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Chemical Constituents of Plants from the Genus Patrinia

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Chemical Constituents of Plants from the Genus Patrinia Natural Product Sciences 19(2) : 77-119 (2013) Chemical Constituents of Plants from the Genus Patrinia Ju Sun Kim and Sam Sik Kang* Natural Products Research Institute and College of Pharmacy, Seoul National University, Seoul 151-742, Korea Abstract − The genus Patrinia, belonging to the Valerianaceae family, includes ca. 20 species of herbaceous plants with yellow or white flowers, distributed in Korea, China, Siberia, and Japan. Among them, P. scabiosaefolia (yellow Patrinia), P. saniculaefolia, P. villosa (white Patrinia), and P. rupestris are found in Korea. Several members of this genus have long been used in folk medicine for the treatment of inflammation, wound healing, ascetics, and abdominal pain after childbirth. Thus far, ca. 217 constituents, namely flavonoids, iridoids, triterpenes, saponins, and others have been identified in this genus. Crude extract and isolated compounds have been found to exhibit anticancer, anti-inflammatory, antioxidant, antifungal, antibacterial, cytotoxic activities, lending support to the rationale behind several of its traditional uses. The present review compiles information concerning the phytochemistry and biological activities of Patrinia, with particular emphasis on P. villosa, as studied by our research group. Keywords − Valerianaceae, Patrinia species, Natural products chemistry, Biological activities Introduction of the compounds/extracts obtained from this plants. Patrinia is a genus of herbaceous plants in the Chemical Constituents Valerianaceae family. There are about 20 species native to grassy mountain habitats in China, Siberia, and Japan. The reported chemical constituents from the genus Among them, P. scabiosaefolia (yellow Patrinia), P. Patrinia number, thus far, approximtely 217, include saniculaefolia, P. villosa (white Patrinia), and P. rupestris flavonoids, iridoids, triterpenes, saponins, steroids, and a are found in Korea (Lee, 1989; Bae, 2000). In China, this few other compounds. Their structures are shown below, genus appears chiefly in the provinces of Sichuan, and their names and corresponding plant sources are Jiangxi, and Fujian. These are unassuming clump-forming compiled in Table 1. Of these, saponins are the most perennial plants having thin, erect stems with few leaves predominant constituents within the genus Patrinia. and bearing a terminal inflorescence with yellow or white 1. Flavonoids. Thirty-four flavonoids in total have been flowers. Whole plants (Herba Patriniae) are collected in isolated from the genus Patrinia. A dozen well-known autumn, dried in the shade, and cut into segments for use compounds (1 − 12) were also isolated from various (Wu, 2005). These plants have traditionally been used for Patrinia plants (Gu et al., 2002a, 2002b, 2002c; Peng et the treatment of initial stages of edema, appendicitis, al., 2006a, 2006b, 2006c; Larchenko et al., 1979; Greger endometriosis and inflammation (An et al., 2003; Chiu et and Ernet, 1971; Li et al., 2008; Huang et al., 2007; Cao, al., 2006)). Extensive studies of the chemical components 2006; Kim, 1997). A series of prenylated flavanone of Patrinia have led to the identification of compounds derivatives (22 − 28) and related chalcone and isoflavanone 1 − 217, including essential oils, iridoids, sesquiterpenes, derivatives (29 and 30, 31) were isolated from P. villosa triterpenes, saponins, flavonoids, coumarins, and lignans. (Peng et al., 2005a; 2006a; 2006d; 2006e; 2006f; 2006g; In this review article, we summarize the phytochemical 2006h). However, only one simple flavanone, 5,7,3',4'- works and list all of the compounds isolated from the tetrahydroxyflavanone (21), was isolated from P. rupestris genus Patrinia. Also included are the biological activities (Yang et al., 2007). The presence of the unusual prenylated flavanones with a 2',6'-dihydroxy substituted B-ring (22 − *Author for correspondence 28) was only noted in P. villosa (Peng et al., 2005a; Natural Products Research Institute and College of Pharmacy, Seoul 2006a; 2006d; 2006e; 2006f; 2006g; 2006h). Two National University, Seoul 151-742, Korea Tel: +82-2-880-2481; E-mail: [email protected] somewhat rare flavonol trisaccharide chains, rhamninose 77 78 Natural Product Sciences Table 1. Chemical constituents from the genus Patrinia No. Name Species Ref. 1 5,7-dihydroxyflavone P. scabra Gu et al., 2002a 2 apigenin P. v illosa Peng et al., 2006a 3 luteolin P. v illosa Peng et al., 2006a,b,c 4 5-hydroxy-7,4'-dimethoxyflavone P. v illosa Peng et al., 2006b,c 5 5-hydroxy-7,3',4'-trimethoxyflavone P. v illosa Peng et al., 2006b,c 6 3'-prenylapigenin P. v illosa Peng et al., 2006a 7 kaempferol P. intermedia Larchenko et al., 1979 P. rupestris Larchenko et al., 1979 P. scabiosaefolia Larchenko et al., 1979; Greger & Ernet, 1971 P. scabra Gu et al., 2002a P. sibirica Larchenko et al., 1979 P. v illosa Greger & Ernet, 1971 8 quercetin P. intermedia Larchenko et al., 1979 P. rupestris Larchenko et al., 1979 P. scabiosaefolia Larchenko et al., 1979; Greger & Ernet, 1971 P. scabra Gu et al., 2002b,c P. sibirica Larchenko et al., 1979 P. v illosa Peng et al., 2006a,c; Greger & Ernet, 1971; Li et al., 2008 9 kaempferol 3-O-β-D-glucoside P. v illosa Huang et al., 2007 10 kaempferol 3-O-β-D-glucoside 7-O-α-L-rhamnoside P. v illosa Huang et al., 2007 11 hyperin P. scabra Cao, 2006 12 rutin P. intermedia Larchenko et al., 1979 P. rupestris Larchenko et al., 1979 P. scabiosaefolia Larchenko et al., 1979; Kim, 1997 P. sibirica Larchenko et al., 1979 P. v illosa Li et al., 2008 13 kaempferol 3-O-rhamninoside P. v illosa Inada et al., 1993; Lee et al., 2013 14 kaempferol 3-O-4"'-acetylrhamninoside P. v illosa Lee et al., 2013 15 catharticin P. v illosa Lee et al., 2013 16 patriviloside 1 P. v illosa Lee et al., 2013 17 patriviloside 2 P. v illosa Lee et al., 2013 18 flavovilloside P. v illosa Inada et al., 1993 19 rhamnocitrin 3-O-isorhamninoside P. he te rophy lla Lu et al., 2007 20 rhamnetin 3-O-isorhamninoside P. he te rophy lla Lu et al., 2007 21 5,7,3',4'-tetrahydroxyflavanone P. rupestris Yang et al., 2007 22 (2S)-5,7,2',6'-tetrahydroxy-6,8-di(γ,γ-dimethylallyl)flavanone P. v illosa Peng et al., 2006a,d,e; Peng et al., 2005a 23 (2S)-5,7,2',6'-tetrahydroxy-6-lavandulylflavanone P. villosa Peng et al., 2006a,d,e,f 24 (2S)-5,7,2',6'-tetrahydroxy-4'-lavandulylflavanone P. v illosa Peng et al., 2006e 25 villosin A P. v illosa Peng et al., 2006e,f,g 26 villosin B P. v illosa Peng et al., 2006e,g Vol. 19, No. 2, 2013 79 Table 1. continued No. Name Species Ref. 27 orotinin P. v illosa Peng et al., 2006a,f,h 28 orotinin 5-methyl ether P. v illosa Peng et al., 2006f,h 29 licoagrochalcone B P. v illosa Peng et al., 2006e,h 30 bolusanthol B P. v illosa Peng et al., 2005a; Peng et al.,2006a,f 31 tetrapterol I P. v illosa Peng et al., 2005a 32 isoorientin P. v illosa Peng et al., 2005b; Peng et al., 2006c 33 isovitexin P. v illosa Peng et al., 2005b; Peng et al., 2006c 34 8-C-glucosylprunetin P. villosa Peng et al., 2006c 35 loganin P. v illosa Lee et al., 2013; Taguchi et al., 1973 36 loganic acid P. scabra Di et al., 2011 P. villosa Lee et al., 2013 37 villoside P. v illosa Taguchi et al., 1973 38 (7α-OH)-morroniside P. scabra Li et al., 2012 P. villosa Taguchi et al., 1973 39 villosol P. rupestris Yang et al., 2006a P. scabra Ma et al., 2012 P. v illosa Li et al., 2008; Xu et al., 1985 40 villosolside P. v illosa Xu et al., 1985; Lu et al., 1997 41 patrinalloside P. v illosa Huang et al., 2007 42 patrinoside P. gibbosa Uesato et al., 1987; Takeda & Aburada, 1980 P. scabiosaefolia Takeda & Aburada, 1980; Taguchi et al., 1979; Taguchi & Endo, 1974 P. triloba Takeda & Aburada, 1980 P. triloba var. Takeda & Aburada, 1980 palmate P. triloba var. Takeda & Aburada, 1980 kozushimensis P. triloba var. Takeda & Aburada, 1980 takeuchiana P. triloba var. Taguchi et al., 1979 triloba 43 patriscadoid I P. scabiosaefolia Choi et al., 2009a 44 patriscadoid II P. scabiosaefolia Choi et al., 2009a 45 sweroside P. scabra Li et al., 2012 46 patriscabrol P. rupestris Yang et al., 2006a P. scabra Li et al., 2012; Ma et al., 2012; Kouno et al., 1994 47 isopatriscabrol P. scabra Li et al., 2012; Kouno et al., 1994 48 patriscabroside I P. scabra Li et al., 2012; Kouno et al., 1994 49 isopatriscabroside I P. scabra Di et al., 2011; Kouno et al., 1994 50 patriscabroside II P. rupestris Yang et al., 2006a P. scabra Kouno et al., 1994 51 isopatriscabroside II P. scabra Kouno et al., 1994 52 patriscabroside III P. scabra Kouno et al., 1994 53 patrinioside P. scabra Li et al., 2012; Kouno et al., 1995 3-methylbutyric acid 7-hydroxy-7-hydroxymethyl- 54 4-(3-methyl-butyryloxymethyl)-6-oxo-1,6,7,7a- P. scabra Yang et al., 2004 tetrahydrocyclopenta[c]pyran-1-yl ester 80 Natural Product Sciences Table 1. continued No. Name Species Ref. 55 6-hydroxy-7-methylhexahydrocyclopenta[c]pyran-3-one P. scabra Yang et al., 2004 1,3-dimethyloxy-7-hydroxymethyl-4-(3-methyl- 56 P. scabra Liu et al., 2006 butyryloxymethyl)-1-hydrocyclopenta-4,7-diene[c]pyran-6-one 1,3-dimethyloxy-7-hydroxymethyl-4-methyloxymethyl-1- 57 P. scabra Liu et al., 2006 hydrocyclopenta-4,7-diene[c]pyran-6-one 58 scabroside A P. scabra Di et al., 2011 59 scabroside B P. scabra Di et al., 2011 60 scabroside C P. scabra Di et al., 2011 61 jatamanin J P. scabra Di et al., 2011 62 patriridoside D P.
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