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Brief Introduction to the Annonaceae Family

CHAPTER 1. OVERVIEW


1. 1 Brief introduction to the Annonaceae family


The Annonaceae is a family of flowering plants including trees, shrubs or vines. This is the largest family of the Magnoliales with 130 genera and 2,300 species, distributed mainly in tropical and subtropical regions [8],[11].

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Most of the major life forms are found in the genus Polyathia, except for the herbaceous plants and the epiphytic or parasitic life forms. In the upright species, they are usually found in the form of shrubs or small trees. Meanwhile, many other species of the genus Polyathia and a series of other genera are found in the form of large trees [8].

The general morphology of the custard apple trees has the following characteristics [8]: The leaves of all custard apple species have no stipules, grow alternately, are simple, and have entire margins with pinnate veins. The flowers of custard apple species are usually bisexual. Flowers grow alone or in different inflorescences, in leaf axils or outside leaf axils, at the top of branches or on old leafless stems. This characteristic is often used to distinguish the genera in the custard apple family. Stamens in the custard apple family have two main types: “Uvarioid type” with a rather thick and long meridian that exceeds the anther to form a meridian crest, “ Miliusoid type” with a thin and narrow meridian, making the anther protrude compared to the meridian. Most custard apple species have a pistil consisting of separate carpels. Each carpel is divided into an ovary, style, and stigma.


1.2 Introduction to plants of the genus Goniothalamus


1.2.1 Overview of the genus Goniothalamus


1.2.1.1 Morphological characteristics of genus Goniothalamus


Goniothalamus species are shrubs or small trees, with stellate hairs on young parts. Flowers are bisexual, usually borne in the axils of green or fallen leaves.

Flowers rarely grow on old stems or both at the top and axil; at the base of the flower stalk there are often a number of small bracts. Sepals (3), petals (6) are all valved; the 3 outer petals are usually flat; the inner petals are very small and thicker than the outer petals, tapering at the base into narrow claws, and the apex is fused to form a cap, covering the stamens and pistil. Stamens are numerous, uvarioid; the median crest is sometimes very pointed at the tip or often truncated, the anthers are outward, often with a transverse septum. Carpels are numerous, the style is often clear, with the stigma intact or slightly bilobed. Ovules 1-2 or 3-10. Fruit segments are upright or have short pedicels [8].

The genus Goniothalamus has 160 species, distributed from Asia to New Guinea, concentrated in Southeast Asia (Thailand, Indochina, Malaysia, Indonesia, Philippines). In Vietnam, this genus has 19 species [7],[8].

1.2.1.2 Some Goniothalamus species in Vietnam


According to author Nguyen Tien Ban, the genus Goniothalamus in Vietnam has 19 species [8]:

Goniothalamus albiflorus Ban (White-flowered Goniothalamus): Up to now, this species has only been found in Central Vietnam: Thua Thien-Hue, Kon Tum.

Goniothalamus chinensis Merr. & Chun. (Chinese Goniothalamus chinensis): This tree is found in Lao Cai (Sapa), Ha Giang, Quang Ninh and also in China (Guangxi, Guangdong, Hainan).

Goniothalamus chartaceus PT Li (Paper-leg or paper-leg): This species is currently only found in Northern Vietnam: Quang Ninh, Lang Son.

Goniothalamus donnaiensis Fin. & Gagnep. (Velvet Goniothalamus, also known as Dong Nai Goniothalamus): This species has only been found in Central and Southern Vietnam: Khanh Hoa, Kon Tum, Dak Lak, Dak Nong, Lam Dong, Ninh Thuan, Dong Nai.

Goniothalamus elegans Ast. (Goniothalamus elegans): This species is newly found in Central Vietnam: Quang Binh.

Goniothalamus expansus Craib (Goniothalamus expansus): This species is found in Gia Lai and also found in Thailand.

Goniothalamus gabriacianus (Baill.) Ast. (Goniothalamus gabriacianus): This species is found in Quang Tri, Da Nang, Quang Nam, Khanh Hoa, Ninh Thuan, Kon Tum, Gia Lai,

Dak Lak, Tay Ninh, Binh Duong, Ba Ria-Vung Tau, Kien Giang, also in China, Laos, Cambodia.

Goniothalamus gracilipes Ban (Long-stemmed Goniothalamus): This species is found in Central Vietnam (Dak Lak), recently also found in Thai Nguyen.

Goniothalamus macrocalyx Ban (White Areca, also known as Big-eared Areca, Calf's Ear, Ground Pigeon ) : This species is found in Bac Can, Hanoi, Hoa Binh, Thanh Hoa, and recently found in Ha Giang.

Goniothalamus multiovulatus Ast. (Goniothalamus multiovulatus): Up to now, this species has only been found in Central Vietnam: Thua Thien-Hue, Da Nang.

Goniothalamus ninhianus Ban (Goniothalamus ninhianus): Found in Lam Dong.

Goniothalamus takhtajanii Ban (Tam Dao): This species is only found in Northern Vietnam: Vinh Phuc (Tam Dao).

Goniothalamus tamirensis Pierre ex Fin. & Gagnep. (Goniothalamus tamirensis, also known as Goniothalamus Tamir): This species is found in Nghe An, Quang Tri, Thua Thien-Hue, Da Nang, Khanh Hoa, Dak Lak, Dak Nong and also in Laos and Cambodia.

Goniothalamus tenuifolius King (Goniothalamus tenuifolius King): This species is found in Kon Tum, and is also found in Malaysia.

Goniothalamus touranensis Ast. (Goniothalamus touranensis): Up to now, this species has only been found in the Central region of Vietnam: Da Nang, Quang Nam, Khanh Hoa, Dak Lak, Lam Dong.

Goniothalamus undulatus Ridl. (Wavy Goniothalamus): Found in Dak Lak, also found in Myanmar and Thailand.

Goniothalamus vietnamensis Ban (Black Fatty): This species is newly found in Northern Vietnam: Cao Bang, Quang Ninh, Phu Tho, Hanoi (Ba Vi, Minh Quang).

Goniothalamus wightii Hook.f. & Thoms. (Indian Goniothalamus): This species is found in Da Nang, Khanh Hoa, Ninh Thuan, Gia Lai, Dong Nai, and also in India, Laos, and Cambodia.

Goniothalamus yunnanensis WT Wang (Goniothalamus yunnanensis): This species is found in Lao Cai, Son La, Lang Son, Hoa Binh and also in China (Yunnan).

According to author Vo Van Chi, a species of the genus Goniothalamus in Vietnam is used as a medicine in folk medicine such as the leaves of the paper tree ( G. chartaceus PT Li) are used to boil water to wash wounds; the stem of the velvet tree ( G. donnaiensis Fin. & Gagnep.) is used as a medicine to treat injuries from falls and broken bones; the roots of the Saigon tree ( G. gabriacianus (Baill.) Ast.) are used as an antidote, to treat rashes and measles; the roots of the black Bo Beo tree ( G. vietnamensis Ban) are used to boil water to drink as a tonic, to stimulate digestion [9].


1.2.2 Botanical characteristics of the large-flowered Aglaonema plant

G. macrocalyx Ban is a small tree, 10-15 m high, young branches, leaf stalks and flower stalks have rusty hairs. Leaves are tough, usually smooth on the upper surface, oblong or oblong-ovate, both surfaces (except the main vein on the lower surface) are smooth; leaf tip is short, leaf base is blunt; lateral veins are faint but slightly raised on both surfaces. Flowers grow in the axils of fallen leaves (sometimes on old branches); flower stalks are thick, at the base bearing 4-6 uneven bracts with hairs on both surfaces ( Figure 1.1. ).

(1) [8] (2)

Figure 1.1. Flowering branch (1) and photo of leaf specimen and fruiting branch (2) of the large-flowered Giac De Cay tree

The large-flowered species of the Giac de calyx has outer petals that are pale yellow when fresh, thick, lanceolate, with a midrib, both sides covered with rust-colored hairs; inner petals are ovoid, slightly pointed at the tip, fused together at the top to form a cap, the outer surface is hairy. There are many stamens, with clear filaments.

Anthers with transverse septa; slightly convex disc-shaped, hairy crest. Carpels numerous, ovary with long hairs; style short; pistil funnel-shaped, as long as ovary, slightly bi-lipped at apex. Ovules 2. Receptacle nearly flat. Fruit segment with black-brown hairs, oblong or curved cylindrical, with a pointed beak at apex, thin shell. Seeds brown, smooth and slightly glossy [8].


1.2.3 Botanical characteristics of the long-stemmed Aglaonema plant

G. gracilipes Ban is a small shrub, 3-4 m high, branches and petioles have brown hairs when very young, later smooth. Leaves are thin, oval or oblong. Both sides (except the main vein on the lower side) are hairless, leaf tip has a slightly short tip, base is wedge-shaped or obtuse, secondary veins are very faint on both sides. Flowers grow alone in leaf axils; flower stalks are thin, at the base bearing 3-5 bracts. Bracts are sometimes large leaves measuring 12-20 x 6-10 mm. Sepals are separate from the base, broadly ovate, slightly obtuse at the tip. Both sides are almost smooth, durable along the fruit and close to the base of the fruit ( Figure 1.2. ).


(1) [8] (2)

Figure 1.2. Flowering and fruiting branches (1) and photo of leaf and fruiting branches (2) specimens of the long-stemmed Giac De tree

The long-pedunculated species of Giac de has thick outer petals, ovoid with a pointed tip, both sides are hairy (the outer surface is thicker) and are yellow-brown in color, attached by the edge and have a distinct 3-sided tip; the inner petals are diamond-shaped, attached at the tip to form a pointed cap, the outer surface is hairy and yellow-brown. The stamens are numerous and shaped like nails, with short filaments; the integument

The pollen has a transverse septum, the median crest is convex, has short hairs, and is much wider than the anther. The carpels are not numerous, slightly longer than the stamens, the ovary is completely smooth, the style is small and short, the stigma is cylindrical, at the top is entire and slightly flared. The ovule is single. The fruit segment is ovoid, has a pointed tip, is smooth, and is red when ripe, on a very long stalk of 3-4 cm, and the fruit shell is thin. The seeds are smooth, gray-yellow [8].

1.3 Studies on the chemistry and biological activity of the genus Goniothalamus


To date, only about 30 species out of 160 species of the genus Goniothalamus have been studied phytochemically. These studies show that styryl-lactone, acetogenin and alkaloids are the three main classes of substances found in Goniothalamus species , in addition to some other groups of substances such as flavonoids, terpenoids, ...[7].

1.3.1 Styryl-lactone from genus Goniothalamus

Styryl-lactones isolated from the genus Goniothalamus usually have a basic C13 skeleton consisting of a styryl chain attached to a lactone ring, which is divided into 6 characteristic basic structural groups including: styryl-pyrone ( I ), furano-pyrone ( II ), furano-furone ( III ), pyrano-pyrone ( IV ), butenolide ( V ) and heptolide ( VI ) ( Figure 1.3. ). Many styryl-lactones exhibit rich biological activities such as cytotoxicity, antitumor, insecticide, antimicrobial, antimalarial, antituberculosis and antioxidant activities; in which the cytotoxic activity has been studied meticulously and the mechanism of action of styryl-lactone has been proposed [7],[10].





Figure 1.3. Basic framework of styryl-lactone

1.3.1.1 Styryl-pyrone from genus Goniothalamus


In 1972, the group of authors K. Jewers and colleagues from the British Institute of Tropical Compounds isolated ( R )-goniothalamine ( 1 ) from the bark of Goniothalamus andersonii . This was the first styryl-lactone compound isolated from the genus Goniothalamus (Annonaceae) [12].

This compound has also been isolated from several species of the genus Goniothalamus , such as

G. andersonii, G. fulvus, G. giganteus, G.macrophyllus, G. malayanus, G. scortechinii, G. sesquipedalis, G. tamirensis, G. tapis and G. uvaroides , including the Vietnamese species G. tamirensis [13].

In 1998, initial biological activity testing results showed that ( R )-goniothalamine

( 1 ) has in vitro activity against many cancer cell lines such as leukemia cell line P388, tumor WEHI1640 and human gastric cancer HGC-27 with ED 50 values ​​of 0.75; 1.70; 0.70 g/mL, respectively [14]. Further testing showed that ( R )- Goniothalamine ( 1 ) is active against cervical cancer cell lines Hela, breast cancer MCF7, and ovarian cancer Caov-3. In particular, ( R )-goniothalamine is not toxic to healthy cells. In vivo anti-cancer activity test results showed that this compound has anti-breast cancer activity in Sparague-Dawley experimental rats [15].

In 2003, the Malaysian group of authors SH Inayat-Hussain and colleagues studied the cytotoxic activity of ( R )-goniothalamine ( 1 ) on leukemia cells HL-60. From the model of the programmed death program of leukemia cells HL-60, it was shown that styryl-lactone ( R )-goniothalamine ( 1 ) from the genus Goniothalamus activates the caspases enzyme system through the loss of mitochondrial membranes leading to the release of mitochondrial cytochrome c , causing chromosomes to shrink and unable to divide, and causing cell growth to stop [16].

In 2011, the group of authors M. Al-Qubaisi evaluated in detail the cytotoxic activity of ( R )-goniothalamine against human cancer cell lines including

HepG2 liver cancer cells, Chang normal liver cells. The results showed that ( R )-goniothalamine ( 1 ) has the ability to selectively reduce the growth of HepG2 cells after 72 hours with an IC 50 value of 4.63 M, while the IC 50 value for the Chang cell line is 35.01 M. The study showed that the cytotoxic activity of ( R )-goniothalamine ( 1 ) is related to the inhibition of DNA synthesis [17], [18].

In addition to cytotoxic activity, ( R )-goniothalamine ( 1 ) also exhibits antifungal activity. In 2008, a group of Brazilian researchers tested and showed that ( R )-goniothalamine ( 1 ) exhibited different levels of activity against many fungal strains, of which the strongest activity was against two fungal strains Paracoccidioides braziliensis and Paracoccidioides braziliensis with MIC values ​​of 9.0; 6.8 g/mL, respectively [19]. Recently, in 2013, a group of Malaysian scientists

RPT Kim et al. evaluated the antioxidant activity of ( R )-goniothalamine ( 1 ) and found that it had antioxidant activity (IC 50 = 2.04 M), but was less active than the control (ascorbic acid IC 50 = 0.075 M) [20].

Several derivatives of ( R )-goniothalamine ( 1 ) have been isolated from species

different species of Goniothalamus , thus this compound is considered a precursor in the biosynthesis of other styryl-lactone compounds ( 2-5 ). Styryl-pyrones are commonly found in different forms with different degrees of oxidation of the phenyl ring bond and degrees of saturation of the pyrone ring such as 7,8-olefin styryl-pyrone (( R )-goniothalamine ( 1 )); 7,8-epoxy styryl-pyrone (goniothalamine oxide ( 2 )); 7,8- dihydroxy styryl-pyrone (goniotriol ( 3 ), goniodiol ( 4 )); saturated styryl-pyrone (garvensintriol ( 5 )). Goniothalamine oxide ( 2 ) was isolated from G. macrophyllus of Malaysia in 1987. The results of biological activity testing showed that this compound has the ability to cause abortion in mice [21]. From the G. giganteus species , Indian scientists successively isolated goniotriol ( 3 ) (1989), goniodiol ( 4 ) (1991). The results of cytotoxic activity tests showed that goniotriol ( 3 ), goniodiol ( 4 ) were both active against lung cancer cell lines A-549, breast cancer MCF-7, colon cancer HT-29; in which compound 4 had stronger activity than ( 3 ) in all 3 cell lines and the activity against the A-549 cell line was the strongest (ED 50 = 0.12 g/mL) [14],[22],[23].

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