View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Springer - Publisher Connector Phytochem Rev (2014) 13:391–416 DOI 10.1007/s11101-014-9349-1 Phytochemistry and bioactivity of aromatic and medicinal plants from the genus Agastache (Lamiaceae) Sylwia Zielińska · Adam Matkowski Received: 31 December 2013 / Accepted: 25 March 2014 / Published online: 3 April 2014 © The Author(s) 2014. This article is published with open access at Springerlink.com Abstract Agastache is a small genus of Lamiaceae, various extracts or individual compounds in vitro and comprising 22 species of perennial aromatic medicinal in vivo include antimicrobial, antiviral and anti- herbs. In this article, we review recent advances in mutagenic activity, cytotoxic activity to cancer cell phytochemical, pharmacological, biotechnological lines, and anti-nociceptive, anti-inflammatory, anti- and molecular research on Agastache. The phytochem- atherogenic, antioxidant as well as biocidal activity to ical profile of all Agastache species studied to date is several foodstuff pests. Biotechnological and molec- generally similar, consisted of two main metabolic ular studies have focused on in vitro propagation and classes—phenylpropanoids and terpenoids. In the enhancing the biosynthesis of bioactive metabolites in relatively variable essential oils, most populations of cell or organ cultures, as well as on the expression of different Agastache species contain over 50 % of a genes involved in phenolic biosynthesis. phenylallyl compound—estragole. Also, other volatile compounds (methyleugenol, pulegone, menthone, Keywords Essential oil · Estragole · isomenthone and spathulenol) were reported in various Giant hyssop · Phenylpropanoids · proportions. Major non-volatile metabolites belong to Tilianin phenolic compounds, such as caffeic acid derivatives, especially rosmarinic acid as well as several flavones and flavone glycosides like acacetin, tilianin, agasta- Introduction choside, and a rare dimeric malonyl flavone (agastachin). Two unique lignans—agastenol and Throughout the world, hundreds of Lamiaceae (Mint agastinol—were also isolated. Terpenoids include family) species are used as medicinal and aromatic triterpenoids of oleanane-type (maslinic acid, olean- plants. Some of them are among the most popular olic acid and β-amyrin), ursane-type (ursolic acid, spices and herbs, like basil, peppermint, sage, and corosolic acid and α-amyrin), and typical plant sterols, many others. Here, we would like to portray one as well as abietane-type oxidized diterpenes (e.g., genus—Agastache Clayt. ex Gronov.—that has sim- agastaquinone, agastol, and others). The bioactivity of ilar properties but which is not as commonly recognized. Plants from this genus are known under the vernacular name ‘giant hyssop’. Some of these S. Zielińska · A. Matkowski (&) plants are utilized as a source of essential oil, herbal Department of Pharmaceutical Biology and Botany, drugs, spice, nectariferous plants in beekeeping, or as Medical University of Wroclaw, Borowska 211, 50-556 Wroclaw, Poland ornamentals. Their ornamental use is actually the e-mail: [email protected] most common, making giant hyssops one of a few 123 392 Phytochem Rev (2014) 13:391–416 examples in the mint family where decorative value sections: Brittonastrum and Agastache (Lint and appears to overshadow its potential as a medicinal Epling 1945; Sanders 1987). plant. Almost 16 years have passed since the last (and Plants from Agastache genus are perennial herbs, only) systematic review of the Agastache genus was reaching one meter or more in height. The stems can be published (Fuentes-Granados et al. 1998). Since then, simple or branched, erect or slightly creeping, and with significant progress in biological investigations has an occasionally woody stem base. Their morphology is been made. Apart from the morphological, cytoge- typical for Lamiaceae, with opposite petiolate leaves, a netical, taxonomic, horticultural and biochemical four-angled stem, numerous trichomes and labiate research that has been previously described, several flowers with pink, purple, white, yellowish or orange important biotechnological and molecular studies of corolla. The base chromosome number is 9. Agastache Agastache species have appeared in the meantime. species are native to North America, but one species As a result of increasing interest in ethnic and occurs naturally in East Asia (A. rugosa). Several traditional phytotherapeutics, many new studies have species are cultivated as ornamentals, with numerous been undertaken to examine the pharmacological spectacular blooming cultivars. According to the properties of these herbs, including a few Agastache current listing by the taxonomical Internet database species. So far, only a few species of the genus lead by the Royal Botanical Gardens at Kew and the Agastache have been fairly represented in the phy- Missouri Botanical Garden (www.theplantlist.org— tochemical and pharmacological literature. Even so, accessed 31 December 2013), the genus Agastache the available data sufficiently support the prospect of encompasses the following 29 accepted taxons: increasing use of Agastache spp. and their constitu- ents in herbal therapy. A. aurantiaca (A.Gray) Lint & Epling In the present review, we discuss recent advances A. breviflora (A.Gray) Epling in the phytochemistry, bioactivity, molecular biology A. cana (Hook.) Wooton & Standl. and biotechnology of Agastache, with an emphasis on A. coccinea (Greene) Lint & Epling the following species: A. foeniculum, A. mexicana, A. A. cusickii (Greenm.) A.Heller rugosa, A. scrophulariifolia and A. urticifolia. How- A. eplingiana R.W.Sanders ever, informations about other species are also A. foeniculum (Pursh) Kuntze considered upon their availability in the literature. A. mearnsii Wooton & Standl. For a comprehensive literature overview, we ana- A. mexicana (Kunth) Lint & Epling lyzed the published phytochemical and pharma- A. mexicana subsp. mexicana (an infraspecific cological data available through several search engines, taxon) such as ®SciFinder, ISI ®Web of Science, ®Scopus and A. micrantha (A.Gray) Wooton & Standl. ®GoogleScholar, using ‘Agastache’ as the search key- A. nepetoides (L.) Kuntze word. We disregarded publications pertaining to A. occidentalis (Piper) A.Heller agronomy, plant pathology, ecology and other unrelated A. pallida (Lindl.) Cory topics (unless any phytochemical or pharmacological A. pallida var. pallida (an infraspecific taxon) data were provided in them). In a few cases, we found A. pallidiflora (A.Heller) Rydb. publications using bibliographical data from the refer- A. pallidiflora var. greenei (Briq.) R.W.Sanders ence lists of newer papers to verify the cited A. pallidiflora var. harvardii (A.Gray) R.W. information. The major portion of the retrieved citations Sanders came from years following the previous review paper of A. pallidiflora subsp. neomexicana (Briq.) Lint & 1998 (Fuentes-Granados et al. 1998). Epling A. palmeri (B.L.Rob.) Standl. A. palmeri var. breviflora (Regel) R.W.Sanders Botanical description A. parvifolia Eastw. A. pringlei (Briq.) Lint & Epling The genus Agastache belongs to the Nepetoideae—a A. pringlei var. verticillata (Wooton & Standl.) R. subfamily of the Lamiaceae (Cantino et al. 1992). W.Sanders The species of Agastache can be separated into two A. rugosa (Fisch. & C.A.Mey.) Kuntze 123 Phytochem Rev (2014) 13:391–416 393 A. rupestris (Greene) Standl. The morphology of leaf laminas as well as stem- A. scrophulariifolia (Willd.) Kuntze types and inflorescence were described in detail in A. urticifolia (Benth.) Kuntze Fuentes-Granados et al.’s review (1998) and some A. wrightii (Greenm.) Wooton & Standl. earlier papers (Lint and Epling 1945; Vogelmann 1985; Sanders 1987). Generally, the leaves of plants However, the number of Agastache species recog- from the Agastache section are longer (up to 15 cm) nized has not been constant, and several of them have than those of Brittonastrum (2–6 cm). Plants from the moved taxonomical positions throughout the years Agastache section have ovate laminas with a crenate- (Lint and Epling 1945; Vogelmann 1985; Sanders serrate leaf margin, whereas those of Brittonastrum 1987; Fuentes-Granados et al. 1998; RBG Kew—the are more diverse. In the latter section, the basic leaf plant list web-based resource, accessed 31 December form is cordate-triangular, but juvenile laminas are 2013). In 1945, 22 taxa of Agastache were reported ovate-to-cordate and mature—cordate, ovate, nar- (Lint and Epling 1945), divided into two sections: rowly ovate or oblong-linear. Leaf margins are Brittonastrum and Chiastandra (synonymous with usually crenate, sometimes entire (Sanders 1987). currently recognized section Agastache). Brittona- The stems of plants from the Agastache section are strum was described as native to the southwestern simple or else branched with dense spicate inflores- United States and Mexico, while Chiastandra was cences formed at terminal apices (Lint and Epling described in relation to the northern part of the United 1945). The inflorescence of Brittonastrum plants is States, Canada and East Asia (Lint and Epling 1945). basically an elongate thyrse. However, in various Later, one more species was recognized (A. eplingi- species and environmental conditions, it can be either ana) in an extensive taxonomic study of continuous and spike-like-to-brush-like or else dis- Brittonastrum (Sanders 1987), two more were sepa- continuous and moniliform-to-loosely