Contents lists available at ScienceDirect Biochemical Systematics and Ecology journal homepage: www.elsevier.com/locate/biochemsyseco Flavans and other chemical constituents of Crinum biflorum (Amaryllidaceae) Boris Y. Kianfé a , Rémy B. Teponno a,b,∗ , Jonas Kühlborn c , Roland T. Tchuenguem d , Beaudelaire K. Ponou a , Soleiman E. Helaly b , Jean P. Dzoyem d , Till Opatz c , Léon A. Tapondjou a,∗∗ a Department of Chemistry, Faculty of Science, University of Dschang, P.O. Box 67, Dschang, Cameroon b Department of Microbial Drugs, Helmholtz Centre for Infection Research Braunschweig, Inhoffenstrasse 7, 38124, Braunschweig, Germany c Johannes Gutenberg University Mainz, Institute of Organic Chemistry, Duesbergweg 10-14, D–55128, Mainz, Germany d Department of Biochemistry, Faculty of Science, University of Dschang, Box 67, Dschang, Cameroon ARTICLE INFO Keywords: Crinum biflorum rottb. Amaryllidaceae Flavan-3-ol Chemotaxonomic signifcance Antimicrobial activity ABSTRACT The ethyl acetate extract from the whole plant of Crinum biflorum Rottb. Showed a moderate activity against Enterococcus faecalis. Its phytochemical investigation led to the isolation of a new favan-3-ol derivative namely (2R,3R)-3-hydroxy-7-methoxy-3′,4′-methylenedioxyfavan, together with (2S)-7-hydroxy-3′,4′-methylenedioxy- favan, (2R,3R)-7-methoxy-favan-3-ol, (2S)-7-hydroxy-3′,4′-dimethoxyfavan, 3′,7-dihydroxy-4′-methoxyfavan, 4′,7-dimethoxy-3′-hydroxyfavan, farrerol, β-sitosterol, β-sitosterol-3-O-β-D-glucopyranoside, oleanolic acid, kaempferol, pancratistatin, lupeol, aurantiamide acetate, Narciprimine and 2,3-dihydroxypropyl palmitate. Their structures were elucidated mainly by extensive spectroscopic analysis and comparison with published data. The absolute confguration of the new metabolite was determined by electronic circular dichroism (ECD) analysis and comparison of optical rotation. Some of the isolated compounds were tested for their antimicrobial activity but no inhibition was observed. 1. Subject and source The Amaryllidaceae family represented by the monocotyledon plants contains more than 60 genera including the genus Crinum (Takos and Rook, 2013). C. biflorum is a bulbous herb with distichous leaves, and pinkish fowers, one or two borne on a scape about 30 cm high. It is found in seasonally fooded places in savanna from Senegal to Nigeria and extending to Sudan (Burkill, 1985a). Plants of this genus are used in the traditional medicine to relieve some diseases such as: malaria (C. zeylanicum L.) (Beckstrom-Sternberg et al., 1994), convulsion, asthma, malaria and sexually transmitted diseases (C. glaucum A. Chev.) (Burkill, 1985b; Duri et al., 1994; Ishola et al., 2013). The whole plant of C. biflorum was collected in Dschang, West Region of Cameroon, in April 2017 with the location 5°26′38″N, 10°03′11″E and identifed at the National Herbarium of Cameroon (NHC), Yaoundé where a voucher specimen (N°7736/SFR Cam) was deposited. The taxonym was established as described by Aubreville and Leroy (1963). 2. Previous work The previous chemical studies on Crinum species have shown the presence of alkaloids and favonoids (El-hafz and Ramada, 1990; Elgorashi et al., 2001; Ghosal et al., 1981; Koagne et al., 2018). Fur- thermore the pharmacological studies of plants of this genus showed the variable activities: anti-infammatory, analgesic, antibacterial, an- timalarial (Ghosal et al., 1985a; Okpo et al., 2001; Viladomat et al., 1995). In our continuous search for bioactive secondary metabolites from Cameroonian medicinal plants (Nzowa et al., 2013; Fouedjou et al., 2014; Teponno et al., 2016), we report in this paper the isolation and characterization of a new favan-3-ol and ffteen other metabolites from the whole plant of C. biflorum. 3. Present study The dried powder from the whole plant of C. biflorum (2 kg) was extracted three times with ethanol (11 l) at room temperature for https://doi.org/10.1016/j.bse.2019.103953 Received 30 June 2019; Received in revised form 18 September 2019; Accepted 19 September 2019 ∗ Corresponding author. Department of Chemistry, Faculty of Science, University of Dschang, P.O. Box 67, Dschang, Cameroon. ∗∗ Corresponding author. E-mail addresses: remyteponno@gmail.com (R.B. Teponno), tapondjou2001@yahoo.fr (L.A. Tapondjou). Biochemical Systematics and Ecology 87 (2019) 103953 0305-1978/ © 2019 Published by Elsevier Ltd. T