CC BY-NC-ND 4.0 · Planta Medica International Open 2019; 6(02): e50-e56
DOI: 10.1055/a-1006-2880
Original Papers
Eigentümer und Copyright ©Georg Thieme Verlag KG 2019

Melanin Production Inhibitors from the West African Cassipourea congoensis

Dieudonné M. Takou
1   Department of Chemistry, Faculty of Science, University of Douala, Douala, Cameroon
,
Alain F. Kamdem Waffo
1   Department of Chemistry, Faculty of Science, University of Douala, Douala, Cameroon
2   Department of Chemistry, Natural Products Research Group, Faculty of Engineering and Physical Sciences, University of Surrey, Guildford, United Kingdom
3   School of Chemistry and Physics, University of KwaZulu-Natal, Durban, South Africa
,
Moses K. Langat
2   Department of Chemistry, Natural Products Research Group, Faculty of Engineering and Physical Sciences, University of Surrey, Guildford, United Kingdom
5   Natural Capital and Plant Health Department, Jodrell Laboratory, Royal Botanic Gardens, Kew, Richmond, Surrey, United Kingdom
,
Jean D. Wansi
1   Department of Chemistry, Faculty of Science, University of Douala, Douala, Cameroon
,
Lauren E. Mulcahy-Ryan
4   School of Life Sciences, Pharmacy and Chemistry, Kingston University, London, Kingston, United Kingdom
,
Sianne L. Schwikkard
4   School of Life Sciences, Pharmacy and Chemistry, Kingston University, London, Kingston, United Kingdom
,
Elizabeth I. Opara
4   School of Life Sciences, Pharmacy and Chemistry, Kingston University, London, Kingston, United Kingdom
,
Eduard Mas-Claret
2   Department of Chemistry, Natural Products Research Group, Faculty of Engineering and Physical Sciences, University of Surrey, Guildford, United Kingdom
,
Dulcie A. Mulholland
2   Department of Chemistry, Natural Products Research Group, Faculty of Engineering and Physical Sciences, University of Surrey, Guildford, United Kingdom
3   School of Chemistry and Physics, University of KwaZulu-Natal, Durban, South Africa
› Author Affiliations
Further Information

Publication History

received 22 February 2019
revised 07 August 2019

accepted 26 August 2019

Publication Date:
01 October 2019 (online)

Abstract

Cassipourea congoensis (syn. Cassipourea malosana) is used in African countries as a skin-lightening agent. Two previously unreported cycloartane triterpenoids, 26-hydroxy-3-keto-24-methylenecycloartan-30-oic acid 1 and 24-methylenecycloartan-3β,26,30-triol 2 along with the known mahuannin B 3, 7-methoxymahuannin B 4, 7-methoxygeranin A 5, methyl-3-(4-hydroxy-3-methoxyphenyl)-2E-propenoate, glycerol-1-alkanoate, (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enal 6 , (-)-syringaresinol 7, and stigmast-5-en-3-O-β-D-glucoside, were isolated from the roots of C. congoensis. The crude extract and compounds 1 and 5 were found to inhibit the production of melanin at 10 µM with low cytotoxicity validating the ethnomedicinal use of this plant.

Supplementary Material

 
  • References

  • 1 Kanthraj GR. Skin-lightening agents: New chemical and plant extracts ongoing search for the holy grail!. Indian J Dermatol Venereol Leprol 2010; 76: 3-6
  • 2 Sheth VM, Pandya AG. Melasma: A comprehensive update: Part II. J Am Acad Dermatol 2011; 65: 699-714
  • 3 Olumide YM, Altraide D, Mohammed T, Ahamefule N, Ayanlowo S, Onyekonwu C, Essen N. Complications of chronic use of skin lightening cosmetics. Int J Dermatol 2008; 47: 344-353
  • 4 Findlay GH, Morrison JG, Simson IW. Exogenous ochronosis and pigmented colloid milium from hydroquinone bleaching creams. Br J Dermatol 1975; 93: 613-622
  • 5 Findlay GH, de Beer HA. Chronic hydroquinone poisoning of the skin from skin-lightening cosmetics. A South African epidemic of ochronosis of the face in dark-skinned individuals. S Afr Med J 1980; 57: 187-190
  • 6 Draelos ZD. Skin lightening preparations and the hydroquinone controversy. Dermatol Ther 2007; 20: 308-313
  • 7 Hardwick N, Van Gelder LW, Van der Merwe CA, Van der Merwe MP. Exogenous ochronosis: An epidemiological study. Br J Dermatol 1989; 120: 229-238
  • 8 Mulholland DA, Mwangi EM, Dlova NC, Plant N, Crouch NR, Coombes P. Non-toxic melanin production inhibitors from Garcinia livingstonei (Clusiaceae). J Ethnopharmacol 2013; 149: 570-575
  • 9 Burkill HM. The Useful Plants of West Tropical Africa. vol. 4 Kew: Royal Botanic Gardens; 1985
  • 10 Lewis J. Flora of Tropical East Africa. Kew: Royal Botanic Gardens 1956; 1
  • 11 Nkafamiya AJ, Manji AU, Umaru HA. Biochemical evaluation of Cassipourea congoensis (Tunti) and Nuclea latifolio (Luzzi) fruits. Afr. J Biotech 2006; 6: 2461-2463
  • 12 Williams VL, Raimondo D, Crouch NR, Cunningham AB, Scott-Shaw CR, Lotter M, Ngwenya AM. Cassipourea malosana (Baker) Alston. National Assessment: Red List of South African Plants. Version. 2014. Accessed on July 2, 2015 http://redlist.sanbi.org/species.php?species=1580-27
  • 13 Kato A, Okada M, Hashimoto Y. Occurrence of gerrardine in Cassipourea guianensis . J Nat Prod 1984; 47: 706-707
  • 14 Kato A, Okada M, Hashimoto Y. Sulfur-containing alkaloids from Cassipourea guianensis . J Nat Prod 1985; 48: 289-292
  • 15 Ichimaru M, Kato A, Hashimoto Y. Cassipoureamide-A and -B: New sulfur-containing amides from stem wood of Cassipourea guianensis . J Nat Prod 2000; 63: 1675-1676
  • 16 Chaturvedala VSP, Norris A, Miller JS, Ratovoson F, Andriantsiferana R, Rasamison VE, Kingston DGI. Cytotoxic diterpenes from Cassipourea madagascariensis from the Madagascar rainforest. J Nat Prod 2006; 69: 287-289
  • 17 Hou Y, Cao S, Brodie PJ, Miller JS, Birkinshaw C, Andrianafy MN, Andriantsiferana R, Rasamison VE, Ten Dyke K, Shen Y, Suh MS, Kingston DGI. Euphane triterpenoids of Cassipourea lanceolata from the Madagascar rainforest. Phytochem 2010; 71: 669-674
  • 18 Drewes SE, Taylor CW, Cunningham AB. (+)-Afzelechin 3-rhamnoside from Cassipourea gerrardii . Phytochem 1992; 31: 1073-1075
  • 19 Drewes SE, Taylor CW, Cunningham AB, Ferreira D, Steenkamp JA. Epiafzelechin-(4β→8, 2β→O→7)-ent-afzelechin from Cassipourea gerrardii . Phytochem 1992; 31: 2491-2494
  • 20 Drewes SE, Taylor CW. Methylated A-type proanthocyanidins and related metabolites from Cassipourea gummiflua . Phytochem 1994; 37: 551-555
  • 21 Nishiyama Y, Noda Y, Nakatani N, Shitan N, Sudo T, Kato A, Chalo Mutiso PB. Structure of constituents isolated from the bark of Cassipourea malosana and their cytotoxicity against a human ovarian cell line. J Nat Med 2018; 73: 289-296
  • 22 Pupo MT, Vieira PC, Fernandes JB, Da Silva MFF. A cycloartane triterpenoid and ώ-phenyl alkanoic and alkenoic acids from Trichilia claussenii . Phytochem 1996; 42: 795-798
  • 23 Anjaneyulu V, Satyanarayana P, Viswanadham KN, Jyothi VG, Nageswara R, Radhika P. Triterpenoids from Mangifera indica . Phytochem 1999; 50: 1229-1236
  • 24 Pillaiyar T, Manickam M, Namasivayam V. Skin whitening agents: Medicinal chemistry perspective of tyrosinase inhibitors. J Enzyme Inhib Med Chem 2017; 32: 403-425
  • 25 Chou ST, Chang WL, Chang CT, Hsu SL, Lin YC, Shih Y. Cinnamomum cassia essential oil inhibits α-MSH-induced melanin production and oxidative stress in murine B16 melanoma cells. Int J Mol Sci 2013; 14: 19186-19201
  • 26 Palumbo A, d’Ischia M, Misuraca G, Prota G. Mechanism of inhibition of melanogenesis by hydroquinone. Biochim Biophys Acta 1991; 1073: 85-90