Publications by authors named "Junei Kinjo"

Ipomoea alba L. (Convolvulaceae) is an annual vine native to tropical America that is cultivated primarily for ornamental purposes. Its seeds are used in traditional medicine as a laxative, and young shoots are consumed as food.

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During the screening of novel chemotherapeutic candidates from plants against adult T-cell leukaemia/lymphoma (ATL), we found that extracts of plants in the Solanaceae, Annonaceae, Apocynaceae, and Rutaceae families showed anti-proliferative activity in the MT-1 and MT-2 cell lines. We have isolated active compounds from these plants in the present research because Cupressaceae plants showed potent anti-proliferative activity in the cell lines. We attempted to isolate the active compounds from the leaves of .

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Resin glycosides are characteristic of plants of the Convolvulaceae family and are well-known purgative ingredients in crude drugs, such as Rhizoma Jalapae, Orizaba Jalapa Tuber, and Pharbitidis Semen, which are used in traditional medicine and derived from plants belonging to this family. Isolated resin glycosides have demonstrated diverse biological activities, including antibacterial, ionophoric, anti-inflammatory, antiviral, and multidrug-resistance-modulating properties, as well as cytotoxicity against cancer cells. These compounds consist of hydroxyl fatty acid oligoglycosides (glycosidic acids), with portions of the saccharide moieties acylated with some organic acids to form the core structure.

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Article Synopsis
  • Resin glycosides from the Convolvulaceae family, particularly those in Ipomoea alba seeds, possess laxative, antibacterial, and anticancer properties.
  • Through alkaline and acidic hydrolysis of the methanol extract, various organic and glycosidic acid components were identified, including several new compounds.
  • Structural analysis using MS and NMR techniques revealed unique glycosidic linkages, with some new natural glycosides featuring multiple linkages to a single monosaccharide.
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Ipomoea muricata (L.) Jacq. seeds (Convolvulaceae) are used as a traditional laxative and carminative medicine.

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Resin glycosides are commonly found in plants belonging to the Convolvulaceae family. Ipomoea lacunosa L. (Convolvulaceae) is an herbaceous vine native to the United States.

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Biological effects attributed to resin glycosides, including cytotoxicity against cancer cells and antibacterial, multidrug resistance-modulating, and antiviral activities have been documented. Penta-glycosides composed of calysolic acid A or calyhedic acid A, which are glycosidic acid components of the crude resin glycoside fraction of Calystegia hederacea, have not yet been isolated from this plant. In this study, eight new resin glycosides, termed calyhedins XVI (1)-XXIII (8), were isolated from the rhizomes of C.

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Calystegia hederacea Wall. (Convolvulaceae) is a perennial herbaceous vine that grows widely in India and East Asia. All parts of this plant are used to treat various disorders such as menoxenia and gonorrhea.

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Adult T-cell leukemia/lymphoma (ATL) is a malignancy of mature peripheral T-lymphocytes caused by human T-cell leukemia virus type I (HTLV-I). There are an estimated 5-20 million HTLV-1-infected individuals worldwide. Conventional chemotherapeutic regimens used against other malignant lymphomas have been administered to patients with ATL, but the therapeutic outcomes of acute and lymphoma-type ATL remain extremely poor.

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The alkaline hydrolysis of the crude resin glycoside fraction from the leaves and stems of the plant Calystegia japonica Choisy (Convolvulaceae) yielded organic acid and glycosidic acid fractions. The organic acid fraction was esterified with p-bromophenacyl bromide to obtain p-bromophenacyl 2R-methyl-3R-hydroxybutyrate (1) and p-bromophenacyl (E)-2-methylbut-2-enoate (2). By treating the glycosidic acid fraction with trimethylsilyldiazomethane-hexane, seven new methyl esters of glycosidic acids, namely calyjaponic acid A methyl ester (3) calyjaponic acid B methyl ester (5), calyjaponic acid C methyl ester (6), calyjaponic acid D methyl ester (7), calyjaponic acid E methyl ester (8), calyjaponic acid F methyl ester (9), and calyjaponic acid G methyl ester (10), were isolated along with one known ester (4).

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Two new resin glycosides, muricatins XII () and XIII (), were isolated from the crude resin glycoside fraction of the seeds of (L.) Jacq. (Convolvulaceae), along with three known ones, muricatins V (), VI (), and IX ().

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Article Synopsis
  • - The study screened extracts from the Cupressaceae family for anti-cancer properties and found significant anti-proliferative effects on adult T-cell leukemia/lymphoma cells (MT-1 and MT-2).
  • - Researchers isolated 32 compounds, including lignans, terpenoids, and flavonoids, determining their structures using spectroscopic analysis, and discovered that lignans were the most effective in inhibiting cell growth.
  • - Findings suggest that specific structural features, like trans-lactone linkages in lignans and ketone moieties in diterpenes, enhance anti-cancer activity, indicating that these compounds could be potential treatments for adult T-cell leukemia/lymphoma.
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Four new resin glycosides with macrolactone structures (jalapins), namely, calyhedins VII ()-X (), were isolated from the rhizomes of Wall. (Convolvulaceae). The structures of - were determined based on spectroscopic data.

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Article Synopsis
  • Six new resin glycosides, called calyhedins I-VI, were discovered in the rhizomes of Calystegia hederacea, marking the first identification of these compounds from this plant.
  • The structures of these glycosides were analyzed using spectroscopic methods and chemical data, revealing macrolactone characteristics and unique sugar modifications.
  • Calyhedins II and III showed significant cytotoxic effects on human leukemia cells, comparable to the standard treatment drug cisplatin.
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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.

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Alkaline hydrolysis of crude resin glycoside fraction of the seeds of Ipomoea muricata (L.) Jacq. (Convolvulaceae) yielded a new glycosidic acid, muricatic acid D; three known glycosidic acids, namely, muricatic acids A, B, and C; and three known organic acids, namely, isobutyric, 2S-methylbutyric, and 2S-methyl-3S-hydroxybutyric acid.

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In the course of our screening program for novel chemotherapeutic candidates from plants against adult T-cell leukemia/lymphoma, the extracts of Asclepias curassavica L. showed potent activity against MT-1 and MT-2 cells. Therefore, we attempted to isolate their active components.

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A new cholestane-type steroidal glycoside, solamyriaside A (), was isolated from the fruits of Dunal (Solanaceae), along with two known steroidal glycosides, namely, solaviaside A () and aculeatiside A (), and three known steroidal alkaloid glycosides, namely, solamargine (), khasianine () and solasonine (), which were isolated for the first time from this plant. Based on spectroscopic data as well as chemical evidence, was determined to be 3--α-L-rhamnopyranosyl-(1→2)--[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl-22,25-cholest-5-ene-3β,16α,22,26-tetraol 26--β-D-glucopyranoside. The cytotoxic activity of - against HL-60 human promyelocytic leukaemia cells was examined.

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Article Synopsis
  • Two new glycosidic acids, calyhedic acids E and F, were isolated from a resin glycoside fraction derived from whole plants of a specific species.
  • Their structures were determined to be complex glycosides with multiple sugar units, specifically characterized by a long hydrocarbon chain with hydroxyl groups.
  • The identification of these compounds was based on detailed spectroscopic analysis, revealing structural differences between acids E and F.
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Two new oleanane-type triterpenoids with an epoxy bridge between C-3 and C-25, named lantacamaric acids A and B, were isolated from the leaves and stems of L. (Verbenaceae). In addition, seven known triterpenoids, two known iridoid glycosides, four known phenylethanoid glycosides, one known flavonoid glycoside, and one known cyanogenic glycoside were isolated.

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Article Synopsis
  • Resin glycosides, found in convolvulaceous plants, are known for their purgative properties and Calystegia hederacea, a widespread vine in India and East Asia, is used medicinally for various conditions.
  • Alkaline hydrolysis of its crude resin glycoside fraction produced four new glycosidic acids (calyhedic acids A, B, C, and D) and other known acids, with their structures characterized through spectroscopic methods.
  • Cytotoxic activity tests revealed that the crude resin glycoside fraction and certain macrolactone-type resin glycosides showed significant effects against human leukemia cells, while other variants exhibited weaker or no activity, highlighting the importance of structure in their effectiveness.
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Δ-Tetrahydrocannabinol (THC) is known to have various pharmacological effects mediated through activation of cannabinoid CB and CB receptors in rodents. In adult rats, 22- and 50-kHz ultrasonic vocalizations (USVs) serve as an effective communication system and as indicators of negative and positive states, respectively. The present study was performed to determine whether THC affects USVs in adult rats, and to determine the roles of cannabinoid receptors in these effects.

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Two new triterpene glycosides, 24-deoxyoxytrogenin 3-O-α-L-rhamnopyranosyl (1→2)[β-D-glucopyranosyl]-β-D-galactopyranosyl (1→2)-β-D-glucuronopyranoside and sophoradiol 3-O-α-L-rhamnopyranosyl (1→2)-β-D-glucuronopyranosyl (1→2)-β-D-glucuronopyranoside with four known glycosides were isolated from a Chinese natural medicine, the roots of Uraria crinita (L.) DESV. Their structures were determined by chemical and spectral methods.

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Seven new resin glycosides, multifidins III (1)-IX (7), were isolated from the seeds of Quamoclit × multifida (syn. Q. sloteri House) (Convolvulaceae), along with five known glycosides, quamoclinic acid B methyl ester (8), operculin XIII (9), quamoclin I (10), QM-10 (11), and QM-12 (12).

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Four new resin glycosides having macrolactone structures (jalapins), murasakimasarins I-IV, were isolated from the tubers of Ipomoea batatas (L.) Lam. ('Murasakimasari', Convolvulaceae), along with three known glycosides.

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