Highly Oxygenated Limonoids and Lignans from Phyllanthus flexuosus

doi:10.1007/s13659-014-0026-2

应用天然产物 ›› 2014, Vol. 4 ›› Issue (4): 233-242.DOI: 10.1007/s13659-014-0026-2

Highly Oxygenated Limonoids and Lignans from Phyllanthus flexuosus

Jian-Qiang Zhao^1,2, Yan-Ming Wang^1,2, Hong-Tao Zhu¹, Dong Wang¹, Sheng-Hong Li¹, Rong-Rong Cheng¹, Chong-Ren Yang¹, Yi-Fei Wang³, Min Xu¹, Ying-Jun Zhang¹

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2. University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3. Guangzhou Jinan Biomedicine Research and Development Center, Guangzhou 510632, People's Republic of China

收稿日期:2014-05-07 修回日期:2014-05-29 出版日期:2014-08-24 发布日期:2018-02-11
通讯作者: ,Min Xu,e-mail:xumin@mail.kib.ac.cn;Ying-Jun Zhang,e-mail:zhangyj@mail.kib.ac.cn
基金资助:
We are grateful to the members of the analytical group of our institute for the measurement of spectroscopic data. This work was supported by the NSFC 21002105, the 973 Program of Science and Technology of P. R. China(2011CB915503), the Fourteenth Batch Candidates of the Young Academic Leaders of Yunnan Province(Min XU, 2011CI044) and by West Light Foundation of the Chinese Academy of Sciences.

Highly Oxygenated Limonoids and Lignans from Phyllanthus flexuosus

Jian-Qiang Zhao^1,2, Yan-Ming Wang^1,2, Hong-Tao Zhu¹, Dong Wang¹, Sheng-Hong Li¹, Rong-Rong Cheng¹, Chong-Ren Yang¹, Yi-Fei Wang³, Min Xu¹, Ying-Jun Zhang¹

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2. University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3. Guangzhou Jinan Biomedicine Research and Development Center, Guangzhou 510632, People's Republic of China

Received:2014-05-07 Revised:2014-05-29 Online:2014-08-24 Published:2018-02-11
Supported by:
We are grateful to the members of the analytical group of our institute for the measurement of spectroscopic data. This work was supported by the NSFC 21002105, the 973 Program of Science and Technology of P. R. China(2011CB915503), the Fourteenth Batch Candidates of the Young Academic Leaders of Yunnan Province(Min XU, 2011CI044) and by West Light Foundation of the Chinese Academy of Sciences.

摘要/Abstract

摘要： Two new highly oxygenated limonoids, flexuosoids A(1) and B(2), and three new arylnaphthalene lignan glycosides, phyllanthusmins D-F(3-5), were isolated from the roots of Phyllanthus flexuosus, in addition to three known lignans, phyllanthusmin C, arabelline, and(+)-diasyringaresinol. Their structures were elucidated on the basis of detailed spectroscopic analysis and chemical methods. Compounds 1 and 2, two new decaoxygenated limonoids with a C-19/29 lactol bridge and heptaoxygenated substituents at C-1, C-2, C-3, C-7, C-11, C-17, and C-30, represent the second example of limonoids in the Euphorbiaceae family. Most of the isolates were tested for their antifeedant, anti-herpes simplex virus 1, and cytotoxic activities. The new limonoids 1 and 2 showed promising antifeedant activity against the beet army worm(Spodoptera exigua) with EC₅₀ values of 25.1 and 17.3 μg/cm², respectively. In addition, both of them displayed moderate cytotoxicity against the ECA109 human esophagus cancer cell line, along with the known lignan glycoside, phyllanthusmin C, with the IC₅₀ values of 11.5(1), 8.5(2), and 7.8(phyllanthusmin C) μM, respectively.

关键词: Phyllanthus flexuosus, Euphorbiaceae, Limonoids, Lignan glycosides, Antifeedant, Antiviral, Cytotoxicity

Abstract: Two new highly oxygenated limonoids, flexuosoids A(1) and B(2), and three new arylnaphthalene lignan glycosides, phyllanthusmins D-F(3-5), were isolated from the roots of Phyllanthus flexuosus, in addition to three known lignans, phyllanthusmin C, arabelline, and(+)-diasyringaresinol. Their structures were elucidated on the basis of detailed spectroscopic analysis and chemical methods. Compounds 1 and 2, two new decaoxygenated limonoids with a C-19/29 lactol bridge and heptaoxygenated substituents at C-1, C-2, C-3, C-7, C-11, C-17, and C-30, represent the second example of limonoids in the Euphorbiaceae family. Most of the isolates were tested for their antifeedant, anti-herpes simplex virus 1, and cytotoxic activities. The new limonoids 1 and 2 showed promising antifeedant activity against the beet army worm(Spodoptera exigua) with EC₅₀ values of 25.1 and 17.3 μg/cm², respectively. In addition, both of them displayed moderate cytotoxicity against the ECA109 human esophagus cancer cell line, along with the known lignan glycoside, phyllanthusmin C, with the IC₅₀ values of 11.5(1), 8.5(2), and 7.8(phyllanthusmin C) μM, respectively.

Key words: Phyllanthus flexuosus, Euphorbiaceae, Limonoids, Lignan glycosides, Antifeedant, Antiviral, Cytotoxicity

Jian-Qiang Zhao, Yan-Ming Wang, Hong-Tao Zhu, Dong Wang, Sheng-Hong Li, Rong-Rong Cheng, Chong-Ren Yang, Yi-Fei Wang, Min Xu, Ying-Jun Zhang. Highly Oxygenated Limonoids and Lignans from Phyllanthus flexuosus[J]. 应用天然产物, 2014, 4(4): 233-242.

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Highly Oxygenated Limonoids and Lignans from Phyllanthus flexuosus

Highly Oxygenated Limonoids and Lignans from Phyllanthus flexuosus

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