Abstract
A quantitative 1H-NMR method (qHNMR) was used to measure the amygdalin content of Persicae semen, Armeniacae semen, and Mume fructus, in each of which amygdalin constitutes a major component. The purity of amygdalin was calculated from the ratio of the intensity of the amygdalin H-2 signal at δ 6.50 ppm in pyridine-d 5 to that of the hexamethyldisilane (HMD) signal at 0 ppm. The HMD concentration was corrected by the International System of Units (SI) traceability with certified reference material (CRM)-grade bisphenol A. qHNMR revealed the amygdalin contents to be 2.72 and 3.13 % in 2 lots of Persicae semen, 3.62 and 5.19 % in 2 lots of Armeniacae semen, and 0.23 % in Mume fructus. Thus, we demonstrated the utility of this method for the quantitative analysis of crude drugs.
References
Fukuda T, Ito H, Yoshida T (2003) Glycosides and their quantitative HPLC analysis of commercial Persicae semen. Nat Med 57(1):18–22
Miyagoshi M, Amagaya S, Ogihara Y (1986) Antitussive effects of L-ephedrine, amygdalin, and Makyokansekito (Chinese traditional medicine) using a cough model induced by sulfur dioxide gas in mice. Planta Med 52(4):275–278
Hwang H-J, Kim P, Kim C-J, Lee HJ, Shim I, Yin CS, Yang Y, Hahm DH (2008) Antinociceptive effect of amygdalin isolated from Prunus armeniaca on formalin-induced pain in rats. Biol Pharm Bull 31:1559–1564
Fukuda T, Ito H, Mukainaka T, Tokuda H, Nishino H, Yoshida T (2003) Anti-tumor promoting effect of glycosides from Prunus persica seeds. Biol Pharm Bull 26:271–273
Mirmiranpour H, Khaghani S, Zandieh A, Khalilzadeh OO, Gerayesh-Nejad S, Morteza A, Esteghamati A (2012) Amygdalin inhibits angiogenesis in the cultured endothelial cells of diabetic rats. Indian J Pathol Microbiol 55:211–214
Chang HK, Shin MS, Yang HY, Lee JW, Kim YS, Lee MH, Kim J, Kim KH, Kim CJ (2006) Amygdalin induces apoptosis through regulation of Bax and Bcl-2 expressions in human DU145 and LNCap prostate cancer cells. Biol Pharm Bull 29:1597–1602
Ministry of Health and Welfare (2000) The Japanese Pharmacopoeia, 15th edn. Japan, pp 1223–1224
Pauli GF, Jaki BU, Lankin DC (2005) Quantitative 1H NMR: development and potential of a method for natural products analysis. J Nat Prod 68:133–149
Tahara M, Sugimoto N, Suematsu T, Arifuku K, Saito T, Ihara T, Yoshida Y, Tada A, Kubota R, Shimizu K, Yamazaki T, Tanamoto K, Nakazawa H, Nishimura T (2009) Quality control of organophosphorus pesticide isoxathion oxon based on qNMR. Jpn J Food Chem Safety 16:28–33
Hasada K, Yoshida T, Yamazaki T, Sugimoto N, Nishimura T, Nagatsu A, Mizukami H (2010) Quantitative determination of atractylon in Atractylodis Rhizoma and Atractylodis Lanceae Rhizoma by 1H-NMR spectroscopy. J Nat Med 64:161–166
Hasada K, Yoshida T, Yamazaki T, Sugimoto N, Nishimura T, Nagatsu A, Mizukami H (2011) Application of 1H-NMR spectroscopy to validation of berberine alkaloid reagents and to chemical evaluation of Coptidis Rhizoma. J Nat Med 65:262–267
Tanaka R, Yamazaki M, Hasada K, Nagatsu A (2012) Application of quantitative 1H-NMR method to determination of paeoniflorin in Paeoniae radix. J Nat Med (in press)
Saito T, Ihara T, Koike M, Kinugasa S, Fujimine Y, Nose K, Hirai T (2009) A new traceability scheme for the development of international system-traceable persistent organic pollutant reference materials by quantitative nuclear magnetic resonance. Accred Qual Assur 14:79–86
Ministry of Health and Welfare (2011) The Japanese Pharmacopeia, 16th edn. Japan, pp 1480–1481
Seigler DS, Pauli GF, Nahrstedt A, Leen R (2002) Cyanogenic allosides and glucosides from Passiflora edulis and Carica papaya. Phytochemistry 60(8):873–882
Someya K, Mikoshiba S, Okumura T, Takenaka H, Ohdera M, Shirota O, Kuroyanagi M (2006) Suppressive effect of constituents isolated from kernel of Prunus armeniaca on 5 α-androst-16-en-3-one generated by microbial metabolism. J Oleo Sci 55(7):353–364
Cervellati C, Paetz C, Dondini L, Tartarini S, Bassi D, Schneider B, Masia A (2012) A qNMR approach for bitterness phenotyping and QTL identification in an F1 apricot progeny. J Biotechnol 159:312–319
Acknowledgments
We thank Dr. N Sugimoto of the National Institute of Health Sciences for his kind advice on the measurements by qHNMR.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Tanaka, R., Nitta, A. & Nagatsu, A. Application of a quantitative 1H-NMR method for the determination of amygdalin in Persicae semen, Armeniacae semen, and Mume fructus. J Nat Med 68, 225–230 (2014). https://doi.org/10.1007/s11418-013-0783-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11418-013-0783-y