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Mostafa, E.M.; Musa, A.; Mohammed, H.A.; Alzarea, A.I.; Abdelgawad, M.A.; Al-Sanea, M.M.; Ismail, A.; Zafar, A.; Elmowafy, M.; Selim, S.; et al. Medicinally Viable Plants of the Genus Tylophora. Encyclopedia. Available online: https://encyclopedia.pub/entry/41922 (accessed on 28 April 2024).
Mostafa EM, Musa A, Mohammed HA, Alzarea AI, Abdelgawad MA, Al-Sanea MM, et al. Medicinally Viable Plants of the Genus Tylophora. Encyclopedia. Available at: https://encyclopedia.pub/entry/41922. Accessed April 28, 2024.
Mostafa, Ehab M., Arafa Musa, Hamdoon A. Mohammed, Abdulaziz Ibrahim Alzarea, Mohamed A. Abdelgawad, Mohammad M. Al-Sanea, Ahmed Ismail, Ameeduzzafar Zafar, Mohammed Elmowafy, Samy Selim, et al. "Medicinally Viable Plants of the Genus Tylophora" Encyclopedia, https://encyclopedia.pub/entry/41922 (accessed April 28, 2024).
Mostafa, E.M., Musa, A., Mohammed, H.A., Alzarea, A.I., Abdelgawad, M.A., Al-Sanea, M.M., Ismail, A., Zafar, A., Elmowafy, M., Selim, S., & Khan, R.A. (2023, March 07). Medicinally Viable Plants of the Genus Tylophora. In Encyclopedia. https://encyclopedia.pub/entry/41922
Mostafa, Ehab M., et al. "Medicinally Viable Plants of the Genus Tylophora." Encyclopedia. Web. 07 March, 2023.
Medicinally Viable Plants of the Genus Tylophora
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This entry is adapted from the peer-reviewed paper 10.3390/plants12051143

Plants of the genus Tylophora have commonly been used in traditional medicine in various communities, especially in the tropical and subtropical regions of climatic zones. Of the nearly 300 species reported in the Tylophora genus, eight are primarily used in various forms to treat a variety of bodily disorders based on the symptoms. Certain plants from the genus have found use as anti-inflammatory, anti-tumor, anti-allergic, anti-microbial, hypoglycemic, hypolipidemic, anti-oxidant, smooth muscle relaxant, immunomodulatory, and anti-plasmodium agents, as well as free-radical scavengers. Pharmacologically, a few plant species from the genus have exhibited broad-spectrum anti-microbial and anti-cancer activity, which has been proven through experimental evaluations. Some of the plants in the genus have also helped in alcohol-induced anxiety amelioration and myocardial damage repair. The plants belonging to the genus have also shown diuretic, anti-asthmatic, and hepato-protective activities. Tylophora plants have afforded diverse structural bases for secondary metabolites, mainly belonging to phenanthroindolizidine alkaloids, which have been found to treat several diseases with promising pharmacological activity levels. 

genus Tylophora phenanthroindolizidine alkaloids chemotaxonomy secondary metabolites anticancer antiviral antimicrobial anti-inflammatory

1. Introduction

Tylophora (family Asclepiadaceae) is widely distributed, primarily in Australia, Asia, and Africa [1][2]. The name Tylophora comes from the Greek words “tylos”, which means knot, and “phore”, which means carrier or bearer. Tylophora indica is the most common species in this genus and is used in most traditional medicines. It is an annual and perennial, small, slender, climbing, and much-branched young herb [3]. It has been reported that plants from this genus are used in traditional medicine for treating bronchial asthma, rheumatism, allergies, and dermatitis [4][5][6][7]. In addition, the plant has anti-tumor, anti-oxidant, immunomodulatory, and hypotensive activities. It is also used for treating numerous respiratory difficulties, such as asthma, bronchitis, hay fever, the common cold, and coughs [8][9][10]. Moreover, the leaves and roots of this plant have been used to treat jaundice and symptomatic liver disorders [4][11][12][13]. Tylophora genus plants also possess a wide range of bioactivities, including immune modulatory effects, free-radical scavenging (anti-oxidant), hepato-protective, anti-convulsant [4][14][15][16], anti-anxiety, anti-bacterial, anti-asthmatic, anti-inflammatory, anti-cancer, anti-amoebic [4][6][10][16][17][18][19], anti-psoriasis, seborrhic, and anaphylactic effects, and they are used for the treatment of leucopenia and the Schultz-Dale reaction. The roots and leaves of the plant, Tylophora indica, possess medicinal and therapeutic properties as an expectorant, laxative, diaphoretic, and purgative [20][21][22]. Several secondary metabolites from Tylophora species have been isolated, including alkaloids such as tylophorine, tylophorinidine, septicine, and tylophorine, as well as non-alkaloidal compounds such as quercetin, tannin(s), tetratriacontanol, α- and β-amyrins, octaosanyl octacosane [10][23][24][25][26][27]. Tylophorinine and tylophorine are the main alkaloids found in this genus, and have been shown to be responsible for the strong anti-inflammatory effects exhibited by plants in the genus [28][29]. The phenanthroindolizidine class of alkaloids, isolated and identified as the tylophorine class, is exemplified and represented by tylophorinidine, tylophorine, tyloindicines A–J, tylocrebrine, tylophorinine, and O-methyl tylophorinidine, as active components. These alkaloids are known to possess potent anti-cancer activity through participation different mechanisms of action [30][31][32]. 

2. Taxonomy of Genus Tylophora

2.1. Geographic Distribution

Tylophora plants are widely distributed in the southern hemisphere and some smaller regions in the north, where warm and wet climates are found. These perennial climbers are native to forests, grasslands, and hills in the southern and eastern Indian subcontinent, as well as other parts of Asia, including Sri Lanka, Malaysia, Thailand, Australia, and the Pacific Islands. Although the genus did not originate there, the plants are also found on the African continent. Over 300 species of Tylophora have been identified and recorded to date. These plants belong to the division Angiosperm, class Mangoliatae, order Gentianales, family Asclepidaceae, and genus Tylophora [24][33][34][35].

2.2. Morphological Description

The plants in the genus are mostly erect herbs or woody climbers, but some of the species are succulents. The leaves are simple, sub-sessile, exstipulate, fleshy, and covered with a coating of wax. Flowers are cymose, or racemose inflorescence, pedicellate, bracteolate, bisexual, and actinomorphic, but rarely zygomorphic. Five polysepalous sepals and five gamopetalous petals have been described. The androecium is composed of five stamens, and the anthers are syngenesious, giving rise to a five-sided blunt cone, which is usually attached on the inside to the stigma head. In the gynoecium, which is bicarpellary, the ovaries remain free, but styles unite to form a commonly swollen stigma-head. The placentation is marginal, with numerous ovules. Fruits are produced by pairs of follicles, but sometimes there is only one follicle because of the suppression of the other. The seeds are ovate-oblong, flat, and capped by hairs or fruits, and these hairs enable the seeds to be dispersed by the wind. The embryo is large [36]. Tylophora indica (Burm f.) Merill., also known as Anantmool in the vernacular language, is a perennial plant found in southern and eastern India in plains, forests, and hilly areas. The climbing shrub, or twining plant can reach up to 1.5 m in height, and is widespread in the provinces of Uttar Pradesh, Bengal, Assam, Orissa, and the Himalayan regions. The leaves are obovate-oblong to elliptic-oblong, and measure between 3–10 cm in length and 1.5–7 cm in width. The roots are long and fleshy, with a light brown, fissured corky bark. The flowers are small, about 1–1.5 cm across, and arranged in 2–3-flowered clusters in axillary umbellate cymes. The calyx is divided nearly to the base, with densely hairy lanceolate segments. The corolla is greenish-yellow, or greenish-purple, with oblong, acute lobes. The fruit is an ovoid-lanceolate follicle with 0.6–0.8 × 0.3–0.4 cm long seeds that taper at the apex, forming a fine mucro before becoming striate and glabrous [37].

3. Traditional Phytomedicinal Uses of Genus Tylophora Plants

Plants belonging to the genus Tylophora have been extensively used in traditional phytomedicine. The aerial parts are taken orally for the treatment of constipation, flatulence, hemorrhoids, whooping cough, asthma, congestion, inflamed skin, jaundice, gout, tender joints, and arthritis. Their use also induces sweating and vomiting. Tylophora plants have also been applied topically for allergies, inflamed skin, wounds, and skin ulcers, and used as a smooth muscle relaxant, and anti-lupus agent [38]. The plants have been recommended by an informed herbalist for cancer and rheumatoid arthritis. Tylophora indica has been extensively used as a remedy for bronchial asthma, and to relieve mild pain, and dermatitis [39]. T. indica has been used in Pakistan to treat skin and systemic allergies, as well as bronchitis. It has also found use as an emetic, laxative, cathartic, purgative, stimulant, and diaphoretic in areas of Pakistan [14]. T. indica leaves have been used to treat tuberculosis and as an antidote to snake bites [40][41]. The plant has also found use as a muscle relaxant, an anthelmintic, for the treatment of hydrophobia, and as a food preservative [4][42]. Table 1 summarizes the ethnomedicinal uses of the Tylophora species found in different geographic locations and their local uses.
Table 1. Ethno-medicinal uses of genus Tylophora species.
Tylophora Species Ethno-Medicinal Applications Location Reference
T. asthinatica Treatment of bronchial asthma and allergy India, Pakistan, and Indonesia [43][44]
T. villosa Treatment of liver disorders Indonesia [45]
T. hirsuta Treatment of diabetes, treatment of eye diseases in veterinary medicine India and Pakistan [46][47][48]
T. indica Treatment of asthma, dermatitis, constipation (flower part), dysentery, cough, snake poison, and rheumatic conditions. The plant is also used as an expectorant, diaphoretic, and emetic agent. Bangladesh, India (Orissa state) [49][50][51][52][53]
T. fasciculata Treatment of fever and body pain Orissa [51]
T. atrofolliculata Treatment of rheumatoid arthritis China [54][55][56][57]
T. ovata Treatment of rheumatism, asthma, and traumatic injury China, and Taiwan [32]
T. floribunda Treatments of irregular menses Chania and Hong Kong [58]
T. barbata Treatments of inflammation Australia [58]
T. perrottetiana Treatments of wounds Sri Lanka [59]

4. Chemotaxonomy of the Genus Tylophora, Phenanthroindolizidine, and Secophenanthroindolizidine Alkaloids

Chemotaxonomy, also known as chemosystematics, differentiates plant species based on chemical constituents with respect to their phenotypic category and specifications of biogenetically derived constituents, which are frequently of a secondary metabolic nature. This information has led to insights into the taxonomy of the plants, and has, in turn, has helped in metabolomics (metabolic profiling) understanding. In conjunction with morphological and cytological data, the array of chemical constituents of certain and defined structural features, found primarily in plant species within the genus, has intertwined the taxonomic classification and helped in plant identification and taxonomical classification. Genomics, transcriptomics, and proteomics relate the phenotype of a taxon to its genome, and this further strengthens the phenotypical characteristics to chemosystematics, thereby providing a foundation for the taxonomy and genomics. Chemogenomic systematics ignores the presence of small molecules in plants, which are frequently linked to environmental responses as well as biodiversity. From the perspective of chemical constituents, the presence of specific categories of compounds, and distinguishing secondary metabolic products, provide taxonomic factors, assist in testing their congruence with existing classifications to identify the chemotype, and at times predict the formation of inter-related secondary metabolites useful to human health and drug discovery.

As structured entities, phenanthroindolizidine alkaloids are composed of a dibenzo-[f,h]pyrrolo [1,2-b]isoquinoline ring as the core structural motif in various alkaloids from Tylophora species and have thus been classified as chemotaxonomic or chemosystematic markers for the genus. However, interconnected structures have been observed in several species of the plant family Moraceae [60][61].

Phenanthroindolizidine alkaloids presence has been recorded among almost all 300 species of the genus Tylophora, which is part of the Asclepiadaceae family. Phenanthroindolizidine alkaloids are abundant in several species from four other genera besides Tylophora, namely Pergularza, Cyanchum, Antitoxzcum, and the genus Vincetoxzcum [60]. 

5. Biogenesis of Genus Tylophora Alkaloids

Phenanthroindolizidine alkaloids are a small group of naturally occurring compounds isolated from the genera Tylophora, Pergularia, and Cynanchum of the family Asclepiadaceae. A detailed biogenetic pathway is outlined in Figure 1. The biogenesis of these pentacyclic phenanthroindolizidine alkaloids, e.g., tylophorine, and other structurally inter-related compounds containing four to five ring units, is derived from different amino acid (AA)-based precursors, such as tyrosine, phenylalanine, and ornithine [62][63]. The later AA contains both α- and δ-amino groups, and the nitrogen of the previous group is involved with the carbon chain in the formation of the alkaloidal structure barring its carboxyl group. In this pathway, ornithine supplies a C4N structural block, basically a pyrrolidine ring, for advancing biogenesis of the alkaloid. The reactivity of ornithine is nearly matched by L-lysine, which manipulates a C5N unit containing its amino group towards the formation of the molecule [64]. Mechanistically, the pyrrolidine ring system is originally formed as a Δ1-pyrrolinium cation, and the putrescine, along with oxidative deamination by the action of a diamine oxidase, produces the required aldehyde. The Δ1-pyrrolinium cation is further transformed to imine, and in the presence of water, upon the involvement of cinnamic acid, it forms the emerging skeleton of the developing alkaloid. Ring B of an alkaloidal structure is formed by tyrosine, while ring A is formed by phenylalanine. Phenylalanine is consolidated through cinnamic, caffeic, and p-coumaric acids to produce the alkaloids’ structures. Owing to further modifications in the biogenetic pathways, a convenient hydroxylation pattern develops with the participation of p-coumaric, or caffeic acid. The important steps of oxidation and decarboxylation, and the condensation of 3-hydroxyphenylpyruvic acid followed by transformation of the carbinol amine, result in the formation of a diaryl-7-dehydroindolizidine intermediate, which is a seco structure. Finally, phenol oxidative coupling results in the formation of tylophorine and tylocrebrine structures via position 2 and 6 couplings, respectively. The involvement of methionine completes the methylation step(s) of the OH group(s) of the final alkaloid structure [62][63][65].
/media/item_content/202303/6406ff6c8e139plants-12-01143-g001.png
Figure 1. Biogenetic outline of the genus Tylophora alkaloid.

6. Biotechnical Production of Tylophorine

6.1. Production of Tylophorine and Agrobacterium-Mediated Transformation

Agrobacterium rhizogenes, a Gram-negative bacterium that is mainly located in the soil, causes infection in plants [66]. It transfers T-DNA, a 25-base pair oligonucleotide replication through a transformation procedure from roots, presenting plasmid (Ri) to the influenced plant’s genome [67]. During this transformation, hairy roots are produced at the spot of infection. This technique is considered one of the most effective pathways for manufacturing required secondary metabolic compounds, without causing any damage to the original plant, and with continuous production of the desired secondary metabolites within a short period of time. The transgenic root production technique has been standardized in T. indica after infection of its aerial parts and intact shoots by Agrobacterium rhizogenes (LBA 9402 and A4 strains). The roots and calli were prompted at different locations [68][69]. The response was a result of several underlying factors, such as the type of strains (Gram positive and Gram negative), and explants used, as well as the site of infection. The A4 strain was the only one that recorded a response inducing the transformation process. The maximum rate of transformation was reported to be around 60% with the intact shoots confirmed by PCR analysis. The production of tylophorine (its structure is shown in Figure 1) from different root clones was variable, and the maximum root biomass and tylophorine were obtained in about one month of suspension culture. The roots were dried, powdered, and subjected to defatting with a non-polar solvent for 24 h, followed by shaking with chloroform for a similar period of time. The extracts were pooled together, dried by evaporation, and the residue was re-extracted with chloroform three times, and separated by a separating funnel.

6.2. Extraction from Suspension Cultures Callus, and Dried Leaves

A quantitative analysis using HPTLC (High-Performance Thin Layer Liquid Chromatography) technique was performed to quantify and extract tylophorine (its structure is shown in Figure 1) from Tylophora spp. dried ground leaves, callus, and suspension cultures [70]. The technique depended on extraction with methanol acidified with acetic acid, followed by EtOAc (ethyl acetate) extraction. By using the Rf values of test samples to compare with the Rf value of the reference standard sample, the material’s presence was quantified. Variability of tylophorine concentration in the three samples, obtained from leaves extract, leaf-based callus, and suspension extract was quantified. Leaf extract attained the maximum level of tylophorine in the sample, followed by the leaf callus, and the suspension extract, with 80, 24.46, and 28.30 μg/mL, respectively.

7. Biological Activities

7.1. Biological Activities of Genus Tylophora

Tylophora species are pharmacologically active. Several species of the genus Tylophora have been associated with diverse biological actions. The medicinal properties of some of the plants belonging to the genus Tylophora (Figure 2).
/media/item_content/202303/6406ff3e2298dplants-12-01143-g002.png
Figure 2. Important biological activities of the genus Tylophora (The plant picture is for T. indica).

7.2. Structure-Activity Relationship (SAR) of Tylophorine

Tylophorine (its structure is shown in Figure 1), the naturally abundant phenanthroindolizidine alkaloid, studied for its potential to inhibit cancer cell growth, has shed light on its structure-activity relationships (SAR) Previous studies on the phenanthroindolizidine alkaloids showed that a rigid phenanthrene ring is necessary for strong cytotoxicity. The absence of an indolizidine ring, or the presence of an OMe (ethereal methyl) group at position 2, results in a loss of cytotoxicity [71]. It was also believed to exert its anti-cancer effects through modulation of the vascular endothelial growth factor receptor (VEGFR2). VEGFR2 plays a crucial role in regulating cell growth, cell survival, cell proliferation, and the cells’ overactivation, which is a hallmark of many types of cancer. Tylophorine was thought to disrupt signaling pathways that cause cancer cell growth and survival by modulating VEGFR2 receptors, resulting in decreased cancer cell proliferation and increased cell death. Studies have shown that tylophorine binds to certain VEGFR2 receptors and modulates their activity, leading to the inhibition of cancer cell growth. The interaction between tylophorine and VEGFR2 was found to have a stable conformation based on in silico analysis.

8. Conclusions

Plants from the genus Tylophora are widely distributed in the tropical and subtropical regions of warm and wet climatic southern-hemisphere countries. The plants are medicinally viable species that have been documented in various anthropological societies for their traditional uses against various physiological and hormonal disorders. Activities such as anti-cancer, anti-tumor, broad-spectrum anti-microbial, anti-fungal, and anti-virus activities have been reported and pharmacologically established for plants of the genus. Other pharmacological activity confirmation though symptomatic treatment of physiological disorders is imperative. Molecular modeling-based activity predictions of the nearly forty-four phenanthroindolizidine alkaloids, which are abundant in eight plant species, are tasks for the future. There is still a pressing need to pursue extensive phytochemical screening and bioassay-guided activity confirmations using the extracts, and subsequent and designated fractions, as well as determining the biological activity of isolated pure constituents of known, novel, and new structures, especially of an alkaloidal nature, towards finding new bioactive chemical entities and molecular templates for oncological and other aspects of drug design and discovery.

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Subjects: Chemistry, Medicinal; Chemistry, Organic; Biology
Contributors MDPI registered users' name will be linked to their SciProfiles pages. To register with us, please refer to https://encyclopedia.pub/register :
Ehab M. Mostafa
,
Arafa Musa
,
Hamdoon A. Mohammed
,
Abdulaziz Ibrahim Alzarea
,
Mohamed A. Abdelgawad
,
Mohammad M. Al-Sanea
,
Ahmed Ismail
,
Ameeduzzafar Zafar
,
Mohammed Elmowafy
,
Samy Selim
,
Riaz A. Khan
View Times: 428
Revisions: 3 times (View History)
Update Date: 09 Mar 2023
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