Skip to main content
Top
Published in: Journal of Natural Medicines 4/2017

01-10-2017 | Original Paper

Triterpenoid saponins from Polaskia chichipe Backbg. and their inhibitory or promotional effects on the melanogenesis of B16 melanoma cells

Authors: Koji Fujihara, Kunio Takahashi, Kiyotaka Koyama, Kaoru Kinoshita

Published in: Journal of Natural Medicines | Issue 4/2017

Login to get access

Abstract

Five new oleanane-type saponins 15 together with a known saponin 6 and a steroidal glycoside 7 were isolated from Polaskia chichipe Backbg., and their structures were determined from their 1D and 2D NMR and HRFABMS spectral data. The six isolated saponins 16 were tested for their effects on the melanogenesis of B16 melanoma 4A5 cells. Compound 1 exerted an inhibitory effect at 100 μM whereas compound 3 promoted melanogenesis at the same concentration, even though these two compounds contain the same aglycon structure. The dose-dependent activities of compounds 1 and 3 on melanin synthesis were investigated.
Appendix
Available only for authorised users
Literature
1.
go back to reference Djerassi C, Geller LE, Lemin AJ (1953) Terpenoids. I. The triterpenes of the cactus Lemaireocereus thurberi. J Am Chem Soc 75:2254–2256CrossRef Djerassi C, Geller LE, Lemin AJ (1953) Terpenoids. I. The triterpenes of the cactus Lemaireocereus thurberi. J Am Chem Soc 75:2254–2256CrossRef
2.
go back to reference Djerassi C, McDonald RM, Lemin AJ (1953) Terpenoids. III. The isolation of erythrodiol, oleanolic acid and a new triterpene triol, longispinogenin, from the cactus Lemaireocereus longispinus. J Am Chem Soc 75:5940–5942CrossRef Djerassi C, McDonald RM, Lemin AJ (1953) Terpenoids. III. The isolation of erythrodiol, oleanolic acid and a new triterpene triol, longispinogenin, from the cactus Lemaireocereus longispinus. J Am Chem Soc 75:5940–5942CrossRef
3.
go back to reference Djerassi C, Farkas E, Lemin AJ, Collins JC, Walls F (1954) Terpenoids. VI. Dumortierigenin, a new triterpene lactone from the cactus Lemaireocereus dumortieri. J Am Chem Soc 76:2969–2973CrossRef Djerassi C, Farkas E, Lemin AJ, Collins JC, Walls F (1954) Terpenoids. VI. Dumortierigenin, a new triterpene lactone from the cactus Lemaireocereus dumortieri. J Am Chem Soc 76:2969–2973CrossRef
4.
go back to reference Djerassi C, Geller LE, Lemin AJ (1954) Terpenoids. VIII. The structures of the cactus triterpenes gummosogenin and longispinogenin. J Am Chem Soc 76:4089–4091CrossRef Djerassi C, Geller LE, Lemin AJ (1954) Terpenoids. VIII. The structures of the cactus triterpenes gummosogenin and longispinogenin. J Am Chem Soc 76:4089–4091CrossRef
5.
go back to reference Djerassi C, Farkas E, Liu LH, Thomas GH (1955) Terpenoids. XVII. The cactus triterpenes thurberogenin and stellatogenin. J Am Chem Soc 77:5330–5336CrossRef Djerassi C, Farkas E, Liu LH, Thomas GH (1955) Terpenoids. XVII. The cactus triterpenes thurberogenin and stellatogenin. J Am Chem Soc 77:5330–5336CrossRef
6.
go back to reference Djerassi C, Henry JA, Lemin AJ, Rios T, Thomas GH (1956) Terpenoids. XXIV. The structures of the cactus triterpene queretaroic acid. J Am Chem Soc 78:3783–3787CrossRef Djerassi C, Henry JA, Lemin AJ, Rios T, Thomas GH (1956) Terpenoids. XXIV. The structures of the cactus triterpene queretaroic acid. J Am Chem Soc 78:3783–3787CrossRef
7.
go back to reference Djerassi C, Robinson CH, Thomas DB (1956) Terpenoids. XXV. The structures of the cactus triterpene dumortierigenin. J Am Chem Soc 78:5685–5691CrossRef Djerassi C, Robinson CH, Thomas DB (1956) Terpenoids. XXV. The structures of the cactus triterpene dumortierigenin. J Am Chem Soc 78:5685–5691CrossRef
8.
go back to reference Djerassi C, Burstein S, Estrada H, Lemin AJ, Lippman AE, Manjarrez A, Monsimer HG (1957) Terpenoids. XXVIII. The triterpene composition of the genus Myrtillocactus. J Am Chem Soc 79:3525–3528CrossRef Djerassi C, Burstein S, Estrada H, Lemin AJ, Lippman AE, Manjarrez A, Monsimer HG (1957) Terpenoids. XXVIII. The triterpene composition of the genus Myrtillocactus. J Am Chem Soc 79:3525–3528CrossRef
9.
go back to reference Sandoval A, Manjarrez A, Leeming PR, Thomas GH, Djerassi C (1957) Terpenoids. XXX. The structure of the cactus triterpene chichipegenin. J Am Chem Soc 79:4468–4472CrossRef Sandoval A, Manjarrez A, Leeming PR, Thomas GH, Djerassi C (1957) Terpenoids. XXX. The structure of the cactus triterpene chichipegenin. J Am Chem Soc 79:4468–4472CrossRef
10.
go back to reference Sahu NP, Banerji N, Chakravarti RN (1974) A new saponin of oleanolic acid from Pereskia grandifolia. Phytochemistry 13:529–530CrossRef Sahu NP, Banerji N, Chakravarti RN (1974) A new saponin of oleanolic acid from Pereskia grandifolia. Phytochemistry 13:529–530CrossRef
11.
go back to reference Khong PW, Lewis KG (1975) New triterpenoids extractives from Lemaireocereus chichipe. Aust J Chem 28:165–172CrossRef Khong PW, Lewis KG (1975) New triterpenoids extractives from Lemaireocereus chichipe. Aust J Chem 28:165–172CrossRef
12.
go back to reference Kinoshita K, Koyama K, Takahashi K, Kondo N, Yuasa H (1992) New triterpenes from Trichocereus bridgesii. J Nat Prod 55:953–955CrossRef Kinoshita K, Koyama K, Takahashi K, Kondo N, Yuasa H (1992) New triterpenes from Trichocereus bridgesii. J Nat Prod 55:953–955CrossRef
13.
go back to reference Takizawa T, Kinoshita K, Koyama K, Takahashi K, Kondo N, Yuasa H (1993) A new type of triterpene from Trichocereus pachanoi. J Nat Prod 56:2183–2185CrossRef Takizawa T, Kinoshita K, Koyama K, Takahashi K, Kondo N, Yuasa H (1993) A new type of triterpene from Trichocereus pachanoi. J Nat Prod 56:2183–2185CrossRef
14.
go back to reference Koyama K, Yama T, Kinoshita K, Takahashi K, Kondo N, Yuasa H (1993) New triterpenes from cactaceous plants. J Nat Prod 56:2201–2203CrossRef Koyama K, Yama T, Kinoshita K, Takahashi K, Kondo N, Yuasa H (1993) New triterpenes from cactaceous plants. J Nat Prod 56:2201–2203CrossRef
15.
go back to reference Kinoshita K, Takizawa T, Koyama K, Takahashi K, Kondo N, Yuasa H (1995) New triterpenes from Trichocereus pachanoi. J Nat Prod 58:1739–1744CrossRef Kinoshita K, Takizawa T, Koyama K, Takahashi K, Kondo N, Yuasa H (1995) New triterpenes from Trichocereus pachanoi. J Nat Prod 58:1739–1744CrossRef
16.
go back to reference Yang Y, Kinoshita K, Koyama K, Takahashi K, Kondo N, Yuasa H (1998) New triterpenes from Machaerocereus eruca. J Nat Prod 61:456–460CrossRef Yang Y, Kinoshita K, Koyama K, Takahashi K, Kondo N, Yuasa H (1998) New triterpenes from Machaerocereus eruca. J Nat Prod 61:456–460CrossRef
17.
go back to reference Kinoshita K, Koyama K, Takahashi K, Kondo N, Yuasa H (2000) A new triterpenoid saponin from Isolatocereus dumortieri. J Nat Prod 63:701–703CrossRef Kinoshita K, Koyama K, Takahashi K, Kondo N, Yuasa H (2000) A new triterpenoid saponin from Isolatocereus dumortieri. J Nat Prod 63:701–703CrossRef
18.
go back to reference Imai T, Okazaki S, Kinoshita K, Koyama K, Takahashi K, Yuasa H (2006) Triterpenoid saponins from cultural plants of Stenocereus stellatus (Cactaceae). J Nat Prod 60:49–53 Imai T, Okazaki S, Kinoshita K, Koyama K, Takahashi K, Yuasa H (2006) Triterpenoid saponins from cultural plants of Stenocereus stellatus (Cactaceae). J Nat Prod 60:49–53
19.
go back to reference Okazaki S, Kinoshita K, Koyama K, Takahashi K, Yuasa H (2007) New triterpenoid saponins from Stenocereus eruca (Cactaceae). J Nat Med 61:24–29CrossRef Okazaki S, Kinoshita K, Koyama K, Takahashi K, Yuasa H (2007) New triterpenoid saponins from Stenocereus eruca (Cactaceae). J Nat Med 61:24–29CrossRef
20.
go back to reference Okazaki S, Kinoshita K, Ito S, Koyama K, Yuasa H, Takahashi K (2011) Triterpenoid saponins from Echinopsis macrogona (Cactaceae). Phytochemistry 72:136–146CrossRef Okazaki S, Kinoshita K, Ito S, Koyama K, Yuasa H, Takahashi K (2011) Triterpenoid saponins from Echinopsis macrogona (Cactaceae). Phytochemistry 72:136–146CrossRef
21.
go back to reference Kakuta K, Koike T, Kinoshita K, Ito S, Koyama K, Takahashi K (2012) New triterpenoid saponins from Stenocereus eruca. Heterocycles 85:1377–1392CrossRef Kakuta K, Koike T, Kinoshita K, Ito S, Koyama K, Takahashi K (2012) New triterpenoid saponins from Stenocereus eruca. Heterocycles 85:1377–1392CrossRef
22.
go back to reference Kinoshita K, Akiba M, Koyama K, Takahashi K, Kondo N, Yuasa H (1998) Antinociceptive effect of triterpenes from cacti. Pharm Biol 36:50–57CrossRef Kinoshita K, Akiba M, Koyama K, Takahashi K, Kondo N, Yuasa H (1998) Antinociceptive effect of triterpenes from cacti. Pharm Biol 36:50–57CrossRef
23.
go back to reference Kinoshita K, Koyama K, Takahashi K, Nishino H (1999) Inhibitory effect of some triterpenes from cacti on 32Pi-incorporation into phospholipids of HeLa cells promoted by 12-O-tetradecanoylphorbol-13-acetate. Phytomedicine 6:73–77CrossRef Kinoshita K, Koyama K, Takahashi K, Nishino H (1999) Inhibitory effect of some triterpenes from cacti on 32Pi-incorporation into phospholipids of HeLa cells promoted by 12-O-tetradecanoylphorbol-13-acetate. Phytomedicine 6:73–77CrossRef
24.
go back to reference Kakuta K, Baba M, Ito S, Kinoshita K, Koyama K, Takahashi K (2012) New triterpenoid saponins from cacti and anti-type I allergy activity of saponins from cactus. Bioorg Med Chem Lett 22:4793–4800CrossRef Kakuta K, Baba M, Ito S, Kinoshita K, Koyama K, Takahashi K (2012) New triterpenoid saponins from cacti and anti-type I allergy activity of saponins from cactus. Bioorg Med Chem Lett 22:4793–4800CrossRef
25.
go back to reference Harinantenaina L, Brodie PJ, Callmander MW, Razafitsalama LJ, Rasamison VE, Rakotobe E, Kingston DGI (2012) Two antiproliferative saponins of Tarenna grevei from the Madagascar dry forest. Nat Prod Commun 7:705–708 Harinantenaina L, Brodie PJ, Callmander MW, Razafitsalama LJ, Rasamison VE, Rakotobe E, Kingston DGI (2012) Two antiproliferative saponins of Tarenna grevei from the Madagascar dry forest. Nat Prod Commun 7:705–708
26.
go back to reference Ma R-J, Liu Z-H, Dong F-W, Li J-Y, Zi C-T, Gao W, Yang L, Zhou J, Hu J-M (2016) Oleanane-type triterpene saponins from Hydrocotyle nepalensis. Fitoterapia 110:66–71CrossRef Ma R-J, Liu Z-H, Dong F-W, Li J-Y, Zi C-T, Gao W, Yang L, Zhou J, Hu J-M (2016) Oleanane-type triterpene saponins from Hydrocotyle nepalensis. Fitoterapia 110:66–71CrossRef
27.
go back to reference Yoshikawa K, Taninaka H, Kan Y, Arihara S (1994) Antisweet natural products. X. Structures of sitakisosides I–V from Stephanotis lutchuensis KOIDZ. var. japonica. Chem Pharm Bull 42:2023–2027 Yoshikawa K, Taninaka H, Kan Y, Arihara S (1994) Antisweet natural products. X. Structures of sitakisosides I–V from Stephanotis lutchuensis KOIDZ. var. japonica. Chem Pharm Bull 42:2023–2027
28.
go back to reference Hambley WT, Lewis GK, Tucker JD, Turner P (1996) Properties of olean-12-ene-3β,16β,22α,28-tetrol and some derivatives. Aust J Chem 49:775–783CrossRef Hambley WT, Lewis GK, Tucker JD, Turner P (1996) Properties of olean-12-ene-3β,16β,22α,28-tetrol and some derivatives. Aust J Chem 49:775–783CrossRef
29.
go back to reference Tanaka T, Nakashima T, Ueda T, Tomii K, Kouno I (2007) Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chem Pharm Bull 55:899–901CrossRef Tanaka T, Nakashima T, Ueda T, Tomii K, Kouno I (2007) Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chem Pharm Bull 55:899–901CrossRef
30.
go back to reference Crespin F, Olliver E, Lavaud C, Babadjamian A, Faure R, Debrauwer L, Balansard G, Boudon G (1993) Triterpenoid saponins from Opilia celtidifolia. Phytochemistry 33:657–661CrossRef Crespin F, Olliver E, Lavaud C, Babadjamian A, Faure R, Debrauwer L, Balansard G, Boudon G (1993) Triterpenoid saponins from Opilia celtidifolia. Phytochemistry 33:657–661CrossRef
31.
go back to reference Shaheen F, Muhammad A, Rubeena S, Irfanullah, Bibi S (2001) Spectral assignments and reference data. Magn Reson Chem 39:399–405 Shaheen F, Muhammad A, Rubeena S, Irfanullah, Bibi S (2001) Spectral assignments and reference data. Magn Reson Chem 39:399–405
32.
go back to reference Yoon N, Eom T, Kim M, Kim SJ (2009) Inhibitory effect of phlorotannins isolated from Ecklonia cava on mushroom tyrosinase activity and melanin formation in mouse B16F10 melanoma cells. Agric Food Chem 57:4124–4129CrossRef Yoon N, Eom T, Kim M, Kim SJ (2009) Inhibitory effect of phlorotannins isolated from Ecklonia cava on mushroom tyrosinase activity and melanin formation in mouse B16F10 melanoma cells. Agric Food Chem 57:4124–4129CrossRef
33.
go back to reference Kamauchi H, Kinoshita K, Takatori K, Sugita T, Takahashi K, Koyama K (2015) New sesquiterpenoids isolated from Atractylodes lancea fermented by marine fungus. Tetrahedron 71:1909–1914CrossRef Kamauchi H, Kinoshita K, Takatori K, Sugita T, Takahashi K, Koyama K (2015) New sesquiterpenoids isolated from Atractylodes lancea fermented by marine fungus. Tetrahedron 71:1909–1914CrossRef
Metadata
Title
Triterpenoid saponins from Polaskia chichipe Backbg. and their inhibitory or promotional effects on the melanogenesis of B16 melanoma cells
Authors
Koji Fujihara
Kunio Takahashi
Kiyotaka Koyama
Kaoru Kinoshita
Publication date
01-10-2017
Publisher
Springer Singapore
Published in
Journal of Natural Medicines / Issue 4/2017
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-017-1082-9

Other articles of this Issue 4/2017

Journal of Natural Medicines 4/2017 Go to the issue