Tetranortriterpenes and Limonoids from the Roots of Aphanamixis polystachya

Ching-Jie Lin; I-Wen Lo; Yu-Chi Lin; Shun-Ying Chen; Ching-Te Chien; Yao-Haur Kuo; Tsong-Long Hwang; Shorong-Shii Liou; Ya-Ching Shen

doi:10.3390/molecules21091167

Tetranortriterpenes and Limonoids from the Roots of Aphanamixis polystachya

Molecules. 2016 Sep 2;21(9):1167. doi: 10.3390/molecules21091167.

Authors

Ching-Jie Lin¹, I-Wen Lo², Yu-Chi Lin³, Shun-Ying Chen⁴, Ching-Te Chien⁵, Yao-Haur Kuo⁶, Tsong-Long Hwang^{7

8}, Shorong-Shii Liou⁹, Ya-Ching Shen¹⁰

Affiliations

¹ School of Pharmacy, College of Medicine, National Taiwan University, No. 33, Linsen S. Rd., Zhongzheng Dist., Taipei 10050, Taiwan. r00423014@ntu.edu.tw.
² School of Pharmacy, College of Medicine, National Taiwan University, No. 33, Linsen S. Rd., Zhongzheng Dist., Taipei 10050, Taiwan. d96423006@ntu.edu.tw.
³ Department of Life Sciences, National Cheng Kung University, No. 1, University Road, Tainan 701, Taiwan. z10108042@email.ncku.edu.tw.
⁴ Taiwan Forestry Research Institute, Council of Agriculture, Executive Yuan, No. 53, Nanhai Rd., Zhongzheng Dist., Taipei 10066, Taiwan. sychen@tfri.gov.tw.
⁵ Taiwan Forestry Research Institute, Council of Agriculture, Executive Yuan, No. 53, Nanhai Rd., Zhongzheng Dist., Taipei 10066, Taiwan. chien@tfri.gov.tw.
⁶ National Research Institute of Chinese Medicine, Ministry of Health and Welfare, No. 155-1, Sec. 2, Linong St., Beitou District, Taipei 11221, Taiwan. kuoyh@nricm.edu.tw.
⁷ Graduate Institute of Natural Products, School of Traditional Medicine, College of Medicine, and Chinese Herbal Medicine Research Team, Healthy Aging Research Center, Chang Gung University, Taoyuan 33302, Taiwan. htl@mail.cgu.edu.tw.
⁸ Department of Cosmetic Science and Research Center for Industry of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 33302, Taiwan. htl@mail.cgu.edu.tw.
⁹ Department of Pharmacy, Tajen University, No. 20, Weixin Rd., Yanpu Township, Pingtung 90741, Taiwan. ssliou@tajen.edu.tw.
¹⁰ School of Pharmacy, College of Medicine, National Taiwan University, No. 33, Linsen S. Rd., Zhongzheng Dist., Taipei 10050, Taiwan. ycshen@ntu.edu.tw.

Abstract

Phytochemical investigation of the acetone extract from the roots of Aphanamixis polystachya resulted in isolation of four new tetranortriterpenes (1-4) in addition to one protolimonoid (methyl-1ξ,7R-diacetoxy-23R,25-dihydroxy-20S,24R-21,24-epoxy-3,4-seco-apotirucall-4(28),14(15)-diene-3-oate (5)), five known limonoids (rohituka 3 (6), rohituka 7 (7), nymania 1 (8), rubrin G (9), prieurianin (10)) and a steroid (2,3-dihydroxy-5-pregnan-16-one (11)). Their structures were determined by spectroscopic analyses, including 2D-NMR (COSY, HMQC, HMBC, and NOESY) and high-resolution electrospray ionization mass spectrometry (HRESIMS). Cytotoxic and anti-inflammatory activities of these compounds were evaluated. Compounds 4 and 5 showed significant inhibition against superoxide generation and elastase release by human neutrophils in response to (formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B) (FMLP/CB).

Keywords: Aphanamixis polystachya; anti-inflammatory activity; apotirucallane-type triterpenoid; cytotoxicity; limonoid.

MeSH terms

Humans
Leukocyte Elastase / metabolism*
Limonins* / chemistry
Limonins* / isolation & purification
Limonins* / pharmacology
Meliaceae / chemistry*
Neutrophils / cytology
Neutrophils / metabolism*
Plant Extracts / chemistry*
Plant Roots / chemistry*
Superoxides / metabolism*

Substances

Limonins
Plant Extracts
Superoxides
Leukocyte Elastase