A new iridoid from Adenosma caeruleum R. Br. Maryan Bruzual De Abreu a , Nicola Malafronte b , Phan Van Kiem c , Alessandra Braca a, ⁎ a Dipartimento di Scienze Farmaceutiche, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy b Dipartimento di Scienze Farmaceutiche, Università di Salerno, Via Ponte Don Melillo, 84084 Fisciano (SA), Italy c Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology,18 Hoang Quoc Viet, Nghiado, Caugiay, Hanoi, Viet Nam article info abstract Article history: Received 22 January 2009 Accepted in revised form 30 April 2009 Available online 11 May 2009 A new iridoid glycoside, adenosmoside (1), together with five known phenylpropanoids, crenatoside, verbascoside, cistanoside F, campneoside I, and campneoside II and two known flavonoids, apigenin 7-O-β-D-glucuronopyranoside and apigenin 7-O-β-D-glucopyranoside, were isolated from the aerial parts of Adenosma caeruleum R. Br. Their structures were elucidated by spectral evidence. © 2009 Elsevier B.V. All rights reserved. Keywords: Adenosma caeruleum Scrophulariaceae Iridoid Phenylpropanoids 1. Introduction The genus Adenosma (Scrophulariaceae family) counts of about 15 species widespread in South and South East Asia, China, and Pacific Islands. All its species are herbs, erect or creeping, blackened when dry, and frequently aromatic [1]. Adenosma caeruleum R. Br., known in Vietnam as “nhan tran” is a perennial herb, 30–100 cm tall, with erect stems, widely distributed in the mountains of North Vietnam where its dried aerial parts are used in folk medicine for the treatment of jaundice, bile, and liver diseases as well as illness of women after child birth [2]. Previous phytochemical studies on the chloroform extract of A. caeruleum aerial parts, reported the isolation of a monoterpene peroxide [3], betulinic acid, arbutin, aucubin, β-sitosterol, stigmasterol, and campesterol [4], but a literature survey indicates that its polar extracts have not yet been investigated. In continuation of our studies on natural products from Vietnamese medicinal plants [5,6], we isolated and characterized a new iridoid glycoside, together with five known phenylpropanoids and two known flavonoids from A. caeruleum aerial parts methanol extract. 2. Experimental 2.1. Generals Optical rotations: Perkin-Elmer 241 polarimeter equipped with a sodium lamp (589 nm) and a 1 dm microcell. HPLC separations: Shimadzu LC-8A series pumping system (Shi- madzu, Kyoto, Japan) equipped with a Waters R401 refractive index detector (Waters Corporation, Milford, MA, USA) and Shimadzu injector using a μ-Bondapack C 18 semipreparative column (300×7.8 mm; 5 μm); HRMS: Q-TOF Premier instrument (Waters, Milford, MA), equipped with a nanoe- lectrospray ion source; ESIMS analyses: LCQ Advantage ThermoFinnigan spectrometer (ThermoFinnigan, San Jose, CA, USA), equipped with a Xcalibur software. NMR spectra: Bruker DRX-600 spectrometer using the UXNMR software package. TLC: precoated Kieselgel 60 F 254 plates (Merck, Darmstadt, Germany); detection Ce(SO 4 ) 2 /H 2 SO 4 and NTS/ PEG. Column chromatographies: Sephadex LH-20 (Pharma- cia, Sweden). HPCPC: Everseiko CPC240 chromatograph (Everseiko Corporation, Tokyo, Japan). 2.2. Plant material A. caeruleum R. Br. (Scrophulariaceae), aerial parts were collected in Tamdao National Park, Vinh Phuc province, Fitoterapia 80 (2009) 358–360 ⁎ Corresponding author. Tel.: +39 050 2219688; fax: +39 050 221660. E-mail address: braca@farm.unipi.it (A. Braca). 0367-326X/$ – see front matter © 2009 Elsevier B.V. All rights reserved. doi:10.1016/j.fitote.2009.05.003 Contents lists available at ScienceDirect Fitoterapia journal homepage: www.elsevier.com/locate/fitote