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Home > Cytotoxic and antibacterial polyketide-indole hybrids synthesized from indole-3-carbinol by Daldinia eschscholzii
Cytotoxic and antibacterial polyketide-indole hybrids synthesized from indole-3-carbinol by Daldinia eschscholzii
Liping Lina,, Nan Jiangc, Huimin Wub, Yaning Meid, Jie Yange,Renxiang Tan
State Key Laboratory Cultivation Base for TCM Quality and Efficacy, Nanjing University of Chinese Medicine, Nanjing 210046, China
State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210023 China
School of Pharmacy, Nanjing Medical University, Nanjing 210029, China
Department of Clinical Laboratory, the First Affiliated Hospital of Nanjing Medical University, Nanjing 210029, China
Jiangsu Province Academy of Traditional Chinese Medicine, Nanjing 210028, China
Introduction
Indole alkaloids are an important class of organic molecules that contain one or more indole or indoline motifs. They widely distribute as secondary metabolites in bacteria, fungi, plants and animals1–3. Some indole alkaloids have been demonstrated to be cytotoxic (e.g., vintafolide and lestaurtinib4), analgesic (e.g., physostigmine5), antibacterial (e.g., dalesindole6), neuritogenic (e.g., manzamines7), immunosuppressive (e.g., sotrastaurin and tivantinib4), stem cell differentiation regulatory (e.g., kenpaullone and stauprimide8), and others. Therefore, the indole motif is present in diverse pharmacophores and many research groups have been motivated to discover more bioactive new alkaloids branded with such motifs9–11.
Polyketides are among the most diverse natural product categories12, but few polyketide-indole hybrids (PIHs) have been synthesized chemically or characterized from nature except for the tryptophan-derived cytochalasans3. A presumable underlying reason for the PIH rarity arises from the fact that the PIH synthesis faces a suite of challenges, such as the complicated reaction steps (including iterative/inevitable procedures for protection and deprotection) and/or the utilization of toxic/expensive reagents13,14.
Strategically, the generation of new PIHs usually includes cascade reactions such as C–C(N/O) bond formation15 and selective functionalization of unactivated aliphatic C(sp3)–H bonds16. However, these reactions largely proceed in harsh reaction conditions17. Thus, the greener approach is highly desired for the access to undescribed PIH molecules, and preferably, the PIH-constructing reactions could be completed in one pot in an eco-friendly manner.
Indole-3-carbinol (I3C, 1) is a cancer-preventive agent18 released via the degradation of indole glucosinolate in cruciferous vegetables19,20. After its oral administration to mice, 1 is metabolized into indole alkaloids including indole-3-carbaldehyde (I3A), indole-3-carboxylic acid (I3CA, 2), 1-(3-hydroxymethyl)-indolyl-3-indolylmethane (HI-IM), 3,3'-diindolylmethane (DIM), indolo[3,2b] carbazole (ICZ), and 2 (indol-3-ylmethyl)-3,3'-diindolylmethane (LTr1)21. The tumor therapeutic effect of DIM as a drug candidate under the phase III clinical trial (http://www.clinicaltrials.gov) could be alternatively formed by the decarboxylative Claisen condensation between I3A and I3CA (2), which was catalysed by 8-amino-7-oxononanoate synthase (AONS) in Daldinia eschscholzii6. Encouraged by the observation, we wondered whether 1 could be further metabolized and hybridized with polyketides, such as 1-(2,6-dihydroxyphenyl)-butan-1-one (3) from D. eschscholzii22,23, to afford new PIHs. The ketone and/or ketone-activated methylene might be able to form C–C (N/O) bonds with I3C-derived metabolites such as 2, I3A, and 3-methyleneindolenine (3-MEI)24. Herein, we present that the fungal polyketide reacts with the I3C metabolites most likely under the AONS catalysis to initialize the formation of indolchromins A (4) and B (5) (Scheme 1), two skeletally undescribed PIHs with potent antibacterial and cytotoxic activities.
Experimental
General experimental procedures
Optical rotations were recorded in MeOH on a Rudolph Research Analytical Autopol IV automatic polarimeter. IR spectra were acquired in KBr disks on a Nexus 870 FT–IR spectrometer. MS spectra were determined on an Agilent 6210 LC/TOF-MS spectrometer operating in a positive mode with direct infusion. NMR spectra were measured on a Bruker DRX400 or Varian Inova-600 NMR spectrometer with TMS as an internal standard. CD spectra were recorded on a JASCO J-810 Chirascan. HPLC separation was performed using Waters octadecylsilyl (ODS) column (250 mm 10 mm, 5 mm), a Hitachi pump L 7100, and a UV detector L-7400. Silica gel (200–300 mesh) for column chromatography (CC) and GF254 (10–20 mm) for thin layer chromatography (TLC) were produced by the Qingdao Marine Chemical Company, China. The ODS silica gel (50 mm) was purchased from YMC Co., Ltd., Japan, and Sephadex LH-20 from Pharmacia Biotech, Sweden. All drugs used herein as positive controls for bioassays were purchased from Sigma–Aldrich Co. Reagents and solvents used in the study were of analytical grade. Chiral HPLC separation was performed on a chiral column (CHIRALPAKs IA, Lot No. IA00CG-RE001, 250 mm 10 mm) with n-hexane/ethanol mixtures for different stereoisomers (Supporting Information Table S1). The human/animal bacterial pathogens were obtained from the First Affiliated Hospital of Nanjing Medical University (Nanjing, China), and the plant pathogenic bacteria were obtained from Nanjing Agricultural University (Nanjing, China).
Fungal cultivation and extraction
D. eschscholzii was cultured on Petri dishes in potato dextrose agar (PDA) medium at 28 for 3 days. The fresh mycelia taken from the grown fungal colony was inoculated into the flasks (always one-liter sized), each containing 400 mL of malt extract (ME) medium (20 g/L malt extract, 20 g/L sucrose and 1 g/L peptone). After a 2-day incubation at 28 with an agitation (200 rpm，DZ-900 agitator，Taicang Qiang Le Experimental Equipment Co., Ltd.), 20 mL of culture liquid was transferred as inoculating seed into each flask containing 400 mL of ME medium. At 24, 48, and 72 h after inoculation, I3C (1) was added into the flasks up to its concentration at 1.0 mmol/L. Cultivations were continued for the ensuing 10 days at 28 with agitation (200 rpm). The whole culture was extracted with ethyl acetate (EtOAc).
Preparation of intracellular fungal proteins (IFPs)
As described in previous studies6,36,37, the IFP was extracted at 4 1C from the fungal mycelia, which were collected by filtering with a Buchner funnel from the fungal culture. After washed twice with distilled water, frozen in liquid nitrogen, and ground into fine powder, the protein fraction was suspended in phosphate buffer saline (PBS, pH ¼ 7.0 throughout, unless stated otherwise), ultrasonicated for 30 min, and centrifuged at 11,486 g for 20 min. The supernatant was collected with its protein concentration quantified by using the BCA (bicinchoninic acid) Protein Assay Kit.
ECD computational details
The DFT at B3LYP/6–31G (d,p) level was employed to optimize the geometries of the studied systems, taking crystal structures as the original configurations. The solvent effect on the electronic structures of the concerned systems were evaluated by the quantum chemistry method through the polarizable continuum model (PCM, dielectric constant ε ¼ 32.64 for MeOH). The corresponding excited-state calculations were performed at the ground-state optimized geometries.
Time-dependent DFT in combination with PCM model (TD-DFT/PCM) with the same basis set was carried out to calculate the spinallowed excitation energy and rotatory strength of the lowest 100 excited states. The UV and ECD spectra were generated using the program SpecDis38 by applying a Gaussian band shape with the width of 0.20 eV, from oscillator strengths and dipole-velocity rotational strengths, respectively.
Relative energy computational details
DFT at the B3LYP/6–31þG (d,p) level was applied to optimize the geometries of the studied systems. Based on the optimized conformations, the vibrational frequency calculations using B3LYP method with 6–31þG(d,p) basis were performed to all stationary points to check whether the optimized geometry corresponded to a minimum or transition state and to obtain the Gibbs free energies. The solvent effects on the energies were evaluated by PCM model (dielectric constant ε ¼ 78.39 for H2O). All the calculations were performed with the Gaussian 09 program39.
Singlet crystal X-ray diffraction
Structures were solved by the direct method (SHELXS-97) and refined using full-matrix least-squares difference Fourier techniques. Crystallographic data in CIF format have been deposited in the Cambridge Crystallographic Data Centre [available free of charge at http://www.ccdc.cam.ac.uk/deposit or from the CCDC, 12 Union Road, Cambridge CB21EZ, UK; fax: (þ44) 1223-336-033;
or e-mail: deposit@ccdc.cam.ac.uk].
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