Irciniaplysins A-D: New Psammaplysin Derivatives from Philippine Marine Sponge Ircinia sp.

Four new psammaplysin derivatives (1-4) with fatty acyl substituents, designated irciniaplysins A-D, and three known psammaplysins (5-7) were isolated from a marine sponge Ircinia sp. Their structures were elucidated using extensive spectroscopic analyses. The positions of the double bonds and the branch points of the fatty acyl side chains were determined by GC-MS analysis of their fatty acid methyl ester (FAME) derivatives. Irciniaplysins A (1) and B (2) contained an unusual long-chain fatty acyl substituent with a 5,9-diene unit. The isolated compounds were evaluated for their cytotoxic activity against the human colorectal carcinoma (HCT 116) cells, however, none of these compounds showed significant activity.

Role of trisaccharides in larval secretion of Lycaeides argyrognomon butterfly on ant attendance.

Several myrmecophilous insects participate in symbiotic relationships with ants that receive sugar-rich food rewards. For instance, certain aphid species secrete honeydew containing high concentration of melezitose, which acts as a potent feeding-stimulant and attractant for ants. Lycaenid butterfly larvae possess dorsal nectary glands that secrete sugar-rich droplets for tending ants. However, the roles of sugar components in ant foraging and larva-tending activities are unknown. Lycaeides (Plebejus) argyrognomon are larvae that are frequently and facultatively attended by various ant species, including Formica japonica, on the host plant Indigofera pseudotinctoria. The larval secretions of this insect contained small amounts of trisaccharides, melezitose and maltotriose, which were not detected in the host plant's flower nectar, and larval secretions of two sympatric and myrmecophilous lycaenids, Zizeeria maha and Everes argiades. Melezitose and maltotriose, along with sucrose, were preferred by the worker ants. Of the four sugar mixture samples that mimicked I. pseudotinctoria floral nectar and the larval secretions of three lycaenids, respectively, the L. argyrognomon mimic was the most preferred by F. japonica ants. Moreover, the removal of trisaccharides from this mimic significantly reduced its stimulatory activity to ant feedings. These results indicated that the sugar composition of L. argyrognomon larval secretions is suited to the feeding preference of F. japonica ants, and that the trisaccharide components play a key role in increasing their preference. However, only half of the ants responded to the L. argyrognomon mimic even at the concentration corresponding to the maximum total sugar concentration in the collected larval secretions. The fact that the secretions of all L. argyrognomon larvae did not have sufficient sugar levels to stimulate ant feedings suggests that the production of sugar-rich secretions and trisaccharide components is metabolically costly for the larvae and that components other than sugars may be involved in ant attendance.

Experimental verification of fiber coupling characteristics for FSO downlinks from the International Space Station.

Free-space optical (FSO) systems are compulsory to realize high capacity and interference-free communication links from low-Earth orbit (LEO) satellite constellations as well as spacecraft and space stations to the Earth. To be integrated with high-capacity ground networks, the collected portion of the incident beam should be coupled into an optical fiber. To accurately evaluate the signal-to-noise ratio (SNR) and bit-error rate (BER) performance metrics, the probability density function (PDF) of fiber coupling efficiency (CE) must be determined. Previous studies have experimentally verified the CE PDF for a single-mode fiber, however, there is no such investigation for the CE PDF of a multi-mode fiber (MMF) in a LEO-to-ground FSO downlink. In this paper, for the first time, the CE PDF for a 200-µm MMF is experimentally investigated using data from an FSO downlink from the Small Optical Link for International Space Station (SOLISS) terminal to a 40-cm sub-aperture optical ground station (OGS) supported by a fine-tracking system. An average CE of 5.45 dB was also achieved given that the alignment between SOLISS and OGS was not optimal. In addition, using the angle-of-arrival (AoA) and received power data, the statistical characteristics such as channel coherence time, power spectral density, spectrogram, and PDFs of AoA, beam misalignments, and atmospheric turbulence-induced fluctuations are revealed and compared with the state-of-the-art theoretical background.

Two new sarasinosides from marine sponge Petrosia nigricans.

Two new sarasinosides designated as 5,8-epoxysarasinoside (1) and 8,9-epoxysarasinoside (2) and four known sarasinosides were isolated from marine sponge Petrosia nigricans, collected off the coast of Lipata, Surigao City, Philippines (9°49' North, 125°27' East). The structures were determined through extensive 2D NMR spectroscopy and HRMS. Both compounds exhibited low cytotoxicity against the HCT116 (colon) and A549 (lung) cancer cell lines.

Polyhydroxy Acids as Fabaceous Plant Components Induce Oviposition of the Common Grass Yellow Butterfly, Eurema Mandarina.

The common grass yellow butterfly, Eurema mandarina is a Fabaceae-feeding species, the females of which readily oviposit on Albizia julibrissin and Lespedeza cuneata in mainland Japan. We previously demonstrated that the methanolic leaf extracts of these plants, and their highly polar aqueous fractions strongly elicit female oviposition. Furthermore, the three subfractions obtained by ion-exchange chromatographic separation of the aqueous fraction have been found to be less effective alone, but synergistically stimulate female oviposition when combined. This indicates that female butterflies respond to multiple compounds with different acidity. We have previously identified d-pinitol from the neutral/amphoteric subfractions and glycine betaine from the basic subfractions as oviposition stimulants of E. mandarina. The present study aimed to identify active compounds in the remaining acidic subfractions of A. julibrissin and L. cuneata leaf extracts. GC-MS analyses of trimethylsilyl-derivatized samples revealed the presence of six compounds in the acidic subfractions. In bioassays using these authentic chemicals, erythronic acid (EA) and threonic acid (TA) were moderately active in eliciting oviposition responses in E. mandarina, with their d-isomers showing slightly higher activity than their l-isomers. Female responsiveness differed between d-EA and l-TA, the major isomers of these compounds in plants, with the response to d-EA reaching a plateau at concentrations above 0.005% and that to l-TA peaking at a concentration of 0.01%. The natural concentrations of d-EA and l-TA in fresh A. julibrissin and L. cuneata leaves were sufficient to stimulate oviposition. Furthermore, mixing 0.001% d-EA or 0.001% l-TA, to which females are mostly unresponsive, with 0.1% d-pinitol resulted in a synergistic enhancement of the oviposition response. These findings demonstrate that E. mandarina females utilize both polyhydroxy acids, EA and TA, as chemical cues for oviposition.

Isolation of Fluorescent Benzoxazines with Neuroprotective Activity from the Olive Weevil Pimelocerus perforatus.

The weevil Pimelocerus perforatus poses a serious pest problem for olive cultivation in Japan. Two new racemic fluorescent benzoxazines, designated as pimeforazine A ((±)-1) and pimeforazine B ((±)-2), were successfully isolated from P. perforatus. Their structures, including the absolute configurations of their resolved enantiomers, were determined using spectroscopic methods, single-crystal X-ray diffraction, and electronic circular dichroism calculations. The neuroprotective activity of the isolated compounds was evaluated against hydrogen peroxide-induced cellular damage in SH-SY5Y human neuroblastoma cells. Compounds (±)-1 and (±)-2 exhibited neuroprotective effects.

Triterpenoid Saponins from the Fruits of Symplocos lucida as ß-Glucuronidase Inhibitors.

A new triterpenoid saponin and five known ones were isolated from the fruits of Symplocos lucida (Thunb.) Siebold & Zucc. Their structures were determined based on the results of spectroscopy analysis, chemical conversions, and X-ray crystallographic analyses. The ß-glucuronidase-inhibitory effects of the isolated and semi-synthesized triterpenoid saponins were also examined.

Sex pheromones from male forewings of the Common Grass Yellow Eurema mandarina.

The common grass yellow Eurema mandarina has a characteristic patch (sex brand) composed of specialized scales (androconia) and wing intermembranous cells on the ventral surface of its male forewing. This structure is specific to males and is thought to release compounds that induce female mate acceptance. However, no study has demonstrated that these compounds function as sex pheromones in the genus Eurema. Here we report the identification of sex pheromones in males of E. mandarina. Chemical analyses revealed that 6,10,14-trimethylpentadecan-2-one (TMP) and (E/Z)-3,7,11,15-tetramethylhexadec-2-enal [(E/Z)-phytal] were male-specific and abundant in particular regions of the male forewings. TMP was highest in the sex brand, whereas (E/Z)-phytal was concentrated in the anal cell (cell 2 A), lacking androconia and intermembranous cells. The content of these compounds increases with age in males after emergence. In bioassays, virgin females displayed a posture of bending their abdomens as mating acceptance in response to stimulation by fresh male forewings. However, solvent-washed male wings did not induce such female responses, suggesting that some compounds from male wings serve as triggers. When we examined female responses to compounds applied to solvent-washed male wings, authentic TMP and (E/Z)-phytal alone showed little activity. However, the mixture elicited abdomen-bending responses in one-third of the females. Therefore, TMP and (E/Z)-phytal were found to act synergistically as aphrodisiac sex pheromones for E. mandarina females, although these activities were weak.

Electrospray ionization mass spectrometry and nuclear magnetic resonance spectroscopy data for anacardic acid derivatives.

The data presented here are related to the research paper entitled "Janohigenins: Long-chain anacardic acid derivatives with neuroprotective activity from Ophiopogon japonicus seeds" (Ohta et al., 2021). In this data article, we provide electrospray ionization mass spectrometry (ESIMS) and 1D and 2D nuclear magnetic resonance (NMR) spectroscopy data of four new anacardic acid derivatives, janohigenins isolated from the seeds of Ophiopogon japonicus.

Chemical Identity of Cuticular Lipid Components in the Mimetic Swallowtail Butterfly Papilio polytes.

The swallowtail Papilio polytes shows Batesian and female-limited polymorphic mimicry. In Japan, P. polytes females have two different forms: the cyrus form is non-mimetic and resembles males, whereas the polytes form mimics Pachliopta aristolochiae and Byasa (Atrophaneura) alcinous as unpalatable models. During mating, P. polytes males use cuticular lipids to distinguish non-mimetic females from conspecific males and sympatric sister species. In this study, we investigated whether compositional differences in cuticular lipids exist between mimetic and non-mimetic females of P. polytes and between mimetic females and their model species. The mimetic and non-mimetic females had nearly identical cuticular lipid profiles, which differed from those of males. The two model species exhibited sexually dimorphic and species-specific cuticular lipid compositions, which were distinctly different from those of mimetic P. polytes females. These results strongly suggest that P. polytes females maintain the identity of cuticular lipid profiles regardless of the mimicry type, and this feature helps males recognize mimetic females as the correct mating partners.

Paralemnolins X and Y, New Antimicrobial Sesquiterpenoids from the Soft Coral Paralemnalia thyrsoide.

The organic extracts of the Red Sea soft coral Paralemnalia thyrsoides has led to the identification of two neolemnane-type sesquiterpenoids: paralemnolins X and Y (1, 2). In addition to these newly characterized compounds, ten known metabolites (3-12) were isolated. Previously reported compounds were elucidated by literature comparison of spectroscopic data (1D and 2D NMR as well as MS data). In vitro antimicrobial activity was investigated for compounds (1-12) against Staphylococcus aureus, Escherichia coli, Candida albicans and Aspergillus niger. Compound 5 showed antimicrobial activity against all assayed microorganisms.

Oxygenated Cembrene Diterpenes from Sarcophyton convolutum: Cytotoxic Sarcoconvolutum A-E.

The soft coral genus Sarcophyton contains the enzymatic machinery to synthesize a multitude of cembrene-type diterpenes. Herein, highly oxygenated cembrenoids, sarcoconvolutum A-E (1-5) were purified and characterized from an ethyl acetate extract of the red sea soft coral, Sarcophyton convolutum. Compounds were assemblies according to spectroscopic methods including FTIR, 1D- and 2D-NMR as well as HRMS. Metabolite cytotoxicity was tested against lung adenocarcinoma, cervical cancer, and oral-cavity carcinoma (A549, HeLa and HSC-2, respectively). The most cytotoxic compound, (4) was observed to be active against cell lines A549 and HSC-2 with IC50 values of 49.70 and 53.17 µM, respectively.

Janohigenins: Long-chain anacardic acid derivatives with neuroprotective activity from Ophiopogon japonicus seeds.

Eight hitherto undescribed long-chain anacardic acid derivatives, janohigenins, were isolated from the endosperm of Ophiopogon japonicus seed, and their structures were elucidated employing spectroscopic and chemical methods. The neuroprotective activity of the isolated compounds was evaluated against rotenone-induced cellular damage in SH-SY5Y human neuroblastoma cells. Janohigenins exhibited noticeable neuroprotection at 1 µM.

Results of Mechanical Thrombectomy in Patients Aged ≥80 Years.

Objective: The effectiveness of mechanical thrombectomy (MT) for anterior circulation large vessel occlusion (LVO) is controversial in elderly patients. The aim of this study was to evaluate the efficacy of MT in octogenarians. Methods: One hundred and sixty-five patients who underwent MT for anterior circulation LVO between May 2014 and August 2019 at our institution were evaluated. Patients were divided into two groups, the elderly group (≥80 years) and non-elderly group (<80 years), and we compared the effective recanalization rate (Thrombolysis in Cerebral Infarction 2b-3), good outcome rate (modified Rankin Scale 0-2 at 90 days), time from groin puncture to recanalization (P to R), symptomatic intracranial hemorrhage (sICH), and mortality rate between them retrospectively. Eligible patients for MT were judged using the Japanese stroke guidelines, and the selection criteria were more carefully applied to elderly patients. Results: MT was performed on 48 elderly patients (29.1%) and 117 non-elderly patients (70.9%). On the other hand, 10 elderly patients (19.6%) and 5 non-elderly patients (5.4%) did not undergo MT even though they met the inclusion criteria. There were significantly fewer male patients and smokers in the elderly group, but other baseline and clinical characteristics were not significantly different between the groups. Effective recanalization (elderly 93.8% vs non-elderly 91.5%), good outcome (45.8% vs 60.7%), P to R (33.5 minutes vs 33.5 minutes), sICH (2.1% vs 4.3%), and mortality (8.3% vs 2.6%) were not significantly different between the two groups. Conclusion: When recanalization was achieved by strict preoperative evaluation of clinical conditions and imaging, MT may be safe and effective even for octogenarians or older patients.

Asaroidoxazines from the Roots of Asarum asaroides Induce Apoptosis in Human Neuroblastoma Cells.

Plants in the family Aristolochiaceae contain phenanthrene skeleton-containing chemical constituents that exhibit nephrotoxic, carcinogenic, mutagenic, anti-inflammatory, and cytotoxic effects. Two new phenanthrene-containing 1,2-oxazin-6-ones, designated as asaroidoxazine A (1) and asaroidoxazine B (2), and a known aristolactam, 5-methoxyaristololactam I (3), were isolated from the roots of Asarum asaroides. The structures of compounds 1 and 2 were determined using spectroscopic methods and X-ray crystallography. Treatment of SH-SY5Y human neuroblastoma cells with 1 µM of asaroidoxazine A (1) induced nuclear condensation as well as caspase-3/7 activation, indicating that this compound is a strong apoptosis inducer in neuronal cells. This is the first report of apoptosis induction by phenanthrene-containing oxazines.

Nuclear magnetic resonance spectroscopy and mass spectrometry data for sulfated isoguanine glycosides.

The data presented here are related to the research paper entitled "Rare sulfated purine alkaloid glycosides from Bruchidius dorsalis pupal case" [1]. In this data article, we provide 1D and 2D nuclear magnetic resonance (NMR) spectroscopy and electrospray ionization mass spectrometry (ESIMS) data of three undescribed sulfated purine alkaloids, locustoside A disulfate, saikachinoside B disulfate, and saikachinoside A trisulfate isolated from the pupal case of the wild bruchid seed beetle Bruchidius dorsalis (Chrysomelidae, Bruchinae) infesting the seed of Gleditsia japonica Miquel (Fabaceae).

Carotane sesquiterpenes from Ferula vesceritensis: in silico analysis as SARS-CoV-2 binding inhibitors.

Two sesquiterpenes, 8α-anisate-dauc-4-ene-3,9-dione (webiol anisate) (1) and 10α-acetoxy-6α-benzoate-jaeschkeanadiol (2) as well as, ten known analogues (3-10), and two sesquiterpene coumarins (11-12) were isolated from an organic root extract of Ferula vesceritensis (Fam. Apiaceae). Chemical structures were elucidated based on IR, 1D- and 2D-NMR and HRMS, spectroscopic analyses. With molecular overlap observed between two protease inhibitors that are being examined as anti-COVID-19 drugs, and sesquiterpenes isolated here, metabolite molecular docking calculations were made using the main protease (Mpro), which is required for viral multiplication as well as RNA-dependent RNA polymerase (RdRp). In silico binding-inhibition analysis predicted that select F. vesceritensis sesquiterpenes can bind to these enzymes required for viral replication. Structures of the isolated constituents were also consistent with the chemo-systematic grouping of F. vesceritensis secondary metabolites with other Ferula species.

NMR and ESIMS data for bisabolane-type sesquiterpenoids.

The data presented here are related to the research paper entitled "Norbisabolane and bisabolane sesquiterpenoids from the seeds of Angelica keiskei" [1]. In this data article, we provide 1D and 2D nuclear magnetic resonance (NMR) spectroscopy and electrospray ionization mass spectrometry (ESIMS) data of three undescribed norbisabolane- and bisabolene-type sesquiterpenoids, ashitabaol B-D isolated from the seeds of Angelica keiskei.

The Role of N,N,N-Trimethylglycine in Oviposition of Eurema mandarina on Albizia julibrissin.

The common grass yellow Eurema mandarina (Lepidoptera: Pieridae) uses the silk tree Albizia julibrissin (Fabaceae) as a primary host in Japan. We previously reported that D-pinitol, a cyclitol found in fresh leaves of A. julibrissin, solely elicits moderate oviposition responses from females. However, the aqueous neutral/amphoteric fraction of the fresh leaf extract containing D-pinitol weakly induces oviposition. Moreover, the aqueous neutral/amphoteric/basic fraction was significantly more active than the neutral/amphoteric fraction in eliciting responses, indicating that some basic compounds are involved in stimulating oviposition. High-resolution mass spectrometry and proton nuclear magnetic resonance measurements revealed that the aqueous basic faction contains N,N,N-trimethylglycine (trivial name: glycine betaine) in alkali metal salt form. The average concentration of this quaternary ammonium compound in fresh leaves was estimated to be 0.012% w/w in high performance liquid chromatography analyses. The authentic N,N,N-trimethylglycine induced oviposition at concentrations greater than 0.001% (w/v) and slightly enhanced female responses to the aqueous neutral fraction and authentic D-pinitol. However, its analogues, N,N-dimethylglycine, N-methylglycine, and glycine as well as its precursor choline were inactive. These results demonstrate that N,N,N-trimethylglycine, together with D-pinitol, serves as an stimulant of E. mandarina for oviposition on the leaves of A. julibrissin.