A Novel Prieurianin-Type Limonoid from Munronia pinnata

doi:10.6023/cjoc202604025

Chinese Journal of Organic Chemistry Previous Articles Next Articles

NOTE

矮陀陀中一个新的prieurianin型柠檬苦素类化合物

羊学荣^a, 李健星^a, 柏田良树^b, 田中直伸^b, 李典鹏^c,*

^a广西卫生职业技术学院药学院广西南宁 530023;
^b德岛大学药学院日本德岛 770-8505;
^c广西科学院广西南宁 530200

收稿日期:2026-04-16 修回日期:2026-06-25
基金资助:
广西歧黄学者资助项目 (GXQH202401)、广西重点研发计划项目(FN2600640439)、广西卫生职业技术学院高层次人才项目(GXWZY202501)、广西植物功能物质与资源持续利用重点实验室主任基金(ZRJJ2024-15).

A Novel Prieurianin-Type Limonoid from Munronia pinnata

Yang Xuerong^a, Li Jianxing^a, Yoshiki Kashiwada^b, Naonobu Tanaka^b, Li Dianpeng^c,*

^aSchool of Pharmacy, Guangxi health science college, Nanning 530023, China;
^bGraduate School of Pharmaceutical Sciences, Tokushima University, Tokushima 770-8505, Japan;
^cGuangxi Academy of Sciences, Nanning 530007, China

Received:2026-04-16 Revised:2026-06-25
Contact: *E-mail: phytoldp@hotmail.com
Supported by:
Guangxi Qi Huang Scholar Support Program (GXQH202401), Guangxi Key Research and Development Program ( FN2600640439), Guangxi Health Science College High-level Talents Project (GXWZY202501), and the Foundation of Guangxi Key Laboratory of Plant Functional Phytochemicals and Sustainable Utilization (ZRJJ2024-15).

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Abstract

This study aimed to investigate the chemical components of the traditional medicinal plant Munronia pinnata (Meliaceae). We sought to discover new limonoids and evaluate their biological activities. Compounds were isolated from the plant's aerial parts using 95% ethanol and chromatographic techniques. Their structures were identified by NMR and HRESIMS analysis, along with time-dependent density functional theory-electronic circular dichroism (TDDFT-ECD) computations. Cytotoxicity was tested with the CCK-8 assay, and anti-inflammatory activity was measured using the Griess method. A new limonoid, named munropin K (1), was obtained. Its structure features a prieurianin-type skeleton with a unique side chain at C-17. This side chain is a 20,22-dihydroxy-21,23-dimethoxytetrahydrofuran. At 80 µM, the compound showed no significant activity against several human cancer cell lines. These cell lines included A549, HepG2, MCF-7, and HCT116. It also did not show activity in an LPS-induced RAW 264.7 macrophage inflammation model. The research expands the known chemical diversity of the Munronia genus. It provides a chemical basis for future studies on structure modification and activity exploration of this new skeleton.

Key words: Munronia pinnata, Meliaceae, limonoid, structural elucidation, anti-inflammatory activity, cytotoxicity

Cite this article

Yang Xuerong, Li Jianxing, Yoshiki Kashiwada, Naonobu Tanaka, Li Dianpeng. A Novel Prieurianin-Type Limonoid from Munronia pinnata[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202604025.

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[1] Qi S. H.; Wu D. G.; Chen L.; Ma Y. B.; Luo X. D.J. Agric.Food Chem. 2003, 51, 6949-6952.
[2] Wang G.Q.Compilation of China Medicinal Herbal; People's Medical Publishing House: Beijing, China, 1975; Vol. 2, p. 1081 (in Chinese).
(王光清,《中国药用植物志》,北京:人民卫生出版社,1975, 第2卷,第1081页.)
[3] Guangxi Institute of Botany. Flora of Guangxi: Volume 3 Spermatophyta; Guangxi Science & Technology Publishing House: Nanning, China, 2011; p. 333 (in Chinese).
(广西植物研究所,《广西植物志:第三卷种子植物》,南宁:广西科学技术出版社, 2011, 第333页.)
[4] Su L.; Huang L. Z.; Cai Y.J. Youjiang Med. Univ. Natl. 2021, 43, 741-745 (in Chinese).
(苏玲, 黄丽贞, 蔡毅, 右江民族医学院学报, 2021, 43, 741-745.)
[5] Huang M. H.; Zhang Y. M.; Li J.; Shao F.; Yang M.; Zhang, P. Z. Chin. Tradit. Herb. Drugs,2017, 48, 1240-1249.
(黄美华, 张亚梅, 李菁, 邵峰, 杨明, 张普照.中草药, 2017, 48, 1240-1249.)
[6] Li X. L.; He Q. X.; Zhang F. L.; Zhao Y. L.; Liu K. C.; Jiang, S. P. Nat. Prod. Bioprospect.2012, 2, 76-80.
[7] Qi S. H.; Chen L.; Wu D. G.; Ma Y. B.; Luo X. D.Tetrahedron 2003, 59, 4193-4199.
[8] Ge Y. H.; Zhang J. X.; Mu S. Z.; Chen Y.; Yan F. M.; Lu Y.; Hao X. J. Tetrahedron2012, 68, 566-572.
[9] Yan Y.; Zhang J. X.; Huang T.; Mao X. Y.; Gu W.; He H. P.; Di Y. T.; Li S. L.; Chen D. Z.; Zhang Y.; Hao, X. J. J. Nat. Prod.2015, 78, 811-821.
[10] Zhang H. P.; Bao G. H.; Wang H. B.; Qin, G. W. Nat. Prod. Res.2004, 18, 415-419.
[11] Yan Y.; Tang L.; Hu J.; Wang J.; Adelakun T.A.; Yang D.; Di Y.; Zhang Y.; Hao, X. Pestic. Biochem. Physiol.2018, 146, 13-18.
[12] Lin B. D.; Chen H. D.; Lin J.; Zhang S.; Wu Y.; Dong L.; Yue J. M. Phytochemistry,2010, 71, 1596-1601.
[13] Yang X. R.; Tanaka N.; Tsuji D.; Lu F. L.; Yan X. J.; Itoh K.; Li D. P.; Kashiwada Y. Tetrahedron2019, 75, 130779.
[14] Liu P. Y.; Wei Y. L.; Song J. R.; Yan X. J.; Lu F. L.; Cheng Y. Y.; Yang X. R.; Li, D. P. Chin. J. Org. Chem.2024, 44, 1348-1356 (in Chinese).
(刘培源,韦玉璐,宋静茹,严小捷,卢凤来,陈月圆,羊学荣,李典鹏.有机化学, 2024, 44, 1348-1356.)
[15] Yang X. R.; Liu P. Y.; Wei Y. L.; Song J. R.; Yan X. J.; Jiang X. H.; Li J. X.; Li X. Q.; Li D. P.; Lu F. L. Molecules2023, 28, 6839.
[16] Li J.H.; Li Y.; An F.L.; Zhou, M.M. Luo J.; Jian K.L.; Luo J.; Kong L.Y. Tetrahedron2016, 72, 7481-7487.
[17] Sybyl Software, version X 2.0; Tripos Associates Inc.: St. Louis, MO, 2013.
[18] Neese, F. The ORCA program system, Wiley Interdiscip. Rev.: Comput. Mol. Sci.2012, 2, 73-78.
[19] Stephens P. J.; Harada N. ECD cotton effect approximated by the Gaussian curve and other methods. Chirality2010, 22, 229-233.

矮陀陀中一个新的prieurianin型柠檬苦素类化合物

A Novel Prieurianin-Type Limonoid from Munronia pinnata

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