Benzophenanthridine alkaloids belong to the benzyl isoquinoline family of alkaloids, which are mainly found in Papaveraceae and Rutaceae. To date, over 100 compounds have been isolated from natural herbal medicines which display a variety of pharmacological functions. In this paper, we have summarized the work since 1980 and our own research on benzophenanthridine alkaloids in terms of their chemical structures and distribution, biosynthesis, biotransformation and metabolism, spectral characteristics, pharmacological activities and toxicity. This review lays the foundation for further research into benzophenanthridine alkaloids and their potential applications.
KraneBD, FagbuleMO, ShammaM. (1984) The benzophenanthridine alkaloids. Journal of Natural Products, 47, 1-43.
4.
GazianoR, MoroniG, BueC, MieleMT, Sinibaldi-VallebonaP, PicaF. (2016) Antitumor effects of the benzophenanthridine alkaloid sanguinarine: Evidence and perspectives. World Journal of Gastrointestinal Oncology, 8, 30-39.
DvorakZ, KubanV, KlejdusB, HlavacJ. (2006) Quaternary benzo[c]phenanthridines sanguinarine and chelerythrine: a review of investigations from chemical and biological studies. Heterocycles, 68, 2403-2422.
7.
ParkJE, CuongTD, HungTM, LeeI, NaM, KimJC, RyooS, LeeJ-H, ChoiJS, WooMH, MinBS., (2011) Alkaloids from Chelidonium majus and their inhibitory effects on LPS-induced NO production in RAW264.7 cells. Bioorganic & Medicinal Chemistry Letters, 21, 6960-6963.
8.
El-AfifiFAl-Eisawi D, Al-KhalS, ShiffPL. (1986) Alkaloids of Glaucium grandiflorum. Journal of Natural Products, 49, 1166-1167.
TakaoN, IwasaK, KamigauchiM, SugiuraM. (1978) Studies on the alkaloids of Papaveraceous plants. Conformationl analysis of some hydrobenzophenanthridine-type alkaloids. Chemical & Pharmaceutical Bulletin, 26, 1880-1889.
11.
SlavikFJ, MasarykovaU, BrnoC. (1959) Alkaloids of the Papaveraceae. XII. Constitution of (-)-norchelidonine, a new alkaloid of Glauciumflavum. Collection of Czechoslovak Chemical Communications, 24, 3601-3605.
12.
NečasM, DostálJ, KejnovskáI, VorlíčkováM, SlavíkJ. (2005) Molecular and crystal structures of (+)-homochelidonine, (+)-chelamine, and (-)-norchelidonine. Journal of Molecular Structure, 734, 1-6.
13.
SlavikJ, TaborskaE, BochorakovaH. (1994) The nature of the so-called methoxychelidonine. Collection of Czechoslovak Chemical Communications, 59, 429-434.
14.
SlavikJ, SlavikovaL, BrabenecJ. (1965) Alkaloids of Papaveraceae. XXX. Other alkaloids from the roots of Chelidonium majus. Collection of Czechoslovak Chemical Communications, 30, 3697-3704.
15.
NaraoT, KinukoI. (1979) Studies on Papaveraceae alkaloids. XXXIII. Alkaloids of Corydalis incisa. 12. Structure of corynolamines. Chemical & Pharmaceutical Bulletin, 27, 2194-2197.
16.
KimDK, EunJS, ShinTY, EomDO, LimJP. (2000) Benzo[c] phenanthridine alkaloids from Corydalis incisa. Archives of Pharmacal Research, 23, 589-591.
17.
IsawaK, TakaoN, NonakaG. (1979) Studies on the alkaloids of Papaveraceous plants. Part XXXIV. (+)-Corynoline 11-O-sulfate from Corydalis incisa. Phytochemistry, 18, 1725-1728.
18.
ZhangY, QinMJ, XieGY. (2008) Analysis of alkaloid compositions from Corydalis incisa. Huanjing Xuebao, 17, 67-69.
19.
HongH, FangQC. (1986) Chemical study on alkaloids from Corydalis bulleyana. Planta Medica, 52, 193-198.
20.
ZengWG, LiangWZ, TuGS. (1987) Chemical study of alkaloids from Corydalis bungeana. Planta Medica, 53, 418-420.
21.
CuiZ, ZhuP, OndaM, HarigayaY, IguchiM, KondaY, TakayanagiH, OguraH. (1990) Absolute stereochemistry of (-)-ambinine. Journal of Natural Products, 53, 1182-1186.
22.
OechslinSM, KonigGM, Oechslin-MerkelK, WrightAD, MiyagawaM. (1991) An NMR study offour benzophenanthridine alkaloids. Journal of Natural Products, 54, 519-524.
23.
TarusPK, CoombesPH, CrouchNR, MulhollandDA. (2006) Benzo[c]phenanthridine alkaloids from stem bark of the forest Knobwood, Zanthoxylumdavyi (Rutaceae). South African Journal of Botany, 72, 555-558.
24.
NgKM, GrayAI, WatermanPG. (1987) Benzophenanthridine alkaloids from the stem bark of a Zanthoxylum species. Phytochemistry, 26, 3251-3254.
25.
HuJ, ZhangWD, LiuRH, ZhangC, ShenYH, LiHL, LiangMJ, XuXK. (2006) Benzophenanthridine alkaloids from Zanthoxylum nitidum (Roxb.) DC and their analgesic and anti-inflammatory activities. Chemistry & Biodiversity, 3, 990-995.
26.
FuchinoH, KawanoM, Mori-YasumotoK, SekitaS, SatakeM, IshikawaT, KiuchiF, KawahiraN. (2010) In vitro leishmanicidalactivity of benzophenanthridine alkaloids from Bocconiapearcei and related compounds. Chemical & Pharmaceutical Bulletin, 58, 1047-1050.
27.
ChenJJ, FangHY, DuhCY, ChenIS. (2005) New indolopyridoquinazoline, benzo[c]phenanthridines and cytotoxic constituents from Zanthoxylum integrifoliolum. Planta Medica, 71, 470-475.
28.
YangCH, ChengMJ, ChiangM Y, KuoYH, WangCJ, ChenIS. (2008) Dihydrobenzo[c]phenanthridine alkaloids from stem bark of Zanthoxylum nitidum. Journal of Natural Products, 71, 669-673.
29.
TaneP, WaboHK, ConnollyJD. (2005) A new benzophenanthridine alkaloid from Zanthoxylum buesgenii. Fitoterapia, 76, 656-660.
30.
DengAJ, QinHL. (2010) Cytotoxic dihydrobenzophenanthridine alkaloids from the roots of Macleaya microcarpa. Phytochemistry, 71, 816-822.
31.
GengD, LiDX, ShiY. (2009) A new benzophenanthridine alkaloid from Zanthoxylum nitidum. Chinese Journal of Natural Medicines, 7, 274-277.
32.
ItokawaH, IkutaA, TsutsuiN, ShiguroI. (1978) Alkaloids and a sterol from Chelidonium japonicum. Phytochemrstry, 17, 839-840.
JenCM, TsaiIL, HorngDJ, ChenIS. (1993). Isolation and structure determination of two new compounds from Zanthoxylum integrifoliolum. Journal of Natural Products, 56, 2019-2021.
35.
JullianV, BourdyG, GeorgesS, MaurelS, SauvainM. (2006) Validation of use of a traditional antimalarial remedy from French Guiana Zanthoxylum rhoifolium Lam. Journal of Ethnopharmacology, 106, 348-352.
36.
ZhuW, TuZB. (1986) Alkaloids from Zanthoxylum nitidum var. fastuosum. Journal of Wuhan Botanical Research, 4, 253-255.
37.
KhalidSA, WatermanPG. (1985) 6-hydroxymethyldihydronitidine from Fagaropsis angolensis. Journal of Natural Products, 48, 118-119.
38.
SchumacherHM, ZenkMH. (1988) Partial purification and characterization of dihydrobenzophenanthridine oxidase from Eschscholtzia californica cell suspension cultures. Plant Cell Reports, 7, 43-46.
NissankaApk, KarunaratneVBandaraBmrKumarVNakanishiTNishiMInadaA, TillekeratneLmv, WijesundaraDsa, GunatilakaAal. (2001) Antimicrobial alkaloids from Zanthoxylum tetraspermum and caudatum. Phytochemistry, 56, 857-861.
41.
ZhuD. (2010) Studies on the chemical components of Zanthoxylum simulans. Master Dissertation of South-Central University for Nationalities, 1-36.
42.
LuoX, PedroL, MilicV, MulhovoS, DuarteA, DuarteN, FerreiraM. (2012) Antibacterial benzofuran neolignans and benzophenanthridine alkaloids from the roots of Zanthoxylum capense. Planta Medica, 78, 148-153.
43.
ChenIS, WuSJ, LeuYL, TsaiIW, WuTS. (1996) Alkaloids from root bark of Zanthoxylum simulans. Phytochemistry, 42, 217-219.
44.
ZhouTD.(1986) The preliminary study on the distribution of benzophenanthridine alkaloids in Papaveraceae and Rutaceae. Chinese Bulletin of Botany, 4, 38-41.
45.
Tin-WaM, FongHhs, AbrahamDJ, TrojanekJ, FarnsworthNR. (1972) Structure of sanguidimerine, a newmajor alkaloid from Sanguinaria canadensis(Papaveraceae). Journal of Pharmaceutical Sciences, 61, 1846-1847.
46.
SlunskáZ, GelnarováE, HammerováJ, TáborskáE, SlaninováI. (2010) Effect of quaternary benzo[c]phenanthridine alkaloids sanguilutine and chelilutine on normal and cancer cells. Toxicology in Vitro, 24, 697-706.
47.
SeckarovaP, MarekR, DostalJ, DommisseR, EsmansEL. (2002) Structural studies of benzophenanthridine alkaloid free bases by NMR spectroscopy. Magnetic Resonance in Chemistry, 40, 147-152.
48.
XiangY, ZhengQA, ZhangCK, LiZ, TuZB. (2000) Alkaloids and coumarins from Zanthoxylum dimorphophyllum Hemsl.var. spinifolium Rehd. et Wils. Journal of Wuhan Botanical Research, 18, 143-145.
49.
TousekJ, DommissebR, DostalJ, ZakZ, PietersL, MarekR. (2002) Configurations and conformations of sanguinarine and chelerythrine free bases stereoisomers. Journal of Molecular Structure, 613, 103-113.
50.
HagelJM, FacchiniPJ. (2013) Benzylisoquinoline alkaloid metabolism: A century of discovery and a brave new world. Plant Cell Physiology, 54, 647-672.
51.
HouY. (2014) Biotransformation of active compounds in Schisandrachinensis and Corydalis ambignavar. amurensis. Master Dissertation of Shenyang Pharmaceutical University, 66-74.
52.
LiuZH.(2015) Studies on the chemical components of leaves of Corydalis ambiguavar. amurensis and the metabolism of ambinine in rat. Doctor Dissertation of Shenyang Pharmaceutical University, 84-100.
53.
TakaoN, IwasaK, KamigauchiM, SugiuraM. (1978) Studies on the alkaloids of Papaveraceous plants. Conformationl analysis of some hydrobenzophenanthridine-type alkaloids. Chemical & Pharmaceutical Bulletin, 26, 1880-1889.
TanGT, PezzutoJM, KinghornD. (1991) Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Journal of Natural Products, 54, 143-154.
59.
ChengMJ, LeeKH, TsaiIL, ChenIS. (2005) Two new sesquiterpenoids and anti-HIV principles from the root bark of Zanthoxylum ailanthoides. Bioorganic & Medicinal Chemistry, 13, 5915-5920.
60.
FuchinoH, KawanoM, Mori-YasumotoK, SekitaS, SatakeM, IshikawaT, KiuchiF, KawahiraN. (2010) In vitro leishmanicidal activity of benzophenanthridine alkaloids from Bocconiapearcei and related compounds. Chemical & Pharmaceutical Bulletin, 58, 1047-1050.
61.
WuYR, MaYB, ZhaoYX. (2007) Two new quaternary alkaloids and anti-hepatitis B virus active constituents from Corydalis saxicola. Planta Medica, 73, 781-791.
62.
JurskyF, BaliovaM. (2011) Differential effect of the benzophenanthridine alkaloids sanguinarine and chelerythrine on glycine transporters. Neurochemistry International, 58, 641-647.
63.
HuJ, ZhangWD, LiuRH, ZhangC, ShenYH, LiHL, LiangMJ, XuXK. (2006) Benzophenanthridine alkaloids from Zanthoxylum nitidum (Roxb.) DC and their analgesic and anti-inflammatory activities. Chemistry & Biodiversity, 3, 990-995.
64.
WolfJ, KniplingL. (1993) Antimicrotubuleproperties of benzophenanthridine alkaloids. Biochemistry, 32, 13334-13339.
65.
LiuLM, LiuHG. (2010) Anti-hepatoma activity of nitidine chloride and its effect on topoisomerase. Chinese Pharmacological Bulletin, 26, 497-500.
66.
PhilchenkovA, KaminskyyV, ZavelevichM, StoikaR. (2008) Apoptogenic activity of two benzophenanthridine alkaloids from Chelidonium majus L. does not correlate with their DNA damaging effects. Toxicology in Vitro, 22, 287-295.
67.
WangGX, ZhouZ, JiangDX, HanJ, WangJF. (2010) In vivo anthelmintic activity of five alkaloids from Macleaya microcarpa (Maxim) Fedde against Dactylogyrus intermedius in Carassius auratus. Veterinary Parasitology, 171, 305-313.
68.
FengG, ZhangJ, FengJT, ZhangX. (2008) Isolation and identification of insecticidal composition of Macleaya microcarpa. Acta Botanica Boreali, 28, 179-182.
69.
HuangQY, PengF, LiuNM, YangHZ, HuQ, FengF, SunH. (2004) Study on molluscicidal effects of Eomecon chionantha alkaloids. Chinese Journal of Schistosomiasis Control, 16, 55-57.
70.
YangZY. (2013) Chemical constituents and biological activities of alkaloids from Corydalis ambigua var. amurensis. Master Dissertation of Shenyang Pharmaceutical University, 77-81.
