Eremophilane-Type Sesquiterpenoids From the Endophytic Fungus Rhizopycnis vagum and Their Antibacterial, Cytotoxic, and Phytotoxic Activities

Frontiers in Chemistry
Ali WangLigang Zhou

Abstract

Fourteen new eremophilane-type sesquiterpenoids, named rhizoperemophilanes A~N (1~14), together with eight known congeners, were isolated from the culture of the endophytic fungus Rhizopycnis vagum. The structures of the new compounds were elucidated by extensive spectroscopic analyses, as well as ECD calculations and the modified Mosher's method for the assignment of the absolute configurations. Rhizoperemophilane J (10) contains an uncommon C-4/C-11 epoxy ring, while rhizoperemophilane N (14) features an unprecedented 3-nor-eremophilane lactone-lactam skeleton. These metabolites were evaluated for their antibacterial, cytotoxic, and phytotoxic activities. Among them, compounds 11, 16, and 20 displayed antibacterial activities, while 14 showed selective cytotoxicity against NCI-H1650 and BGC823 tumor cells. Moreover, compounds 5, 6, 12, 13, 16, and 19 exhibited strong phytotoxic activities against the radicle elongation of rice seedlings.

References

Aug 21, 2014·Mini Reviews in Medicinal Chemistry·Chenjie HouFujiang Guo
Sep 23, 2014·Journal of Natural Products·Tijiang ShanMingan Wang
Jan 21, 2015·Journal of Natural Products·Paulina Del ValleRachel Mata
Mar 4, 2015·Journal of Natural Products·Charuwan DaengrotJariya Sakayaroj
Mar 18, 2015·Journal of Agricultural and Food Chemistry·Shiqiong LuLigang Zhou
Dec 17, 2015·Journal of Asian Natural Products Research·Wei-Hua YuanKuo-Hsiung Lee
Mar 2, 2016·Journal of Natural Products·Zhongbin ChengWenhan Lin
Jul 20, 2016·Journal of Natural Products·Jimei LiuJungui Dai
Aug 20, 2017·Biological Chemistry·Kamila Tomoko YuyamaWolf-Rainer Abraham
Oct 17, 2017·Journal of Natural Products·Yunbao LiuShishan Yu
Mar 7, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ali WangLigang Zhou

❮ Previous
Next ❯

Citations

May 1, 2021·Toxins·Dan XuLigang Zhou
Jul 3, 2021·Journal of Fungi·Rafael Dorighello CadamuroGislaine Fongaro
Sep 10, 2021·Applied Microbiology and Biotechnology·Xi LiuJun-Hong Wang

❮ Previous
Next ❯

Methods Mentioned

BETA
NMR
column chromatography
circular dichroism

Software Mentioned

TDDFT
MMFF
SpecDis

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.