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.

Polymorphism of genes encoding drug-metabolizing and inflammation-related enzymes for susceptibility to cholangiocarcinoma in Thailand.

BACKGROUND: Cholangiocarcinoma (CCA) is an intractable cancer, and its incidence in northeastern Thailand is the highest worldwide. Infection with the liver fluke Opisthorchis viverrini (OV) has been associated with CCA risk. However, animal experiments have suggested that OV alone does not induce CCA, but its combination with a chemical carcinogen like nitrosamine can cause experimentally induced CCA in hamsters. Therefore, in humans, other environmental and genetic factors may also be involved. AIM: To examine relations between risk for CCA and genetic polymorphisms in carcinogen-metabolizing and inflammation-related genes. METHODS: This hospital-based case-control study enrolled 95 case-control pairs matched by age (± 5 years) and sex. We examined relations between risk for CCA and genetic polymorphisms in carcinogen-metabolizing and inflammation-related genes, serum anti-OV, alcohol consumption, and smoking. Polymorphisms of CYP2E1, IL-6 (-174 and -634), IL-10 (-819), and NF-κB (-94) and their co-occurrence with polymorphisms in the drug-metabolizing enzyme gene GSTT1 or GSTM1 were also analyzed. RESULTS: Although CCA risk was not significantly associated with any single polymorphism, persons with the GSTT1 wild-type and CYP2E1 c1/c2 + c2/c2 genotype had an increased risk (OR = 3.33, 95%CI: 1.23-9.00) as compared with persons having the GSTT1 wild-type and CYP2E1 c1/c1 wild genotype. The presence of anti-OV in serum was associated with a 7- to 11-fold increased risk, and smoking level was related to an OR of 1.5-1.8 in multivariable analyses adjusted for each of the seven genetic polymorphisms. CONCLUSION: In addition to infection with OV, gene-gene interactions may be considered as one of the risk factors for CCA development.

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.

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.

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.

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.

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).

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.

HPLC profiles and spectroscopic data of cassane-type furanoditerpenoids.

The data presented here are related to the research paper entitled "Hydroxylated furanoditerpenoids from the pupal case produced by the bruchid beetle Sulcobruchus sauteri inside the seed of Caesalpinia decapetala" (Akihara et al., 2018) [1]. In this data article, we provide high-performance liquid chromatography (HPLC) profiles of seven undescribed hydroxylated furanoditerpenoids, caesalsauteolide, 2-hydroxycaesaljapin, 2,7-dihydroxycaesaljapin, 2-hydroxycaesalacetal, caesalsauterol, 6-acetylcaesalsauterol, norcaesalsauterol isolated from the pupal cases produced by Sulcobruchus sauteri and four known compounds, caesaljaponin A (Kamikawa et al., 2015) [2], caesaljaponin B (Kamikawa et al., 2015) [2], caesalacetal (Kamikawa et al., 2016) [3], and caesaljapin (Kamikawa et al., 2016; Ogawa et al., 1992) [3], [4] isolated from the cotyledons of the intact seeds of Caesalpinia decapetala. Besides, 1D NMR, 2D NMR, and HRESIFTMS data of the seven undescribed furanoditerpenoids are also presented.

Hydroxylated furanoditerpenoids from pupal cases produced by the bruchid beetle Sulcobruchus sauteri inside the seeds of Caesalpinia decapetala.

Seven undescribed hydroxylated cassane-type furanoditerpenoids were isolated from pupal cases formed from the secretion/excretion of the larvae of the wild bruchid seed beetle Sulcobruchus sauteri in infested Caesalpinia decapetala seeds, and their structures were elucidated by interpreting their spectra. The hydroxylated furanoditerpenoids found in the pupal cases were not present in the seeds of the host plant. Caesalacetal and caesaljapin obtained from the intact seeds exhibited larvicidal activity against the larvae of Aedes albopictus, while the hydroxylated furanoditerpenoids isolated from the pupal cases were inactive. The larvae of S. sauteri are proposed to detoxify larvicidal diterpenoids that occur in the seeds of the host plant by regiospecific hydroxylation.

Sulfated Purine Alkaloid Glycosides from the Pupal Case Built by the Bruchid Beetle Bruchidius dorsalis Inside the Seed of Gleditsia japonica.

Three new sulfated isoguanine alkaloid glycosides, designated as saikachinoside A monosulfate (1), saikachinoside A disulfate (2), and locustoside B disulfate (3), have been isolated from the pupal case of the wild bruchid seed beetle Bruchidius dorsalis (Chrysomelidae, Bruchinae) infesting the seed of Gleditsia japonica Miq. (Fabaceae). Their structures were determined by spectroscopic methods and the inhibitory activity of 2 and 3 against acid phosphatase was evaluated.

Statistical description of the denatured structure of a single protein, staphylococcal nuclease, by FRET analysis.

Structural characterization of fully unfolded proteins is essential for understanding not only protein-folding mechanisms, but also the structures of intrinsically disordered proteins. Because an unfolded protein can assume all possible conformations, statistical descriptions of its structure are most appropriate. For this purpose, we applied Förster resonance energy transfer (FRET) analysis to fully unfolded staphylococcal nuclease. Artificial amino acids labeled with a FRET donor or acceptor were introduced by an amber codon and a four-base codon respectively. Eight double-labeled proteins were prepared, purified, and subjected to FRET analysis in 6 M urea. The observed behavior could be explained by a power law, R = αN0.44, where R, and N are the distance and the number of residues between donor and acceptor, and α is a coefficient. The index was smaller than the value expected for an excluded-volume random coil, 0.588, indicating that the fully unfolded proteins were more compact than polypeptides in good solvent. The FRET efficiency in the native state did not necessarily correlate to the distance obtained from crystal structure, suggesting that other factors such as the orientation factor made a substantial contribution to FRET.

Prenylated purine alkaloids from seeds of Gleditsia japonica.

Three previously undescribed isoguanine glycosides with an N3-prenyl group, designated locustoside B, saikachinoside B, and saikachinoside C, have been isolated from the seed of Gleditsia japonica Miquel (Fabaceae) along with two known compounds, locustoside A and saikachinoside A. Their structures were determined from spectroscopic data and X-ray crystallographic analysis. The inhibitory activity against acid phosphatase was evaluated.

New Prenylated ortho-Dihydroxycoumarins from the Fruits of Ficus nipponica.

Two new prenylated ortho-dihydroxycoumarins, designated fipsomin (1) and fipsotwin (2), were isolated from the fruits of Ficus nipponica together with a known prenylated coumarin, apigravin (3). Their structures were established by spectroscopic data and X-ray crystallographic analysis. Compound 1 exhibited antibacterial activity against Bacillus subtilis with an MIC value of 61 µm, while 2 and 3 showed very weak activity.

Ficusnotins A-F: Rare diarylbutanoids from the leaves of Ficus nota.

Six diarylbutanoids, designated as ficusnotins A-F, with a rare carbon skeleton consisting of two aromatic rings separated by an unbranched C4-chain have been isolated from the leaves of Ficus nota (Blanco) Merr. (Moraceae). The structures were determined on the basis of spectroscopic data, as well as X-ray crystallographic analysis. The isolated compounds were evaluated for their antibacterial activity against Bacillus subtilis.

Spurious Thrombocytosis Caused by Tumor Cell Lysis in a Patient with Acute Monocytic Leukemia.

BACKGROUND: Tumor lysis syndrome can occur after treatment of fast-growing cancers. Early detection of tumor lysis is crucial to minimize the toxic effects on organs and potentially life-threatening complications. METHODS: A patient with acute monocytic leukemia presented with spurious thrombocytosis. A peripheral blood smear was stained with alpha-naphthyl butyrate esterase to discriminate tumor cell fragments from platelets. RESULTS: Peripheral blood smears showed widespread leukemic cell fragmentation. Tumor lysis syndrome (TLS) after treatment for acute monocytic leukemia was diagnosed. The patient underwent chemo- and radiotherapy followed by umbilical cord blood transplantation and remains symptom-free two years after transplantation. CONCLUSIONS: For patients with thrombocytosis accompanied by bizarre scatter-grams on automatic hematologic analyzers, further diagnostic procedures should be performed to determine the exact cause of thrombocytosis.

Cassane diterpenoids from the roots of Caesalpinia decapetala var. japonica and structure revision of caesaljapin.

Two cassane-type furanoditerpenoids, designated caesalacetal and caesalpinetate, and a norditerpenoid designated caesalpinone were isolated from the roots of Caesalpinia decapetala var. japonica along with seven known diterpenoids. Structures were elucidated by interpretation of their spectroscopic data, and the absolute structure of caesalacetal was confirmed by X-ray crystallographic analysis. Furthermore, the structure of a previously reported furanoditerpenoid, caesaljapin, was revised as its C-4 epimer on the basis of detailed NMR spectroscopic data as well as X-ray crystallographic analysis.