Structural classification and biological activities of Stemona alkaloids

Springer Science and Business Media LLC - Tập 18 Số 2 - Trang 463-493 - 2019
Harald Greger1
1Chemodiversity Research Group, Faculty of Life Sciences, University of Vienna, Rennweg 14, 1030, Vienna, Austria

Tóm tắt

Từ khóa


Tài liệu tham khảo

Alibés R, Figueredo M (2009) Strategies for the synthesis of Stemona alkaloids. Eur J Org Chem 15:2421–2435

Asano N, Yamauchi T, Kagamifuchi K, Shimizu N, Takahashi S, Takatsuka H, Ikeda K, Kizu H, Chuakul W, Kettawan A, Okamoto T (2005) Iminosugar-producing Thai medicinal plants. J Nat Prod 68:1238–1242

Bacher M, Hofer O, Brader G, Vajrodaya S, Greger H (1999) Thapsakins: possible biogenetic intermediates towards insecticidal cyclopenta[b]benzofurans from Aglaia edulis. Phytochemistry 52:253–263

Baird MC, Pyne SG, Ung AT, Lie W, Sastraruji T, Jatisatienr A, Jatisatienr C, Dheeranupattana S, Lowlam J, Boonchalermkit S (2009) Semisynthesis and biological activity of stemofoline alkaloids. J Nat Prod 72:679–684

Brader G, Vajrodaya S, Greger H, Bacher M, Kalchhauser H, Hofer O (1998) Bisamides, lignans, triterpenes, and insecticidal cyclopenta[b]benzofurans from Aglaia species. J Nat Prod 61:1482–1490

Brem B, Seger C, Pacher T, Hofer O, Vajrodaya S, Greger H (2002) Feeding deterrence and contact toxicity of Stemona alkaloids—a source of potent natural insecticides. J Agric Food Chem 50:6383–6388

Brem B, Seger C, Pacher T, Hartl M, Hadacek F, Hofer O, Vajrodaya S, Greger H (2004) Antioxidant dehydrotocopherols as a new chemical character of Stemona species. Phytochemistry 65:2719–2729

Brito GA, Pirovani RV (2018) Stemoamide: total and formal synthesis. A review. Org Prep Proc Int 50:245–259

But PPH, Shaw PC, Lin G, Jiang RW, Xu YT (2012) Authentication and quality assesssment of the antitussive herb Baibu (Radix Stemonae). In: Shyur LF, Lau ASY (eds) Advances in Botanical Research, vol 62. Elsevier, Amsterdam

Cai XH, Luo XD (2007) Alkaloids from Stemona mairei. Planta Med 73:170–173

Chaiyong S, Jatisatienr A, Mungkornasawakul P, Sastraruji T, Pyne SG, Ung AT, Urathamakul T, Lie W (2010) Phytochemical investigations of Stemona curtisii and synthetic studies on stemocurtisine alkaloids. J Nat Prod 73:1833–1838

Chanmahasathien W, Ampasavate C, Greger H, Limtrakul P (2011a) Stemona alkaloids, from traditional Thai medicine, increase chemosensitivity via P-glycoprotein-mediated multidrug resistance. Phytomedicine 18:199–204

Chanmahasathien W, Ohnuma S, Ambudkar SV, Limtrakul P (2011b) Biochemical mechanism of modulation of human P-glycoprotein by stemofoline. Planta Med 77:1990–1995

Chen G, Brecker L, Felsinger S, Cai XH, Kongkiatpaiboon S, Schinnerl J (2017) Morphological and chemical variation of Stemona tuberosa from southern China—evidence for heterogeneity of this medicinal plant species. Plant Biol 19:835–842

Chen G, Brecker L, Sandler KM, Cai XH, Kongkiatpaiboon S, Valant-Vetschera K, Schinnerl J (2018) Phytochemical characterization of the Chinese endemic species Stemona mairei and five other Stemona species. Phytochem Lett 28:168–173

Cheng DL, Guo J, Chu TT, Röder E (1988) A study of Stemona alkaloids, III. Application of 2D-NMR spectroscopy in the structure determination of stemoninine. J Nat Prod 51:202–211

Cheng Z, Yue L, Zhao WH, Yang XH, Shu GW (2015) Protective effects of protostemonine on LPS/GalN-induced acute liver failure: roles of increased hepatic expression of heme oxygenase 1. Int Immunopharmacol 29:798–807

Chung HS, Hon PM, Lin G, But PPH, Dong H (2003) Antitussive activity of Stemona alkaloids from Stemona tuberosa. Planta Med 69:914–920

Cui YX, Lin WH (1998) 2D NMR studies on tuberostemoenone and tuberostemonone. Chin J Magn Res 15:515–520

Dong W, Wang P, Meng XC, Sun H, Zhang A, Wang WM, Dong H, Wang XJ (2012) Ultra-performance liquid chromatography-high-definition mass spectrometry analysis of constituents in the root of Radix Stemonae and those absorbed in blood after oral administration of the extract of the crude drug. Phytochem Anal 23:657–667

Dong JL, Yang ZD, Zhou SY, Yu HT, Yu HT, Yao XJ, Xue HY, Shu ZM (2017) Two Stemona alkaloids from Stemona sessilifolia (Miq.) Miq. Phytochem Lett 19:259–262

Edwards OE, Feniak G, Handa KL (1962) The alkaloids of Stemona sessilifolia. Can J Chem 40:455–462

Frankowski KJ, Neuenswander B, Aubé J (2008) Explorations of Stemona alkaloid-inspired analogues: skeletal modification and functional group diversification. J Comb Chem 10:721–725

Frankowski KJ, Setola V, Evans JM, Neuenswander B, Roth BL, Aubé J (2011) Synthesis and receptor profiling of Stemona alkaloid analogues reveal a potent class of sigma ligands. Proc Natl Acad Sci USA 108:6727–6732

Fukaya H, Hitotsuyanagi Y, Aoyagi Y, Shu Z, Komatsu K, Takeya K (2013) Absolute structures of stemona-lactam S and tuberostemospiroline, alkaloids from Stemona tuberosa. Chem Pharm Bull 61:1085–1089

Gao Y, Wang J, Zhang CF, Xu XH, Zhang M, Kong LY (2014) Seven new alkaloids from the roots of Stemona tuberosa. Tetrahedron 70:967–974

Ge F, Ke CQ, Tang W, Yang XZ, Tang CP, Qin GW, Xu RS, Li TX, Chen XW, Zuo JP, Ye Y (2007) Isolation of chlorogenic acids and their derivatives from Stemona japonica by preparative HPLC and evaluation of their anti-AIV (H5N1) activity in vitro. Phytochem Anal 18:213–218

Götz M, Bögri T, Gray AH, Strunz GM (1968) The structure of tuberostemonine. Tetrahedron 24:2631–2643

Greger H (2006) Structural relationships, distribution and biological activities of Stemona alkaloids. Planta Med 72:99–113

Greger H (2012) The diversity of Stemona stilbenoids as a result of storage and fungal infection. J Nat Prod 75:2261–2268

Greger H, Zechner G, Hofer O, Vajrodaya S (1996) Bioactive amides from Glycosmis species. J Nat Prod 59:1163–1168

Greger H, Schinnerl J, Vajrodaya S, Brecker L, Hofer O (2009) Pandanus alkaloids in Stemonaceae: finding of a plausible biogenetic origin of Stemona alkaloids. J Nat Prod 72:1708–1711

Guo A, Jin L, Deng ZW, Cai SQ, Guo SX, Lin WH (2008) New Stemona alkaloids from the roots of Stemona sessilifolia. Chem Biodivers 5:598–605

Guo J, He HP, Li SL, Hua HM, Hao XJ (2010) A new alkaloid from the roots of Stemona tuberosa (Stemonaceae). Acta Bot Yunnanica 32:163–165

Han H, Yang L, Ding Y, Ji G, Zhang T (2016) Pharmacokinetics and metabolism profiles of protostemonine in rat by liquid chromatography combined with electrospray ionization tandem mass spectrometry. J Pharm Biomed Anal 117:266–275

Harada H, Irie H, Masaki N, Osaki K, Uyeo S (1967) The stereochemistry and absolute configuration of stenine and tuberostemonine. Chem Commun. https://doi.org/10.1039/c19670000460

Hartl M, Kiehn M (2004) Chromosome numbers and other karyological data of four Stemona species (Stemonaceae) from Thailand. Blumea 49:457–460

Hitotsuyanagi Y, Hikita M, Oda T, Kakuta D, Fukaya H, Takeya K (2007a) Structures of four new alkaloids from Stemona sessilifolia. Tetrahedron 63:1008–1013

Hitotsuyanagi Y, Hikita M, Nakada K, Fukaya H, Takeya K (2007b) Sessilifoliamide I, a new alkaloid from Stemona sessilifolia. Heterocycles 71:2035–2040

Hitotsuyanagi Y, Takeda E, Fukaya H, Takeya K (2008) Sessilifoliamine A and sessilifoliamide J: new alkaloids from Stemona sessilifolia. Tetrahedron Lett 49:7376–7379

Hitotsuyanagi Y, Uemura G, Takeya K (2010) Sessilifoliamides K and L: new alkaloids from Stemona sessilifolia. Tetrahedron Lett 51:5694–5696

Hitotsuyanagi Y, Hikita M, Uemura G, Fukaya H, Takeya K (2011) Structures of stemoxazolidinones A-F, alkaloids from Stemona sessilifolia. Tetrahedron 67:455–461

Hitotsuyanagi Y, Fukaya H, Takeda E, Matsuda S, Saishu Y, Zhu S, Komatsu K, Takeya K (2013a) Structures of stemona-amine B and stemona-lactams M-R. Tetrahedron 69:6297–6304

Hitotsuyanagi Y, Shigemori G, Fukaya H, Hikita M, Zhu S, Komatsu K, Takeya K (2013b) Stemona-amines C-E, new alkaloids from Stemona tuberosa. Tetrahedron Lett 54:6995–6998

Hitotsuyanagi Y, Sekiya Y, Fukaya H, Park HS, Zhu S, Komatsu K (2016) Stemona-amines F and G, new alkaloids from Stemona tuberosa. Tetrahedron Lett 57:5746–5749

Hofer O, Greger H (2000) Sulfur-containing amides from Glycosmis species (Rutaceae). In: Herz W, Falk H, Kirby GW, Moore RE (eds) Progress in the chemistry of organic natural products. Springer, New York

Hosoya T, Yamasaki F, Nakata A, Rahman A, Kusumawati I, Zaini NC, Morita H (2011) Inhibitors of nitric oxide production from Stemona javanica. Planta Med 77:256–258

Hu JP, Yang DH, Lin WH, Cai SQ (2009) Alkaloids from the roots of Stemona tuberosa. Helv Chim Acta 92:2125–2133

Huang SZ, Kong FD, Ma QY, Guo ZK, Zhou LM, Wang Q, Dai HF, Zhao YX (2016) Nematicidal Stemona alkaloids from Stemona parviflora. J Nat Prod 79:2599–2605

Huber CP, Hall SR, Maslen EN (1968) The crystal structure of oxotuberostemonine. Tetrahedron Lett 4081-4084

Iizuka H, Irie H, Masaki N, Osaki K, Uyeo S (1973) X-ray crystallographic determination of the structure of stemonamine, a new alkaloid from Stemona japonica Miq.: isolation of isostemonamine. J Chem Soc Chem Comm. https://doi.org/10.1039/c39730000125

Inthachub P, Vajrodaya S, Duyfjes BEE (2009) Review of the genus Stichoneuron (Stemonaceae). Edinb J Bot 66:213–228

Inthachub P, Vajrodaya S, Duyfjes BEE (2010) Census of Stemona (Stemonaceae) in Thailand. Blumea 55:143–152

Irie H, Harada H, Ohno K, Mizutani T, Uyeo S (1970a) The structure of the alkaloid protostemonine. J Chem Soc D Chem Comm. https://doi.org/10.1039/c29700000268

Irie H, Masaki N, Ohno K, Osaki K, Taga T, Uyeo S (1970b) The crystal structure of a new alkaloid, stemofoline, from Stemona japonica. Chem Comm 17:1066

Ji ZH, Duyfjes BEE (2000) Stemonaceae. In: Wu ZY, Raven PH (eds) Flora of China, vol 24. Science Press, Beijing

Jiang RW, Hon PM, But PPH, Chung HS, Lin G, Ye WC, Mak TCW (2002) Isolation and stereochemistry of two new alkaloids from Stemona tuberosa. Tetrahedron 58:6705–6712

Jiang RW, Hon PM, Xu YT, Chan YM, Xu HX, Shaw PC, But PPH (2006a) Isolation and chemotaxonomic significance of tuberostemospironine-type alkaloids from Stemona tuberosa. Phytochemistry 67:52–57

Jiang RW, Hon PM, Zhou Y, Chan YM, Xu YT, Xu HX, Greger H, Shaw PC, But PPH (2006b) Alkaloids and chemical diversity of Stemona tuberosa. J Nat Prod 69:749–754

Jiwajinda S, Hirai N, Watanabe K, Santisopasri V, Chuengsamarnyart N, Koshimizu K, Ohigashi H (2001) Occurrence of the insecticidal 16,17-didehydro-16(E)-stemofoline in Stemona collinsae. Phytochemistry 56:693–695

Jung KH, Kil YS, Jung J, Park S, Shin D, Lee K, Seo EK, Bae H (2016) Tuberostemonine N, an active compound isolated from Stemona tuberosa, suppresses cigarette smoke-induced sub-acute lung inflammation in mice. Phytomedicine 23:79–86

Kakuta D, Hitotsuyanagi Y, Matsuura N, Fukaya H, Takeya K (2003) Structures of new alkaloids sessilifoliamides A-D from Stemona sessilifolia. Tetrahedron 59:7779–7786

Kaltenegger E, Brem B, Mereiter K, Kalchhauser H, Kählig H, Hofer O, Vajrodaya S, Greger H (2003) Insecticidal pyrido[1,2-a]azepine alkaloids and related derivatives from Stemona species. Phytochemistry 63:803–816

Ke CQ, He ZS, Yang YP, Ye Y (2003) A novel alkaloid from Stemona parviflora. Chin Chem Lett 14:173–175

Kil YS, Han AR, Seo EK (2014) Tuberostemonin O from the roots of Stemona tuberosa. Bull Korean Chem Soc 35:1891–1893

Kondo H, Satomi M, Odera T (1954) Stemona alkaloids. XVI. Alkaloid from root of Stemona tuberosa. Ann Rept ITSUU Lab 5:99–102

Kongkiatpaiboon S, Schinnerl J, Felsinger S, Keeratinijakal V, Vajrodaya S, Gritsanapan W, Brecker L, Greger H (2011) Structural relationships of Stemona alkaloids: assessment of species-specific accumulation trends for exploiting their biological activities. J Nat Prod 74:1931–1938

Kongkiatpaiboon S, Mikulicic S, Keeratinijakal V, Greger H, Gritsanapan W (2013) HPLC simultaneous analysis for quality assessment of Stemona curtisii roots and determination of their insecticidal activities. Ind Crops Prod 43:648–653

Kostecki K, Engelmeier D, Pacher T, Hofer T, Vajrodaya S, Greger H (2004) Dihydrophenanthrenes and other antifungal stilbenoids from Stemona cf. pierrei. Phytochemistry 65(1):99–106

Koyama H, Oda K (1970) Crystal and molecular structure of stemonine hydrobromide hemihydrate. J Chem Soc B Phys Org. https://doi.org/10.1039/j29700001330

Lai DH, Yang ZD, Xue WW, Sheng J, Shi Y, Yao XJ (2013) Isolation, characterization and acetylcholinesterase inhibitory activity of alkaloids from roots of Stemona sessilifolia. Fitoterapia 89:257–264

Lee KY, Jeong EJ, Sung SH, Kim YC (2016) Stemona alkaloids isolated from Stemona tuberosa roots and their inhibitory activity on lipopolysaccharide-induced nitric oxide production. Rec Nat Prod 10:109–112

Leung PHH, Zhang L, Zuo Z, Lin G (2006) Intestinal absorption of Stemona alkaloids in a CaCo-2 cell model. Planta Med 72:211–216

Li EX, Fu CX (2007) A new synonym of Stemona sessilifolia (Stemonaceae). Acta Phytotax Sin 45:399–402

Li SL, Jiang RW, Hon PM, Cheng L, Xu HX, Greger H, But PPH, Shaw PC (2007a) Quality evaluation of Radix Stemonae through simultaneous quantification of bioactive alkaloids by high-performance liquid chromatography coupled with diode array and evaporative light scattering detectors. Biomed Chromatogr 21:1088–1094

Li ZX, Sturm S, Stuppner H, Schraml E, Moser VA, Siegl V, Pfragner R (2007b) The dichloromethane fraction of Stemona tuberosa Lour inhibits tumor cell growth and induces apoptosis of human medullary thyroid carcinoma cells. Biol Targets Ther 1:455–463

Li YY, Wang YY, Taniguchi T, Kawakami T, Baba T, Ishibashi H, Mukaida N (2010) Identification of stemonamide synthetic intermediates as a novel potent anticancer drug with an apoptosis inducing ability. Int J Cancer 127:474–484

Lim D, Lee E, Jeong E, Jang VP, Kim J (2015) Stemona tuberosa prevented inflammation by suppressing the recruitment and the activation of macrophages in vivo and in vitro. J Ethnopharmacol 160:41–51

Limtrakul P, Siwanon S, Yodkeeree S, Duangrat C (2007) Effect of Stemona curtisii root extract on P-glycoprotein and MRP-1 function in multidrug-resistant cancer cells. Phytomedicine 14:381–389

Lin WH, Fu HZ (1999) Three new alkaloids from the roots of Stemona tuberosa. J Chin Pharm Sci 8:1–7

Lin WH, Yin BP, Tang ZJ, Xu RS, Zhong QX (1990) The structure of parvistemonine. Acta Chim Sin 48:811–814

Lin WH, Xu RS, Zhong QX (1991a) Chemical studies on Stemona alkaloids I. Studies on new alkaloids of Stemona parviflora Wright C.H. Acta Chim Sin 49:927–931

Lin WH, Xu RS, Zhong QX (1991b) Chemical studies on Stemona alkaloids II. Studies on the minor alkaloids of Stemona parviflora Wright C. H. Acta Chim Sin 49:1034–1037

Lin WH, Ye Y, Xu RS (1991c) Studies on new alkaloids of Stemona mairei. Youji Huaxue 11:500–503

Lin WH, Ye Y, Xu RS (1991d) Studies on new alkaloids of Stemona mairei. Chin Chem Lett 2:369–370

Lin WH, Ye Y, Xu RS (1992) Chemical studies on new Stemona alkaloids, IV. Studies on new alkaloids from Stemona tuberosa. J Nat Prod 55:571–576

Lin WH, Cai MS, Ying BP, Feng R (1993a) Studies on the chemical constituents of Croomia japonica Miq. Acta Pharm Sin 28:202–206

Lin WH, Wang L, Qiao L, Cai MS (1993b) Two minor alkaloids from the roots of Stemona tuberosa L. Chin Chem Lett 4:1067–1070

Lin WH, Ma L, Cai MS, Barnes RA (1994) Two minor alkaloids from roots of Stemona tuberosa. Phytochemistry 36:1333–1335

Lin LG, Zhong QX, Cheng TY, Tang CP, Ke CQ, Lin G, Ye Y (2006) Stemoninines from the roots of Stemona tuberosa. J Nat Prod 69:1051–1054

Lin LG, Tang CP, Dien PH, Xu RS, Ye Y (2007a) Cochinchistemonine, a novel skeleton alkaloid from Stemona cochinchinensis. Tetrahedron Lett 48:1559–1561

Lin LG, Dien PH, Tang CP, Ke CQ, Yang XZ, Ye Y (2007b) Alkaloids from the roots of Stemona cochinchinensis. Helv Chim Acta 90:2167–2175

Lin LG, Li KM, Tang CP, Ke CQ, Rudd JA, Lin G, Ye Y (2008a) Antitussive stemoninine alkaloids from the roots of Stemona tuberosa. J Nat Prod 71:1107–1110

Lin LG, Leung HPH, Zhu JY, Tang CP, Ke CQ, Rudd JA, Lin G, Ye Y (2008b) Croomine- and tuberostemonine-type alkaloids from roots of Stemona tuberosa and their antitussive activity. Tetrahedron 64:10155–10161

Lin LG, Bao H, Wang A, Tang CP, Dien PH, Ye Y (2014) Two new N-oxide alkaloids from Stemona cochinchinensis. Molecules 19:20257–20265

Lind RJ, Greenhow DT, Blythe J, Goodchild J, Hirst E, Dunbar SJ, Earley FGP (2002) Cyanotropanes: novel chemistry interacting at the insect nicotinic acetylcholine receptor. The BCPC conference—pest & diseases 2002. vol 1: 145–152. The British Crop Protection Council

Liu XY, Wang FP (2015) Recent advances in the synthesis of Stemona alkaloids. Nat Prod Commun 10:1093–1102

Manohar A (2013) In silico analysis of compounds from Stemona tuberosa as an inhibitor for N1 neuraminidase of H5N1 avian virus. Braz Arch Biol Technol 56:21–25

Mungkornasawakul P, Pyne SG, Jatisatienr A, Supyen D, Lie W, Ung AT, Skelton BW, White AH (2003) Stemocurtisine, the first pyrido[1,2,-a]azapine Stemona alkaloid. J Nat Prod 66:980–982

Mungkornasawakul P, Pyne SG, Jatisatienr A, Supyen D, Jatisatienr C, Lie W, Ung AT, Skelton BW, White AH (2004a) Phytochemical and larvicidal studies on Stemona curtisii: structure of a new pyrido[1,2-a]azepine Stemona alkaloid. J Nat Prod 67:675–677

Mungkornasawakul P, Pyne SG, Jatisatienr A, Lie W, Ung AT, Issakul K, Sawatwanich A, Supyen D, Jatisatienr C (2004b) Phytochemical studies on Stemona burkillii Prain: two new dihydrostemofoline alkaloids. J Nat Prod 67:1740–1743

Mungkornasawakul P, Chaiyong S, Sastraruji T, Jatisatienr A, Jatisatienr C, Pyne SG, Ung AT, Korth J, Lie W (2009) Alkaloids from the roots of Stemona aphylla. J Nat Prod 72:848–851

Mungkornasawakul P, Pyne SG, Willis AC, Jatisatienr A, Phuthsuk D, Lie W (2013) 6-Hydroxy-5,6-seco-stemocurtisine: a novel seco-stemocurtsine-type alkanoid. Phytochem Lett 6:602–605

Noro T, Fukushima S, Ueno A, Miyase T, Iitaka Y, Saiki Y (1979) A new alkaloid, croomine, from Croomia heterosepala Okuyama. Chem Pharm Bull 27:1495–1497

Oginuma K, Horiuchi K, Fukuhara T (2001) Karyomorphology of two genera in Stemonaceae. Acta Phytotax Geobot 52:57–63

Pacher T, Seger C, Engelmeier D, Vajrodaya S, Hofer O, Greger H (2002) Antifungal stilbenoids from Stemona collinsae. J Nat Prod 65:820–827

Phuwapraisirisan P, Poapolathep A, Poapolathep S, Tip-Pyang S (2006) In vivo oxytoxin antagonistic effects of pyrrolizidine alkaloids from Stemona sp. and Asparagus racemosus. ACGC Chem Res Comm 20:17–19

Pilli RA, Rosso GB, de Oliveira MCF (2010) The chemistry of Stemona alkaloids: an update. Nat Prod Rep 27:1908–1937

Pudjiastuti P, Pyne SG, Sugiyanto Lie W (2012) Isolation of tuberospironine A, a novel croomine derivative from Stemona tuberosa. Phytochem Lett 5:358–360

Qian J, Zhan ZJ (2007) Novel alkaloids from Stemona sessilifolia. Helv Chim Acta 90:326–331

Ramli RA, Lie W, Pyne SG (2013) Alkaloids from the roots and leaves of Stichoneuron halabalensis and their acetylcholinesterase inhibitory activities. Nat Prod Commun 8:695–698

Ramli RA, Lie W, Pyne SG (2014) Alkaloids from the roots of Stichoneuron caudatum and their acetylcholinesterase inhibitory activities. J Nat Prod 77:894–901

Ramli RA, Pudjiastuti P, Tjahjandaric TS, Lie W, Rattanajak R, Kamchonwongapaisan S, Pyne SG (2015) Alkaloids from the roots of Stemona javanica (Kunth.) Engl. (Stemonaceae) and their anti-malarial, acetylcholinesterase inhibitory and cytotoxic activities. Phytochem Lett 11:157–162

Rinner B, Siegl V, Pürstner P, Efferth T, Brem B, Greger H, Pfragner R (2004) Activity of novel plant extracts against medullary thyroid carcinoma cells. Anticancer Res 24:495–500

Sakata K, Aoki K, Chang CF, Sakurai A, Tamura S, Murakoshi S (1978) Stemospironine, a new insecticidal alkaloid of Stemona japonica Miq. Isolation, structural determination and activity. Agric Biol Chem 42:457–463

Sakulpanich A, Attrapadung S, Gritsanapan W (2017) Insecticidal activity of Stemona collinsiae root extract against Parasarcophaga ruficornis (Diptera: Sarcophagidae). Acta Trop 173:62–68

Sastraruji T, Jatisatienr A, Pyne SG, Ung AT, Lie W, Williams MC (2005) Phytochemical studies on Stemona plants: isolation of stemofoline alkaloids. J Nat Prod 68:1763–1767

Sastraruji T, Jatisatienr A, Issakul K, Pyne SG, Ung AT, Lie W, Williams MC (2006) Phytochemical studies on Stemona plants: isolation of new tuberostemonine and stemofoline alkaloids. Nat Prod Commun 1:813–818

Sastraruji K, Pyne SG, Ung AT, Mungkornasawakul P, Lie W, Jatisatienr A (2009) Structural revision of stemoburkilline from an E-alkene to a Z-alkene. J Nat Prod 72:316–318

Sastraruji K, Sastraruji T, Pyne SG, Ung AT, Jatisatienr A, Lie W (2010) Semisynthesis and acetylcholinesterase inhibitory activity of stemofoline alkaloids and analogues. J Nat Prod 73:935–941

Sastraruji T, Chaiyong S, Jatisatienr A, Pyne SG, Ung AT, Lie W (2011) Phytochemical studies on Stemona aphylla: isolation of a new stemofoline alkaloid and six new stemofurans. J Nat Prod 74:60–64

Sastraruji K, Sastraruji T, Ung AT, Griffith R, Jatisatienr A, Pyne SG (2012) Synthesis of stemofoline analogues as acetylcholinesterase inhibitors. Tetrahedron 68:7103–7115

Schinnerl J, Kaltenegger E, Pacher T, Vajrodaya S, Hofer O, Greger H (2005) New pyrrolo[1,2-a]azepine type alkaloids from Stemona and Stichoneuron (Stemonaceae). Monatsh Chem 136:1671–1680

Schinnerl J, Brem B, But PPH, Vajrodaya S, Hofer O, Greger H (2007) Pyrrolo- and pyridoazepine alkaloids as chemical markers in Stemona species. Phytochemistry 68:1417–1427

Seger C, Mereiter K, Kaltenegger E, Pacher T, Greger H, Hofer O (2004) Two pyrrolo[1,2-a]azepine type alkaloids from Stemona collinsae Craib: structure elucidations, relationship to asparagamine A, and a new biogenetic concept of their formation. Chem Biodivers 1:265–279

Sekine T, Ikegami F, Fukasawa N, Kashiwagi Y, Aizawa T, Fujii Y, Ruangrungsi N, Murakoshi I (1995) Structure and relative stereochemistry of a new polycyclic alkaloid, asparagamine A, showing anti-oxytocin activity, isolated from Asparagus racemosus. J Chem Soc Perkin Trans I:391–393

Sun H, Dong W, Zhang A, Wang W, Wang X (2012) Ultra-performance liquid-chromatography with tandem mass spectrometry performing pharmacokinetic and biodistribution studies of croomine, neotuberostemonine and tuberostemonine alkaloids absorbed in the rat plasma after oral administration of Stemonae Radix. Fitoterapia 83:1699–1705

Takayama H, Ichikawa T, Kuwajima T, Kitajima M, Seki H, Aimi N, Nonato MG (2000) Structure characterization, biomimetic total synthesis, and optical purity of two new pyrrolidine alkaloids, pandamarilactonine- A and -B, isolated from Pandanus amaryllifolius Roxb. J Am Chem Soc 122:8635–8639

Takayama H, Ichikawa T, Kitajima M, Aimi N, Lopez D, Nonato MG (2001) A new alkaloid, pandanamine; finding of an anticipated biogenetic intermediate in Pandanus amaryllifolius Roxb. Tetrahedron Lett 42:2995–2996

Tang CP, Chen T, Velten R, Jeschke P, Eppinghaus-Kintscher U, Geibel S, Ye Y (2008) Alkaloids from stems and leaves of Stemona japonica and their insecticidal activities. J Nat Prod 71:112–116

Tsai YC, Yu ML, El-Shazly M, Beerhues L, Cheng YB, Chen LC, Hwang TL, Chen HF, Chung YM, Hou MF, Wu YC, Chang FR (2015) Alkaloids from Pandanus amaryllifolius: isolation and their plausible biosynthetic formation. J Nat Prod 78:2346–2354

Umsumarng S, Pintha K, Pitchakarn P, Sastraruji K, Sastraruji T, Ung AT, Jatisatienr A, Pyne SG, Limtrakul P (2013) Inhibition of P-glycoprotein mediated multidrug resistance by stemofoline derivatives. Chem Pharm Bull 61:399–404

Umsumarng S, Pitchakarn P, Sastraruji K, Yodkeeree S, Ung AT, Pyne SG, Limtrakul P (2015) Reversal of human multi-drug resistance leukaemic cells by stemofoline derivatives via inhibition of P-glycoprotein function. Basic Clin Pharmacol Toxicol 116:390–397

Umsumarng S, Pitchakarn P, Yodkeeree S, Punfa W, Mapoung S, Ramli RA, Pyne SG, Limtrakul P (2017) Modulation of P-glycoprotein by Stemona alkaloids in human multidrug resistance leukemic cells and structural relationships. Phytomedicine 34:182–190

Umsumarng S, Mapoung S, Yodkeeree S, Pyne SG, Limtrakul P (2018) A pharmacological strategy using stemofoline for more efficacious chemotherapeutic treatments against human multidrug resistant leukemic cells. Asian Pac J Cancer Prev 19:3533–3543

Wang FP, Chen QH (2014) Stemona alkaloids: biosynthesis, classification, and biogenetic relationships. Nat Prod Commun 9:1809–1822

Wang P, Liu AL, An Z, Li ZH, Du GH, Qin HL (2007a) Novel alkaloids from the roots of Stemona sessilifolia. Chem Biodivers 4:523–530

Wang P, Qin HL, Li ZH, Liu AL, Du GH (2007b) A new alkaloid from Stemona sessilifolia. Chin Chem Lett 18:152–154

Wang YZ, Tang CP, Dien PH, Ye Y (2007c) Alkaloids from the roots of Stemona saxorum. J Nat Prod 70:1356–1359

Wu YX, He HQ, Nie YJ, Ding YH, Sun L, Qian F (2018) Protostemonine effectively attenuates lipopolysaccharide-induced acute lung injury in mice. Acta Pharmacol Sin 39:85–96

Xiang J, Cheng S, Feng TL, Wu Y, Xie W, Zhang M, Xu XH, Zhang CF (2016) Neotuberostemonine attenuates bleomycin-induced pulmonary fibrosis by suppressing the recruitment and activation of macrophages. Internat Immunopharmacol 36:158–164

Xu RS, Lu YJ, Chu JH, Iwashita T, Naoki H, Naya Y, Nakanishi K (1982) Studies on some new Stemona alkaloids. A diagnostically useful 1H NMR line-broadening effect. Tetrahedron 38:2667–2670

Xu RS, Tang ZJ, Feng SC, Yang YP, Lin WH (1991) Studies on bioactive components from Chinese medicinal plants. Mem Inst Oswaldo Cruz, Rio de Janeiro 86(Suppl II):55–59

Xu YT, Hon PM, Jiang RW, Cheng L, Li SH, Chan YP, Xu HX, Shaw PC, But PPH (2006) Antitussive effects of Stemona tuberosa with different chemical profiles. J Ethnopharmacol 108:46–53

Xu YT, Shaw PC, Jiang RW, Hon PM, Chan YM, But PPH (2010) Antitussive and central respiratory depressant effects of Stemona tuberosa. J Ethnopharmacol 128:679–684

Yang XZ, Zhu JY, Tang CP, Ke CQ, Lin G, Cheng TY, Rudd JA, Ye Y (2009) Alkaloids from roots of Stemona sessilifolia and their antitussive activities. Planta Med 75:174–177

Ye Y, Velten RF (2003) Semi-syntheses of new stemofoline derivatives. Tetrahedron Lett 44:7171–7173

Ye Y, Xu RS (1992) Studies on new alkaloids of Stemona japonica. Chin Chem Lett 3:511–514

Ye Y, Qin GW, Xu RS (1994a) Alkaloids from Stemona tuberosa. Phytochemistry 37:1201–1203

Ye Y, Qin GW, Xu RS (1994b) Alkaloids from Stemona japonica. Phytochemistry 37:1205–1208

Ye Y, Qin GW, Xu RS (1994c) Alkaloids of Stemona japonica. J Nat Prod 57:665–669

Yi M, Xia X, Wu HY, Tian HY, Huang C, But PPH, Shaw PC, Jiang RW (2015) Structures and chemotaxonomic significance of Stemona alkaloids from Stemona japonica. Nat Prod Commun 10:2097–2099

Yue Y, Deng AJ, Xu DS, Qin HL (2013) Two new Stemona alkaloids from Stemona tuberosa Lour. J Asian Nat Prod Res 15:145–150

Yue Y, Deng AJ, Li ZH, Liu AL, Ma L, Zhang ZH, Wang XL, Du GH, Qin HL (2014) New Stemona alklaloids from the roots of Stemona tuberosa. Magn Reson Chem 52:719–728

Zhang RR, Tian HY, Wu Y, Sun XH, Zhang JL, Ma ZG, Jiang RW (2014) Isolation and chemotaxonomic significance of stenine- and stemoninine-type alkaloids from the roots of Stemona tuberosa. Chin Chem Lett 25:1252–1255

Zhong Y, Gao Y, Guo QP, Li WM (2010) Two new alkaloids from Stemona tuberosa. Helv Chim Acta 93:133–138

Zhou Y, Jiang RW, Hon PM, Xu YT, Chan YM, Chan TWD, Xu HX, Ding LS, But PPH, Shaw PC (2006) Analyses of Stemona alkaloids in Stemona tuberosa by liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 20:1030–1038

Zhou X, Leung PHH, Li N, Ye Y, Zhang L, Zuo Z, Lin G (2009) Oral absorption and antitussive activity of tuberostemonine alkaloids from the roots of Stemona tuberosa. Planta Med 75:575–580

Zou CY, Fu HZ, Lei HM, Li J, Lin WH (1999) New alkaloids from the roots of Stemona japonica Miq. J Chin Pharm Sci 8:185–189