Phytochemicals of Alpinia zerumbet: A Review.

Alpinia zerumbet (Pers.) B.L.Burtt & R.M.Sm is a perennial plant of the Zingiberaceae family widely distributed in the subtropical and tropical areas of South America, Oceania, and Asia. Multiple plant parts of A. zerumbet have been traditionally used as medicinal sources, each with different clinical uses. These variations may arise from differences among the chemical components and/or accumulations of the active compounds in each part. Therefore, this review summarizes previous studies on the phytochemicals in A. zerumbet and reveals the similarities and differences among the chemical constituents of its multiple medicinal parts, including the leaves, rhizomes, fruits, seeds, and flowers. The results contribute to the scientific validation of the traditional understanding that A. zerumbet possesses different medicinal properties in each plant part. In addition, this review provides directions for further studies on the phytochemicals of this plant.

Sesquiterpenes and α-pyrones from an endophytic fungus Xylaria curta YSJ-5.

Chemical investigation of the culture extract of an endophyte Xylaria curta YSJ-5 from Alpinia zerumbet (Pers.) Burtt. et Smith resulted in the isolation of eight previously undescribed compounds including five eremophilane sesquiterpenes xylarcurenes A-E, one norsesquiterpene xylarcurene F, and two α-pyrone derivatives xylarpyrones A-B together with eight known related derivatives. Their chemical structures were extensively established based on the 1D- and 2D-NMR spectroscopic analysis, modified Mosher's method, electronic circular dichroism calculations, single-crystal X-ray diffraction experiments, and the comparison with previous literature data. All these compounds were tested for in vitro cytotoxic, anti-inflammatory, α-glucosidase inhibitory, and antibacterial activities. As a result, 6-pentyl-4-methoxy-pyran-2-one was disclosed to display significant antibacterial activity against Staphylococcus aureus and methicillin-resistant S. aureus with minimal inhibitory concentration value of 6.3 µg/mL.

Anti-hypertensive and composition as well as pharmacokinetics and tissues distribution of active ingredients from Alpinia zerumbet.

Alpinia zerumbet is a food flavor additive and a traditional medicine herb around the world. Several studies have reported that A. zerumbet has excellent effects on a variety of cardiovascular diseases, but its potential hypertensive applications, and pharmacokinetic features of main active substances have not been fully investigated. The mechanism of anti-hypertension with ethyl acetate extracts of A. zerumbet fruits (AZEAE) was evaluated by L-NNA-induced hypertensive rats and L-NAME-injured human umbilical vein endothelial cells (HUVECs). Blood pressure, echocardiographic cardiac index and H&E staining were used to preliminary evaluate the antihypertensive effect of AZEAE, the levels of TNF-α, IL-6, and IL-1ß were evaluated by ELISA, and the proteins expression of IL-1ß, IL-18, AGTR1, VCAM, iNOS, EDN1 and eNOS were also evaluated. In addition, isolation, identification, and activity screening of bioactive compounds were carried ou. Next, pharmacokinetics and tissues distribution of dihydro-5,6-dehydrokavain (DDK) in vivo were measured, and preliminary absorption mechanism was conducted with Caco-2 cell monolayers. AZEAE remarkably enhanced the state of hypertensive rats. Twelve compounds were isolated and identified, and five compounds were isolated from this plant for the first time. The isolated compounds also exhibited good resistance against injury of HUVECs. Moreover, pharmacokinetics and Caco-2 cell monolayers demonstrated AZEAE had better absorption capacity than DDK, and DDK exhibited differences in tissues distribution and gender difference. This study was the first to assess the potential hypertensive applications of A. zerumbet in vivo and vitro, and the first direct and concise study of the in vivo behavior of DDK and AZEAE.

Preparation and in vivo Distribution of Essential Oil from Alpinia zerumbet Fructus Encapsulated Nanoemulsions / 中国实验方剂学杂志

ObjectiveTo prepare oral nanoemulsions encapsulating essential oil from Alpinia zerumbet fructus（EOFAZ） and to investigate its pro-absorption effect in vitro and distribution in vivo. MethodThe proteoglycan conjugate polysaccharides of vinegar-processed Bupleuri Radix-bovine serum albumin（VBCP-BSA） was prepared by Maillard reaction of VBCP and BSA. Taking VBCP-BSA as emulsifier， vitamin B12（VB12） as absorption enhancer， and medium chain triglycerides mixed with EOFAZ as oil phase， the nanoemulsions loaded with EOFAZ was prepared by high energy emulsification method. The particle size， particle size distribution， surface Zeta potential， EOFAZ content and appearance and morphology of the nanoemulsions were characterized， and fluorescein tracer method was used to investigate the absorption effect of fluorescein-labeled EOFAZ nanoemulsions in vitro and their distribution in vivo. ResultVBCP-BSA was formed by Maillard reaction for 48 h with high grafting rate. Using VBCP-BSA as emulsifier， the homogeneous pink nanoemulsions was prepared and denoted as EOFAZ@VBCP-BSA/VB12. The particle size of the nanoemulsions was less than 100 nm and the particle size distribution was uniform. The surface of the nanoemulsions was a weak negative charge， and the shape was spherical. The encapsulation rate of the nanoemulsions for EOFAZ was greater than 80%， which had a good absorption effect in vitro and could enhance liver accumulation after oral administration. ConclusionThe designed proteoglycan nanoemulsions can effectively load EOFAZ， promote oral absorption and enhance liver distribution， which can provide experimental basis for the development of oral EOFAZ liver protection preparations.

Essential oil from Fructus Alpinia zerumbet ameliorates atherosclerosis by activating PPARγ-LXRα-ABCA1/G1 signaling pathway.

BACKGROUND: Atherosclerosis (AS) is a progressive chronic disease. Currently, cardiovascular diseases (CVDs) caused by AS is responsible for the global increased mortality. Yanshanjiang as miao herb in Guizhou of China is the dried and ripe fruit of Fructus Alpinia zerumbet. Accumulated evidences have confirmed that Yanshanjiang could ameliorate CVDs, including AS. Nevertheless, its effect and mechanism on AS are still largely unknown. PURPOSE: To investigate the role of essential oil from Fructus Alpinia zerumbet (EOFAZ) on AS, and the potential mechanism. METHODS: A high-fat diet (HFD) ApoE-/- mice model of AS and a oxLDL-induced model of macrophage-derived foam cells (MFCs) were reproduced to investigate the pharmacological properties of EOFAZ on AS in vivo and foam cell formation in vitro, respectively. The underlying mechanisms of EOFAZ were investigated using Network pharmacology and molecular docking. EOFAZ effect on PPARγ protein stability was measured using a cellular thermal shift assay (CETSA). Pharmacological agonists and inhibitors and gene interventions were employed for clarifying EOFAZ's potential mechanism. RESULTS: EOFAZ attenuated AS progression in HFD ApoE-/- mice. This attenuation was manifested by the reduced aortic intima plaque development, increased collagen content in aortic plaques, notable improvement in lipid profiles, and decreased levels of inflammatory factors. Moreover, EOFAZ inhibited the formation of MFCs by enhancing cholesterol efflux through activiting the PPARγ-LXRα-ABCA1/G1 pathway. Interestingly, the pharmacological knockdown of PPARγ impaired the beneficial effects of EOFAZ on MFCs. Additionally, our results indicated that EOFAZ reduced the ubiquitination degradation of PPARγ, and the chemical composition of EOFAZ directly bound to the PPARγ protein, thereby increasing its stability. Finally, PPARγ knockdown mitigated the protective effects of EOFAZ on AS in HFD ApoE-/- mice. CONCLUSION: These findings represent the first confirmation of EOFAZ's in vivo anti-atherosclerotic effects in ApoE-/- mice. Mechanistically, its chemical constituents can directly bind to PPARγ protein, enhancing its stability, while reducing PPARγ ubiquitination degradation, thereby inhibiting foam cell formation via activation of the PPARγ-LXRα-ABCA1/G1 pathway. Simultaneously, EOFAZ could ameliorates blood lipid metabolism and inflammatory microenvironment, thus synergistically exerting its anti-atherosclerotic effects.

Anti-Inflammatory Terpenoids from the Rhizomes of Shell Ginger.

Shell ginger (Alpinia zerumbet) is a perennial ornamental plant of ginger native to East Asia, which can be used as a flavoring agent in food or beverage, as well as a traditional Chinese medicine. In this study, a total of 37 terpenoids, including 7 new compounds, zerumin D1 to zerumin D7 (2, 3, 28-30, 36, and 37), and 5 new naturally occurring compounds, zerumin D10 to zerumin D14 (9, 12, 15, 20, and 24), were isolated and identified from the rhizomes of shell ginger. Compound 3 was an unprecedented variant labdane diterpenoid featuring a unique 6/7/6/3 tetracyclic cyclic ether system in its side chain. The anti-inflammatory activities of the isolated terpenoids were assessed in RAW 264.7 macrophages stimulated by lipopolysaccharide (LPS). Compound 4 significantly inhibited the production of nitric oxide with an IC50 value of 5.4 µM. Further investigation revealed that compounds 2 and 3 may inhibit the nuclear translocation of NF-κB, thus suppressing the expression of IL-6, IL-1ß, iNOS, and COX-2 to exert the anti-inflammatory effects.

Chemical Composition and Potential Antimicrobial and Anti-Inflammatory Activities of Essential Oil from Fruits of Alpinia zerumbet (Pers.) B.L.Burtt & R.M.Sm.

Alpinia zerumbet (Pers.) B.L.Burtt & R.M.Sm. was extensively used in traditional medicine for its several properties, but continuous investigation is needed to discover the properties of its essential oils (EOs). This work evaluated the properties of an EO obtained by steam distillation (named ESD) as well as extracts obtained by petroleum ether (named EP) both from Alpinia zerumbet fruits. Gas chromatography-mass spectrometry (GC-MS) was chosen to identify the composition, and eleven compounds were identified as the main components of the EO and EP of Alpinia zerumbet fruits. The antimicrobial properties were investigated by minimum inhibitory concentration (MIC) and the inhibition area. The results identified the differences in antimicrobial activities attributed to different extraction methods. Enzyme-linked immunosorbent assay (ELISA) and Western Blot (WB) assay were conducted to assess the anti-inflammatory effects of ESD. In conclusion, our study suggested that EO from Alpinia zerumbet fruits might be a prospective candidate for antimicrobial and anti-inflammatory therapy.

Fabrication of a protein-dextran conjugates formed oral nanoemulsion and its application to deliver the essential oil from Alpinia zerumbet Fructus.

The injury of vascular endothelial cells caused by high glucose (HG) is one of the driving factors of vascular complications of diabetes. Oral administration is the most common route of administration for the treatment of diabetes and its vascular complications. Essential oil extracts from Chinese medicine possess potential therapeutic effects on vascular endothelial injury. However, low solubility and volatility of essential oils generally result in poor oral absorption. Development of nanocarriers for essential oils is a promising strategy to overcome the physiological barriers of oral absorption. In this study, a nanoemulsion composed of bovine serum albumin (BSA)-dextran sulfate (DS) conjugate and sodium deoxycholate (SD) was constructed. The nanoemulsions were verified with promoted oral absorption and prolonged circulation time. After the primary evaluation of the nanoemulsion, essential oil from Alpinia zerumbet Fructus (EOFAZ)-loaded nanoemulsion (denoted as EOFAZ@BD5/S) was prepared and characterized. Compared to the free EOFAZ, EOFAZ@BD5/S increased the protective effects on HG-induced HUVEC injury in vitro and ameliorative effects on the vascular endothelium disorder and tunica media fibroelastosis in a T2DM mouse model. Collectively, this study provides a nanoemulsion for the oral delivery of essential oils, which holds strong promise in the treatment of diabetes-induced vascular endothelial injury.

Vasorelaxant effect of Alpinia zerumbet's essential oil on rat resistance artery involves blocking of calcium mobilization.

Alpinia zerumbet is a plant from the Zingiberaceae family, popularly used for hypertension treatment. Several studies have demonstrated Alpinia zerumbet vasodilator effect on conductance vessels but not on resistance vessels. Thereby, the aim of this study was to verify the vasodilator effect of the essential oil of Alpinia zerumbet (EOAz) on isolated rat resistance arteries and characterize its mechanism of action. Therefore, the effect of EOAz (3 to 3000 µg/mL) was verified in second-order branches of the mesenteric artery (SOBMA) pre-contracted by KCl and U46619. To study the mechanism of action, the influence of several inhibitors (TEA, 4-AP, Glibenclamide, Atropine, L-NAME, ODQ and indomethacin) on the vasodilator effect of EOAz was evaluated. Some protocols were also performed aiming to study the effect of EOAz on Ca2+ influx and release from intracellular storage. Furthermore, the binding energy of the main constituents with calcium channels were evaluated by molecular docking. Results showed an endothelium-independent vasorelaxant effect of EOAz on SOBMA, and only ODQ and L-NAME produced significant alteration on its pEC50. Regarding the calcium assays, contraction reduction caused by incubation with EOAz was observed in all three protocols. Hence, our results suggest that EOAz has a vasodilator effect mediated by inhibition of Ca2+ influx and release from intracellular storage, as well as an activation of the NOS/sGC pathway.

Mode of Antifungal Action of Daito-Gettou (Alpinia zerumbet var. exelsa) Essential Oil against Aspergillus brasiliensis.

Plant-derived essential oils (EOs) are used in medicines, disinfectants, and aromatherapy products. Information on the antifungal activity of EO of Alpinia zerumbet var. exelsa (known as Daito-gettou) found in Kitadaito Island, Okinawa, is limited. Therefore, we aimed to evaluate the antifungal activity of EOs obtained via steam distillation of leaves of Daito-gettou, which is a hybrid of A. zerumbet and A. uraiensis. Daito-gettou EO showed antifungal activity (minimum inhibitory concentration = 0.4%) against Aspergillus brasiliensis NBRC 9455, which was comparable to that of A. zerumbet found in the Okinawa main island. Gas chromatography/mass spectrometry revealed that the main components of Daito-gettou EOs are γ-terpinene, terpinen-4-ol, 1,8-cineole, 3-carene, and p-cymene. Terpinen-4-ol content (MIC = 0.075%) was 17.24%, suggesting that the antifungal activity of Daito-gettou EO was mainly attributable to this component. Daito-gettou EO and terpinen-4-ol inhibited mycelial growth. Moreover, calorimetric observations of fungal growth in the presence of Daito-gettou EO showed a characteristic pattern with no change in the initial growth rate and only a delay in growth. As this pattern is similar to that of amphotericin B, it implies that the action mode of Daito-gettou EO and terpinen-4-ol may be fungicidal. Further studies on the molecular mechanisms of action are needed for validation.

Two new monoterpene esters from the pericarps of Alpinia zerumbet.

Two new monoterpene esters (1 and 2) and four known compounds (3-6) were isolated from the pericarps of Alpinia zerumbet. Their structures were elucidated by extensive spectroscopic analyses and their anti-inflammatory activity was evaluated by monitoring their inhibitory effects on the interleukin-1ß-induced production of nitric oxide in primary cultured rat hepatocytes. The new compound 1 and cardamonin 3 showed inhibitory activities with IC50 values of 17.6 ± 1.1 and 10.2 ± 1.3 µM, respectively, which are comparable to that of the positive control NG-methyl-L-arginine acetate salt.

Improvement effect and mechanism of total flavonoids from Alpinia zerumbet on gastric mucosa injury induced by absolute ethanol / 中国药房

OBJECTIVE To explore the improvement effect and potential mechanism of total flavonoids from Alpinia zerumbet on gastric mucosa injury induced by absolute ethanol through microRNA-146a-5p （miR-146a-5p）. METHODS Using human gastric mucosa GES-1 cells as objects， the acute gastric ulcer model was established by absolute ethanol； based on the investigation of the effects of different concentrations of total flavonoids from A. zerumbet on cell activity and the selection of action concentration， the relative expression level of miR-146a-5p in GES-1 cells was detected， the protein expressions of tumor necrosis factor （TNF） receptor-associated factor 6（TRAF6）， nuclear factor-κB p65 （NF-κB p65） and TNF-α were detected， and the levels of interleukin- 1β （IL-1β）， IL-6 and prostaglandin E2 （PGE2） in cell supernatant were determined. The targeting relationship between miR-146a- 5p and TRAF6 was verified； the effects of overexpressed miR-146a-5p and TRAF6 knockdown on the levels of IL-1β， IL-6 and PEG2 in supernatant of model cells as well as the effects of miR-146a-5p knockdown on anti-gastric ulcer effect of total flavonoids from A. zerumbet were observed. RESULTS Compared with the blank group， the relative expression of miR-146a-5p in cells and the level of PGE2 in cell supernatant were decreased significantly in the model group （P＜0.01）， while the protein expressions of TRAF6， NF-κB p65 and TNF-α in cells and the levels of IL-1β and IL-6 in cell supernatant were increased significantly （P＜ 0.01）. Compared with the model group， the relative expression of miR-146a-5p in cells and the level of PGE2 in cell supernatant were increased significantly in model+A. zerumbet total flavonoids （60 mg/L） group （P＜0.01）， while the protein expressions of TRAF6， NF-κB p65 and TNF-α in cells and 82260767） the levels of IL-1β and IL-6 in cell supernatant were decreased significantly （P＜0.05 or P＜0.01）. There was a targeted relationship and a negative correlation between miR-146a-5p E-mail：3113836821@qq.com and TRAF6. After overexpression of miR-146a-5p or TRAF6 knockdown， the levels of IL-1β and IL-6 were decreased significantly in cell supernatant， while the level of PGE2 was increased significantly （P＜0.05）. After miR-146a-5p knockdown， the levels of IL-1β and IL-6 in cell supernatant and the protein expression of TRAF6 in cells administered with total flavonoids of A. zerumbet were increased significantly， while the level of PGE2 was decreased significantly （P＜0.05）. CONCLUSIONS Total flavonoids of A. zerumbet can improve the gastric mucosa injury induced by absolute ethanol. The mechanism may be related to up-regulating the expression of miR-146a-5p， inhibiting the expression of TRAF6， and further inhibiting the secretion of related inflammatory factors.

Determination of Community Structure and Diversity of Seed-Vectored Endophytic Fungi in Alpinia zerumbet.

Endophytic fungi act as seed endosymbiont, thereby playing a very crucial role in the growth and development of seeds. Seed-vectored endophytic fungi establish an everlasting association with seeds and travel from generation to generation. To explore the composition and diversity of endophytic fungi in Alpinia zerumbet seeds, high-throughput Illumina MiSeq sequencing was employed for the following stages: fruit formation period (YSJ1), young fruit period (YSJ2), early mature period (YSJ3), middle mature period (YSJ4), and late mature period (YSJ5). A total of 906,694 sequence reads and 745 operational taxonomic units (OTUs) were obtained and further classified into 8 phyla, 30 classes, 73 orders, 163 families, 302 genera, and 449 species. The highest endophytic fungal diversity was observed at YSJ5. The genera with the highest abundance were Cladosporium, Kodamaea, Hannaella, Mycothermus, Gibberella, Sarocladium, and Neopestalotiopsis. Functional Guild (FUNGuild) analysis revealed that endophytic fungi were undefined saprotroph, plant pathogens, animal pathogen-endophyte-lichen parasite-plant pathogen-wood saprotroph, and soil saprotrophs. Alternaria, Fusarium, Cladosporium, and Sarocladium, which are potential probiotics and can be used as biocontrol agents, were also abundant. This study is part of the Sustainable Development Goals of United Nations Organization (UNO) to "Establish Good Health and Well-Being."

Molecular investigation of proanthocyanidin from Alpinia zerumbet against the influenza A virus.

Proanthocyanidins (PACs) have various bioactivities, such as being anti-bacterial, anti-cancer, and anti-oxidant. Consequently, they have been vigorously studied for the development of new natural bioactive compounds. Recently, PAC was isolated from leaves and pseudostems of the medicinal plant Alpinia zerumbet (Pers.) B.L. Burtt and R.M. Smith, and it had shown in vitro antiviral activity against influenza A H1N1 viruses (IAVs). The 50% endpoint dilution method indicated that 0.1 mg/mL A. zerumbet-derived PAC (AzPAC) reduced the titer of IAVs by >3 logs. The antiviral activity of AzPAC means that it can interact directly with viral particles since the antiviral activity test was done by coincubation of PAC with and IAVs before viral infection. However, few studies have investigated the preventive mechanism utilized by AzPAC on influenza virus replication. In this study, the composition of AzPAC and the affinity between AzPAC and IAVs was investigated in detail. We found that AzPAC was composed of an epicatechin, which was linked by inter-flavan bonds between the C4 and C8 positions (B2-type) and the C4 and C6 positions (B5-type) in the terminal units. A quenching assay indicated that AzPAC interacted with IAV membrane proteins, hemagglutinin and neuraminidase. Additionally, circular dichroism analysis indicated that AzPAC affected the change in the secondary structure rate of the viral membrane proteins. AzPAC was able to impair the infective process of IAVs via direct interaction with their viral membrane proteins. These results indicate that A. zerumbet is a bioresource for the development of preventive drugs against IAV infection.

Kavalactones isolated from Alpinia zerumbet (Pers.) Burtt. et Smith with protective effects against human umbilical vein endothelial cell damage induced by high glucose.

A new kavalactone, 4'-hydroxyl dihydro-5, 6-dehydrokavain (1) was isolated from the petroleum ether partition of leaves of Alpinia zerumbet (Pers.) Burtt. et Smith, together with four known kavalactone dimers, rel-1,trans-3-bis-(4-methoxy-2-oxopyran-6-yl)-cis-2,trans-4-diphenyl cyclobutene (2), aniba dimer A (3), aniba dimer C (4), 6,6'-(3,4-diphenylcyclobutane-1,2-diyl)bis(4-methoxy-2H-pyran-2-one (5). The structure of compound 1 was characterized by its MS, 1D-NMR, and 2D-NMR data, and the structures of the known compounds were determined by comparison of their spectroscopic data with those reported by the literatures. The obtained compounds were evaluated for their protective activities on human umbilical vein endothelial cells (HUVECs) damaged by high glucose (35 mM, cell viability at 70.10%). Compounds 3 and 5 could increase the cell viability at the concentration of 12.5 µΜ (83.12%) and 25 µΜ (75.02%), whereas at the concentration of 12.5 µΜ, compounds 1, 2, and 4 didn't reverse cell damage (cell viability at 38.58%, 54.80% and 58.16%).

Involvement of anti-inflammatory, antioxidant, and BDNF up-regulating properties in the antipsychotic-like effect of the essential oil of Alpinia zerumbet in mice: a comparative study with olanzapine.

The current drug therapy for schizophrenia effectively treats acute psychosis and its recurrence; however, this mental disorder's cognitive and negative symptoms are still poorly controlled. Antipsychotics present important side effects, such as weight gain and extrapyramidal effects. The essential oil of Alpinia zerumbet (EOAZ) leaves presents potential antipsychotic properties that need further preclinical investigation. Here, we determined EAOZ effects in preventing and reversing schizophrenia-like symptoms (positive, negative, and cognitive) induced by ketamine (KET) repeated administration in mice and putative neurobiological mechanisms related to this effect. We conducted the behavioral evaluations of prepulse inhibition of the startle reflex (PPI), social interaction, and working memory (Y-maze task), and verified antioxidant (GSH, nitrite levels), anti-inflammatory [interleukin (IL)-6], and neurotrophic [brain-derived neurotrophic factor (BDNF)] effects of this oil in hippocampal tissue. The atypical antipsychotic olanzapine (OLZ) was used as standard drug therapy. EOAZ, similarly to OLZ, prevented and reversed most KET-induced schizophrenia-like behavioral alterations, i.e., sensorimotor gating deficits and social impairment. EOAZ had a modest effect on the prevention of KET-associated working memory deficit. Compared to OLZ, EOAZ showed a more favorable side effects profile, inducing less cataleptic and weight gain changes. EOAZ efficiently protected the hippocampus against KET-induced oxidative imbalance, IL-6 increments, and BDNF impairment. In conclusion, our data add more mechanistic evidence for the anti-schizophrenia effects of EOAZ, based on its antioxidant, anti-inflammatory, and BDNF up-regulating actions. The absence of significant side effects observed in current antipsychotic drug therapy seems to be an essential benefit of the oil.

Neolignans and Diarylheptanoids with Anti-Inflammatory Activity from the Rhizomes of Alpinia zerumbet.

The dried leaves and rhizomes of Alpinia zerumbet have been traditionally used as food and medicine. Anti-inflammatory activity-guided phytochemical investigation into the rhizomes of A. zerumbet led to the isolation of 17 compounds including 10 neolignans (1-10, 1a, 1b, 2a, 2b, 3a, 3b, 4, and 5 are new compounds) and seven diarylheptanoids (11-17) in which 1-3 were three pairs of enantiomers. 4 was only one enantiomer and 5 was a racemic mixture. Compounds 1a, 1b, 2a, and 2b incorporated an 8',9'-dinorneolignan skeleton, which was rare in the lignan family. The planar structures of these compounds were elucidated by extensive analyses of spectroscopic data. The relative and absolute configurations were determined by the time-dependent density functional theory (TDDFT)-based electronic circular dichroism (ECD) calculation method. The 95% ethanol extract and ethyl acetate extract of A. zerumbet were found to show anti-inflammatory activity against croton oil-induced ear edema in mice with inhibition rates of 20.0 and 47.6% at a dose of 80 mg/kg, respectively. Bioassays showed that compounds 1a, 1b, 2a, 2b, and 12 moderately inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW264.7 cells with IC50 values of 3.62, 7.63, 6.51, 5.60, and 8.33 µM, respectively.

Chemical constituents, larvicidal activity and molluscicidal from fresh leaves of Alpinia zerumbet (Pers.) and Cymbopogon citratus (DC.) Stapf / Constituyentes químicos, actividad larvicida y molusquicida de hojas frescas de Alpinia zerumbet (Pers.) y Cymbopogon citratus (DC.) Stapf / Constituintes químicos, atividade larvicida e moluscicida de folhas frescas de Alpinia zerumbet (Pers.) e Cymbopogon citratus (DC.) Stapf

SUMMARY Introduction: This study evaluated the chemical characterization, larvicidal activity and molluscicidal activity in front of the snail transmitting schistosomes (Biomphalaria glabrata) of the essential oils of Alpinia zerumbet and Cymbopogon citratus (DC.) Stapf. The essential oils (EOs) were extracted by hydrodistillation, with chemical characterization through Gas Chromatography coupled to mass spectrometry (GC-MS). The physical-chemical parameters were determined according to the Brazilian Pharmacopoeia. The toxicity test followed the bioassay with Artemia salina Leach, the EOs approved in this assay followed to evaluate their biological properties. Methodology: For molluscicidal activity, the methodology recommended by the WHO was performed, and the LC50 of the EOs was performed for their action in the face of the snail obtained by the Reed&Muench method. Both EOs showed low toxicity, and thus were evaluated for the biological properties larvicidal and molluscicidal. Alpinia zerumbet EO showed molluscicidal activity with LC50 of40.63 mg-L-1 and Cymbopogon citratus EO 33.94 mg-L-1. Results: Both EOs showed larvicidal and molluscicidal potentials against the organisms tested, showing satisfactory results for their action. The results indicate that the evaluated EOs are composed of substances that promote and encourage their application due to their potential for molluscicidal and larvicidal biological activity.

RESUMEN Introducción: Este estudio evaluó la caracterización química, la actividad larvicida y la actividad molusquicida frente al caracol que transmite esquistosomas (Biomphalaria glabrata) de los aceites esenciales de Alpinia zerumbet y Cymbopogon citratus (DC.) Stapf. Los aceites esenciales (AE) fueron extraídos por hidrodestilación, con caracterización química a través de cromatografía de gases acoplada a espectrometría de masas (GC-MS). Los parámetros físico-químicos se determinaron de acuerdo con la Farmacopea Brasileña. La prueba de toxicidad siguió al bioensayo con Artemia salina Leach, los AE probados en este ensayo se evaluaron a continuación en sus propiedades biológicas. Metodología: Para la actividad molusquicida se empleó la metodología recomendada por la OMS, y la LC50 de las AE se realizó para su acción frente al caracol obtenido por el método Reed&Muench. Ambos AE mostraron baja toxicidad, y por lo tanto fueron evaluados para las propiedades biológicas larvicidas y molusquicidas. Alpinia zerumbet AE mostró actividad molusquicida con LC50 de 40,63 mg-L'1 y Cymbopogon citratus EO 33,94 mg-L-1. Resultados: Ambos AE mostraron potenciales larvicidas y molusquicidas contra los organismos probados, mostrando resultados satisfactorios para su acción. Los resultados indican que los AE evaluados están compuestos de sustancias que promueven y fomentan su aplicación debido a su potencial para la actividad biológica molusquicida y larvicida.

RESUMO Introdução: Este estudo avaliou a caracterização química, atividade larvicida e ativi-dade moluscicida contra o caramujo transmissor de esquistossomos (Biomphalaria glabrata) dos óleos essenciais de Alpinia zerumbet e Cymbopogon citratus (DC.) Stapf. Os óleos essenciais (AE) foram extraídos por hidrodestilação, com caracterização química por cromatografia gasosa acoplada a espectrometria de massas (CG-EM). Os parâmetros físico-químicos foram determinados de acordo com a Farmacopéia Brasileira. O teste de toxicidade seguiu o bioensaio com Artemia salina Leach, os EA testados neste teste foram então avaliados quanto às suas propriedades biológicas. Metodologia: Para a atividade moluscicida, foi utilizada a metodologia recomendada pela OMS, e o LC50 do EA foi realizado para sua ação contra o caramujo obtido pelo método de Reed & Muench. Ambos os AE apresentaram baixa toxicidade e, portanto, foram avaliados quanto às propriedades biológicas larvicidas e moluscicidas. Alpinia zerumbet AE apresentou atividade moluscicida com CL50 de 40,63 mg-L-1 e Cymbopogon citratus EO 33,94 mg-L-1. Resultados: Ambos os AE apresentaram potencial larvicida e moluscicida contra os organismos testados, apresentando resultados satisfatórios para sua ação. Os resultados indicam que os AE avaliados são compostos por substâncias que promovem e estimulam sua aplicação devido ao seu potencial de atividade biológica moluscicida e larvicida.

Inactivation of plant and animal viruses by proanthocyanidins from Alpinia zerumbet extract.

Alpinia zerumbet (Pers.) B.L. Burtt and R.M. Smith belongs to the Alpinia genus in the Zingiberaceae family. In East Asia, Alpinia zerumbet has been widely used as food and traditional medicine. Previously, we identified proanthocyanidins (PACs), an anti-plant-virus molecule in A. zerumbet, using Nicotiana benthamiana and tomato mosaic virus (ToMV). Here, we found that PACs from A. zerumbet, apple, and green tea effectively inhibited ToMV infection. Additionally, the PACs from A. zerumbet exhibited greater antiviral activity than those from apple and green tea. The PACs from A. zerumbet also effectively inactivated influenza A virus and porcine epidemic diarrhea virus (PEDV), which acts as a surrogate for human coronaviruses, in a dose-dependent manner. The results from the cytopathic effect assays indicated that 0.1 mg/ml PACs from A. zerumbet decreased the titer of influenza A virus and PEDV by >3 log. These findings suggested that the direct treatment of viruses with PACs from A. zerumbet before inoculation reduced viral activity; thus, PACs might inhibit infections by an influenza virus, coronaviruses, and plant viruses.

Identification of an anti-plant-virus molecule in Alpinia zerumbet.

In plants, viral diseases are second only to fungal diseases in terms of occurrence, and cause substantial damage to agricultural crops. The aqueous extracts of shell ginger, Alpinia zerumbet exhibit inhibitory effects against virus infections in belonging to the Solanaceae family. In this study, we isolated an anti-plant-virus molecule from the extracts using a conventional method involving a combination of reversed phase column chromatography, dialysis, and lyophilization. The anti-plant-virus molecule was identified as proanthocyanidin, which mostly consisted of epicatechin and exhibited more than 40 degrees of polymerization.