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Review

Phytochemicals of Alpinia zerumbet: A Review

by
Yuto Nishidono
1,2,* and
Ken Tanaka
1
1
College of Pharmaceutical Sciences, Ritsumeikan University, Kusatsu 525-8577, Shiga, Japan
2
Research Organization of Science and Technology, Ritsumeikan University, Kusatsu 525-8577, Shiga, Japan
*
Author to whom correspondence should be addressed.
Molecules 2024, 29(12), 2845; https://doi.org/10.3390/molecules29122845
Submission received: 9 May 2024 / Revised: 11 June 2024 / Accepted: 12 June 2024 / Published: 14 June 2024
(This article belongs to the Special Issue Natural Bioactive Compounds from Traditional Asian Plants)
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Abstract

:
Alpinia zerumbet (Pers.) B.L.Burtt & R.M.Sm is a perennial plant of the Zingiberaceae family widely distributed in the subtropical and tropical areas of South America, Oceania, and Asia. Multiple plant parts of A. zerumbet have been traditionally used as medicinal sources, each with different clinical uses. These variations may arise from differences among the chemical components and/or accumulations of the active compounds in each part. Therefore, this review summarizes previous studies on the phytochemicals in A. zerumbet and reveals the similarities and differences among the chemical constituents of its multiple medicinal parts, including the leaves, rhizomes, fruits, seeds, and flowers. The results contribute to the scientific validation of the traditional understanding that A. zerumbet possesses different medicinal properties in each plant part. In addition, this review provides directions for further studies on the phytochemicals of this plant.

1. Introduction

Alpinia zerumbet (Pers.) B.L.Burtt & R.M.Sm, also known as shell ginger, is a perennial species belonging to the Zingiberaceae family. The previously accepted scientific name of shell ginger, A. speciosa (J.C.Wendl.) K.Schum., is now recognized as a representative synonym along with A. nutans K.Schum. and Catimbium speciosum (J.C.Wendl.) Holttum [1]. Shell ginger originated from the East Indies [2] and is native in areas ranging from South Japan to Taiwan and from South China to the Northern Peninsula [1]. The plant has also been introduced to Brazil, where it has since naturalized [3]. Therefore, A. zerumbet is currently found in the subtropical and tropical areas of South America, Oceania and Asia [4] and is variously known as Vindicá (Amazon) [5], Colônia (Brazil) [6], Yàn Shān jiāng (China) [7], yellow ginger (Fiji) [8], Chatiun in Hindi (India) [9], Punnag-champa in Bengal (India) [10], Gettō (Japan) [11], Sannin (Okinawa, Japan) [11], Atoumo (Martinique, French West Indies) [12], Yuetao (Taiwan) [1], and Riềng đẹp (Vietnam) [13].
In the endemic regions of A. zerumbet, various parts of the plant have been used for various purposes. The leaves, rhizomes, fruits, seeds, and flowers of A. zerumbet have been traditionally used for medicinal purposes. In Brazil, a decoction of the leaves is believed to exhibit an anti-hemorrhoidal activity [14]. Infusions, decoctions, and teas made from A. zerumbet leaves have been consumed as anti-hypertensives and diuretics [15,16,17]. Especially in Marajó (Brazil), the leaves have been used as remedies for colds and influenza and are added to tea and bathwater [5]. According to traditional Chinese folklore, the rhizomes of A. zerumbet can effectively treat trauma and peptic ulcers [18]. The rhizomes are also used as a preservative or flavoring condiment in alcoholic beverages [19], and the seeds are a popular aromatic stomachic [18,20]. The Miao people in Guizhou Province (China) have used the mature fruits (pericarps, placenta, and seeds) as cardiovascular disease treatments [7,21,22]. In India, the rhizomes have been applied to sufferers of catarrhal and rheumatism affections [23]. In Okinawa (Japan), the leaves are used in the traditional muchi cuisine (rice cake wrapped in A. zerumbet leaves), which is thought to protect against the common cold [24,25,26]. The leaves are also sold as herbal teas [24,27], and their essential oils are used in cosmetics, perfumes, insect repellents, and deodorants [4,24]. The seeds are employed as an aromatic stomachic [20,28] and were sold as Amomum seeds native to Japan in the first half of the twentieth century [29]. In Martinique of the French West Indies, decoctions of A. zerumbet flowers have been used as a bronchitis treatment [12]. Taiwanese indigenous peoples such as the Paiwan, Rukai, and Puyuma use the leaves in abay cuisine (leaf-covered rice with meat) [30]. The flowers are incorporated into culinary preparations. The seeds are used as medicinal ingredients [30]. In Vietnam, fever, abdominal pain, bloating, indigestion, and diarrhea are treated with a concoction obtained from boiled leaves, rhizomes, flowers, and seeds of the plant [13].
The number of studies on A. zerumbet has increased in recent times, revealing various bioactivities and pharmacological activities of the extracts and essential oils prepared from multiple medicinal parts of the plant (Table 1). These differences possibly arise from differences among the chemical components and/or the accumulation of active compounds in the individual medicinal parts. Therefore, by comprehensively clarifying the similarities and differences among the chemical constituents of the medicinal parts of A. zerumbet, we can better understand their different pharmacological activities and assess their clinical efficacies.
Five reviews on A. zerumbet have been written in English as of May 2024 [99,100,101,102,103]. In 2014, Devi and Rao [99] reviewed the therapeutic aspects of shell ginger. The botany, uses, phytochemistry, pharmacological properties, and clinical trials of A. zerumbet were reviewed by Chan et al. [100] in 2017, and the properties of this plant were briefly reviewed by Kumar and Bind [101] in 2018. Xiao et al. [102] summarized the chemical constituents in the fruits of shell ginger and elucidated their anti-atherosclerosis mechanisms. Chan et al. [103] reviewed the pharmacological properties of kavalactones, which are characteristic compounds in shell ginger. Four of these reviews described the phytochemicals of A. zerumbet [99,100,102,103]. However, a comprehensive review comparing the phytochemicals in the multiple medicinal parts of A. zerumbet which is written in English appears to be lacking.
This review summarizes the previous studies on the phytochemicals in A. zerumbet and clarifies the similarities and differences among the chemical constituents in multiple medicinal parts (leaves, rhizomes, fruits, seeds, and flowers) of the plant. The results contribute to the scientific validation of the traditional understanding that A. zerumbet possesses different medicinal properties in each part of the plant. Moreover, it provides researchers with a summary of the previous studies and directions for further studies.

2. Phytochemicals

2.1. Isolated Compounds

In total, 28 previous studies [15,19,20,28,56,59,69,78,84,93,98,104,105,106,107,108,109,110,111,112,113,114,115,116,117,118,119,120] show that more than 100 compounds have been isolated from the leaves [15,56,69,110,111,113], rhizomes [19,28,56,78,84,104,105,106,109,114,115,116,118,119,120], fruits [93], pericarps [59,107,108], seeds [20,112,116,117], and flowers [98] of A. zerumbet (Table 2; Figure 1 and Figure 2). Studies on the isolation of secondary metabolites from the stems and placenta were not found.

2.1.1. Kavalactones

Typical kavalactones (also known as kava pyrones) are 4-methoxy-2-pyrones with styryl or phenylethyl substituents at the 6-position [121]. Kavalactones have been isolated from the leaves, rhizomes, fruits, pericarps, and flowers of A. zerumbet. Xuan and Teschke [122] suggested that 7,8-dihydro-5,6-dehydrokawain (2) was first isolated 40 years ago by Pooter et al. However, Kimura et al. [104] isolated 5,6-dehydrokawain (1) and 7,8-dihydro-5,6-dehydrokawain (2) from the rhizomes of A. zerumbet in 1966. Thereafter, 5,6-dehydrokawain (1) was isolated from the leaves [15,56,69], rhizomes [19,105,106,109], fruits [93], pericarps [59,107,108], and flowers [98] of the plant, and 7,8-dihydro-5,6-dehydrokawain (2) was isolated from its leaves [15,56,69,110], rhizomes [19,105,106], fruits [93], and pericarps [59,107,108].
The kavalactone derivatives 3 and 4 were isolated as new compounds from the leaves [111] and rhizomes [106] of A. zerumbet, respectively. Four kavalactone dimers, 5–8, were isolated from the leaves [111] and pericarps [59] of the plants. (±)-Aniba dimer A (5) and alpingsin C (7) were isolated from the fruits (pericarps, placenta, and seeds) by Xiong et al. [93]. Reports on the isolation of kavalactones 1, 2, and 5–8 from the seeds are notably absent; these kavalactones have mainly been isolated from the pericarps of the fruit.

2.1.2. Chalcones

Chalcones have been isolated from the rhizomes [105,109], pericarps [108], and seeds [112] of A. zerumbet. Pinocembrin chalcone (9) [109], cardamonin (10) [105,109], flavokawin B (11) [105], and dihydroflavokawin B (13) (a new compound) [105] have been isolated from the rhizomes.
Cardamonin (10) and uvangoletin (12) have been isolated from the pericarps [108].
From the seeds, Krishna and Chaganty [112] isolated cardamonin (10).

2.1.3. Flavonoids

The isolations of flavonoids from the leaves [15,69,113], rhizomes [105,106,109,114], fruits [93], and seeds [112] of A. zerumbet have been reported. From the leaves, Mpalantinos et al. [15] isolated the five known flavonoids 14, 15, and 23–25 in 1998, and the other researchers extracted pinocembrin (16) [113], pinostrobin (17) [69], and kaempferol (20) [69].
Itokawa et al. [105] isolated alpinetin (18) from the rhizomes in 1981. Ohtsuki et al. [109] performed a phytochemical investigation of the rhizomes and isolated pinocembrin (16), naringenin (19), and 3-methoxykaempferol (21). Other researchers have isolated quercetin (22) [106] and kaempferol-3-O-glucuronide (23) [114] from the rhizomes.
Xiao et al. reported the isolation of quercetin (22) from the fruits [93].
Alpinetin (18) has been isolated from the seeds [112].

2.1.4. Diterpenoids

Diterpenoids have been obtained from the rhizomes [28,56,84,106,114,115] and seeds [20,116,117] of A. zerumbet. Most of the isolated diterpenoids are labdane and norlabdane diterpenes. (E)-Labda-8(17),12-diene-15,16-dial (27) and (E)-15,16-bisnorlabda-8(17),11-dien-13-one (55) were isolated from the rhizomes by Itokawa et al. in 1980 [28], and compound 27 was later extracted from the rhizomes by Chompoo et al. [84], Upadhyay et al. [56], Chen et al. [106], and Taira et al. [114]. Phytochemical investigations by Xiong et al. [115] resulted in the isolation of diterpenoids 26, 29–34, 36, 37, 39–54, and 56–58 from the rhizomes. Eleven of these compounds, named zerumin D1–D4 and D8–D14, were established as new compounds.
In 1995, Xu et al. [20] investigated the chemical constituents of the seeds, isolating zerumin (37) as a new labdane diterpene. They reported the first evidence of diterpene in the seeds [20]. Further studies by the same group afforded two new diterpenoids, zerumin A (28) and zerumin B (35), along with the two known diterpenoids 38 and 55, from seeds [117]. Be Tu et al. [116] isolated (E)-labda-8(17),12-diene-15,16-dial (27) from the seeds.

2.1.5. Sesquiterpenoids and Monoterpenoids

Two studies have reported the isolation of sesquiterpenoids from A. zerumbet rhizomes [115,118]. Morita et al. [118] isolated three known sesquiterpenoids, β-eudesmol (63), humulene epoxide II (66), and nerolidol (67), in 1996. Xiong et al. [115] isolated seven sesquiterpenoids, 59–65, including two new compounds (zerumin D6 (59) and D5 (60)), in 2023.
Also in 2023, we elucidated the structures of two new monoterpene esters 68 and 69 from the pericarps of A. zerumbet [108].

2.1.6. Meroterpenoids and Steroids

Xiong et al. [115] isolated the previously undescribed zerumin D7 (70) with a meroterpenoid structure from the rhizomes of A. zerumbet in 2023.
In 2024, Xiao et al. reported the isolation of β-sitosterol (71) and cholestenone (72) from the fruits [93].

2.1.7. Diarylheptanoids and Neolignans

Diarylheptanoids 73–79 were isolated from the rhizomes of A. zerumbet by Zhang et al. [119] in 2021.
From the rhizomes of A. zerumbet, El-Shamy et al. [78] isolated the neolignan 92 in 2015, and Zhang et al. [119] isolated thirteen neolignans: 80–91 and 93. Among them, seven compounds 80–86 and 88 were established as new compounds.

2.1.8. Glucoside Esters, Phenolic Compounds, and Others

Masuda et al. [120] isolated two new glucoside esters 94 and 95 from the rhizomes of A. zerumbet.
The known phenolic compounds 96–98 and 99–101 have been isolated from the rhizomes [78,105] and fruits [93] of A. zerumbet, respectively.
(E)-2,2,3,3-Tetramethyl-8-methylene-7-(oct-6-en-1-yl)octahydro-1H-quinolizine (102) and 2,5-bis (1E,3E,5E)-6-methoxyhexa-1,3,5-trien-1-yl-2,5-dihydrofuran (103) were isolated from the seeds and rhizomes, respectively [116]. Oleamide (104) was isolated from the fruits [93].

2.2. Essential Oils

The essential oils of A. zerumbet mainly include monoterpenes, oxygenated monoterpenes, and oxygenated sesquiterpenes [123]. According to the previous 35 studies [2,4,8,14,18,31,34,36,37,38,41,47,49,51,52,53,54,70,74,87,92,96,97,124,125,126,127,128,129,130,131,132,133,134,135], the relative contents of the 33 major volatile components in the essential oils prepared from the leaves [2,4,8,14,31,34,36,37,38,41,47,49,51,52,53,54,70,124,125,126,127,128,129,130], rhizomes [8,14,36,70,74,130,131], fruits [53,87,92], seeds [18,38,96], and flowers [14,53,96,97,125,130,132,133] of A. zerumbet are shown in Table 3 and Table 4. These volatile constituents are α-thujene (930), α-pinene (939), camphene (954), sabinene (975), β-pinene (979), myrcene (990), α-phellandlene (1002), α-terpinene (1017), p-cymene (1024), limonene (1029), 1,8-cineole (1031), γ-terpinene (1059), trans-4-thujanol (1070), terpinolene (1088), linalool (1098), camphor (1146), borneol (1169), terpinen-4-ol (1177), cryptone (1185), α-terpineol (1188), cuminaldehyde (1241), (E)-methyl cinnamate (1378), β-caryophyllene (1419), α-humulene (1454), elemol (1549), (E)-nerolidol (1563), caryophyllene oxide (1583), 10-epi-γ-eudesmol (1623), γ-eudesmol (1632), β-eudesmol (1650), and α-eudesmol (1653). The numbers in parentheses are the reported Kovats Retention Index (RI) values [136].

2.2.1. Leaves

The chemical constituents of the essential oils obtained from the leaves of A. zerumbet have been frequently reported [2,4,8,14,31,34,36,37,38,41,47,49,51,52,53,54,70,124,125,126,127,128,129,130]. In 1984, Luz et al. [124] investigated the composition of the essential oils in A. zerumbet leaves collected 60 km from Manausare (Brazil) and identified p-cymene (9.4%), 1,8-cineol (14.9%), γ-terpinene (9.5%), and 4-terpineol (20.4%) [124]. Cavalcanti et al. [41], Cunha et al. [34], de Carvalho Castro et al. [31], Gomes et al. [51], and Rocha et al. [54] clarified p-cymene, 1,8-cineol, and terpinen-4-ol as the main components of the essential oils from A. zerumbet leaves collected in Brazil. Other studies have revealed the chemical compositions of the essential oils derived from A. zerumbet leaves collected from Belém City, State of Pará (Brazil) in May 1997 [2], Rio de Janeiro (Brazil) [125], Núcleo de Pesquisas de Produtos Naturais (Brazil) [126], the municipality of Baturité (Brazil) in March 2010 [37], the Botanical Garden of the Universidade Federal Rural do Rio de Janeiro (GPS: 22°31′36.23 S, 44° 04′31.62 W) (Brazil) [127], Bacabal City, State of Maranhão (GPS: 4°13′2″ S, 44°46′60″ W) (Brazil) [52], and the Medicinal Plants Garden of the Federal University of Lavras (GPS: 21°12′4″ S, 44°57′58″ W) (Brazil) in September 2018 [128].
In 2009, Murakami et al. [4,47] reported a predominance of p-cymene, 1,8-cineole, and terpinen-4-ol in leaf essential oils prepared from A. zerumbet plants collected in the farms of Nihon Gettou Co., Ltd. (Okinawa, Japan). Essential oils have also been prepared from A. zerumbet leaves collected at the Faculty of Agriculture, University of the Ryukyus (Okinawa, Japan) [70], Nihon Gettou Co., Ltd. (Okinawa, Japan) [49], and Green Plan Shinjo Co. (Okinawa, Japan) [129].
Prudent et al. [14] identified terpinen-4-ol (29.8%) and 1,8-cineole (17.0%) in the essential oils obtained from raw A. zerumbet material collected in Martinique (French West Indies). They also reported (for the first time) the presence of cis/trans-sabinene hydrate, cis/trans-thujanol, cis/trans-piperitol, cuminaldehyde, (E)-β-farnesene, nerolidol, caryophyllene oxide, humulene oxide II, and β-, γ- and 10-epi-γ-eudesmol in leaf essential oil [14]. de Pooter et al. [36] extracted and analyzed the essential oil from A. zerumbet leaves collected from Orman Gardens, Giza, Egypt, in April 1990. The main ingredients were identified as sabinene (10.1%), 1,8-cineole (14.4%), γ-terpinene (11.1%), and terpinen-4-ol (17.3%) [36]. Ali et al. [8] revealed the predominance of β-pinene (10.0%), 1,8-cineole (13.2%), and terpinen-4-ol (40.9%) in the essential oil from A. zerumbet leaves collected in Fiji.
Padalia et al. [130,137] analyzed the essential oils from the leaves of plants cultivated at the Central Institute of Medicinal and Aromatic Plants Resource Center (India). They identified 1,8-cineole (19.2%) and terpinen-4-ol (28.4%) as the main constituents [130,137]. Ho [38] and Feng et al. [53] revealed the chemical composition of the essential oils prepared from A. zerumbet plants collected in Chu-Tung (Taiwan) and Guizhou Province (China), respectively. The leaves from the plants grown in Taiwan contained camphor (31.6%) [38], whereas those grown in China contained o-cymene (14.9%) [53].
Several studies are available on the chemical composition of essential oils extracted from A. zerumbet leaves collected in Brazil and Japan (Table 3). α-Thujene and α-terpinene are found in most of the essential oils in A. zerumbet leaves collected from Brazil, whereas camphene, camphor, (E)-methyl cinnamate, and α-humulene are found in most of those from Japan.

2.2.2. Rhizomes

Seven studies have revealed the chemical components of the essential oils derived from A. zerumbet rhizomes [8,14,36,70,74,130,131]. Rhizome oils prepared from A. zerumbet plants collected in the Botanical Garden of the Council of Scientific and Industrial Research—Northeast Institute of Science & Technology in Jorhat (India) [131], Martinique [14], and Fiji [8] are enriched in terpinen-4-ol (46.9%, 47.3%, and 41.4%, respectively). The rhizome essential oils in plants collected from the Central Institute of Medicinal and Aromatic Plants at the Resource Center (Pantnagar, India) are dominated by 1,8-cineole (11.8%) and endo-fenchyl acetate (40.1%) [130], whereas those collected from A. zerumbet in Dehradun (Uttarakhand, India) [74] and Orman Gardens (Giza, Egypt) [36] are dominated by 1,8-cineole (11.1% and 15.9%, respectively) and terpinen-4-ol (15.4% and 20.2%, respectively). Elzaawely et al. [70] identified methyl cinnamate (15.0%) and 7,8-dihydro-5,6-dehydrokawain (21.4%) as the main constituents of rhizome oil in A. zerumbet plants collected from Okinawa (Japan).

2.2.3. Fruits

The chemical constituents in the essential oils of A. zerumbet fruits have been reported by the groups of Shen et al. [88,92], Feng et al. [53], and Hou et al. [87]. The group of Shen et al. [88,92] identified 58 volatile compounds in the essential oils of A. zerumbet fruits collected from China. The major components were camphene (10.1%), β-pinene (15.1%), β-phellandrene (16.4%), and 1,8-cineole (11.0%) [88,92]. Feng et al. [53] identified 1,8-cineole (8.8%) in the essential oils obtained from A. zerumbet fruits collected in Guizhou Province (China) in July 2017. Hou et al. [87] revealed that α-pinene (7.1%), β-pinene (15.1%), and δ-cadinene (5.1%) dominate the essential oils of A. zerumbet fruits collected from China.

2.2.4. Seeds

Three studies have reported volatile components in the essential oils prepared from A. zerumbet seeds [18,38,96]. Elzaawely et al. [96] prepared essential oils from the seeds of A. zerumbet farmed at the Faculty of Agriculture, University of the Ryukyus, Okinawa (Japan) and revealed a predominance of terpinen-4-ol (6.2%), α-terpineol (10.7%), δ-cadinene (6.2%), T-muurolol (10.8%), and α-cadinol (13.5%) in the seed oils. Lin et al. [18] analyzed the essential oils in the seeds of A. zerumbet plants collected from Nan-Tou County in Middle West Taiwan and identified 53 compounds dominated by sabinene (33.9%) and β-pinene (30.5%). Ho [38], who analyzed the seed oils in plants from Chu-Tung, Taiwan, identified sabinene (15.1%), (Z)-β-ocimene (7.9%), camphor (19.3%), and terpinen-4-ol (6.6%) as the main ingredients.

2.2.5. Flowers

Eight studies have revealed the composition of flower oils from A. zerumbet [14,53,96,97,125,130,132,133]. The components in the oils prepared from A. zerumbet flowers were first clarified by Prudent et al. [14] in 1993. They showed that terpinen-4-ol (23.7%) is the major constituent in flowers collected from Martinique, French West Indies. Kerdudo et al. [97] analyzed the essential oils in flowers collected from various locations on Martinique Island in different seasons. The major volatiles were sabinene (7.0–16.5%), α-terpinene (1.9–8.1%), p-cymene (2.1–8.8%), 1,8-cineole (17.4–25.2%), γ-terpinene (6.9–14.7%), and terpinen-4-ol (14.7–22.6%) [97].
The flower essential oil of A. zerumbet collected from Pantnagar (India) contained sabinene (14.2%), 1,8-cineole (10.8%), γ-terpinene (19.4%), and terpinen-4-ol (25.1%) [133]. In another study of essential oils from A. zerumbet flowers collected in India, the dominant ingredients were 1,8-cineole (24.4%) and terpinen-4-ol (26.0%) [130].
Dũng et al. [132] investigated the volatile oil in flowers collected from the Xuân Phú district of Huế City, Vietnam. They identified more than 35 constituents dominated by β-pinene (34.0%). Elzaawely et al. [96] identified 1,8-cineol (16.6%), camphor (14.1%), and methyl cinnamate (12.8%) as the main components of flower oil prepared from A. zerumbet plants growing in Okinawa (Japan). Victório et al. [125] revealed that 1,8 cineole (15.5%), γ-terpinene (13.1%), and terpinen-4-ol (42.3%) dominate the flower oil of A. zerumbet in Rio de Janeiro (Brazil). The essential oils prepared from A. zerumbet flowers collected from China are dominated by camphene (9.5%), m-cymene (11.3%), and camphor (8.4%) [53].

2.2.6. Stems: Aerial Parts and Others

Prudent et al. [14] first clarified the chemical constituents in essential oils prepared from A. zerumbet stems, revealing a predominance of terpinen-4-ol (9.6%). The essential oils in the stems of plants collected from Orman Gardens (Giza, Egypt) in April 1990 were dominated by terpinen-4-ol (16.0%) and 1,8-cineole (11.5%) [36], whereas those prepared from the stems of plants collected from China were dominated by 1,8-cineole (14.9%) [53].
Joshi et al. [133] revealed that essential oils from the aerial parts are rich in sabinene (27.8%), 1,8-cineole (17.4%), and terpinen-4-ol (14.9%). Luz et al. [134] investigated the chemical components of the essential oils in the aerial parts of A. zerumbet collected in the State of Piauí (GPS: 03º01′27.5″ S, 41º44′53.5″ W) (Brazil). Among 28 metabolites, the major compounds were 1,8-cineol (19.2%), γ-terpinene (14.9%), and terpinen-4-ol (27.7%) [134].
Santos et al. [135] prepared essential oils from the flowers and leaves of A. zerumbet collected in Aracaju City, Sergipe, Brazil (GPS: 10°55′ S, 37°03′ W). The major volatile components were p-cymene (10.7%), 1,8-cineole (17.6%), γ-terpinene (11.8%), and terpinen-4-ol (37.6%).

2.2.7. Comparison of the Compositions of the Oils from Different Parts of A. zerumbet

Nine studies have reported the comparison of the compositions of the oils from different parts of A. zerumbet [8,14,36,38,53,70,96,125,130]. Ali et al. [8] reported similar essential oils in the leaves and rhizomes of A. zerumbet, with 1,8-cineole (13.2% and 28.1%, respectively) and terpinen-4-ol (40.9% and 41.4%, respectively) content. Elzaawely et al. [70] reported that 1,8-cineol (18.9%) and camphor (11.9%) dominate the leaf oil while methyl cinnamate (15.0%) and 7,8-dihydro-5,6-dehydrokawain (21.4%) dominate the rhizome oil of A. zerumbet.
According to Victório et al. [125], the compositions of leaf and flower oils from A. zerumbet are very similar and differentiated mainly by their terpinen-4-ol concentrations (19.3% in leaf oil and 42.3% in flower oil).
Ho [38] reported that camphor (31.6%), sabinene (9.4%), and γ-terpinene (8.0%) dominate the essential oils of A. zerumbet leaves, whereas camphor (19.3%), sabinene (15.1%), and (Z)-β-ocimene (7.9%) dominate the essential oils of the seeds.
Although flower oil mainly contains 1,8-cineol (16.6%), camphor (14.1%), and methyl cinnamate (12.8%), seed oil is dominated by α-terpineol (10.7%), T-muurolol (10.8%), and α-cadinol (13.5%) [96].
de Pooter et al. [36] found that the leaf, rhizome, and stem oils from A. zerumbet are composed mainly of sabinene (10.1%, 9.8%, and 7.5%, respectively), 1,8-cineole (14.4%, 15.9% and 11.5%, respectively), γ-terpinene (11.1%, 9.3%, and 8.2%, respectively), and terpinen-4-ol (17.3%, 20.2% and 16.0%, respectively).
Padalia et al. [130] reported that leaf and flower oils from A. zerumbet are mainly represented by 1,8-cineole (19.2% and 24.4%, respectively) and terpinen-4-ol (28.4% and 26.0%, respectively), but the rhizome oil is characterized by camphene (7.8%), 1,8-cineole (11.8%), borneol (5.8%), endo-fenchyl acetate (40.1%), and bornyl acetate (6.9%). endo-Fenchyl acetate, exo-fenchyl acetate, and endo-fenchol are unique to rhizome oil [130].
Prudent et al. [14] compared the essential oils in the leaves, rhizomes, stems, and flowers of A. zerumbet collected from Martinique. Terpinen-4-ol was the major constituent in all parts, present at 29.8% in the leaves, 47.3% in the roots, 23.7% in the flowers, and 9.6% in the stems.
Feng et al. [53] showed that camphene (4.4–9.5%), 1,8-cineole (7.1–14.9%), linalool (5.9–8.3%), camphor (6.2–8.4%), and borneol (4.1–8.0%) were the common major compounds in the essential oils from the stems, leaves, flowers, and fruits. The essential oils from the stems, flowers, and fruits were additionally enriched in m-cymene (7.1%, 11.3%, and 6.6%, respectively), whereas those from leaves were enriched in o-cymene (14.9%) [53].

2.3. Quantitative Analysis

2.3.1. Kavalactones

Table 5 lists the kavalactone contents identified in multiple medicinal parts of A. zurumbet [59,96,107,138,139]. Tawata et al. [138] revealed different contents of 5,6-dehydrokawain (1) and 7,8-dihydro-5,6-dehydrokawain (2) in various plant parts. More specifically, the leaves, stems, and rhizomes contain 0.01%, 0.02%, and 0.10% of compound 1, respectively, and 0.41%, 0.08%, and 0.35% of compound 2, respectively. Elzaawely et al. [96] first estimated the content of 2 in the fresh flowers (0.03%) and seeds (0.0003%) of A. zerumbet in 2007. They also reported a 0.07% proportion of 2 in fresh leaves [139]. Rao et al. [107] showed that kavalactone concentrations are higher in the pericarps (1: 0.21%, 2: 0.54%) than in the leaves (1: 0.07%, 2: 0.39%,) and seeds (1: 0.05%, 2: 0.14%,) [107]. In 2020, we clarified the 5,6-dehydrokawain (1) and 7,8-dihydro-5,6-dehydrokawain (2) contents in the pericarps (0.16% and 0.55%, respectively), placenta (0.13% and 0.49%, respectively), and leaves (0.20% and 0.22%, respectively) of A. zerumbet [59]. We also found higher proportions of kavalactone dimers in the pericarps (5: 0.04%; 6: 0.01%; 7: 0.05%; 8: 0.02%) than in the placenta (5: 0.01%; 6: 0.003%; 7: 0.01%; 8: 0.003%) and leaves (5: 0.02%; 6: 0.008%; 7: 0.03%; 8: 0.006%) [59].
Various studies have reported the kavalactone contents in the extracts of medicinal parts of A. zerumbet [67,70,75,84,93]. In the study of Chompoo et al. [84], the concentration of 1 in hexane extracts was highest in the rhizomes of A. zerumbet (3.13 mg/g), followed by the flowers (2.22 mg/g), stems (2.08 mg/g), leaves (1.67 mg/g), pericarps (1.58 mg/g), and seeds (0.11 mg/g). Meanwhile, the concentration of 2 in hexane extracts was highest in the flowers (6.08 mg/g), followed by the rhizomes (5.41 mg/g), stems (3.70 mg/g), leaves (3.38 mg/g), seeds (0.22 mg/g), and pericarps (0.13 mg/g) [84]. The same group also extracted kavalactones 1 and 2 in ethanol and aqueous solvents [75]. In hexane extract, Elzaawely et al. [70] obtained a higher content of 2 from fresh rhizomes (424.4 mg/g) than from fresh leaves (148.7 mg/g). Cruz et al. [67] prepared infusions from A. zerumbet leaves collected in Rio de Janeiro. They reported a 2 concentration of 6.63 mg/g in the extract [67]. Xiao et al. [93]. clarified kavalactones 1 and 2, (±)-aniba dimer A (5), and alpingsin C (7) concentrations of 219.1, 301.4, 42.4, and 15.3 mg/g, respectively, in an ethyl acetate extract of the fruits.

2.3.2. Diterpenoids

Chompoo et al. [84] reported that the rhizomes of A. zerumbet yielded the highest (E)-labda-8(17),12-diene-15,16-dial (27) contents in hexane extract (3.97 mg/g), followed by seeds (2.91 mg/g) and pericarps (0.35 mg/g). Compound 27 was absent in the hexane extracts of stems, leaves, and flowers but was present in the ethanol extract of seeds (1.00 mg/g extract) and in aqueous extracts of the rhizome, pericarp, and seeds (0.81, 0.75, and 0.96  mg/g, respectively) [75].

2.3.3. Others

Victório et al. [140,141] reported the contents of kaempferol-3-O-glucuronide (23) (0.56%) and rutin (25) (0.15%) in the dried leaves of A. zerumbet.
Tavichakorntrakool et al. [79] revealed various phenolic compounds and flavonoids in A. zerumbet rhizomes: gallic acid (0.16 mg/g), protocatechuic acid (0.11 mg/g), p-hydroxybenzoic acid (0.09 mg/g), syringic acid (101) (0.14 mg/g), ferulic acid (99) (0.09 mg/g), rutin (25) (0.66 mg/g), myricetin (2.51 mg/g), quercetin (22) (9.07 mg/g), and kaempferol (20) (0.52 mg/g).
Xiao et al. [93] clarified the contents of 22, 71, 72, 99–101, and 104 in an ethyl acetate extract of the fruits.
Elzaawely et al. [96] quantitatively analyzed the phenolic compounds in fresh flowers and seeds. The flowers and seeds contained p-hydroxybenzoic acid (0.03 and 0.02 mg/g, respectively), syringic acid (101) (0.02 and 0.01 mg/g, respectively), vanillin (100) (0.006 and 0.01 mg/g, respectively), p-coumaric acid (0.005 and 0.004 mg/g, respectively), ferulic acid (99) (0.03 and 0.009 mg/g, respectively), and cinnamic acid (0.006 and 0.004 mg/g, respectively) [96].

2.4. Qualitative Analysis

GC–MS and LC–MS analyses of organic solvent extracts of A. zerumbet have been variously reported [16,25,59,60,64,70,87,95,96,139,142]. A GC–MS analysis by Kuster et al. [142] revealed the presence of kavalactones, 5,6-dehydrokawain (1) and 7,8-dihydro-5,6-dehydrokawain (2) in A. zerumbet leaves. da Cruz et al. [25] identified thirty-eight volatile organic compounds, seven proanthocyanidins, eleven flavonoids, and one carbohydrate in A. zerumbet leaves. Paulino et al. [16] clarified the volatile components in a 90% ethanol extract of the leaves. The most abundant compounds were 5,6-dehydrokawain (1) (8.3%), 7,8-dihydro-5,6-dehydrokawain (2) (19.4%), tocopherol (9.1%), β-sitosterol (71) (13.4%), and terpinen-4-ol (9.2%) [16]. Through an HPLC–ESI–MS/MS analysis, Ghareeb et al. [60] annotated the compounds in a methanol extract of A. zerumbet leaves. A total of 37 secondary metabolites were characterized as flavonoids (aglycones and glycosides) and benzoic and cinnamic acid derivatives. da Silva et al. [64] conducted an UHPLC/ESI–QTOF–MS analysis of A. zerumbet leaf extracts. They identified nine compounds: D-(+)-trehalose, (epi)catechin, procyanidin B2, quercetin-3-O-glucuronide, kaempferol-3-O-glucoside-3″-rhamnoside, kaempferol-3-O-glucuronide (23), isorhamnetin-3-O-neohesperidoside, alpinetin (18), and pinocembrin (16) in the leaves.
Hou et al. [87] identified 24 sesquiterpenes and 15 monoterpenes in the petroleum ether extract of the fruits.
In 2020, we clarified the chemical constituents in methanol extracts of A. zerumbet leaves, placenta, pericarps, and seeds using LC–MS [59]. Compounds 1, 2, and 5–8 were detected in the leaf, placenta, and pericarp extracts but were absent in the seed extracts [59]. Chompoo et al. [95] identified four steroids in the leaves, two steroids in the rhizomes and seeds, eight steroids in the pericarps, three steroids in the flowers, and five steroids in the stems of A. zerumbet. Another GC–MS analysis by Elzaawely et al. [70,96,139] revealed the presence of phenolic compounds in the ethyl acetate extracts of leaves, rhizomes, flower, and seeds.

3. Conclusions

A. zerumbet (Pers.) B.L.Burtt & R.M.Sm is a perennial plant widely distributed in South America, Oceania, and Asia. The medicinal properties of its leaves, rhizomes, fruits, seeds, and flowers are exploited in different clinical uses. The leaves of A. zerumbet have been consumed as antihypertensives and diuretics. The leaves are also believed to exhibit an anti-hemorrhoidal activity and to protect against the common cold. The rhizomes of A. zerumbet have been used to treat trauma, peptic ulcers, catarrh, and rheumatism. The seeds and fruits of A. zerumbet are traditionally used as an aromatic stomachic and cardiovascular disease treatment, respectively. A. zerumbet flowers have been used as a bronchitis treatment.
This review reveals that more than 100 compounds, including kavalactones, chalcones, flavonoids, terpenoids, diarylheptanoids, and neolignans, have been isolated from the leaves, rhizomes, fruits, pericarps, seeds, and flowers of this plant. This review also summarizes the chemical components of the organic solvent extracts and essential oils obtained from the various medicinal parts of A. zerumbet. The major components known at present are identified as the essential oil constituents, kavalactones, and flavonoids in the leaves; the essential oil constituents, kavalactones, flavonoids, and diterpenoids in the rhizomes; the essential oil constituents, kavalactones, and diterpenoids in the fruits (placenta, pericarps, and seeds); the essential oil constituents and diterpenoids in the seeds; and the essential oil constituents in the flowers. Most of the essential oils prepared from the leaves, rhizomes, and flowers of A. zerumbet are dominated by 1,8-cineole and terpinen-4-ol. No volatile components were found to uniquely accumulate in each medicinal part of the plant. These results contribute to the scientific validation of the traditional understanding that A. zerumbet possesses different medicinal properties in each plant part.
Although the chemical constituents of A. zerumbet have been extensively researched, phytochemical investigations have primarily focused on the leaves, rhizomes, and flowers of this plant; the fruit parts (pericarps, placenta, and seeds) have been comparatively limited. In addition, secondary metabolites such as chalcones, diarylheptanoids, and neolignans have been isolated from shell ginger but have not been quantitatively analyzed. Therefore, phytochemical investigation of A. zerumbet, especially of its fruit parts (pericarps, placenta, and seeds), and comparative quantitative investigations of the phytochemicals in the multiple medicinal parts (leaves, rhizomes, fruits, seeds, and flowers) would be valuable.

Author Contributions

Conceptualization, Y.N.; funding acquisition, K.T.; investigation, Y.N.; methodology, Y.N.; visualization, Y.N.; writing—original draft preparation, Y.N.; writing—review and editing, Y.N. All authors have read and agreed to the published version of the manuscript.

Funding

This research received no external funding.

Conflicts of Interest

The authors declare no conflict of interest.

Correction Statement

This article has been republished with a minor correction to the readability of tables (Table 3 and Table 4). This change does not affect the scientific content of the article.

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Molecules 29 02845 g001
Figure 1. Structures of the kavalactones, chalcones, flavonoids, diterpenoids, and sesquiterpenoids isolated from A. zerumbet.
Figure 1. Structures of the kavalactones, chalcones, flavonoids, diterpenoids, and sesquiterpenoids isolated from A. zerumbet.
Molecules 29 02845 g001
Molecules 29 02845 g002
Figure 2. Structures of the monoterpenoids, meroterpenoids, steroids, diarylheptanoids, neolignans, glucoside esters, phenolic compounds, and other compounds isolated from A. zerumbet.
Figure 2. Structures of the monoterpenoids, meroterpenoids, steroids, diarylheptanoids, neolignans, glucoside esters, phenolic compounds, and other compounds isolated from A. zerumbet.
Molecules 29 02845 g002
Table 1. Bioactivities of the extracts and essential oils of multiple medicinal parts of A. zerumbet.
Table 1. Bioactivities of the extracts and essential oils of multiple medicinal parts of A. zerumbet.
Plant partsExtractsBioactivitiesReferences
LeavesEssential oilAcaricidal[31]
Anti-aging[32]
Anti-hypertensive[33,34]
Antimicrobial[14,35,36,37,38]
Anti-nociceptive[39]
Antioxidant[32,40,41,42]
Antiparasitic[43]
Antipsychotic[40,44]
Anti-schizophrenic[45]
Antispasmodic[46]
Anxiolytic-like[47,48,49]
Depressant[44]
Larvicidal[38,50,51]
Insecticidal[52,53]
Anti-melanogenic[32]
Molluscicidal[51]
Myorelaxant[46]
Repellent[53]
Tyrosinase inhibitory[38]
Vasorelaxant[17,54,55]
Aqueous extractAntioxidant[38]
Antiviral[56]
Longevity-extending[57]
Singlet oxygen quenching[58]
Methanol extractAnti-inflammatory[59,60]
Anti-nociceptive[60]
Antioxidant[27,38,60,61,62]
Antipyretic[60]
50% Ethanol extractAnti-hypertensive[63]
Vasodilator[63,64]
70% Ethanol extractAntidepressant-like[65,66]
Antioxidant[66]
Anxiolytic-like[66]
80% Ethanol extractAntioxidant[67]
90% Ethanol extractCardioprotective[16]
Ethanol extractAntioxidant[68]
Photoprotective[68]
Dichloromethane extractsAntiproliferative[69]
Ethyl acetate extractAntioxidant[70]
n-Hexane extractAnti-obese[71]
TeaDiuretic[72,73]
RhizomesEssential oilAntimicrobial[36,74]
Aqueous extractAnti-skin disease[75]
Antioxidant [75]
Antiviral[56]
Hepatoprotective[76]
Methanol extractAntimicrobial[77]
Antioxidant[77]
Hepatoprotective[76,78]
50% Ethanol extractAntibacterial[79]
Cytotoxicity[80]
95% Ethanol extractAnti-Helicobacter pylori[81]
Ethanol extractAnalgesic[82]
Anti-inflammatory[82]
Tyrosinase inhibitory[83]
n-Hexane extractAntiglycation[84]
FruitsEssential oilAnalgesic[85]
Anti-atherosclerotic[86]
Anti-inflammatory[85,87]
Antimicrobial[87]
Endothelial protective[7,22,88,89,90]
Neuroprotective[91]
Vasodilator[92]
Ethyl acetate extractAnti-hypertensive[93]
SeedsEssential oilAntimicrobial[38]
Hypolipidemic[18,94]
Larvicidal[38]
Tyrosinase inhibitory[38]
Aqueous extractAntioxidant[38,75]
Acetone extractAntiatherogenic[95]
Methanol extractAntioxidant[38]
Ethyl acetate extractAntioxidant[96]
PowderHypolipidemic[18,94]
FlowersEssential oilAntimicrobial[97]
Insecticidal[97]
Methanol extractAnticancer[98]
Dichloromethane extractAnticancer[98]
Ethyl acetate extractAntioxidant[96]
Table 2. Compounds isolated from the multiple medicinal parts of A. zerumbet.
Table 2. Compounds isolated from the multiple medicinal parts of A. zerumbet.
CompoundsSourceReferences
KavalactonesLRFrPeSeFl
5,6-Dehydrokawain (1)++++−+[15,19,56,59,69,93,98,104,105,106,107,108,109]
7,8-Dihydro-5,6-dehydrokawain (2)++++−−[15,19,56,59,69,93,104,105,106,107,108,110]
4′-Hydroxyl dihydro-5,6-dehydrokavain (3)+−−−−−[111]
4-Hydroxy-6-(4-methoxyphenethyl)-2H-pyran-2-one (4)−+−−−−[106]
(±)-Aniba dimer A (5)+−++−−[59,93,110,111]
(±)-Aniba dimer C (6)+−−+−−[59,111]
Alpingsin C (7)+−++−−[59,93,111]
Alpingsin D (8)+−−+−−[59,111]
ChalconesLRFrPeSeFl
Pinocembrin chalcone (9)−+−−−−[109]
Cardamonin (10)−+−++−[105,108,109,112]
Flavokawin B (11)−+−−−−[105]
Uvangoletin (12)−−−+−−[108]
Dihydroflavokawin B (13)−+−−−−[105]
FlavonoidsLRFrPeSeFl
(+)-Catechin (14)+−−−−−[15]
(−)-Epicatechin (15)+−−−−−[15]
Pinocembrin (16)++−−−−[109,113]
Pinostrobin (17)+−−−−−[69]
Alpinetin (18)−+−−+−[105,112]
Naringenin (19)−+−−−−[109]
Kaempferol (20)+−−−−−[69]
3-Methoxykaempferol (21)−+−−−−[109]
Quercetin (22)−++−−−[93,106]
Kaempferol-3-O-glucuronide (23)++−−−−[15,114]
Kaempferol-3-O-rutinoside (24)+−−−−−[15]
Rutin (25)+−−−−−[15]
DiterpenoidsLRFrPeSeFl
Zerumin D3 (26)−+−−−−[115]
(E)-Labda-8(17),12-diene-15,16-dial (27)−+−−+−[28,56,84,106,114,116]
Zerumin A (28)−−−−+−[117]
Pahangensin B (29)−+−−−−[115]
Zerumin D1 (30)−+−−−−[115]
Zerumin D2 (31)−+−−−−[115]
Zerumin D8 (32)−+−−−−[115]
Zerumin D9 (33)−+−−−−[115]
Zerumin D10 (34)−+−−−−[115]
Zerumin B (35)−−−−+−[117]
Villosin (36)−+−−−−[115]
Zerumin (37)−+−−+−[20,115]
Coronarin E (38)−−−−+−[117]
Labda-8(17),13(14)-dien-15,16-olide (39)−+−−−−[115]
(12S)-15,16-Epoxy-12-hydroxy-labda-8(17),13(16),14-triene (40)−+−−−−[115]
(12R)-15,16-Epoxy-12-hydroxy-labda-8(17),13(16),14-triene (41)−+−−−−[115]
(12E)-Labda-8(17),12(13)-dien-16,15-olide (42)−+−−−−[115]
Coronarin D ethyl ether (43)−+−−−−[115]
(12E)-Labda-8(17),12,14-trien-16,15-olide (44)−+−−−−[115]
Zerumin D11 (45)−+−−−−[115]
Zerumin D12 (46)−+−−−−[115]
12,15-Epoxylabda-8(17),12,14-trien-16-al (47)−+−−−−[115]
Obtunone (48)−+−−−−[115]
Podocarpa-8,11,13-trien-12-ol (49)−+−−−−[115]
Zerumin D13 (50)−+−−−−[115]
Podocarpa-8,11,13-trien-13-ol (51)−+−−−−[115]
(11E)-14,15,16-Trinorlabda-8(17),11-dien-13-al (52)−+−−−−[115]
(11E)-14,15,16-Trinorlabda-8(17),11-dien-13-oic acid (53)−+−−−−[115]
Zerumin D14 (54)−+−−−−[115]
(E)-15,16-Bisnorlabda-8(17),11-dien-13-one (55)−+−−+−[28,117]
13,14,15,16-Tetranorlabda-8(l7)-en-12-oic acid (56)−+−−−−[115]
Isodrimenin (57)−+−−−−[115]
Zerumin D4 (58)−+−−−−[115]
SesquiterpenoidsLRFrPeSeFl
Zerumin D6 (59)−+−−−−[115]
Zerumin D5 (60)−+−−−−[115]
α-Cadinol (61)−+−−−−[115]
α-Eudesmol (62)−+−−−−[115]
β-Eudesmol (63)−+−−−−[115,118]
γ-Eudesmol (64)−+−−−−[115]
Caryophyllenol I (65)−+−−−−[115]
(±)-Humulene epoxide II(66)−+−−−−[118]
Nerolidol (67)−+−−−−[118]
MonoterpenoidsLRFrPeSeFl
2′-Methoxy-4′-oxo-6′-phenyl-2′E-hexenoic acid 4-hydroxy-2-isopropyl-5-methylphenyl
ester (68)		−−−+−−[108]
2′-Methoxy-4′-oxo-6′-phenyl-2′E-hexenoic acid 4-hydroxy-5-isopropyl-2-methylphenyl
ester (69)		−−−+−−[108]
MeroterpenoidsLRFrPeSeFl
Zerumin D7 (70)−+−−−−[115]
SteroidsLRFrPeSeFl
β-Sitosterol (71)−−+−−−[93]
Cholestenone (72)−−+−−−[93]
DiarylheptanoidsLRFrPeSeFl
1,2-Dihydro-bis(de-O-methyl)curcumin (73)−+−−−−[119]
(4E,6E)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-phenylhepta-4,6-dien-3-one (74)−+−−−−[119]
(3S,7S)-5,6-Dehydro-4″-de-O-methylcentrolobine (75)−+−−−−[119]
1,7-Diphenyl-5-heptene-3-one (76)−+−−−−[119]
(−)-(R)-4″-Hydroxyyashabushiketol (77)−+−−−−[119]
(3S,5S)-Alpinikatin (78)−+−−−−[119]
5S-Ethoxyl-7-(4-hydroxy-3-methoxyphenyl)-1-phenyl-3-heptanone (79)−+−−−−[119]
NeolignansLRFrPeSeFl
9-Benzoyloxy-3,3′-dimethoxy-8′,9′-dinor-7′,8-neoligane-4,4′,7-triol (80–83)−+−−−−[119]
9-Benzoyloxy-3,7-dimethoxy-8,9′-neoligane-4,4′-diol (84–86)−+−−−−[119]
1,5-Di(3′-methoxyphenyl-4′-hydroxy)-2-[(benzyloxy)methyl]-pent-4-en-1-yl
benzoate (87)		−+−−−−[119]
7,8-erythro-3,3-Dimethoxy-9,9′-dibenzoyloxy-5′,8-neoligane-4,4′,7-triol (88)−+−−−−[119]
Quiquelignan H (89)−+−−−−[119]
Morinol G (90)−+−−−−[119]
(1R,2R,4E)-1,5-Bis(3,4-dimethoxyphenyl)-2-(methoxymethyl)pent-4-en-1-ol (91)−+−−−−[119]
(4E)-1,5-Bis(4-hydroxyphenyl)-2-(hydroxymethyl)-4-penten-1-ol (92)−+−−−−[78]
1,2-Bis-(3-methoxy-4-hydroxyphenyl)-1,3-propanediol (93)−+−−−−[119]
Glucoside estersLRFrPeSeFl
Ethyl 4-O-feruloyl-β-glucopyranoside (94)−+−−−−[120]
4-Hydroxy-3-methoxyphenyl 4-O-feruloyl-β-glucopyranoside (95)−+−−−−[120]
Phenolic compoundsLRFrPeSeFl
Chavicol-β-rutinoside (96)−+−−−−[78]
1,2,Di-O-β-D-glucopyranosyl-4-allylbenzene (97)−+−−−−[78]
trans-Cinnamic acid methyl ester (98)−+−−−−[105]
Ferulic acid (99)−−+−−−[93]
Vanillin (100)−−+−−−[93]
Syringic acid (101)−−+−−−[93]
OthersLRFrPeSeFl
(E)-2,2,3,3-Tetramethyl-8-methylene-7-(oct-6-en-1-yl)octahydro-1H-quinolizine (102)−−−−+−[116]
2,5-Bis (1E,3E,5E)-6-methoxyhexa-1,3,5-trien-1-yl-2,5-dihydrofuran (103)−+−−−−[116]
Oleamide (104)−−+−−−[93]
Abbreviations denote the plant parts: L: leaves, R: rhizomes, Fr: fruits, Pe: pericarps, Se: seeds, and Fl: flowers.
Table 3. Composition of the essential oils prepared from the leaves of A. zerumbet.
Table 3. Composition of the essential oils prepared from the leaves of A. zerumbet.
CompoundsRelative Contents of the Essential Oils
LLLLLLLLLLLLLLLLLLLLLLLLLLLLLLL
BRABRABRABRABRABRABRABRABRABRABRABRABRABRAJPNJPNJPNJPNJPNJPNJPNJPNJPNJPNJPNJPNJPNJPNMTQEGYFJI
α-Thujene+ ++++++++++ +++
α-Pinene+++ +++++++++++++++++++++ ++++++++
Camphene ++++++++++ ++++
Sabinene++++ +++++++++++++++++++ ++ +++ ++ +++
β-pinene+++ ++++++ + +++++++++++ +++++++
Myrcene + + +++ + ++ +
α-Phellandlene ++
α-Terpinene+++ ++++ +++ + ++
p-Cymene+++ ++++++++++ ++++++++++++++++++++++++++++++++++++++++++++++++
Limonene+++++ ++ ++ +++++++++++++ +++++
1,8-Cineole++ ++ +++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++
γ-Terpinene++++++++++++++ ++++++++++++++ ++ +++ ++ ++++
trans-4-Thujanol + + + ++
Terpinolene + +++ ++ +
Linalool ++ +++ ++ +++++++++++ ++
Camphor ++++++++ ++++++ +
Borneol +++++ +++
Terpinen-4-ol++++++++ +++++++++++++++++++++++++++++++++++++++++++++++++ ++++++++
++
Cryptone + +
α-Terpineol+++ + + ++ + ++
Cuminaldehyde + +++ ++++
(E)-Methyl cinnamate ++ +++++ + ++
β-Caryophyllene+++ ++++ +++ +++++ ++ ++ + ++++
α-Humulene ++ + +++ +++++
Elemol
(E)-Nerolidol +
Caryophyllene oxide ++++ + ++++ + + +++++
10-Epi-γ-eudesmol
γ-Eudesmol +
β-Eudesmol
α-Eudesmol
References[124][2][125][126][126][41][37][34][31][127][52][128][51][54][4][4][4][4][4][4][4][4][4][4][70][47][49][129][14][36][8]
The material source is L: leaves. The plant collection regions are BRA: Brazil, JPN: Japan, MTQ: Martinique, EGY: Egypt, and FJI: Fiji. The relative contents of compounds in the essential oils are + (1.0–9.9%), ++ (10.0–19.9%), +++ (20.0–29.9%), ++++ (30.0–39.9%), +++++ (40.0–49.9%).
Table 4. Composition of the essential oils prepared from the leaves, rhizomes, fruits, seeds, and flowers of A. zerumbet.
Table 4. Composition of the essential oils prepared from the leaves, rhizomes, fruits, seeds, and flowers of A. zerumbet.
CompoundsRelative Contents in the Essential Oils
LLLRRRRRRRFrFrFrSeSeSeFlFlFlFlFlFlFlFlFlFlFlFl
INDTWNCHNINDINDINDMTQEGYFJIJPNCHNCHNCHNTWNTWNJPNMTQMTQMTQMTQMTQMTQVNMJPNBRAINDINDCHN
α-Thujene+ + +++ + ++
α-Pinene++++ ++ +++++ +++ +++ ++ +
Camphene ++ + + ++++ +
Sabinene++ ++ + ++++++ ++++++++ +++++
β-pinene+++ ++ + ++++++++++ ++++ +
Myrcene + + + + + +++ + +
α-Phellandlene ++ + ++ +
α-Terpinene + + +++++ +
p-Cymene+ + ++ +++++ +
Limonene+ ++ + +
1,8-Cineole++++++++++ +++++ ++++ ++ ++++++++++++++++++++++++
γ-Terpinene++ ++ ++ + +++++++ ++++
trans-4-Thujanol+ + + ++
Terpinolene + +++++
Linalool+++ + ++ + ++++++ + +++
Camphor +++++ ++++ +++ ++ +
Borneol +++ ++ + + +
Terpinen-4-ol+++++++++++
++		+++
++		++++++
++		 +++ +++++++++++++++++++ ++++
++		+++++++
Cryptone + + + + + +
α-Terpineol++++++++ ++++ +++++++++++ +++
Cuminaldehyde +
(E)-Methyl cinnamate ++
β-Caryophyllene + ++++ ++++ ++++++++ + ++
α-Humulene + ++ +
Elemol + + ++ +
(E)-Nerolidol ++ + + + + ++ + +
Caryophyllene oxide ++ + + +++ + + +++ + + +
10-Epi-γ-eudesmol + +
γ-Eudesmol + ++ +
β-Eudesmol + + + + +
α-Eudesmol + +
References[130][38][53][130][74][131][14][36][8][70][92][53][87][18][38][96][14][97][97][97][97][97][132][96][125][133][130][53]
The material sources are L: leaves, R: rhizomes, Fr: fruits, Se: seeds, and Fl: flowers. The plant collection regions are IND: India, TWN: Taiwan, CHN: China, MTQ: Martinique, EGY: Egypt, FJI: Fiji, JPN: Japan, VNM: Vietnam, and BRA: Brazil. The relative contents of compounds in the essential oils are + (1.0–9.9%), ++ (10.0–19.9%), +++ (20.0–29.9%), ++++ (30.0–39.9%), +++++ (40.0–49.9%).
Table 5. Contents of major kavalactones in multiple medicinal parts of A. zerumbet.
Table 5. Contents of major kavalactones in multiple medicinal parts of A. zerumbet.
CompoundsPlant PartsSolventContent (%)References
5,6-Dehydrokawain (1)Fresh leavesEthanol0.01[138]
Dried leavesn-Hexane0.07[107]
Methanol0.20[59]
Fresh rhizomesEthanol0.10[138]
Dried pericarpsn-Hexane0.21[107]
Methanol0.16[59]
Dried seedsn-Hexane0.05[107]
Dried placentaMethanol0.13[59]
Fresh stemsEthanol0.02[138]
7,8-Dihydro-5,6-dehydrokawain (2)Fresh leavesEthanol0.41[138]
Water0.07[139]
Dried leavesn-Hexane0.39[107]
Methanol0.22[59]
Fresh rhizomesEthanol0.35[138]
Dried pericarpsn-Hexane0.54[107]
Methanol0.55[59]
Fresh seedsWater0.0003[96]
Dried seedsn-Hexane0.14[107]
Fresh flowersWater0.03[96]
Dried placentaMethanol0.49[59]
Fresh stemsEthanol0.08[138]
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Nishidono, Y.; Tanaka, K. Phytochemicals of Alpinia zerumbet: A Review. Molecules 2024, 29, 2845. https://doi.org/10.3390/molecules29122845

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Nishidono Y, Tanaka K. Phytochemicals of Alpinia zerumbet: A Review. Molecules. 2024; 29(12):2845. https://doi.org/10.3390/molecules29122845

Chicago/Turabian Style

Nishidono, Yuto, and Ken Tanaka. 2024. "Phytochemicals of Alpinia zerumbet: A Review" Molecules 29, no. 12: 2845. https://doi.org/10.3390/molecules29122845

APA Style

Nishidono, Y., & Tanaka, K. (2024). Phytochemicals of Alpinia zerumbet: A Review. Molecules, 29(12), 2845. https://doi.org/10.3390/molecules29122845

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