Evidence map›Paper›PMID 32816319›Full record

ArticleChembiochem : a European journal of chemical biology2021

Fungal Epithiodiketopiperazines Carrying α,β-Polysulfide Bridges from Penicillium steckii YE, and Their Chemical Interconversion.

Guangde Jiang, Peilan Zhang, Ranjala Ratnayake, Guang Yang, Yi Zhang, Ran Zuo, Magan Powell, José C Huguet-Tapia, Khalil A Abboud, Long H Dang and 9 more

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Chembiochem : a European journal of chemical biology, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

4 citing papers in PubMed.

  1. Fusaric Acid Analogs and Dimers from Marine-DerivedJournal of natural products · 2026
    Article
  2. Review
  3. Article
  4. Review
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

19 authors.

Guangde JiangDepartment of Medicinal Chemistry, Center for Natural Products, Drug Discovery and Development, University of Florida, Gainesville, FL, 32610, USA.
Peilan ZhangDepartment of Medicinal Chemistry, Center for Natural Products, Drug Discovery and Development, University of Florida, Gainesville, FL, 32610, USA.
Ranjala RatnayakeDepartment of Medicinal Chemistry, Center for Natural Products, Drug Discovery and Development, University of Florida, Gainesville, FL, 32610, USA.
Guang YangDepartment of Medicinal Chemistry, Center for Natural Products, Drug Discovery and Development, University of Florida, Gainesville, FL, 32610, USA.
Yi ZhangDepartment of Medicinal Chemistry, Center for Natural Products, Drug Discovery and Development, University of Florida, Gainesville, FL, 32610, USA.
Ran ZuoDepartment of Medicinal Chemistry, Center for Natural Products, Drug Discovery and Development, University of Florida, Gainesville, FL, 32610, USA.
Magan PowellDepartment of Medicinal Chemistry, Center for Natural Products, Drug Discovery and Development, University of Florida, Gainesville, FL, 32610, USA.
José C Huguet-TapiaDepartment of Plant Pathology, University of Florida, Gainesville, 32611, FL, USA.
Khalil A AbboudDepartment of Chemistry, University of Florida, Gainesville, 32611, FL, USA.
Long H DangDepartment of Medicinal Chemistry, Center for Natural Products, Drug Discovery and Development, University of Florida, Gainesville, FL, 32610, USA.
Max TeplitskiSoil and Water Science Department, University of Florida, Gainesville, 32610, FL, USA.
Valerie PaulSmithsonian Marine Station at Ft., Pierce, 701 Seaway Drive, Ft. Pierce, 34949, FL, USA.
Rui XiaoDepartments of Aging and Geriatric Research, Pharmacology and Therapeutics, Center for Smell and Taste, University of Florida, Gainesville, 32610, FL, USA.
K H AhammadDepartment of Medicinal Chemistry, Center for Natural Products, Drug Discovery and Development, University of Florida, Gainesville, FL, 32610, USA.
Uz ZamanDepartment of Pharmaceutical Sciences, Daniel K. Inouye College of Pharmacy, University of Hawai'i at Hilo, Hilo, Hawaii, 96720, USA.
Zhenquan HuWarshel Institute for Computational Biology, The Chinese University of Hong Kong,Shenzhen, Guangdong, 518172, P. R. China.
Shugeng CaoDepartment of Pharmaceutical Sciences, Daniel K. Inouye College of Pharmacy, University of Hawai'i at Hilo, Hilo, Hawaii, 96720, USA.
Hendrik LueschDepartment of Medicinal Chemistry, Center for Natural Products, Drug Discovery and Development, University of Florida, Gainesville, FL, 32610, USA.
Yousong DingDepartment of Medicinal Chemistry, Center for Natural Products, Drug Discovery and Development, University of Florida, Gainesville, FL, 32610, USA.ORCID 0000-0001-8610-0659

Funding

Novel Targeted Anticancer Agents from Marine CyanobacteriaR01CA172310 · NCI · UNIVERSITY OF FLORIDA · PI HENDRIK LUESCH · 2013 to 2026
$5.8M
NIH Equipment Supplement to R35GM128742R35GM128742 · NIGMS · UNIVERSITY OF FLORIDA · PI Yousong Ding · 2018 to 2026
$3.4M
Development of Complex Natural Product Libraries and Multidimensional Anticancer Screening PlatformsR50CA211487 · NCI · UNIVERSITY OF FLORIDA · PI RATNAYAKE, RANJALA · 2016 to 2020
$440k
NCI NIH HHS R01 CA172310NCI NIH HHS R50 CA211487NIGMS NIH HHS R35 GM128742
6 · The paper itself

Abstract

Some fungal epithiodiketopiperazine alkaloids display α,β-polysulfide bridges alongside diverse structural variations. However, the logic of their chemical diversity has rarely been explored. Here, we report the identification of three new (2, 3, 8) and five known (1, 4-7) epithiodiketopiperazines of this subtype from a marine-derived Penicillium sp. The structure elucidation was supported by multiple spectroscopic analyses. Importantly, we observed multiple nonenzymatic interconversions of these analogues in aqueous solutions and organic solvents. Furthermore, the same biosynthetic origin of these compounds was supported by one mined gene cluster. The dominant analogue (1) demonstrated selective cytotoxicity to androgen-sensitive prostate cancer cells and HIF-depleted colorectal cells and mild antiaging activities, linking the bioactivity to oxidative stress. These results provide crucial insight into the formation of fungal epithiodiketopiperazines through chemical interconversions.

Indexed as

DiketopiperazinesMolecular StructurePenicilliumSulfidesDiketopiperazinespolysulfideSulfidesantiagingbiosynthesischemical transformationcytotoxicityepithiodiketopiperazine

Identifiers

PMID32816319
PMCPMC7895331

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Registered trials

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.