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Practical Isolation of Asperuloside from Coprosma quadrifida via Rapid Pressurised Hot Water Extraction

Bianca J. Deans A , Alex C. Bissember A B and Jason A. Smith A B
+ Author Affiliations
- Author Affiliations

A School of Physical Sciences – Chemistry, University of Tasmania, Hobart, Tas. 7001, Australia.

B Corresponding authors. Email: alex.bissember@utas.edu.au; jason.smith@utas.edu.au

Australian Journal of Chemistry 69(11) 1219-1222 https://doi.org/10.1071/CH15743
Submitted: 27 November 2015  Accepted: 1 March 2016   Published: 23 March 2016

Abstract

The valuable glycoside asperuloside was efficiently isolated in multigram quantities from Coprosma quadrifida employing a recently developed rapid pressurised hot water extraction (PHWE) method that utilises an unmodified household espresso machine. This study represents the first time C. quadrifida has been extracted and its major chemical components isolated and analysed. Our findings reveal that this species is a rich source of asperuloside (7.0 % yield w/w). Significantly, this represents one of the highest yields obtained of this glycoside from a Coprosma species, and the entire Rubiaceae family more generally.


References

[1]  (a) H. Herissey, J. Pharm. Chim. 1933, 8, 553.
      (b) L. H. Briggs, G. A. Nicholls, J. Chem. Soc. 1954, 3940.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) L. H. Briggs, J. F. Beachen, R. C. Cambie, N. P. B. Dudman, A. W. Steggles, P. S. Rutledge, J. Chem. Soc., Perkin Trans. 1 1976, 1789.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) L. J. El-Naggar, J. L. Beal, J. Nat. Prod. 1980, 43, 649.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) J. A. Garbarino, V. Gamboro, M. Nicoletti, J. Nat. Prod. 1985, 48, 992.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  (a) T. Hirata, T. Kobayashi, A. Wada, T. Ueda, T. Fujikawa, H. Miyashita, T. Ikeda, S. Tsukamoto, T. Nohara, Bioorg. Med. Chem. 2011, 21, 1786.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjslKjsLg%3D&md5=76be2836384a1bdf20102c3203f6db9aCAS |
      (b) T. Fujikawa, T. Hirata, S. Hosoo, K. Nakajima, A. Wada, Y. Yurugi, H. Soya, T. Matsui, A. Yamaguchi, M. Ogata, S. Nishibe, J. Nutr. Sci. 2012, 1, e10.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  H. G. Vu, K. B. Ninh, X. N. Nguyen, V. K. Phan, C. V. Minh, L. T. A. Hoang, H. Y. Pham, H. T. Bui, X. C. Nguyen, H. N. Nguyen, S. H. Kim, Y.-I. Kwon, Y. H. Kim, Bull. Korean Chem. Soc. 2013, 34, 1555.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  N. Artanti, M. Hanafi, R. Andriyani, V. Saraswati, Z. Udin, P. D. Lotulung, K. I. Fujita, Y. Usuki, Journal of Tropical Life Science 2015, 5, 88.

[5]  (a) M. Bai, W. Shi, J. Tian, M. Lei, J. H. Kim, Y. N. Sun, Y. H. Kim, J. Gao, J. Agric. Food Chem. 2015, 63, 2198.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXis1KnsrY%3D&md5=d69a0997a2ce32574ad9becefeda6ad6CAS | 25679330PubMed |
      (b) J. Qiu, G. Chi, Q. Wu, Y. Ren, C. Chen, H. Feng, Int. J. Immunopharmacol. 2016, 31, 109.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  (a) W. F. Berkowitz, S. C. Choudhry, J. A. Hrabie, J. Org. Chem. 1982, 47, 824.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL38XosFaqsg%3D%3D&md5=0d772cbef3702570483dde730e5a84b0CAS |
      (b) C. Bonini, C. Iavarone, C. Trogolo, R. Di Fabio, J. Org. Chem. 1985, 50, 958.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  (a) A. Venditti, L. Guarcini, M. Ballero, A. Bianco, Plant Syst. Evol. 2015, 301, 685.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtFentrnP&md5=6f6b2e72fe04b12d7efea18030c38948CAS |
      (b) H. Inouye, Y. Takeda, H. Nishimura, A. Kanomi, T. Okuda, C. Puff, Phytochemistry 1988, 27, 2591.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) M. H. Herissey, Bull. Soc. Chim. Biol. (Paris) 1925, 7, 1009.

[8]  V. Plouvier, G. Bertrand, C. R. Hebd. Seances Acad. Sci. 1956, 242, 1643.
         | 1:CAS:528:DyaG28XlvVemtQ%3D%3D&md5=ad27272aac8b83394528c1cd12084ec4CAS |

[9]  The time taken for the Soxhlet extraction of Escallonia philippiana by Plouvier and Bertrand is not provided in ref. [8].

[10]  A. R. Trim, R. Hill, Biochem. J. 1952, 50, 310.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG38XitV2lug%3D%3D&md5=303439c959db9baaa9ab7d66baeff593CAS | 14915951PubMed |

[11]  (a) T. Kanchanapoom, R. Kasai, K. Yamasaki, Phytochemistry 2002, 59, 551.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XhtlCqsLw%3D&md5=ee7b179a5385965b01fcc6d429c9d033CAS | 11853751PubMed |
      (b) N. Ronsted, E. Goebel, H. Franzyk, S. R. Jensen, C. E. Olsen, Phytochemistry 2000, 55, 337.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) H. Kirmizibekmez, C. Bassarello, S. Piacente, G. Akaydin, I. Calis, Z. Naturforsch. B 2009, 64, 252.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) A. Venditti, A. Altieri, A. Bianco, Nat. Prod. Res. 2014, 28, 586.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) C. Takamura, T. Hirata, Y. Yamaguchi, M. Ono, H. Miyashita, T. Ikeda, T. Nohara, J. Nat. Med. 2007, 61, 220.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) U. Ozgen, C. Kazaz, H. Secen, I. Calis, M. Coskun, P. J. Houghton, Turk. J. Chem. 2009, 33, 561.
      (g) P. Noiarsa, S. Ruchirawat, H. Otsuka, T. Kanchanapoom, J. Nat. Med. 2006, 60, 322.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) H. Kirmizibekmez, H. Bardakcıa, M. Masullo, O. Kamburoglu, G. Eryilmaz, G. Akaydin, E. Yesilada, S. Piacente, Helv. Chim. Acta 2014, 97, 1571.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) B. Li, D. Zhang, Y. Luo, X. Chen, Chem. Pharm. Bull. (Tokyo) 2006, 54, 297.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) B. Su, A. D. Pawlus, H. Jung, W. J. Keller, J. L. McLaughlin, A. D. Kinghorn, J. Nat. Prod. 2005, 68, 592.
         | Crossref | GoogleScholarGoogle Scholar |
      (k) P. Noiarsa, Q. Yu, K. Matsunami, H. Otsuka, S. Ruchirawat, T. Kanchanapoo, J. Nat. Med. 2007, 61, 406.
         | Crossref | GoogleScholarGoogle Scholar |
      (l) H. Kirmizibekmez, I. Calis, P. Akbay, O. Sticher, Z. Naturforsch. C 2003, 58, 337.
      (m) S. C. Nunez Montoya, A. M. Agnese, J. L. Cabrera, J. Nat. Prod 2006, 69, 801.
         | Crossref | GoogleScholarGoogle Scholar |
      (n) Y. Takeda, H. Shimidzu, K. Mizuno, S. Inouchi, T. Masuda, E. Hirata, T. Shinzato, M. Aramoto, H. Otsuka, Chem. Pharm. Bull. (Tokyo) 2002, 50, 1395.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  (a) J. Just, B. J. Deans, W. J. Olivier, B. Paull, A. C. Bissember, J. A. Smith, Org. Lett. 2015, 17, 2428.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXnvV2kt70%3D&md5=75673df5f82c0e0dbc2f1083d285ac75CAS | 25938329PubMed |
      (b) J. Just, T. B. Jordan, B. Paull, A. C. Bissember, J. A. Smith, Org. Biomol. Chem. 2015, 13, 11200.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) J. Just, G. L. Bunton, B. J. Deans, N. L. Murray, A. C. Bissember, J. A. Smith, J. Chem. Educ. 2016, 93, 213.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  PHWE is an established technique. For a recent review, see: C. C. Teo, S. N. Tan, J. W. H. Yong, C. S. Huw, E. S. Ong, J. Chromatogr. A 2010, 1217, 2484.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXktVWks7o%3D&md5=ea10952b00e4ee82ba617d0c9f2942e0CAS | 20060531PubMed |

[14]  For sample preparation, a household spice grinder was used to finely process the plant material. The sample compartment of the espresso machine holds ~10 g of ground C. quadrifida leaves. A Breville espresso machine model 800ES was used (available for US ~$300 from retailers such as Amazon). The temperature of water observed in espresso machines is reported to be up to 96°C (with pressures of ~9 bar). See: G. Caprioli, M. Cortese, G. Cristalli, F. Maggi, L. Odello, M. Ricciutelli, G. Sagratini, V. Sirocchi, G. Tomassoni, S. Vittori, Food Chem. 2012, 135, 1127.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtlSmtb%2FL&md5=e5a5f3f9b5d617ba5d6338c4344fc9ebCAS | 22953834PubMed |

[15]  When we performed the Soxhlet extraction of C. quadrifida (10 g) using acetone for 18 h we were ultimately able to isolate asperuloside in 4.5 % yield w/w. An identical sample of C. quadrifida (10 g) provided asperuloside in 4.9 % yield w/w using our PHWE method. Further details can be found in the Supplementary Material.

[16]  This is based upon a recent search of commercial vendors using Scifinder Scholar (8 September 2015).

[17]  (a) J. C. Vieira, L. Mathias, R. Braz-Filho, J. Schripsema, Org. Lett. 1999, 1, 1169.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXmtVOmt7Y%3D&md5=a5c473120dc0f801d6e33b8a42b3d524CAS |
      (b) M. I. Mitova, M. E. Anchev, S. G. Panev, N. V. Handjieva, S. S. Popov, Z. Naturforsch. C 1996, 51, 631.