Fungal endophytes from plants are an important source for discovery of novel bioactive natural products. In this study, five undescribed harziane diterpenoids with a 4/7/5/6 tetracyclic scaffold, harzianols F‒J and three known derivatives, were obtained from the liquid fermentation of an endophytic fungus Trichoderma atroviride B7, which was isolated from the healthy flower of a Lamiaceae plant Colquhounia coccinea var. mollis. Their structures were elucidated by comprehensive spectroscopic analyses and X-ray crystallographic diffraction in the case of harzianol F. Harzianol I exhibited significant antibacterial effect against the growth of Staphylococcus aureus (EC = 7.7 ± 0.8 μg/mL), Bacillus subtilis (EC = 7.7 ± 1.0 μg/mL), and Micrococcus luteus (EC = 9.9 ± 1.5 μg/mL). Meanwhile, cytotoxic activity of harzianol I against three cancer cell lines was also observed. A plausible biosynthetic pathway for harziane diterpenoids was proposed.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.phytochem.2019.112198 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Structure and Fungicidal Activity of Secondary Metabolites Isolated from b-3.
J Fungi (Basel)
October 2024
State Key Laboratory of Southwestern Chinese Medicine Resource, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China.
Article Synopsis
- Two new harziane diterpenes and five previously undescribed cyclonerane sesquiterpenes were identified from a b-3 extract, alongside three known compounds.
- Structural analysis was performed using HRESIMS and NMR techniques, confirming the absolute configuration of one compound through additional methods like ECD calculation.
- The isolated compounds demonstrated significant antifungal activity, with one compound achieving 100% inhibition of certain pathogenic fungi and showing potential for biopesticide development.
Diterpenoids with Antibacterial Activities from the Fungus .
J Agric Food Chem
July 2024
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
A new fusicoccane diterpenoid, harziaderma A (), two novel harziane diterpenoids, harzianones G and H ( and ), one revised harziane diterpenoid (), and two known diterpenoids ( and ) were isolated from the fungus and established via NMR, HRESIMS, Mo(OAc)-induced circular dichroism (ICD) and electronic circular dichroism (ECD) calculations. It is worth noting that compound represents the first instance of a fusicoccane-type diterpenoid derived from . The structure of furanharzianone B was revised to via careful spectroscopic analyses.
View Article and Find Full Text PDFA New Harziane Diterpene, Harziaketal A, and a New Sterol, Trichosterol A, from the Marine-Alga-Epiphytic Trichoderma sp. Z43.
Chem Biodivers
October 2023
Institute of Coastal Zone Research, Chinese Academy of Sciences, 264003, Yantai, P. R. China.
One new diterpene, harziaketal A (1), and one new highly degraded sterol, trichosterol A (2), along with three known compounds, including one diterpene, harzianone (3), and two steroids, (22E,24R)-5α,6α-epoxy-ergosta-8(14),22-dien-3β,7α-diol (4) and isoergokonin B (5), were isolated from the culture of the marine-alga-epiphytic fungus Trichoderma sp. Z43 by silica gel column chromatography (CC), Sephadex LH-20 CC, and preparative thin-layer chromatography (TLC). Their structures and relative configurations were assigned by nuclear magnetic resonance (NMR) and high resolution electrospray ionisation mass spectrometry (HR-ESI-MS) data, and the absolute configuration of 1 was established by X-ray diffraction.
View Article and Find Full Text PDFNovel Harziane Diterpenes from Deep-Sea Sediment Fungus sp. SCSIOW21 and Their Potential Anti-Inflammatory Effects.
Mar Drugs
December 2021
Shenzhen Key Laboratory of Marine Bioresource and Eco-Environmental Science, College of Life Sciences and Oceanography, Shenzhen University, Shenzhen 518060, China.
Five undescribed harziane-type diterpene derivatives, namely harzianol K (), harzianol L (), harzianol M (), harzianol N (), harzianol O (), along with two known compounds, hazianol J () and harzianol A () were isolated from the deep-sea sediment-derived fungus sp. SCSIOW21. The relative configurations were determined by meticulous spectroscopic methods including 1D, 2D NMR spectroscopy, and HR-ESI-MS.
View Article and Find Full Text PDFSynthetic Strategy for Construction of Highly Congested Tetracyclic Core (6-5-7-4) of Harziane Diterpenoids.
Org Lett
June 2021
State Key Laboratory of Chemical Oncogenomics and Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
The structurally intriguing tetracyclic core of complex harziane diterpenoid was constructed in 14 steps from commercially available 3-ethoxycyclohex-2-en-1-one. The key steps were a Mn/Cu-mediated oxidative 1,3-dicarbonyl radical cascade cyclization reaction, which diastereoselectively formed the core of dimethylbicyclo[3.2.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!