哈尔滨商业大学, a. 国家教育部抗肿瘤天然药物工程研究中心; b. 药学院药物工程技术研究中心, 哈尔滨 150076
Research Progress on the Chemical Constituents and Active Constituents of Cycas revolute Thunb
LIU Ying-jiea,b, HUANG Yu-linga, XU Yinga,b*, FU Ji-yuana
a. Engineering Research Center of Natural Anticancer Drugs, Ministry of Education; b. Engineering Research Center for Medicine, College of Pharmacy, Harbin University of Commerce, Harbin 150076, China
Abstract:Cycas revolute Thunb is a first class protected plant in China and has high medicinal value. As early as the Qing dynasty, it was recorded that Cycas was use to treat disease. Early research on Cycas mainly focused on classification, protection and breeding. In recent years, people began to study the main chemical constituents, chemical structure and pharmacological effects of Cycas, which laid a solid theoretical foundation for the further development and utilization of Cycas. At present, most of amentoflavone derivatives and hinokiflavone derivatives found in Cycas have the therapeutic effect on tumor. In addition to the antitumor activity, the extracts of Cycas also have antibacterial, antioxidant and immunological activities.
刘颖杰, 黄玉玲, 许颖, 付纪源. 苏铁的化学成分和活性成分的研究进展[J]. 中国药学杂志, 2020, 55(18): 1492-1498.
LIU Ying-jie, HUANG Yu-ling, XU Ying, FU Ji-yuan. Research Progress on the Chemical Constituents and Active Constituents of Cycas revolute Thunb. Chinese Pharmaceutical Journal, 2020, 55(18): 1492-1498.
FU R S. Current research status and outlook of Cycas revoluta[J]. Wuyi Sci J(武夷科学), 2000, 16:187-190.
[2]
ZHOU J M. On the status quo and conservation of Cycas revoluta in China[J]. Forest Res Manag(林业资源管理), 2003, 16(1):48-51.
[3]
PU H, YANG S L, TERRENCE W W. A preliminary study on the endangered plants of Cycas in China[J]. Res Devel Prot(资源开发与保护), 1993, (3):202-204.
[4]
WANG S H.Studies on the active ingredients and mechanism of cycads inhibiting the growth of NSCLC[D]. Beijing: Minzu University of China, 2019.
[5]
ZHOU Y, ZHANG X R, PENG S L, et al. General outline of study on Cycas[J]. World Sci Technol(世界科学技术), 2001, 3(1):47-50.
[6]
PAN T W. Studies on chemical constituents of Cycas revoluta Thunb. and modification of gentiopicroside [D]. Kunming:Yunnan University of Traditional Chinese Medicine, 2012.
[7]
SUN C M, SYU W J, HUANG Y T, et al. Selective cytotoxicity of ginkgetin from Selaginella moellendorffii[J]. J Nat Prod, 1997, 60(4):382-384.
[8]
CHEN T, WEI L, GUAN X, et al. Biflavones from Ginkgo biloba as inhibitors of human thrombin[J]. Bioorg Chem, 2019,92:103-113.
[9]
LOBSTEIN-GUTH A, BRIANCON-SCHEID F, VICTOIRE C, et al. Isolation of amentoflavone from Ginkgo biloba[J]. Planta Med, 1988, 54(6):555-556.
[10]
RMARKHAM K, SHEPPARD C, GEIGER H. 13C-NMR studies of some naturally occurring amentoflavone and hinokiflavone biflavonoids[J]. Phytochemistry, 1987, 26(12):3335-3337.
[11]
HYUN S K, JUNG H A, CHUNG H Y, et al. In vitro peroxynitrite scavenging activity of 6-hydroxykynurenic acid and other flavonoids from Gingko biloba yellow leaves[J]. Arch Pharm Res, 2006, 29(12):1074-1079.
[12]
KRAUZE-BARANOWSKA M, POBLOCKA L, EL-HELA A A. Biflavones from Chamaecyparis obtusa[J]. Z Naturforsch C J Biosci, 2005, 60(9-10):679-685.
[13]
YEH P H, SHIEH Y D, HSU L C, et al. Naturally occurring cytotoxic [3′-8″]-biflavonoids from Podocarpus nakaii[J]. J Tradit Complement Med, 2012, 2(3):220-226.
[14]
ZHOU Z, FU C. A new flavanone and other constituents from the rhizomes of Cyperus rotundus and their antioxidant activities[J]. Chem Nat Compd, 2013, 48(6):963-965.
[15]
LIU P, WENG Z, GE G, et al. Biflavones from Ginkgo biloba as novel pancreatic lipase inhibitors: inhibition potentials and mechanism[J]. Int J Biol Macromol, 2018,118(2): 2216-2223.
[16]
ZHOU Y, JIANG S Y, LI C N, et al. Chemical composition of Cycas panzhihua[J]. J Appl Envir Biol(应用与环境生物学报), 1999, 5(4):34-37.
[17]
MURTI V V S, RAMAN P V, SESHADRI T R. Cupressuflavone, a new member of the biflavonyl group[J]. Tetrahedron Lett, 1964, 5(40):2995-2997.
[18]
ROMANI A, GALARDI C, PINELLI P, et al. HPLC quantification of flavonoids and biflavonoids in Cupressaceae leaves[J]. Chromatographia, 2002, 56(7):469-474.
[19]
BAKER W, FLEMONS G F, WINTER R. The structure of ginkgetin. Part Ⅱ. New syntheses of 5: 8-dihydroxy-4′-methoxyflavone[J]. J Chem Soc, 1949:1560-1562.
[20]
ZHAO C, REN X, LI C, et al. Coupling ultrasound with heat-reflux to improve the extraction of quercetin, kaempferol, ginkgetin and sciadopitysin from Mairei Yew leaves[J]. Appl Sci, 2019, 9(4):795-810.
[21]
LEE M K, LIM S W, YANG H, et al. Osteoblast differentiation stimulating activity of biflavonoids from Cephalotaxus koreana[J]. Bioorg Med Chem Lett, 2006, 16(11):2850-2854.
[22]
DOSSAII S F, BELL E A, WALLACE J W. Biflavones of dioon[J]. Phytochemistry, 1973, 12(2):371-373.
[23]
ZHENG J X, ZHENG Y, ZHI H, et al. New 3′,8″-linked biflavonoids from Selaginella uncinata displaying protective effect against anoxia[J]. Molecules, 2011, 16(8):6206-6214.
[24]
DOSSAJI S F, MABRY T J, BELL E A. Biflavanoids of the Cycadales[J]. Biochem Syst Ecol, 1975, 2(3):171-175.
[25]
MOAWAD A, HETTA M, ZJAWIONY J K, et al. Phytochemical investigation of Cycas circinalis and Cycas revoluta leaflets: moderately active antibacterial biflavonoids[J]. Planta Med, 2010, 76(8):796-802.
[26]
YANG N, TAO W, DUAN J. Antithrombotic flavonoids from the faeces of Trogopterus xanthipes[J]. Nat Prod Res, 2010, 24(19):1843-1849.
[27]
GADEK P A, QUINN C J. Biflavones of taxodiaceae[J]. Biochem Syst Ecol, 1989, 17(5): 365-372.
[28]
SILVA G L, CHAI H, GUPTA M P, et al. Cytotoxic biflavonoids from Selaginella willdenowii[J]. Phytochemistry, 1995, 40(1):129-134.
[29]
MOAWAD A, HETTA M, ZJAWIONY J K, et al. Two new dihydroamentoflavone glycosides from Cycas revoluta[J]. Nat Prod Res, 2014, 28(1):41-47.
[30]
KAWAMINAMI M, KAWANO I, KOBAYASHI A, et al. The fundamental structure of cycasin, (methyl‐ONN-azoxy)methyl β-d-glucopyranoside[J]. Acta Crystallogr Sect B, 1981, 37(11):2026-2029.
[31]
NAIR J J, VAN STADEN J. Isolation and quantification of the toxic methylazoxymethanol glycoside macrozamin in selected South African cycad species[J]. S Afr J Bot, 2012, 82(82):108-112.
[32]
ZHOU Y, PENG S L, LI C N, et al. A new C-glycosylflavone from the leaves of Cycas panzhihuaensis[J]. Acta Bot Sin, 2002, 44(1):101-103.
[33]
FLAMINI G. Flavonoids and other compounds from the aerial parts of Viola etrusca[J]. Chem Biodivers, 2007, 4(2):139-144.
[34]
FENG S X, LIU M F, WEI X Y, et al. Triterpenoids and flavonoids from the leaves of Microcos paniculata[J]. J Trop and Subtrop Bot(热带亚热带植物学报), 2008, 16(1):51-56.
[35]
FICARRA R, TOMMASINI S, RANERI D, et al. Study of flavonoids/β-cyclodextrins inclusion complexes by NMR, FT-IR, DSC, X-ray investigation[J]. J Pharm Biomed Anal, 2002, 29(6):1005-1014.
[36]
CHENG X, WAN J, LI P, et al. Ultrasonic/microwave assisted extraction and diagnostic ion filtering strategy by liquid chromatography-quadrupole time-of-flight mass spectrometry for rapid characterization of flavonoids in Spatholobus suberectus[J]. J Chromatogr A, 2011, 1218(34):5774-5786.
[37]
POPOVICI G, WEISSENBÖCK G, BOUILLANT M, et al. Isolation and characterization of flavonoids from Avena sativa L[J]. Z Med Phys, 1977, 85(2):103-115.
[38]
DEL RIO D, STALMACH A, CALANI L, et al. Bioavailability of coffee chlorogenic acids and green tea flavan-3-ols[J]. Nutrients, 2010, 2(8):820-833.
[39]
ZHANG Y, YAN G, SUN C, et al. Apoptosis effects of dihydrokaempferol isolated from Bauhinia championii on synoviocytes[J]. Evid Based Complement Alternat Med, 2018,(2):1-10.
[40]
FU M, LI X Y, WANG D Y, et al. Flavonoids constituents of leaves of Ampelopsis grossedentata(Hand-Mass)W.T.wang[J]. Chin Pharm J(中国药学杂志), 2015, 50(7):574-578.
[41]
BRENES M, HIDALGO F J, GARCÍA A, et al. Pinoresinol and 1-acetoxypinoresinol, two new phenolic compounds identified in olive oil[J]. J Am Oil Chem Soc, 2000, 77(7):715-720.
[42]
ZHANG X Q, GENG C A, CHEN X L, et al. Chemical constituents from Cycas revoluta[J]. Nat Prod Res Dev(天然产物研究与开发), 2019, 31(1):75-80.
[43]
MENG J, JIANG T, ASLAM BHATTI H, et al. Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin[J]. Org Biomol Chem, 2010, 8(1):107-113.
[44]
JIANG Y, LIU Y, GUO Q, et al. Lignanoids from an aqueous extract of the roots of Codonopsis pilosula[J]. Acta Pharm Sin(药学学报), 2016, 51(4):616-625.
[45]
XIE L, AKAO T, HAMASAKI K, et al. Biotransformation of pinoresinol diglucoside to mammalian lignans by human intestinal microflora, and isolation of enterococcus faecalis strain PDG-1 responsible for the transformation of (+)-pinoresinol to (+)-lariciresinol[J]. Chem Pharm Bull, 2003, 51(5):508-515.
[46]
KUCUKBOYACI N, ORHAN I, SENER B, et al. Assessment of enzyme inhibitory and antioxidant activities of lignans from Taxus baccata L[J]. Z Naturforsch C J Biosci, 2010, 65(3-4):187-194.
[47]
PING Y D, ZHANG Y H, LI Y. Antitumor activity of alcohol extract from Murraya exotica L[J]. Chin Pharm J(中国药学杂志), 2017, 52(18):1585-1588.
[48]
LOMENICK B, SHI H, HUANG J, et al. Identification and characterization of β-sitosterol target proteins[J]. Bioorg Med Chem Lett, 2015, 25(21):4976-4979.
[49]
XIE J X, JI Z. The chemical constituents of the Chinese drug "Yadanzi" I. Isolation and identification of daucosterol, brucein D and brucein E (author′s transl)[J]. Acta Pharm Sin(药学学报), 1981, 16(1):53-55.
[50]
YAN X Y, YIN X J, WANG G K, et al. Chemical constituents of Medicago polymorpha[J]. Chin Pharm J(中国药学杂志), 2012, 47(6):415-418.
[51]
FORGO P, KÖVÉR K E. Gradient enhanced selective experiments in the 1H-NMR chemical shift assignment of the skeleton and side-chain resonances of stigmasterol, a phytosterol derivative[J]. Steroids, 2004, 69(1):43-50.
[52]
TAO S, WU J, QI S, et al. Scyphiphorins A and B, two new iridoid glycosides from the stem bark of a Chinese mangrove Scyphiphora hydrophyllacea[J]. Helv Chim Acta, 2007, 90(9):1718-1722.
[53]
FO E R, FERNANDES J B, VIEIRA P C, et al. Isolation of secoisolariciresinol diesters from stems of Simaba cuneata[J]. Phytochemistry, 1992, 31(6):2115-2116.
[54]
ZENG X J, WANG G C, WU X, et al. Chemical constituents from Syringa pinnatifolia[J]. Chin Tradit Herb Drugs(中草药), 2013, 44(13):1721-1725.
[55]
KUSUMOTO N, ASHITANI T, MURAYAMA T, et al. Antifungal abietane-type diterpenes from the cones of Taxodium distichum Rich[J]. J Chem Ecol, 2010, 36(12):1381-1386.
[56]
LI A, SHE X, ZHANG J, et al. Synthesis of C-7 oxidized abietane diterpenes from racemic ferruginyl methyl ether[J]. Tetrahedron, 2003, 59(30):5737-5741.
[57]
INABA Y, HASUDA T, HITOTSUYANAGI Y, et al. Abietane diterpenoids and a sesquiterpene pyridine alkaloid from Euonymus lutchuensis[J]. J Nat Prod, 2013, 76(6):1085-1090.
[58]
MINH C V, NHIEM N X, YEN H T, et al. Chemical constituents of Trichosanthes kirilowii and their cytotoxic activities[J]. Arch Pharm Res, 2015, 38(8):1443-1448.
[59]
WANG X W, ZHANG H P, CHEN F, et al. A new lignan from Gynostemma pentaphyllum[J]. Chin Chem Lett, 2009, 20(5):589-591.
[60]
LI Y, XIE S, YING J, et al. Chemical structures of lignans and neolignans isolated from Lauraceae[J]. Molecules, 2018, 23(12):3164-3182.
[61]
CHOI H G, CHOI Y H, KIM J H, et al. A new neolignan and lignans from the stems of Lindera obtusiloba Blume and their anti-allergic inflammatory effects[J]. Arch Pharm Res, 2014, 37(4):467-472.
[62]
RATTANABURI S, MAHABUSARAKAM W, PHONGPAICHIT S, et al. Neolignans from Callistemon lanceolatus[J]. Phytochem Lett, 2012, 5(1):18-21.
[63]
ZHANG Y M, GONG Q F, YANG J Q, et al. Antioxidant constituents from Pinus massoniana(Pinaceae)[J]. J Plant Classif Res(植物分类与资源学报), 2013, 35(2):209-215.
[64]
TAO Y, JIANG W, CHENG Y, et al. Two new compounds from Senecio cannabifolius[J]. J Asian Nat Prod Res, 2012, 14(9):826-830.
[65]
KIM I, CHIN Y, LIM S W, et al. Norisoprenoids and hepatoprotective flavone glycosides from the aerial parts of Beta vulgaris var.cicla[J]. Arch Pharm Res, 2004, 27(6):600-603.
[66]
PETTIT G R, HERALD C L, ODE R H, et al. The isolation of loliolide from an indian ocean opisthobranch mollusc[J]. J Nat Prod, 1980, 43(6):752-755.
[67]
LIU T X, WANG S H. Research progress on use of Cycas revolute[J]. J Minzu Univ Chin (Nat Sci Edit)(中央民族大学学报:自然科学版), 2016, 25(1):49-54.
[68]
WANG S H, LIU T X. Effects of total flavonoids from Cycas revolute on inhibition and immune function of model mice with Lewis lung cancer[J]. Chin J Immunol(中国免疫学杂志), 2016, 32(11):1598-1602.
[69]
WANG S H, MA S B, YAN Y, et al. Effects of total flavonoids from Cycas revolute on expression of VEGF, Bfgf, HIF-1α and NF-κB in model mice of Lewis lung cancer[J]. Chin J Immunol(中国免疫学杂志), 2017, 33(7):1029-1034.
[70]
KONG F C, GU H, WANG H Y, et al. Effect of Cvcas revolute Thunb extract on apoptosis of A549 cells and the possible mechanism[J]. Chin New Drugs J(中国新药杂志), 2008, 17(8):667-672.
[71]
SUN L L, BI F Y, LING L F, et al. Inhibiting effect of Sago cycas leaves on proliferation of leukemia K562 and HL-60 cells[J]. J Jiujiang Univ (Nat Sci Ed)(九江学院学报 社会科学版), 2001, 16(4):192-193.
[72]
CUI X L, LI K J, REN H X, et al. Extract of Cycas revoluta Thunb. enhances the inhibitory effect of 5- fluorouracil on gastric cancer cells through the AKT-mTOR pathway[J]. World J Gastroenterol, 2019, 25(15):1854-1864.
[73]
BERA S, DAS B, DE A, et al. Metabolite profiling and in-vitro colon cancer protective activity of Cycas revoluta cone extract[J]. Nat Prod Res, 2018, 34(4):599-603.
[74]
ISMAIL A, HASSAN H M, MOAWAD A S, et al. Chemical composition and therapeutic potential of three Cycas species in brain damage and pancreatitis provoked by γ-radiation exposure in rats[J]. J Rad Res App Sci, 2020, 13(1): 200-214.
[75]
YUAN S S, QIN W S, ZHANG Y, et al. Antibacterial activity of water extracts of Cycas siamensis seeds[J]. J Anhui Agricul Sci (安徽农业科学), 2017, 45(31):12-14.
[76]
MANDAL S M, MIGLIOLO L, DAS S, et al. Identification and characterization of a bactericidal and proapoptotic peptide from Cycas revoluta seeds with DNA binding properties[J]. J Cell Biochem, 2012, 113(1):184-193.
[77]
LIN Q Y, LI W L, LI X N, et al. Anti-tumor effect of total flavonoids of Cycas leaves combined with cisplatin on Lewis lung cancer mice[J]. Chin J Clin Pharmacol(中国临床药理学杂志), 2019, 35(16):1784-1787.
[78]
JIANG Y L. Animal carcinogenicity of certain Chinese herbs (review)[J]. Chin Tradit Herb Drugs(中草药), 1980, 11(9):425-431.
[79]
LAQUEUR G L, SPATZ M. Toxicology of cycasin[J]. Cancer Res, 1968, 28(11):2262-2267.
[80]
FORRESTER M B, LAYTON G M, VARNEY S M. Cycas revoluta (Sago Cycad) exposures reported to Texas poison centers[J]. Am J Emerg Med, 2019,38(8):1-6.
[81]
SUN H. One case of hemlock fruit poisoning[J]. Sichuan Med J(四川医学), 2009, 30(11):1819-1822.
[82]
CHUNJI P, YUNFENG X, LEILIN P, et al. Clinical analysis of acute poisoning of sago seed in 38 cases[J]. Chin Mod Med(中国当代医药), 2014, 21(6):158-159.
[83]
LIU S B, PENG X X, LV J M, et al. The nutritional components and acute toxicity test of Cycas revoluta seed[J]. Acta Nutrim Sin(营养学报), 2010, 32(5):510-512.
[84]
ZHU F. Recent advances in modifications and applications of sago starch[J]. Food Hyd, 2019, 96(00): 412-423.
[85]
LIAO L P, WANG X J, ZHOU H F, et al. Advance on the pharmacological effects of biflavonoids[J]. World Clin Drugs(世界临床药物), 2012, 33(6): 369-374.