Diterpenoids from Casearia sylvestris

Abstract

Two highly oxygenated clerodane diterpenes casearins U (1) and V (2) and two ent-kaurane diterpene glucosides sylvestrisides A (3) and B (4) were isolated from the leaves of Casearia sylvestris, together with 13 known compounds. Their structures were established on the basis of 1D and 2D NMR spectroscopic analyses and comparison with literature data.

Key words

Casearia sylvestris - Flacourtiaceae - clerodane diterpenes - ent‐kaurane diterpene glucosides - casearins U and V - sylvestrisides A and B

References

• 1 Lorenzi H, Matos F JA. Plantas medicinais no Brasil: nativas e exóticas. São Paulo; Instituto Plantarum 2002: 220-221
• 2 Tobias M L, Oliveira F, de Oliveira K P, Marques L C. Quality control of vegetable drugs of the manipulation drugstores of Maringa (Parana Brazil).  Rev Eletronica Farm. 2007;  4 95-103
• 3 Cruz G L. Dicionario das plantas Uteisudo Brasil, 5th edition. Rio de Janeiro; Bertrand 1995: 599-600
• 4 Oshima-Franco Y, Alves C MV, Andréo Filho N, Gerenutti M, Cintra A CO, Leite G B, Rodrigues-Simioni L, Silva M G. Neutralization of the neuromuscular activity of bothropstoxin-1, A myotoxin from Bothrops jararacussu snake venom, by a hydroalcoholic extract of Caseria sylvestris SW (Guaçatonga).  J Venom Anim Toxins Trop Dis. 2005;  11 465-478
• 5 Borges M H, Soares A M, Rodrigues V M, Oliveira F, Franscheschi A M, Rucavado A, Gigliob J R, Homsi-Brandeburgo M I. Neutralization of protease from Bothrops snake venoms by the queous extract from Casearia sylvestris (Flacourtiaceae).  Toxicon. 2001;  39 1863-1869
• 6 Ruppett B M, Pereira E F, Gonçalves L C, Pereira N A. Pharmacological screening of plants recommended by folk medicine as anti-snake venom – I. Analgesic and anti-inflammatory activities.  Mem Inst Oswaldo Cruz. 1991;  87 203-205
• 7 Sertié J AA, Carvalho J CT, Panizza S. Antiulcer activity of crude extract from the leaves of Casearia sylvestris. .  Pharm Biol. 2000;  38 112-119
• 8 Fabrício G S, Naira F ZS, Caroline E M, Neusa F M, Rosiane B ND. Clastogenic and anticlastogenic effect of the essential oil from Casearia sylvestris Swart.  J Essent Oil Res. 2007;  19 367-369
• 9 Itokawa H, Totsuka N, Takeya K, Watanabe K, Obala E. Antitumor principles from Casearia sylvestris Sw. (Flacourtiaceae), structure elucidation of new clerodane diterpenes by 2-D NMR spectroscopy.  Chem Pharm Bull. 1988;  36 1585-1588
• 10 Itokawa H, Totsuka N, Morita H, Takeya K, Iitaka Y, Schenkel E P, Motidome M. New antitumor principles, casearins A–F, for Casearia sylvestris Sw. (Flacourtiaceae).  Chem Pharm Bull. 1990;  38 3384-3388
• 11 Morita H, Nakayama M, Kojima H, Takeya K, Itokawa H, Schenkel E P, Motidome M. Structures and cytotoxic activity relationship of casearins, new clerodane diterpenes from Casearia sylvestris Sw.  Chem Pharm Bull. 1991;  39 693-697
• 12 de Carvalho P RF, Furlan M, Young M CM, Kingston D GI, da Bolzani S .V. Acetylated DNA-damaging clerodane diterpene from Casearia sylvestris.  Phytochemistry. 1998;  48 1659-1662
• 13 Oberlies N H, Burgess J P, Navarro H A, Pinos R E, Fairchild C R, Peterson R W, Soejarto D D, Farnsworth N R, Kinghorn A D, Wani M C, Wall M E. Novel bioactive clerodane diterpenoids from the leaves and twigs of Casearia sylvestris.  J Nat Prod. 2002;  65 95-99
• 14 Espindola L S, Júnior J RV, de Mesquita M L, Marquié P, de Paula J E, Mambu L, Santana J M. Trypanocidal activity of a new diterpene from casearia sylvestris var. lingua.  Planta Med. 2004;  70 1093-1095
• 15 dos Santos A G, Perez C C, Tininis A G, da Silva Bolzani V, Cavalheiro A J. Clerodane diterpenes from leaves of Casearia sylvestris SWARTZ.  Quim Nova. 2007;  30 1100-1103
• 16 Rivera A P, Fainl F, Castillo M. 15α-Hydroxy-β-amyrin and patagonic acid from Baccharis magellanica and Baccharis patagonica.  J Nat Prod. 1988;  51 155-157
• 17 Gonzalez A G, Fraga B M, Hernandez M G, Hanson J R. The ¹³C NMR spectra of some ent-18-hydroxykaur-16-enes.  Phytochemistry. 1981;  20 846-847
• 18 Fuyihiko I, Akira A. Analysis of ¹H and ¹³C nuclear magnetic resonance spectra of spathulenol by two-dimensional methods.  J Chem Soc [Perkin II]. 1985;  1773-1778
• 19 Figliuolo R, Naylor S, Wang J, Langenheim J H. Unusual nonprotein imino acid and its relationship to phenolic and nitrogenous compounds in Copaifera.  Phytochemistry. 1987;  26 3255-3259
• 20 Miyazawa M, Okuno Y, Nakamura S, Kameoka H. Suppression of SOS- inducing activity of chemical mutagens by cinnamic acid derivatives from Scrophularia ningpoensis in the Salmonella typhimurium TA1535/pSK1002 umu test.  J Agric Food Chem. 1998;  46 904-910
• 21 Voutquenne L, Lavaud C, Massiot G, Sevenet T, Hadi H A. Cytotoxic polyisoprenes and glycosides of long-chain fatty alcohols from Dimocarpus fumatus.  Phytochemistry. 1999;  50 63-69
• 22 Gassmann J, Strell I, Brandl F, Sturm M, Hoppe W. Structure determination of methylpheophorbide A.  Tetrahedron Lett. 1971;  48 4609-4612
• 23 Lötjönen S, Hynninen P H. Complete assignment of the carbon-13 NMR spectrum of chlorophyl a.  Org Magn Reson. 1981;  16 304-308
• 24 Lötjönen S, Michalski T J, Norris J R, Hynninen P H. High-field proton NMR study of the liquid solution structure of monomeric bacteriochlorophyll a and chlorophyll a.  Magn Reson Chem. 2005;  25 670-674
• 25 Mao S, Sang S, Lao A, Chen Z. Steroid constituents from Euonymus mupinensis.  Tianran Chanwu Yanjiu Yu Kaifa. 2000;  12 14-16
• 26 Mustafa J, Khan S I, Ma G, Walker L A, Khan I A. Synthesis and anticancer activities of fatty acid analogs of podophyllotoxin.  Lipids. 2004;  39 167-172
• 27 Kanokmedhakul S, Kanokmedhakul K, Buayairaksa M. Cytotoxic clerodane diterpenoids from fruits of Casearia grewiifolia.  J Nat Prod. 2007;  70 1122-1126
• 28 Sang S, Li G, Tian S, Lapsley K, Stark R E, Pandey R K, Rosen R T, Ho C. An unusual diterpene glycoside from the nuts of almond (Prunus amygdalus Batsch).  Tetrahedron Lett. 2003;  44 1199-1202
• 29 Li X, Zhang D, Onda M, Konda Y, Iguchi M, Harigaya Y. Ent-kauranoid diterpenes from Artemisia sacrorum.  J Nat Prod. 1990;  53 657-661
• 30 Cheenpracha S, Yodsaoue O, Karalai C, Ponglimanont C, Subhadhirasakul S, Tewtrakul S, Kanjana-opas A. Potential anti-allergic ent-kaurene diterpenes from the bark of Suregada multiflora.  Phytochemistry. 2006;  67 2630-2634
• 31 Jia Z, Shi J, Yang L. Ent-kaurane diterpenoids from Euphorbia wangii.  J Nat Prod. 1994;  57 811-816