Petiolins A-C, phloroglucinol derivatives from Hypericum pseudopetiolatum var. kiusianum

Naonobu Tanaka; Takaaki Kubota; Haruaki Ishiyama; Atsushi Araki; Yoshiki Kashiwada; Yoshihisa Takaishi; Yuzuru Mikami; Jun'ichi Kobayashi

doi:10.1016/j.bmc.2008.03.076

Petiolins A-C, phloroglucinol derivatives from Hypericum pseudopetiolatum var. kiusianum

Naonobu Tanaka, Takaaki Kubota, Haruaki Ishiyama, Atsushi Araki, Yoshiki Kashiwada, Yoshihisa Takaishi, Yuzuru Mikami, Jun'ichi Kobayashi

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

Abstract

Two new phloroglucinol derivatives possessing chromane skeleton, petiolins A (1) and B (2), and a new phloroglucinol derivative containing a dihydrofuran ring, petiolin C (3), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum. The gross structures of 1-3 were elucidated by spectroscopic data, and the relative stereochemistry of 3 was elucidated by NOESY data. Petiolins A-C (1-3) showed modest cytotoxicity, while petiolin C (3) exhibited antifungal activity.

Original language	English
Pages (from-to)	5619-5623
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry
Volume	16
Issue number	10
DOIs	https://doi.org/10.1016/j.bmc.2008.03.076
Publication status	Published - May 15 2008
Externally published	Yes

Keywords

Hypericum pseudopetiolatum var. kiusianum
Petiolins A-C
Phloroglucinol derivatives

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2008.03.076

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title = "Petiolins A-C, phloroglucinol derivatives from Hypericum pseudopetiolatum var. kiusianum",

abstract = "Two new phloroglucinol derivatives possessing chromane skeleton, petiolins A (1) and B (2), and a new phloroglucinol derivative containing a dihydrofuran ring, petiolin C (3), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum. The gross structures of 1-3 were elucidated by spectroscopic data, and the relative stereochemistry of 3 was elucidated by NOESY data. Petiolins A-C (1-3) showed modest cytotoxicity, while petiolin C (3) exhibited antifungal activity.",

keywords = "Hypericum pseudopetiolatum var. kiusianum, Petiolins A-C, Phloroglucinol derivatives",

author = "Naonobu Tanaka and Takaaki Kubota and Haruaki Ishiyama and Atsushi Araki and Yoshiki Kashiwada and Yoshihisa Takaishi and Yuzuru Mikami and Jun'ichi Kobayashi",

note = "Funding Information: We thank T. Akiyama and M. Inagaki, the Kochi Prefectural Makino Botanical Garden, for collection and botanical identification of the plant, S. OKa, A. Tokumitsu, and A. Miyao, Center for Instrumental Analysis, Hokkaido University, for measurements of HRFABMS. This work was partly supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan.",

year = "2008",

month = may,

day = "15",

doi = "10.1016/j.bmc.2008.03.076",

language = "English",

volume = "16",

pages = "5619--5623",

journal = "Bioorganic and Medicinal Chemistry",

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publisher = "Elsevier Limited",

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TY - JOUR

T1 - Petiolins A-C, phloroglucinol derivatives from Hypericum pseudopetiolatum var. kiusianum

AU - Tanaka, Naonobu

AU - Kubota, Takaaki

AU - Ishiyama, Haruaki

AU - Araki, Atsushi

AU - Kashiwada, Yoshiki

AU - Takaishi, Yoshihisa

AU - Mikami, Yuzuru

AU - Kobayashi, Jun'ichi

N1 - Funding Information: We thank T. Akiyama and M. Inagaki, the Kochi Prefectural Makino Botanical Garden, for collection and botanical identification of the plant, S. OKa, A. Tokumitsu, and A. Miyao, Center for Instrumental Analysis, Hokkaido University, for measurements of HRFABMS. This work was partly supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan.

PY - 2008/5/15

Y1 - 2008/5/15

N2 - Two new phloroglucinol derivatives possessing chromane skeleton, petiolins A (1) and B (2), and a new phloroglucinol derivative containing a dihydrofuran ring, petiolin C (3), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum. The gross structures of 1-3 were elucidated by spectroscopic data, and the relative stereochemistry of 3 was elucidated by NOESY data. Petiolins A-C (1-3) showed modest cytotoxicity, while petiolin C (3) exhibited antifungal activity.

AB - Two new phloroglucinol derivatives possessing chromane skeleton, petiolins A (1) and B (2), and a new phloroglucinol derivative containing a dihydrofuran ring, petiolin C (3), were isolated from aerial parts of Hypericum pseudopetiolatum var. kiusianum. The gross structures of 1-3 were elucidated by spectroscopic data, and the relative stereochemistry of 3 was elucidated by NOESY data. Petiolins A-C (1-3) showed modest cytotoxicity, while petiolin C (3) exhibited antifungal activity.

KW - Hypericum pseudopetiolatum var. kiusianum

KW - Petiolins A-C

KW - Phloroglucinol derivatives

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EP - 5623

JO - Bioorganic and Medicinal Chemistry

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Petiolins A-C, phloroglucinol derivatives from Hypericum pseudopetiolatum var. kiusianum

Abstract

Keywords

ASJC Scopus subject areas

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