Oxygenated Geosmins and Plant-like Eudesmanes from
a Bacterial Mangrove Endophyte
Posted on 2020-06-19 - 16:07
Geosmin (1) is a microbial
terpene metabolite that
is responsible for the typical smell of soil and causes an off-odor
of food and water. Eudesmane sesquiterpenes are commonly found in
plant essential oils. Here we describe the discovery of four geosmin-type
metabolites, 7R-hydroxygeosmin (2),
3-oxogeosmin (3), 2R-hydroxy-7-oxogeosmin
(4), 5-deoxy-7β,9β-dihydroxygeosmin (5), the plant-like eudesmanes 4β,10α-eudesmane-5β,11-diol
(6) and (1S,5S,6S,7S,10S)-10α-eudesm-4(15)-ene-1α,6α-diol
(7), and the known 1(10)E,5E-germacradiene-2,11-diol (8) from a bacterial endophyte
(Streptomyces sp. JMRC:ST027706) of the mangrove
plant Bruguiera gymnorrhiza. By means of NMR, MS,
and ECD spectroscopy, all chemical structures as well as the absolute
configurations for the new compounds were elucidated. Compounds 2–5 represent the first geosmin-related
metabolites directly as bacterial natural products. The plant-derived
eudesmane-5β,11-diol (6) and (1S,5S,6S,7S,10S)-10α-eudesm-4(15)-ene-1α,6α-diol (7) are also now reported as bacterial products. The broad
antimicrobial activities of 6 against a suite of fungal
and bacterial pathogens including methicillin-resistant Staphylococcus
aureus suggest that this terpene could be an important active
principle of the medicinal plant Cymbopogon distans. The discovery of geosmin metabolites from one actinomycete indicated
that these bacteria could possess enzymes for modifying geosmin and
offer a possibility for bioremediation.
CITE THIS COLLECTION
DataCiteDataCite
3 Biotech3 Biotech
3D Printing in Medicine3D Printing in Medicine
3D Research3D Research
3D-Printed Materials and Systems3D-Printed Materials and Systems
4OR4OR
AAPG BulletinAAPG Bulletin
AAPS OpenAAPS Open
AAPS PharmSciTechAAPS PharmSciTech
Abhandlungen aus dem Mathematischen Seminar der Universität HamburgAbhandlungen aus dem Mathematischen Seminar der Universität Hamburg
ABI Technik (German)ABI Technik (German)
Academic MedicineAcademic Medicine
Academic PediatricsAcademic Pediatrics
Academic PsychiatryAcademic Psychiatry
Academic QuestionsAcademic Questions
Academy of Management DiscoveriesAcademy of Management Discoveries
Academy of Management JournalAcademy of Management Journal
Academy of Management Learning and EducationAcademy of Management Learning and Education
Academy of Management PerspectivesAcademy of Management Perspectives
Academy of Management ProceedingsAcademy of Management Proceedings
Academy of Management ReviewAcademy of Management Review
Ding, Ling; Hertweck, Christian (2020). Oxygenated Geosmins and Plant-like Eudesmanes from
a Bacterial Mangrove Endophyte. ACS Publications. Collection. https://doi.org/10.1021/acs.jnatprod.0c00304