhibitory properties and can be used as a novel functional food for prevention of hypertension. This study evaluated the ACE inhibitory potentials of Actinopyga lecanora proteolysate (ALP) in vivo. The pre-fed rats with ALP at various ...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md14100176

    authors: Sadegh Vishkaei M,Ebrahimpour A,Abdul-Hamid A,Ismail A,Saari N

    更新日期:2016-09-30 00:00:00

  • New 9α-Hydroxy-5α,6α-epoxyhydroxysterols from the Vietnamese Marine Sponge Ircinia echinata.

    abstract::Chemical investigation of the methanol extract of the Vietnamese marine sponge Ircinia echinata led to the isolation of six new 9α-hydroxy-5α,6α-epoxysterols: 5α,6α-epoxycholesta-7,22(E)-dien-3β,9α-diol (1), 5α,6α-epoxycholesta-7,24(28)-dien-3β,9α-diol (2), (24R)-5α,6α-epoxy-24-ethyl-cholesta-7-en-3β,9α-diol (3), 5α,6...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md16110424

    authors: Trinh TTV,Truong BN,Longeon A,Doan TMH,Deville A,Chau VM,Pham VC,Bourguet-Kondracki ML

    更新日期:2018-11-01 00:00:00

  • Aeroplysinin-1, a Sponge-Derived Multi-Targeted Bioactive Marine Drug.

    abstract::Organisms lacking external defense mechanisms have developed chemical defense strategies, particularly through the production of secondary metabolites with antibiotic or repellent effects. Secondary metabolites from marine organisms have proven to be an exceptionally rich source of small molecules with pharmacological...

    journal_title:Marine drugs

    pub_type: 杂志文章,评审

    doi:10.3390/md14010001

    authors: García-Vilas JA,Martínez-Poveda B,Quesada AR,Medina MÁ

    更新日期:2015-12-22 00:00:00

  • Marine-Inspired Bis-indoles Possessing Antiproliferative Activity against Breast Cancer; Design, Synthesis, and Biological Evaluation.

    abstract::Diverse indoles and bis-indoles extracted from marine sources have been identified as promising anticancer leads. Herein, we designed and synthesized novel bis-indole series 7a-f and 9a-h as Topsentin and Nortopsentin analogs. Our design is based on replacing the heterocyclic spacer in the natural leads by a more flex...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md18040190

    authors: Eldehna WM,Hassan GS,Al-Rashood ST,Alkahtani HM,A Almehizia A,Al-Ansary GH

    更新日期:2020-04-02 00:00:00

  • Marine Compound 3-bromo-4,5-dihydroxybenzaldehyde Protects Skin Cells against Oxidative Damage via the Nrf2/HO-1 Pathway.

    abstract::In this study, we aimed to illustrate the potential bio-effects of 3-bromo-4,5-dihydroxybenzaldehyde (3-BDB) on the antioxidant/cytoprotective enzyme heme oxygenase-1 (HO-1) in keratinocytes. The antioxidant effects of 3-BDB were examined via reverse transcription PCR, Western blotting, HO-1 activity assay, and immuno...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md17040234

    authors: Ryu YS,Fernando PDSM,Kang KA,Piao MJ,Zhen AX,Kang HK,Koh YS,Hyun JW

    更新日期:2019-04-19 00:00:00

  • Inhibitory activity of marine sponge-derived natural products against parasitic protozoa.

    abstract::In this study, thirteen sponge-derived terpenoids, including five linear furanoterpenes: furospinulosin-1 (1), furospinulosin-2 (2), furospongin-1 (3), furospongin-4 (4), and demethylfurospongin-4 (5); four linear meroterpenes: 2-(hexaprenylmethyl)-2-methylchromenol (6), 4-hydroxy-3-octaprenylbenzoic acid (7), 4-hydro...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md8010047

    authors: Orhan I,Sener B,Kaiser M,Brun R,Tasdemir D

    更新日期:2010-01-15 00:00:00

  • Fatty Acid Composition and Fatty Acid Associated Gene-Expression in Gilthead Sea Bream (Sparus aurata) are Affected by Low-Fish Oil Diets, Dietary Resveratrol, and Holding Temperature.

    abstract::To sustainably produce marine fish with a high lipid quality rich in omega-3 fatty acids, alternative sources of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are being identified. Moreover, the use of bioactive compounds that would stimulate the in vivo fatty acid synthesis, such as resveratrol (RV), wou...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md16100379

    authors: Torno C,Staats S,Michl SC,de Pascual-Teresa S,Izquierdo M,Rimbach G,Schulz C

    更新日期:2018-10-10 00:00:00

  • Purification and characterization of a bifunctional alginate lyase from Pseudoalteromonas sp. SM0524.

    abstract::An alginate lyase-producing bacterial strain, Pseudoalteromonas sp. SM0524, was screened from marine rotten kelp. In an optimized condition, the production of alginate lyase from Pseudoalteromonas sp. SM0524 reached 62.6 U/mL, suggesting that strain SM0524 is a good producer of alginate lyases. The bifunctional algina...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md9010109

    authors: Li JW,Dong S,Song J,Li CB,Chen XL,Xie BB,Zhang YZ

    更新日期:2011-01-21 00:00:00

  • Geographic variability and anti-staphylococcal activity of the chrysophaentins and their synthetic fragments.

    abstract::Drug-resistant Staphylococcus aureus is a continuing public health concern, both in the hospital and community settings. Antibacterial compounds that possess novel structural scaffolds and are effective against multiple S. aureus strains, including current drug-resistant ones, are needed. Previously, we have described...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md10051103

    authors: Keffer JL,Hammill JT,Lloyd JR,Plaza A,Wipf P,Bewley CA

    更新日期:2012-05-01 00:00:00

  • Natural product research in the Australian marine invertebrate Dicathais orbita.

    abstract::The predatory marine gastropod Dicathais orbita has been the subject of a significant amount of biological and chemical research over the past five decades. Natural products research on D. orbita includes the isolation and identification of brominated indoles and choline esters as precursors of Tyrian purple, as well ...

    journal_title:Marine drugs

    pub_type: 杂志文章,评审

    doi:10.3390/md11041370

    authors: Benkendorff K

    更新日期:2013-04-23 00:00:00

  • New Naphthoquinone Terpenoids from Marine Actinobacterium, Streptomyces sp. CNQ-509.

    abstract::A member of the marine streptomycete clade MAR4, Streptomyces sp. CNQ-509, has genetic potential for the biosynthesis of hybrid isoprenoids and produces several meroterpenoids such as naphterpin, nitropyrrolin and marinophenazine. Our research on the strain CNQ-509 led to the isolation of two new naphterpin derivative...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md16030090

    authors: Park JS,Kwon HC

    更新日期:2018-03-12 00:00:00

  • Physicochemical and Functional Properties of Type I Collagens in Red Stingray (Dasyatis akajei) Skin.

    abstract::Collagen is widely used in the pharmaceutical, tissue engineering, nutraceutical, and cosmetic industries. In this study, acid-soluble collagen (ASC) and pepsin-soluble collagen (PSC) were extracted from the skin of red stingray, and its physicochemical and functional properties were investigated. The yields of ASC an...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md17100558

    authors: Chen J,Li J,Li Z,Yi R,Shi S,Wu K,Li Y,Wu S

    更新日期:2019-09-28 00:00:00

  • Anti-Neuroinflammatory Agent, Restricticin B, from the Marine-Derived Fungus Penicillium janthinellum and Its Inhibitory Activity on the NO Production in BV-2 Microglia Cells.

    abstract::A new compound containing a triene, a tetrahydropyran ring and glycine ester functionalities, restricticin B (1), together with four known compounds (2-5) were obtained from the EtOAc extract of the marine-derived fungus Penicillium janthinellum. The planar structure of 1 was determined by detailed analyses of MS, 1D ...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md18090465

    authors: Choi BK,Jo SH,Choi DK,Trinh PTH,Lee HS,Cao VA,Van TTT,Shin HJ

    更新日期:2020-09-14 00:00:00

  • Anti-Coagulant and Anti-Thrombotic Properties of Blacklip Abalone (Haliotis rubra): In Vitro and Animal Studies.

    abstract::Sulphated polysaccharides with anti-thrombotic and anti-coagulant activities have been found in various marine biota. In this study, a previously characterised anti-thrombotic and anti-coagulant extract from blacklip abalone was fractionated by anion exchange chromatography (AEC), pooled (on a sulphated polysaccharide...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md15080240

    authors: Suleria HAR,Masci PP,Zhao KN,Addepalli R,Chen W,Osborne SA,Gobe GC

    更新日期:2017-08-04 00:00:00

  • Anti-Diabetic Activity of 2,3,6-Tribromo-4,5-Dihydroxybenzyl Derivatives from Symphyocladia latiuscula through PTP1B Downregulation and α-Glucosidase Inhibition.

    abstract::The marine alga, Symphyocladia latiuscula (Harvey) Yamada, is a good source of bromophenols with numerous biological activities. This study aims to characterize the anti-diabetic potential of 2,3,6-tribromo-4,5-dihydroxybenzyl derivatives isolated from S. latiuscula via their inhibition of tyrosine phosphatase 1B (PTP...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md17030166

    authors: Paudel P,Seong SH,Park HJ,Jung HA,Choi JS

    更新日期:2019-03-14 00:00:00

  • Cereus sinensis Polysaccharide and Its Immunomodulatory Properties in Human Monocytic Cells.

    abstract::In this study, the extraction conditions of the crude polysaccharide from Cereus sinensis were optimized by response surface methodology. The optimum extraction conditions were: a ratio of raw material to water volume of 1:80 (g/mL); an extraction temperature of 72 °C; and an extraction time of 3 h. Then, a purified p...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md15050140

    authors: Wu J,Zhou X,Zhang M,Yao Y,Han J,Liu K

    更新日期:2017-05-18 00:00:00

  • Cytotoxicity of the ascidian Cystodytes dellechiajei against tumor cells and study of the involvement of associated microbiota in the production of cytotoxic compounds.

    abstract::Many cytotoxic compounds of therapeutic interest have been isolated from marine invertebrates, and some of them have been reported to be of microbial origin. Pyridoacridine alkaloids are the main compounds extracted from the ascidian Cystodytes dellechiajei. Here we describe the in vitro antiproliferative activity aga...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md503052

    authors: Martinez-García M,Diaz-Valdés M,Ramos-Esplá A,Salvador N,Lopez P,Larriba E,Antón J

    更新日期:2007-07-19 00:00:00

  • From Aggregates to Porous Three-Dimensional Scaffolds through a Mechanochemical Approach to Design Photosensitive Chitosan Derivatives.

    abstract::The crustacean processing industry produces large quantities of waste by-products (up to 70%). Such wastes could be used as raw materials for producing chitosan, a polysaccharide with a unique set of biochemical properties. However, the preparation methods and the long-term stability of chitosan-based products limit t...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md17010048

    authors: Bardakova KN,Akopova TA,Kurkov AV,Goncharuk GP,Butnaru DV,Burdukovskii VF,Antoshin AA,Farion IA,Zharikova TM,Shekhter AB,Yusupov VI,Timashev PS,Rochev YA

    更新日期:2019-01-10 00:00:00

  • Two New Terpenoids from Talaromyces purpurogenus.

    abstract::A new sesquiterpenoid 9,10-diolhinokiic acid (1) and a new diterpenoid roussoellol C (2), together with 4 known compounds, were isolated from the extracts of laboratory cultures of marine-derived fungus Talaromyces purpurogenus. 9,10-diolhinokiic acid is the first thujopsene-type sesquiterpenoid containing a 9,10-diol...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md16050150

    authors: Wang W,Wan X,Liu J,Wang J,Zhu H,Chen C,Zhang Y

    更新日期:2018-05-02 00:00:00

  • Marine Carotenoids against Oxidative Stress: Effects on Human Health.

    abstract::Carotenoids are lipid-soluble pigments that are produced in some plants, algae, fungi, and bacterial species, which accounts for their orange and yellow hues. Carotenoids are powerful antioxidants thanks to their ability to quench singlet oxygen, to be oxidized, to be isomerized, and to scavenge free radicals, which p...

    journal_title:Marine drugs

    pub_type: 杂志文章,评审

    doi:10.3390/md13106226

    authors: Gammone MA,Riccioni G,D'Orazio N

    更新日期:2015-09-30 00:00:00

  • Antiproliferative Activity of Glycosaminoglycan-Like Polysaccharides Derived from Marine Molluscs.

    abstract::Despite the increasing availability of new classes of cancer treatment, such as immune- and targeted therapies, there remains a need for the development of new antiproliferative/cytotoxic drugs with improved pharmacological profiles that can also overcome drug resistant forms of cancer. In this study, we have identifi...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md16020063

    authors: Aldairi AF,Ogundipe OD,Pye DA

    更新日期:2018-02-15 00:00:00

  • Soft coral-derived lemnalol alleviates monosodium urate-induced gouty arthritis in rats by inhibiting leukocyte infiltration and iNOS, COX-2 and c-Fos protein expression.

    abstract::An acute gout attack manifests in the joint as dramatic inflammation. To date, the clinical use of medicinal agents has typically led to undesirable side effects. Numerous efforts have failed to create an effective and safe agent for the treatment of gout. Lemnalol-an extract from Formosan soft coral-has documented an...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md11010099

    authors: Lee HP,Huang SY,Lin YY,Wang HM,Jean YH,Wu SF,Duh CY,Wen ZH

    更新日期:2013-01-10 00:00:00

  • Immunomodulatory effects of domoic acid differ between in vivo and in vitro exposure in mice.

    abstract::The immunotoxic potential of domoic acid (DA), a well-characterized neurotoxin, has not been fully investigated. Phagocytosis and lymphocyte proliferation were evaluated following in vitro and in vivo exposure to assay direct vs indirect effects. Mice were injected intraperitoneally with a single dose of DA (2.5 micro...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md6040636

    authors: Levin M,Leibrecht H,Ryan J,Van Dolah F,De Guise S

    更新日期:2008-01-01 00:00:00

  • Aplysin sensitizes cancer cells to TRAIL by suppressing P38 MAPK/survivin pathway.

    abstract::TNF-related apoptosis-inducing ligand (TRAIL) is a tumor-selective apoptosis inducer and has been shown to be promising for treating various types of cancers. However, the application of TRAIL is greatly impeded by the resistance of cancer cells to its action. Studies show that overexpression of some critical pro-surv...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md12095072

    authors: Liu J,Ma L,Wu N,Liu G,Zheng L,Lin X

    更新日期:2014-09-25 00:00:00

  • Mechanisms of toxicity of 3-alkylpyridinium polymers from marine sponge Reniera sarai.

    abstract::Polymeric 3-alkylpyridinium salts (poly-APS) present in the marine sponge Reniera sarai show a broad spectrum of biological activities. They are lytic to erythrocytes and various other mammalian cells, enabling the transfection of the latter with alien DNA. Furthermore, they show inhibitory effects to marine bacteria ...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:

    authors: Turk T,Frangez R,Sepcić K

    更新日期:2007-11-13 00:00:00

  • Antithrombotics from the Sea: Polysaccharides and Beyond.

    abstract::Marine organisms exhibit some advantages as a renewable source of potential drugs, far beyond chemotherapics. Particularly, the number of marine natural products with antithrombotic activity has increased in the last few years, and reports show a wide diversity in scaffolds, beyond the polysaccharide framework. While ...

    journal_title:Marine drugs

    pub_type: 杂志文章,评审

    doi:10.3390/md17030170

    authors: Carvalhal F,Cristelo RR,Resende DISP,Pinto MMM,Sousa E,Correia-da-Silva M

    更新日期:2019-03-16 00:00:00

  • Isolation and Structure-Activity Relationship of Subergorgic Acid and Synthesis of Its Derivatives as Antifouling Agent.

    abstract::In this study, as part of our continuous search for environmentally-friendly antifoulants from natural resources, subergorgic acid (SA) was identified from the gorgonian coral Subergorgia suberosa, demonstrating non-toxic, significant inhibitory effects (EC50 1.25 μg/mL, LC50 > 25 μg/mL) against the settlement of Bala...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md17020101

    authors: Zhang J,Ling W,Yang Z,Liang Y,Zhang L,Guo C,Wang K,Zhong B,Xu S,Xu Y

    更新日期:2019-02-06 00:00:00

  • Core oligosaccharide of Plesiomonas shigelloides PCM 2231 (Serotype O17) lipopolysaccharide--structural and serological analysis.

    abstract::The herein presented complete structure of the core oligosaccharide of lipopolysaccharide (LPS) P. shigelloides Polish Collection of Microorganisms (PCM) 2231 (serotype O17) was investigated by (1)H, (13)C NMR spectroscopy, mass spectrometry, chemical analyses and serological methods. The core oligosaccharide is compo...

    journal_title:Marine drugs

    pub_type: 杂志文章

    doi:10.3390/md11020440

    authors: Maciejewska A,Lukasiewicz J,Kaszowska M,Man-Kupisinska A,Jachymek W,Lugowski C

    更新日期:2013-02-06 00:00:00