nach oben

Journal of Natural Medicines

Erschienen in:

26.06.2019 | Original Paper

Chemical components from the twigs of Caesalpinia latisiliqua and their antiviral activity

verfasst von: Mira Oh, SeonJu Park, Jae-Hyoung Song, Hyun-Jeong Ko, Seung Hyun Kim

Erschienen in: Journal of Natural Medicines | Ausgabe 1/2020

Einloggen, um Zugang zu erhalten

Abstract

Three new compounds, (3S)-dihydrobonducellin 8-O-β-d-glucopyranoside (1), 3′,5′-dimethoxy-jezonolid (2), and latisilinoid (3), along with 16 known compounds, were isolated from the twigs of Caesalpinia latisiliqua (Leguminosae). The known compounds were identified as flavonoids, stilbenes, and phenolics as determined by extensive spectroscopic methods, including 1D and 2D NMR. All the isolated compounds were evaluated for their antiviral activity in HRV1B-, CVB3-, and EV71-infected cells. Among the tested compounds, three flavonoids (4–6) and two stilbenes (12 and 14) exhibited significant antiviral activity. This is the first phytochemical investigation of C. latisiliqua twigs.

Nur mit Berechtigung zugänglich

Ban NK, Thoa NTK, Linh TM, Van Kiem P, Nhiem NX, Tai BH, Van Minh C, Song J-H, Ko H-J, Kim SH (2018) Labdane-type diterpenoids from Vitex limonifolia and their antivirus activities. J Nat Med 72:290–297PubMedCrossRef

Brown BA, Oberste MS, Alexander JP, Kennett ML, Pallansch MA (1999) Molecular epidemiology and evolution of enterovirus 71 strains isolated from 1970 to 1998. J Virol 73:9969–9975PubMedPubMedCentralCrossRef

Chen T-C, Weng K-F, Chang S-C, Lin J-Y, Huang P-N, Shih S-R (2008) Development of antiviral agents for enteroviruses. J Antimicrob Chemother 62:1169–1173PubMedCrossRef

Oberste MS, Maher K, Kilpatrick DR, Pallansch MA (1999) Molecular evolution of the human enteroviruses: correlation of serotype with VP1 sequence and application to picornavirus classification. J Virol 73:1941–1948PubMedPubMedCentralCrossRef

Shih S-R, Tsai K-N, Li Y-S, Chueh C-C, Chan E-C (2003) Inhibition of enterovirus 71-induced apoptosis by allophycocyanin isolated from a blue-green alga Spirulina platensis. J Med Virol 70:119–125PubMedCrossRef

Choi HJ, Kim JH, Lee CH, Ahn YJ, Song JH, Baek SH, Kwon DH (2009) Antiviral activity of quercetin 7-rhamnoside against porcine epidemic diarrhea virus. Antivir Res 81:77–81PubMedCrossRef

Chiang LC, Chiang W, Liu MC, Lin CC (2003) In vitro antiviral activities of Caesalpinia pulcherrima and its related flavonoids. J Antimicrob Chemother 52:194–198PubMedCrossRef

Jiang R-W, Ma S-C, He Z-D, Huang X-S, But PP-H, Wang H, Chan S-P, Ooi VE-C, Xu H-X, Mak TCW (2002) Molecular structures and antiviral activities of naturally occurring and modified cassane furanoditerpenoids and friedelane triterpenoids from Caesalpinia minax. Bioorg Med Chem 10:2161–2170PubMedCrossRef

Kalauni SK, Awale S, Tezuka Y, Banskota AH, Linn TZ, Asih PBS, Syafruddin D, Kadota S (2006) Antimalarial activity of cassane-and norcassane-type diterpenes from Caesalpinia crista and their structure–activity relationship. Biol Pharm Bull 29:1050–1052PubMedCrossRef

10.

Kuria KAM, De Coster S, Muriuki G, Masengo W, Kibwage I, Hoogmartens J, Laekeman GM (2001) Antimalarial activity of Ajuga remota Benth (Labiatae) and Caesalpinia volkensii Harms (Caesalpiniaceae): in vitro confirmation of ethnopharmacological use. J Ethnopharmacol 74:141–148PubMedCrossRef

11.

Ma G, Wu H, Chen D, Zhu N, Zhu Y, Sun Z, Li P, Yang J, Yuan J, Xu X (2015) Antimalarial and antiproliferative cassane diterpenes of Caesalpinia sappan. J Nat Prod 78:2364–2371PubMedCrossRef

12.

Gupta M, Mazumder UK, Kumar RS, Kumar TS (2003) Studies on anti-inflammatory, analgesic and antipyretic properties of methanol extract of Caesalpinia bonducella leaves in experimental animal models. Iran J Pharmacol Ther 2:30–34

13.

Wu SQ, Otero M, Unger FM, Goldring MB, Phrutivorapongkul A, Chiari C, Kolb A, Viernstein H, Toegel S (2011) Anti-inflammatory activity of an ethanolic Caesalpinia sappan extract in human chondrocytes and macrophages. J Ethnopharmacol 138:364–372PubMedPubMedCentralCrossRef

14.

Yodsaoue O, Karalai C, Ponglimanont C, Tewtrakul S, Chantrapromma S (2011) Pulcherrins D-R, potential anti-inflammatory diterpenoids from the roots of Caesalpinia pulcherrima. Tetrahedron 67:6838–6846CrossRef

15.

Das B, Srinivas Y, Sudhakar C, Mahender I, Laxminarayana K, Reddy PR, Raju TV, Jakka NM, Rao JV (2010) New diterpenoids from Caesalpinia species and their cytotoxic activity. Bioorg Med Chem Lett 20:2847–2850PubMedCrossRef

16.

Palasap A, Limpaiboon T, Boonsiri P, Thapphasaraphong S, Daduang S, Suwannalert P, Daduang J (2014) Cytotoxic effects of phytophenolics from Caesalpinia mimosoides Lamk. on cervical carcinoma cell lines through an apoptotic pathway. Asian Pac J Cancer Prev 15:449–454PubMedCrossRef

17.

Pawar CR, Mutha RE, Landge AD, Jadhav RB, Surana SJ (2009) Antioxidant and cytotoxic activities of Caesalpinia pulcherrima wood. Indian J Biochem Bio 46:198–200

18.

Lopes N, Faccin-Galhardi LC, Espada SF, Pacheco AC, Ricardo NMPS, Linhares REC, Nozawa C (2013) Sulfated polysaccharide of Caesalpinia ferrea inhibits herpes simplex virus and poliovirus. Int J Biol Macromol 60:93–99PubMedCrossRef

19.

Hozumi T, Matsumoto T, Ooyama H, Namba T, Shiraki K, Hattori M, Kurokawa M, Kadota S (1995) Antiviral agent containing crude drug. US Patent 5,411,733

20.

Ogunlana OO, Ogunlana OE (2015) Antiplasmodial flavonoid from young twigs and leaves of Caesalpinia bonduc (Linn) Roxb. J Chem Pharm Res 7:931–937

21.

Markham KR, Sheppard C, Geiger H (1987) ¹³C NMR studies of some naturally occurring amentoflavone and hinokiflavone bioflavonoids. Phytochemistry 26:3335–3337CrossRef

22.

Burns DC, Ellis DA, March RE (2007) A predictive tool for assessing ¹³C NMR chemical shifts of flavonoids. Magn Reson Chem 45:835–845PubMedCrossRef

23.

Lee EH, Kim HJ, Song YS, Jin C, Lee K-T, Cho J, Lee YS (2003) Constituents of the stems and fruits of Opuntia ficus-indica var. saboten. Arch Pharm Res 26:1018–1023PubMedCrossRef

24.

Markham KR, Ternai B (1976) ¹³C NMR of flavonoids—II: flavonoids other then flavone and flavonol aglycones. Tetrahedron 32:2607–2612CrossRef

25.

Wei Y, Xie Q, Fisher D, Sutherland IA (2011) Separation of patuletin-3-O-glucoside, astragalin, quercetin, kaempferol and isorhamnetin from Flaveria bidentis (L.) Kuntze by elution-pump-out high-performance counter-current chromatography. J Chromatogr A 1218:6206–6211PubMedCrossRef

26.

De Almeida AP, Miranda MMFS, Simoni IC, Wigg MD, Lagrota MHC, Costa SS (1998) Flavonol monoglycosides isolated from the antiviral fractions of Persea americana (Lauraceae) leaf infusion. Phytother Res 12:562–567CrossRef

27.

Yoshida K, Hishida A, Iida O, Hosokawa K, Kawabata J (2008) Flavonol caffeoylglycosides as α-glucosidase inhibitors from Spiraea cantoniensis flower. J Agric Food Chem 56:4367–4371PubMedCrossRef

28.

Lee H-S, Lee B-W, Kim M-R, Jun J-G (2010) Syntheses of resveratrol and its hydroxylated derivatives as radical scavenger and tyrosinase inhibitor. Bull Korean Chem Soc 31:971–975CrossRef

29.

Mattivi F, Reniero F, Korhammer S (1995) Isolation, characterization, and evolution in red wine vinification of resveratrol monomers. J Agric Food Chem 43:1820–1823CrossRef

30.

Jeong C-H, Jeong HR, Choi GN, Kim D-O, Lee UK, Heo HJ (2011) Neuroprotective and anti-oxidant effects of caffeic acid isolated from Erigeron annuus leaf. Chin Med 6:25PubMedPubMedCentralCrossRef

31.

Flamini G, Antognoli E, Morelli I (2001) Two flavonoids and other compounds from the aerial parts of Centaurea bracteata from Italy. Phytochemistry 57:559–564PubMedCrossRef

32.

Gottlieb HE, Kumar S, Sahai M, Ray AB (1991) Ethyl brevifolin carboxylate from Flueggea microcarpa. Phytochemistry 30:2435–2438CrossRef

33.

Hisham DMN, Lip JM, Noh JM, Normah A, Nabilah MFN (2011) Identification and isolation of methyl gallate as a polar chemical marker for Labisia pumila Benth. J Trop Agric Food Sci 39:279–284

34.

Huang L, Ma W, Liu Y, Peng Y, Xiao P (2012) Three New Phenol Compounds from Iris dichotoma Pall. Helv Chim Acta 95:1033–1036CrossRef

35.

Zhao P, Iwamoto Y, Kouno I, Egami Y, Yamamoto H (2004) Stimulating the production of homoisoflavonoids in cell suspension cultures of Caesalpinia pulcherrima using cork tissue. Phytochemistry 65:2455–2461PubMedCrossRef

36.

Wang X-Y, Chen G-R, Deng Z-Y, Zhao J, Ge J-F, Li N, Chen F-H (2014) Chemical constituents from Bidens bipinnata. Zhongguo Zhong Yao Za Zhi 39:1838–1844PubMed

37.

Dai Y, Harinantenaina L, Brodie PJ, Goetz M, Shen Y, TenDyke K, Kingston DG (2013) Antiproliferative homoisoflavonoids and bufatrienolides from Urginea depressa. J Nat Prod 76:865–872PubMedPubMedCentralCrossRef

38.

Wada S-I, Yasui Y, Tokuda H, Tanaka R (2009) Anti-tumor-initiating effects of phenolic compounds isolated from the bark of Picea jezoensis var. jezoensis. Bioorg Med Chem 17:6414–6421PubMedCrossRef

39.

Yu B-B, Han X-Z, Lou H-X (2007) Oligomers of resveratrol and ferulic acid prepared by peroxidase-catalyzed oxidation and their protective effects on cardiac injury. J Agric Food Chem 55:7753–7757PubMedCrossRef

40.

Kurihara H, Kawabata J, Ichikawa S, Mizutani J (1990) (−)-ε-viniferin and related oligostilbenes from Carex pumita Thunb. (Gyperaceae). Agric Biol Chem 54:1097–1099

41.

Ramos F, Takaishi Y, Kashiwada Y, Osorio C, Duque C, Acuña R, Fujimoto Y (2008) Ent-3, 4-seco-labdane and ent-labdane diterpenoids from Croton stipuliformis (Euphorbiaceae). Phytochemistry 69:2406–2410PubMedCrossRef

42.

Ibrahim SRM, Mohamed GA, Al-Musayeib NM (2012) New constituents from the rhizomes of Egyptian Iris germanica L. Molecules 17:2587–2598PubMedPubMedCentralCrossRef

43.

Anjaneyulu AR, Rao VL (2003) Seco diterpenoids from Excoecaria agallocha L. Phytochemistry 62:585–589PubMedCrossRef

44.

Kobayashi M, Ishida K, Terabayashi S, Mitsuhashi H (1991) 10-Hydroxypheophytins and a new norlabdane diterpene from the leaves of Cupressus funebris ENDL. Chem Pharm Bull 39:3348–3349CrossRef

Titel: Chemical components from the twigs of Caesalpinia latisiliqua and their antiviral activity
verfasst von: Mira Oh
SeonJu Park
Jae-Hyoung Song
Hyun-Jeong Ko
Seung Hyun Kim
Publikationsdatum: 26.06.2019
Verlag: Springer Singapore
Erschienen in: Journal of Natural Medicines / Ausgabe 1/2020
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-019-01335-2

Live-Webinar: Aktuelle Leitlinien bei Herz-Kreislauf-Erkrankungen

Springer Medizin

Chemical components from the twigs of Caesalpinia latisiliqua and their antiviral activity

Abstract

Live-Webinar: Aktuelle Leitlinien bei Herz-Kreislauf-Erkrankungen

Springer Medizin

Abstract

Bitte loggen Sie sich ein, um Zugang zu diesem Inhalt zu erhalten

Weitere Artikel der Ausgabe 1/2020

Serine protease inhibitors and activators from Dalbergia tonkinensis species

Carotenoids as natural functional pigments

Inhibitory activities of kukoamines A and B from Lycii Cortex on amyloid aggregation related to Alzheimer’s disease and type 2 diabetes

The combination of ITS2 and psbA-trnH region is powerful DNA barcode markers for authentication of medicinal Terminalia plants from Thailand

Selective cytotoxicity of epidithiodiketopiperazine DC1149B, produced by marine-derived Trichoderma lixii on the cancer cells adapted to glucose starvation

Species identification of Indonesian agarwood using a DNA-barcoding method