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Chemistry and Pharmacology of Siraitia Grosvenorii: a Review LI Chun1, LIN Li-Mei2, SUI Feng1*, WANG Zhi-Min1, HUO Hai-Ru1, DAI Li1, JIANG Ting-Liang1

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Chemistry and Pharmacology of Siraitia Grosvenorii: a Review LI Chun1, LIN Li-Mei2, SUI Feng1*, WANG Zhi-Min1, HUO Hai-Ru1, DAI Li1, JIANG Ting-Liang1 Chinese Journal of Natural Chinese Journal of Natural Medicines 2014, 12(2): 0089−0102 Medicines doi: 10.3724/SP.J.1009.2014.00089 Chemistry and pharmacology of Siraitia grosvenorii: A review LI Chun1, LIN Li-Mei2, SUI Feng1*, WANG Zhi-Min1, HUO Hai-Ru1, DAI Li1, JIANG Ting-Liang1 1 Institute of Chinese Material Medica, China Academy of Chinese Medical Sciences, Beijing 100700, China; 2 Hunan University of Traditional Chinese Medicine, Changsha 410208, China Available online 20 Feb. 2014 [ABSTRACT] Siraitia grosvenorii is a perennial herb endemic to Guangxi province of China. Its fruit, commonly known as Luo hanguo, and has been used for hundreds of years as a natural sweetener and as a traditional medicine for the treatment of pharyngitis, pharyn- geal pain, as well as an anti-tussive remedy in China. Based on ninety-three literary sources, this review summarized the advances in chemistry, biological effects, and toxicity research of S. grosvenorii during the past 30 years. Several different classes of com- pounds have been isolated or detected from various parts of S. grosvenorii, mainly triterpenoids, flavonoids, polysaccharides, amino acids, and essential oils. Various types of extracts or individual compounds derived from this species exhibited a wide array of biological effects e.g. anti-tussive, phlegm-relieving, anti-oxidant, immunomodulatory, liver-protecting, glucose-lowering, and anti-microbial. The existing research has shown that extracts and individual compounds from S. grosvenorii are basically non-toxic. Finally, some suggestions for further research on specific chemical and pharmacological properties of S. grosvenorii are proposed in this review. [KEY WORDS] Siraitiagrosvenorii; Cucurbitaceae; Chemical constituents; Pharmacological effects [CLC Number]R284; R285 [Document code] A [Article ID]2095-6975(2014)02-0089-14 [2] . In 1987, S. grosvenorii fruit was listed as a medicinal Introduction and edible species by the China Ministry of Health [3]. To Siraitia grosvenorii is a perennial vine of the Cucur- date, S. grosvenorii fruit has been shown to have the fol- bitaceae family, and its fruit is commonly known as Luo lowing effects: antitussive, anti-asthmatic, anti-oxidation, hanguo (LHG). A total of seven species belong to the ge- liver-protection, glucose-lowering, immunoregulation, and [4] nusSiraitia, and these plants are distributed mostly in south anti-cancer . S. grosvenorii contains triterpenoids, flavon- [5] China, the Indo-China Peninsula, and Indonesia. There are oids, vitamins, proteins, saccharides, and a volatile oil . four species in China, among which Siraitia grosvenorii Mogrosides, a group of triterpenoid glycosides isolated (Swingle) C. Jeffreyex A. M. Lu and ZhiY. Zhang and from S. grosvenorii fruit, are regarded as the main active Siraitiasiamensis(Craib) C. Jeffrey ex S. Q. Zhong & D. ingredients for the sweet taste, and responsible for the Fang are usually used as medicinal plants. S. grosvenoriis main biological effects of S. grosvenorii. LHG products endemic to China, and principally grows in Guangxi prov- have been approved as dietary supplements in Japan, the ince, where it has been cultivated for more than 200 years [1] United States, New Zealand and Australia. Currently, the (Fig. 1). S. grosvenorii fruit has been used for centuries in extracts or some compounds from LHG are used mainly for China as a natural sweetener and as a traditional medicine their anti-tussive, expectorant, anti-diabetic, or sweet prop- for the treatment of lung congestion, colds, and sore throat erties in various Chinese herbal compound prescriptions or dietary supplements. In this review, the research progress of S. grosvenorii during the last 30 years is summarized. [Received on] 15-Dec.-2012 Chemical Composition [Research funding] This project was supported by the Beijing Joint Project Specific Funds, National Natural Science Foundation of Several different classes of compounds were previously China (Nos. 30873393, 81274112, 81373986) and the Beijing Mu- isolated from various parts of S. grosvenorii, with the main nicipal Natural Science Foundation (Nos. 7112098, 7132152). groups being triterpenoids, particularly the cucurbitane-type [*Corresponding author] SUI Feng: Prof., Tel.: 86-10-64041008, triterpenoid glycosides, flavonoids, polysaccharides, proteins Fax: 86-10-64041008, E-mail: [email protected] These authors have no conflict of interest to declare. and essential oils. – 89 – LI Chun, et al. / Chin J Nat Med, 2014, 12(2): 89−102 of one part in ten thousand are 425 and 563 times as sweet as that of 5% sucrose, respectively [17]. In addition, a series of cucurbitane tetracyclic triterpenoid acids, including siratic acids A-F were isolated from the root of S. grosvenorii [18-21]. So far, a total of forty-seven triterpenoids (Table 1) have been isolated, and/or detected in the fruit, roots, or leaf materials of S. grosvenorii. As shown in studies of the structure-taste relationships for the glycosides of 3β-hydroxy-cucurbit-5-ene derivatives, the number of glucose units, the oxygen function at the 11-position of the aglycone moiety, the location of the gly- cosyl units, and the hydroxylation of the side chain, are ap- parently responsible for the perception of taste [17, 30-31]. The Fig. 1 Line drawing of S. grosvenorii: 1. stem; 2. leaf; 3. presence of at least three sugar units in the molecule is essen- inflorescence; 4. fruit tial for the occurrence of taste. For example, compounds 6, 9 Cucurbitane glycosides are the main components, and also and 13 are tasteless due to their failure to meet the the active ingredients of S. grosvenorii fruit. Ever since above-mentioned basic structural requirements. Glycosides of Takemoto et al. isolated mogrosides IV, V, and VI from S. the 11α-hydroxy compounds taste sweet, such as compounds grosvenorii fruit in 1983 [6-8], more than thirty similar 10, 11, 14 and 15, while glycosides in the 11β-hydroxy series compounds have been obtained from the fruit [9-13]. are tasteless, and the 11-oxo compounds, as well as the dehy- These compounds share the mogrolaglycone structure, dro derivatives, taste bitter. The relationship between the [10α-cucurbit-5-ene-3β, 11α, 24(R), 25-tetraol], with two to allocation of glucosyl units and sweetness is also noteworthy. six glucose units attached (see Fig. 2). Most of them taste SiamenosideI (16), which has four glucosyl units, is the sweet, so they are collectively called mogrosides, and are the sweetest compound among the glycosides of this type so far main active components of S. grosvenorii fruit. Mogrosides isolated, and showed a similar sweetness to mogrosideV (14) [14] are present at 1.19% in the fresh fruit , and 3.82% in the which has five glucosyl units, while mogroside IVA (10) [15] dried fruit of S. grosvenorii . Mogroside V is the main and IVE (11), with the same number of glucosyl units as 16, is component, with a content of 0.5%−1.4% in the dried fruit of less sweet than 16. Additionally, hydroxylation of the side S. grosvenorii. Siamenoside I is the sweetest among the cu- chain also affects the taste. For example, the bitter 11-oxo curbitane glycosides so far isolated [16-17]. The sweetness glycoside became sweet on hydroxylation of the side chain values of mogroside V and siamenoside I at the concentration double bond with osmium tetroxide. R1 R2 R3 R4 R5 R1 R2 R3 R4 R5 1 H H H α-OH H2 16 glc H α-OH H2 2 H glc H α-OH H2 H H 17 α-OH 2 3 glc H H α-OH H2 18 H α-OH H2 4 H H α-OH H2 19 glc H α-OH H2 5 H H α-OH H2 20 H H H =O H2 6 glc glc H α-OH H2 21 H glc H =O H2 – 90 – LI Chun, et al. / Chin J Nat Med, 2014, 12(2): 89−102 7 H H α-OH H2 22 glc H H =O H2 8 glc H α-OH H2 23 H H =O H2 9 glc H α-OH H2 24 glc glc H =O H2 10 H α-OH H2 25 glc H =O H2 11 H α-OH H2 26 H =O H2 12 glc H glc α-OH H2 27 H =O H2 13 glc H α-OH H2 28 glc glc H α-OH =O 14 H α-OH H2 29 H α-OH =O 15 H H 30 glc H H H α-OH 2 2 2 Fig. 2 Structures of thetriterpenoid compounds isolated from S. grosvenorii – 91 – LI Chun, et al. / Chin J Nat Med, 2014, 12(2): 89−102 Table 1 Triterpenoid compounds isolated from S. grosvenorii No. Compound name Plant parts References 1 Mogrol Fruit [6-9] 2 Mogroside IA (MogrosideIA1) Fruit [8-9] 3 Mogroside IE1 Fruit [8-9] 4 Mogroside IIA1 Fruit [8, 10] 5 Mogroside IIA2 Hydrolysis product [8] 6 Mogroside IIE Fruit [8-9, 11, 17-19] 7 Mogroside IIIA1 Fruit [8, 12] 8 Mogroside IIIA2 Fruit [8, 10] 9 Mogroside IIIE Fruit [8, 17] 10 Mogroside IVA Fruit [8-9, 19, 12-13] 11 Mogroside IVE Fruit [8-9, 12, 18] 12 Mogroside IIB Fruit [10] 13 Mogroside III Fruit [9, 17-19] 14 Mogroside V Fruit [8-9, 12-13, 17-18] 15 Mogroside VI Fruit [8] 16 Siamenoside I Fruit [9, 12, 17] 17 Neomogroside Fresh Fruit [18] 18 Isomogroside V Fruit [13] 19 Grosmomoside I Fruit [20] 20 11-Oxomogrol Hydrolysis product [9] 21 11-Oxomogroside IA1 Fruit [9, 19] 22 11-Oxomogroside IE1 Fruit [9] 23 11-Oxomogroside IIA1 Fruit [10] 24 11-Oxomogroside IIE Unripe fruit [19] 25 11-Oxomogroside III Unripe fruit [21] 26 11-Oxomogroside IVA Fruit [10, 21] 27 11-Oxomogroside V Fruit [9, 17] 28 7-Oxomogroside IIE Fruit [10] 29 7-Oxomogroside V Fruit [10] 30 11-DeoxymogrosideIII Fruit [10, 21] 31 20-Hydroxy-11-oxomogroside IA1 Unripe fruit [19] 32 5α, 6α-Epoxymogroside IE1 Fruit [9] 33 5-Dehydro-karounidiol dibenzoate Fruit [9] 34 Karounidiol dibenzoate Fruit [9] 35 Karounidiol 3-benzoate Fruit [9] 36 Isomultiflorenol Fruit [9] 37 β-Amyrin Fruit [9, 22] 38 10α-Cucurbitadienol Fruit [9] 39 Siratic acid A Root [23-24] 40 Siratic acid B Root [23-24] 41 Siratic acid C Root [23-24] 42 Siratic acid D Root [25] 43 Siratic acid E Root [18] 44 Siraitic acid F Root [26] 45 Mogroester Fruit [27-28] 46 Siraitic acid IIA Root [29] 47 Siraitic acid IIB Root [29] – 92 – LI Chun, et al.
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