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Mallotus Species from Vietnamese Mountainous Areas: Phytochemistry and Pharmacological Activities

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Mallotus Species from Vietnamese Mountainous Areas: Phytochemistry and Pharmacological Activities Phytochem Rev (2010) 9:217–253 DOI 10.1007/s11101-009-9152-6 Mallotus species from Vietnamese mountainous areas: phytochemistry and pharmacological activities C. Rivie`re • V. Nguyen Thi Hong • Q. Tran Hong • G. Chataigne´ • N. Nguyen Hoai • B. Dejaegher • C. Tistaert • T. Nguyen Thi Kim • Y. Vander Heyden • M. Chau Van • J. Quetin-Leclercq Received: 31 July 2009 / Accepted: 5 October 2009 / Published online: 28 October 2009 Ó Springer Science+Business Media B.V. 2009 Abstract The genus Mallotus belongs to Malphighi- an altitude below 1,000 m, but some species can grow ales order and Euphorbiaceae family. Mallotus, com- at an altitude of 2,000 m, such as Mallotus oreophilus monly known as ‘‘Ba bet’’ in Vietnam, is one of the Mu¨ll. Arg. Some Mallotus species are known to most diverse and richest genera of the Euphorbiaceae contain different natural compounds, mainly diterpe- family in Vietnam, where about 40 Mallotus species noids, triterpenoids, steroids, flavonoids, coumarino- may be found. Some Mallotus species are used in lignoids, phloroglucinol derivatives or benzopyrans, traditional medicine in Vietnam for different indica- and to exhibit interesting biological activities such as tions. They are concentrated in mountainous areas with antimicrobial, antioxidant, antiviral, or cytototoxic ones. Some of these properties may be explained by their chemical composition as, for example, benzopy- C. Rivie`re Á G. Chataigne´ Á J. Quetin-Leclercq rans accounting for the cytotoxicity of Mallotus apelta Analytical Chemistry, Drug Analysis and Pharmacognosy extracts. However, although these species seem to have Unit, Universite´ Catholique de Louvain, Avenue E. a great medicinal potential, the existing knowledge Mounier, 7, 1200 Brussels, Belgium about most Mallotus species is still in most cases very C. Rivie`re (&) limited. This review underlines the interest to continue Department of Pharmacology, INSERM U657, Universite´ the study of this genus of the Euphorbiaceae. Victor Segalen Bordeaux 2, 33076 Bordeaux Cedex, France e-mail: [email protected] Keywords Mallotus Á Euphorbiaceae Á Vietnam Á Natural compounds Á Biological activities V. Nguyen Thi Hong Á Q. Tran Hong Á N. Nguyen Hoai Á T. Nguyen Thi Kim Á M. Chau Van Institute of Natural Products Chemistry, Vietnamese Academy of Science and Technology, 18 Hoang Quoc Introduction Viet Road, Nghia Do Cau Giay, Hanoi, Vietnam The genus Mallotus, commonly known as ‘‘Ba bet’’ in N. Nguyen Hoai Á B. Dejaegher Á C. Tistaert Á Vietnam, is one of the most diverse and richest genera Y. Vander Heyden Analytical Chemistry and Pharmaceutical Technology of the Euphorbiaceae family in Vietnam where about (FABI), Vrije Universiteit Brussel, Laarbeeklaan, 40 Mallotus species may be found among which six 103, 1090 Brussels, Belgium species and one variety are endemic. These endemic species, Mallotus canii Thin, Mallotus chuyenii Thin, T. Nguyen Thi Kim University of Natural Science, Vietnamese National Mallotus eberhardtii Gagnep., Mallotus hanheoensis University, Hanoi, Vietnam Thin, Mallotus poilanei Gagnep., Mallotus 123 218 Phytochem Rev (2010) 9:217–253 sathavensis Thin, Mallotus cuneatus Ridl. var. glab- compounds isolated from the Mallotus genus and ratus Thin, have been recently found, distributed in extracts show many different biological activities several regions in Vietnam and there is still a lack of including antioxidant, antiviral, antimicrobial, anti- information about them. Species belonging to the inflammatory or cytotoxic. Some of these properties Mallotus genus are usually shrubs or small trees and are attributed to the presence of specific classes of grow in rainy, ever green primary or secondary natural compounds, for example, benzopyrans forests. They can be also found in deciduous forests. accounting for the cytotoxicity of Mallotus apelta Some species are considered as ‘‘first-coming plants’’ extracts (Van Chau et al. 2005a; Van Kiem et al. of forests recycling. Naturally, species are chiefly 2004) or polyphenols accounting for the antiradical propagated from seeds. They are concentrated in activity of Mallotus metcalfianus extracts (Rivie`re mountainous areas with an altitude below 1,000 m, et al. 2009). but some species can grow at an altitude of 2,000 m, In this review paper, we will summarize the data such as Mallotus oreophilus Mu¨ll. Arg. (Thin 2003). of the literature concerning the phytochemistry and The genus Mallotus belongs to the Malphighiales the pharmacological activities of Mallotus species, order, the Euphorbiaceae family, Acalyphoideae sub- described over the past few decades (Table 1; Fig. 1). family, Acalypheae pro parte, Rottlerinae subtribe (Nowicke and Takahashi 2002). This genus includes approximately 150 species distributed in tropical and Phytochemistry sub-tropical regions in Asia (Cambodia, China, India, Laos, Malaysia, Sri Lanka, Thailand, Vietnam). A few For some Mallotus species, studies were published on species are found in the North and East of Australia their chemical composition, especially for M. apelta, and the Pacific-Ocean Archipelago (the East of Fiji). M. metcalfianus, M. philippinensis, M. paniculatus, Only two species are found in Africa and Madagascar M. repandus. These Mallotus species are known to (Schatz 2001). M. oppositifolius (Geiseler) Mu¨ll. Arg. contain different natural compounds, mainly diterpe- is distributed in different African countries (Central noids, triterpenoids, steroids, benzopyranes, flavonoids, Africa, Ghana, Nigeria, Tanzania) and Madagascar. coumarinolignoids or phloroglucinol derivatives. The M. baillonianus Mu¨ll. Arg. is endemic to Madagascar. existing knowledge about the other investigated plants The genus Mallotus is richer in Vietnam than in is in most cases very limited. However, some data China, where 28 species are described of which seven underline the isolation of a novel furanocarboxamide are endemic. Sixteen species are common in Vietnam from M. cuneatus (Groweiss et al. 1994), scopoletin and China. In general, these species are distributed in from M. resinosus (Ma et al. 2004), phloroglucinol higher altitude in China than Vietnam (Qiu and derivatives from M. pallidus (Supudompol et al. 2004; Gilbert 2008). Some species of the genus Mallotus Likhitwitayawuid and Supudompol 2005) or triterpe- (M. apelta, M. barbatus, M. floribundus, M. glabri- noids and casbane-type diterpenoid lactones from usculus, M. macrostachyus, M. oblongifolius, M. hookerianus (Hui and Li 1976; Bai et al. 2006). M. paniculatus, M. philippinensis, M. poilanei) are used as medicinal plants in the traditional medicine in Terpenoids and steroids Vietnam and the South-East Asian countries for the treatment of various ailments ranging from minor Diterpenoids and diterpenic lactones (Table 2) infections such as gastrointestinal disorders to dysen- tery, hepatic diseases, cutaneous diseases, fever and Cheng et al. (1999) and Cheng and Chen (1999) malaria, and a series of other indications. The isolated five new diterpenoids (1–5) from the petro- researched parts of the Mallotus species include leum ether fraction of the ethanolic extract of aerials parts, bark, heartwood, leaves, roots, seeds, M. apelta. Three highly oxidized casbane-type diter- stem bark and whole plants. Some Mallotus species penoids with unique a,b-unsatured c-lactones, named are known to contain different natural compounds, hookerianolides A, B, and C (6–8), were isolated from mainly terpenoids, polyphenols and benzopyrans. The the methylene chloride extract of M. hookerianus (Bai 123 Phytochem Rev (2010) 9:217–253 Table 1 Vietnamese Mallotus species Botanical name Synonymsa Vietnamese Plantb Distributionc Altitude Altitude Traditonal Phytochemistryf,g Pharmacological vernacular names Vietnam China (m) usesd,e activitiesg (m) Mallotus ND Ruoikhe T V (South 100–500 ND ND ND ND anisopodus province Airy Shaw AG), Ca, L Mallotus apelta Ricinus apelta Babet trang, Buc Sm T, V (N to S), 100–700 100–1,000 B: dh, ga, L: benzopyrans1,2,3,4, Antiviral D-HBV20 (Lour.) Mu¨ll. Lour. trang, Bui bui, Sh Ch gy, hem, pentacyclic triterpenoids Bacteriostatic: Arg. Bai bai, Bum bup, hep, oe and steroids5,6,7,8, 6,9,10 triterpenoids and Bang bac, Cay L: co, cu, flavonoids , benzopyrans1,13 ruong carotenoids11, dh, gy, Cytotoxic: benzopyrans4 hep, oe, anthraquinone, coumarin 12 Hepatoprotective: ot and nicotinic acid coumarinolignoids17,21 R: ai, dh, R: pentacyclic triterpenoids 13 Inhibitory effect of ga, gy, and steroids , pyridine reverse transcriptase hep, oe type alkaloid and ellagic acid derivative14 and cellular DNA polymerase22 S: pentacyclic triterpenoids and steroids15, iridoid Inhibitory effect of (mussaenoside)15, NFAT transcription coumarinolignoids16,17 and NF-jB activation11 Wp: diterpenoids18,19 Mallotus Rottlera barbata Bung buc, Bup Sm T, V (N to S), 100– 200–1,300 B: ga L: polyprenols23 ND barbatus Wall. bong gai, Bong Sh Ch, Ind, L, 1,100 L: ac, hem, (Wall.) Mu¨ll. bet, Bung buc gai, Mal, Mya, oe, sc Arg. Ba bet long, Ruoi Th R: an, fe, cau, Cam lon, diu, cho, Nhung dien rau hea Mallotus canii ND Babet gialai T Endemic V 100–500 ND ND ND ND Thin (South province GL) Mallotus M. contubernalis var. Babet qua vang, Sm V (North 100–500 500–1,000 ND ND Antiviral HIV24 chrysocarpus chrysocarpus Ruoi trai vang Sh province Pamp. (Pamp.) Hand.- HT) Ch Mazz., M. repandus 123 var. chrysocarpus (Pamp.) S.M. Hwang 219 220 123 Table 1 continued Botanical name Synonymsa Vietnamese vernacular Plantb Distributionc Altitude Altitude Traditonal Phytochemistryf,g Pharmacological names Vietnam China usesd,e activitiesg (m) (m) Mallotus ND Babet hoabinh T Endemic V 100–500 ND ND ND ND chuyenii Thin (North province HB) Mallotus ND Ruoi clelland, Ruoi tron, Sm T, V (South 100–500 ND ND ND ND clellandii Ruoi khong long, Sh provinces), Hook.f. Nhung dien clelland, Ca, L, Mya, Nhung dien khong Th long Mallotus M. repandus var. Babet, Don xuong, Sm T, V (North 100–500 100–600 ND ND ND contubernalis repandus, M. Canhkien la bac, Sh provinces), Hance repandus var. Buctruong ba ngan, Ch, L scabrifolius (A. Rem ban day Juss.) Mu¨ll. Arg. Mallotus M. resinosus var. Duoi rung, Ruoi rung Sm T, V (N to S), Ca, 100–500 ND ND L, T: furanocarboxamide25 ND cuneatus Ridl.
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