Abstract
The species Caesalpinia s.l. (Leguminosae: Caesalpinioideae) are widely distributed over all continents and content a large amount of unusual secondary metabolites with vast biological potential. Traditionally, this genus includes more than 150 species, but currently, in an attempt to group the species by similar phylogenetic characteristics, Caesalpinia s.l. was categorized into the following nine different genera: Caesalpinia s.s., Coulteria, Erythrostemon, Guilandina, Libidibia, Mezoneuron, Poincianella, Pomaria and Tara. Recently, some taxonomic groups were relocated to genera from the informal Caesalpinia Group, such as Cenostigma, Moullava, Biancaea and Hultholia. However, pharmacological and chemical studies continue to use the original genera in their research. Eight hundred thirty-one compounds, including 479 new occurrences in natural products, have been identified and described in the literature in the last decade. Despite the large number of studies, the main species remain scientifically unexplored. Of the more than 140 species belonging to the segregated genera, only 30 species were analysed in chemical studies, all of which are described in this work. A review of the taxonomy of the genus Caesalpinia s.l. revealed that the reclassification, which led to the union of species based on morphological characteristics related to chemical composition, divided species with unusual chemical constituents into distinct genera. In addition, this revision reflects on the taxonomic reclassification of the genus to update the scenario of structures already isolated in the genera and the biological and pharmacological properties of constituents obtained from Caesalpinia and the other segregated genera, considering an updated nomenclature and a previous reclassification covering the available data in the literature published from 2010 to 2022.
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Abbreviations
- ABTS:
-
2,2’-Azino-bis(3-ethylbenzothiazoline-6-sulphonic acid)
- CVB3:
-
Coxsackie virus B3 (CVB3)
- DPPH:
-
2,2-Diphenyl-1-picryl-hidrazyl
- EV71:
-
Enterovirus 71
- EtOAc:
-
Ethyl acetate
- HRV1B:
-
Human rhinoviruses
- IC50 :
-
50% Inhibitory concentration
- IN:
-
Integrase
- ITS:
-
Internal transcribed spacer
- l.s:
-
lato senso
- LPS:
-
Lipopolysaccharide
- NA:
-
Neuraminidase
- NAFLD:
-
Non-alcoholic fatty liver disease
- NO:
-
Nitric oxide
- ORAC-FL:
-
Oxygen radical absorbance capacity—fluorescein
- PC50 :
-
Preferential cytotoxicity
- PDE4:
-
Phosphodiesterase-4
- s.s.:
-
stricto senso
- TMV:
-
Tobacco mosaic virus
- TNF-α:
-
Tumor necrosis factor-α
- WFO:
-
The World Flora Online
References
Asati N, Yadava RN (2018) Antibacterial activity of a triterpenoid saponin from the stems of Caesalpinia pulcherrima Linn. Nat Prod Res 32:499–507. https://doi.org/10.1080/14786419.2017.1317772
Asif A, Saeed MA (2021) Cytolysin potential of some of the di and triterpenoids from the seeds of guilandina bonducella l. Acta Pharm Sci 59:615–630. https://doi.org/10.23893/1307-2080.APS.05905
Bahia MV, Santos JB, David JP, David JM (2005) Biflavonoids and other Phenolics from Caesalpinia pyramidalis (Fabaceae). Quim Nova 16:1402–1405
Bahia MV, David JP, De FF et al (2010) Occurrence of biflavones in leaves of Caesalpinia pyramidalis specimens. Quim Nova 33:1297–1300
Bao H, Le ZL, Liu QY et al (2016) Cytotoxic and pro-apoptotic effects of cassane diterpenoids from the seeds of Caesalpinia sappan in cancer cells. Molecules. https://doi.org/10.3390/molecules21060791
Barreiros ALBS, David JM, David JP (2006) Estresse oxidativo: Relação entre geração de espécies reativas e defesa do organismo. Quim Nova 29:113–123. https://doi.org/10.1590/s0100-40422006000100021
Bi D, Xia G, Liang X et al (2017) New cassane diterpenes from the fruits of Caesalpinia mimosoides Lam. Phytochem Lett 21:283–286. https://doi.org/10.1016/j.phytol.2017.07.016
Bi D, Xia G, Liang X et al (2018) Two new cassane diterpene lactams from the fruits of Caesalpinia mimosoides Lam. Nat Prod Res 32:875–879. https://doi.org/10.1080/14786419.2017.1365070Two
Câmara ACL, Gadelha ICN, Castro MB et al (2017) Embryotoxic effects of Poincianella (Caesalpinia) pyramidalis leaves on pregnant rats. J Vet Diagnostic Investig 29:137–142. https://doi.org/10.1177/1040638716682564
Carvalho JCT, Teixeira JRM, Souza PJC et al (1996) Preliminary studies of analgesic and anti-inflammatory properties of Caesalpinia ferrea crude extract. J Ethnopharmacol 53:175–178. https://doi.org/10.1016/0378-8741(96)01441-9
Chaves TP, Fernandes FHA, Santana CP et al (2016) Evaluation of the interaction between the Poincianella pyramidalis (Tul.) LP Queiroz extract and antimicrobials using biological and analytical models. PLoS ONE 11:1–24. https://doi.org/10.1371/journal.pone.0155532
Chen F-Z, Zhao Q, Yan J et al (2014) Antioxidant Activity and Antioxidant Mechanism of Brazilin and Neoprotosappanin from Caesalpinia sappan Lignum. Asian J Chem 26:4979–4981
Chen XM, Lu W, Zhang ZH et al (2022a) Cassane diterpenoids from the aerial parts of Caesalpinia pulcherrima and their antibacterial and anti-glioblastoma activity. Phytochemistry 196:113082. https://doi.org/10.1016/j.phytochem.2021.113082
Chen Y-K, Fan M-Y, Zhang Y-M et al (2022b) Three new cassane-type diterpenoids from Caesalpinia sinensis. J Asian Nat Prod Res 17:1–7. https://doi.org/10.1080/10286020.2022.2026933
Cheng J, Roach JS, McLean S et al (2008) Three new cassane diterpenes from Caesalpinia pulcherrima. Nat Prod Commun 3:1751–1754. https://doi.org/10.1177/1934578x0800301102
Choo YY, Tran PT, Min BS et al (2017) Sappanone A inhibits RANKL-induced osteoclastogenesis in BMMs and prevents inflammation-mediated bone loss. Int Immunopharmacol 52:230–237. https://doi.org/10.1016/j.intimp.2017.09.018
Cota BB, De Oliveira DM, De Siqueira EP et al (2011) New cassane diterpenes from Caesalpinia echinata. Fitoterapia 82:969–975. https://doi.org/10.1016/j.fitote.2011.05.014
Cuong TD, Hung TM, Kim JC et al (2012) Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity. J Nat Prod 75:2069–2075. https://doi.org/10.1021/np3003673
Dang PH, Nguyen MTT, Nguyen HX et al (2015) Three new cassane-type furanoditerpenes from the seed of Vietnamese Caesalpinia bonducella. Phytochem Lett 13:99–102. https://doi.org/10.1016/j.phytol.2015.05.018
Das B, Thirupathi P, Ravikanth B et al (2009) Isolation, synthesis, and bioactivity of homoisoflavonoids from Caesalpinia pulcherrima. Chem Pharm Bull 57:1139–1141. https://doi.org/10.1248/cpb.57.1139
Das B, Srinivas Y, Sudhakar C et al (2010) New diterpenoids from Caesalpinia species and their cytotoxic activity. Bioorganic Med Chem Lett 20:2847–2850. https://doi.org/10.1016/j.bmcl.2010.03.048
De Oliveira JCS, David JM, David JP (2016a) Composição química das cascas das raízes e flores de poincianella pyramidalis (fabaceae). Quim Nov 39:189–193. https://doi.org/10.5935/0100-4042.20160015
De Oliveira JCS, David JP, David JM (2016c) Biflavonoids from the bark roots of poincianella pyramidalis (fabaceae). Phytochem Lett 16:18–22. https://doi.org/10.1016/j.phytol.2016.02.017
De Souza JE, Do Nascimento MFA, Borsodi MPG et al (2018) Leaves from the tree poincianella pluviosa as a renewable source of antiplasmodial compounds against chloroquine-resistant plasmodium falciparum. J Braz Chem Soc 29:1318–1327. https://doi.org/10.21577/0103-5053.20170228
Deng ZT, Su J, Ding LF et al (2016) Six new cassane diterpenoids from the seeds of Caesalpinia sappan. Phytochem Lett 16:207–212. https://doi.org/10.1016/j.phytol.2016.04.014
Domingos ODS, Alcântara BGV, Santos MFC et al (2019a) Anti-inflammatory derivatives with dual mechanism of action from the metabolomic screening of poincianella pluviosa. Molecules. https://doi.org/10.3390/molecules24234375
Domingos ODS, Alcântara BGV, Santos MFC et al (2019b) Anti-inflammatory derivatives with dual mechanism of action from the metabolomic screening of poincianella pluviosa. Molecules 24:1–20. https://doi.org/10.3390/molecules24234375
Dong R, Yuan J, Wu S et al (2015) Anti-inflammation furanoditerpenoids from Caesalpinia minax Hance. Phytochemistry 117:325–331. https://doi.org/10.1016/j.phytochem.2015.06.025
Dos Reis SDS, De Oliveira RS, Correia Marcelino SA et al (2016) Congenital malformations and other reproductive losses in goats due to poisoning by Poincianella pyramidalis (Tul.) L.P. Queiroz (=Caesalpinia pyramidalis Tul.). Toxicon 118:91–94. https://doi.org/10.1016/j.toxicon.2016.04.043
Dos Santos JRS, Lopes JRG, Medeiros MA et al (2018) Embryonic mortality and abortion in goats caused by ingestion of Poincianella pyramidalis. Pesqui Vet Bras 38:1259–1263. https://doi.org/10.1590/1678-5150-PVB-5480
Emam M, El Raey MA, El-Haddad AE et al (2019) A new polyoxygenated flavonol gossypetin-3-o-β-d-robinobioside from Caesalpinia gilliesii (Hook.) D. Dietr. and in vivo hepatoprotective, anti-inflammatory, and anti-ulcer activities of the leaf methanol extract. Molecules 24:1–12. https://doi.org/10.3390/molecules24010138
Erharuyi O, Adhikari A, Falodun A et al (2016) Derivatization of cassane diterpenoids from Caesalpinia pulcherrima (L.) Sw. and evaluation of their cytotoxic and leishmanicidal activities. Tetrahedron Lett 57:2201–2206. https://doi.org/10.1016/j.tetlet.2016.04.030
Erharuyi O, Adhikari A, Falodun A et al (2017) Cytotoxic, Anti-inflammatory, and Leishmanicidal Activities of Diterpenes Isolated from the Roots of Caesalpinia pulcherrima. Planta Med 83:104–110. https://doi.org/10.1055/s-0042-110407
Essoung FRE, Mba’ning BM, Lwande W, et al (2017) Welwitschianalol A and B, two cyclohexene derivatives and other insecticidal constituents of Caesalpinia welwitschiana (Oliv.) Brenan. Phytochem Lett 22:81–86. https://doi.org/10.1016/j.phytol.2017.09.010
Famojuro TI, Elufioye TO, Olajide OA et al (2021) New cytotoxic compounds from the leaves of Caesalpinia benthamiana (Baill.) Herend. & Zarucchi (Fabaceae). Orig Res Artic 11:54–67
Felipe González A, Gutiérrez Gaitén YI, Scull Lizama R et al (2020) A new homoisoflavonoid from Caesalpinia bahamensis. Rev Bras Farmacogn 30:733–736. https://doi.org/10.1007/s43450-020-00108-3
Ferreira RO, De Carvalho MG, Da Silva TMS (2012) Ocorrência de biflavonoides em clusiaceae: aspectos químicos e farmacológicos. Quim Nova 35:2271–2277. https://doi.org/10.1590/S0100-40422012001100035
Flores Y, Vila J, Almanza GR (2006) Secondary metabolites from Caesalpinia pluviosa. Rev Boliv Física 23:1–10
Fun HK, Yodsaoue O, Karalai C, Chantrapromma S (2010) Absolute configuration of isovouacapenol C. Acta Crystallogr Sect E Struct Reports Online. https://doi.org/10.1107/S1600536810028023
Gagnon E, Lewis GP, Solange Sotuyo J et al (2013) A molecular phylogeny of Caesalpinia sensu lato: Increased sampling reveals new insights and more genera than expected. South African J Bot 89:111–127. https://doi.org/10.1016/j.sajb.2013.07.027
Gagnon E, Bruneau A, Hughes CE et al (2016) A new generic system for the pantropical Caesalpinia group (Leguminosae). PhytoKeys 71:1–160. https://doi.org/10.3897/phytokeys.71.9203
Gasson P, Warner K, Lewis G (2009) Wood anatomy of Caesalpinia s.s., coulteria, erythrostemon, guilandina, libidibia, mezoneuron, poincianella, pomaria and tara (leguminosae, caesalpinioideae, caesalpinieae). IAWA J 30:247–276
Gómez-Hurtado MA, Álvarez-Esquivel FE, Rodríguez-García G et al (2013) Cassane diterpenes from Caesalpinia platyloba. Phytochemistry 96:397–403. https://doi.org/10.1016/j.phytochem.2013.09.028
Hanson JR (2011) Diterpenoids of terrestrial origin. Nat Prod Rep 28:1755–1772. https://doi.org/10.1039/c1np90021h
Hanson JR (2016) Diterpenoids of terrestrial origin. Nat Prod Rep 33:1227–1238. https://doi.org/10.1039/c6np00059b
Hanson JR (2017) Diterpenoids of terrestrial origin. Nat Prod Rep 34:1233–1243. https://doi.org/10.1039/c7np00040e
He D, Li Y, Tang H et al (2015) Six new cassane diterpenes from the twigs and leaves of Tara (Caesalpinia spinosa Kuntze). Fitoterapia 105:273–277. https://doi.org/10.1016/j.fitote.2015.07.018
He DY, Li YP, Tang HB et al (2016) Phenolic compounds from the twigs and leaves of Tara (Caesalpinia spinosa). J Asian Nat Prod Res 18:334–338. https://doi.org/10.1080/10286020.2015.1096269
He D, Ma R, Li Y et al (2017) Chemical Constituents of the Twigs of Caesalpinia mimosoides. Chem Nat Compd 53:545–547. https://doi.org/10.1007/s10600-017-2043-y
Huang C, Xu Y, Chen J et al (2021) Lipid lowering effects in hepatocytes of cassane-type diterpenoids from the seeds of Caesalpinia minax Hance. Phytochem Lett 43:163–168. https://doi.org/10.1016/j.phytol.2021.03.018
Iheagwam FN, Ogunlana OO, Ogunlana OE et al (2019) Potential anti-cancer flavonoids isolated from Caesalpinia bonduc young twigs and leaves: Molecular docking and in silico studies. Bioinform Biol Insights. https://doi.org/10.1177/1177932218821371
Islam MT, Zihad SMNK, Rahman MS et al (2019) Agathisflavone: botanical sources, therapeutic promises, and molecular docking study. IUBMB Life 71:1192–1200. https://doi.org/10.1002/iub.2053
Ji Y, Zhang Y, Liu T et al (2019) Chemical constituents from heartwoods of Caesalpinia sappan with antiplatelet aggregation activities. Chinese Herb Med 11:423–428. https://doi.org/10.1016/j.chmed.2019.09.001
Jin Y, Wang M, Yan YF et al (2022) Bridged cassane derivatives from the seeds of Caesalpinia sappan L. and their cytotoxic activities. Phytochemistry 197:113111. https://doi.org/10.1016/j.phytochem.2022.113111
Jing W, Zhang XX, Zhou H et al (2019) Naturally occurring cassane diterpenoids (CAs) of Caesalpinia: a systematic review of its biosynthesis, chemistry and pharmacology. Fitoterapia 134:226–249. https://doi.org/10.1016/j.fitote.2019.02.023
Jung EG, Il HK, Kwon HJ et al (2015) Anti-inflammatory activity of sappanchalcone isolated from Caesalpinia sappan L. in a collagen-induced arthritis mouse model. Arch Pharm Res 38:973–983. https://doi.org/10.1007/s12272-015-0557-z
Kamikawa S, Ohta E, Ohta S (2015) Caesaljaponins A and B: new cassane-type furanoditerpenoids from the seeds of Caesalpinia decapetala var japonica. Helv Chim Acta 98(3):336–342
Kamikawa S, Oshimo S, Ohta E et al (2016) Cassane diterpenoids from the roots of Caesalpinia decapetala var. japonica and structure revision of caesaljapin. Phytochemistry 121:50–57. https://doi.org/10.1016/j.phytochem.2015.10.001
Kim HP, Park H, Son KH et al (2008) Biochemical pharmacology of biflavonoids: Implications for anti-inflammatory action. Arch Pharm Res 31:265–273. https://doi.org/10.1007/s12272-001-1151-3
Kim JH, Choo YY, Tae N et al (2014) The anti-inflammatory effect of 3-deoxysappanchalcone is mediated by inducing heme oxygenase-1 via activating the AKT/mTOR pathway in murine macrophages. Int Immunopharmacol 22:420–426. https://doi.org/10.1016/j.intimp.2014.07.025
Kumar R, Patel DK, Prasad SK et al (2012) Type 2 antidiabetic activity of bergenin from the roots of Caesalpinia digyna Rottler. Fitoterapia 83:395–401. https://doi.org/10.1016/j.fitote.2011.12.008
Kumar A, Garg V, Chaudhary A et al (2014) Isolation, characterisation and antibacterial activity of new compounds from methanolic extract of seeds of Caesalpinia crista L. (Caesalpinaceae). Nat Prod Res 28:230–238. https://doi.org/10.1080/14786419.2013.814054
Kumar MP, Sankeshi V, Naik RR et al (2015) The inhibitory effect of Isoflavones isolated from Caesalpinia pulcherrima on aldose reductase in STZ induced diabetic rats. Chem Biol Interact 237:18–24. https://doi.org/10.1016/j.cbi.2015.05.010
Lee S, Choi SY, Choo YY et al (2015) Sappanone A exhibits anti-inflammatory effects via modulation of Nrf2 and NF-κB. Int Immunopharmacol 28:328–336. https://doi.org/10.1016/j.intimp.2015.06.015
Leng L-F, Lai Q, Lv D et al (2021) Study on the chemical composition of Caesalpinia sinensis. Nat Prod Res 29:1–8. https://doi.org/10.1080/14786419.2021.2021518
Lewis GP (2020) New combinations in Guilandina (Leguminosae: Caesalpinioideae). Kew Bull 75:9–11. https://doi.org/10.1007/s12225-020-9865-7
Lewis GP, Hughes CE, Yomona AD et al (2010) Three new legumes endemic to the Marañón Valley, Perú. Kew Bull 65:209–220. https://doi.org/10.1007/s12225-010-9203-6
Li DM, Ma L, Liu GM, Hu LH (2006) Cassane diterpene-lactones from the seed of Caesalpinia minax HANCE. Chem Biodivers 3:1260–1265. https://doi.org/10.1002/cbdv.200690128
Li Q, He YN, Niu B et al (2016) Caesalmins N-Q, new cassane diterpenes from the seeds of Caesalpinia minax. Phytochem Lett 17:23–27. https://doi.org/10.1016/j.phytol.2016.06.008
Li ZY, Li QZ, Ma GX et al (2017) Cassane-type diterpenes from Caesalpinia minax induce apoptosis in pituitary adenoma: structure–activity relationship, ER stress and Wnt/β-catenin pathways. J Asian Nat Prod Res 19:423–435. https://doi.org/10.1080/10286020.2016.1217520
Li CH, Zhang JY, Tuong TML et al (2020) Cassane Diterpenoids from the Aerial Parts of Caesalpinia pulcherrima and Their Antifeedant and Insecticidal Activities against Mythimna separate and Plutella xylostella. J Agric Food Chem 68:4227–4236. https://doi.org/10.1021/acs.jafc.0c00853
Lian L, Bin LX, Yuan JZ et al (2015) Two new diterpenes from the seeds of Caesalpinia minax Hance. J Asian Nat Prod Res 17:893–899. https://doi.org/10.1080/10286020.2015.1039998
Liang X, Bi D, Li F, Wang L (2019) Chemical compounds from the twigs and leaves of Caesalpinia cucullata Roxb. Rec Nat Prod. 13:462–467. https://doi.org/10.25135/rnp.124.18.12.1088
Lin L, Cao J, Xu Y et al (2021) Cassane-type Diterpenoids from the Seeds of Caesalpinia bonduc (L.) Roxb. Chem Biodivers. https://doi.org/10.1002/cbdv.202100309
Liu H, Ma G, Yuan J et al (2013) A New cassane-type diterpene and other constituents from Caesalpinia minax. Bull Korean Chem Soc 34:1541–1542. https://doi.org/10.5012/bkcs.2013.34.5.1541
Liu QB, Huang L, Zhang L et al (2015) Two new cassane-type diterpenes from the seeds of Caesalpinia crista. J Asian Nat Prod Res 17:1073–1078. https://doi.org/10.1080/10286020.2015.1054379
Liu X, Yu D, Wang T (2016) Sappanone a attenuates allergic airway inflammation in ovalbumin-induced asthma. Int Arch Allergy Immunol 170:180–186. https://doi.org/10.1159/000448331
Liu Q, Bai B, Shen J et al (2018a) Three new diterpenes from the seeds of Caesalpinia minax Hance and their anti-inflammatory activity. Phytochem Lett 26:93–95. https://doi.org/10.1016/j.phytol.2018.05.010
Liu Q, Bai B, Yang D, po, et al (2018b) Three new cassane diterpenes from the seeds of Caesalpinia minax Hance. Nat Prod Res 32:885–891. https://doi.org/10.1080/14786419.2017.1366480
Liu T, Wang M, Qi S et al (2020) New cassane-type diterpenoids from kernels of Caesalpinia bonduc (Linn) Roxb and their inhibitory activities on phosphodiesterase (PDE) and nuclear factor-kappa B (NF-κB) expression. Bioorg Chem 96:103573. https://doi.org/10.1016/j.bioorg.2020.103573
Liu T, Li X, Ning Z et al (2021) Two new cassane-type diterpenoids from the seed kernels of Caesalpinia bonduc (Linn.) Roxb. and their anti-inflammatory activity. Nat Prod Res 36(15):1–8
Lopes JRG, Santos JRS, Medeiros MA et al (2017) Reproductive losses caused by the ingestion of Poincianella pyramidalis in sheep. Toxicon 138:98–101. https://doi.org/10.1016/j.toxicon.2017.08.020
Lou R, Xu F, Xu Y et al (2021) Caesalpinaxin, a cassane-type diterpenoid with a 21-carbon core skeleton from the seeds of Caesalpinia minax possessing pro-angiogenetic property. Bioorg Chem 117:105426. https://doi.org/10.1016/j.bioorg.2021.105426
LPWG (2013) Towards a new classification system for legumes: Progress report from the 6th International Legume Conference. South African J Bot 89:3–9. https://doi.org/10.1016/j.sajb.2013.07.022
LPWG (2017) A new subfamily classification of the leguminosae based on a taxonomically comprehensive phylogeny. Taxon 66:44–77. https://doi.org/10.12705/661.3
Ma G, Yuan J, Wu H et al (2012a) Novel cassane diterpenes from the seeds of Caesalpinia minax. Phytochem Lett 5:617–620. https://doi.org/10.1016/j.phytol.2012.06.007
Ma GX, Xu N, Yuan JQ et al (2012b) Two new diterpenes, neocaesalpin MR and minaxin C, from Caesalpinia minax. J Asian Nat Prod Res 14:1156–1161. https://doi.org/10.1080/10286020.2012.734504
Ma GX, Xu XD, Cao L et al (2012c) Cassane-type diterpenes from the seeds of Caesalpinia minax with their antineoplastic activity. Planta Med 78:1363–1369. https://doi.org/10.1055/s-0032-1314976
Ma RJ, Hu JM, Yang XY, Wang LQ (2012d) The new Cassane-Type diterpenes from Caesalpinia minax. Chem Pharm Bull 60:759–763. https://doi.org/10.1002/hlca.201300401
Ma G, Yuan J, Wu H et al (2013) Caesalpins A-H, bioactive cassane-type diterpenes from the seeds of Caesalpinia minax. J Nat Prod 76:1025–1031. https://doi.org/10.1021/np300918q
Ma G, Sun Z, Sun Z et al (2014a) Antimalarial diterpene alkaloids from the seeds of Caesalpinia minax. Fitoterapia 95:234–239. https://doi.org/10.1016/j.fitote.2014.04.001
Ma GX, Wu HF, Yuan JQ et al (2014b) Further Diterpenes from the seeds of Caesalpinia minax Hance. Helv Chim Acta 97:581–586. https://doi.org/10.1002/hlca.201300220
Ma GX, Di ZhuY, Sun ZH et al (2014c) Three new cassane diterpenes from the seeds of Caesalpinia sappan. Phytochem Lett 8:141–144. https://doi.org/10.1016/j.phytol.2014.03.008
Ma R, Hu J, Yang X, Wang L (2014d) Three New Cassane-Type Diterpenes from Caesalpinia minax flavonoids. Helv Chim Acta 97:1009–1013
Ma G, Wu H, Chen D et al (2015) Antimalarial and Antiproliferative Cassane Diterpenes of Caesalpinia sappan. J Nat Prod 78:2364–2371. https://doi.org/10.1021/acs.jnatprod.5b00317
Ma GX, Chen P, Sun ZH et al (2016) Novel cassane diterpenes from the seeds of Caesalpinia decapetala and their antiproliferative activity. Phytochem Lett 16:52–55. https://doi.org/10.1016/j.phytol.2016.03.002
Maheswara MM, Iddaiah VS, Ao CVER (2006) Two new homoisoflavonoids from C. pulcherrima. Chem Pharm Bull 54:1193–1195
Mendes CC, Bahia MV, David JM, David JP (2000) Constituents of Caesalpinia pyramidalis. Fitoterapia 71:205–207. https://doi.org/10.1016/S0367-326X(99)00145-8
Min BS, Cuong TD, Hung TM et al (2012) Compounds from the heartwood of Caesalpinia sappan and their anti-inflammatory activity. Bioorganic Med Chem Lett 22:7436–7439. https://doi.org/10.1016/j.bmcl.2012.10.055
Mitsui T, Ishihara R, Hayashi KI et al (2014) New cassane-type diterpenoids of Caesalpinia echinata (Leguminosae) exhibiting NF-κB inhibitory activities. Chem Pharm Bull 62:267–273. https://doi.org/10.1248/cpb.c13-00812
Mitsui T, Ishihara R, Hayashi KI et al (2015) Cassane-type diterpenoids from Caesalpinia echinata (Leguminosae) and their NF-κB signaling inhibition activities. Phytochemistry 116:349–358. https://doi.org/10.1016/j.phytochem.2015.03.012
Moraes de da SZC, Shan AYKV, Oliveira Melo MA et al (2020) Antinociceptive and anti-inflammatory effect of Poincianella pyramidalis (Tul.) L.P. Queiroz. J Ethnopharmacol 254:1–9. https://doi.org/10.1016/j.jep.2020.112563
Mu W, Tang H, Li Y et al (2016) Caesalpinone A, a new type of gorgonane sesquiterpenoid containing an unprecedented 1,15-bridge, from the pods of Caesalpinia spinosa Kuntze. Fitoterapia 112:233–236. https://doi.org/10.1016/j.fitote.2016.06.012
Mueller M, Weinmann D, Toegel S et al (2016) Compounds from Caesalpinia sappan with anti-inflammatory properties in macrophages and chondrocytes. Food Funct 7:1671–1679. https://doi.org/10.1039/c5fo01256b
Nawwar M, El-Mousallami A, Hussein S et al (2014) Three new Di-O-glycosyl-C-glucosyl flavones from the leaves of Caesalpinia Ferrea mart. Zeitschrift Fur Naturforsch - Sect C J Biosci 69:357–362. https://doi.org/10.5560/ZNC.2014-0113
Nawwar MA, Hussein SA, El-Mousallami AM et al (2015) Phenolics from Caesalpinia ferrea Mart.: Antioxidant, cytotoxic and hypolipidemic activity. Pharmazie 70:553–558. https://doi.org/10.1691/ph.2015.5526
Nguyen HX, Nguyen NT, Dang PH et al (2016) Cassane diterpenes from the seed kernels of Caesalpinia sappan. Phytochemistry 122:286–293. https://doi.org/10.1016/j.phytochem.2015.12.018
Nirmal NP, Panichayupakaranant P (2014) Anti-Propionibacterium acnes assay-guided purification of brazilin and preparation of brazilin rich extract from Caesalpinia sappan heartwood. Pharm Biol 52:1204–1207. https://doi.org/10.3109/13880209.2014.884607
Niu Y, Wang S, Li C et al (2020) Effective Compounds From Caesalpinia sappan L on the Tyrosinase In Vitro and In Vivo. Nat Prod Commun. https://doi.org/10.1177/1934578X20920055
Nondo RSO, Moshi MJ, Erasto P et al (2017) Anti-plasmodial activity of Norcaesalpin D and extracts of four medicinal plants used traditionally for treatment of malaria. BMC Complement Altern Med 17:1–9. https://doi.org/10.1186/s12906-017-1673-8
Nozaki H, Ichiro Hayashi K, Kido M et al (2007) Pauferrol A, a novel chalcone trimer with a cyclobutane ring from Caesalpinia ferrea mart exhibiting DNA topoisomerase II inhibition and apoptosis-inducing activity. Tetrahedron Lett 48:8290–8292. https://doi.org/10.1016/j.tetlet.2007.09.130
Ochieng CO, Owuor PO, Mang Uro LAO et al (2012) Antinociceptive and antiplasmodial activities of cassane furanoditerpenes from Caesalpinia volkensii H. root bark. Fitoterapia 83:74–80. https://doi.org/10.1016/j.fitote.2011.09.015
Ochieng CO, Manguro LAO, Owuor PO, Akala H (2013) Voulkensin C-E, new 11-oxocassane-type diterpenoids and a steroid glycoside from Caesalpinia volkensii stem bark and their antiplasmodial activities. Bioorganic Med Chem Lett 23:3088–3095. https://doi.org/10.1016/j.bmcl.2013.03.007
Ogbeide KO, Kumar R, Rehman MU et al (2018) Crystal structure and Hirshfeld surface analysis of the naturally occurring cassane-type diterpenoid, 6β-cinnamoyl-7β-hydroxyvouacapen-5α-ol. Acta Crystallogr Sect E Crystallogr Commun 74:385–389. https://doi.org/10.1107/S2056989018002499
Ogunlana OO, He WJ, Fan JT et al (2015) Cytotoxic flavonoids from the young twigs and leaves of Caesalpinia bonduc (Linn) Roxb. Pak J Pharm Sci 28:2191–2198
Oh M, Park SJ, Song JH et al (2020) Chemical components from the twigs of Caesalpinia latisiliqua and their antiviral activity. J Nat Med 74:26–33. https://doi.org/10.1007/s11418-019-01335-2
Ohira S, Takaya K, Mitsui T et al (2013) New chalcone dimers from Caesalpinia ferrea Mart act as potent inhibitors of DNA topoisomerase II. Tetrahedron Lett 54:5052–5055. https://doi.org/10.1016/j.tetlet.2013.07.028
Olmedo-Juárez A, Briones-Robles TI, Zaragoza-Bastida A et al (2019) Antibacterial activity of compounds isolated from Caesalpinia coriaria (Jacq) Willd against important bacteria in public health. Microb Pathog 136:103660. https://doi.org/10.1016/j.micpath.2019.103660
Pournaghi N, Khalighi-Sigaroodi F, Safari E, Hajiaghaee R (2021) Bioassay-guided isolation of flavonoids from Caesalpinia bonduc (L.) roxb. and evaluation of their cytotoxicity. Iran J Pharm Res 20:274–282. https://doi.org/10.22037/ijpr.2020.112557.13824
Promsawan N, Kittakoop P, Boonphong S, Nongkunsarn P (2003) Antitubercular cassane furanoditerpenoids from the roots of Caesalpinia pulcherrima. Planta Med 69:776–777. https://doi.org/10.1055/s-2003-42782
Pudhom K, Sommit D, Suwankitti N, Petsom A (2007) Cassane furanoditerpenoids from the seed kernels of Caesalpinia bonduc from Thailand. J Nat Prod 70:1542–1544. https://doi.org/10.1021/np070330y
Qiao Y, Xu Q, Hu Z et al (2016) Diterpenoids of the Cassane Type from Caesalpinia decapetala. J Nat Prod 79:3134–3142. https://doi.org/10.1021/acs.jnatprod.6b00910
Qiao Y, Liu Y, Duan X et al (2018) A pair of epimeric cassane-type diterpenoids and a new labdane-type derivative from Caesalpinia decapetala. Tetrahedron 74:3852–3857. https://doi.org/10.1016/j.tet.2018.05.028
Queiroz LP de (2009) Leguminosas da caatinga, 1a. Universidade Estadual de feira de Santana
Queiroz AF de (2009) Leguminosas da caatinga, 1a. Universidade Estadual de feira de Santana
Roy SK, Agrahari UC, Gautam R et al (2012) Isointricatinol, a new antioxidant homoisoflavonoid from the roots of Caesalpinia digyna Rottler. Nat Prod Res 26:690–695. https://doi.org/10.1080/14786419.2010.548813
Ruan QF, Zhou XH, Jiang SQ et al (2019) Caesalminaxins O-T, cassane diterpenoids from the seeds of Caesalpinia minax and their anti-inflammation. Fitoterapia 134:50–57. https://doi.org/10.1016/j.fitote.2019.02.004
Seo H, Kim S, Al MH et al (2017) In vitro Antitubercular Activity of 3-Deoxysappanchalcone Isolated From the Heartwood of Caesalpinia sappan Linn. Phyther Res 31:1600–1606. https://doi.org/10.1002/ptr.5890
Sgariglia MA, Soberón JR, Poveda Cabanes A et al (2013) Anti-inflammatory properties of phenolic lactones isolated from Caesalpinia paraguariensis stem bark. J Ethnopharmacol 147:63–73. https://doi.org/10.1016/j.jep.2012.12.030
Shu SH, Deng AJ, Li ZH, Qin HL (2011) Two novel biphenyl dimers from the heartwood of Caesalpinia sappan. Fitoterapia 82:762–766. https://doi.org/10.1016/j.fitote.2011.03.010
Singh J, Kumar A, Sharma A (2017) Antianxiety activity guided isolation and characterization of bergenin from Caesalpinia digyna Rottler roots. J Ethnopharmacol 195:182–187. https://doi.org/10.1016/j.jep.2016.11.016
Siridechakorn I, Cheenpracha S, Ritthiwigrom T et al (2014) Isopimarane diterpenes and flavan derivatives from the twigs of Caesalpinia furfuracea. Phytochem Lett 7:186–189. https://doi.org/10.1016/j.phytol.2013.12.003
Srinivasan R, Chandrasekar MJN, Nanjan MJ (2011) Phytochemical investigations of Caesalpinia digyna root. E-Journal Chem 8:1843–1847. https://doi.org/10.1155/2011/630375
Subehan RY, Mufidah, et al (2014) Phytochemical investigation of the active constituents from Caesalpinia sappan on stimulation of osteoblastic cells. Plant Biotechnol 31:505–509. https://doi.org/10.5511/plantbiotechnology.14.0911a
Sun ZC, Ma GX, Yuan JQ et al (2014) Two new degradative cassane-type diterpenes isolated from Caesalpinia minax. J Asian Nat Prod Res 16:187–191. https://doi.org/10.1080/10286020.2013.864282
Tangsaengvit N, Kitphati W, Tadtong S et al (2013) Neurite outgrowth and neuroprotective effects of quercetin from Caesalpinia mimosoides lamk. on CULTURED P19-derived neurons. Evidence-Based Complement Altern Med. https://doi.org/10.1155/2013/838051
Tewtrakul S, Panthong P, Bunluepuech K et al (2015) Anti-HIV-1 Integrase Activity and Molecular Docking Study of Compounds from Caesalpinia sappan L. Pharm Biol 29:724–729. https://doi.org/10.1002/ptr.5307
Thi Huyen L, Hoang Son V, Thi Viet Hoa T et al (2022) Chemical constituents from the leaves of Caesalpinia bonduc (L) Roxb and their chemotaxonomic significance. Biochem Syst Ecol 100:104376. https://doi.org/10.1016/j.bse.2021.104376
Tian QJ, Ou YH, He XB et al (2013) One new antitumour cassane-type diterpene from Caesalpinia crista. Nat Prod Res 27:537–540. https://doi.org/10.1080/14786419.2012.676551
Tran MH, Nguyen MTT, Nguyen HD et al (2015) Cytotoxic constituents from the seeds of Vietnamese Caesalpinia sappan. Pharm Biol 53:1549–1554. https://doi.org/10.3109/13880209.2014.986686
Wang Z, Sun JB, Qu W et al (2014) Caesappin A and B, two novel protosappanins from Caesalpinia sappan L. Fitoterapia 92:280–284. https://doi.org/10.1016/j.fitote.2013.12.004
Wang DS, Nie W, Jiang TT et al (2020a) Caesalpanins A-C, Three Dimeric Cassane Diterpenoids from the Seeds of Caesalpinia sappan L. Chem Biodivers 17:1–9. https://doi.org/10.1002/cbdv.202000103
Wang M, Tan J, Chen J et al (2020b) Three new ester glycosides with cytotoxic activity from the seeds of Caesalpinia sappan. Nat Prod Res. https://doi.org/10.1080/14786419.2020.1721488
Wang M, Yang YR, Yin Y et al (2021a) New Cassane Diterpenoids from the Seed Kernels of Caesalpinia cucullata, Exhibit Anti-inflammatory Effect in vitro by Inhibiting iNOS Enzymatic Activity. Chinese J Chem 39:1625–1634. https://doi.org/10.1002/cjoc.202000683
Wang M, Yu S, Qi S et al (2021b) Anti-inflammatory Cassane-Type Diterpenoids from the Seed Kernels of Caesalpinia sinensis. J Nat Prod 84:2175–2188. https://doi.org/10.1021/acs.jnatprod.1c00233
Wang M, Zhang X, Qi M et al (2021c) New cassane- and norcassane-type diterpenoids from the seed kernels of Caesalpinia sinensis and their anti-inflammatory activity in vitro. Fitoterapia 153:104978. https://doi.org/10.1016/j.fitote.2021.104978
Wang M, Zhu T, Yu S et al (2021d) Four new cassane-type diterpenoids from the seed kernels of Caesalpinia cucullata Roxb. Nat Prod Res. https://doi.org/10.1080/14786419.2021.1919107
Wei XH, Yang SJ, Liang N et al (2013) Chemical constituents of Caesalpinia decapetala (Roth) alston. Molecules 18:1325–1336. https://doi.org/10.3390/molecules18011325
Wei H, Zheng J, Liu YH et al (2016) Cassane diterpenes from the seeds of Caesalpinia decapetala. Yaoxue Xuebao 51:1441–1444. https://doi.org/10.16438/j.0513-4870.2016-0422
Wei H, Dai LP, Yan LH et al (2017) New Cassane Diterpenes from the seeds of Caesalpinia decapetala. Magn Reson Chem 55:157–160. https://doi.org/10.1002/mrc.4507
Wu ZH, Huang J, Li WD et al (2010) Three new cassane diterpenes from the seeds of Caesalpinia minax Hance. J Asian Nat Prod Res 12:781–787. https://doi.org/10.1080/10286020.2010.504661
Wu M, Wang Y-F, Zhang M-L et al (2011) Chemical constituents of plants from the genus Caesalpinia. Chem Biodivers 8:1370–1399. https://doi.org/10.1002/cbdv.201100170
Wu HF, Hong JY, Sun ZH et al (2014a) Novel dinorcassane- and cassane-type diterpenes from the seeds of Caesalpinia minax. Fitoterapia 94:172–176. https://doi.org/10.1016/j.fitote.2014.01.021
Wu HF, Di ZhuY, Sun ZH et al (2014b) Norcassane- and cassane-type furanoditerpenoids from the seeds of Caesalpinia sappan. Fitoterapia 98:22–26. https://doi.org/10.1016/j.fitote.2014.07.001
Wu J, Chen G, Xu X et al (2014c) Seven new cassane furanoditerpenes from the seeds of Caesalpinia minax. Fitoterapia 92:168–176. https://doi.org/10.1016/j.fitote.2013.11.002
Wu L, Luo J, Zhang Y et al (2014d) Cassane-type diterpenoids from the seed kernels of Caesalpinia bonduc. Fitoterapia 93:201–208. https://doi.org/10.1016/j.fitote.2014.01.011
Wu L, Wang X, Shan S et al (2014e) New cassane-type diterpenoids from Caesalpinia bonduc. Chem Pharm Bull 62:729–733. https://doi.org/10.1248/cpb.c14-00186
Xiao F, Tang CP, Ke CQ et al (2016) Rearranged diterpenoids from the seeds of Caesalpinia sappan. Chinese Chem Lett 27:1751–1754. https://doi.org/10.1016/j.cclet.2016.04.022
Xu N, Xu XD, Ma LY et al (2010) A new homoflavonoid from the seed of Caesalpinia minax Hance. Chinese Chem Lett 21:696–698. https://doi.org/10.1016/j.cclet.2010.01.041
Xu YJ, Zhang J, Tang CP, Ye Y (2013) A new diterpenoid from the seeds of Caesalpinia sappan linn. Rec Nat Prod 7:124–128
Xu J, Cao X, Liu F et al (2016a) Characterization of diterpenoids from Caesalpinia decapetala and their anti-TMV activities. Fitoterapia 113:144–150. https://doi.org/10.1016/j.fitote.2016.07.017
Xu X, Yuan J, Zhou X et al (2016b) Cassane diterpenes with oxygen bridge from the seeds of Caesalpinia sappan. Fitoterapia 112:205–210. https://doi.org/10.1016/j.fitote.2016.06.005
Xu Y, Feng Z, Zhang T et al (2020a) Pimarane Diterpenoids from the Seeds of Caesalpinia as PTP1B Inhibitors and Insulin Sensitizers. Molecules 25:1–9
Xu Y, Shi W, Feng L et al (2020b) Anti-proliferative cassane-type diterpenoids from the seeds of Caesalpinia minax. Nat Prod Res. https://doi.org/10.1080/14786419.2020.1853729
Xu Y, Zhang T, Feng L et al (2020c) Biscaesalmins A and B from Caesalpinia minax, highly oxidized dimeric cassane diterpenoids as interleukin-1β inhibitors. Chinese Chem Lett 32:1475–1479. https://doi.org/10.1016/j.cclet.2020.09.048
Yang Z, Yin Y, Hu L (2009) Five New Cassane-Type Diterpenes from Caesalpinia crista widely distributed in tropical and subtropical regions of Southeast Asia. This plant is locally known as Ka-Lain in Myanmar, and its seeds are used as an anthelmintic, antipyretic, anti-inflamma. Helv Chim Acta 92:121–126
Yin Y, Ma L, Hu L (2008) Cassane-Type Diterpenoids from the Seeds of Caesalpinia magnifoliolata. Helv Chim Acta 91:972–977
Yodsaoue O, Karalai C, Ponglimanont C et al (2010) Potential anti-inflammatory diterpenoids from the roots of Caesalpinia mimosoides Lamk. Phytochemistry 71:1756–1764. https://doi.org/10.1016/j.phytochem.2010.06.016
Yodsaoue O, Karalai C, Ponglimanont C et al (2011) Pulcherrins D-R, potential anti-inflammatory diterpenoids from the roots of Caesalpinia pulcherrima. Tetrahedron 67:6838–6846. https://doi.org/10.1016/j.tet.2011.06.087
Yuanting J, Ruikang H, Yang L, Hanqiao L (2020) Two new cassane-type diterpenoids from the seeds of Caesalpinia sappan. Nat Prod Res. https://doi.org/10.1080/14786419.2020.1849196
Zanin JLB, Massoni M, Dos Santos MH et al (2015) Caesalpinioflavone, a new cytotoxic biflavonoid isolated from Caesalpinia pluviosa var. peltophoroides. J Braz Chem Soc 26:804–809. https://doi.org/10.5935/0103-5053.20150043
Zhang JY, Wu FH, Qu W, Liang JY (2012) Two new cassane diterpenoids from the seeds of Caesalpinia sappan Linn. Chin J Nat Med 10:218–221. https://doi.org/10.3724/SP.J.1009.2012.00218
Zhang JL, Tian HY, Chen NH et al (2014) Caesalpinimin A, a novel rearranged furanoditerpene with an unprecedented carbon skeleton from the seeds of Caesalpinia minax Hance. RSC Adv 4:7440–7443. https://doi.org/10.1039/c3ra46502k
Zhang J, Chen ZH, Xu J et al (2015a) New structures, chemotaxonomic significance and COX-2 inhibitory activities of cassane-type diterpenoids from the seeds of Caesalpinia minax. RSC Adv 5:76567–76574. https://doi.org/10.1039/c5ra14221k
Zhang JS, Guo YQ, Bao JM et al (2015b) Antioxidative Cassane Diterpenoids from the Seeds of Caesalpinia minax. Helv Chim Acta 98:1387–1394. https://doi.org/10.1002/hlca.201500230
Zhang P, Tang C, Yao S et al (2016) Cassane Diterpenoids from the Pericarps of Caesalpinia bonduc. J Nat Prod 79:24–29. https://doi.org/10.1021/acs.jnatprod.5b00520
Zhao P, Chen H, Wang H et al (2013) Four new cassane diterpenes from the seeds of Caesalpinia minax. Phytochem Lett 6:606–609. https://doi.org/10.1016/j.phytol.2013.07.013
Zhao H, Wang X, Li W et al (2014a) A new minor homoisoflavonoid from Caesalpinia sappan. Nat Prod Res 28:102–105. https://doi.org/10.1080/14786419.2013.847439
Zhao MB, Li J, Shi SP et al (2014b) Two new phenolic compounds from the heartwood of Caesalpinia sappan L. Molecules 19:1–8. https://doi.org/10.3390/molecules19010001
Zheng Y, Zhang SW, Cong HJ et al (2013) Caesalminaxins A-L, cassane diterpenoids from the seeds of Caesalpinia minax. J Nat Prod 76:2210–2218. https://doi.org/10.1021/np400545v
Zheng Y, Zhang SW, Xuan LJ (2015) Trinorcassane and cassane diterpenoids from the seeds of Caesalpinia minax. Fitoterapia 102:177–181. https://doi.org/10.1016/j.fitote.2015.03.006
Zheng J, Zhang S, Chen H et al (2020) Protosappanin-A and oleanolic acid protect injured podocytes from apoptosis through inhibition of AKT-mTOR signaling. Cell Biol Int 44:189–199. https://doi.org/10.1002/cbin.11218
Zhu NL, Sun ZH, Hu MG et al (2017a) New cassane diterpenoids from Caesalpinia sappan and their antiplasmodial activity. Molecules 22:1–7. https://doi.org/10.3390/molecules22101751
Zhu NL, Xu XD, Hu MG et al (2017b) Bioactive cassane diterpenoids from the seeds of Caesalpinia sappan. Phytochem Lett 22:113–116. https://doi.org/10.1016/j.phytol.2017.09.007
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The authors thank to CAPES (Conselho de Aperfeicioamento de Pessoal de Nível Superior) and CNPq-Conselho Nacional de Desenvolvimento Científico e Tecnológico (# 406427/2018-6) for the grants and scholarship.
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do Nascimento, B.O., David, J.M. Chemical composition, biological activities and traditional uses of plants from the segregated genus Caesalpinia sensu lato. Phytochem Rev 23, 1–93 (2024). https://doi.org/10.1007/s11101-023-09874-z
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DOI: https://doi.org/10.1007/s11101-023-09874-z