Multimodal inhibitory effect of matcha on Porphyromonas gingivalis.

Porphyromonas gingivalis has been associated with progression of periodontitis, characterized by inflammation and destruction of periodontal tissues. Here, we report that matcha, a product of Camellia sinensis, hampers the adherence and survival of P. gingivalis through multiple tactics. Matcha extract (ME) inhibited the growth not only of P. gingivalis but also of Prevotella nigrescens and Fusobacterium nucleatum, while it did not inhibit growth of nine species of oral streptococci and Aggregatibacter actinomycetemcomitans. ME-mediated P. gingivalis growth inhibition was characterized by both morphological and physiological changes at the bacterial envelope, which were accompanied by nano-particle formation and decreased membrane fluidity/permeability without loss of membrane integrity. ME also triggered autoaggregation of P. gingivalis in a major fimbriae (FimA)-dependent manner. In addition, adherence of P. gingivalis was dramatically inhibited by ME, irrespective of fimbriae. Furthermore, a structure-activity relationship study tested a series of catechins isolated from ME and identified the pyrogallol-type B-ring of catechins as essential for P. gingivalis growth inhibition. In a clinical study to assess the microbiological and therapeutic effects of matcha mouthwash in patients with periodontitis, the P. gingivalis number in saliva was significantly reduced by matcha mouthwash compared to the pre-intervention level. A tendency toward improvement in probing pocket depth was observed in the matcha group, although the difference was not statistically significant. Taken together, we present a proof of concept, based on the multimodal inhibitory effect of matcha against P. gingivalis, and that matcha may have clinical applicability for prevention and treatment of periodontitis. IMPORTANCE: Periodontitis, a multifactorial inflammatory disease of the oral cavity, results in alveolar bone destruction, and is a major cause of tooth loss of humans. In addition, emerging evidence has demonstrated associations between periodontitis and a wide range of other chronic inflammation-driven disorders, including diabetes mellitus, preterm birth, cardiovascular disease, aspiration pneumonia, rheumatoid arthritis, cognitive disorder, and cancer. In the present study, we report that matcha, a product of Camellia sinensis, hampers Porphyromonas gingivalis, a major periodontal pathobiont, in not only a series of in vitro experiments but also a pilot intervention clinical trial of patients with periodontitis, in which matcha mouthwash statistically significantly reduced the P. gingivalis number in saliva, as compared to the pre-intervention level. Taken together, we suggest that matcha may have clinical applicability for prevention and treatment of periodontitis.

Effects of Remimazolam on Intracellular Calcium Dynamics in Myotubes Derived from Patients with Malignant Hyperthermia and Functional Analysis of Type 1 Ryanodine Receptor Gene Variants.

Remimazolam is a novel general anesthetic and its safety in patients with malignant hyperthermia (MH) is unknown. We used myotubes derived from the skeletal muscle of patients with MH to examine the response to ryanodine receptor 1 (RYR1) agonist and remimazolam in MH-susceptible patients. Patients underwent muscle biopsy for the Ca2+-induced Ca2+ release (CICR) rate test, a diagnostic tool for MH in Japan. Ten patients had myotubes obtained from skeletal muscle cultures, and the genes associated with malignant hyperthermia in these patients were analyzed. The EC50 of caffeine, cresol, and remimazolam to induce intracellular calcium concentration change were compared between myotubes from CICR-negative genetic test patients and myotubes from other patients. Eight of the ten were CICR-positive, five of whom had RYR1 causative gene mutations or variants. Two patients had CICR-negative genetic tests, and as expected had the highest EC50 (the concentration of a drug that gives a half-maximal response) in response to caffeine, 4CmC and remimazolam. Three patients had a positive CICR but no known variants in RYR1 or CACNA1S (voltage-gated calcium channel subunit alpha1S). Myotubes in these patients had significantly lower EC50s for all agents than myotubes in CICR-negative patients. When myotubes from a patient who was CICR-negative and had no gene variant were used as a control, myotubes from CICR-positive patients were more hyper-responsive than controls to all stimulants used. The EC50 for remimazolam was lowest for myotubes from CICR-positive, RYR1-mutant patients, at 206 µM (corresponding to 123 µg/mL). The concentration was more than 80-times higher than the clinical concentration. RYR1 gene variants in R4645Q and W5020G were shown to be causative gene mutations for MH. Intracellular calcium in myotubes from MH patients are elevated at high concentrations of remimazolam but not at clinically used concentrations of remimazolam. Remimazolam appears to be safe to use in patients with MH.

The unique activity of saponin: Induction of cytotoxicity in HTLV-1 infected cells.

Infection with the retrovirus human T-cell leukemia virus type 1 (HTLV-1) sometimes causes diseases that are difficult to cure. To find anti-HTLV-1 natural compounds, we opted to screen using the HTLV-1-infected T-cell line, MT-2. Based on our results, an extract of the pulp/seeds of Akebia quinata Decaisne fruit killed MT-2 cells but did not affect the Jurkat cell line that was not infected with virus. To determine the active ingredients, seven saponins with one-six sugar moieties were isolated from A. quinata seeds, and their activities against the two cell lines were examined. Both cell lines were killed in a similar manner by Akebia saponins A and B. Further, Akebia saponins D, E, PK and G did not exhibit cytotoxicity. Akebia saponin C had a similar activity to the extract found in the screening. This compound was found to enhance Gag aggregation, induce the abnormal cleavage of Gag, suppress virion release, and preferentially kill HTLV-1 infected cells; however, their relationship remains elusive. Our findings may lead to the development of new therapies for infectious diseases based on the removal of whole-virus-infected cells.

Garlicnin B1, an Active Cyclic Sulfide from Garlic, Exhibits Potent Anti-Inflammatory and Anti-Tumor Activities.

This study aimed to investigate the pharmacological activities of garlicnin B1, a cyclic sulfide compound found abundantly in garlic and structurally similar to onionin A1, which has been shown to possess strong anti-tumor effects. In vitro studies demonstrated that garlicnin B1 significantly reduced intracellular reactive oxygen species triggered by hydrogen peroxide in colon cancer cells. In a mouse colitis model induced by dextran sulfate sodium, garlicnin B1 at a low dose (5 mg/kg) remarkably ameliorated the symptoms and pathological progression. Additionally, garlicnin B1 exhibited considerable tumoricidal activity with an IC50 value of ~20 µM, as observed in cytotoxicity assays. In vivo experiments using the mouse sarcoma S180 transplanted model and the azoxymethane (AOM) or DSS-induced colon cancer model showed that garlicnin B1 effectively suppressed tumor growth in a dose-dependent manner, with marked inhibition at 80 mg/kg. These results suggest that garlicnin B1 has diverse functions that could be achieved by carefully manipulating the dosing regimen. We anticipate that garlicnin B1 has the potential to be used beneficially in the future for the treatment of cancer and inflammatory diseases, although further studies are warranted to elucidate its mechanisms of action.

Onionin A inhibits small-cell lung cancer proliferation through suppressing STAT3 activation induced by macrophages-derived IL-6 and cell-cell interaction with tumor-associated macrophage.

Tumor-associated macrophage (TAM)-derived IL-6 is involved in small-cell lung cancer (SCLC) progression and chemoresistance via the activation of signal transducer and activator of transcription 3 (STAT3) in the tumor microenvironment. This study aimed to identify natural compounds that suppress cell-cell interactions between TAMs and SCLC cells by inhibiting STAT3 activation. We used a library of natural compounds to identify candidate agents possessing anti-SCLC effects by inhibiting macrophage-induced tumor proliferation. SBC-3 and SBC-5, human SCLC cell lines, were used for in vitro experiments. Furthermore, we assessed the efficacy of these candidate agents in a murine xenograft model of human SCLC. Among the natural compounds examined, onionin A (ONA) inhibited IL-6-induced STAT3 activation and SCLC cell proliferation. ONA also reduced the secretion of IL-6 from macrophages and interfered with the direct effect of cell-cell interactions between macrophages and SCLC cells. Furthermore, ONA administration suppressed tumor progression in a tumor-bearing mouse model. ONA was identified as the most useful candidate for targeting cell-cell interactions between cancer cells and TAMs for anti-SCLC therapy.

Dual Inhibitory Activity of Petroselinic Acid Enriched in Fennel Against Porphyromonas gingivalis.

Increasing evidence has shown that a major periodontal pathobiont, Porphyromonas gingivalis, triggers oral dysbiosis leading to deterioration not only of periodontal health, but also of several systemic conditions. In the present study we identified remarkable anti-P. gingivalis activity of Foeniculum vulgare (fennel), an herbal plant used in Asian cuisine as well as in traditional medicine, by screening of 92 extracts prepared from 23 edible plants. The n-hexane-extracted fennel (HEF) showed a rapid lethal action toward P. gingivalis, while it was rather ineffective with a wide range of other oral commensal bacterial species. Morphological analysis using both high-speed atomic force microscopy and field emission scanning electron microscopy revealed that a low concentration of HEF (8 µg/mL) resulted in formation of protruding nanostructures composed of outer membrane vesicle (OMV)-like particles, while a high concentration of HEF (64 µg/mL) induced bacteriolysis with overproduction of OMVs with unusual surface properties. Interestingly, HEF treatment resulted in deprivation of two outer membrane transporter proteins, RagA and RagB, which is essential for nutrient acquisition in P. gingivalis, by extracellularly releasing RagA/RagB-enriched OMVs. Furthermore, HEF showed gingipain-inhibitory activity toward both arginine-specific (Rgps) and lysine-specific (Kgp) gingipains, resulting in blocking oral epithelial cell rounding and the subsequent detachment from culture dishes. Finally, we isolated petroselinic acid as a major bactericide as well as a gingipain inhibitor through a bioassay-guided fractionation of HEF. Taken together, our findings suggest clinical applicability of HEF and petroselinic acid for periodontitis therapy to eliminate P. gingivalis and its major virulence factors on the basis of the dual anti-P. gingivalis activity, i.e., rapid bacteriolysis and gingipain inhibition.

A new steroidal glycoside from the fruits of Solanum myriacanthum.

A new cholestane-type steroidal glycoside, solamyriaside A (1), was isolated from the fruits of Solanum myriacanthum Dunal (Solanaceae), along with two known steroidal glycosides, namely, solaviaside A (2) and aculeatiside A (3), and three known steroidal alkaloid glycosides, namely, solamargine (4), khasianine (5) and solasonine (6), which were isolated for the first time from this plant. Based on spectroscopic data as well as chemical evidence, 1 was determined to be 3-O-α-L-rhamnopyranosyl-(1→2)-O-[α-L-rhamnopyranosyl-(1→4)]-ß-D-glucopyranosyl-22R,25R-cholest-5-ene-3ß,16α,22,26-tetraol 26-O-ß-D-glucopyranoside. The cytotoxic activity of 1-6 against HL-60 human promyelocytic leukaemia cells was examined. Compounds 4-6 showed cytotoxic activity. Among them, 4 exhibited the strongest activity with an IC50 value of 4.64 ± 0.17 µM, similar to the activity of cisplatin, a positive control.

Curry Leaf Triggers Cell Death of P. gingivalis with Membrane Blebbing.

Periodontal disease has become a serious public health problem, as indicated by accumulating evidence that periodontal disease is not only a major cause of tooth loss but is also associated with various systemic diseases. The present study assessed the anti-bacterial activities of three herbal products (curry leaf, clove, and cinnamon) against Porphyomonas gingivalis, a keystone pathogen for periodontal diseases. The curry leaf extract (CLE) showed the strongest growth inhibitory activity among them, and the activity was maintained even after extensive heat treatment. Of note, while clove and cinnamon extracts at sub-minimum inhibitory concentrations (sub-MICs) significantly enhanced the biofilm formation of P. gingivalis, CLE at sub-MIC did not have any effect on the biofilm formation. The MIC of CLE against P. gingivalis was higher than those against a wide range of other oral bacterial species. P. gingivalis cells were completely killed within 30 min after treatment with CLE. Spatiotemporal analysis using high-speed atomic force microscopy revealed that CLE immediately triggered aberrant membrane vesicle formation on the bacterial surface. Bacterial membrane potential assay revealed that CLE induced depolarization of the bacterial membrane. Taken together, these findings suggest the mechanism behind early bactericidal activity of CLE and its therapeutic applicability in patients with periodontal diseases.

Thiolane-type sulfides from garlic, onion, and Welsh onion.

In this paper, we review our work in the last 10 years wherein we examined the sulfides in the acetone extracts of garlic (Allium sativum), onion (A. cepa), and Welsh onion (A. fistulosum), obtained and characterized the structures of new sulfides, three 3,4-dimethylthiolane-type sulfides from onion and Welsh onion, respectively, and four acyclic-type, nine 3,4-dimethyl- thiolane-type, four 2-methylthiolane (and thiane)-type, two 1,2-dithiolane-type, and two 2-oxothiolane-type sulfides, together with (E)-ajoene and one kujounin-type sulfide from garlic. During this process, structural corrections were made in onionin A group, garlicnin A, and garlicnin B group in some 3,4-dimethylthiolane-type sulfides. Next, hypothetical pathways for the production of the aforementioned sulfides were proposed. Furthermore, it was revealed that a typical 3,4-dimethylthiolane-type sulfide, onionin A1 obtained from onion, having the isomeric structure of garlicnin B1 obtained from garlic, decreased tumor proliferation and controlled tumor metastasis. These results showed that onionin A1 is an effective agent for controlling tumors, and that the antitumor effects observed in vivo are likely caused by reversing the antitumor immune system. Activation of the antitumor immune system by onionin A1 might be an effective adjuvant therapy for patients with osteosarcoma, ovarian cancer and other malignant tumors.

Supramolecular Assembly of Hybrid Pt(II) Porphyrin/Tomatine Analogues with Different Nanostructures and Cytotoxic Activities.

A simple strategy for synthesizing supramolecular hybrids was developed for the preparation of bioavailable nanohybrid photosensitizers by assembling visible-light-sensitive Pt(II) meso-tetrakis(4-carboxyphenyl)porphyrinporphyrin (PtTCPP)/tomatine analogues. The hybrids were self-assembled into nanofibrous or nanosheet structures approximately 3-5 nm thick and several micrometers wide. α-Tomatine generated a unique fibrous vesicle nanostructure based on intermolecular interactions, while dehydrotomatine generated nanosheet structures. Nanoassembly of these fibrous vesicles and sheets directly affected the properties of the light-responsive photosensitizer for tumor photodynamic therapy (PDT), depending on the nanostructure of the hybrid PtTCPP/tomatine analogues. The cytotoxicity of PtTCPP to cancer cells under photoirradiation was significantly enhanced by a tomatine assembly with a fibrous vesicle nanostructure, attributable to increased incorporation of the drug into cells.

Novel technique for identification of the pulmonary intersegmental plane using manual jet ventilation during pulmonary segmentectomy.

INTRODUCTION: For successful pulmonary segmentectomy, the identification of boundaries between segments is important. Previous measures include tracing the intersegmental vessels by staining with a dye via the affected pulmonary artery or bronchus and inflating with oxygen via a high frequency ventilator. However, problems with these methods have been reported. AIM: We developed a novel method using a manual jet ventilator (MJV) and investigated its efficacy in identification of the pulmonary intersegmental plane. MATERIAL AND METHODS: Patients underwent MJV for pulmonary segmentectomy in the period from January 2013 to December 2017 at our institution. The patients' characteristics, resected segments, availability of clear resection planes, and complications associated with MJV from medical records were investigated. A questionnaire survey was conducted with the surgeons on the effectiveness of lung segment identification using MJV. RESULTS: Of 199 cases of planned pulmonary segmentectomy, 171 cases with descriptions of identified intersegmental planes were analyzed. Of these, 152 (89%) cases showed a clear boundary. There were 19 cases where the exact boundaries were not clearly identified, but segmentectomy was still performed. Furthermore, we found that identification of the right upper lobes was difficult (p = 0.0028). A subjective questionnaire was answered by the 12 surgeons who performed the procedures. All 12 responded that MJV was very effective or effective regarding clarity, safety, shorter identification time, and shorter resection time. CONCLUSIONS: MJV enabled surgeons to more easily and safely identify the pulmonary intersegmental plane, thereby suggesting that MJV has clinical significance during pulmonary segmentectomy.

Drosera tokaiensis extract containing multiple phenolic compounds inhibits the formation of advanced glycation end-products.

The accumulation of advanced glycation end-products (AGEs) correlates with aging and accompanies the onset of age-related diseases, such as diabetes and arteriosclerosis. Therefore, a daily intake of natural compounds that inhibit the production of AGEs may be beneficial in preventing these diseases. In this study, we evaluated the inhibitory effects of 14 natural crude extracts, including those of Drosera species, which possess anti-inflammatory activity, on the formation of AGEs, such as Nω-(carboxymethyl)arginine (CMA) and Nε-(carboxymethyl)lysine (CML). Crude extracts of Drosera inhibited the formation of CMA and CML by incubation on gelatin with ribose more effectively than with other extracts, so active compounds that prevent AGE formation were purified from Drosera tokaiensis, which is endemic to Japan. Several compounds were purified from D. tokaiensis extracts using HPLC and identified by NMR analysis. These compounds included ellagic acid, 3,3'-di-O-methylellagic acid 4'-glucoside, myricitrine, and quercimelin. Furthermore, all compounds showed a significantly higher inhibitory effect on CMA and CML formations than aminoguanidine. Specifically, ellagic acid and myricitrine had the highest inhibitory effects of the compounds tested. However, not all compounds showed inhibition of CMA formation in a mixture of gelatin and glyoxal (GO). These results suggest that the compounds in D. tokaiensis inhibit CMA and CML formations via the antioxidative activity of phenolic compounds, rather than GO trapping action. This study provides the first evidence that D. tokaiensis inhibits CMA and CML formations and that phenolic compounds such as ellagic acid and myricitrine play an important role as active components of D. tokaiensis extracts.

Flavonoid Compounds Contained in Epimedii Herba Inhibit Tumor Progression by Suppressing STAT3 Activation in the Tumor Microenvironment.

M2-like tumor-associated macrophages (TAMs) in the tumor tissues promote tumor progression by various mechanisms and represent possible targets of antitumor therapy. In the present study, we tested whether compounds from Epimedii Herba inhibit macrophage polarization to the M2/protumorigenic phenotype and prevent tumor progression, using human monocyte-derived macrophages (HMDMs) and an animal sarcoma model. Four Epimedii Herba-derived flavonoid compounds, namely, limonianin, epimedokoreanin B, icaritin, and desmethylicaritin, inhibited CD163 expression and interleukin (IL)-10 production, which are known M2 markers, suggesting that these compounds inhibit M2 polarization. Among these compounds, epimedokoreanin B and limonianin suppressed STAT3 activation in HMDMs. Notably, epimedokoreanin B also suppressed cell proliferation by blocking STAT3 activation in Saos-2 human sarcoma and LM8 mouse sarcoma cell lines. Furthermore, oral administration of epimedokoreanin B inhibited tumor growth in an LM8 tumor-bearing murine model. These results indicate that Epimedii Herba and Epimedii Herba-derived compounds, such as epimedokoreanin B, may be potentially new agents that can be used for the treatment and prevention of various malignant tumors. They may also be promising compounds for targeting the tumor microenvironment by inhibiting M2 polarization of the TAMs.

A natural anti-periodontitis agent, epimedokoreanin B, inhibits virulence activities of gingipains from Porphyromonas gingivalis.

Gingipains are potent virulence cysteine proteases secreted by Porphyromonas gingivalis, a major pathogen of periodontitis. We previously reported that epimedokoreanin B inhibits the activities of gingipains. In this report, we show that epimedokoreanin B inhibits the virulence of gingipains-containing P. gingivalis culture supernatants, indicating the potential use of this prenylated flavonoid as a new agent to combat against periodontal pathogens.

Natural compounds that regulate lymph node sinus macrophages: Inducing an anti-tumor effect by regulating macrophage activation.

Recent progress in anti-tumor therapy has revealed the significance of anti-tumor immune responses in tumor progression and clinical course in several kinds of malignant tumors. The draining lymph node is an important immune system component that contains a number of antigen-presenting cells, which induce rapid immune responses to foreign antigens. Current studies have shown that higher expression of CD169 on lymph node sinus macrophages is associated with the induction of anti-tumor immunity. In the present study, we searched for natural compounds that regulate the CD169-positive phenotype in macrophages to identify potential new anti-cancer agents targeting macrophage activation. Among 50 natural compounds, aculeatiside A, naringin, and onionin A significantly induced the CD169-positive phenotype in human monocyte-derived macrophages. These compounds also induced CD169 overexpression and secretion of inflammatory cytokines, including interleukin (IL)-1ß and IL-12, in murine macrophages. Subcutaneous injection of aculeatiside A and naringin enhanced mRNA expression of IL-1ß, IL12, and CD169 in regional lymph nodes in mice. These findings suggest aculeatiside A and naringin may enhance anti-tumor immune responses by inducing CD169-positive macrophages in lymph nodes.

New cyclic sulfides extracted from Allium sativum: garlicnins P, J2, and Q.

Two atypical cyclic-type sulfides, garlicnin P (1) and garlicnin J2 (2), and one thiabicyclic-type sulfide, garlicnin Q (3), were isolated from the acetone extracts of garlic, Allium sativum, bulbs cultivated in the Kumamoto city area, and their structures characterized. Their production pathways are also discussed.

New cyclic sulfides, garlicnins I2, M, N, and O, from Allium sativum.

One atypical thiolane-type sulfide, garlicnin I2 (1), two 3,4-dimethylthiolane-type sulfides, garlicnins M (2) and N (3), and one thiabicyclic-type sulfide, garlicnin O (4), were isolated from the acetone extracts of Chinese garlic bulbs, Allium sativum and their structures were characterized. Hypothetical pathways for the production of the respective sulfides were discussed.

Apoptosis induction of poly-S-nitrosated human serum albumin in resistant solid tumor under hypoxia can be restored by phosphodiesterase 5 inhibition.

Poly-S-nitrosated human serum albumin (Poly-SNO-HSA) delivered and accumulated nitric oxide (NO) in tumors and induces apoptosis. Tumor hypoxia is strongly associated with malignant progression and tumor resistance to therapy. In this study, we examined the cytotoxic effect of Poly-SNO-HSA under hypoxia on the murine colon 26 adenocarcinoma (C26) cells in vitro and in vivo. Under hypoxia, at about 4 times LD50 dose of Poly-SNO-HSA in vitro, the reactive oxygen species production was hindered but apoptotic cells were induced via cGMP pathway as the effect was suppressed by a soluble guanylate cyclase inhibitor, NS2028. The apoptosis induction effect of low dose Poly-SNO-HSA on C26 cells in vitro under hypoxia can be restored by a phosphodiesterase 5 (PDE5) inhibitor, vardenafil. In C26-bearing mice, Poly-SNO-HSA/vardenafil combination treatment significantly suppressed the tumor volume compared with Poly-SNO-HSA or vardenafil treatment alone. Furthermore, the core tumor tissues showed increased expression of caspase-3 than the non-core tissue. The expression of caspase-3 appeared to overlap with the hypoxic zone of tumor tissues. Similar results were also obtained when the experiments were repeated using Epimedium extract, a natural herbal supplement with PDE5 inhibition activity. In conclusion, Poly-SNO-HSA/PDE5 inhibitors combination therapy is a promising approach for enhancing the anticancer therapeutic effects of Poly-SNO-HSA against not only anti-cancer drug resistance but also hypoxic stress related solid tumor resistance.

Antitumor Allium Sulfides.

We examined the sulfides in onion (Allium cepa L.), Welsh onion (A. fistulosum L.), and garlic (A. sativum L.), and obtained three new thiolane-type sulfides (onionins A1-A3) from onion; two new thiabicyclic-type sulfides (welsonins A1, A2), together with onionins A1-A3, from Welsh onion; and six new acyclic-type sulfides (garlicnins L-1-L-4, E, and F), ten new thiolane-type sulfides (garlicnins A, B1-B4, C1-C3, K1, and K2), and three new atypical cyclic-type sulfides (garlicnins G, I, and J) from garlic. Acetone extracts showed the potential of these sulfides in inhibiting the polarization of M2 activated macrophages that are capable of suppressing tumor-cell proliferation. The effect of the thiolane-type sulfide of a major component, onionin A1, on tumor progression and metastasis in both osteosarcoma and ovarian cancer-bearing mouse models was then examined. Tumor proliferation was depressed, and tumor metastasis was controlled by regulating macrophage activation. These results showed that onionin A1 is an effective agent for controlling tumors in both in vitro and in vivo models, and that the antitumor effects observed in vivo are likely caused by reversing the antitumor immune system. Activation of the antitumor immune system by onionin A1 might be an effective adjuvant therapy for patients with osteosarcoma, ovarian cancer and other malignant tumors. Based on these findings, pharmacological investigations will be conducted in the future to develop natural and healthy foods and anti-cancer agents that can prevent or combat disease.

Atypical Cyclic Sulfides, Garlicnins G, I, and J, Extracted from Allium sativum.

Newly characterized, atypical sulfides, garlicnins G (1), I (2), and J (3), were isolated from the acetone extracts of garlic bulbs, Allium sativum. Their production pathways are regarded as different from those of cyclic sulfoxides, 3,4-dimethyltetrahydrothiophene-S-oxide derivatives such as onionins A1-A3, garlicnins B1-B4 and C1-C3.