Glaucatotones A-I: Guaiane-type sesquiterpenoids from the roots of Lindera glauca with anti-inflammatory activity.

Glaucatotones A - I, nine new guaiane-type sesquiterpenoids, along with two reported compounds, namely (1ß,5ß)-1-hydroxyguaia-4(15),11(13)-dieno-12,5-lactone (10) and pseudoguaianelactone C (11), were isolated from the roots of Lindera glauca. The structures and absolute configurations of these compounds were elucidated by extensive spectroscopic analyses, single-crystal X-ray diffraction, and comparison of experimental and calculated electronic circular dichroism (ECD) data. Structurally, glaucatotone A (1) is characterized as a dihomosesquiterpenoid with an unprecedented 5/5/7/6 ring system. A pair of enantiomers, (±)-glaucatotone B (2a/2b), represent the first rearranged norsesquiterpenoid with a (cyclopentylmethyl)cyclohexane skeleton. 3 is defined as a dinorsesquiterpenoid possessing a 5/7/5 ring system. 4-6 are three guaiane-type norsesquiterpenoids. In vitro bioactivity, 2a selectively inhibited Bcap-37 with IC50 value of 5.60 µM, and 9 selectively inhibited Du-145 with IC50 value of 5.52 µM. The anti-inflammatory activity of 1-9 were tested, and of these compounds, 1, 2a, 2b and 7 exhibited potent inhibitory effects.

Sesquiterpenoids from the roots of Lindera glauca and their cytotoxicity activities.

The chemical investigation of the roots of Lindera glauca guided the isolation and identification of 3 new sesquiterpenoids, namely glaucatotones J-L (1-3), and one known congener, (1ß,5ß)-1-hydroxyguaia-4(15),11(13)-dieno-12,5-lactone (4). The structures of new compounds were established based on comprehensive spectrographic methods, mainly including 1D & 2D NMR and HRESIMS analyses, and the absolute configurations were further confirmed by the comparison of experimental and calculated electronic circular dichroism. The cytotoxicity activities of isolates were evaluated, and the results showed that they have moderate cytotoxic activities.

Super low-frequency electric field measurement based on Rydberg atoms.

We demonstrate the measurement of super low-frequency electric field using Rydberg atoms in an atomic vapor cell with inside parallel electrodes, thus overcoming the low-frequency electric-field-screening effect at frequencies below a few kHz. Rydberg electromagnetically induced transparency (EIT) spectra involving 52D5/2 state is employed to measure the signal electric field. An auxiliary DC field is applied to improve the sensitivity. A DC Stark map is demonstrated, where the utilized 52D5/2 exhibits mj = 1/2, 3/2, 5/2 Stark shifts and splittings. The mj = 1/2 state is employed to detect the signal field because of its larger polarizability than that of mj = 3/2, 5/2. Also, we show that the strength of the spectrum is dependent on the angle between the laser polarizations and the electric field. With optimization of the applied DC field to shift the mj = 1/2 Rydberg energy level to a high sensitivity region and the laser polarizations to obtain the maximum mj = 1/2 signal, we achieve the detection of the signal electric field with a frequency of 100 Hz down to 214.8 µV/cm with a sensitivity of 67.9 µV cm-1Hz-1/2, and the linear dynamic range is over 37 dB. Our work extends the measurement frequency of Rydberg sensors to super low frequency with high sensitivity, which has the advantages of high sensitivity and miniaturization for receiving super low frequency.

Targeting Inhibition of Notch 1 Can Promote mTOR Signaling Pathway in Tumor-Related Macrophage to Regulate the Development of Ovarian Cancer.

Background: Ovarian cancer is the leading cause of death linked to gynecological cancers. Notch1, as an important component of Notch signaling, plays an important role in a variety of cancers. This study aims to discuss the mechanisms through which Notch 1 influences the development of ovarian cancer. Methods: To design and establish the short hairpin (sh) RNA for targeting Notch 1, we transfected THP-1 cells (one of the human macrophagic lines). The cells were divided into shRNA negative control (NC) group and the Notch 1 shRNA group. The CoC1 cells and THP-1 cells (human mononuclear macrophages) are co-cultured, which are injected into the nude mice subcutaneously based on proposition. The sizes of tumors and their volumes are observed through HE staining. Flow cytometry is used to sort out macrophages from subcutaneous tumors of nude mice, whose protein-related expression is detected through western blot. Then the NC group and the Notch 1 shRNA group in the co-culture system are treated with PI3K/mTOR Inhibitor-13 sodium (200 nM) for 48h and then co-cultured with human endothelial cell lines HUVEC, CoC1, and THP-1 to test the tube-forming capacity of HUVEC cells in each group to detect the protein-related expression in THP-1 cells using western blot. Results: It is seen that the Notch 1 shRNA group includes a significantly larger tumor size, decreased relative expression, and the obvious increase of the relative protein expression in p-PI3K, p-mTOR, HIF1α, and VEGF compared with the NC group. Through tube-forming experiments, the Notch1 shRNA group significantly increased the number of HUVEC tubes. However, after the use of PI3K/mTOR Inhibitor-13 sodium, the number of tubes decreased in the NC and Notch1 shRNA groups, and there is no significant discrepancy in comparison to the NC group. The in vitro western blotting results indicate no obvious variation of Notch 1's relative protein expression in both the NC group and Notch 1 shRNA group after the use of PI3K/mTOR Inhibitor-13 sodium, while the relative protein expression of p-PI3K, p-mTOR, HIF1α, and VEGF was significantly reduced and there was no significant difference. Conclusion: This study found that specific knockout of Notch 1 in tumor-associated macrophages will promote the activation of the PI3K/mTOR signaling pathway and the expression of HIF1α and VEGF, thus promoting angiogenesis and the development of ovarian cancer. Thus, this study provides insight into novel prognostic biomarkers and therapeutic targets for the treatment and research of ovarian cancer.

Establishment of Male and Female Eucommia Fingerprints by UPLC Combined with OPLS-DA Model and Its Application.

Eucommia ulmoides Oliver is a dioecious plant, which plays an important role in traditional Chinese medicine. However, there has not yet been any research on male and female E. ulmoides. The UPLC fingerprints and OPLS-DA approach were able to quickly and easily identify and quantify E. ulmoides and differentiate between the male and female fingerprints. In this study, we optimized the UPLC conditions and analyzed them to investigate fingerprints of twenty-four extracts of Eucommiae Cortex (EC) and twenty-four extracts of Eucommiae Folium (EF) under optimal conditions. It was demonstrated that thirteen and twelve substances were possible chemical markers for EC and EF male and female discrimination and that the level of these markers - chlorogenic acid and protocatechuic acid - was many times higher in male than in female. This approach offered a reference for quality control and precise treatment of male and female E. ulmoides in the clinic.

Molecular Dynamics Study on the Diffusion Behavior of Water Molecules and the Dielectric Constant of Vegetable/Mineral Oil Blends.

Insulating oil plays a crucial role in internal insulation of oil-impregnated transformers. It has been demonstrated in a variety of experimental studies that mineral oil (MO) and vegetable oil (VO) can be blended in different ratios to improve insulation properties; however, the mechanisms underlying this phenomenon remain unclear. In this study, a molecular dynamics (MD) simulation approach was used to investigate diffusion of water molecules in VO/MO blends and dielectric constants of a mixture. The results show that the diffusion coefficient of water molecules is negatively correlated with the proportion of VO; thus, addition of VO helps to improve the insulation properties of a mixture. Due to introduction of strong polar functional groups, a decrease in the diffusion behavior of water molecules can be attributed to an increase in the interaction energy and formation of hydrogen bonds between water molecules and the mixed oil system. There is a direct correlation between the dielectric constant of a mixture and VO content; however, it is very sensitive to water content. The presence of strong polar water molecules or functional groups in a mixture leads to an increase in the dielectric constant, which results in a reduction in insulating properties. Accordingly, presence of polar groups plays an important role in determining the insulating properties of a mixture. To increase the insulation performance of a mixture, it is important to consider the diffusion-inhibiting and dielectric effects of the stronger polar groups in vegetable oil compared to those in mineral oil.

Rydberg atom-based AM receiver with a weak continuous frequency carrier.

We demonstrate an atom-based amplitude-modulation (AM) receiver for digital communication with a weak continuous frequency carrier using a Rydberg AC Stark effect in a vapor cell and achieve the operating carrier frequency continuously from 0.1 GHz to 5 GHz at a single Rydberg state. A strong local oscillator (LO) field ELO acts as a gain to shift the Rydberg level to a high sensitivity region, and a weak carrier field ECarr keeps the same frequency with the LO field. The digital baseband signals are encoded onto the ECarr using the amplitude modulation technique with the different modulation frequency. The response of Rydberg atom to the baseband signal is probed via a Rydberg electromagnetically induced transparency (EIT). The measured instantaneous bandwidth of the system is about 230 kHz. To demonstrate the performance of our system for an actual communication, we consider a color image as an example, the received image displays that the bit error rate (BER) is less than 5% when the maximum data transfer rate is about 238 kbps. Meanwhile, our system shows the weak carrier field of ECarr ≥ 13.52 µV/cm can be used for the practical communication with BER less than 5%. Our works break the limitation that EIT-AT based atomic receivers only operate at the near resonant frequencies of the Rydberg transitions, making this emerging of quantum technology close to the practical application with high sensitivity and broad bandwidth.

Hydrocarbon stapling modification of peptide alyteserin-2a: Discovery of novel stapled peptide antitumor agents.

Alyteserin-2a (ILGKLLSTAAGLLSNLNH2 ) is isolated from the skin exudates of midwife toad and has a wide range of biological applications. However, the use of alyteserin-2a as an antitumor agent is limited due to its structural flexibility. In this study, a series of stapled peptides were prepared through hydrocarbon stapling modification without destroying the key residues, and their chemical and biological properties were further evaluated for enhancing the application potential of alyteserin-2a in the field of antitumor drugs development. Among them, alyteserin-2a-Sp3 displayed significant improvement in helicity levels, protease resistance, and antitumor activity compared to that of the template peptide alyteserin-2a, indicating that alyteserin-2a-Sp3 had a potential to become a lead compound for the development of novel antitumor drugs. This study confirms the important effect of hydrocarbon stapling strategy on the secondary structure, hydrolase stability, and biological activity of alyteserin-2a.

Evaluation of sparing the pronator quadratus for volar plating of distal radius fractures: a retrospective clinical study.

BACKGROUND: The most commonly used approach for distal radius fractures is the traditional Henry approach. However, it requires an intraoperative incision of the pronator quadratus (PQ) muscle, which results in a series of complications if the repair of the PQ fails. AIM: The objective of this study was to investigate the efficacy of sparing the pronator quadratus for volar plating of the distal radius fractures. METHODS: Seventy-six patients who suffered from distal radius fractures of types 23-B, 23-C1, and 23-C2 as per the AO Foundation and Orthopaedic Trauma Association (AO/OTA) classification were treated with volar locking plate fixation using either the PQ muscle incision and repair (group A, n = 39) or the PQ muscle preservation approach (group B, n = 37). Intraoperative index, postoperative efficacy and complications of patients were recorded and evaluated. RESULTS: All patients were followed up for more than one year after surgery. All fractures achieved union. There were significant differences in mean operative time, mean intraoperative blood loss, and mean fracture healing time between the two groups. Still, there were no significant differences in limb function scores between the two groups at the 12-month postoperative follow-up. Outcomes assessed at 1 week, 1 month, and 3 months after surgery demonstrated significant differences in the mean range of motion and pain-related visual analog scale (VAS) between the two groups. As the range of motion and grip strength increased, the VAS scores decreased, and there was no significant difference between the two groups at 12 months postoperatively. Although tendon irritation and delayed carpal tunnel syndrome were more common in group A than in group B (7.6% vs. 0% and 5.1% vs. 0%, respectively), the differences were not statistically significant. CONCLUSION: The modified Henry approach with sparing pronator quadratus muscle has no significant advantage in the range of wrist motion and upper limb function in the late stage. Nevertheless, the intraoperative placement of the plate under the pronator quadratus muscle can shorten the operation time, reduce intraoperative bleeding, reduce early postoperative pain, promote early activity, and improve the patient's quality of life. It is recommended that the pronator be preserved at the time of surgery.

One-stage posterior surgery combined with anti-Brucella therapy in the management of lumbosacral brucellosis spondylitis: a retrospective study.

BACKGROUND: This study aimed to assess the clinical efficacy of one-stage posterior surgery combined with anti-Brucella therapy in the treatment of lumbosacral brucellosis spondylitis (LBS). METHODS: From June 2010 to June 2020, the clinical and radiographic data of patients with LBS treated by one-stage posterior surgery combined with anti-Brucella therapy were retrospectively analyzed. The visual analogue scale (VAS), Japanese Orthopaedic Association (JOA) and Oswestry Disability Index scores (ODI) were used to evaluate the clinical outcomes. Frankel's classification system was employed to access the initial and final neurologic function. Fusion of the bone grafting was classified by Bridwell's grading system. RESULTS: A total of 55 patients were included in this study with a mean postoperative follow-up time of 2.6 ± 0.8 years (range, 2 to 5). There were 40 males and 15 females with a mean age of 39.8 ± 14.7 years (range, 27 to 57). The Brucella agglutination test was ≥ 1:160 in all patients, but the blood culture was positive in 43 patients (78.1%). A statistical difference was observed in ESR, CRP, VAS, ODI, and JOA between preoperative and final follow-up (P < 0.05). Neurological function was significantly improved in 20 patients with preoperative neurological dysfunction after surgery. According to Bridwell's grading system, the fusion of bone grafting in 48 cases (87.2%) was defined as grade I, and grade II in 7 cases (12.7%). None of the infestation recurrences was observed. CONCLUSION: One-stage posterior surgery combined with anti-Brucella therapy was a practical method in the treatment of LBS with severe neurological compression and spinal sagittal imbalance.

Proversilins A-E, Drimane-Type Sesquiterpenoids from the Endophytic Aspergillus versicolor.

Five new drimane-type sesquiterpenoids, named proversilins A-E (1-5), were isolated from the endophytic fungus Aspergillus versicolor F210 isolated from the bulbs of Lycoris radiata. Their structures and absolute configurations were characterized by extensive spectroscopic analysis, including 1D and 2D NMR and HRESIMS data, comparison of experimental and calculated electronic circular dichroism data, and X-ray crystallography. Proversilins B-E (2-5) represent the first examples of natural products featuring an N-acetyl-ß-phenylalanine moiety. Compounds 3 and 5 inhibited the growth of HL-60 cells with IC50 values of 7.3 and 9.9 µM, respectively.

Bioassay-Directed Isolation of Antibacterial Metabolites from an Arthropod-Derived Penicillium chrysogenum.

Bioassay-directed isolation of secondary metabolites from an extract of Penicillium chrysogenum TJ403-CA4 isolated from the medicinally valuable arthropod Cryptotympana atrata afforded five new and 10 known compounds (1-15). All the compounds (except 14) belong to a minor class of highly rigid 6-5-5-5-fused tetracyclic cyclopiane-type diterpenes known to be exclusively produced by members of the Penicillium genus. The structures and absolute configurations of the new compounds (1-5) were elucidated by extensive spectroscopic analyses, including HRESIMS and 1D and 2D NMR, single-crystal X-ray diffraction, and comparison of the experimental electronic circular dichroism data. Compounds 1 and 2 represent the first examples of cyclopianes bearing a C-20 carboxyl group; compound 3 represents the first example of a cyclopiane with a gem-hydroxymethyl group; compound 4 represents the second example of a cyclopiane bearing a hydroxy group at C-7; compound 5 represents the first example of a cyclopiane bearing a hydroxy group at C-8. Compounds 2 and 3 exhibited activity against MRSA, with MIC values of 4.0 and 2.0 µg/mL, respectively. In addition, the structure-antibacterial activity relationship (SAR) of compounds 1-15 is discussed.

Reisolation and Configurational Reinvestigation of Cottoquinazolines E-G from an Arthropod-Derived Strain of the Fungus Neosartorya fischeri.

The reported fumiquinazoline-related alkaloids cottoquinazolines E-G (1-3) were reisolated from solid cultures of the fungus Neosartorya fischeri, which was isolated from the medicinal arthropod Cryptotympana atrata. The unresolved issues regarding the absolute configurations (for cottoquinazolines E and F) prompted a reinvestigation of the configurations for all three compounds, as enabled by extensive spectroscopic methods, comparisons of experimental electronic circular dichroism data, and X-ray crystallography. In addition, cottoquinazoline F (2) showed significant antibacterial activity against ESBL-producing Escherichia coli, Acinetobacter baumannii, Pseudomonas aeruginosa, and Enterococcus faecalis with MIC values of 8, 32, 32, and 16 µg/mL, respectively.

Fusicoccane-derived diterpenoids with bridgehead double-bond-containing tricyclo[9.2.1.03,7]tetradecane ring systems from Alternaria brassicicola.

Fusicoccane-derived diterpenoids bearing a unique bridgehead double-bond-containing tricyclo[9.2.1.03,7]tetradecane (5-9-5 ring system) core skeleton represent a rarely reported class of rearranged terpenoids, which traced back to fusicoccanes with a classical dicyclopenta[a,d]cyclooctane (5-8-5 ring system) core skeleton via a crucial Wagner-Meerwein rearrangement reaction. In this research, alterbrassicenes B-D (1-3), three new rearranged fusicoccane diterpenoids bearing a rare bridgehead double-bond-containing tricyclo[9.2.1.03,7]tetradecane core skeleton, together with two known congeners, brassicicenes O and K (4 and 5), were isolated from the modified cultures of fungus Alternaria brassicicola. Their structures were elucidated by comprehensive analyses of the NMR and HRESIMS data, and the absolute configurations of 1 and 4 were further confirmed via a combination of 13C NMR and ECD calculations and single-crystal X-ray diffraction analysis (Cu Kα). Interestingly, alterbrassicene B (1) represented the second case of bridgehead C-10-C-11 double-bond-containing natural products with a bicyclo[6.2.1]undecane core skeleton, and also featured an undescribed oxygen bridge between C-6 and C-14 to construct an unprecedentedly caged tetracyclic system. Alterbrassicenes B-D showed moderate cytotoxic activity against certain human tumor cell lines with IC50 values in the range of 15.87-36.85 µM.

Fusaresters A-E, new γ-pyrone-containing polyketides from fungus Fusarium sp. Hungcl and structure revision of fusariumin D.

Marine-derived fungi have been regarded as an under-explored and promising reservoir of structurally novel and bioactive natural products. In this study, five new γ-pyrone-containing polyketides, fusaresters A-E (1-5), were isolated and identified from the culture extracts of a marine-derived fungus Fusarium sp. Hungcl. The structures of compounds 1-5 were elucidated on the basis of their HRESIMS and NMR spectroscopic data as well as 13C NMR calculation and electronic circular dichroism (ECD) analyses. Remarkably, the structure of fusariumin D was revised to (9S*,11S*)-3. All these isolates were tested for the cytotoxicity against seven human cancer cell lines, including SW480, HL-60, A549, MCF-7, HepG2, HeLa and SMMC-7721, and the inhibitory activity against protein tyrosine phosphatase 1B (PTP1B). The results revealed that only compound 2 showed a weak inhibition rate of 56% at 40 µM.

Acute ischemic stroke in young adults with tuberculous meningitis.

BACKGROUND: Ischemic stroke is a common complication in patients with tuberculous meningitis (TBM), which is associated with poor clinical outcome. However, risk factors of stroke in TBM patients were not fully understood, especially in those young adults. Therefore, the aim of our study was to identify risk factors for acute ischemic stroke in young adults with TBM. METHODS: TBM patients (18 to 50 years) without cerebral vascular risk factors were prospective recruited between Feb 2014 and Dec 2017. Patients were defined as stroke group and non-stroke group by brain magnetic resonance imaging (MRI). Demographic characteristics, clinical presentations, cerebrospinal fluid (CSF) examination, basal meningeal enhancement, hydrocephalus, tuberculoma and clinical outcome were compared between two groups. Binary logistic regression was performed to determine risk factors for acute ischemic stroke in young TBM patients. RESULTS: Fifty-two patients with TBM were included and 12 (23.1%) patients were in stroke group. Patients in stroke group were older. Clinical presentations were comparable between two groups except headache was more common in TBM patients with stroke. In CSF examination, TBM patients with stroke had higher CSF white blood cell. By MRI, patients in stroke group were more likely to have basal meningeal enhancement but less likely to present tuberculoma. Compared to non-stroke group, patients in stroke group had worse short-term clinical outcome. In logistic regression, age (OR = 1.297; 95%CI 1.067, 1.576), CSF white blood cell (OR = 1.023; 95%CI 1.005, 1.042) and basal meningeal enhancement (OR = 23.913; 95%CI 1.398, 408.975) were independent risk factors for stroke. However, tuberculoma (OR = 0.005; 95%CI 0.000, 0.254) was negative related with stroke. CONCLUSIONS: About a quarter of young adults with TBM have acute ischemic stroke which may lead to poor clinical outcome. Age, CSF white blood cell and basal meningeal enhancement are risk factors for acute ischemic stroke in young adults with TBM.

HPLC-DAD-Directed Isolation of Linearly Fused Prenylated Indole Alkaloids from a Soil-Derived Aspergillus versicolor.

An HPLC-DAD-directed chemical investigation of the soil-derived fungus Aspergillus versicolor QC812 resulted in the isolation and identification of eight new linearly fused prenylated indole alkaloids, asperversiamides I-P (1-8), along with a congener, asperversiamide H (9). Their structures and absolute configurations were determined by spectroscopic analysis including HRESIMS and 1D and 2D NMR, electronic circular dichroism analysis, and single-crystal X-ray diffraction. Asperversiamide I (1), the first diketopiperazine derived from d-proline and l-tryptophan, possesses an unprecedented C-11-spiro-fused 6/6/5/5/6/5 hexacyclic ring system. Asperversiamide J (2) is the first linearly fused 6/6/5 tricyclic prenylated indole alkaloid to be reported. 1 and 2 showed moderate inhibitory activities against HeLa cells with IC50 values of 7.3 and 6.4 µM, respectively.

Antimicrobial Dolabellanes and Atranones from a Marine-Derived Strain of the Toxigenic Fungus Stachybotrys chartarum.

Three new dolabellane-type diterpenoids (1-3) and three new atranones (4-6) were isolated and identified from a marine-derived strain of the toxigenic fungus Stachybotrys chartarum. The planar and relative structures of 1-6 were elucidated using extensive spectroscopic methods, and their absolute configurations were fully confirmed via single-crystal X-ray diffraction analysis. Structurally, compounds 2 and 3 have a 1,14-seco dolabellane-type diterpenoid skeleton; compound 4 is the first C23 atranone featuring a propan-2-one motif linked to a dolabellane-type diterpenoid by a carbon-carbon bond; compound 5 represents the first example of a C24 atranone with a 2-methyltetrahydrofuran-3-carboxylate motif fused to a dolabellane-type diterpenoid at C-5-C-6. In an in vitro antimicrobial activity assay, compound 2 was active against Acinetobacter baumannii and Enterococcus faecalis with MIC values of 16 and 32 µg/mL, respectively, while compound 4 exhibited significant inhibitory activities against Candida albicans, Enterococcus faecalis, and methicillin-resistant Staphylococcus aureus (MRSA) with MIC values of 8, 16, and 32 µg/mL, respectively.

Bipolaricins A-I, Ophiobolin-Type Tetracyclic Sesterterpenes from a Phytopathogenic Bipolaris sp. Fungus.

A preliminary phytochemical investigation on the EtOAc extracts of the fungus Bipolaris sp. TJ403-B1 resulted in the identification of 12 ophiobolin-type phytotoxins (1-12), including nine new ones, termed bipolaricins A-I (1-9). The structures of 1-9 were elucidated via spectroscopic data (including HRESIMS and 1D and 2D NMR) and single-crystal X-ray diffraction (Cu Kα) analyses. All of the isolated compounds were tested in terms of HMG-CoA reductase inhibitory, anti-inflammatory, and cytotoxic activities. Compound 10 showed HMG-CoA reductase inhibitory activity (IC50 = 8.4 ± 0.4 µM), and 2, 3, and 10-12 showed significant inhibitory potency against lipopolysaccharide (LPS)-induced nitric oxide production, with IC50 values in the range of 5.1 ± 0.3 to 20 ± 1 µM. Further experiments showed that 10 could significantly inhibit the production of IL-1ß, RANTES, MIP-1ß, and TNF-α as well as enhance the release of IL-13 in macrophages through the inhibition of HO-1 induction as well as the NF-κB pathway. These findings provide a scientific rationale for an anti-inflammatory therapeutic and a template for a new HMG-CoA reductase inhibitor to produce a potential anti-hyperlipidemia agent.

Asperversiamides, Linearly Fused Prenylated Indole Alkaloids from the Marine-Derived Fungus Aspergillus versicolor.

Asperversiamides A-H (1-8), eight linearly fused prenylated indole alkaloids featuring an unusual pyrano[3,2- f]indole unit, were isolated from the marine-derived fungus Aspergillus versicolor. The structures and absolute configurations of these compounds were elucidated by extensive spectroscopic analyses, single-crystal X-ray diffraction, electronic circular dichroism (ECD) calculations, and optical rotation (OR) calculations. The relative configuration of C-21 of iso-notoamide B was herein revised, and a new methodology for preliminarily determining if the relative configuration of the bicyclo[2.2.2]diazaoctane moiety of a spiro-bicyclo[2.2.2]diazaoctane-type indole alkaloid is syn or anti was developed. The anti-inflammatory activities of the isolated compounds were all tested, and of these compounds, 7 exhibited a potent inhibitory effect against iNOS with an IC50 value of 5.39 µM.