Ophiobolin O and 6-Epi<i>-</i>Ophiobolin O, Two New Cytotoxic Sesterterpenes from the Marine Derived Fungus <i>Aspergillus</i> Sp

Zhang, Dahai; Fukuzawa, Seketsu; Satake, Masayuki; Li, Xianguo; Kuranaga, Takafumi; Niitsu, Ai; Yoshizawa, Kentaro; Tachibana, Kunihide

doi:10.1177/1934578x1200701102

Cited by 12 publications

(33 citation statements)

References 11 publications

(20 reference statements)

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“…were obtained from endophytic Aspergillus sp. (zoanthid Zoanthus sp., Ayamaru Cape, Amami Is., Japan) as moderate cytotoxins to P388 cells, 174 with ophiobolin O also inducing apoptosis and cell cycle arrest of MCF-7 cells through activation of MAPK signaling pathways. 175 Decalin derivative decumbenone C 189 was isolated from Aspergillus sulphureus (sediment, location unspecied) as a potent cytotoxin against SK-MEL-5 human melanoma cells.…”

Section: Marine-sourced Fungi (Excluding From Mangroves)mentioning

confidence: 99%

Marine natural products

et al. 2014

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This review covers the literature published in 2012 for marine natural products, with 1035 citations (673 for the period January to December 2012) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1241 for 2012), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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Section: Marine-sourced Fungi (Excluding From Mangroves)mentioning

confidence: 99%

Marine natural products

et al. 2014

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“…When comparing 3 with 4 , the stereochemistry at C6 practically did not change the cytotoxic activity in CLL [ 24 ], K562 [ 38 ] and HepG2 [ 38 ] cells ( Table 5 ). However, when comparing 33 with 34 , β-H significantly elevated cytotoxic effect in CLL cells [ 24 ], and the enhancement of activity in P388 [ 7 ] and TK-10 [ 19 ] cells was approximately 2 and 6 folds, respectively ( Table 5 ). Comparing 40 with 41 , β-H also slightly improved about 2 times of cytotoxic activity in murine P388 cells ( Table 5 ) [ 35 ].…”

Section: Cytotoxic Activitiesmentioning

confidence: 99%

“…The cytotoxic effects of the hydroxy group at C3 of 1 were 6.3 times lower, when comparing with 3 in Hela and KB cells [ 33 ]. However, the decreased effect was slighter when comparing 16 to 33 in P388 cells [ 7 ], 17 to 34 in HepG2 and KB cells [ 29 ], and 44 to 45 in HepG2 and KB cells [ 29 ], respectively ( Table 5 ). In CLL cells, hydroxy group at C3 visibly improved the cytotoxic effect when comparing 1 to 3 ( Table 5 ) [ 24 ].…”

Section: Cytotoxic Activitiesmentioning

confidence: 99%

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The Biological Activities of Sesterterpenoid-Type Ophiobolins

2017

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Ophiobolins (Ophs) are a group of tricarbocyclic sesterterpenoids whose structures contain a tricyclic 5-8-5 carbotricyclic skeleton. Thus far, 49 natural Ophs have been reported and assigned into A–W subgroups in order of discovery. While these sesterterpenoids were first characterized as highly effective phytotoxins, later investigations demonstrated that they display a broad spectrum of biological and pharmacological characteristics such as phytotoxic, antimicrobial, nematocidal, cytotoxic, anti-influenza and inflammation-promoting activities. These bioactive molecules are promising drug candidates due to the developments of their anti-proliferative activities against a vast number of cancer cell lines, multidrug resistance (MDR) cells and cancer stem cells (CSCs). Despite numerous studies on the biological functions of Ophs, their pharmacological mechanism still requires further research. This review summarizes the chemical structures, sources, and biological activities of the oph family and discusses its mechanisms and structure–activity relationship to lay the foundation for the future developments and applications of these promising molecules.

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“…The anti-biofilm activity of ophiobolin K and 6-epi-ophiobolin K were 4.1 and 65μM, respectively, also ophiobolin K showed antibiotic activity to mycobacterium smegmatis and mycobacterium bovis of 8.2 and 64 μM, respectively, but 6-epi-ophiobolin K was inactive [60][61] . )showed weak activity in these assays with MIC value larger than 100 μg mL -1 ( Table 3) [62] .…”

Section: Activities Of Ophiobolins and 6-epi Ophiobolinsmentioning

confidence: 99%

A Brief Review on Structure-Bioactivity Relationship Study of Ophiobolins and Derivatives

Ren¹,

Yang²,

Zhang³

et al. 2018

CMRJ

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Ophiobolins show a broad-spectrum inhibitory activity against nematodes, fungi, bacteria, and cytotoxic activity. Now many ophiobolin and their derivatives have been identified, nevertheless, there are few studies on structure-activity relationships for this class of compound. This review aims at summarizing published researches of ophiobolins and their derivatives, including the source, structure, bioactivity, the mode of action and the possible factors that cause the different bioactivity. In view of the fact that the activity of ophiobolins were generally higher than 6-epi-ophiobolins, ophiobolin O, K and 6-epi-ophiobolin O, K were studied as an example. The geometries, bond lengths, bond orders of the four compounds have been investigated at B3LYP/6-31+G(dip) level by density functional theory (DFT). The DFT analysis show that the ophinbolins steric of function group related to C (7) were much lower than 6-epi-ophiobolins, it suggested that C-H was the key bioactive group. The low steric reactive function group can be made to maximize contact with the target and thereby enhance the biological activity. It proposed a new pathway for the design and synthesis of the active molecule.

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Ophiobolin O and 6-Epi-Ophiobolin O, Two New Cytotoxic Sesterterpenes from the Marine Derived Fungus Aspergillus Sp

Cited by 12 publications

References 11 publications

Marine natural products

Marine natural products

The Biological Activities of Sesterterpenoid-Type Ophiobolins

A Brief Review on Structure-Bioactivity Relationship Study of Ophiobolins and Derivatives

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