4.7 Article

Chromone and chromanone glucosides from Hypericum sikokumontanum and their anti-Helicobacter pylori activities

Journal

PHYTOCHEMISTRY
Volume 70, Issue 1, Pages 141-146

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2008.11.006

Keywords

Hypericum sikokumontanum; Guttiferae; Chromone glucoside; Chromanone glucoside; Helicobacter pylori; Cytotoxicity

Ask authors/readers for more resources

Chromone glucosides, takanechromones A-C (1, 2 and S) and chromanone glucosides, named takanechromanones A and B (3 and 4), were isolated from the methanolic extracts of Hypericum sikokumontanum together with 27 known compounds. Their structures were established based on spectroscopic evidence. The isolated compounds and some chromone derivatives were assayed for antimicrobial activity against Helicobacter pylori and cytotoxicity against human cancer cell lines. (C) 2008 Elsevier Ltd. All rights reserved.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.7
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Chemistry, Medicinal

Lanostane-type triterpenes from the sclerotium of Inonotus obliquus (Chaga mushrooms) as proproliferative agents on human follicle dermal papilla cells

Kazumi Sagayama, Naonobu Tanaka, Takatoshi Fukumoto, Yoshiki Kashiwada

JOURNAL OF NATURAL MEDICINES (2019)

Article Chemistry, Medicinal

Prenylated benzophenone derivatives from Hypericum patulum

Naonobu Tanaka, Kanji Niwa, Yuki Yano, Yoshiki Kashiwada

JOURNAL OF NATURAL MEDICINES (2020)

Article Plant Sciences

Hypascyrins A-E, Prenylated Acylphloroglucinols from Hypericum ascyron

Kanji Niwa, Naonobu Tanaka, Yutaka Tatano, Hideki Yagi, Yoshiki Kashiwada

JOURNAL OF NATURAL PRODUCTS (2019)

Article Biochemistry & Molecular Biology

Linaburiosides A - D, acylated iridoid glucosides from Linaria buriatica

Kanji Niwa, Ren Yi, Naonobu Tanaka, Shindai Kitaguchi, Daisuke Tsuji, Sang-Yong Kim, Ariuntuya Tsogtbaatar, Perleidulam Bunddulam, Kazuyoshi Kawazoe, Mareshige Kojoma, Davaadagva Darndinjav, Kohji Itoh, Yoshiki Kashiwada

PHYTOCHEMISTRY (2020)

Article Chemistry, Medicinal

Agesasines A and B, Bromopyrrole Alkaloids from Marine SpongesAgelasspp

Sanghoon Lee, Naonobu Tanaka, Sakura Takahashi, Daisuke Tsuji, Sang-Yong Kim, Mareshige Kojoma, Kohji Itoh, Jun'ichi Kobayashi, Yoshiki Kashiwada

MARINE DRUGS (2020)

Article Chemistry, Organic

C28 Terpenoids from Lamiaceous Plant Perovskia scrophulariifolia: Their Structures and Anti-neuroinflammatory Activity

Naonobu Tanaka, Kanji Niwa, Seita Kajihara, Daisuke Tsuji, Kohji Itoh, Nilufar Z. Mamadalieva, Yoshiki Kashiwada

ORGANIC LETTERS (2020)

Review Chemistry, Medicinal

Characteristic metabolites of Hypericum plants: their chemical structures and biological activities

Naonobu Tanaka, Yoshiki Kashiwada

Summary: Plants of the genus Hypericum are a rich source of natural products with diverse chemical structures and intriguing biological activities. Over 100 new characteristic metabolites have been isolated from 11 Hypericum plants and one Triadenum plant collected in Japan, China, and Uzbekistan, or cultivated in Japan, including prenylated acylphloroglucinols, meroterpenes, ketides, dibenzo-1,4-dioxane derivatives, and xanthones. These compounds hold promise as potential lead compounds for therapeutic agents.

JOURNAL OF NATURAL MEDICINES (2021)

Article Chemistry, Organic

Mechanistic Support for Intramolecular Migrative Cyclization of Propargyl Sulfones Provided by Catalytic Asymmetric Induction with a Chiral Counter Cation Strategy

Kohta Yamasaki, Akiho Yamauchi, Tsubasa Inokuma, Yasunori Miyakawa, Yinli Wang, Raphael Oriez, Yousuke Yamaoka, Kiyosei Takasu, Naonobu Tanaka, Yoshiki Kashiwada, Ken-ichi Yamada

Summary: The study confirmed an enantioselective intramolecular migrative cyclization reaction, where the use of chiral nucleophiles led to enantiomerically enriched products.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Medicinal

Hyperdioxanes, dibenzo-1,4-dioxane derivatives from the roots of Hypericum ascyron

Kanji Niwa, Naonobu Tanaka, Yusei Shimomoto, Daisuke Tsuji, Sang-Yong Kim, Mareshige Kojoma, Kohji Itoh, Chin-Ho Chen, Kuo-Hsiung Lee, Yoshiki Kashiwada

Summary: Six dibenzo-1,4-dioxane derivatives were isolated from the roots of a Hypericaceous plant, with 2 and 4-6 being new compounds. Chiral HPLC analyses confirmed the partial racemic natures of 1-3, while 5 was identified as a racemate. The absolute configurations of 1-4 were deduced based on ECD calculations. Additionally, compound 7 exhibited anti-HIV activity and compound 8 showed inhibitory effects on IL-1 beta production from LPS-stimulated microglial cells.

JOURNAL OF NATURAL MEDICINES (2021)

Review Chemistry, Medicinal

Phytochemical studies on traditional herbal medicines based on the ethnopharmacological information obtained by field studies

Naonobu Tanaka, Yoshiki Kashiwada

Summary: Traditional herbal medicines are valuable resources of drug seeds, and ethnobotanical and ethnopharmacological surveys can provide useful information for searching new bioactive molecules. Studies have been conducted in regions such as Yunnan Province, Guangxi Zhuang Autonomous Region, Uzbekistan, and Bangladesh to investigate traditional herbal medicines and search for active substances through bioassay-guided fractionation and isolation, resulting in the isolation of more than 150 new molecules with various biological activities.

JOURNAL OF NATURAL MEDICINES (2021)

Article Chemistry, Multidisciplinary

Late-stage macrolactonisation enabled by tandem acyl transfers followed by desulphurisation

Daiki Sato, Masaya Denda, Honoka Tsunematsu, Naonobu Tanaka, Isamu Konishi, Chiaki Komiya, Akira Shigenaga, Akira Otaka

Summary: Intramolecular S-acylation of a thiol-installed threonine with a thioester unit, followed by S-O acyl transfer and subsequent desulphurisation allows the synthesis of lactone peptides. A protocol has been developed enabling the cyclisation of a linear peptide, a reaction which has not been achieved by conventional methods.

CHEMICAL COMMUNICATIONS (2022)

Article Plant Sciences

Lanicepines A and B, Sesquiterpenes with Amino Acid-Derived Substituents from the Flowering Aerial Parts of Saussurea laniceps

Naonobu Tanaka, Yuki Yoshino, Fusako Nakano, Shin-Ichiro Kurimoto, Kazuyoshi Kawazoe, Daisuke Tsuji, Kohji Itoh, Shun-Lin Li, Han-Dong Sun, Yoshihisa Takaishi, Yoshiki Kashiwada

Summary: In this study, two new guaianolide sesquiterpenes were isolated from Saussurea laniceps, a traditional herbal medicine. The structures of these compounds were determined through spectroscopic analysis and computational methods. Furthermore, these compounds exhibited inhibitory activity against IL-1 beta production from LPS-stimulated microglial cells.

JOURNAL OF NATURAL PRODUCTS (2022)

Article Chemistry, Medicinal

Communiferulins, farnesylated coumarins from the roots of Ferula communis and their anti-neuroinflammatory activity

Yuki Yoshino, Naonobu Tanaka, Daisuke Tsuji, Kohji Itoh, Yoshiki Kashiwada

Summary: Three new farnesylated coumarins and one farnesylated chromone were isolated from the roots of Ferula communis. Their structures and relative configurations were determined by spectroscopic analysis and NMR data calculation. These compounds showed inhibitory activities on IL-1 beta production from LPS-stimulated microglial cells.

JOURNAL OF NATURAL MEDICINES (2023)

Article Biochemistry & Molecular Biology

Betuletol, a Propolis Component, Suppresses IL-33 Gene Expression and Effective against Eosinophilia

Aurpita Shaha, Rezwanul Islam, Naonobu Tanaka, Yoshiki Kashiwada, Hiroyuki Fukui, Noriaki Takeda, Yoshiaki Kitamura, Hiroyuki Mizuguchi

Summary: The active compound betuletol found in Brazilian green propolis can suppress the expression of the allergic gene IL-33 and reduce eosinophilia. It also inhibits the phosphorylation of ERK, indicating its potential in treating IL-33 mediated eosinophilic chronic inflammation.

MOLECULES (2022)

Article Plant Sciences

Tigliane-Type Diterpene Esters from the Fruits of Shirakiopsis indica and Their Anti-HIV Activity

Naonobu Tanaka, Sakura Takahashi, Yuki Yoshino, Megumi Nakatani, Fakhruddin Ali Ahmed, Gazi Mosharof Hossain, Chin-Ho Chen, Kuo-Hsiung Lee, Yoshiki Kashiwada

Summary: Four new diterpene esters were isolated from the fruits of Shirakiopsis indica and their structures were determined. Among them, shirakindican A and B possess unique structures. In addition, the antiviral activity against HIV was evaluated, and sapintoxins A and D showed significant activity.

JOURNAL OF NATURAL PRODUCTS (2022)

Article Biochemistry & Molecular Biology

Inhibition of multidrug-resistant MCF-7 breast cancer cells with combinations of clinical drugs and resin glycosides from Operculina hamiltonii

Armando Moreno-Velasco, Mabel Fragoso-Serrano, Pedro de Jesus Flores-Tafoya, Sebastian Carrillo-Rojas, Elihu Bautista, Suzana Guimara Leitao, Jhon F. Castaneda-Gomez, Rogelio Pereda-Miranda

Summary: This study investigated the roots of Operculina hamiltonii, a traditional medicinal plant in Brazil. Three new acyl sugars or resin glycosides were identified and their structures elucidated. The combination of these compounds with other drugs showed enhanced cytotoxic effects on breast cancer cells.

PHYTOCHEMISTRY (2024)

Article Biochemistry & Molecular Biology

Rare 7,9′-dinorlignans with neuroprotective activity from the roots of Lindera aggregata (Sims) Kosterm

Qian-Qing Liu, Lin-An Xiong, Jia-Yu Qian, Ting-Ting Gong, Lie-Feng Ma, Luo Fang, Zha-Jun Zhan

Summary: A new naturally occurring compound, Linderagatins C-F (1-4), with the structures of diaryltetrahydrofuran-type 7,9'-dinorlignans, was discovered in the roots of Lindera aggregata. The neuroprotective effects of compounds 2 and 3 on erastin-induced ferroptosis in HT-22 cells were found to be significant.

PHYTOCHEMISTRY (2024)