Jia-Peng Wang

Spirostanol steroids from the roots of Allium tuberosum

Three new spirostanol saponins named tuberosines A-C (1-3), together with three known ones tuberoside O (4), 25(S)-Schidigera-saponin D5 (5), and shatavarin IV (6) were isolated from the roots of Allium tuberosum. Their structures were established on the basis of extensive spectroscopic analyses. Whereas compounds 5 and 6 exhibited potent antibacterial activities against Bacillus subtilis (32 μg/mL) and Escherichia coli (16 μg/mL), the new saponin 2 showed only moderate antibacterial activities against these pathogens. The relationship between the antibacterial activities and the structures of these saponins are described.

A new C20-diterpenoid alkaloid from the lateral roots of Aconitum carmichaeli

Abstract A new C20-diterpenoid alkaloid carmichaedine (1) and six known alkaloids (2–7) were isolated from the lateral roots of Aconitum carmichaeli. Their structures were established on the basis of extensive spectroscopic analyses. Compound 1 exhibited potent antibacterial activity against Bacillus subtilis with minimum inhibitory concentration of 8 μg/mL.

Production of a new tetracyclic triterpene sulfate metabolite sambacide by solid-state cultivated Fusarium sambucinum B10.2 using potato as substrate.

The aim of this work is to explore integracide analogues from secondary metabolites of microorganisms. A new tetracyclic triterpene sulfate was produced by solid-state fermentation (SSF) with Fusarium sambucinum B10.2. The tetracyclic triterpene sulfate was identified as (3S,5R,10S,11S,12S,13R,17R,20R)-4,4-dimethylergosta-8,14,24-triene-3,11,12-triol-12-acetate, 3-sulfate on the basis of HRESIMS, NMR and electronic circular dichroism (ECD) spectra and named sambacide (1). The antibacterial and antifungal assays of sambacide (1) showed significant antibacterial activities against Staphylococcus aureus and Escherichia coli. The fermentation conditions including culture media, fermentation temperature and time, were optimized. And potato was selected as the fermentation substrate, 28°C was used as the fermentation temperature, and 20-days fermentation time was determined for F. sambucinum-SSF to produce sambacide (1) with a high yield of 19.04±0.82g/kg. This paper provides an efficient approach to produce the antibacterial and antifungal agent sambacide (1) in a very high yield.

Fermentation of Illigera aromatica with Clonostachys rogersoniana producing novel cytotoxic menthane-type monoterpenoid dimers

Illigera aromatica, a medicinal liana, was fermented with Clonostachys rogersoniana. Two novel menthane-type monoterpenoid dimers, dimericilligerates E (1) and F (2) were isolated from the fermented material. Their structures were identified by 1D/2D NMR, electric circular dichroism, derivatization, and Moshers method. A novel elimination reaction that formed a benzene ring from a menthane moiety afforded derivative 1a, which possesses more resolved NMR signals than the dimeric monoterpenoid, dimericilligerate E (1). The determination of 1a verified the estimation of 1. Compounds 1 and 2 showed potent cytotoxic activities; especially, 1 possessed significant activities against the liver hepatocellular carcinoma cell line (SMMC-7721) with an IC50 value of 3.89 ± 0.23 μM. Three novel precursors, dimericilligerates A–C (3–5), were identified by HPLC-MS and isolated from the original I. aromatica. This paper presents a novel class of monoterpenoid dimers and suggests that C. rogersoniana-fermented I. aromatica is effective to produce cytotoxic dimeric monoterpenoids from inactive original materials.

A novel sesquiterpene derivative with a seven-membered B ring from Illigera aromatica

Abstract A novel sesquiterpene derivative with a seven-membered B ring, illigerine (1), along with four known compounds, 1-epi-chiliophyllin (2), 3,4-dihydroxyphenethyl alcohol (3), coniferyl alcohol (4) and phenylpropionic acid (5), were isolated from Illigera aromatica S. Z. Huang et S. L. Mo. Their structures were identified by 1D/2D NMR, HRESIMS and electronic circular dichroism spectra and the cytotoxic activity and inhibitory effect of NO production in LPS-stimulated RAW264.7 were also evaluated. This is the first report of sesquiterpene isolated from the genus Illigera.

Peniroquesines A–C: Sesterterpenoids Possessing a 5–6–5–6–5-Fused Pentacyclic Ring System from Penicillium roqueforti YJ-14

Three novel sesterterpenes, peniroquesines A-C, possessing an 5-6-5-6-5-fused pentacyclic ring system, were isolated from the fungus Penicillium roqueforti YJ-14 by solid fermentation. Their structures were initially investigated in detail by NMR spectra and HR-ESI-MS and were further confirmed by chemical reaction experiments as well as by X-ray analysis. Furthermore, a plausible biosynthetic pathway was investigated by isotope-labeling experiments.

A new menthane-type monoterpenoid from fermented Illigera aromatica with Clonostachys rogersoniana 828H2

Abstract A new menthane-type monoterpenoid, illigerate E (1), as well as two known ones, (1R*,3R*,4S*,6R*)-6,8-dihydroxymenthol (2) and cis-4-hydroxy-5-(1-hydroxy-1-methylethyl)-2-methyl-2-cyclohexene-1-one (3), were isolated from fermented Illigera aromatica with Clonostachys rogersoniana 828H2. Their structures were identified by HRESIMS and 1D/2D NMR spectra. Their inhibitory effects of NO production in RAW 264.7 macrophages were estimated.