Fig. 1.1
Ripen fruits of L. ruthenicum (a), L. barbarum (b), and L. chinense (c)
Table 1.1
Morphological differences and geographic distribution of L. chinense, L. barbarum, L. ruthenicum
Species | Morphological identity | Geographic distribution |
---|---|---|
L. chinense M | Leaf blade ovate, rhombic, lanceolate, or linear-lanceolate. Pedicel 1–2 cm. Calyx 3–5-divided to halfway, lobes densely ciliate. Corolla tube shorter than or subequaling lobes, lobes pubescent at margin. Stamens filaments villous slightly above base. Berry red, ovoid or oblong. Seeds numerous, yellow | In China: Anhui, Fujian, Gansu, Guangdong, Guangxi, Guizhou, Hainan, Hebei, Heilongjiang, Henan, Hubei, Hunan, Jiangsu, Jiangxi, Jilin, Liaoning, Nei Mongol, Ningxia, Qinghai, Shaanxi, Shanxi, Sichuan, Yunnan, Zhejiang. Taiwan, Japan, Korea, Mongolia, Nepal, Pakistan, Thailand, SW Asia, Europe |
L. barbarum L | Leaves lanceolate or long elliptic. Pedicel 1–2 cm. Calyx usually 2-lobed, lobes 2- or 3- toothed at apex. Corolla tube 8–10 mm, obviously longer than limb and lobes; lobes 5–6 mm, spreading, margin glabrescent. Berry red or orange-yellow, oblong or ovoid. Seeds usually 4–20, brown-yellow | In China: Ningxia, Gansu, Qinghai, Xinjiang |
L. ruthenicum M | Shrubs copiously armed. Leaves subsessile; leaf succulent, linear or subcylindric, rarely linear-oblanceolate. Pedicel 5–10 mm. Calyx irregularly 2–4-lobed, lobes sparsely ciliate. Corolla lobes oblong ovate, not ciliate. Stamens filaments sparsely villous above base. Fruiting calyx slightly inflated. Berry purple-black, globose, sometimes emarginate. Seeds brown | In China: Gansu, Nei Mongol, Ningxia, Qinghai, N Shaanxi, Xinjiang, Xizang. Afghanistan, Kazakhstan, Kyrgyzstan, Mongolia, Pakistan, Russia, Tajikistan, Turkmenistan, Uzbekistan, SW Asia, Europe |
1.4 Chemical Diversity in Leaf and Fruits of Wolfberry
Polysaccharides represent quantitatively the most important group of substances in the fruit of L. barbarum. which are estimated to comprise 3–8 % of the dried fruits (Amagase and Farnswoeth 2011). More than 30 polysaccarides have been isolated from the fruit of L. barbarum, L. chinense, and L. ruthenium (Table 1.2). The molecular weight of polysaccharides varies greatly in different species, which might lead to the different pharmacological function.
Table 1.2
Polysaccharides in fruits of L. chinense, L. barbarum, L. ruthenicum
Glycoconjugate | MW | Carbohydrate content | Monosaccharides (molar ratio or %) | Reference |
---|---|---|---|---|
L. barbarum | ||||
LbGp1 | 88,000 | Ara, Gla, Glc (2.5:1.0:1.0) | (Yao et al. 2011) | |
LbGp2 | 68,200 | 90.7 | Ara, Gal (4:5) | (Peng and Tian 2001) |
LbGp3 | 92,500 | 93.6 | Ara, Gal (1:1) | |
LbGp4 | 214,800 | 85.6 | Ara, Gal, Rha, Glc (1.5:2.5:0.43:0.23) | |
LbGp5 | 23,700 | 8.6 | Rha, Ara, Xyl, Gal, Man, Glc (0.33:0.52:0.42:0.94:0.85:1) | (Huang et al. 1998) |
LbGp5B | 23,700 | Rha, Ara, Glc, Gal, (0.1:1:1.2:0.3), Galu (0.9) | (Peng et al. 2001b) | |
LBP3p | 157,000 | 92.4 | Gal, Glc, Rha, Ara, Man, Xyl (1:2.12:1.25:1.10:1.95:1.76) | (Gan et al. 2004) |
LBPC2 | 12,000 | 92.8 | Xyl, Rha, Man (8.8:2.3:1) | |
LBPC4 | 10,000 | 95 | Glc | |
LBPA1 | 18,000 | Heteroglycan | (Zhao et al. 1997) | |
LBPA3 | 66,000 | Ara, Gal (1.2:1) | (Zhao et al. 1997) | |
LBP1a-1 | 11,500 | Glc | (Duan et al. 2001) | |
LBP1a-2 | 9400 | Glc | (Duan et al. 2001) | |
LBP3a-1 | 10,300 | GalA | (Duan et al. 2001) | |
LBP3a-2 | 8200 | GalA | (Duan et al. 2001) | |
LBPF1 | 150,000 | 48.2 | (Chen et al. 2008) | |
LBPF2 | 150,000 | 30.5 | (Chen et al. 2008) | |
LBPF3 | 150,000 | 34.5 | (Chen et al. 2008) | |
LBPF4 | 150,000 | 20.3 | (Chen et al. 2008) | |
LBPF5 | 150,000 | 23.5 | (Chen et al. 2008) | |
LBPB1 | 18,000 | Ara, Glc (1:3.1) | ||
PLBP | 121,000 | (Liang et al. 2011) | ||
LBP-IV | 418,000 | Rha, Ara, xyl, glc, Gal (1.61:3.82:03.44:7.54:1.00) | (Liu et al. 2012) | |
L. chinense | ||||
Cp-1-A | 10,000 | 87.8 | Ara, Xyl (1:1) | (Qin et al. 2000) |
Cp-1-B | 11,000 | 89.4 | Ara | (Qin et al. 2000) |
Cp-1-C | 42,000 | 92.4 | Ara, Gal (3:1) | (Qin et al. 2000) |
Cp-1-D | 23,000 | 90.7 | Ara, Gal (1:1) | (Qin et al. 2000) |
Cp-2-A | 89,000 | 88.3 | Ara (50.6), Gal (22.8), Man (8.4), Rha (5.9), Glc (5.6) | (Qin et al. 2001) |
Cp-2-B | 89,000 | 88.3 | Ara (45.5), Gal (47.4) | (Qin et al. 2001) |
Hp-2-A | 8000 | 87.9 | Ara (70.6), Gal (13.5) | (Qin et al. 2001) |
Hp-2-B | 11,000 | 89.9 | Ara (84.2), Gal (10.7) | (Qin et al. 2001) |
Hp-2-C | 120,000 | 90.7 | Ara (49.5), Gal (40.8), Fuc (5.9) | (Qin et al. 2001) |
Hp-0-A | 23,000 | Ara | (Potterat 2010) | |
L. ruthenicum | ||||
LRGP1 | 56,200 | Rha, Ara, xyl, Man, glc, Gal (0.65:10.71:0.33:0.67:1:10.41) | (Peng et al. 2012a) | |
LRP4-A | 105,000 | Rha, Ara, glc, Gal (1:7.6:0.5:8.6) | (Lv et al. 2013) | |
LRGP3 | 75,600 | Rha, Ara, Gal (1.0:14.9:10.4) | (Peng et al. 2012b) |
As to the color regents in wolfberry, the reddish-orange color of L. barbarum and L. chinense is derived from carotenoids and their esters, which are the second major group of metabolites. Twelve carotenoids and their esters were identified in the genus Lycium (Table 1.2.). The highest content of carotenoids in ripen red berry is zeaxanthin dipalmitate which counts for 75 % of total carotenoids (508.90 μg g− 1 fresh weight (FW) in ripen fresh fruit) (Liu et al. 2014). Although there is very low level of total carotenoid (34.46 μg g− 1 FW), with 18.01μg g− 1 FW of β-carotene, in green fruits of L. ruthenicum, the content of total carotenoid in ripen black berry is undetectable (Liu et al. 2014). The zeaxanthin and β-Cryptoxanthin are undetectable both in green and ripen fruits of L. ruthenicum (Liu et al. 2014). As to the black color in ripen fruits of L. ruthenicum, ten anthocyanins were identified using HPLC-DAD-MS/MS (Zheng et al. 2011), with the highest content of pentunidin-3-O-rutinoside (trans-p-coumaroyl)-5-O-glucoside which counts 95 % of total flavonoids (Zeng et al. 2014). Consistent with this, anthocyanin content in L. ruthenicum increased steadily and reached maximum levels (10.37 OD534/g) at the ripening stage, while anthocyanin was undetectable at all stages in L. barbarum fruits (Zeng et al. 2014).
Other phytochemicals include flavonoids, alkaloids, amides, peptides, anthraquinones, coumarins, lignanoids, terpenoids, steroids, and their derivatives, organic acids, and glycolipids are summarized in Table 1.3. Kim et al. (1997c) identified 45 volatile flavor components in L. chinense leaves including four acids, 15 alcohols, seven aldehydes, two esters, three furans, nine hydrocarbons, and three others. Sannai et al. (1983) identified 36 neutral volatile compounds in L. chinense fruits. Fifty-four volatile components including twelve alcohols, twelve esters, seven aldehydes, six acids, five hydrocarbons, eight ketones, one furan, and three pyrazines were detected in the fruit of L. chinense (Yao et al. 2011). Twenty-one compounds from the essential oil of L. barbarum fruits and 18 compounds from the essential oil of L. ruthenicum fruits were identified by GC/MS (Altintas et al. 2006). 1β-Amino-3β, 4β, 5α-trihydroxycycloheptane, digupigan A, and a tryptophane glycoside, were only isolated from the root barks of L. chinense (Asano et al. 1997; Yahara et al. 1989; Wei and Liang 2003). The only one lignin, (+)-Lyoniresinol 3α–O–β–d-glucopyranoside was isolated from the root bark of L. chinense (Han et al. 2002; Lee et al. 2005). Two compounds were newly identified from the acetone extract of dry Goji berry, 3-(3-hydroxy-4-methoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]-(2E)-Propenamide, and 3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-2-Propenamide (Personal communication with Dr. Minghua Qiu).
Table 1.3
Chemical constituents of L. barbarum, L. chinense, and L. ruthenicum
Compound name | L. barbarum | L. chinense | L. ruthenicum |
---|---|---|---|
Carotenoids and their esters | |||
β-Carotene | Fruit (Yao et al. 2011) | Fruit/leaf (Yao et al. 2011) | |
Zeaxanthin | Fruit (Yao et al. 2011) | Fruit (Yao et al. 2011) | |
β-Cryptoxanthin | Fruit (Yao et al. 2011) | Fruit (Yao et al. 2011) | |
Zeaxanthinmonopalmitate | Fruit (Yao et al. 2011) | Fruit (Yao et al. 2011) | |
Zeaxanthindipalmitate | Fruit (Yao et al. 2011) | Fruit (Kim et al. 1997b) | |
Zeaxanthinmonomyristate | Fruit (Yao et al. 2011) | ||
Zeaxanthinmyristate/palmitate | Fruit (Yao et al. 2011) | ||
β-Cryptoxanthinpalmitate | Fruit (Yao et al. 2011) | ||
Violaxanthindipalmitate | Fruit (Yao et al. 2011) | ||
Mutatoxanthindipalmitate | Fruit (Yao et al. 2011) | ||
Antheraxanthindipalmitate | Fruit (Yao et al. 2011) | ||
Lutein | Fruit/ leaf (Yao et al. 2011) | ||
Flavonoids | |||
Quercetin | Fruit/ leaf/flower (Yao et al. 2011) | Fruit/leaf (Miean and Mohamed 2001) | |
Kaempferol | Fruit/ leaf/flower (Yao et al. 2011) | ||
Myricetin | Fruit (Le et al. 2007) | ||
Rutin | Fruit/leaf (Yao et al. 2011) | Fruit/leaf/root (Yao et al. 2011) | |
Isorhamnetin 3-O-rutinoside | Fruit (Inbaraj et al. 2010) | ||
Kaempferol-3-O-rutinoside | Fruit (Inbaraj et al. 2010) | ||
Hesperidin | Fruit (Inbaraj et al. 2010) | ||
Apigenin | Leaf/root bark (Miean and Mohamed 2001) | ||
Luteolin | Leaf (Zou 2002) | ||
Acacetin | Leaf (Zou 2002) | ||
3, 5, 7, 3′-Tetrahydroxy-6, 4′, 5′-trimethoxyflavone | Leaf (Zou 2002) | ||
Morin | Fruit (Qian et al. 2004) | ||
Acatein 7-O-rhamnosyl-(1-6)-glucopyranoside | Leaf (Zou 2002) | ||
Quercetin 3-O-sophoroside | Leaf (Yao et al. 2011) | ||
Quercetin 7-O-glucoside 3-O-glucosyl-(1-2)-galactopyranoside | Leaf (Yao et al. 2011) | ||
Kaempferol 3-O-sophoroside | Leaf (Yao et al. 2011) | ||
Kaempferol 7-O-glucoside 3-O-glucosyl-(1-2)-galactoside | Leaf (Yao et al. 2011) | ||
Linarin | |||
Alkaloids | |||
Atropine | |||
Hyoscyamine | Fruit/ shoot/root (Harsh 1989) | ||
N a -[(E)-Cinnamoyl]histamine | Leaf (Yao et al. 2011) | ||
Betaine | Fruit/ leaf/ root bark (Yao et al. 2011) | ||
Melatonin | Fruit (Yao et al. 2011) | ||
Calystegine A3 | Root bark (Asano et al. 1997) | ||
Calystegine A5 | Root bark (Asano et al. 1997) | ||
Calystegine A6 | Root bark (Asano et al. 1997) | ||
Calystegine A7 | Root bark (Asano et al. 1997) | ||
Calystegine B1 | Root bark (Asano et al. 1997) | ||
Calystegine B2 | Root bark (Asano et al. 1997) | ||
Calystegine B3 | Root bark (Asano et al. 1997) | ||
Calystegine B4 | Root bark (Asano et al. 1997) | ||
Calystegine B5 | Root bark (Asano et al. 1997) | ||
Calystegine C1 | Root bark (Asano et al. 1997) | ||
Calystegine C2 | Root bark (Asano et al. 1997) | ||
Calystegine N1 | Root bark (Asano et al. 1997) | ||
N-Methylcalystegine B2 | Root bark (Asano et al. 1997) | ||
N-Methylcalystegine C1 | Root bark (Asano et al. 1997) | ||
Fagomine | Root bark (Asano et al. 1997) | ||
6-Deoxyfagomine | Root bark (Asano et al. 1997) | ||
4-[2-Formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] butanoic acid | Fruit (Chin et al. 2003) | ||
4-[2-Formyl-5-(methoxymethyl)-1H-pyrrol-1-yl] butanoic acid | Fruit (Chin et al. 2003) | ||
4-[2-Formyl-5-(methoxymethyl)-1H-pyrrol-1-yl] butanoate | Fruit (Chin et al. 2003) | ||
Alkaloid I | Root bark (Yao et al. 2011) | ||
Alkaloid I | Root bark (Yao et al. 2011) | ||
Kukoamine A | Root bark (Funayama et al. 1980) | ||
Kukoamine B | Root bark (Yao et al. 2011) | ||
Betaine | Fruit/ leaf/root bark/ root (Yao et al. 2011) | ||
Betaine hydrochloride | Root bark (Zhou et al. 1996) | ||
Choline | Root/ root bark (Yao et al. 2011) | ||
9-Formylharman | Fruit (Han et al. 1985) | ||
1-(Methoxycarbonyl)-β-carboline | Fruit (Han et al. 1985) | ||
Perlolyrine | Fruit (Han et al. 1985) | ||
Amides | |||
Lyciumide A | Fruit (Yao et al. 2011) | ||
3-(3-Hydroxy-4-methoxyphenyl)-N-[2-(4- methoxyphenyl) ethyl]-(2E)-Propenamide | Fruit (Personal communication with Dr. Minghua Qiu) | ||
3-(4-Hydroxy-3-methoxyphenyl)-N-[2-(4- hydroxyphenyl) ethyl]-2-Propenamide | Fruit (Personal communication with Dr. Minghua Qiu) | ||
N-(α,β-Dihydrocaffeoyl)tyramine | |||
N-[(E)-Caffeoyl]tyramine | |||
N-[(Z)-Caffeoyl]tyramine | |||
N-[(E)-Feruloyl]octopamine | Root bark (Lee et al. 2004) | ||
(2S, 3R, 4E, 8Z)-1-O-(β–d -Glucopyranosyl)-2-(palmitoylamino)octadecasphinga-4,8-diene | |||
(2S, 3R, 4E, 8Z)-1-O-(β–d -Glucopyranosyl)-2-[(2-hydroxypalmitoyl)amino]sphinga-4,8-diene | |||
Peptides | |||
Lyciumamide | Stem/root bark (Noguchi et al. 1984) | ||
Lyciumins A | Root bark (Yahara et al. 1989) | ||
Lyciumins B | Root bark (Yahara et al. 1989) | ||
Lyciumins C | Root bark (Yahara et al. 1993) | ||
Lyciumins D | Root bark (Yahara et al. 1993) | ||
Anthraquinones | |||
Emodin | Root bark (Wei and Liang 2002) | ||
Physcion | Root bark (Wei and Liang 2002) | ||
1, 3, 6-Trihydroxy-2-methyl-9, 10-anthraqui-none | Root bark (Yao et al. 2011) | ||
1, 3, 6-Trihydroxy-2-methyl-9, 10-anthraquinone 3-O-(rhamnopyranosyl)-(1-2)-6′-acetylglucopyranoside | Root bark (Yao et al. 2011) | ||
Coumarins | |||
Scopoletin | Fruit/leaf (Yao et al. 2011) | ||
Scopoletin | |||
Scopolin | Root bark (Wei and Liang 2002)
Stay updated, free articles. Join our Telegram channelFull access? Get Clinical TreeGet Clinical Tree app for offline access |