Abstract
The present study provides an overview, focusing on the botanical aspects, phytochemistry, ethnopharmacology and biological activities reported for species from the tribe Vismieae (Hypericaceae). These species, traditionally distributed in three genera (Vismia, Psorospermum and Harungana), occur predominantly in tropical areas of South America, mainland Africa and Madagascar, where several of them are used in the traditional medicine mainly as febrifugal, antimalarial and for treating wounds of diverse origin. The phytochemical investigations indicated that the plants produce anthraquinones, anthrones, xanthones, benzophenones, flavonoids and some terpenoids. A number of 221 different compounds were obtained from 32 species of the tribe. Several compounds were investigated for the pharmacological activities, being cytotoxic and antimicrobial the most cited. Nevertheless, a number of pharmacological researches were carried out with extracts and some findings experimentally evidenced the ethnopharmacological usefulness of several species. The distribution of the anthracenic derivatives, xanthones and benzophenone precursors is not uniform in the genera. Thus, the substitution pattern of these compounds was analyzed and the systematic relationship among the taxa is discussed in the light of these features. Of note, more species need chemical investigation in order to make a judgment about the taxonomic significance of the compounds, but it seems that, although the tribe has a certain homogeneity, each genus has particularities. Considering this statement, it is possible to say that in the chemical point of view, Psorospermum is diferent from Harungana and both are diferent from Vismia, which is clearly separate into two distinct groups, the African and the American species.
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Abbreviations
- ABTS:
-
2,2′-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)
- AchE:
-
Acetylcholinesterase
- BchE:
-
Butyrylcholinesterase
- CC50 :
-
Concentration causing 50% reduction of cell viability (CC = cytotoxic concentration)
- CCl4 :
-
Carbon tetrachloride
- CUPRAC:
-
Cupric reducing antioxidant capacity
- DPPH:
-
2,2-Diphenyl-1-picrylhydrazyl
- ED50/EC50 :
-
Median effective dose for 50% of the group
- Fe (II):
-
Iron in its + 2 oxidation state
- FRAP:
-
Ferric reducing antioxidant power
- GC–MS:
-
Gas Chromatography – Mass Spectrometry
- GI50 :
-
Concentration causing 50% cell growth inhibition
- GOT:
-
Glutamic oxaloacetic transaminase
- GPT:
-
Glutamic pyruvic transaminase
- H2O2 − :
-
Hydrogen peroxide radical
- HSV-1:
-
Herpes simplex virus type 1
- IC50 :
-
Half maximal inhibitory concentration to inhibit 50%
- KB:
-
Keratin-forming tumor
- LC50 :
-
Concentration causing 50% cell death (LC = lethal concentration)
- MDA:
-
Malondialdehyde
- MIC:
-
Minimum inhibitory concentration
- NO− :
-
Nitric oxide
- O2 − :
-
Superoxide radical
- OH− :
-
Hydroxyl radical
- ONOO− :
-
Peroxynitrite
- ORAC:
-
Oxygen radical absorbance capacity
- TBARS:
-
Thiobarbituric acid reactive substances
- TNF-α :
-
Tumour necrosis factor alpha
- WHO:
-
World Health Organization
References
Abou-Shoer M, Boettner FE, Chang CJ, Cassady JM (1988) Antitumour and cytotoxic xanthones of Psorospermum febrifugum. Phytochemistry 27:2795–2800. https://doi.org/10.1016/0031-9422(88)80665-4
Abou-Shoer M, Habib AA, Chang CJ, Cassady JM (1989a) Seven xanthonolignoids from Psorospermum febrifugum. Phytochemistry 28:2483–2487. https://doi.org/10.1016/S0031-9422(00)98010-5
Abou-shoer M, Suwanborirux K, Chang C, Cassady JM (1989b) Novel tetrahydrofurobenzofuranoxanthones from Psorospermum febrifugum. Tetrahedron Lett 30:3385–3388. https://doi.org/10.1016/S0040-4039(00)99251-7
Abou-Shoer M, Suwanborirux K, Habib AAM et al (1993) Xanthones and vismiones from Psorospermum febrifugum. Phytochemistry 34:1413–1420. https://doi.org/10.1016/0031-9422(91)80040-8
Adelodun VO, Elusiyan CA, Olorunmola FO et al (2013) Evaluation of antitrypanosomal and anti inflammatory activities of selected Nigerian medicinal plants in mice. Afr J Tradit Complement Altern Med 10:469–476. https://doi.org/10.4314/ajtcam.v10i6.13
Adeneye AA, Olagunju JA, Benebo AS et al (2008a) Nephroprotective effects of the aqueous root extract of Harungana madagascariensis (L.) in acute and repeated dose acetaminophen renal injured rats. Int J Appl Res Nat Prod 1:6–14
Adeneye AA, Olagunju JA, Elias SO et al (2008b) Protective activities of the aqueous root extract of Harungana madagascariensis in acute and repeated acetaminophen hepatotoxic rats. Int J Appl Res Nat Prod 1:29–42. https://doi.org/10.1055/s-0028-1084157
Agbor GA, Kuate D, Oben JE (2007) Medicinal plants can be good source of antioxidants: case study in Cameroon. Pak J Biol Sci 10:537–544. https://doi.org/10.3923/pjbs.2007.537.544
Ahua KM, Ioset JR, Ioset KN et al (2007) Antileishmanial activities associated with plants used in the Malian traditional medicine. J Ethnopharmacol 110:99–104. https://doi.org/10.1016/j.jep.2006.09.030
Akah PA (1994) Abortifacient activity of some Nigerian medicinal plants. Phyther Res 8:106–108. https://doi.org/10.1002/ptr.2650080212
Álvarez RE, Jímenez GO, Posada AC et al (2008) Actividad antioxidante y contenido fenólico de los extractos provenientes de las bayas de dos especies del género Vismia (Guttiferae). Vitae (Medellín) 15:165–172
Amonkar A, Chang C, Cassady JM (1981) 6-Geranyloxy-3-methyl-1,8-dihydroxyanthrone, a novel antileukemic agent from Psorospermum febrifugum Sprach var. ferrugineum (Hook. fil). Experientia 37:1138–1139. https://doi.org/10.1007/BF01989881
Antia BS, Ita BN, Udo UE (2015) Nutrient composition and in vitro antioxidant properties of Harungana madagascariensis stem bark extracts. J Med Food 18:609–614. https://doi.org/10.1089/jmf.2014.0084
Anywar G, Kakudidi E, Byamukama R et al (2020) Indigenous traditional knowledge of medicinal plants used by herbalists in treating opportunistic infections among people living with HIV/AIDS in Uganda. J Ethnopharmacol 246:112205. https://doi.org/10.1016/j.jep.2019.112205
APG IV (2016) An update of the Angiosperm Phylogeny Group classification for the orders and families of flowering plants: APG IV. Bot J Linn Soc 181:1–20. https://doi.org/10.1111/boj.12385
Aronson NE, Magill AJ (2020) Protozoal infections: general principles. In: Ryan ET, Hill DR, Solomon T et al (eds) Hunter’s tropical medicine and emerging infectious diseases, 10th edn. Elsevier, Amsterdam, pp 696–698
Asogwa FC, Ibezim A, Ntie-Kang F et al (2020) Anti-psoriatic and immunomodulatory evaluation of Psorospermum febrifugum Spach and its phytochemicals. Sci African 7:e00229. https://doi.org/10.1016/j.sciaf.2019.e00229
Baider C, Florens FBV (2011) Control of invasive alien weeds averts imminent plant extinction. Biol Invasions 13:2641–2646. https://doi.org/10.1007/s10530-011-9980-3
Baldi A, Gehrmann B, Romani A, Vincieri F (1992) Polyphenols from Harungana madagascariensis. Planta Med 58:691–692. https://doi.org/10.1055/s-2006-961711
Ballard CG (2002) Advances in the treatment of Alzheimer’s disease: benefits of dual cholinesterase inhibition. Eur Neurol 47:64–70. https://doi.org/10.1159/000047952
Bamps P (1966) Notes sur les Guttiferae d’Afrique tropicale. Bull du Jard Bot l’État a Bruxelles 36:425. https://doi.org/10.2307/3667181
Bennett GJ, Lee HH (1989) Xanthones from Guttiferae. Phytochemistry 28:967–998. https://doi.org/10.1016/0031-9422(89)80170-0
Betti JL, Lejoly J (2009) Contribution to the knowledge of medicinal plants of the Dja biosphere reserve, Cameroon: plants used for treating jaundice. J Med Plants Res 3:1056–1065
Biapa NPC, Oben JE, Ngogang JY (2011) Scavenging radical kinetic and antianaemic screening properties of some medicinal plants used in Cameroon. Int J Appl Res Nat Prod 4:29–36
Biapa PCN, Agbor GA, Oben JE, Ngogang JY (2007) Phytochemical studies and antioxidant properties of four medicinal plants used in Cameroon. Afr J Tradit Complement Altern Med 4:495–500. https://doi.org/10.4314/ajtcam.v4i4.31243
Biapa PCN, Matei H, Bâlici Ş et al (2013) Protective effects of stem bark of Harungana madgascariensis on the red blood cell membrane. BMC Complement Altern Med. https://doi.org/10.1186/1472-6882-13-98
Bilia AR, Yusuf AW, Braca A et al (2000) New prenylated anthraquinones and xanthones from Vismia guineensis. J Nat Prod 63:16–21. https://doi.org/10.1021/np990226j
Bongomin F, Gago S, Oladele RO, Denning DW (2017) Global and multi-national prevalence of fungal diseases—estimate precision. J Fungi. https://doi.org/10.3390/jof3040057
Botta B, Delle Monache F, Delle Monache G et al (1983) 3-Geranyloxy-6-methyl-1,8-dihydroxyanthraquinone and vismiones C, D and E from Psorospermum febrifugum. Phytochemistry 22:539–542. https://doi.org/10.1016/0031-9422(83)83041-6
Botta B, Delle Monache F, Delle Monache G et al (1985) Prenylated bianthrones and vismione F from Psorospermum febrifugum. Phytochem 24:827–830. https://doi.org/10.1016/S0031-9422(00)84902-X
Botta B, Delle Monache F, Delle Monache G (1987) A novel type of prenylated anthranoid from Psorospermum glaberrimum. Tetrahedron Lett 28:567–570. https://doi.org/10.1016/S0040-4039(00)95783-6
Botta B, Delle Monache F, Delle Monache G, Kabangu K (1986a) Acetylvismione D from Psorospermum febrifugum. Phytochemistry 25:766. https://doi.org/10.1016/0031-9422(86)88048-7
Botta B, Delle Monache F, Delle Monache G, Menichini F (1988) Psorolactones and other metabolites from Psorospermum glaberrimum. ChemInform 20:6–11. https://doi.org/10.1002/chin.198914325
Botta B, Delle Monache G, Delle Monache F et al (1986b) Vismione H and prenylated xanthones from Vismia guineensis. Phytochemistry 25:1217–1219. https://doi.org/10.1016/S0031-9422(00)81583-6
Buckley D, Ritchie E, Taylor W, Young L (1972) Madagascarin, a new pigment from the leaves of Harungana madagascariensis. Aust J Chem 25:843. https://doi.org/10.1071/CH9720843
Buitrago A, Rojas J, Rojas L et al (2015) Essential oil composition and antimicrobial activity of Vismia macrophylla leaves and fruits collected in Táchira-Venezuela. Nat Prod Commun 10:375–377. https://doi.org/10.1177/1934578x1501000244
Camele G, Monache FD, Monache GD et al (1982) 2-Isoprenylemodin and 5,5′-dimethoxysesamin from Vismia guaramirangae. Phytochemistry 21:417–419. https://doi.org/10.1016/S0031-9422(00)95279-8
Cassinelli G, Geroni C, Botta B et al (1986) Cytotoxic and antitumor activity of vismiones isolated from Vismieae. J Nat Prod 49:929–931. https://doi.org/10.1021/np50047a031
CDC (2020) Centers for disease control and prevention. https://www.cdc.gov/
Chen W, Jia Z, Pan MH, Anandh Babu PV (2016) Natural products for the prevention of oxidative stress-related diseases: mechanisms and strategies. Oxid Med Cell Longev 2016:2–4. https://doi.org/10.1155/2016/4628502
Chisté RC, Ribeiro AB, Berto A et al (2014) Vismia cauliflora extracts: bioactive compounds and the in vitro scavenging capacity against reactive oxygen and nitrogen species. Free Radic Biol Med 75:S26. https://doi.org/10.1016/j.freeradbiomed.2014.10.748
Christenhusz MMJ, Fay MF, Byng JW (2018) The global flora, a practical guide to vascular plant species of the world. Plant Gateway, Bradford
Costa M, Silva A, Silva A et al (2017) Essential oils from leaves of medicinal plants of Brazilian flora: chemical composition and activity against Candida species. Medicines 4:27. https://doi.org/10.3390/medicines4020027
Crockett SL, Robson NKB (2011) Taxonomy and chemotaxonomy of the genus Hypericum. Med Aromat Plant Sci Biotechnol 5:1–13
Cronquist A (1981) An integrated system of classification of flowering plants. Columbia University Press, New York
de Albuquerque UP, Monteiro JM, Ramos MA, de Amorim ELC (2007) Medicinal and magic plants from a public market in northeastern Brazil. J Ethnopharmacol 110:76–91. https://doi.org/10.1016/j.jep.2006.09.010
Delle Monache F, Botta B, Monache GD, Bettolo GBM (1985) Prenylated anthranoids from Psorospermum species. Phytochemistry 24:1855–1856. https://doi.org/10.1016/S0031-9422(00)82572-8
Delle Monache F, Ferrari F, Bettolo GBM, Cuca Suarez LE (1980a) Chemistry of the genus Vismia. IV: Deacetylvismione A and vismin. Planta Med 40:340–346. https://doi.org/10.1055/s-2008-1074982
Delle Monache F, Mac-Quhae MM, Monache GD et al (1983) Xanthones, xanthonolignoids and other constituents of the roots of Vismia guaramirangae. Phytochemistry 22:227–232. https://doi.org/10.1016/S0031-9422(00)80095-3
Delle Monache F, Mc Quhae MM, Ferrari F, Marini-Bettolo GB (1979) Ferruginin A and B and ferruanthrone, new triprenylated anthranoids from Vismia baccifera var. ferruginea. Tetrahedron 35:2143–2149. https://doi.org/10.1016/0040-4020(79)87031-3
Delle Monache F, Torres FF, Marini-Bettolo GB, De Lima RA (1980b) Chemistry of Vismia genus. Note V: γ-hydroxy and γ, γ’-dihydroxy-ferruginin A. J Nat Prod 43:487–494. https://doi.org/10.1021/np50010a009
Delle Monache G, Delle Monache F, Di Benedetto R, Oguakwa JU (1987) Chemistry of the Psorospermum genus. Part 5. New metabolites from Psorospermum tenuifolium. Phytochemistry 26:2611–2613. https://doi.org/10.1016/S0031-9422(00)83889-3
Delle Monache G, Gonzalez JG, Delle Monache F, Bettolo GBM (1980c) Prenylated benzophenones from Vismia decipiens. Phytochemistry 19:2025–2028. https://doi.org/10.1016/0031-9422(80)83030-5
Díaz AB, Vera JR, Cote V et al (2010) NMR elucidation and crystal structure analysis of 1-hydroxy-3,6-dimethoxy-8-methyl-9h-xanthen-9-one (lichexanthone) isolated from Vismia baccifera (Guttiferae). Boletín Latinoam y del Caribe Plantas Med y Aromáticas 9:470–474
Dimmer J, Cabral FV, Sabino CP et al (2019) Natural anthraquinones as novel photosentizers for antiparasitic photodynamic inactivation. Phytomedicine 61:152894. https://doi.org/10.1016/j.phymed.2019.152894
Doriguetto AC, Santos MH, Ellena JA, Nagem TJ (2001) 6-Deoxyjacareubin. Acta Crystallogr Sect C Cryst Struct Commun 57:1095–1097. https://doi.org/10.1107/S0108270101009246
dos Santos MH, Nagem TJ, Da Silva MC, Silva E, LGF, (2000a) Xanthones from Vismia latifolia. J Braz Chem Soc 11:537–539. https://doi.org/10.1590/s0103-50532000000500017
Dos Santos MH, Nagem TJ, Fonseca E Silva LG, Da Silva MC (2000b) Total assignment of 1H and 13C NMR spectra of a prenylated oxanthrone from Vismia latifolia. Magn Reson Chem 38:1027–1030
Dressler S, Schmidt M, Zizka G (2014) (continously updated) African Plants—A Photo Guide. Forschungsinstitut Senckenberg, Frankfurt/Main, Germany. http://www.africanplants.senckenberg.de. Accessed Sept 2020
Engler A (1893) Guttiferae. In: Engler A, Prantl K (eds) Die natürlichen Pflanzenfamilien. W. Engelmann, Berlin, pp 194–242
Epifano F, Fiorito S, Genovese S (2013) Phytochemistry and pharmacognosy of the genus Psorospermum. Phytochem Rev 12:673–684. https://doi.org/10.1007/s11101-013-9274-8
Epifano F, Genovese S, Menghini L, Curini M (2007) Chemistry and pharmacology of oxyprenylated secondary plant metabolites. Phytochemistry 68:939–953. https://doi.org/10.1016/j.phytochem.2007.01.019
Estevez Y, Castillo D, Pisango MT et al (2007) Evaluation of the leishmanicidal activity of plants used by Peruvian Chayahuita ethnic group. J Ethnopharmacol 114:254–259. https://doi.org/10.1016/j.jep.2007.08.007
Etame RME, Mouokeu RS, Ngane RAN et al (2017) Acute and sub-acute toxicity of Harungana madagascariensis LAM (Hypericaceae) stem bark methanol extract. J Appl Pharm Sci 7:160–167. https://doi.org/10.7324/JAPS.2017.70326
François G, Steenackers T, Assi LA et al (1999) Vismione H and structurally related anthranoid compounds of natural and synthetic origin as promising drugs against the human malaria parasite Plasmodium falciparum: Structure-activity relationships. Parasitol Res 85:582–588. https://doi.org/10.1007/s004360050598
Fuller RW, Westergaard CK, Collins JW et al (1999) Vismiaphenones D-G, new prenylated benzophenones from Vismia cayennensis. J Nat Prod 62:67–69. https://doi.org/10.1021/np980152w
Fundação Rede Amazônica (2012) Conheça as propriedades medicinais da árvore lacre. AmazonSat, Manaus
Gbolade AA, Tira-Picos V, Nogueira JMF, Oladele AT (2009) Comparative analysis of essential oils from the leaf, fruit and stem bark of Harungana madagascariensis. Int J Green Pharm 3:290–292. https://doi.org/10.4103/0973-8258.59734
Gessler MC, Tanner M, Chollet J et al (1995) Tanzanian medicinal plants used traditionally for the treatment of malaria: In vivo antimalarial and in vitro cytotoxic activities. Phyther Res 9:504–508. https://doi.org/10.1002/ptr.2650090708
Gómez-Cansino R, Espitia-Pinzon CI, Campos-Lara MG et al (2015) Antimycobacterial and HIV-1 reverse transcriptase activity of Julianaceae and Clusiaceae plant species from Mexico. Evidence-based Complement Altern Med. https://doi.org/10.1155/2015/183036
Gonçalves MDLS, Mors WB (1981) Vismiaquinone, a Δ1-isopentenyl substituted anthraquinone from Vismia reichardtiana. Phytochemistry 20:1947–1950. https://doi.org/10.1016/0031-9422(81)84041-1
Gonzales Gonzales J, Delle Monache F, Delle Monache G, Marini Bettolo G (1980) Chemistry of the genus Vismia. Planta Med 40:347–350. https://doi.org/10.1055/s-2008-1074983
Gundogdu G, Gundogdu K, Nalci KA et al (2019) The effect of parietin isolated from Rheum ribes L. on in vitro wound model using human dermal fibroblast cells. Int J Low Extrem Wounds 18:56–64. https://doi.org/10.1177/1534734618819660
Gurib-Fakim A (2006) Medicinal plants: traditions of yesterday and drugs of tomorrow. Mol Aspects Med 27:1–93. https://doi.org/10.1016/j.mam.2005.07.008
Gustafsson MHG, Bittrich V, Stevens PF (2002) Phylogeny of Clusiaceae based on rbcL sequences. Int J Plant Sci 163:1045–1054. https://doi.org/10.1086/342521
Habib AM, Ho DK, Masuda S et al (1987a) Structure and stereochemistry of psorospermin and related cytotoxic dihydrofuranoxanthones from Psorospermum febrifugum. J Org Chem 52:412–418. https://doi.org/10.1021/jo00379a018
Habib AM, Reddy KS, McCloud TG et al (1987b) New xanthones from Psorospermum febrifugum. J Nat Prod 50:141–145. https://doi.org/10.1021/np50050a001
Hamill FA, Apio S, Mubiru NK et al (2003) Traditional herbal drugs of Southern Uganda, II: literature analysis and antimicrobial assays. J Ethnopharmacol 84:57–78. https://doi.org/10.1016/S0378-8741(02)00289-1
Happi GM, Tiani GLM, Gbetnkom BYM et al (2020) Phytochemistry and pharmacology of Harungana madagascariensis: mini review. Phytochem Lett 35:103–112. https://doi.org/10.1016/j.phytol.2019.11.015
Hernández-Pasteur G, Silva-Bermúdez PS, Reyes-Chilpa R et al (2019) In vitro evaluation of the healing and antimicrobial activity of extracts of Buddleja cordata Kunth and Vismia baccifera (L.) Triana and Planch. Rev Fitotec Mex 42:93–99. https://doi.org/10.35196/rfm.2019.2.93-99
Huerta-Reyes M, Basualdo MDC, Lozada L et al (2004) HIV-1 inhibition by extracts of Clusiaceae species from Mexico. Biol Pharm Bull 27:916–920. https://doi.org/10.1248/bpb.27.916
Hussain H, Hussain J, Al-Harrasi A et al (2012) Chemistry and biology of genus Vismia. Pharm Biol 50:1448–1462. https://doi.org/10.3109/13880209.2012.680972
Hussein AA, Bozzi B, Correa M et al (2003) Bioactive constituents from three Vismia species. J Nat Prod 66:858–860. https://doi.org/10.1021/np020566w
Iinuma M, Tosa H, Ito T et al (1995) Two prenylated anthrones in Harungana madagascariensis. Phytochemistry 40:267–270. https://doi.org/10.1016/0031-9422(95)00202-I
Iinuma M, Tosa H, Tanaka T et al (1996) Occurrence of xanthonolignoids in Guttifereous plants. Heterocycles 43:1521. https://doi.org/10.3987/COM-96-7497
Iwalewa EO, Adewale IO, Taiwo BJ et al (2008a) Effects of Harungana madagascariensis stem bark extract on the antioxidant markers in alloxan induced diabetic and carrageenan induced inflammatory disorders in rats. J Complement Integr Med. https://doi.org/10.2202/1553-3840.1088
Iwalewa EO, Naidoo V, Bagla V, Eloff JN (2009a) Nitric oxide producing effect of six extracts from Harungana madagascariensis Lam. ex Poiret (Guttiferae) stem bark. Afr J Pharm Pharmacol 3:014–021
Iwalewa EO, Omisore NO, Adewunmi CO et al (2008b) Anti-protozoan activities of Harungana madagascariensis stem bark extract on trichomonads and malaria. J Ethnopharmacol 117:507–511. https://doi.org/10.1016/j.jep.2008.02.019
Iwalewa EO, Omisore NO, Daniyan OM et al (2009b) Elemental compositions and anti-anemic property of Harungana madagascariensis stem bark. Bangladesh J Pharmacol 4:115–121. https://doi.org/10.3329/bjp.v4i2.1641
Iwalewa EO, Suleiman MM, Mdee LK, Eloff JN (2009c) Antifungal and antibacterial activities of different extracts of Harungana madagascariensis stem bark. Pharm Biol 47:878–885. https://doi.org/10.1080/13880200903029316
Jansen O, Angenot L, Tits M et al (2010) Evaluation of 13 selected medicinal plants from Burkina Faso for their antiplasmodial properties. J Ethnopharmacol 130:143–150. https://doi.org/10.1016/j.jep.2010.04.032
Johnson OO, Zhao M, Gunn J et al (2016) α-Glucosidase inhibitory prenylated anthranols from Harungana madagascariensis. J Nat Prod 79:224–229. https://doi.org/10.1021/acs.jnatprod.5b00924
Kemegne GA, Mkounga P, Essia Ngang JJ et al (2017) Antimicrobial structure activity relationship of five anthraquinones of emodine type isolated from Vismia laurentii. BMC Microbiol 17:1–8. https://doi.org/10.1186/s12866-017-0954-1
Kengni F, Fodouop SPC, Tala DS et al (2016) Antityphoid properties and toxicity evaluation of Harungana madagascariensis Lam (Hypericaceae) aqueous leaf extract. J Ethnopharmacol 179:137–145. https://doi.org/10.1016/j.jep.2015.12.037
Kengni F, Tala D, Djimeli M et al (2013) In vitro antimicrobial activity of Harungana madagascriensis and Euphorbia prostrata extracts against some pathogenic Salmonella sp. Int J Biol Chem Sci 7:1106. https://doi.org/10.4314/ijbcs.v7i3.17
Kerharo J, Adam JG (1974) The traditional Senegalese pharmacopoeia, medicinal and toxic plants. Vigot brothers, Paris
Kisangau DP, Hosea KM, Joseph CC, Lyaruu HVM (2007) In vitro antimicrobial assay of plants used in traditional medicine in Bukoba Rural District, Tanzania. Afr J Tradit Complement Altern Med 4:510–523. https://doi.org/10.4314/ajtcam.v4i4.31245
Koffi AJ, Bla KB, Yapi HF et al (2015) Phytochemical screening of some medicinal plants in Côte D’ivoire and evaluation of their extraction efficiency. Int J Pharmacogn Phytochem Res 7:563–569
Konan Y, Witabouna KM, Bassirou B, Kagoyire K (2014) Antioxidant activity and total phenolic content of nine plants from Côte d’Ivoire (West Africa). J Appl Pharm Sci 4:36–41. https://doi.org/10.7324/JAPS.2014.40807
Koné WM, Koffi AG, Bomisso EL, Tra Bi FH (2012) Ethnomedical study and iron content of some medicinal herbs used in traditional medicine in Cote d’Ivoire for the treatment of anaemia. Afr J Tradit Complement Altern Med. https://doi.org/10.4314/ajtcam.v9i1.12
Kouam SF, Khan SN, Krohn K et al (2006) α-glucosidase inhibitory anthranols, kenganthranols A-C, from the stem bark of Harungana madagascariensis. J Nat Prod 69:229–233. https://doi.org/10.1021/np050407n
Kouam SF, Ngadjui BT, Krohn K et al (2005) Prenylated anthronoid antioxidants from the stem bark of Harungana madagascariensis. Phytochemistry 66:1174–1179. https://doi.org/10.1016/j.phytochem.2005.03.022
Kouam SF, Njonkou YLN, Kuigoua GM et al (2010) Psorantin, a unique methylene linked dimer of vismin and kenganthranol E, two anthranoid derivatives from the fruits of Psorospermum aurantiacum (Hypericaceae). Phytochem Lett 3:185–189. https://doi.org/10.1016/j.phytol.2010.07.003
Kouam SF, Yapna DB, Krohn K et al (2007) Antimicrobial prenylated anthracene derivatives from the leaves of Harungana madagascariensis. J Nat Prod 70:600–603. https://doi.org/10.1021/np060556l
Kuete V, Nguemeving JR, Beng VP et al (2007) Antimicrobial activity of the methanolic extracts and compounds from Vismia laurentii De Wild (Guttiferae). J Ethnopharmacol 109:372–379. https://doi.org/10.1016/j.jep.2006.07.044
Kuete V, Wabo HK, Eyong KO et al (2011) Anticancer activities of six selected natural compounds of some Cameroonian medicinal plants. PLoS ONE 6:4–10. https://doi.org/10.1371/journal.pone.0021762
Kupchan SM, Streelman DR, Sneden AT (1980) Psorospermin, a new antileukemic xanthone from Psorospermum febrifugum. J Nat Prod 43:296–301. https://doi.org/10.1021/np50008a010
Lamorde M, Tabuti JRS, Obua C et al (2010) Medicinal plants used by traditional medicine practitioners for the treatment of HIV/AIDS and related conditions in Uganda. J Ethnopharmacol 130:43–53. https://doi.org/10.1016/j.jep.2010.04.004
Leet JE, Liu X, Drexler DM et al (2008) Cytotoxic xanthones from Psorospermum molluscum from the Madagascar Rain Forest. J Nat Prod 71:460–463. https://doi.org/10.1021/np070523l
Lenta BN, Devkota KP, Ngouela S et al (2008) Anti-plasmodial and cholinesterase inhibiting activities of some constituents of Psorospermum glaberrimum. Chem Pharm Bull 56:222–226. https://doi.org/10.1248/cpb.56.222
Lenta BN, Ngouela S, Fekam Boyom F et al (2007a) Anti-plasmodial activity of some constituents of the root bark of Harungana madagascariensis LAM. (Hypericaceae). Chem Pharm Bull 55:464–467. https://doi.org/10.1248/cpb.55.464
Lenta BN, Vonthron-Sénécheau C, Fongang Soh R et al (2007b) In vitro antiprotozoal activities and cytotoxicity of some selected Cameroonian medicinal plants. J Ethnopharmacol 111:8–12. https://doi.org/10.1016/j.jep.2006.10.036
Leu Y-L, Hwang T-L, Hu J-W, Fang J-Y (2008) Anthraquinones from Polygonum cuspidatum as tyrosinase inhibitors for dermal use. Phyther Res 22:552–556. https://doi.org/10.1002/ptr.2324
Li CY, Lee EJ, Wu TS (2004) Antityrosinase principles and constituents of the petals of Crocus sativus. J Nat Prod 67:437–440. https://doi.org/10.1021/np0302854
Lins ACS, Agra MF, Conceição DCO et al (2016) Chemical constituents and antioxidant activity from aerial parts of Clusia paralicola and Vismia guianensis. Rev Virtual Quim 8:157–168. https://doi.org/10.5935/1984-6835.20160011
Lizcano LJ, Siles M, Trepiana J et al (2015) Piper and Vismia species from Colombian Amazonia differentially affect cell proliferation of hepatocarcinoma cells. Nutrients 7:179–195. https://doi.org/10.3390/nu7010179
Lizcano LJ, Viloria-Bernal M, Vicente F et al (2012) Lipid oxidation inhibitory effects and phenolic composition of aqueous extracts from medicinal plants of Colombian Amazonia. Int J Mol Sci 13:5454–5467. https://doi.org/10.3390/ijms13055454
Llorent-Martinez EJ, Ruiz-Riaguas A, Sinan KI et al (2020) Exploring chemical profiles and bioactivities of Harungana madagascariensis Lam. ex Poir. leaves and stem bark extracts: a new source of procyanidins. Anal Lett 53:399–412. https://doi.org/10.1080/00032719.2019.1653903
Lopez A, Hudson JB, Towers GHN (2001) Antiviral and antimicrobial activities of Colombian medicinal plants. J Ethnopharmacol 77:189–196. https://doi.org/10.1016/S0378-8741(01)00292-6
Lozano R, Naghavi M, Foreman K et al (2012) Global and regional mortality from 235 causes of death for 20 age groups in 1990 and 2010: a systematic analysis for the Global Burden of Disease Study 2010. Lancet 380:2095–2128. https://doi.org/10.1016/S0140-6736(12)61728-0
Madsen P, Westergaard N (2001) Glucose-6-phosphatase inhibitors for the treatment of Type 2 diabetes. Expert Opin Ther Pat 11:1429–1441. https://doi.org/10.1517/13543776.11.9.1429
Madubunyi II, Obi SKC, Nwebube NI, Chime AB (1995) Antihepatotoxic and antimicrobial activities of Harungana madagascariensis leaf extracts. Int J Pharmacogn 33:129–134. https://doi.org/10.3109/13880209509055212
Malan DF, Neuba DFR, Kouakou KL (2015) Medicinal plants and traditional healing practices in Ehotile people, around the Aby Lagoon (eastern littoral of Côte d’Ivoire). J Ethnobiol Ethnomed 11:1–18. https://doi.org/10.1186/s13002-015-0004-8
Manjia JN, Njayou FN, Joshi A et al (2019) The anti-aging potential of medicinal plants in Cameroon: Harungana madagascariensis Lam. and Psorospermum aurantiacum Engl. prevent in vitro ultraviolet B light-induced skin damage. Eur J Integr Med 29:100925. https://doi.org/10.1016/j.eujim.2019.05.011
Manya MH, Keymeulen F, Ngezahayo J et al (2020) Antimalarial herbal remedies of Bukavu and Uvira areas in DR Congo: an ethnobotanical survey. J Ethnopharmacol 249:112422. https://doi.org/10.1016/j.jep.2019.112422
Marinho LC, Martins MV, Amorim AM, Bittrich V (2016) Vismia atlantica (Hypericaceae), a new species previously thought to be well-known from the Brazilian Atlantic Forest. J Torrey Bot Soc 143:330–337. https://doi.org/10.3159/TORREY-D-15-00041
Marston A, Chapuis JC, Sordat B et al (1986) Anthracenic derivatives from Psorospermum febrifugum and their in vitro cytotoxicities to a human colon carcinoma cell line. Planta Med NO 3:207–210. https://doi.org/10.1055/s-2007-969124
Martínez y Pérez JL, Castillo-Campos G (2008) Hypericaceae. In: Gomez-Pompa A (ed) Flora de Veracruz. UNAM, Mexico, pp 1–40
Martins MV, Shimizu GH, Bittrich V (2018a) Flora da Reserva Ducke, Estado do Amazonas, Brasil: Hypericaceae. Hoehnea 45:361–371. https://doi.org/10.1590/2236-8906-13/2018
Martins MV, Shimizu GH, Bittrich V, Do Amaral MDCE (2018b) Vismia conduplicata (Hypericaceae), a new species from Mato Grosso Brazil. Phytotaxa 338:125–129. https://doi.org/10.11646/phytotaxa.338.1.11
Mbwambo ZH, Apers S, Moshi MJ et al (2004) Anthranoid compounds with antiprotozoal activity from Vismia orientalis. Planta Med 70:706–710. https://doi.org/10.1055/s-2004-827199
Ménan H, Banzouzi JT, Hocquette A et al (2006) Antiplasmodial activity and cytotoxicity of plants used in West African traditional medicine for the treatment of malaria. J Ethnopharmacol 105:131–136. https://doi.org/10.1016/j.jep.2005.10.027
Mesquita RDCG, Massoca PEDS, Jakovac CC et al (2015) Amazon rain forest succession: stochasticity or land-use legacy? Bioscience 65:849–861. https://doi.org/10.1093/biosci/biv108
Miraglia MDC, Mesquita AAL, de Jesus M et al (1981) Anthraquinones from Vismia species. Phytochemistry 20:2041–2042. https://doi.org/10.1016/0031-9422(81)84067-8
Molander M, Nielsen L, Søgaard S et al (2014) Hyaluronidase, phospholipase A2 and protease inhibitory activity of plants used in traditional treatment of snakebite-induced tissue necrosis in Mali, DR Congo and South Africa. J Ethnopharmacol 157:171–180. https://doi.org/10.1016/j.jep.2014.09.027
Monteiro J, Dondeyne S, Wursten B et al (2011) Vegetation composition of natural gaps in Moribane forest (Mozambique). Afr J Ecol 49:510–514. https://doi.org/10.1111/j.1365-2028.2011.01281.x
Moshi MJ, Mbwambo ZH, Masimba PJ et al (2006) Evaluation of ethnomedical claims and brine shrimp toxicity of some plants used in Tanzania as traditional medicines. Cancer 3:48–58
Moulari B, Lboutounne H, Pellequer Y et al (2005) Vectorization of Harungana madagascariensis Lam. ex Poir. (Hypericaceae) ethanolic leaf extract by using PLG-nanoparticles: Antibacterial activity assessment. Drug Dev Res 65:26–33. https://doi.org/10.1002/ddr.20004
Moulari B, Pellequer Y, Chaumont JP et al (2007) In vitro antimicrobial activity of the leaf extract of Harungana madagascariensis lam. ex Poir. (Hypericaceae) against strains causing otitis externa in dogs and cats. Acta Vet Hung 55:97–105. https://doi.org/10.1556/AVet.55.2007.1.10
Moulari B, Pellequer Y, Lboutounne H et al (2006) Isolation and in vitro antibacterial activity of astilbin, the bioactive flavanone from the leaves of Harungana madagascariensis Lam. ex Poir. (Hypericaceae). J Ethnopharmacol 106:272–278. https://doi.org/10.1016/j.jep.2006.01.008
Mpiana PT, Makelele LK, Oleko RW et al (2010) Antisickling activity of medicinal plants used in the management of sickle cell disease in the Tshopo district, DR Congo. Aust J Med Herbal 22:132–137
Mpiana PT, Mudogo V, Tshibangu DST et al (2008) Antisickling activity of anthocyanins from Bombax pentadrum, Ficus capensis and Ziziphus mucronata: Photodegradation effect. J Ethnopharmacol 120:413–418. https://doi.org/10.1016/j.jep.2008.09.012
Muganza DM, Fruth BI, Nzunzu Lami J et al (2012) In vitro antiprotozoal and cytotoxic activity of 33 ethonopharmacologically selected medicinal plants from Democratic Republic of Congo. J Ethnopharmacol 141:301–308. https://doi.org/10.1016/j.jep.2012.02.035
Mukungu N, Abuga K, Okalebo F et al (2016) Medicinal plants used for management of malaria among the Luhya community of Kakamega East sub-County, Kenya. J Ethnopharmacol 194:98–107. https://doi.org/10.1016/j.jep.2016.08.050
Muthaura CN, Rukunga GM, Chhabra SC et al (2007) Traditional antimalarial phytotherapy remedies used by the Kwale community of the Kenyan Coast. J Ethnopharmacol 114:377–386. https://doi.org/10.1016/j.jep.2007.08.033
Nagem TJ, de Oliveira FF (1997) Xanthones and other constituents of Vismia parviflora. J Braz Chem Soc 8:505–508. https://doi.org/10.1590/S0103-50531997000500011
Nagem TJ, de Jesus Faria T (1990) Quinonoid and other constituents of Vismia martiana. Phytochemistry 29:3362–3364. https://doi.org/10.1016/0031-9422(90)80218-6
Nguemeving JR, Azebaze AGB, Kuete V et al (2006) Laurentixanthones A and B, antimicrobial xanthones from Vismia laurentii. Phytochemistry 67:1341–1346. https://doi.org/10.1016/j.phytochem.2006.03.018
Nguta JM, Mbaria JM, Gathumbi PK et al (2011) Ethnodiagnostic skills of the Digo community for malaria: a lead to traditional bioprospecting. Front Pharmacol. https://doi.org/10.3389/fphar.2011.00030
Nguyen HT, Lallemand MC, Boutefnouchet S et al (2009) Antitumor Psoropermum xanthones and sarcomelicope acridones: Privileged structures implied in DNA alkylation. J Nat Prod 72:527–539. https://doi.org/10.1021/np800644y
Nku-Ekpang Okot-Asi T, Uwagie-Ero Edwin A, Beshel Favour N et al (2018) Protective role of Harungana madagascariensis Lam. ex Poir. (Hypericaceae) ethanol leave extract on hematology and serum protein levels in phenylhydrazine-induced anaemia. Pharmacologyonline 2:161–170
Noumi E, Fozi FL (2003) Ethnomedical botany of epilepsy treatment in Fongo-Tongo village, Western Province, Cameroon. Pharm Biol 41:330–339. https://doi.org/10.1076/phbi.41.5.330.15944
Noumi E, Yomi A (2001) Medicinal plants used for intestinal diseases in Mbalmayo Region, Central Province, Cameroon. Fitoterapia 72:246–254. https://doi.org/10.1016/S0367-326X(00)00288-4
Noungoue DT, Antheaume C, Chaabi M et al (2008) Anthraquinones from the fruits of Vismia laurentii. Phytochemistry 69:1024–1028. https://doi.org/10.1016/j.phytochem.2007.10.026
Noungoue DT, Chaabi M, Ngouela S et al (2009) Antimalarial compounds from the stem bark of Vismia laurentii. Zeitschrift fur Naturforsch Sect C J Biosci 64:210–214. https://doi.org/10.1515/znc-2009-3-410
Noungoue DT, Lenta BN, Lobstein A et al (2007) Tirucalla-7,24-dien-3-one. Acta Crystallogr Sect E Struct Reports Online. https://doi.org/10.1107/S1600536807012949
Nwaehuj CO, Ode JO, Akande MG (2013) In vitro antioxidant potentials of some herbal plants from Southern Nigeria. J Med Sci 13:56–61. https://doi.org/10.3923/jms.2013.56.61
Nwodo OFC (1989) Antibiotic and anti-inflammatory analgesic activities of Harungana madagascariensis stem bark. Pharm Biol 27:137–140. https://doi.org/10.3109/13880208909053953
Nyamukuru A, Tabuti JRS, Lamorde M et al (2017) Medicinal plants and traditional treatment practices used in the management of HIV/AIDS clients in Mpigi District, Uganda. J Herb Med 7:51–58. https://doi.org/10.1016/j.hermed.2016.10.001
Oboh G, Akomolafe TL, Adefegha SA, Adetuyi AO (2010) Antioxidant and modulatory effect of ethanolic extract of Madagascar Harungana (Harungana madagascariensis) bark on cyclophosphamide induced neurotoxicity in rats. J Food Drug Anal 18:171–179. https://doi.org/10.38212/2224-6614.2265
Ochwang’i DO, Kimwele CN, Oduma JA et al (2014) Medicinal plants used in treatment and management of cancer in Kakamega County, Kenya. J Ethnopharmacol 151:1040–1055. https://doi.org/10.1016/j.jep.2013.11.051
Ochwang’i DO, Kimwele CN, Oduma JA et al (2018) Cytotoxic activity of medicinal plants of the Kakamega County (Kenya) against drug-sensitive and multidrug-resistant cancer cells. J Ethnopharmacol 215:233–240. https://doi.org/10.1016/j.jep.2018.01.004
Okoli AS, Okeke MI, Iroegbu CU, Ebo PU (2002) Antibacterial activity of Harungana madagascariensis leaf extracts. Phyther Res 16:174–179. https://doi.org/10.1002/ptr.991
Olagunju JA, Ogunfeibo AB, Ogunbosi AO, Taiwo OA (2004) Biochemical changes elicited by isosaline leaf and stem-bark extracts of Harungana madagascariensis in the rat. Phyther Res 18:588–591. https://doi.org/10.1002/ptr.978
Oliveira AH, de Oliveira GG, Carnevale Neto F et al (2017) Anti-inflammatory activity of Vismia guianensis (Aubl.) Pers. extracts and antifungal activity against Sporothrix schenckii. J Ethnopharmacol 195:266. https://doi.org/10.1016/j.jep.2016.11.030
Onajobi IB, Adhikari A, Hussain S et al (2016) New α-glucosidase inhibiting anthracenone from the barks of Harungana madagascariensis Lam. Nat Prod Res 30:2507–2513. https://doi.org/10.1080/14786419.2015.1115998
Pachuta RR, Cooks RG, Cassady JM et al (1986) Antineoplastic agents from higher plants: application of tandem mass spectrometry to xanthones from Psorospermum febrifugum. J Nat Prod 49:412–423. https://doi.org/10.1021/np50045a005
Pedersen ME, Vestergaard HT, Hansen SL et al (2009) Pharmacological screening of Malian medicinal plants used against epilepsy and convulsions. J Ethnopharmacol 121:472–475. https://doi.org/10.1016/j.jep.2008.11.006
Pinheiro RM, Mac-Quhae MM, Bettolo GBM, Monache FD (1984) Prenylated anthranoids from Vismia species. Phytochemistry 23:1737–1740. https://doi.org/10.1016/S0031-9422(00)83481-0
Politi M, Sanogo R, Ndjoko K et al (2004) HPLC-UV/PAD and HPLC-MSn analyses of leaf and root extracts of Vismia guineensis and bianthrones. Phytochem Anal Int J Plant Chem Biochem Tech 364:355–364
Poumale HMP, Randrianasolo R, Rakotoarimanga JV et al (2008) Flavonoid glycosides and other constituents of Psorospermum androsaemifolium Baker (Clusiaceae). Chem Pharm Bull 56:1428–1430. https://doi.org/10.1248/cpb.56.1428
Poumale PHM, Krebs HC, Amadou D et al (2011) Flavonol glycoside from Psorospermum androsaemifolium. Chin J Chem 29:85–88. https://doi.org/10.1002/cjoc.201190065
Queiroz EF, Ahua KM, Hostettmann K (2005) Investigation of medicinal plants for the treatment of neglected diseases. Chimia (Aarau) 59:299–302. https://doi.org/10.2533/000942905777676353
Radha KS, Madhyastha HK, Nakajima Y et al (2008) Emodin upregulates urokinase plasminogen activator, plasminogen activator inhibitor-1 and promotes wound healing in human fibroblasts. Vascul Pharmacol 48:184–190. https://doi.org/10.1016/j.vph.2008.02.002
Ramathal DC, Ngassapa OD (2001) Medicinal plants used by Rwandese traditional healers in refugee camps in Tanzania. Pharm Biol 39:132–137. https://doi.org/10.1076/phbi.39.2.132.6251
Ranarivelo HS (2017) Systematics, biogeography, and species delimitation of the malagasy Psorospermum (Hypericaceae). University of Missouri, Missouri
Rayan A, Raiyn J, Falah M (2017) Nature is the best source of anticancer drugs: indexing natural products for their anticancer bioactivity. PLoS ONE 12:1–12. https://doi.org/10.1371/journal.pone.0187925
Reyes-Chilpa R, Gómez-Cansino R, Guzmán-Gutiérrez SL et al (2014) Anthraquinones from Vismia mexicana. Zeitschrift fur Naturforsch Sect C J Biosci 69C:29–34. https://doi.org/10.5560/ZNC.2013-0038
Ribeiro AB, Berto A, Chisté RC et al (2015a) Bioactive compounds and scavenging capacity of extracts from different parts of Vismia cauliflora against reactive oxygen and nitrogen species. Pharm Biol 53:1267–1276. https://doi.org/10.3109/13880209.2014.974063
Ribeiro AB, Berto A, Ribeiro D et al (2015b) Stem bark and flower extracts of Vismia cauliflora are highly effective antioxidants to human blood cells by preventing oxidative burst in neutrophils and oxidative damage in erythrocytes. Pharm Biol 53:1691–1698. https://doi.org/10.3109/13880209.2014.1001407
Ribeiro AB, Berto A, Ribeiro D et al (2014) Stem bark and flower extracts of Vismia cauliflora: modulation of oxidative burst in human neutrophils’ and inhibition of oxidative damage in human erythrocytes. Free Radic Biol Med 75:S45–S46. https://doi.org/10.1016/j.freeradbiomed.2014.10.805
Ribeiro RV, Bieski IGC, Balogun SO, Martins DTO (2017) Ethnobotanical study of medicinal plants used by Ribeirinhos in the North Araguaia microregion, Mato Grosso, Brazil. J Ethnopharmacol 205:69–102. https://doi.org/10.1016/j.jep.2017.04.023
Ritchie E, Taylor WC (1964) The constituents of Harungana madagascariensis Poir. Tetrahedron Lett 5:1431–1436. https://doi.org/10.1016/S0040-4039(01)89507-1
Robson NKB (2016) And then came molecular phylogenetics: reactions to a monographic study of Hypericum (Hypericaceae). Phytotaxa 255:181–198. https://doi.org/10.11646/phytotaxa.255.3.1
Robson NKB (2012) Studies in the genus Hypericum L. (Hypericaceae) 9. Addenda, corrigenda, keys, lists and general discussion
Rodríguez M, Hasegawa M, González-Mújica F et al (2008) Antidiabetic and antiradical activities of plants from Venezuelan Amazon. Braz J Pharmacogn 18:331–338. https://doi.org/10.1590/S0102-695X2008000300004
Roger T, Pierre-Marie M, Igor VK, Patrick VD (2015) Phytochemical screening and antibacterial activity of medicinal plants used to treat typhoid fever in Bamboutos division, West Cameroon. J Appl Pharm Sci 5:034–049. https://doi.org/10.7324/JAPS.2015.50606
Rojas J, Buitrago A, Rojas L et al (2011a) Essential oil composition and antibacteral activity of Vismia baccifera fruits collected from Mérida, Venezuela. Nat Prod Commun 6:699–700. https://doi.org/10.1177/1934578x1100600525
Rojas J, Buitrago A, Rojas L, Morales A (2011b) Essential oil composition of Vismia macrophylla leaves (Guttiferae). Nat Prod Commun 6:85–86. https://doi.org/10.1177/1934578x1100600120
Roumy V, Ruiz Macedo JC, Bonneau N et al (2020) Plant therapy in the Peruvian Amazon (Loreto) in case of infectious diseases and its antimicrobial evaluation. J Ethnopharmacol 249:112411. https://doi.org/10.1016/j.jep.2019.112411
Ruhfel BR, Bittrich V, Bove CP et al (2011) Phylogeny of the clusioid clade (Malpighiales): evidence from the plastid and mitochondrial genomes. Am J Bot 98:306–325. https://doi.org/10.3732/ajb.1000354
Ruhfel BR, Stevens PF, Davis CC (2013) Combined morphological and molecular phylogeny of the clusioid clade (Malpighiales) and the placement of the ancient rosid macrofossil paleoclusia. Int J Plant Sci 174:910–936. https://doi.org/10.1086/670668
Salas F, Velasco J, Rojas J, Morales A (2007) Antibacterial activity of the crude extract and constituents of Vismia baccifera var. dealbata (Guttiferae) collected in Venezuela. Nat Prod Commun. https://doi.org/10.1177/1934578X0700200216
Santana WEL, Nunez CV, Moya HD (2015) Antioxidant activity and polyphenol content of some Brazilian medicinal plants exploiting the formation of the Fe(II)/2,2’-bipyridine complexes. Nat Prod Commun 10:1821–1824
Schultz F, Anywar G, Wack B et al (2020) Ethnobotanical study of selected medicinal plants traditionally used in the rural Greater Mpigi region of Uganda. J Ethnopharmacol 256:112742. https://doi.org/10.1016/j.jep.2020.112742
Seo EK, Wani MC, Wall ME et al (2000) New bioactive aromatic compounds from Vismia guianensis. Phytochemistry 55:35–42. https://doi.org/10.1016/S0031-9422(00)00208-9
Stevens PF (2007) Hypericaceae. In: Kubitzki K (ed), The families and genera of vascular plants. Flowering plants. Eudicots: Berberidopsidales, Buxales, Crossosomatales, Fabales pp., Geraniales, Gunnerales, Myrtales p.p., Proteales, Saxifragales, Vitales, Zygophyllales, Clusiaceae alliance, Passifloraceae. Springer, Berlin, pp 194–201
Stout GH, Alden RA, Kraut J, High DF (1962) Harunganin: a crystallographic determination of an unknown structure. J Am Chem Soc 84:2653–2654. https://doi.org/10.1021/ja00872a045
Suffredini IB, Paciencia MLB, Frana SA et al (2007a) In vitro breast cancer cell lethality of Brazilian plant extracts. Pharmazie 62:798–800. https://doi.org/10.1691/ph.2007.10.6767
Suffredini IB, Paciencia MLB, Varella AD, Younes RN (2007b) In vitro cytotoxic activity of Brazilian plant extracts against human lung, colon and CNS solid cancers and leukemia. Fitoterapia 78:223–226. https://doi.org/10.1016/j.fitote.2006.11.011
Tala MF, Krohn K, Hussain H et al (2007) Laurentixanthone C: a new antifungal and algicidal xanthone from stem bark of Vismia laurentii. Zeitschrift fur Naturforsch Sect B J Chem Sci 62:565–568. https://doi.org/10.1515/znb-2007-0413
Tala MF, Talontsi FM, Wabo HK et al (2013) Anthraquinones and triterpenoids from seeds of Vismia guineensis. Biochem Syst Ecol 50:310–312. https://doi.org/10.1016/j.bse.2013.04.014
Tamokou JD, Chouna JR, Fischer-Fodor E et al (2013) Anticancer and antimicrobial activities of some antioxidant-rich Cameroonian medicinal plants. PLoS ONE. https://doi.org/10.1371/journal.pone.0055880
Tamokou JDD, Tala MF, Wabo HK et al (2009) Antimicrobial activities of methanol extract and compounds from stem bark of Vismia rubescens. J Ethnopharmacol 124:571–575. https://doi.org/10.1016/j.jep.2009.04.062
Tanemossu SAF, Franke K, Schmidt J, Wessjohann L (2015) Chemical constituents of Psorospermum densipunctatum (Hypericaceae). Biochem Syst Ecol 59:174–176. https://doi.org/10.1016/j.bse.2015.01.018
Tankeo SB, Damen F, Sandjo LP et al (2016) Antibacterial activities of the methanol extracts, fractions and compounds from Harungana madagascariensis Lam. ex Poir. (Hypericaceae). J Ethnopharmacol 190:100–105. https://doi.org/10.1016/j.jep.2016.06.005
Tchakam PD, Lunga PK, Kowa TK et al (2012) Antimicrobial and antioxidant activities of the extracts and compounds from the leaves of Psorospermum aurantiacum Engl. and Hypericum lanceolatum Lam. BMC Complement Altern Med. https://doi.org/10.1186/1472-6882-12-136
Tchamo DN, Brelot L, Antheaume C et al (2008) Methyl 5,7-dihydr-oxy-2,2,9-trimethyl-6,11-dioxo-6,11-dihydro-2H-anthra[2, 3-b]pyran-8-carboxyl-ate. Acta Crystallogr Sect E Struct Reports Online. https://doi.org/10.1107/S160053680803794X
Thomson RH (1991) Distribution of naturally occurring quinones. Pharm Weekbl 13:70–73
Tiani GM, Ahmed I, Krohn K et al (2013) Kenganthranol f, a new anthranol from Psorospermum aurantiacum. Nat Prod Commun 8:103–104. https://doi.org/10.1177/1934578x1300800123
Tih AE, Ghogomu RT, Sondengam BL et al (2006) Minor constituents of Harungana madagascariensis stem bark. Biochem Syst Ecol 34:267–269. https://doi.org/10.1016/j.bse.2005.08.004
Tona L, Kambu K, Ngimbi N et al (1998) Antiamoebic and phytochemical screening of some Congolese medicinal plants. J Ethnopharmacol 61:57–65. https://doi.org/10.1016/S0378-8741(98)00015-4
Tona L, Kambu K, Ngimbi N et al (2000) Antiamoebic and spasmolytic activities of extracts from some antidiarrhoeal traditional preparations used in Kinshasa, Congo. Phytomedicine 7:31–38. https://doi.org/10.1016/S0944-7113(00)80019-7
Traore MS, Baldé MA, Diallo MST et al (2013) Ethnobotanical survey on medicinal plants used by Guinean traditional healers in the treatment of malaria. J Ethnopharmacol 150:1145–1153. https://doi.org/10.1016/j.jep.2013.10.048
Traore MS, Diane S, Diallo MST et al (2014) In vitro antiprotozoal and cytotoxic activity of ethnopharmacologically selected Guinean plants. Planta Med 80:1340–1344. https://doi.org/10.1055/s-0034-1383047
Trepiana J, Ruiz-Larrea MB, Ruiz-Sanz JI (2018) Unraveling the in vitro antitumor activity of Vismia baccifera against HepG2: role of hydrogen peroxide. Heliyon. https://doi.org/10.1016/j.heliyon.2018.e00675
Tsaffack M, Nguemeving JR, Kuete V et al (2009) Two new antimicrobial dimeric compounds: febrifuquinone, a vismione-anthraquinone coupled pigment and adamabianthrone, from two Psorospermum species. Chem Pharm Bull 57:1113–1118. https://doi.org/10.1248/cpb.57.1113
Viza Junior G, Guimarães M, Baptista A, Baptista A (2019) Plantas medicinaise leshimaniose cutânea: Uma revisão. Rev Cereus 11:84–98. https://doi.org/10.18605/2175-7275/cereus.v11n4p84-98
Vizcaya M, Morales A, Rojas J, Nuñez R (2012) A review on the chemical composition and pharmacological activities of Vismia genus (Guttiferae). Bol Latinoam y del Caribe Plantas Med y Aromat 11:12–34
Vogel Ely C, de Loreto Bordignon SA, Iob Boldrini I (2020a) Clarifying the nomenclature of non-Andean South American Hypericum (Hypericaceae). Taxon 69:593–604. https://doi.org/10.1002/tax.12234
Vogel Ely C, Shimizu GH, Martins MV, Marinho LC (2020b) Hypericaceae. In: Flora do Bras. 2020 em construção. http://floradobrasil.jbrj.gov.br/reflora/floradobrasil/FB133. Accessed 19 Aug 2020
Wabo HK, Kouam SF, Krohn K et al (2007) Prenylated anthraquinones and other constituents from the seeds of Vismia laurentii. Chem Pharm Bull 55:1640–1642. https://doi.org/10.1248/cpb.55.1640
WHO (2020) World Health Organization. https://www.who.int/
Wiegrebe W, Müller K (1995) Treatment of psoriasis with anthrones: chemical principles, biochemical aspects, and approaches to the design of novel derivatives. Skin Pharmacol Physiol 8:1–24. https://doi.org/10.1159/000211326
Willcox M, Sanogo R, Diakite C et al (2012) Improved traditional medicines in Mali. J Altern Complement Med 18:212–220. https://doi.org/10.1089/acm.2011.0640
Zubair MF, Oladosu IA, Olawore NO et al (2011) Bioactive steroid from the root bark of Psorospermum corymbiferum. Chin J Nat Med 9:264–266. https://doi.org/10.1016/S1875-5364(11)60062-9
Zubair MF, Oladosu IA, Olawore NO (2010) Chemical composition of the leaf oil of Psorospermum corymbiferum Hochr. growing in Africa. J Essent Oil Res 22:529–530. https://doi.org/10.1080/10412905.2010.9700390
Acknowledgements
The authors would like to thank Cleusa Vogel Ely and Lucas Cardoso Marinho, specialists in Hypericaceae systematics, for their assistance with the botanical aspects addressed in this review. The authors also thank Heritiana Ranarivelo, Matthew Walters and Lucas Cardoso Marinho for allowing the use of photographs of the plants. This work was supported by financial contributions of Brazilian agencies FAPERGS, CAPES and CNPq.
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KAPD, HB and GCM contributed to literature searching and data collection in addition to the manuscript preparation and revision. GLP contributed to the study concepts and design, as well as manuscript preparation and revision. All the authors discussed, edited and approved the final version.
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Diel, K.A.P., de Carvalho Meirelles, G., Bridi, H. et al. Drawing a parallel between phytochemistry and other features of Vismieae species. Phytochem Rev 20, 1109–1159 (2021). https://doi.org/10.1007/s11101-021-09740-w
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DOI: https://doi.org/10.1007/s11101-021-09740-w