Abstract
This study aims to analyze the ethnobotanical, chemical, and biological activities of triterpenoid compounds isolated from the Dysoxylum genus of the Meliaceae family between 1974 and 2021. The species are mainly distributed in Africa, Asia, and Australia, and used as a traditional medicine to treat various diseases. Triterpenoid was first isolated in 1976 and as tetranortriterpenoid or limonoid, it was named dysobinin. Several studies were conducted for more than 40 years on the plants’ stems, bark, and leaves, where approximately 279 triterpenoid compounds from several groups such as dammarane, nortriterpenoid, oleanane, lupane, tirucallane, cyclolanostane, or cycloartane, glabretal, and cycloapoeuphane-types were isolated with some synthetic products. In addition, the hypothetical route of triterpenes biosynthesis from this genus was identified, and tirucallane-type were reported to be 37.6% of the total compounds. The anti-malarial, anti-feedant, antimicrobial, anti-inflammatory, antioxidant, vasodilative effect, anti-viral, cortisone reductase, and cytotoxic activities of the extract were also evaluated. The results showed the necessity of using the triterpenoid compounds from the Dysoxylum genus in traditional medicine and the discovery of new drugs.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Aalbersberg W, Singh Y (1991) Dammarane triterpenoids from Dysoxylum richii. Phytochemistry 30:921–926. https://doi.org/10.1016/0031-9422(91)85280-D
Adesanya SA, Pais M, Sevenet T (1991) Apotirucallane triterpenes from Dysoxylum roseum. J Nat Prod 54:1588–1594. https://doi.org/10.1021/np50078a015
Aladesanmi AJ, Ilesanmi OR (1987) Phytochemical and pharmacological investigation of the cardioactive constituents of the leaf of Dysoxylum lenticellare. J Nat Prod 50:1041–1044. https://doi.org/10.1021/np50054a004
Barbhuiya AR, Sharma GD, Arunachalam A, Deb S (2009) Diversity and conservation of medicinal plants in Barak valley, Northeast India. Indian J Tradit Knowl 8: 169–175. http://nopr.niscair.res.in/handle/123456789/3958
Bourdy G, Walter A (1992) Maternity and medicinal plants in Vanuatu I. The cycle of reproduction. J Ethnopharmacol 37:179–196. https://doi.org/10.1016/0378-8741(92)90033-N
Bourdy G, Francois C, Andary C, Boucard M (1996) Maternity and medicinal plants in Vanuatu II. Pharmacological screening of five selected species. J Ethnopharmacol 52:139–143. https://doi.org/10.1016/0378-8741(96)01404-3
Cao P, Liang G, Gao X, Wang X, Li Z (2013) Three new nor-dammarane triterpenoids from Dysoxylum hainanense with particular cytotoxicity against glioma cell line. Arch Pharm Res 36:322–326. https://doi.org/10.1007/s12272-013-0030-9
Chanda R, Mohanty JP, Bhuyan NR, Kar PK, Nath LK (2007) Medicinal pants used against gastrointestinal tract disorders by the traditional healers of Sikkim Himalayas. Indian J Tradit Knowl 8: 606–610. http://nopr.niscair.res.in/handle/123456789/1012
Chen JL, Kernan MR, Jolad SD, Stoddart CA, Bogan M, Cooper R (2007) Dysoxylines A–D, tetranortriterpenoids with potent anti-RSV activity from Dysoxylum gaudichaudianum. J Nat Prod 70:312–315. https://doi.org/10.1021/np060398y
Chen XQ, Chen LX, Zhao J, Tang YP, Li SP (2017) Nortriterpenoids from the fruiting bodies of the mushroom Ganoderma resinaceum. Molecules 22:1073. https://doi.org/10.3390/molecules22071073
Dharmayani NKT, Yoshimura T, Hermawati E, Juliawaty LD, Syah YM (2020) Antibacterial and antifungal two phenolic sesquiterpenes from Dysoxylum densiflorum. Z Naturforsch C 75:1–5. https://doi.org/10.1515/znc-2019-0072
Duh CY, Wang SK, Chen IS (2000) Cytotoxic prenyleudesmane diterpenes from the fruits of Dysoxylum kuskusense. J Nat Prod 63:1546–1547. https://doi.org/10.1021/np000264z
Fujioka T, Sakurai A, Mihashi K, Kashiwada Y, Chen IS, Lee KH (1997a) Antitumor agents. 168. Dysoxylum cumingianum IV. The structures of Cumingianosides G–O, new triterpene glucosides with a 14,18-cycloapotirucallane-type skeleton from Dysoxylum cumingianum, and their cytotoxicity against human cancer cell lines. Chem Pharm Bull 45:68–74. https://doi.org/10.1248/cpb.45.68
Fujioka T, Sakurai A, Mihashi K, Kashiwada Y, Chen IS, Lee KH (1997b) Antitumor agents. 169. Dysoxylum cumingianum V. Cumingianosides P and Q, new cytotoxic triterpene glucosides with an apotirucallane-type skeleton from Dysoxylum cumingianum. Chem Pharm Bull 45:202–206. https://doi.org/10.1248/cpb.45.202
Fujioka T, Yamamoto M, Kashiwada Y, Fujii H, Mihashi K, Ikeshiro Y, Chen IS, Lee KH (1998) Novel cytotoxic diterpenes from the stem of Dysoxylum kuskusense. Bioorg Med Chem Lett 8:3479–3482. https://doi.org/10.1016/S0960-894X(98)00630-1
Govindachari TR, Suresh G, Kumari GNK (1994) Triterpenoids from Dysoxylum malabaricum. Phytochemistry 37:1127–1129. https://doi.org/10.1016/S0031-9422(00)00413-1
Govindachari TR, Suresh G, Kumari GNK, Rajamannar T (1999) Nymania-3: a bioactive triterpenoid from Dysoxylum malabaricum. Fitoterapia 70:83–86. https://doi.org/10.1016/S0367-326X%2898%2900036-7
Gu J, Cheng GG, Qian SY, Li Y, Liu YP, Luo XD (2014) Dysoxydensins A–G, seven new clerodane diterpenoids from Dysoxylum densiflorum. Plant Med 80:1017–1022. https://doi.org/10.1055/s-0034-1382903/
Han ML, Zhao JX, Liu HC, Ni G, Ding J, Yang SP, Yue JM (2015) Limonoids and triterpenoids from Dysoxylum mollissimum var. glaberrimum. J Nat Prod 78:754–761. https://doi.org/10.1021/np500967k
He XF, Wang XN, Gan LS, Yin S, Dong L, Yue JM (2008) Two novel triterpenoids from Dysoxylum hainanense. Org Lett 10:4327–4330. https://doi.org/10.1021/ol801834y
He XF, Wang XN, Yin S, Dong L, Yue JM (2009) Ring A modified novel triterpenoids from Dysoxylum hainanense. Eur J Org Chem. https://doi.org/10.1002/ejoc.200900609
He XF, Wang XN, Yin S, Dong L, Yue JM (2011) Ring A-seco triterpenoids with antibacterial activity from Dysoxylum hainanense. Bioorg Med Chem Lett 21:125–129. https://doi.org/10.1016/j.bmcl.2010.11.057/
Heyne K (1982) The useful Indonesian plants. Research and Development Agency, Ministry of Forestry, Jakarta, pp 940–978
Hisham A, Bai MDA, Kumar GJ, Nair MS, Fujimoto Y (2001) Triterpenoids from Dysoxylum malabaricum. Phytochemistry 56:331–334. https://doi.org/10.1016/S0031-9422(00)00413-1
Hisham A, Jayakumar G, Bai MDA, Fujimoto Y (2004) Beddomeilactone: a new triterpene from Dysoxylum beddomei. Nat Prod Res 18:329–334. https://doi.org/10.1080/14786410310001626820
Hu J, Wang X, Shi X (2011) Triterpenoids and limonoids from Dysoxylum lukii with cytotoxic and antimicrobial activities. Eur J Org Chem. https://doi.org/10.1002/ejoc.201101182
Hu J, Song Y, Li H, Yang B, Mao X, Zhao YM, Shi X (2014a) Cytotoxic and anti-inflammatory tirucallane triterpenoids from Dysoxylum binectariferum. Fitoterapia 99:86–91. https://doi.org/10.1016/j.fitote.2014.09.010
Hu J, Song Y, Li H, Mao X, Zhao M, Shi X, Yang B (2014b) Antibacterial and ctotoxic triterpenoid from the ethanol extract of Dysoxylum densiflorum (Blume) Miq. Phytochem Lett 10:219–223. https://doi.org/10.1016/j.phytol.2014.09.015
Huang R, Harrison LJ, Sim KY (1999) A triterpenoid with a novel abeo-dammarane skeleton from Dysoxylum cauliflorum. Tetrahedron Lett 40:1607–1610. https://doi.org/10.1016/S0040-4039(98)02657-4
Huang HL, Wang CM, Wang ZH, Yao MJ, Han GT, Yuan JC, Gao K, Yuan CS (2011) Tirucallane-type triterpenoids from Dysoxylum lenticellatum. J Nat Prod 74:2235–2242. https://doi.org/10.1021/np2006296
Huang R, Zhao Y, Wang Y, Zhou L, Chen YF, Wang JF (2017) Cytotoxic ring A-seco triterpenoids from the stem bark of Dysoxylum lukii. J Asian Nat Prod Res 20:860–866. https://doi.org/10.1080/10286020.2017.1399880
Ismail IS, Nagakura Y, Hirasawa Y, Hosoya T, Lazim MIM, Lajis NH, Morita H (2009) Acutaxylines A and B, two novel triterpenes from Dysoxylum acutangulum. Tetrahedron Lett 50:4830–4832. https://doi.org/10.1016/j.tetlet.2009.05.110
Jain SK, Dafilips RA (1991) Medicinal Plants of India vol-2. Reference Publi INC, Algonac
Jiang K, Chen LL, Wang SF, Wang Y, Li Y, Gao K (2015) Anti-inflammatory terpenoids from the leaves and twigs of Dysoxylum gotadhora. J Nat Prod 78:1037–1044. https://doi.org/10.1021/np5010196
Jogia MK, Andersen RJ (1987) Dysoxylin, a limonoid from Dysoxylum richii. Phytochemistry 26:3309–3311. https://doi.org/10.1016/S0031-9422(00)82494-2
Kashiwada Y, Fujioka T, Chang JJ, Chen IS, Mihashi K, Lee KH (1992) Anti-tumor agents. 136. Cumingianosides A-F, potent antileukemic new triterpen glucosides and cumindysosides A and B, trisnor- and tetranortriterpene glucosides with a 14,18-cycloapoeuphane-type skeleton from Dysoxylum cumingianum. J Nat Prod 57:6946–6953. https://doi.org/10.1021/jo00051a050
Kashiwada Y, Fujioka T, Mihashi K, Marubayashi N, Mizuki K, Chen IS, Lee KH (1995) Antitumor agents, 157. Absolute structures of cumingianosides A-F, antileukemic triterpene glucosides and structures of the hydrolysates of cumingianoside A. J Nat Prod 58:495–503. https://doi.org/10.1021/np50118a003
Kashiwada Y, Fujioka T, Mihashi K, Chen IS, Katayama H, Ikeshiro Y, Lee KH (1997) Antitumor agents. 180. Chemical studies and cytotoxic evaluation of cumingianosides and cumindysosides A, antileukemic triterpene glucosides with a 14,18-cycloapotirucallane skeleton. J Nat Prod 6:1105–1114. https://doi.org/10.1021/np970256r
Khanh PN, Tai BH, Huong TT, Anh HTN, Ha VT, Kim YH, Song SB, Cuong TD, Cuong NM (2021) Dammarane triterpenes and phytosterols from Dysoxylum tpongense Pierre and their anti-inflammatory activity against liver X receptors and NF-κB activation. Steroids. https://doi.org/10.1016/j.steroids.2021.108902
Kumar Vinod R (2005) Keralathile vanavrukshangal. DC Books, Kottayam
Kurimoto S, Kashiwada Y, Lee KH, Takaishi Y (2011) Triterpenes and a triterpene glucoside from Dysoxylum cumingianum. Phytochemistry 72:2205–2211. https://doi.org/10.1016/j.phytochem.2011.08.002
Laksmi V, Pandey K, Agarwal SK (2009) Bioactivity of the compounds in genus Dysoxylum. Acta Ecol Sinica 29:30–44. https://doi.org/10.1016/j.chnaes.2009.04.005
Liby KT, Yore MM, Sporn MB (2007) Triterpenoids and rexinoids as multifunctional agents for the prevention and treatment of cancer. Nat Rev Cancer 7:357–369. https://doi.org/10.1038/nrc2129
Liu H, Heilmann J, Rali T, Sticher O (2001) New tirucallane-type triterpenes from Dysoxylum variabile. J Nat Prod 6:159–163. https://doi.org/10.1021/np0002841
Liu HB, Zhang CR, Dong SH, Yang SP, Sun Q, Geng MY, Yue JM (2012a) Sesquiterpenes from Dysoxylum oliganthum and Dysoxylum excelsum. J Asian Nat Res 14:224–234. https://doi.org/10.1080/10286020.2011.645810
Liu WX, Tang GH, He HP, Zhang Y, Li SL, Hao XJ (2012b) Limonoids and triterpenoids from the twigs and leaves of Dysoxylum hainanense. Nat Prod Bioprospect 2:29–34. https://doi.org/10.1007/s13659-011-0030-8
Luo XD, Wu SH, Ma YB, Wu DG (2000) Tirucallane triterpenoids from Dysoxylum hainanense. Phytochemistry 54:801–805. https://doi.org/10.1016/S0031-9422(00)00172-2
Luo XD, Wu SH, Wu DG, Ma YB, Qi SH (2002) Novel antifeeding limonoids from Dysoxylum hainanense. Tetrahedron 58:7797–7804. https://doi.org/10.1016/S0040-4020(02)00944-4
Mabberley DJ, Pannell CM, Sing AM (1995) Flora Malesiana: series i. Spermatophyta 12:200–285
Mohamad K, Martin MT, Litaudon M, Gaspard C, Sevenet T, Pais M (1999) Tirucallane triterpenes from Dysoxylum macranthum. Phytochemistry 52:1461–1468. https://doi.org/10.1016/S0031-9422(99)00455-0
Muholland DA, Naidoo N (2000) Dammarane triterpenoids from Dysoxylum muellerii. Biochem Syst Ecol 28:295–297. https://doi.org/10.1016/S0305-1978(99)00063-0
Mulholland DA, Monkhe TV, Pegel KH, Taylor DAH (1999) Limonoids and diterpenoids from Dysoxylum spectabile (Meliaceae). Biochem Syst Ecol 27:313–315. https://doi.org/10.1016/S0305-1978(98)00066-0
Nagakura Y, Yamanaka R, Hirasawa Y, Hosoya T, Rahman A, Kusumawati I, Zaini NC, Morita H (2010) Gaudichaudysolin A, a new limonoid from the bark of Dysoxylum gaudichaudianum. Heterocycles 80:1471–1477. https://doi.org/10.3987/COM-09-S(S)106
Nathan SS, Kalaivani K, Sehoon K (2006) Effects of Dysoxylum malabaricum Bedd. (Meliaceae) extract on the malarial vector Anopheles stephensi Liston (Diptera: Culicidae). Bioresour Technol 97:2077–2083. https://doi.org/10.1016/j.biortech.2005.09.034
Nathan SS, Hisham A, Jayakumar G (2009) Larvacidal and growth inhibition of the malaria vector Anopheles stephensi by triterpenes from Dysoxylum malabaricum and Dysoxylum beddomei. Fitoterapia 79:106–111. https://doi.org/10.1016/j.fitote.2007.07.013
Nugroho AE, Momota T, Sugiura R, Hanzawa M, Yajima E, Nagakura Y, Yasuda N, Hirasawa Y, Wong CP, Kaneda T, Hadi AHA, Fukaya H, Morita H (2014) Dysotriflorins A–M, triterpenoids from Dysoxylum densiflorum. Tetrahedron 70:9661–9667. https://doi.org/10.1016/j.tet.2014.10.070
Ragasa CY, Torres OB, Bernardo LO, Mandia EH, Don MJ, Shen CC (2013) Glabretal-type triterpenoids from Dysoxylum mollissimum. Phytochem Lett 6:514–518. https://doi.org/10.1016/j.phytol.2013.06.010
Singh Y, Aalberdberg W (1992) Dammarane triterpenids from Dysoxylum richii. Phytochemistry 31:4033–4035. https://doi.org/10.1016/0031-9422(91)85280-D
Singh S, Garg HS, Khanna NM (1976) Dysobinin, a new tetranortriterpene from Dysoxylum binectariferum. Phytochemistry 15:2001–2002. https://doi.org/10.1016/S0031-9422(00)88877-9
Sun H, Zhang XT, Wang L, Zhang XQ, Wang Y, Chen SB, Xiao PG, Ye WC (2008) Four new Cycloartane (= 9, 19-Cyclolanostane) Saponins from the Aerial Parts of Thalictrum fortunei. Helv Chim Acta 91:1961–1966. https://doi.org/10.1002/hlca.200890210
Tan QG, Luo XD (2011) Meliaceous limonoids: chemistry and biological activities. Chem Rev 111:7437–7522. https://doi.org/10.1021/cr9004023
Tang T, Liao SG, Na Z, Li Y, Xu YK (2012) Dysoxylentin A, the first 21-nortriterpenoid bearing a 2-(propan-2-ylidenyl)furan-3(2H)-one, from Dysoxylum lenticellatum. Tetrahedron Lett 53:1183–1185. https://doi.org/10.1016/j.tetlet.2011.12.109
Wang F, Guan Y (2012) Cytotoxic nor-dammarane triterpenoids from Dysoxylum hainanense. Fitoterapia 83:13–17. https://doi.org/10.1016/j.fitote.2011.08.006
Xie BJ, Yang SP, Yue JM (2008) Terpenoids from Dysoxylum densiflorum. Phytochemistry 69:2993–2997. https://doi.org/10.1016/j.phytochem.2008.09.017
Xu J, Ni G, Yang S, Yue J (2013) Dysoxylumins A–F: six new limonoids from Dysoxylum mollissimum Bl. Chinese J Chem 31:72–78. https://doi.org/10.1002/CJOC.201200838
Yan HJ, Wang JS, Kong LY (2014a) Cytotoxic dammarane-type triterpenoids from the stem bark of Dysoxylum binecteriferum. J Nat Prod 77:234–242. https://doi.org/10.1021/np400700g
Yan HJ, Wang JS, Kong LY (2014b) Cytotoxic steroids from the leaves of Dysoxylum binectariferum. Steroids 86:26–31. https://doi.org/10.1016/j.steroids.2014.04.014
Yan HJ, Si HL, Zhao HW, Chen L, Yu JQ, Zhao HQ, ang, Wang X (2021) Four new cycloartane triterpenoids from the leaves of Dysoxylum binectariferum. Phytochem Lett 41:101–105. https://doi.org/10.1016/j.phytol.2020.11.013
Zainuddin A, Meilanie SR, Darwati K, Nurlelasari TH (2020) Cytotoxic triterpenoids from the stem barks of Dysoxylum arborescens and Dysoxylum excelsum against MCF-7 breast cancer cell. Sains Malays 49:989–994. https://doi.org/10.17576/jsm-2020-4905-03
Zhang XY, Li Y, Wang YY, Cai XH, Feng T, Luo XD (2010) Tirucallane-type alkaloids from the bark of Dysoxylum laxiracemosum. J Nat Prod 73:1385–1388. https://doi.org/10.1021/np100307f
Zhang P, Lin Y, Wang F, Fang D, Zhang G (2019) Diterpenes from Dysoxylum lukii Merr. Phytochem Lett 29:53–56. https://doi.org/10.1016/j.phytol.2018.09.012
Zhao JX, Yu YY, Wang SS, Huang SL, Shen Y, Gao XH, Sheng L, Li JY, Leng Y, Li J, Yue JM (2018) Structural elucidation and bioinspired total syntheses of ascorbylated diterpenoid hongkonoids A-D. J Am Chem Soc 140:2485–2492. https://doi.org/10.1021/jacs.7b10135
Zhou B, Shen Y, Wu Y, Leng Y, Yue JM (2015) Limonoids with 11b-hydroxysteroid dehydrogenase type1 inhibitory activities from Dysoxylum mollissimum. J Nat Prod 78:2116–2122. https://doi.org/10.1021/acs.jnatprod.5b00442
Zou YH, Liu WT, Zhang JX, Xiang DC (2017) Triterpenoids from the bark of Dysoxylum hainanense and their anti-inflammatory and radical scavenging activity. Fitoterapia 121:159–163. https://doi.org/10.1016/j.fitote.2017.07.012
Acknowledgements
The authors are grateful to the Universitas Padjadjaran, Indonesia, for providing the funds for this study under the Review Article Grant, No: 1733/UN6.3.1/LT/2020, by Tri Mayanti and Academic Leadership Grant, No: 1959/UN6.3.1/PT.00/2021 by Unang Supratman.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Naini, A.A., Mayanti, T. & Supratman, U. Triterpenoids from Dysoxylum genus and their biological activities. Arch. Pharm. Res. 45, 63–89 (2022). https://doi.org/10.1007/s12272-022-01371-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-022-01371-9