Skip to main content
SpringerLink
Log in

Cedrela and Toona genera: a rich source of bioactive limonoids and triterpenoids

  • Published:
Phytochemistry Reviews Aims and scope Submit manuscript

Abstract

Cedrela P. Browne is a genus of trees, strictly related to Toona, in the Meliaceae, a family of flowering plants in the order Sapindales, which is among the most diverse sources of secondary metabolites in the Angiospermae. The most abundant metabolites in these genera are limonoids, tetranortriterpenes possessing diverse structural features, apotirucallanes, tirucallanes, and other triterpenes. The chemical constituents isolated from the genera Cedrela and Toona over the past decades, together with their biological activities, have been compiled in this article. The allelochemical and the phytotoxic activity of limonoids and triterpenoids seem to play a crucial role in the ecological function of these metabolites. While, the most promising use in human field seems related to their antimalarial and anti-inflammatory effects, even that further investigation are still needed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

Abbreviations

ABTS:

2,2′-Azino-bis(3-ethylbenzothiazoline-6-sulphonic acid)

COX:

Cyclooxygenase

ECD:

Electronic circular dichroism

DPPH:

2,2-Diphenyl-1-picrylhydrazyl

HKII:

Hexokinase II

IC50 :

Half maximal inhibitory concentration

iNOS:

Inducible nitric oxide synthase

IL:

Interleukin

LC50 :

Half maximal lethal concentration

LPS:

Lipopolysaccharide

MIC:

Minimal Inhibitory Concentration

NF-κB:

Nuclear Factor kappa-light-chain-enhancer of activated B cells

NO:

Nitric oxide

PTP1B:

Protein tyrosine phosphatase 1B

STS:

Standard target species

TNF:

Tumor Necrosis Factor

THP-1:

Human leukemia monocytic cell line

References

  • Adeoye SA, Bekoe DA (1965) The molecular structure of Cedrela odorata Substance B. Chem Commun 14:301–302

    Google Scholar 

  • Agostinho SMM, Das MF, da Silva GF, Fernandes JB et al (1994) Limonoids from Toona ciliata and speculations on their chemosystematic and ecological significance. Biochem Syst Ecol 22:323–328

    Article  CAS  Google Scholar 

  • Ambrozin ARP, Leite AC, Bueno FC et al (2006) Limonoids from Andiroba oil and Cedrela fissilis and their insecticidal activity. J Braz Chem Soc 17:542–547

    Article  CAS  Google Scholar 

  • Bevan CWL, Powell JW, Taylor DAH (1963) West African timbers. VI. Petroleum extracts from species of the genera Khaya, Guarea, Carapa, and Cedrela. J Chem Soc 0:980–982

    Article  CAS  Google Scholar 

  • Bray DH, Warhurst DC, Connolly JD et al (1990) Plants as source of antimalarial drugs. Part 7. Activity of some species of Meliaceae plants and their constituents limonoids. Phytother Res 4:29–35

    Article  CAS  Google Scholar 

  • Burke BA, Chan WR, Magnus KE et al (1969) Extractives of Cedrela odorata L.—III: The structure of photogedunin. Tetrahedron 25:5007–5011

    Article  CAS  Google Scholar 

  • Campos AM, Oliveira FS, Machado MIL et al (1991) Triterpenes from Cedrela odorata. Phytochemistry 30:1225–1229

    Article  CAS  Google Scholar 

  • Caporale LH (1995) Chemical ecology: a view from the pharmaceutical industry. Proc Natl Acad Sci USA 92:75–82

    Article  PubMed  CAS  Google Scholar 

  • Castellanos L, de Correa RS, Martinez E et al (2002) Oleanane triterpenoids from Cedrela montana (Meliaceae). Z Naturforsch C 57:575–578

    Article  PubMed  CAS  Google Scholar 

  • Castro-Gamboa I, Das MF, da Silva GF, Fo ER et al (2004) Unusual natural 9,10-dihydrophenanthrenes from roots of Toona ciliata. Arkivoc 6(iv):45–53

    Google Scholar 

  • Cavers S, Navarro C, Lowe AJ (2003) Chloroplast DNA phylogeography reveals colonization history of a Neotropical tree, Cedrela odorata L., in Mesoamerica. Mol Ecol 12:1451–1460

    Article  PubMed  CAS  Google Scholar 

  • Céspedes CL, Calderón JS, King-Diaz B et al (1998) Phytochemical and biochemical characterization of epimeric photogedunin derivatives. Their different sites of interaction on redox electron transport carrier of Spinacea oleracea L. chloroplasts. J Agric Food Chem 46:2810–2816

    Article  Google Scholar 

  • Céspedes CL, Calderon JS, Gomez-Garibay F et al (1999) Phytogrowth properties of limonoids isolated from Cedrela ciliolata. J Chem Ecol 25:2665–2676

    Article  Google Scholar 

  • Céspedes CL, Calderon GS, Lina L et al (2000) Growth inhibitory effects on fall armyworm Spodoptera frugiperda of some limonoids isolated from Cedrela spp. (Meliaceae). J Agric Food Chem 48:1903–1908

    Article  PubMed  CAS  Google Scholar 

  • Céspedes CL, Calderon JS, Salazar JR et al (2001) Plant-growth inhibitory activity of Cedrelanolide from Cedrela salvadorensis. J Chem Ecol 27:137–149

    Article  PubMed  Google Scholar 

  • Céspedes CL, Lina-Garcia LA, Kuboc IS (2016) Calceolaria integrifolia s.l. complex, reduces feeding and growth of Acanthoscelides obtectus, and Epilachna varivestis. A new source of bioactive compounds against dry bean pests. Ind Crops Prod 89:257–267

    Article  CAS  Google Scholar 

  • Chan WR, Taylor DR, Aplin RT (1966) Odoratin, an undecanortriterpenoid from Cedrela odorata. Chem Commun 16:576–577

    Google Scholar 

  • Chan WR, Magnus KE, Mootoo BS (1967a) Extractives from Cedrela odorata L. Organic, The structure of methyl angolensate J Chem Soc C, pp 171–175

    Google Scholar 

  • Chan WR, Taylor DR, Snatzke G et al (1967b) The tetracyclic triterpenes from Cedrela odorata L. Chem Commun 18:548–549

    Google Scholar 

  • Chan WR, Holder NL, Taylor DL et al (1968) Extractives of Cedrela odorata L. II. The structures of the Cedrela tetracyclic triterpenes, odoratol, isoodoratol, and odoratone. J Chem Soc C Organ 0:2485–2489

    Article  CAS  Google Scholar 

  • Chan WR, Taylor DR, Aplin RT (1972) Extracts of Cedrela odorata L.-IV: the structure of odoratin, an undecanortriterpene. Tetrahedron 28:431–437

    Article  CAS  Google Scholar 

  • Chatterjee A, Chakrabortty T, Chandrasekharan S (1971) Chemical investigation of Cedrela toona. Phytochemistry 10:2533–2535

    Article  CAS  Google Scholar 

  • Chen HD, Yang SP, Wu Y et al (2009) Terpenoids from Toona ciliata. J Nat Prod 72:685–689

    Article  PubMed  CAS  Google Scholar 

  • Chini MG, Malafronte N, Vaccaro MC et al (2016) Identification of limonol derivatives as Heat Shock Protein 90 (Hsp90) inhibitors through a multidisciplinary approach. Chem Eur J 22:13236–13250

    Article  PubMed  CAS  Google Scholar 

  • Connolly JD, Handa KL (1969) Tetranortriterpenoids and related substances. Part XII. 6-hydrocarapin and a tetracyclic triterpenoid pentaol from Cedrela glaziovii. J Chem Soc C Organ 0:2435–2436

    Article  CAS  Google Scholar 

  • Connolly JD, McCrindle R, Overton KH (1965) Constitution of mexicanolide. Novel cleavage reaction in a naturally occurring bicyclo[3.3.1]nonane derivative. Chem Commun 8:162–163

    CAS  Google Scholar 

  • Connolly JD, Handa KL, McCrindle R et al (1967) Mexicanol. Tetrahedron Lett 36:3449–3452

    Article  Google Scholar 

  • De Paula JR, Vieira IJC, Das MF, da Silva GF et al (1997) Sesquiterpenes, triterpenoids, limonoids and flavonoids of Cedrela odorata graft and speculations on the induced resistance against Hypsipyla grandella. Phytochemistry 44:1449–1454

    Article  Google Scholar 

  • Dong XJ, Zhu YF, Bao GH et al (2013) New limonoids and a dihydrobenzofuran norlignan from the roots of Toona sinensis. Molecules 18:2840–2850

    Article  PubMed  CAS  Google Scholar 

  • El-Shamy AM, El-Shabrawy AO, Selim MA, Motawe HM (1988) Fitoterapia 59:219–220

    CAS  Google Scholar 

  • Estrada-Contreras I, Equihua M, Laborde I et al (2016) Current and future distribution of the tropical tree Cedrela odorata L. in Mexico under climate change scenarios using MaxLike. PLoS ONE 11:e0164178

    Article  PubMed  PubMed Central  Google Scholar 

  • Gou HX, Ye JI, Wang YI et al (2017) The anti-inflammatory activity of toonaciliatin K against adjuvant arthritis. Biomed Res Int. https://doi.org/10.1155/2017/9436280

    Article  PubMed  PubMed Central  Google Scholar 

  • Govindachari TR, Suresh G, Gopalakrishnan GE et al (2000) Antifungal activity of some tetranortriterpenoids. Fitoterapia 71:317–320

    Article  PubMed  CAS  Google Scholar 

  • Grant IJ, Hamilton JA, Hamor TA et al (1963) The structure of cedrelone. X-ray analysis of cedrelone iodoacetate. J Chem Soc 0:2506–2515

    Article  CAS  Google Scholar 

  • Hodges R, McGeachin SG, Raphael RA (1963) Chemistry of cedrelone. J Chem Soc 0:2515–2526

    Article  CAS  Google Scholar 

  • Hu J, Song Y, Mao X et al (2016) Limonoids isolated from Toona sinensis and their radical scavenging, anti-inflammatory and cytotoxic activities. J Funct Foods 20:1–9

    Article  CAS  Google Scholar 

  • Kim YS, Alarcon SV, Lee S et al (2009) Update on Hsp90 inhibitors in clinical trial. Curr Top Med Chem 9:1479–1492

    Article  PubMed  CAS  Google Scholar 

  • Kipassa NT, Iwagawa T, Okamura H et al (2008) Limonoids from the stem bark of Cedrela odorata. Phytochemistry 69:1782–1787

    Article  PubMed  CAS  Google Scholar 

  • Koul O, Isman MB (1992) Toxicity of the limonoid alleochemical cedrelone to noctuid larvae. Entomol Exp Appl 64:281–287

    Article  CAS  Google Scholar 

  • Kraus W, Grimminger W (1980) 23-(R,S)-Hydroxytoonacilid and 21-(R,S)-hydroxytoonacilid, two new B-seco-tetranortriterpenoids with feeding inhibitor activity against insects isolated from the Toonaa ciliata M. J. Roem. var australis (Meliaceae). New J Chem 4:651–655

    CAS  Google Scholar 

  • Kraus W, Grimminger W (1981) Toonafolin, a novel tetranortriterpenoid B lactone from Toona ciliata M. J. Roem. var. australis (Meliaceae). Liebigs Ann Chem 0:1838–1843

    Article  CAS  Google Scholar 

  • Kraus W, Kypke K (1979) Surenone and surenin, two novel tetranortriterpenoids from Toona sureni [blume] Merrill. Tetrahedron Lett 20:2715–2716

    Article  Google Scholar 

  • Kraus W, Grimminger W, Sawitzki G (1978) Toonacilin and 6-acetoxytoonacilin, two novel B-seco-tetranortriterpenoids with antifeeding activity. Angew Chem Int Ed Engl 17:452–453

    Article  Google Scholar 

  • Kraus W, Kypke K, Bokel M et al (1982) Surenolactone, a novel tetranortriterpenoid A/B-dilactone from Toona sureni IBlumel Merrill (Meliaceae). Liebigs Ann Chem 0:87–98

    Article  CAS  Google Scholar 

  • Kribs D (1930) Comparative anatomy of the woods of the Meliaceae. Am J Bot 17:724–738

    Article  Google Scholar 

  • Lavie D, Levy EC, Rosito C et al (1970) Studies on tetranortriterpenoid constituents of Cedrela angustifolia Sesse & Moc. Tetrahedron 26:219–226

    Article  CAS  Google Scholar 

  • Leite AC, Bueno FC, Oliveira CG et al (2005) Limonoids from Cipadessa fruticosa and Cedrela fissilis and their insecticidal activity. J Braz Chem Soc 16:1391–1395

    Article  CAS  Google Scholar 

  • Leite AC, Ambrozin AR, Fernandes JB et al (2008) Trypanocidal activity of limonoids and triterpenes from Cedrela fissilis. Planta Med 74:1795–1799

    Article  PubMed  CAS  Google Scholar 

  • Li J-H, Li Y, An F-L et al (2016) Limonoids with modified furan rings from root barks of Toona sinensis. Tetrahedron 72:7481–7487

    Article  CAS  Google Scholar 

  • Liao SG, Yang SP, Yuan T et al (2007) Limonoids from the leaves and stems of Toona ciliata. J Nat Prod 8:1268–1273

    Article  CAS  Google Scholar 

  • Liu J, Yang SP, Su ZS et al (2011) Limonoids from the stems of Toona ciliata var. henryi (Meliaceae). Phytochemistry 72:2189–2196

    Article  PubMed  CAS  Google Scholar 

  • Liu JQ, Wang CF, Li Y et al (2012) Limonoids from the leaves of Toona ciliata var. yunnanensis. Phytochemistry 76:141–149

    Article  PubMed  CAS  Google Scholar 

  • Liu CP, Wang GC, Gan LS et al (2016) Ciliatonoids A and B, two limonoids from Toona ciliata. Org Lett 18:2894–2897

    Article  PubMed  CAS  Google Scholar 

  • Luo XD, Wu SH, Ma YB et al (2000) Limonoids and phytol derivatives from Cedrela sinensis. Fitoterapia 71:492–496

    Article  PubMed  CAS  Google Scholar 

  • Luo J, Huang W-S, Hu S-M et al (2017) Rearranged limonoids with unique 6/5/6/5 tetracarbocyclic skeletons from Toona ciliata and biomimetic structure divergence. Org Chem Front 4:2417–2421

    Article  CAS  Google Scholar 

  • Mabberley D (1997) The Plant-Book, a portable dictionary of the vascular plants. Cambridge University Press, Cambridge, p 300

    Google Scholar 

  • MacKinnon S, Durst T, Arnason JT (1997) Antimalarial activity of tropical meliaceae extracts and gedunin derivatives. J Nat Prod 60:336–341

    Article  PubMed  CAS  Google Scholar 

  • Marcelle GB, Mootoo BS (1981) 7α,11β-diacetoxydihydronomilin, a new tetranortriterpenoid from Cedrela mexicana. Tetrahedron Lett 22:505–508

    Article  CAS  Google Scholar 

  • Meng Q-Q, Peng X-R, Lu S-Y et al (2016) Lactam triterpenoids from the bark of Toona sinensis. Nat Prod Bioprospect 6:239–245

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Mitsui K, Maejima M, Fukaya H et al (2004) Limonoids from Cedrela sinensis. Phytochemistry 65:3075–3081

    Article  PubMed  CAS  Google Scholar 

  • Mitsui K, Maejima M, Saito H et al (2005) Triterpenoids from Cedrela sinensis. Tetrahedron 61:10569–10582

    Article  CAS  Google Scholar 

  • Mitsui K, Saito H, Yamamura R et al (2006) Hydroxylated gedunin derivatives from Cedrela sinensis. J Nat Prod 69:1310–1314

    Article  PubMed  CAS  Google Scholar 

  • Mitsui K, Saito H, Yamamura R et al (2007) Apotirucallane and tirucallane triterpenoids from Cedrela sinensis. Chem Pharm Bull 55:1442–1447

    Article  PubMed  CAS  Google Scholar 

  • Muellner A, Samamuel R, Johnson S et al (2003) Molecular phylogenetics of Meliaceae (Sapindales) based on nuclear and plastid DNA sequences. Am J Bot 90:471–480

    Article  PubMed  CAS  Google Scholar 

  • Muellner A, Pennington T, Koecke A et al (2010) Biogeography of Cedrela (Meliaceae, Sapindales) in Central and South America. Am J Bot 97:511–518

    Article  PubMed  Google Scholar 

  • Mulholland DA, Taylor DAH (1992) Limonoids from Australian members of the Meliaceae. Phytochemistry 31:4163–4166

    Article  CAS  Google Scholar 

  • Nebo LI, Varela ROM, Molinillo JMG et al (2015) Phytotoxicity of triterpenes and limonoids from the Rutaceae and Meliaceae. 5α,6β,8α,12α-Tetrahydro-28-norisotoonafolin—a potent phytotoxin from Toona ciliata. Nat Prod Commun 10:17–20

    PubMed  Google Scholar 

  • Neto JO, Agostinho SMM, Das MF, da Silva GF et al (1995) Limonoids from seeds of Toona ciliata and their chemosystematic significance. Phytochemistry 38:397–401

    Article  Google Scholar 

  • Neto JO, Das MF, da Silva GF, Fo EF et al (1998) Norlimonoids from seeds of Toona ciliata. Phytochemistry 49:1369–1373

    Article  Google Scholar 

  • Newton C, Baker P, Ramnarine S et al (1993) The Mahogany shoot borer: prospects for control. For Ecol Manag 57:301–328

    Article  Google Scholar 

  • Newton AC, Allnutt TR, Gillies ACM et al (1999) Molecular phylogeography, intraspecific variation and the conservation of tree species. Trends Evol Ecol 14:140–145

    Article  CAS  Google Scholar 

  • Ning J, He HP, Li SF et al (2010) Triterpenoids from the leaves of Toona ciliata. J Asian Nat Prod Res 12:448–452

    Article  PubMed  CAS  Google Scholar 

  • Okorie DA, Taylor DAH (1968) Extractives from the seed of Cedrela odorata L. Phytochemistry 7:1683–1686

    Article  CAS  Google Scholar 

  • Omar S, Zhang J, MacKinnon S et al (2003) Traditionally-used antimalarials from the Meliaceae. Curr Top Med Chem 3:137–139

    Article  Google Scholar 

  • Parihar DB, Dutt S (1950) Chemical examination of the wood of Cedrela toona. Isolation of a lactone, an essential oil, and a coloring matter. J Ind Chem Soc 27:77–80

    CAS  Google Scholar 

  • Pennington TD, Styles BT (1975) A generic monograph of the Meliaceae. Blumea 22:419–540

    Google Scholar 

  • Pennington T, Styles B, Taylor D (1981) Meliaceae. Monograph No. 28. Flora Neotropica. The New York Botanical Garden, New York, p 470

    Google Scholar 

  • Pérez-Flores JU, Eigenbrode D, Hilje-Quiroz LU (2012) Alkaloids, limonoids and phenols from Meliaceae species decrease survival and performance of Hypsipyla grandella Larvae. Am J Plant Sci 3:988–994

    Article  CAS  Google Scholar 

  • Rashed K (2014) Antioxidant potential of Cedrela odorata stems extracts and bioactive phytoconstituents. Hygeia J D Med 6:25–30

    Article  CAS  Google Scholar 

  • Russo D, Bonomo MG, Salzano G et al (2012) Nutraceutical properties of Citrus clementina juices. Pharmacologyonline 1:84–93

  • Russo D, Valentão P, Andrade PB et al (2015) Evaluation of antioxidant, antidiabetic and anticholinesterase activities of Smallanthus sonchifolius landraces and correlation with their phytochemical profiles. Int J Mol Sci 16:17696–17718

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Saltos MBV, Puente BFN, Faraone I et al (2015) Inhibitors of α-amylase and α-glucosidase from Andromachia igniaria Humb. & Bonpl. Phytochem Lett 14:45–50

  • Sanni SB, Behm H, Beurskens PT (1987) Structure and absolute configuration of Cedrela odorata substance B (mexicanolide). Acta Cryst C43:1400–1403

    CAS  Google Scholar 

  • Segura R, Calderón J, Toscano R et al (1994) Cedrelanolide I. A new limonoid from Cedrela salvadorensis. Tetrahedron Lett 35:3437–3440

    Article  CAS  Google Scholar 

  • Tan Q-G, Luo X-D (2011) Meliaceous limonoids: chemistry and biological activities. Chem Rev 111:7437–7522

    Article  PubMed  CAS  Google Scholar 

  • Tang J, Xu J, Zhang J et al (2016) Novel tirucallane triterpenoids from the stem bark of Toona sinensis. Fitoterapia 112:97–103

    Article  PubMed  CAS  Google Scholar 

  • Toscano RA, Mata R, Calderon J et al (1996) Gedunin, a D-seco limonoid. J Chem Crystalllogr 26:707–711

    Article  CAS  Google Scholar 

  • Veitch NC, Wright GA, Stevenson PC (1999) Four new tetranortriterpenoids from Cedrela odorata associated with leaf rejection by Exopthalmus jekelianus. J Nat Prod 62:1260–1263

    Article  PubMed  CAS  Google Scholar 

  • Wang J-R, Liu H-I, Kurtán T et al (2011) Org Biomol Chem 9:7685–7696

    Article  PubMed  CAS  Google Scholar 

  • Wright GEA, Simpson STJ, Raubenheimer DA et al (2003) The feeding behavior of the weevil, Exophthalmus jekelianus, with respect to the nutrients and allelochemicals in host plant leaves. Oikos 100:172–184

    Article  CAS  Google Scholar 

  • Wu WE, Zhang HU, Dong SH et al (2014) New triterpenoids with protein tyrosine phosphatase 1B inhibition from Cedrela odorata. J Asian Nat Prod Res 16:709–716

    Article  PubMed  CAS  Google Scholar 

  • Xia J-J, Li X-Y, Zhang S-Z et al (2014) An unusual 9,11-seco limonoid from Toona ciliata. Tetrahedron Lett 55:2104–2106

    Article  CAS  Google Scholar 

  • Yang M-S, Hu S-M, Kong L-Y et al (2015) B-seco-29-nor-limonoids from the stem barks of Toona ciliata var. yunnanensis. Tetrahedron 71:8472–8477

    Article  CAS  Google Scholar 

  • Zelnik R, Rosito CM (1966) Fissinolide. Tetrahedron Lett 52:6441–6444

    Article  PubMed  CAS  Google Scholar 

  • Zhang F, Liao SG, Zhang CR et al (2011) Limonoids and diterpenoids from Toona ciliata Roem. var. yunnanensis. Planta Med 77:1617–1622

    Article  PubMed  CAS  Google Scholar 

  • Zhang F, Wang J-S, Gu Y-C et al (2012) Cytotoxic and anti-inflammatory triterpenoids from Toona ciliata. J Nat Prod 75:538–546

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Dipartimento di Farmacia, Università di Pisa, Via Bonanno 33, 56126, Pisa, Italy

    Marinella De Leo & Alessandra Braca

  2. Dipartimento di Scienze, Università degli Studi della Basilicata, Viale dell’Ateneo Lucano 10, 85100, Potenza, Italy

    Luigi Milella

  3. Dipartimento di Farmacia, Università di Salerno, Via Giovanni Paolo II, 84084, Fisciano, SA, Italy

    Nunziatina De Tommasi

Authors
  1. Marinella De Leo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Luigi Milella
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Alessandra Braca
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Nunziatina De Tommasi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Luigi Milella.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

De Leo, M., Milella, L., Braca, A. et al. Cedrela and Toona genera: a rich source of bioactive limonoids and triterpenoids. Phytochem Rev 17, 751–783 (2018). https://doi.org/10.1007/s11101-018-9557-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11101-018-9557-1

Keywords

Search

Navigation