Contents lists available at ScienceDirect Fitoterapia journal homepage: www.elsevier.com/locate/fitote A new byciclic monoterpene glucoside and a new bifavone from the male reproduction organs of Wollemia nobilis Alessandro Venditti a, ⁎ , Claudio Frezza b , Giacomo Rossi a , Ilaria Serafni a , Alessandro Ciccòla a , Fabio Sciubba a , Sebastiano Foddai b , Lamberto Tomassini b , Armandodoriano Bianco a , Mauro Serafni b a Dipartimento di Chimica, Università di Roma “La Sapienza”, Piazzale Aldo Moro 5, 00185 Rome, Italy b Dipartimento di Biologia Ambientale, Università di Roma “La Sapienza”, Piazzale Aldo Moro 5, 00185 Rome, Italy ARTICLEINFO Keywords: Wollemia nobilis W.G. Jones K.D. Hill & J.M. Allen Male reproduction organs Phytochemical analysis Primary and secondary metabolites Chemotaxonomy ABSTRACT In this work, the ffth part of an ongoing phytochemical study on Wollemia nobilis was reported. The attention was now focused on the male reproduction organs of which the content in both primary and secondary meta- bolites was analyzed. Twenty compounds, belonging to seven diferent classes of natural compounds, were identifed fromtheethanolicextractbymeansofColumnChromatographyandNMRandMSSpectroscopy.They all represent new compounds for the studied organ whereas some of them are also new constituents of the genus or even previously undescribed phytochemicals. Their presence was able to display a general overview of these organs from the phytochemical standpoint and to provide more elements in confrmation with the current bo- tanical classifcation of the species. Moreover, they add a further experimental evidence of the tendency of this species to accumulate diferent metabolites in diferent organs. This characteristic as well as the occurrence of several compounds with added value, make this plant a possible candidate for large scale cultivation with extractive purposes to obtain useful phytochemicals for botanicals and pharmaceutical felds. Moreover, they ofer the opportunity to develop an additional method of conservation and protection for this endangered and very rare species. 1. Introduction Wollemia nobilis W. G. JONES, K. D. HILL & J. M. ALLEN is a con- iferous tree belonging to the Araucariaceae family as the only member of the genus Wollemia. It is universally considered to be a living fossil because both its adult foliage and its pollen are similar to those ob- servableinfossilsdatedbacktotheLateCretaceousperiodandfoundin New South Wales [1]. In particular, this regards the pollen of the spe- cies Dilwynites granulatus W.K. Harris (family Araucariaceae) which resulted to be the most similar to the W. nobilis one [2,3]. From the morphological standpoint, W. nobilis male reproduction organs present an oval shape and are light brown colored [4](Fig. 1). This species is extremely rare and endangered even if, at the mo- ment, the number of its exemplars is gradually increasing in Australia where it is, actually, native as well as in other countries of the world, such as Italy, where this species has been introduced especially in bo- tanical gardens. Moreover, it has been subjected to a strong conserva- tion project based on the development, the production and the commercialization of several cloned specimens of Wollemi pine (Wollemia nobilis)thatarenowavailableforalltheworldgardenersand are widely requested for horticultural purposes [5]. In literature, there are only a few works on this species, most of them focused on its ecology, physiology, phytopathogens and vegeta- tive propagation [6–11]withtheprimaryscopeofitsconservation.Yet, a small number of them have reported on the phytochemical aspects of this species and, in particular, the composition of the essential oil ob- tained from diferent plant organs [12], the morphology and chemical composition of the epicuticular leaf waxes [13,14], the bifavonoid pattern from twigs [15] and, lastly, our previous works about the phytochemical pattern of male cones [16,17], leaves [18] and half- matured female cones [19] have been provided. On the other hand, there is no work about the male reproduction organs of this species in general and this represents the main reason why this work was started, togetherwiththeideatocontinueourstudyofthislittleknownspecies. In this sense, the objectives of this work were to perform the frst phytochemical analysis on these organs to provide more elements from https://doi.org/10.1016/j.ftote.2018.12.012 Received 22 September 2018; Received in revised form 4 December 2018; Accepted 16 December 2018 ⁎ Corresponding author. E-mail addresses: alessandro.venditti@gmail.com, alessandro.venditti@uniroma1.it (A. Venditti). Fitoterapia 133 (2019) 62–69 Available online 17 December 2018 0367-326X/ © 2018 Elsevier B.V. All rights reserved. T