An improved water-soluble/stereospecific biotransformation of aporphine alkaloids in Stephania epigaea to 4 R -hydroxyaporphine alkaloids by Clonostachys rogersoniana

Cai, Le; Dong, Jian-Wei; Zhao, Li‐Xing; Zhou, Hao; Xing, Yun; Li, Ying; Li, Zhenjie; Duan, Wei-He; Li, Xuejiao; Ding, Zhong‐Tao

doi:10.1016/j.procbio.2016.04.016

Cited by 18 publications

(5 citation statements)

References 34 publications

(43 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The absolute configuration (AC) of aporphine alkaloids has been established by optical rotatory dispersion [13], electronic circular dichroism [14,15] and X-ray diffraction [16,17]. These methods allowed to correlate the AC to their substitution pattern, specific rotation, or the sign of their Cotton effect [10], since it has been established that aporphines possessing two or more oxygenated substituents in ring D possess the S configuration, while aporphines with or without one substituents on that ring may have R or S configuration [18].…”

mentioning

confidence: 99%

Configurational Study of an Aporphine Alkaloid from Annona purpurea

Ontiveros-Rodríguez

Burgueño‐Tapia

Porras-Ramírez

et al. 2018

Natural Product Communications

View full text Add to dashboard Cite

Purpureine (1), norpurpureine (2), and 3-hydroxyglaucine (4) were isolated from the leaves of Annona purpurea. A vibrational circular dichroism study for the absolute configuration determination of 1 provides evidence for the mutually dependent atropisomerism, local chirality of the sole stereogenic center, and the geometry of the tetrahedral nitrogen atom in aporphine alkaloids. The observed change in the optical rotation sign between 2 and its hydrochloride 3 might explain why this compound has been reported as dextrorotatory and levorotatory from the same botanical source. Furthermore, 1 H and 13 C NMR spectra of 1, 2 and 4 were fully assigned for the first time.

show abstract

mentioning

confidence: 99%

Configurational Study of an Aporphine Alkaloid from Annona purpurea

Ontiveros-Rodríguez

Burgueño‐Tapia

Porras-Ramírez

et al. 2018

Natural Product Communications

View full text Add to dashboard Cite

show abstract

“…This raises the interesting question of whether Clonostachys is capable of catabolizing nerolidol and using it as a carbon source. Although such activity on terpenoids has not yet been identified, it was earlier demonstrated that Clonostachys can oxidatively biotransform plant-specialized metabolites of the alkaloid class through a cytochrome P450-based mechanism ( 73 ).…”

Section: Discussionmentioning

confidence: 99%

Terpenes modulate bacterial and fungal growth and sorghum rhizobiome communities

Chou,

Andersen,

Mechan Llontop

et al. 2023

Microbiol Spectr

View full text Add to dashboard Cite

Terpenes are among the oldest and largest class of plant-specialized bioproducts that are known to affect plant development, adaptation, and biological interactions. While their biosynthesis, evolution, and function in aboveground interactions with insects and individual microbial species are well studied, how different terpenes impact plant microbiomes belowground is much less understood. Here we designed an experiment to assess how belowground exogenous applications of monoterpenes (1,8-cineole and linalool) and a sesquiterpene (nerolidol) delivered through an artificial root system impacted its belowground bacterial and fungal microbiome. We found that the terpene applications had significant and variable impacts on bacterial and fungal communities, depending on terpene class and concentration; however, these impacts were localized to the artificial root system and the fungal rhizosphere. We complemented this experiment with pure culture bioassays on responsive bacteria and fungi isolated from the sorghum rhizobiome. Overall, higher concentrations (200 µM) of nerolidol were inhibitory to Ferrovibrium and tested Firmicutes. While fungal isolates of Penicillium and Periconia were also more inhibited by higher concentrations (200 µM) of nerolidol, Clonostachys was enhanced at this higher level and together with Humicola was inhibited by the lower concentration tested (100 µM). On the other hand, 1,8-cineole had an inhibitory effect on Orbilia at both tested concentrations but had a promotive effect at 100 µM on Penicillium and Periconia . Similarly, linalool at 100 µM had significant growth promotion in Mortierella , but an inhibitory effect for Orbilia . Together, these results highlight the variable direct effects of terpenes on single microbial isolates and demonstrate the complexity of microbe-terpene interactions in the rhizobiome. IMPORTANCE Terpenes represent one of the largest and oldest classes of plant-specialized metabolism, but their role in the belowground microbiome is poorly understood. Here, we used a “rhizobox” mesocosm experimental set-up to supply different concentrations and classes of terpenes into the soil compartment with growing sorghum for 1 month to assess how these terpenes affect sorghum bacterial and fungal rhizobiome communities. Changes in bacterial and fungal communities between treatments belowground were characterized, followed by bioassays screening on bacterial and fungal isolates from the sorghum rhizosphere against terpenes to validate direct microbial responses. We found that microbial growth stimulatory and inhibitory effects were localized, terpene specific, dose dependent, and transient in time. This work paves the way for engineering terpene metabolisms in plant microbiomes for improved sustainable agriculture and bioenergy crop production.

show abstract

“…In addition, multiple metabolite detection methods are utilized to screen transformed microbial strains. For instance, 307 strains of bacteria that could grow on LB medium containing 0.4 mg/mL of puerarin were isolated from local soils, HPLC were used to analyze the transformed cultures, Bacillus cereus NT02 was screened out from 307 strains of bacteria, which can transform puerarin into puerarin-600-O-phosphate [ 46 ]. A total of 45 caffeine-degrading moderate halophiles were enriched from hypersaline lakes and the biotransformation of caffeine to theobromine was examined by TLC and HPLC.…”

Section: Select Microbial Strains For Biotransformationmentioning

confidence: 99%

Multi-Level Optimization and Strategies in Microbial Biotransformation of Nature Products

Qin

Dong

2023

Molecules

View full text Add to dashboard Cite

Continuously growing demand for natural products with pharmacological activities has promoted the development of microbial transformation techniques, thereby facilitating the efficient production of natural products and the mining of new active compounds. Furthermore, due to the shortcomings and defects of microbial transformation, it is an important scientific issue of social and economic value to improve and optimize microbial transformation technology in increasing the yield and activity of transformed products. In this review, the aspects regarding the optimization of fermentation and the cross-disciplinary strategy, leading to the microbial transformation of increased levels of the high-efficiency process from natural products of a plant or microbial origin, were discussed. Additionally, due to the increasing craving for targeted and efficient methods for detecting transformed metabolites, analytical methods based on multiomics were also discussed. Such strategies can be well exploited and applied to the production of more efficient and more natural products from microbial resources.

show abstract

An improved water-soluble/stereospecific biotransformation of aporphine alkaloids in Stephania epigaea to 4 R -hydroxyaporphine alkaloids by Clonostachys rogersoniana

Cited by 18 publications

References 34 publications

Configurational Study of an Aporphine Alkaloid from Annona purpurea

Configurational Study of an Aporphine Alkaloid from Annona purpurea

Terpenes modulate bacterial and fungal growth and sorghum rhizobiome communities

Multi-Level Optimization and Strategies in Microbial Biotransformation of Nature Products

Contact Info

Product

Resources

About