Diketopiperazines and Sesquilignans from the Branches and Leaves of Claoxylon polot

Abstract

Six new diketopiperazines (1–6), two new sesquilignans (7–8), and ten known compounds (9–18) were isolated from the branches and leaves of Claoxylon polot. Their structures were elucidated by extensive spectroscopic analysis. The absolute configurations of 1–3 were assigned by computational methods. Compounds 1 and 2 exhibited antiviral activity against Coxsackie B3 virus with IC₅₀ values of 14.6 and 25.9 µM, respectively.

Key words

Claoxylon polot - Euphorbiaceae - diketopiperazines - sesquilignans - anti-Coxsackie B virus

• References

• 1 Editorial Committee of Flora of China. Flora Reipublicae Popularis Sinicae, Vol. 44 (in Chinese). Beijing: Science Press; 1996: 78
• 2 China Pharmacopoeia Committee. Chinese Pharmacopoeia (I) (in Chinese). Beijing: Hua Xue Gong Ye Press; 1977: 225
• 3 Chen JS, Zheng S. China poisonous plants (in Chinese). Beijing: Science Press; 1987: 245
• 4 Gu HS, Ma SG, Li YH, Wan YD, Liu YB, Li L, Li Y, Qu J, Lv HN, Chen XG, Jiang JD, Yu SS. Claoxylones A–I, prenylbisabolane diterpenoids with anti-Coxsackie B virus activity from the branches and leaves of Claoxylon polot . Tetrahedron 2014; 70: 7476-7483
• 5 Jin S, Wessig P, Liebscher J. Intermolecular and intramolecular Diels-Alder cycloadditions of 3-ylidenepiperazine-2,5-diones and 5-acyloxy-2(1 h)-pyrazinones. J Org Chem 2001; 66: 3984-3997
• 6 Wu XF, Hu YC, Yu SS, Jiang N, Ma J, Tan RX, Li Y, Lv HN, Liu J, Ma SG. Lysidicins F–H, three new phloroglucinols from Lysidice rhodostegia . Org Lett 2010; 12: 2390-2393
• 7 Madeline A, Andrea RR, Phillip C. New and known diketopiperazines from the Caribbean sponge, Calyx cf. Podatypa . J Nat Prod 1995; 58: 201-208
• 8 Siwicka A, Wojtasiewicz K, Rosiek B, Leniewiski A, Maurin JK, Czarnocki Z. Diastereodivergent synthesis of 2,5-diketopiperazine derivatives of β-carboline and isoquinoline from L-amino acids. Tetrahedron: Asymmetry 2005; 16: 975-993
• 9 Poisel H, Schmidt U. Asymmetrische Synthese aromatischer α-Aminosauren und N-Methyl-α-Aminosäuren. – Synthese von L-Dopa. – Über die katalytische Hydrierung ungesättigter Cyclodipeptide. Chem Ber 1973; 106: 3408-3420
• 10 Cao Y, Yu LL, Peng CS, Li ZY, Guo YW. Diketopiperazines from two strains of South China Sea sponge-associated microorganisms. Biochem Syst Ecol 2010; 38: 931-934
• 11 Park YC, Gunasekera SP, Lopez JV, Mccarthy PJ, Wright AE. Metabolites from the marine-derived fungus Chromocleista sp. isolated from a deep-water sediment sample collected in the Gulf of Mexico. J Nat Prod 2006; 69: 580-584
• 12 Campbell J, Lin Q, Geske GD, Blackwell HE. New and unexpected insights into the modulation of LuxR-type quorum sensing by cyclic dipeptides. ACS Chem Biol 2009; 4: 1051-1059
• 13 Ma ZJ, Zhang XY, Cheng L, Zhang P. Three lignans and one coumarinolignoid with quinone reductase activity from Eurycorymbus cavaleriei . Fitoterapia 2009; 80: 320-326
• 14 Houghton PJ. Lignans and neolignans from Buddleja davidii . Phytochemistry 1985; 24: 819-826
• 15 Xiong L, Zhu CG, Li YR, Tian Y, Lin S, Yuan SP, Hu JF, Hou Q, Chen NH, Yang YC, Shi JG. Lignans and neolignans from Sinocalamus affinis and their absolute configurations. J Nat Prod 2011; 74: 1188-1200
• 16 Lin S, Wang SJ, Liu MT, Gan ML, Li S, Yang YC, Wang YH, He WY, Shi JG. Glycosides from the stem bark of Fraxinus sieboldiana . J Nat Prod 2007; 70: 817-823
• 17 Liao SG, Wu Y, Yue JM. Alkaloids from Daphniphyllum longeracemosum . Helv Chim Acta 2006; 89: 73-80
• 18 Gan ML, Zhang YL, Lin S, Liu MT, Song WX, Zi JC, Yang YC, Fan XN, Shi JG, Hu JF, Sun JD, Chen NH. Glycosides from the root of Iodes cirrhosa . J Nat Prod 2008; 71: 647-654
• 19 Faouzi F, Vazquez V, Sanchez JL, Riguera R. dd-diketopiperazines: antibiotics active against Vibrio anguillarum isolated from marine bacteria associated with cultures of Pecten maximus . J Nat Prod 2003; 66: 1299-1301
• 20 Li C, Gu QQ. Study on the Antitumor Metabolites of a Sponge-Derived Fungus, Aspergillus repens . Periodical of Ocean University of China 2010; 40: 69-71