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Nor-Hopanes from Zanha Africana Root Bark with Toxicity to Bruchid Beetles

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Nor-Hopanes from Zanha Africana Root Bark with Toxicity to Bruchid Beetles See discussions, stats, and author profiles for this publication at: https://www.researchgate.net/publication/291337770 Nor-hopanes from Zanha africana root bark with toxicity to bruchid beetles Article in Phytochemistry · January 2016 Impact Factor: 2.55 · DOI: 10.1016/j.phytochem.2016.01.008 READS 91 6 authors, including: Philip C Stevenson Paul W C Green University of Greenwich Royal Botanic Gardens, Kew 123 PUBLICATIONS 1,914 CITATIONS 33 PUBLICATIONS 203 CITATIONS SEE PROFILE SEE PROFILE Iain William Farrell Steven R Belmain Royal Botanic Gardens, Kew University of Greenwich 10 PUBLICATIONS 68 CITATIONS 105 PUBLICATIONS 979 CITATIONS SEE PROFILE SEE PROFILE All in-text references underlined in blue are linked to publications on ResearchGate, Available from: Philip C Stevenson letting you access and read them immediately. Retrieved on: 26 May 2016 Phytochemistry 123 (2016) 25–32 Contents lists available at ScienceDirect Phytochemistry journal homepage: www.elsevier.com/locate/phytochem Nor-hopanes from Zanha africana root bark with toxicity to bruchid beetles ⇑ Philip C. Stevenson a,b, , Paul W.C. Green b, Nigel C. Veitch b,1, Iain W. Farrell b, Paul Kusolwa c, Steven R. Belmain a a Natural Resources Institute, University of Greenwich, Central Avenue, Chatham Maritime, Kent ME4 4TB, UK b Royal Botanic Gardens, Kew, Richmond, Surrey TW9 3AB, UK c Faculty of Agriculture, Sokoine University of Agriculture, Box 3005, Morogoro, Tanzania article info abstract Article history: Zanha africana (Radlk.) Exell (Sapindaceae) root bark is used by farmers throughout sub-Saharan Africa to Received 28 July 2015 protect stored grain from bruchid beetles, such as Callosobruchus maculatus. Chloroform, methanol and Received in revised form 21 December 2015 water extracts of Z. africana root bark inhibited oviposition and caused significantly higher mortality of Accepted 12 January 2016 C. maculatus at a rate of application equivalent to that applied by farmers compared to control insects. Available online 20 January 2016 The chloroform extract contained nor-hopanes rarely found in plants of which seven were isolated, one of which was previously known. Two of the most abundant nor-hopanes 3b,6b-dihydroxy-7b-[(4- Keywords: hydroxybenzoyl)oxy]-21aH-24-norhopa-4(23),22(29)-diene and 3b,6b-dihydroxy-7b-[(4-hydroxyben- Zanha africana zoyl)oxy]-24-norhopa-4(23),17(21)-diene were toxic to and reduced oviposition of C. maculatus in a dose Sapindaceae Cowpea dependent manner. Z. africana root bark is rich in insecticidal compounds that account for its effective use Fabaceae by smallholder farmers as an alternative to conventional insecticides. Bruchid beetles Crown Copyright Ó 2016 Published by Elsevier Ltd. All rights reserved. Callosobruchus maculatus Pesticidal plants Botanicals Stored product pests Post-harvest pest management Vigna unguiculata 1. Introduction including zanhasaponins A, B and C isolated from the root bark which reportedly account for anti-inflammatory properties Zanha africana (Radlk.) Exell is a medium sized tree belonging to (Cuellar et al., 1997a,b). More recently, the structurally related the Sapindaceae (Flora Zambesiaca) and occurs in the African compounds zanhasaponins D–H have also been reported from root savannah and distributed from Kenya southwards through Tanza- bark of Z. golunguensis, the only other species in the genus growing nia, Malawi, Mozambique, Zambia, Zimbabwe, southern Angola in Africa (Lavaud et al., 2015). and Namibia (Beentje, 1994; Swanepoel, 2013). Zanha species have Smallholder farmers in Tanzania use the root bark of Z. africana cultural importance across the range. For example, Zanha to protect stored grain from stored product pests (Mkoga et al., golunguensis is a source of medicine (Bruschi et al., 2011) with 2004) by pounding the stripped bark to a powder and admixing activity reported in bark against trypanosomiasis (Nibret et al., with their grain. The potential livelihood impact of wild, locally 2010), bacterial pathogens (Kambizi and Afolayan, 2001) and fungi available plants in pest control is compelling if they can be sustain- (Fabry et al., 1996), and also has anti-inflammatory activity (Recio ably sourced, particularly for poorly-resourced small-scale farmers et al., 1995). Z. africana is rich in oleanane type saponins based (Grzywacz et al., 2014; Isman, 2006). The aim of this study was to on the zanhagenic triterpene skeleton (Kapundu et al., 1992) analyse the chemistry of Z. africana root bark and identify compo- nents that might be responsible for any biological activity against insects. Understanding the chemical basis of activity in pesticidal plants provides tools necessary to explain temporal and spatial ⇑ Corresponding author at: Natural Resources Institute, University of Greenwich, Central Avenue, Chatham Maritime, Kent ME4 4TB, UK. variation in efficacy (Belmain et al., 2012), inform about the occur- E-mail address: [email protected] (P.C. Stevenson). rence of chemotypes (Stevenson et al., 2012), and enable the devel- 1 Deceased. opment of optimized field application (Stevenson et al., 2009). http://dx.doi.org/10.1016/j.phytochem.2016.01.008 0031-9422/Crown Copyright Ó 2016 Published by Elsevier Ltd. All rights reserved. 26 P.C. Stevenson et al. / Phytochemistry 123 (2016) 25–32 In this paper, the identity of seven nor-hopanes from the root b-oriented. Compound 3 was therefore 11a-acetoxy-3b,6b-dihy- bark of Z. africana was determined of which six are reported for droxy-7b-[(4-hydroxybenzoyl)oxy]-21aH-24-norhopa-4(23),22(29)- the first time. These components explain, at least in part, the bio- diene. efficacy of the root bark of Z. africana in protecting stored cowpeas The main difference between the 1H NMR spectra of 4 and 2 was from bruchid damage in smallholder farm stores. that the former contained resonances corresponding to two 4- hydroxybenzoyl groups rather than one. The first set of resonances was assigned to the 4-hydroxybenzoyl group at 7-OH. The second 2. Results and discussion was placed at 11-OH on the basis of the large downfield shift (Dd + 1.56 ppm) experienced by H-11 (dH 5.76) and the long-range cor- 2.1. Identification of nor-hopanes in Z. africana relation between this proton and the remaining 4-hydroxybenzoyl carbonyl at dC 167.3. As expected, H-11 correlated with H-9 and The chloroform extract of Z. africana root bark was shown to be 12-CH2 in the COSY spectrum. In common with 3, J9,11 for 4 was toxic to a bruchid beetle, Callosobruchus maculatus (L.), in bioassays also 11.3 Hz, confirming a diaxial relationship between H-9 and described in detail below (Sections 2.2 and 3.1). This extract was H-11 with the latter b-oriented. Thus compound 4 was 3b,6b-dihy- analysed using LC-UV-MS/MS and indicated the presence of droxy-7b,11a-di[(4-hydroxybenzoyl)oxy]-21aH-24-norhopa-4(23), numerous non-polar peaks with similar UV spectra. Seven com- 22(29)-diene. pounds, 1–7 (Fig. 1), were isolated using semi-preparative HPLC A full set of 1H and 13C NMR resonance assignments was and characterized using spectroscopic techniques. obtained for 5 using COSY, HSQC and HMBC data. Compound 5 1 13 Full assignment of the H and C NMR spectra of 1 in CDCl3 was was isomeric with 1 and could be readily identified as a 24- obtained using COSY, HSQC and HMBC data (Tables 1 and 2). The norhopadiene derivative. The difference between the two com- 13C NMR assignments of 1 showed a good match with those for pounds resided in the structure of the E-ring. In the case of 5, the 3b,6b-dihydroxy-7b-[(4-hydroxybenzoyl)oxy]-21aH-24-norhopa- E-ring was a fused cyclopentene with an isopropyl group at C-21, 4(23),22(29)-diene (Chávez et al., 1997). Good agreement was also whereas 1 featured an isopropylidene group attached to C-21 of found between the 1H NMR assignments and a partial dataset a fused cyclopentane moiety. The multiplet structure and J-values given by the latter authors, with the exception of the assignments for H-3, H-6, and H-7 (MeOH-d4) were similar for 5 and 1 indicat- of H-9 and H-13 which required revision (Table 1). A second NMR ing that the configurations of these atoms were conserved between dataset for 1 was acquired in MeOH-d4 because of the improved the two compounds. Thus 5 was 3b,6b-dihydroxy-7b-[(4-hydroxy- resolution of the multiplet structure of several key resonances benzoyl)oxy]-24-norhopa-4(23),17(21)-diene. including H-3 and H-6. A series of 1D site selective ROE experi- The molecular formula of compound 6 differed from that of 5 by ments indicated that 1 had the same relative configuration as the the inclusion of one additional oxygen atom, and it was also iso- published structure (Fig. 1). In particular, the a-configuration of meric with 2. Analysis of its 1H and 13C NMR spectra indicated that H-21 was confirmed by an ROE correlation with 28-Me. Other 6 was the 11a-hydroxyl derivative of 5. Thus in the HMBC spec- key ROE correlations were between 28-Me and 27-Me, 27-Me trum acquired in CDCl3, H-11 (dH 4.25) correlated with C-8 (dC and H-7 (confirming the b-configuration of the 7-(4-hydroxyben- 48.5), C-9 (dC 54.5), C-10 (dC 39.8) and C-12 (dC 36.6). Similarly in zoyl)oxy group), H-7 and H-5, H-6 and H-5 (confirming the the COSY spectrum, H-11 correlated with H-9 and 12ACH2. The b-configuration of the 6-OH group), H-5 and H-3 (confirming relative configuration of 6 was examined in a series of 1D site the b-configuration of the 3-OH group) and 25-Me and 26-Me.
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