Flavonoids and Isoflavonoids of Millettia dura and Millettia ferruginea: Phytochemical review and chemotaxonomic values

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Highlights

  • The phytochemical information on Millettia dura, M. ferruginea and M. ferruginea subsp. darassana has been reviewed.

  • Different flavonoids and isoflavonoids, have been reported from the three taxa,and isoflavones are the main constituents.

  • Millettone and millettosine, and C-8 oxygenated isoflavones in M. dura appears to distinguish this taxon from M. ferruginea.

Abstract

The phytochemical information on Millettia dura Dunn, M. ferruginea (Hochst.) Baker and M. ferruginea subsp. darassana (Cufod.) J.B. Gillett was reviewed. All the three taxa elaborate mainly isoflavones (33 reported), occurring in the flowers, seeds/seed pods, stem bark and root bark. Out of the 33 isoflavones reported, some 19 (ca. 58%) contain prenyl at C-8 or its modification as 2,2-dimethylchromene ring at C-7/C-8, occurring in all the three taxa. Except for three isoflavones isolated from M. ferruginea subsp. darassana, all the isoflavones of these taxa are 5-deoxygenated. In these taxa, oxygenation at C-6 is a common feature, while isoflavones with C-8 oxygenation are rare, only three reported, and all of these from M. dura. There are 7 rotenoids reported from these taxa, and occur almost entirely in the seeds/seedpods of these plants. The major rotenoid with methylenedioxy group at C-2/C-3, millettone and its 12a-hydroxy derivative, millettosine, occur only in M. dura, this appears to distinguish M. dura from M. ferruginea.

Introduction

The genus Millettia Wight & Arn. belongs to the family of Leguminosae (Fabaceae) and subfamily Papilionoideae (Faboideae) ( Ren et al., 2016; Deyou et al., 2015, 2017). This subfamily is characterised by the presence of papilinoid flowers, and has five hundred genera comprising of 14,000 species worldwide (Azani et al., 2017). The genus Millettia has about 260 species widely distributed over the tropical regions of Africa, Australia, Asia (Banzouzi et al., 2008; Dagne and Bekele, 1990; Chatsumpun et al., 2010; Havyarimana et al., 2012; Kamto et al., 2012; Zhi et al., 2013) and America (Kamto et al., 2012; Ren et al., 2016). Among these, 139 Millettia species are reported to be endemic to Africa (Banzouzi et al., 2008; Deyou et al., 2015). Plants of this genus are either trees (49%), climbers/lianas (38%) (Ngandeu et al., 2008) or shrubs (13%) (Deyou et al., 2017).

There are six Millettia species in Kenya namely; M. dura, M. lasiantha, M. leucantha, M. oblata subsp. teitensis, M. tanaensis, and M. usaramensis subsp. usaramensis (Beentje, 1994). Among these, M. dura is ecologically versatile and distributed naturally in moist forests in K1 and K4 regions of Kenya, extending to Tanzania and Uganda. It is often confused with the morphologically related taxon, Millettia ferruginea (Hochst.) Baker which is endemic to Ethiopia (Gillet et al., 1971; Hu et al., 2000; Dagne et al., 1991). The only difference between the two species is that, M. dura has narrower pods, longer and more spreading indumentum of its calyx and pedicel as well as absence of a cylindrical disc, observed in M. ferruginea (Gillet et al., 1971). M. ferruginea has an infraspecific taxon M. ferruginea subsp. darassana (The Plant List, 2013). The former is distributed in central and northern Ethiopia, while the latter is restricted to southern Ethiopia (Negash, 2010; Dagne et al., 1989). Both M. dura and M. ferruginea elaborate rotenoids with insecticidal activity (Yenesew et al., 2003a, Yenesew et al., 2003b), and isoflavones with anticancer activity (Buyinza et al., 2019; Wang et al., 2020).

The chemotaxonomic value of flavonoids for some taxa in the family Leguminosae (Fabaceae) has been reported (Lima et al., 2017; Gomes et al., 1981). On the basis of the reported taxonomic confusion between M. dura and M. ferruginea, Dagne et al. (1991) compared the flavonoids and isoflavonoids isolated from these taxa and suggested that they were chemically distinct; M. dura elaborates C-8 oxygenated isoflavones, while M. ferruginea elaborates C-5 oxygenated isoflavones. Since this chemotaxonomic suggestion, several flavonoids and isoflavonoids have been described from these Millettia species. In view of this, the phytochemical information on M. dura, M. ferruginea and M. ferruginea subsp. darassana is reviewed, and also, the chemotaxonomic values of the flavonoids and isoflavonoids from these taxa are herein revisited. This review is based on phytochemical research done using organic solvent extracts of various plant parts (about 1 kg of each plant material) of M. dura (Buyinza et al., 2019; Derese et al., 2003; Marco et al., 2017; Ollis et al., 1967; Yenesew et al., 1996, 1997), Millettia ferruginea (Deyou and Jang, 2018), and M. ferruginea subsp. darassana (Dagne et al., 1989; Dagne and Bekele, 1990; Dagne et al., 1990).

Section snippets

The flavonoids and isoflavonoids of Millettia dura and M. ferruginea

The compounds isolated from M. dura, M. ferruginea and M. ferruginea subsp. darassana are presented in Table 1. From these taxa, chalcones, a flavanone and a flavonol (Fig. 1), isoflavones (Fig. 2), rotenoids and pterocarpanoids (Fig. 3) have been reported. The presence of these compounds in other Millettia species has also been included in Table 1.

Chemotaxonomic significance of flavonoids and isoflavonoids

Whereas, the occurrence of several isoflavones and rotenoids in M. dura and M. ferruginea supports the morphological similarities of these taxa, there appears to be some differences which may be useful to distinguish these taxa. C-6 oxygenated isoflavones are common in all the three taxa; on the other hand, C-8 oxygenation (compounds 14, 28 and 30) has only been observed in M. dura. The O-prenylated isoflavone isoerythrine A 4ʹ-(3-methylbut-2-enyl) ether (24), the isoflavones

Declaration of competing interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Acknowledgements

DB is thankful to the German Academic Exchange Services (DAAD) for a PhD scholarship which was awarded through the Natural Products Research Network for Eastern and Central Africa (NAPRECA). AY is grateful to the International Science Program-Sweden (ISP, KEN 02) for financial support.

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