Many classes of phytochemical products are finding therapeutic use, for example, complex triterpenoid saponins containing in their structures monoterpene moieties. Some of these compounds possess cytotoxic, anti-HIV and adjuvant activities. This review aims to give an overview of these complex triterpenoid saponins with biological activity from the Leguminosae.
MahatoSB, PalBC, NandyAK. (1992) Structure elucidation of two acylated triterpenoid bisglycosides from Acacia auriculiformis Cunn. Tetrahedron, 48, 6717–6728.
2.
GafurMA, ObataT, KiuchiF, TsudaY. (1997) Acacia concinna saponins. I. Structures of prosapogenols, concinnosides A–F, isolated from the alkaline hydrolysate of the highly polar saponin fraction. Chemical & Pharmaceutical Bulletin, 45, 620-625.
3.
KiuchiF, GafurMA, ObataT, TachibanaA, TsudaY. (1997) Acacia concinna saponins. II. Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction. Chemical & Pharmaceutical Bulletin, 45, 807-812.
4.
TezukaY, HondaK, BanskotaAH, ThetMM, KadotaS. (2000) Kinmoonosides A–C, three new cytotoxic saponins from the fruits of Acacia concinna, a medicinal plant collected in Myanmar. Journal of Natural Products, 63, 1658–1664.
5.
HaridasV, HiguchiM, JayatilakeGS, BaileyD, MujooK, BlakeME, ArntzenCJ, GuttermanJU. (2001) Avicins: Triterpenoid saponins from Acacia victoriae Bentham induce apoptosis by mitochondrial perturbation. Proceedings of the National Academy of Sciences of the United States of America, 98, 5821–5826.
6.
HanausekM, GaneshP, WalaszekZ, ArntzenCJ, SlagaTJ, GuttermanJU. (2001) Avicins, a family of triterpenoid saponins from Acacia victoriae Bentham, suppress H-ras mutations and aneuploidy in a murine skin carcinogenesis model. Proceedings of the National Academy of Sciences of the United States of America, 98, 11551–11556.
7.
HaridasV, ArntzenCJ, GuttermanJU. (2001) Avicins, a family of triterpenoid saponins from Acacia victoriae Bentham, inhibit activation of nuclear factor-κB by inhibiting both its nuclear localization and ability to bind DNA. Proceedings of the National Academy of Sciences of the United States of America, 98, 11557–11562.
8.
MujooK, HaridasV, HoffmannJJ, WächterGA, HutterLK, LuY, BlakeME, JayatilakeGS, BaileyD, MillsGB, GuttermanJU. (2001) Triterpenoid saponins from Acacia victoriae Bentham decrease tumor cell proliferation and induce apoptosis. Cancer Research, 61, 5486–5490.
9.
JayatilakeGS, FreebergDR, LiuZ, RichheimerSL, BlakeME, BaileyDT, HaridasV, GuttermanJU. (2003) Isolation and structures of avicins D and G: In vitro tumor-inhibitory saponins derived from Acacia victoriae.Journal of Natural Products, 66, 779–783.
10.
IkedaT, FujiwaraS, KinjoJ, NoharaT, IdaY, ShojiJ, ShinguT, IsobeR, KajimotoT. (1995) Three new triterpenoidal saponins acylated with monoterpenic acid from Albizziae cortex. Bulletin of the Chemical Society of Japan, 68, 3483–3490.
11.
MaL, TuG, ChenS, ZhangR, LaiL, XuX, TangY. (1996) NMR determination of the structure of Julibroside J1. Carbohydrate Research, 281, 35–46.
12.
IkedaT, FujiwaraS, ArakiK, KinjoJ, NoharaT, MiyoshiT. (1997) Cytotoxic glycosides from Albizia julibrissin. Journal of Natural Products, 60, 102–107.
13.
ZouK, ZhaoY, TuG, CuiJ, JiaZ, ZhangR. (2000) Two diastereomeric saponins with cytotoxic activity from Albizia julibrissin. Carbohydrate Research, 324, 182–188.
ZhengL, ZhengJ, ZhaoY, WangB, WuL, LiangH. (2006) Three antitumor saponins from Albizia julibrissin. Bioorganic & Medicinal Chemistry Letters, 16, 2765–2768.
17.
BeutlerJA, KashmanY, PannellLK, CardellinaJHII, AlexanderMRA, BalaschakMS, PratherTR, ShoemakerRH, BoydMR. (1997) Isolation and characterization of novel cytotoxic saponins from Archidendron ellipticum. Bioorganic & Medicinal Chemistry, 5, 1509–1517.
18.
BarbosaAP, da SilvaBP, ParenteJP. (2008) Brevifoliasaponin with adjuvant activity from Calliandra brevifolia.Zeitschrift für Naturforschung B – Chemical Sciences, 63B, 894–902.
19.
da SilvaBP, SoaresJBRC, de SouzaEP, PalatnikM, de SousaCBP, ParenteJP. (2005) Pulcherrimasaponin, from the leaves of Calliandra pulcherrima, as adjuvant for immunization in the murine model of visceral leishmaniasis. Vaccine, 23, 1061–1071.
20.
TakedaT, NakamuraT, TakashimaS, YanoO, OgiharaY. (1993) Studies on the constituents of Calliandra anomala (Kunth) Macbr. I. Structure elucidation of two acylated triterpenoidal saponins. Chemical & Pharmaceutical Bulletin, 41, 2132–2137.
21.
NakamuraT, TakedaT, OgiharaY. (1994) Studies on the constituents of Calliandra anomala (Kunth) Macbr. II. Structure elucidation of four acylated triterpenoidal saponins. Chemical & Pharmaceutical Bulletin, 42, 1111–1115.
22.
TaniC, OgiharaY, MutugaM, NakamuraT, TakedaT. (1996) Studies on the constituents of Calliandra anomala (Kunth) Macbr. III. Structure elucidation of six acylated triterpenoidal saponins. Chemical & Pharmaceutical Bulletin, 44, 816–822.
23.
TaniC, OgiharaY, TakedaT. (1998) Studies on the constituents of Calliandra anomala (Kunth) Macbr. IV. Structure analysis by HPLC retention time and FAB-MS spectrum. Chemical & Pharmaceutical Bulletin, 46, 723–725.
24.
OkadaY, ShibataS, IkekawaT, JavellanaAMJ, KamoO. (1987) Entada saponin-III, a saponin isolated from the bark ofEntada phaseoloides. Phytochemistry, 26, 2789–2796.
25.
OkadaY, ShibataS, JavellanaAMJ, KamoO. (1988) Entada saponins (ES) II and IV from the bark ofEntada phaseoloides. Chemical & Pharmaceutical Bulletin, 36, 1264–1269.
26.
CioffiG, PiazFD, CaprariisPD, SanogoR, MarzoccoS, AutoreG, TommasiND. (2006) Antiproliferative triterpene saponins from Entada africana. Journal of Natural Products, 69, 1323–1329.
27.
OkadaY, KoyamaK, TakahashiK, OkuyamaT, ShibataS. (1980) Gleditsia saponins I. Structures of monoterpene moieties of gleditsia saponin C. Planta Medica, 40, 185–192.
28.
KonoshimaT, InuiH, SatoK, YonezawaM, SawadaT. (1980) Legume saponin of Gleditsia japonica Miquel. II. Desmonoterpenyl glycoside of echinocystic acid. Chemical & Pharmaceutical Bulletin, 28, 3473–3478.
29.
KonoshimaT, FukushimaH, InuiH, SatoK, SawadaT. (1981) The structure of prosapogenin obtained from the saponin ofGleditsia japonica. Phytochemistry, 20, 139–142.
30.
KonoshimaT, UmegakiY, SawadaT. (1981) Legume saponins of Gleditsia japonica Miquel. III. Further desmonoterpenyl glycosides of echinocystic acid. Chemical & Pharmaceutical Bulletin, 29, 2695–2699.
31.
KonoshimaT, SawadaT. (1982) Legume saponins of Gleditsia japonica Miquel. IV. 13C-Nuclear magnetic resonance spectral studies for structure elucidation of gleditsia saponins B and C. Chemical & Pharmaceutical Bulletin, 30, 2747–2760.
32.
KonoshimaT, SawadaT. (1982) Legume saponins of Gleditsia japonica Miquel. V. 13C Nuclear magnetic resonance spectral studies on the structures of gleditsia saponins D2, G and I. Chemical & Pharmaceutical Bulletin, 30, 4082–4087.
33.
ZhangZ, KoikeK, JiaZ, NikaidoT, GuoD, ZhengJ. (1999) Four new triterpenoidal saponins acylated with one monoterpenic acid from Gleditsia sinensis. Journal of Natural Products, 62, 740–745.
34.
ZhangZ, KoikeK, JiaZ, NikaidoT, GuoD, ZhengJ. (1999) Triterpenoidal saponins acylated with two monoterpenic acids from Gleditsia sinensis. Chemical & Pharmaceutical Bulletin, 47, 388–393.
35.
ZhangZ, KoikeK, JiaZ, NikaidoT, GuoD, ZhengJ. (1999) Gleditsiosides N–Q, new triterpenoid saponins from Gleditsia sinensis. Journal of Natural Products, 62, 877–881.
36.
KonoshimaT, SawadaT. (1984) Studies on the constituents of leguminous plants. VI. The structure elucidations of monoterpene glycosides from fruits of Gymnocladus chinensis Baillon. Chemical & Pharmaceutical Bulletin, 32, 2617–2621.
37.
KonoshimaT, SawadaT, KimuraT. (1984) Studies on the constituents of leguminous plants. VII. The structure of triterpenoid saponins from fruits of Gymnocladus chinensis Baillon. Chemical & Pharmaceutical Bulletin, 32, 4833–4841.
38.
KonoshimaT, SawadaT, KimuraT. (1985) Studies on the constituents of leguminous plants. VIII. The structure of a new triterpenoid saponin from the fruits of Gymnocladus chinensis Baillon. Chemical & Pharmaceutical Bulletin, 33, 4732–4739.
39.
KonoshimaT, KozukaM, SawadaT, KimuraT. (1987) Studies on the constituents of leguminous plants. IX. The structure of a new triterpenoid saponin from the fruits of Gymnocladus chinensis Baillon. Chemical & Pharmaceutical Bulletin, 35, 46–52.
40.
YoshikawaK, SuzakiY, TanakaM, AriharaS, NigamSK. (1997) Three acylated saponins and a related compound from Pithecellobium dulce. Journal of Natural Products, 60, 1269–1274.
41.
GuptaGL, NigamSS. (1971) Chemical examination of the leaves ofAcacia concinna. Planta Medica, 19, 55–62.
42.
KonoshimaT, YasudaI, KashiwadaY, CosentinoLM, LeeKH. (1995) Anti-AIDS agents, 21. Triterpenoid saponins as anti-HIV principles from fruits of Gleditsia japonica and Gymnocladus chinensis, and a structure-activity correlation. Journal of Natural Products, 58, 1372–1377.
43.
ChowLMC, TangJCO, TeoITN, ChuiCH, LauFY, LeungTWT, ChengG, WongRSM, WongILK, TsangKMS, TanWQ, ZhaoYZ, LaiKB, LamWH, GuoDA, ChanASC. (2002) Antiproliferative activity of the extract of Gleditsia sinensis fruit on human solid tumour cell lines. Chemotherapy, 48, 303–308.
44.
ChowLMC, ChuiCH, TangJCO, TeoITN, LauFY, ChengGYM, WongRSM, LeungTWT, LaiKB, YauMYC, GouD, ChanASC. (2003) Gleditsia sinensis fruit extract is a potential chemotherapeutic agent in chronic and acute myelogenous leukemia. Oncology Reports, 10, 1601-1607.
