Pretrichodermamides D–F from a Marine Algicolous Fungus Penicillium sp. KMM 4672

Yurchenko, Anton N.; Smetanina, O. F.; Ivanets, Elena V; Kalinovsky, Anatoly I.; Khudyakova, Yuliya V.; Киричук, Н. Н.; Popov, Roman S.; Bokemeyer, Carsten; Amsberg, Gunhild von; Chingizova, Ekaterina A.; Afiyatullov, Shamil Sh.; Dyshlovoy, Sergey A.

doi:10.3390/md14070122

Cited by 41 publications

(47 citation statements)

References 20 publications

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“…This is analogous to the pattern of activity seen with 2 and its analogues. While mechanistic studies were not performed with N-methylpretrichodermamide B ( 19 ), 23 we hypothesize that given the similarities in structure and IC 50 values to 2 , 19 may have the same mechanism of action and that the pretrichodermamide may be a precursor of 2 , ultimately leading to DNA damage. This hypothesis is supported by the facile conversion of pretrichodermamide A to trichodermamide A, as previously demonstrated by Seephonkai et al 25 Further studies will be necessary to elucidate the exact mechanism of DNA damage induced by 2 and determine whether 2 or its related compounds are suitable for in vivo antitumor studies.…”

Section: Resultsmentioning

confidence: 99%

Cytotoxicity and Mechanism of Action of the Marine-Derived Fungal Metabolite Trichodermamide B and Synthetic Analogues

et al. 2017

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The trichodermamides are modified dipeptides isolated from a wide variety of fungi, including Trichoderma virens. Previous studies reported that trichodermamide B (2) initiated cytotoxicity in HCT-116 colorectal cancer cells, while trichodermamide A (1) was devoid of activity. We recently developed an efficient total synthesis for the trichodermamides A–C (1–3). Multiple intermediates and analogues were produced, and they were evaluated for biological effects to identify additional structure activity relationships and the possibility that a simplified analogue would retain the biological effects of 2. The antiproliferative effects of 18 compounds were evaluated and the results show that 2 and four other compounds are active in HeLa cells, with IC50 values in the range of 1.4–21 μM. Mechanism of action studies of 2 and the other active analogues revealed different spectra of activity. At the IC85 concentration, 2 caused S-phase accumulation and cell death in HeLa cells, suggesting response to DNA double strand breaks. The analogues did not cause S-phase accumulation or induction of DNA damage repair pathways, consistent with an alternate mode of action. The mechanistic differences are hypothesized to be due to the chlorohydrin moiety in 2 which is lacking in the analogues, which could form a DNA-reactive epoxide.

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Section: Resultsmentioning

confidence: 99%

Cytotoxicity and Mechanism of Action of the Marine-Derived Fungal Metabolite Trichodermamide B and Synthetic Analogues

et al. 2017

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“…[81] Anyway, this strain produced several new unusual compounds which exhibited cytotoxic and antioxidant properties. [41,43] Marine fungi of Vietnamese coastal waters have not been explored, and this field in the marine fungal natural products chemistry began to develop thanks the expeditions.…”

Section: Discussionmentioning

confidence: 99%

“…N-methylpretrichodermamide B (107) showed cytotoxic activity against human prostate cancer cells of the 22Rv1 line, which are resistant to targeted hormone therapy. [41] In addition, the known 6-methylcurvulinic acid (108), anserinone B (109), (+)-formylanserinone B (110), 3,5-dimethyl-8-methoxy-3,4-dihydro-1H-isochromen-6-ol (111) and quinolactacide (112) were isolated from this strain and tested for cytotoxic, hemolytic and radical-scavenging activities. Anserinone B (109) and formylanserinone B (110) showed toxicity against Ehrlich carcinoma cells with EC 50 values of 46.1 and 35.7 μM, respectively, and the isochromene derivative 111 scavenged DPPH free radicals by 35 %.…”

Section: Microfilamentous Fungimentioning

confidence: 99%

Achievements in the Study of Marine Low‐Molecular Weight Biologically Active Metabolites from the Vietnamese Territorial Waters as a Result of Expeditions aboard the Research Vessel ‘Akademik Oparin’ (2004–2017)

Yurchenko

Minh

et al. 2019

Chemistry & Biodiversity

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Until 2004, the secondary metabolites of marine organisms of the Vietnamese territorial waters had been studied very poorly. Only four new compounds were isolated from 1977 to 2003. Joint Russian‐Vietnamese expeditions aboard the research vessel ‘Akademik Oparin’ made it possible to study in detail the chemical diversity of marine micro‐ and macroorganisms. As a result of five expeditions, more than 250 low‐molecular weight natural compounds, including 117 new metabolites, were isolated from marine invertebrates and microfilamentous fungi. Their biological activities, such as cytotoxic, cytoprotective, and antioxidant activities, were investigated. Information about the structure and biological activity of the compounds, the source for their isolation and the geographical location of the objects is summarized in this review.

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“…[ 18 ], and a marine algicolous fungus ( Penicillium sp. KMM4672) [ 19 ]. All three studies showed that compound 32 , which contains chlorine, exhibited significant cytotoxicity, wherein it reduced the viability of L5178Y mouse lymphoma cells, human prostate cancer 22Rv1 cells, PC-3 cells, LNCaP cells, and brine shrimps (IC 50 = 2, 0.51, 5.11, 1.76, and 4.8 μM, respectively; while kahalalide F, docetaxel, and colchicine were employed as positive controls with IC 50 values of 4.3, 0.013, 0.015, 0.004, and 8.1 μM, respectively).…”

Section: Alkaloidsmentioning

confidence: 99%

Marine-Derived Penicillium Species as Producers of Cytotoxic Metabolites

Liu

Song

et al. 2017

Marine Drugs

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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.

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Pretrichodermamides D–F from a Marine Algicolous Fungus Penicillium sp. KMM 4672

Cited by 41 publications

References 20 publications

Cytotoxicity and Mechanism of Action of the Marine-Derived Fungal Metabolite Trichodermamide B and Synthetic Analogues

Cytotoxicity and Mechanism of Action of the Marine-Derived Fungal Metabolite Trichodermamide B and Synthetic Analogues

Achievements in the Study of Marine Low‐Molecular Weight Biologically Active Metabolites from the Vietnamese Territorial Waters as a Result of Expeditions aboard the Research Vessel ‘Akademik Oparin’ (2004–2017)

Marine-Derived Penicillium Species as Producers of Cytotoxic Metabolites

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