Discovery, Characterization, and Analogue Synthesis of Bohemamine Dimers Generated by Non‐enzymatic Biosynthesis

Fu, Peng; Legako, Aaron G.; La, Scott; MacMillan, John B.

doi:10.1002/chem.201600024

Cited by 40 publications

(84 citation statements)

References 31 publications

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“…19 Additional research on another Bahamiancollected bacterial strain, Streptomyces spinoverrucosus SNB-032 by the same research group, yielded three new dimeric bohemamines, dibohemamines A-C 18-20 that were subsequently shown to be formed via a non-enzymatic process with formaldehyde, which was detected in the culture. 20 This mild dimerisation process was exploited to generate a series of semi-synthetic analogues for biological evaluation. Dibohemamines B and C displayed potent activity against the non-small cell lung cancer cell line A549, with IC 50 values of 140 and 145 nM, respectively.…”

Section: Marine-sourced Bacteriamentioning

confidence: 99%

“…Dibohemamines B and C displayed potent activity against the non-small cell lung cancer cell line A549, with IC 50 values of 140 and 145 nM, respectively. 20 Two separate studies on two different Streptomyces strains (one collected in Papua New Guinea and the other in China) each yielded new nahuoic acid metabolites. 21,22 Nahuoic acids B-E, along with the known polyketide natural product, nahuoic acid A 21, 23 were identied and reported from the Chinese strain.…”

Section: Marine-sourced Bacteriamentioning

confidence: 99%

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Marine natural products

et al. 2018

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Covering: 2016. Previous review: Nat. Prod. Rep., 2017, 34, 235-294This review covers the literature published in 2016 for marine natural products (MNPs), with 757 citations (643 for the period January to December 2016) 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 (1277 in 432 papers for 2016), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that led to the revision of structures or stereochemistries, have been included.

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Section: Marine-sourced Bacteriamentioning

confidence: 99%

Section: Marine-sourced Bacteriamentioning

confidence: 99%

Marine natural products

et al. 2018

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“…Both metabolites dibohemamines B (Fig. 8.4a) and C exhibited potent activity against lung cancer cells, with IC 50 values of 140 nM and 145 nM, respectively (Fu et al 2016). Another Streptomyces sp.…”

Section: Marine Bacteria: Widely Distributed Producers Of Promising Nmentioning

confidence: 98%

Secondary Metabolites of Marine Microbes: From Natural Products Chemistry to Chemical Ecology

Petersen

Kellermann

Schupp

2019

YOUMARES 9 - The Oceans: Our Research, Our Future

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Marine natural products (MNPs) exhibit a wide range of pharmaceutically relevant bioactivities, including antibiotic, antiviral, anticancer, or anti-inflammatory properties. Besides marine macroorganisms such as sponges, algae, or corals, specifically marine bacteria and fungi have shown to produce novel secondary metabolites (SMs) with unique and diverse chemical structures that may hold the key for the development of novel drugs or drug leads. Apart from highlighting their potential benefit to humankind, this review is focusing on the manifold functions of SMs in the marine ecosystem. For example, potent MNPs have the ability to exile predators and competing organisms, act as attractants for mating purposes, or serve as dye for the expulsion or attraction of other organisms. A large compilation of literature on the role of MNPs in marine ecology is available, and several reviews evaluated the function of MNPs for the aforementioned topics. Therefore, we focused the second part of this review on the importance of bioactive compounds from crustose coralline algae (CCA) and their role during coral settlement, a topic that has received less attention. It has been shown that certain SMs derived from CCA and their associated bacteria are able to induce attachment and/or metamorphosis of many benthic invertebrate larvae, including globally threatened reef-building scleractinian corals. This review provides an overview on bioactivities of MNPs from marine microbes and their potential use in medicine as well as on the latest findings of the chemical ecology and settlement process of scleractinian corals and other invertebrate larvae.

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“…For example, discoipyrroles A−D from the marine bacterium Bacillus hunanensis [7], were found to be originated from 4-hydroxysattabacin, 4-hydroxybenzaldehyde, and 2-amino benzoic acid through non-enzymatic reactions [8]. Dibohemamines A−C, three bohemamine dimers from a marine-derived Streptomyces sp., were found to be dimerized from the monomeric bohemamines and formaldehyde by a non-enzymatic reaction [9]. The formation of hybrids can greatly expand the chemical space of NPs, which will provide more compounds for bioactivity studies.…”

Section: Introductionmentioning

confidence: 99%

Circumdatin-Aspyrone Conjugates from the Coral-Associated Aspergillus ochraceus LCJ11-102

Fan

Ya-lin

et al. 2019

Marine Drugs

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Ochrazepines A−D (1−4), four new conjugates dimerized from 2-hydroxycircumdatin C (5) and aspyrone (6) by a nucleophilic addition to epoxide, were isolated from the fermentation broth of the coral-associated Aspergillus ochraceus strain LCJ11-102. Their structures including absolute configurations were determined based on spectroscopic analysis and chemical methods. Compounds 1−4 were also obtained by the semisynthesis from a nucleophilic addition of 2-hydroxycircumdatin C (5) to aspyrone (6). New compound 1 exhibited cytotoxic activity against 10 human cancer cell lines while new compounds 2 and 4 selectively inhibited U251 (human glioblastoma cell line) and compound 3 was active against A673 (human rhabdomyoma cell line), U87 (human glioblastoma cell line), and Hep3B (human liver cancer cell line) with IC50 (half maximal inhibitory concentration) values of 2.5–11.3 μM among 26 tested human cancer cell lines.

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Discovery, Characterization, and Analogue Synthesis of Bohemamine Dimers Generated by Non‐enzymatic Biosynthesis

Cited by 40 publications

References 31 publications

Marine natural products

Marine natural products

Secondary Metabolites of Marine Microbes: From Natural Products Chemistry to Chemical Ecology

Circumdatin-Aspyrone Conjugates from the Coral-Associated Aspergillus ochraceus LCJ11-102

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