Chapter 9

Chemistry, Therapeutic Attributes, and Biological Activities of Dillenia indica Linn

Ashok K. Singh and Sudipta Saha 

A. K. Singh · S. Saha (*)

Department of Pharmaceutical Sciences, Babasaheb Bhimrao Ambedkar University, Lucknow, Uttar Pradesh, India

e-mail: sudiptapharm@gmail.com

© Springer Nature Singapore Pte Ltd. 2019

R. C. Sobti et al. (eds.), Environmental Biotechnology: For Sustainable Future,

https://doi.org/10.1007/978-981-10-7284-0_9

Dillenia indica Linn. (Dilleniaceae) is generally known as elephant apple and locally known as outenga. The vernacular names are chalta, chulta, bhavya, karambel, ouu, and ramphal. This evergreen deciduous tree is markedly disseminated in the seasonal tropics of many Asian countries, in India from Himalaya to south India. The different parts of this plant have been prevalently investigated for the plethora of biological activities including anticancer, antidiabetic, antihyperlipidemic, antileukemic, antioxidant, antimutagenic, antimicrobial, antinociceptive, antidiarrheal, and hairweaving activities. Differently prepared extracts of this plant have been reported mainly to contain a wide range of flavonoids, triterpenoids (lupene-type), phytosteroids, phenolics, alcohols, and ketones and an anthraquinone. Several phytochemical investigations revealed substantial presence of various types of active constituents including β-sitosterol, stigmasterol, betulin, betulinic acid, kaempferol, myricetin, quercetin, dillenetin and rhamnetin. Among these the major chemical constituents are betulin and betulinic acid (lupene-type triterpenoids) that show a wide spectrum of pharmacological activities like anti-HIV, anticancer, antimalarial, anti-inflammatory, etc. The present chapter thus approaches to highlight on phytochemistry, traditional and therapeutic uses, and biological activities of Dillenia indica.

Introduction

A vast amount of knowledge and practices on herbal medicinal systems have been transmitted through the ages. For centuries, medicinal plants were the only resources available for the treatment of several diseases which afflicted humanity (Ozdemir and Alpınar 2015). Numerous of these plants are uncommon, endemic, and found only in forest region. There is neither biological data nor satisfactory information that prompted their rarity in the natural surroundings (Kerrigan et  al. 2011). Correspondingly, there are many plant species which have been utilized by tribal and folk communities of different forest regions of India; however, their medicinal and also pharmacological esteem is yet obscure as these plants are hardly available. There are many plant species which have been utilized by tribal groups of India; however, their restorative and also pharmacological knowledge is yet obscure as these plants are not easily accessible and studied. Among these, there are few plants belonging to family Dilleniaceae which have not gained much popularity but have interesting medicinal values. The genus Dillenia has 60 species; however, only a few of them are reported to have important phytochemicals and thereby enrich their medicinal values. These species are D. indica, D. pentagyna, D. suffruticosa, D. andamanica, D. serrata, D. sumatrana, D. aurea, D. bracteata, D. excelsa, D. ovata, D. papuana, D. parviflora, D. philippinensis, D. pulchella, D. reticulata, D. scabrella, D. eximia, and D. triquetra. Only two plants D. indica Linn. and D. pentagyna Roxb. are available in India. D. indica has been extensively studied and a more commonly employed medicinal plant in different parts of India (Dickison 1979). Several research works have been conducted on the isolation and quantification of the different phytochemicals from various parts of D. indica; however, very few phytochemical investigations have been performed from D. pentagyna.

D. indica grows in moist and evergreen forests of India (The Wealth of India 1952). This plant is known for its lemon-flavored fruits that are used to prepare jam and jellies and as flavoring agent for curries (Sharma et al. 2001). This plant has been exploited by tribal and folk communities of various regions where the fruits of D. indica are eaten raw, but people are not much familiar with its medicinal values (Pradhan and Badola 2008; Dubey et al. 2009; Sharma and Pegu 2011). The leaf, stem bark, fruit, and flower of D. indica contain a wide range of flavonoids, triterpenoids (lupene-type), phytosteroids, phenolics, alcohols, and ketones and an anthraquinone. The substantial presence of various types of active constituents including β-sitosterol, stigmasterol, betulin, betulinic acid, kaempferol, myricetin, quercetin, dillenetin and rhamnetin enriches the diversity of therapeutically important phytochemicals in D. indica. The major chemical constituents among these are betulin and betulinic acid (lupene-type triterpenoids) that show vast and wide range of medicinal values.

The present review is an attempt to compile the detailed phytochemistry, traditional and therapeutic uses, as well as biological activities of this plant. This review may be helpful to explore further excellent phytochemistry and medicinal potentials of D. indica for the preparation of various types of formulations in future. 

Chemistry

The significant classes of chemical constituents extracted from D. indica are flavonoids and triterpenoids (lupene-type). Other isolated compounds including phytosteroids, diterpene, ionone, phenolics, anthraquinone, alcohols, and ketones also enhance the diversity of phytochemistry in D. indica. As per our extensive search, a total of 34 compounds isolated from D. indica are included in this review which may lead to further research and noble challenge to discover new chemical constituents from this plant. These compounds are listed in Table 9.1, and their chemical structures are displayed in Fig. 9.1.

Stem bark of D. indica contains triterpenoids like lupeol, betunaldehyde, and betulinic acid; flavonoids like kaempferol, dillenetin, rhamnetin, dihydroisorhamnetin, myricetin, naringenin, and quercetin; and 10% tannin (Shah 1978; Khanum et al. 2007; Khare 2007). The ethanol extract of stem bark is enriched with two flavonoids, kaempferol and quercetin, as well as a triterpenoid (Srivastava and Pande 1981). Parvinet al. (2009) acquired methanolic extract of stem after partitioning with n-hexane and isolated four compounds, viz., lupeol, betulinic acid, betunaldehyde, and stigmasterol, using column chromatographic separation.

Leaves of D. indica contain betulinic acid, betulin, lupeol, and β-sitosterol (Dan and Dan 1980). The petroleum ether extract of leaves contains betulin, β-sitosterol, cycloartenone, and n-hentriacontanol, whereas chloroform extract has betulinic acid (Mukherjee and Badruddoza 1981). Methanolic extract of leaves after fractionation with n-hexane and chloroform also has compounds like betulinic acid, β-sitosterol, dillenetin, and stigmasterol (Muhit et al. 2010). Phytochemicals have also been investigated from acid hydrolyzed extracts of dried leaves which demonstrated the presence of kaempferol, whereas fresh leaves were found to contain dihydrokaempferide and naringenin-7-diglucoside which get further oxidized to ten corresponding flavonols (Bate-Smith and Harborne 1971). Kumar et al. (2010) isolated and quantified betulinic acid using validated HPLC method from various fractions such as methanol, ethyl acetate, n-butanol, and water. The highest concentration among them was found in ethyl acetate fraction.

Fruit of D. indica contains about 34% of total phenolics in methanolic extract (Abdille et al. 2005), isorhamnetin (Pavanasasivam and Sultanbawa 1975a), lupeol, betulin, β-sitosterol (Sundararamaiah et al. 1976), and polysaccharide like arabinogalactan. Uppalapati and Rao (1980) reported the presence of steroids, saponins, fixed oil, free amino acids, glycosides, tannins, and sugars in the seeds of D. indica. These scientific reports collectively revealed that betulin, betulinic acid, and β-sitosterol are present in almost all parts of D. indica.