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Phytopharmacological Review of Iridoids Isolated from Plumeria genus.

Byline: Naseem Akhter, Rashad Mahmood, Shehla Parveen, Tasneem Khatoon, Farzana Rafiq and Shgufta Sattar

Summary: Plumeria (Apocynaceae), a genus of scenery plants commonly known as frangipani, comprises around 8 species which are mainly distributed in tropical countries. Plumeria species are well known to be have various pharmacological properties such as diarrhea, gonorrhea, syphilis, venereal sores, leprosy, fever, cough, tracheitis, infective hepatitis, purgative, bronchitis, dysentery, blood disorders, tumor and respiratory ect. These pharmacological properties are due to the presence of certain secondary metabolites such as iridoids, alkaloids, flavonoids, terpenoids, tannins, steroids and their glycosides. Literature shows that Plumeria genus is a good source of iridoids. This review reports the iridoids and their biological activities isolated from various species of the genus Plumeria till to date. It is also found that iridoids are also present in plants of various other families, and the plants that posses iridoids have significant biological activities.

Key words: Plumeria; Apocynaceae; Iridoids; Biological properties; Phytochemicals.

Introduction

The genus Plumeria belongs to the Apocynaceae family, which is a flowering plant family of 300 genera and 2000 species as trees, shrubs and herbs, mainly distributed in tropic and subtropic regions of both hemisphere [1], and commonly known as dogbane family [2]. Plumeria plants are grown for decorative purpose because of their attractiveness and fragrant flowers and they also have medicinal values. The essential oils from the flowers are used for perfumery, and aromatherapy purposes [3]. Plumeria species have traditionally been used to treat heart stroke, purgative, fever, dysentery, diarrhea [4], arthritis, rheumatism, pruritic skin lesion, tooth ache [5], asthma [6] constipation, promote menstruation and soothe irritation [7]. Plumeria species has been used as an abortifacient [8]. This genus species have also used to control diabetes mellitus and for the treatment of ulcers, leprosy, inflammations and rubifecient [9].

Different parts of various species have been useful to cure various ailments including malaria, leprosy, rheumatism, abdominal tumors, skin diseases such as herpes, scabies and ulcers [10-11], cardiotonic, diuretic and hypotensive [12]. The species of Pulmeria genus also exhibited various pharmacological activities such as antiinflammatory [13], antioxidant [14], antipyretic [15-16], antibacterial [17], antifungal [18-19] and antiviral [20-21]. This genus is well known for its iridoids constituent and a number of iridoids have been obtained from Plumeria species. So, Plumeria species are rich with various class of iridoids, and ridoids have versatile pharmaceutical activities including analgesic, anticoagulant, antihepatotoxic, antimutagenic, antiprotozoal, antispasmodic, choleretic, hypoglycemic and immunomodulator activities [22-24].

Generally, the iridoids having glycoside decrease the risk of breast cancer [25]. The versatility in pharmacological activities of Pulmeria species might be due to the iridoids presence. The purpose of this minireview is the compilation of all iridoids isolated from Plumeria genus and their pharmacological activities.

Iridoids are basically a cyclopentano [c] pyran monoterpenoids. The first iridoid, iridomyrmecin, is a defensive in nature, was isolated from Iridomyrmex genus. Iridomyrmecin is C(8) epimer of isoiridomyrmecin, has planner lactone group, six member ring and cycle pentanoid ring endo to six memebred ring [26]. Iridoids are structural link between terpenes and alkaloids and biosynthesized from isoprene and intermediates in the biosynthesis of alkaloids [27]. [beta] cis-fused bicyle at position H-5 and H-9 cyclopentanopyran ring is basic skeletal feature of this class; carbocylic or secosekelton (Fig. 1a) which may consist of ten, nine, or rarely eight carbon atoms in which C11 is more frequently missing than C10 [24, 28-32] [Fig. 1]. Oxidative cleavage at the 7,8-bond of the cyclopentane moiety affords the so-called secoiridoids, while cylcopentane ring is known basic skeletal ring for iridoids [33-35].

In plants they are derived from 9-hydroxy nerol by phosphorylation followed by cyclization, oxidation and glycosidation in several steps [36]. The last step involves O-glycosidation or O-methylation [18]. In vivo studies and incorporation of radioactive compounds experiments revealed that geranyl pyrophosphate is the precursor of iridoids [37-39]. Cyclization of an acyclic monoterpene to the iridane skeleton may involve a double Michael-type addition of geranyl pyrophosphate to yield iridodial [27-28]. Possibly, iridodial (Fig. 1b) or 8-epi-iridodial (Fig. 1c) is the predecessor of iridoids in many plant families [32]. In most of the iridoids obtained from Plumeria species, a simple or branched alkyl chain of four carbons is introduced at C-10 by malonyl CoA or acetyl CoA as ketide group which is then reduced to unsaturated or saturated alkyl chain or modified to lactonic moiety [22].

Further, in most of Plumeria iridoids C-11 is removed completely or oxidized to carboxylic acid functionality and/or then methylated to ester moieties by S-adenosyl methionine.

All known iridoids seem to be derived from this iridodial cation that can be stabilized, either by borrowing a proton from one neighboring carbon atom (C7, C9 or C10) or by the entrance of one hydride following five routes [28]. The cyclization reaction to form iridoid pyrane ring may results from one of the two routes: route 1 - loss of a proton from carbon 4 leads to the formation of a double bond C3-C4; consequently the 3-O-carbonyl atom will attach C1 (2a); route 2 - hydride attack on C1 will lead to 1-O-carbonyl atom attack on the C3, yielding the lactone ring ( 2b) [28] [Fig. 2].

Iridoids may be envisaged as a biogenetic alternative to the typical monoterpenes and there is evidence for an inverse relationship between the production of monoterpenes and iridoids in the Lamiaceae family [29].

Iridoids isolated from the genus Plumeria

Phytochemical studies on the roots of P. acuminata afforded the fulvoplummierin (1), plumericin (2) along with isoplumericin (3), [beta]-dihydroplumericin (4) and [beta]-dihydroplumericinic acid (5) [40]. Compounds 2 and 3 have also been reported from the bark of P. articulate [41]. Plumericin (2) has also been reported from the roots of P. multifloraas as antimicrobial agent [42].

The phytochemical investigations on P. acutifolia yielded a number of iridoids as fulvoplummierin (1) [43], 8-isoplumieride (6), 13-plumenoside (7), deoxylplumieride (8), 1-[alpha]-plumieride (9), 1-[alpha]-protoplumericin A (10), 13-O-caffeoylplumieride (11) [44], plumieride (12) [45], protoplumericin A (13) [44] and 15-demethylplumieride (14) [46]. Compounds protoplumericin A (13) and plumieride acid (15-demethylplumieride) (14) have also been isolated from P. alba in its phytochemical studies [47].

As a result of phytochemical investigations on P. obtusa, the compounds 6"-O-acetylplumieride p-Z-coumarate (15), 6"-O-acetylplumieride p-E-coumarate (16), plumieride-p-Z-coumarate (17), plumieride-p-E-coumarate (18), [48] obtusadoid A (19), plumieridin A (20), obtusadoids B (21), plumieridine (22), 1-[alpha]-plumieride (9) and 15-demethylplumieride (14) [49] have been reported.

Phytochemical studies on P. rubra afforded the plumericin (2), isoplumericin (3), [beta]-dihydroplumericin (4) [50], [beta]-dihydroplumericinic acid (5) [51], fulvoplumierin (1), plumericin (2), plumieride (12), 15-demethylplumieride (14), plumieride p-E-coumarate (18), allamcin (23), allamandin (24), [alpha]-allamacidin (25), [beta]-allamacidin (26) [9], protoplumericin A (13) [52], plumieridin A (20), plumieridin B (27) [53], an iridoid alkaloid plumericidine (28) [54], plumeridoid C (29) and epiplumeridoid C (30) [18] [Fig. 3].

Pharmacological activities of iridoids isolated from Plumeria

Fulvoplumierin (1) was isolated from P. acutifolia and has antibacterial potential against various strains of Mycobacterium tuberculosis 607 [55]. In rats, 1 reduced the production of spermatids by 87.3 % and caused suppression of fertility [56]. The extract of P. bicolor was found to be in vitro antiparasitic against Leishmania donovani. Plumericin (2) and isoplumericin (3), constituents of P. bicolor, were active against promastigote and amastigote forms of Leishmania donovani and cytotoxic against J774G8 murine macrophage cells [57-58]. Both 2 and 3 also exhibited the anticancer [59-61], algicidal, barnicidal [59], antifungal [62], molluscicidal, cytotoxic and antibacterial activites [21]. P. alba bark contain 2% plumieride (12) which is a non-toxic and non irritant to the conjunctiva.

Plumieride (12), was also obtained from P. obtusifolia and has been reported to inhibit the gibberellins induced growth in dwarf peas, corn and rice [63]. Oral feeding of 12 to male rats caused weight reduction of testes, epididymides and seminal vesicle [64]. Protoplumericin A (13) and plumieride acid (14) from P. alba have been reported as antimicrobial agents [47]. Fulvoplumierin (1), allamcin (23) and allamandin (24) which were obtained from the bark P. rubra, showed cytotoxic effect against cell lines of murine lymphocytic leukemia (P-388) and various human cancer cell-types [9].

Conclusion

All the iridoids isolated from various species of Plumeria genus and their pharmacological potentials have been collected in this review for the first time. Pulmuria iridoids are of specific skeleton structure and have versatile biological activities. Pulmuria genus is naturally gifted source of biological active iridoids, whereas, need to be explored further to obtained biological active new iridoids. This review has compiled the all biological active iridoids of Pumuria genus at one place and will helpful to the researcher for the research on Pulmuria iridoids, species or their biological activities.

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Author:Akhter, Naseem; Mahmood, Rashad; Parveen, Shehla; Khatoon, Tasneem; Rafiq, Farzana; Sattar, Shgufta
Publication:Journal of the Chemical Society of Pakistan
Article Type:Technical report
Date:Jun 30, 2018
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