Tetrahydrofuran lignans: Melanogenesis inhibitors from Premna integrifolia wood collected in Myanmar

Nwet Nwet Win; So Yeun Woo; Hla Ngwe; Prema; Chin Piow Wong; Takuya Ito; Yasuko Okamoto; Masami Tanaka; Hiroshi Imagawa; Yoshinori Asakawa; Ikuro Abe; Hiroyuki Morita

doi:10.1016/j.fitote.2018.03.002

Tetrahydrofuran lignans: Melanogenesis inhibitors from Premna integrifolia wood collected in Myanmar

Nwet Nwet Win^*, So Yeun Woo, Hla Ngwe, Prema, Chin Piow Wong, Takuya Ito, Yasuko Okamoto, Masami Tanaka, Hiroshi Imagawa, Yoshinori Asakawa, Ikuro Abe, Hiroyuki Morita

^*Corresponding author for this work

Section of Natural Products & Drug Discovery, Division of Medicinal Resources, Institute of Natural Medicine

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

20 Scopus citations

Abstract

Two new tetrahydrofuran lignans, taungtangyiols A (1) and B (2), and eight known furofuran lignans (3−10), were isolated from the chloroform extract of Premna integrifolia wood collected in Myanmar. Their structures were elucidated by extensive spectroscopic techniques. The X-ray crystal structure of 1 clearly indicated its relative configuration. Taungtangyiols A (1) and B (2) inhibited the deposition of melanin in B16F10 mouse melanoma cells, with IC₅₀ values of 50.7 and 40.9 μM, respectively, without notable cytotoxicity. An SAR study demonstrated that the furofuran and dioxymethylene moieties of the lignans play a vital role in inhibiting melanogenesis.

Original language	English
Pages (from-to)	308-313
Number of pages	6
Journal	Fitoterapia
Volume	127
DOIs	https://doi.org/10.1016/j.fitote.2018.03.002
State	Published - 2018/06

Keywords

Melanogenesis inhibitory activity
Premna integrifolia
Taungtangyiol
Tetrahydrofuran lignan

ASJC Scopus subject areas

Pharmacology
Drug Discovery

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10.1016/j.fitote.2018.03.002

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@article{26bee97679534b379eb439bc6fb5894d,

title = "Tetrahydrofuran lignans: Melanogenesis inhibitors from Premna integrifolia wood collected in Myanmar",

abstract = "Two new tetrahydrofuran lignans, taungtangyiols A (1) and B (2), and eight known furofuran lignans (3−10), were isolated from the chloroform extract of Premna integrifolia wood collected in Myanmar. Their structures were elucidated by extensive spectroscopic techniques. The X-ray crystal structure of 1 clearly indicated its relative configuration. Taungtangyiols A (1) and B (2) inhibited the deposition of melanin in B16F10 mouse melanoma cells, with IC50 values of 50.7 and 40.9 μM, respectively, without notable cytotoxicity. An SAR study demonstrated that the furofuran and dioxymethylene moieties of the lignans play a vital role in inhibiting melanogenesis.",

keywords = "Melanogenesis inhibitory activity, Premna integrifolia, Taungtangyiol, Tetrahydrofuran lignan",

author = "Win, {Nwet Nwet} and Woo, {So Yeun} and Hla Ngwe and Prema and Wong, {Chin Piow} and Takuya Ito and Yasuko Okamoto and Masami Tanaka and Hiroshi Imagawa and Yoshinori Asakawa and Ikuro Abe and Hiroyuki Morita",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier B.V.",

year = "2018",

month = jun,

doi = "10.1016/j.fitote.2018.03.002",

language = "英語",

volume = "127",

pages = "308--313",

journal = "Fitoterapia",

issn = "0367-326X",

publisher = "Elsevier B.V.",

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TY - JOUR

T1 - Tetrahydrofuran lignans

T2 - Melanogenesis inhibitors from Premna integrifolia wood collected in Myanmar

AU - Win, Nwet Nwet

AU - Woo, So Yeun

AU - Ngwe, Hla

AU - Prema,

AU - Wong, Chin Piow

AU - Ito, Takuya

AU - Okamoto, Yasuko

AU - Tanaka, Masami

AU - Imagawa, Hiroshi

AU - Asakawa, Yoshinori

AU - Abe, Ikuro

AU - Morita, Hiroyuki

PY - 2018/6

Y1 - 2018/6

N2 - Two new tetrahydrofuran lignans, taungtangyiols A (1) and B (2), and eight known furofuran lignans (3−10), were isolated from the chloroform extract of Premna integrifolia wood collected in Myanmar. Their structures were elucidated by extensive spectroscopic techniques. The X-ray crystal structure of 1 clearly indicated its relative configuration. Taungtangyiols A (1) and B (2) inhibited the deposition of melanin in B16F10 mouse melanoma cells, with IC50 values of 50.7 and 40.9 μM, respectively, without notable cytotoxicity. An SAR study demonstrated that the furofuran and dioxymethylene moieties of the lignans play a vital role in inhibiting melanogenesis.

AB - Two new tetrahydrofuran lignans, taungtangyiols A (1) and B (2), and eight known furofuran lignans (3−10), were isolated from the chloroform extract of Premna integrifolia wood collected in Myanmar. Their structures were elucidated by extensive spectroscopic techniques. The X-ray crystal structure of 1 clearly indicated its relative configuration. Taungtangyiols A (1) and B (2) inhibited the deposition of melanin in B16F10 mouse melanoma cells, with IC50 values of 50.7 and 40.9 μM, respectively, without notable cytotoxicity. An SAR study demonstrated that the furofuran and dioxymethylene moieties of the lignans play a vital role in inhibiting melanogenesis.

KW - Melanogenesis inhibitory activity

KW - Premna integrifolia

KW - Taungtangyiol

KW - Tetrahydrofuran lignan

UR - http://www.scopus.com/inward/record.url?scp=85043992243&partnerID=8YFLogxK

U2 - 10.1016/j.fitote.2018.03.002

DO - 10.1016/j.fitote.2018.03.002

M3 - 学術論文

C2 - 29540314

AN - SCOPUS:85043992243

SN - 0367-326X

VL - 127

SP - 308

EP - 313

JO - Fitoterapia

JF - Fitoterapia

ER -

Tetrahydrofuran lignans: Melanogenesis inhibitors from Premna integrifolia wood collected in Myanmar

Abstract

Keywords

ASJC Scopus subject areas

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