Isolation and Synthesis of Melodamide A, a New Anti-inflammatory Phenolic Amide from the Leaves of Melodorum fruticosum

Hsiu-Hui Chan; Tsong-Long Hwang; Tran Dinh Thang; Yann-Lii Leu; Ping-Chung Kuo; Bui Thi Minh Nguyet; Do Ngoc Dai; Tian-Shung Wu

doi:10.1055/s-0032-1328131

Planta Medica, Table of Contents

Planta Med 2013; 79(03/04): 288-294
DOI: 10.1055/s-0032-1328131

Natural Product Chemistry

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Isolation and Synthesis of Melodamide A, a New Anti-inflammatory Phenolic Amide from the Leaves of Melodorum fruticosum

Hsiu-Hui Chan^*

¹Department of Pharmacy, China Medical University, Taichung, Taiwan

,

Tsong-Long Hwang^*

²Graduate Institute of Natural Products, Chang Gung University, Taoyuan, Taiwan

³Chinese Herbal Medicine Research Team, Healthy Aging Research Center, Chang Gung University, Taoyuan, Taiwan

,

Tran Dinh Thang^*

⁴Department of Chemistry, Vinh University, Vinh City, Nghean Province, Vietnam

,

Yann-Lii Leu

²Graduate Institute of Natural Products, Chang Gung University, Taoyuan, Taiwan

³Chinese Herbal Medicine Research Team, Healthy Aging Research Center, Chang Gung University, Taoyuan, Taiwan

,

Ping-Chung Kuo

⁵Department of Biotechnology, National Formosa University, Yunlin, Taiwan

,

Bui Thi Minh Nguyet

⁴Department of Chemistry, Vinh University, Vinh City, Nghean Province, Vietnam

,

Do Ngoc Dai

⁶Institute of Ecology and Biological Resources, Vietnam Academy of Science and Technology, Hanoi, Vietnam

,

Tian-Shung Wu

⁷Department of Chemistry, National Cheng Kung University, Tainan, Taiwan

› Author Affiliations

Abstract

Together with twelve known compounds (2–13), melodamide A (1), a new phenolic amide possessing p-quinol moiety, was purified and characterized from the methanolic extracts of the leaves of Melodorum fruticosum. The structure of melodamide A (1) was established with a combination of 2D NMR experiments, HR-ESI-MS and X-ray analyses. The other known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. Moreover, some isolated compounds were examined for their inhibitory activity towards superoxide anion generation and elastase release in human neutrophils. Among the tested compounds, 1, 3, and 5 exhibited strong inhibition of superoxide anion generation with IC₅₀ values ranging from 5.25 to 8.65 µM. Furthermore, synthesis and biological evaluation of melodamide A (1) and its analogs (14a–p) were described.

Key words

Melodorum fruticosum - Annonaceae - melodamide A - superoxide anion generation - elastase release - anti-inflammatory

Full Text

References

References
1 Witko-Sarsat V, Rieu P, Descamps-Latscha B, Lesavre P, Halbwachs-Mecarelli L. Neutrophils: molecules, functions and pathophysiological aspects. Lab Invest 2000; 80: 617-653
2 Cowburn AS, Condliffe AM, Farahi N, Summers C, Chilvers ER. Advances in neutrophil biology-clinical implications. Chest 2008; 134: 606-612
3 Coussens LM, Werb Z. Inflammation and cancer. Nature 2002; 420: 860-867
4 Chan HH, Hwang TL, Reddy MVB, Li DT, Qian K, Bastow KF, Lee KH, Wu TS. Bioactive constituents from the roots of Panax japonicus var. major and development of a LC-MS/MS method for distinguishing between natural and artifactual compounds. J Nat Prod 2011; 74: 796-802
5 Chan HH, Hwang TL, Su CR, Reddy MVB, Wu TS. Anti-inflammatory, anticholinesterase and antioxidative constituents from the roots and the leaves of Salvia nipponica Miq. var. formosana . Phytomedicine 2011; 18: 148-150
6 Chen YF, Kuo PC, Chan HH, Kuo IJ, Lin FW, Su CR, Yang ML, Li DT, Wu TS. β-Carboline alkaloids from Stellaria dichotoma var. lanceolata and their anti-inflammatory activity. J Nat Prod 2010; 73: 1993-1998
7 Wu SJ, Leu YL, Chen CH, Chao CH, Shen DY, Chan HH, Lee EJ, Wu TS, Wang YH, Shen YC, Qian K, Bastow KF, Lee KH. Camphoratins A−J, potent cytotoxic and Anti-inflammatory triterpenoids from the fruiting body of Taiwanofungus camphoratus . J Nat Prod 2010; 73: 1756-1762
8 Pripdeevech P, Chukeatirote E. Chemical compositions, antifungal and antioxidant activities of essential oil and various extracts of Melodorum fruticosum L. flowers. Food Chem Toxicol 2010; 48: 2754-2758
9 Chaichantipyuth C, Tiyaworanan S, Mekaroonreung S, Ngamrojnavanich N, Roengsumran S, Puthong S, Petsom A, Ishikawa T. Oxidized heptenes from flowers of Melodorum fruticosum . Phytochemistry 2001; 58: 1311-1315
10 Jung JH, Pummangura S, Chaichantipyuth C, Patarapanich C, Fanwick PE, Chang CJ, McLaughlin JL. New bioactive heptenes from Melodorum fruticosum (Annonaceae). Tetrahedron 1990; 46: 5043-5054
11 Nishioka T, Watanabe J, Kawabata J, Niki R. Isolation and activity of N-p-coumaroyltyramine, an alpha-glucosidase inhibitor in Welsh onion (Allium fistulosum). Biosci Biotechnol Biochem 1997; 61: 1138-1141
12 Yu HP, Hsieh PW, Chang YJ, Chung PJ, Kuo LM, Hwang TL. 2-(2-Fluorobenzamido)benzoate ethyl ester (EFB-1) inhibits superoxide production by human neutrophils and attenuates hemorrhagic shock-induced organ dysfunction in rats. Free Radic Biol Med 2011; 50: 1737-1748
13 Hwang TL, Wang CC, Kuo YH, Huang HC, Wu YC, Kuo LM, Wu YH. The hederagenin saponin SMG-1 is a natural FMLP receptor inhibitor that suppresses human neutrophil activation. Biochem Pharmacol 2010; 80: 1190-1200
14 Gilbert C, Rollet-Labelle E, Caon AC, Naccache PH. Immunoblotting and sequential lysis protocols for the analysis of tyrosine phosphorylation-dependent signaling. J Immunol Methods 2002; 271: 185-201
15 Wu TS, Lin DM, Shi LS, Damu AG, Kuo PC, Kuo YH. Cytotoxic anthraquinones from the stems of Rubia wallichiana . Chem Pharm Bull 2003; 51: 948-950
16 Detsi A, Majdalani M, Kontogiorgis CA, Hadjipavlou-Litina D, Kefalas P. Natural and synthetic 2′-hydroxy-chalcones and aurones: Synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity. Bioorg Med Chem 2009; 17: 8073-8085
17 Hammami S, Jannet H, Bergaoui A, Ciavatta L, Cimino G, Mighri Z. Isolation and structure elucidation of a flavanone, a flavanone glycoside and vomifoliol from Echiochilon fruticosum growing in Tunisia. Molecules 2004; 9: 602-608
18 Freeman P, Murphy S, Nemorin J, Taylor W. The constituents of Australian Pimelea species. II. The isolation of unusual flavones from P. simplex and P. decora . Aust J Chem 1981; 34: 1779-1784
19 Seidel V, Bailleul F, Waterman PG. (Rel)-1β,2α-di-(2,4-dihydroxy-6-methoxybenzoyl)-3β,4α-di-(4-methoxyphenyl)-cyclobutane and other flavonoids from the aerial parts of Goniothalamus gardneri and Goniothalamus thwaitesii . Phytochemistry 2000; 55: 439-446
20 Choudhary MI, Maher S, Begum A, Abbaskhan A, Ali S, Khan A. Shafique-ur-Rehman, Atta-ur-Rahman. Characterization and antiglycation activity of phenolic constituents from Viscum album (European Mistletoe). Chem Pharm Bull 2010; 58: 980-982
21 Vasconcelos JMJ, Silva AMS, Cavaleiro JAS. Chromones and flavanones from Artemisia campestris subsp. maritima . Phytochemistry 1998; 49: 1421-1424
22 Wu TS, Chan YY. Constituents of leaves of Uncaria hirsuta Haviland. J Chin Chem Soc 1994; 41: 209-212
23 Bai N, He K, Roller M, Zheng B, Chen X, Shao Z, Peng T, Zheng Q. Active compounds from Lagerstroemia speciosa, insulin-like glucose uptake-stimulatory/inhibitory and adipocyte differentiation-inhibitory activities in 3 T3-L1 cells. J Agric Food Chem 2008; 56: 11668-11674
24 Phoebe CH, Schiff PL, Knapp JE, Slatkin DJ. Oxoanolobine, a new oxoaporphine alkaloid from Guatteria melosma . Heterocycles 1980; 14: 1977-1978
25 Piccinelli AL, Veneziano A, Passi S, Simone FD, Rastrelli L. Flavonol glycosides from whole cottonseed by-product. Food Chem 2007; 100: 344-349
26 Basnet P, Kadota S, Shimizu M, Xu HX, Namba T. 2′-Hydroxymatteucinol, a new C-methyl flavanone derivative from Matteccia orientalis – potent hypoglycemic activity in streptozotocin-Induced diabetic rat. Chem Pharm Bull 1993; 41: 1790-1795
27 Selvatici R, Falzarano S, Mollica A, Spisani S. Signal transduction pathways triggered by selective formylpeptide analogues in human neutrophils. Eur J Pharmacol 2006; 534: 1-11
28 Ushio-Fukai M, Alexander RW, Akers M, Griendling KK. p 38 Mitogen-activated protein kinase is a critical component of the redox-sensitive signaling pathways activated by angiotensin II – Role in vascular smooth muscle cell hypertrophy. J Biol Chem 1998; 273: 15022-15029

Supplementary Material

Supporting Information