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. 2017 Apr 24;40(6):655–675. doi: 10.1007/s12272-017-0892-3

Table 3.

Constituents from A. keiskei and their reported biological activities

Compound class/name Parta Biological activity Reference(s)
Flavonoids
Chalcones
 Xanthoangelol F (2) RT First isolation from the part Nakata et al. (1999)
RT Anti-hypertensive activity: phenylephrine-induced vasoconstriction in rat aortic rings Matsuura et al. (2001)
EXD

Anti-tumor-promoter activity: EBV-EA by TPA

Anti-tumor-initiator activity: NOR 1

Akihisa et al. (2003)
EXD Anti-inflammatory activity (details in the patent) Akihisa et al. (2007)
ST Cytotoxicities: human neuroblastoma (IMR-32, NB-39) Nishimura et al. (2007)
Syn Anti-bacterial activity: Gram-positive bacteria Sugamoto et al. (2011)
AP Anti-viral activity: influenza virus neuraminidase Park et al. (2011)
WP Anti-viral activity: SARS-CoV (3CLpro, PLpro) Park et al. (2015)
WP Anti-oxidative activity: XO Kim et al. (2014)
ST Anti-diabetic activity: PTP1B Li et al. (2015)
 Isobavachalcone (4) RT First isolation from the part Nakata et al. (1999)
EXD Anti-tumor-promoter activity: EBV-EA by TPA, in vivo Akihisa et al. (2003)

Two-stage mouse skin carcinogenesis test

Anti-tumor-initiator activity: NOR 1

Akihisa et al. (2006)
ST Anti-tumor activity: apoptosis (procaspase-3, -9, Bax) in human neuroblastoma cells (IMR-32, NB-39) Nishimura et al. (2007)
EXD Anti-inflammatory activity (details in the patent) Akihisa et al. (2007)
Com Anti-inflammatory activity: iNOS Shin et al. (2013)
Syn Anti-bacterial activity: Gram-positive bacteria Sugamoto et al. (2011)
AP Anti-oxidative activity: NQO1 induction, DPPH radical scavenging Luo et al. (2012)
WP Anti-oxidative activity: XO Kim et al. (2014)
AP Anti-diabetic activity: α-glucosidase Luo et al. (2012)
WP Anti-viral activity: SARS-CoV (3CLpro, PLpro) Park et al. (2015)
 Xanthoangelol B (5) RT First isolation from the part Baba et al. (1990b)
RT Anti-hypertensive activity: phenylephrine-induced vasoconstriction in rat aortic rings Matsuura et al. (2001)
RT Anti-allergic activity: compound 48/80-induced histamine release Nakata and Baba (2001)
ST Anti-oxidative activity: superoxide-scavenging Aoki et al. (2008)
WP Anti-oxidative activity: XO Kim et al. (2014)
LF Anti-inflammatory activity: IL-6 in TNF-α-stimulated osteosarcoma cells Shin et al. (2011)
AP Anti-inflammatory activity: NO, iNOS, COX-2 (IκB degradation, NF-κB nuclear translocation) Chang et al. (2014)
AP Anti-viral activity: influenza virus neuraminidase Park et al. (2011)
ST Anti-thrombotic activity: TNFα-induced PAI-1 Ohkura et al. (2011)
WP Anti-viral activity: SARS-CoV (3CLpro, PLpro) Park et al. (2015)
 Xanthoangelol G (6) RT First isolation from the part Nakata et al. (1999)
AP Anti-viral activity: influenza virus neuraminidase Park et al. (2011)
WP Anti-viral activity: SARS-CoV (3CLpro, PLpro) Park et al. (2015)
 4,2′-Dihydroxy-3′-[(2E)-6-hydroperoxy-3-methyl-7-methylene-2-octenyl]-4′-methoxy chalcone (7) RT Preventive effect against metabolic syndrome: adiponectin production Ohnogi et al. (2012b)
 Xanthoangelol C (8) RT Baba et al. (1990b)
RT Anti-allergic activity: compound 48/80-induced histamine Nakata and Baba (2001)
 Xanthoangelol D (9) RT First isolation from the part Baba et al. (1990b)
RT Anti-inflammatory activity: TNF-α induced ET-1 (NF-κB) Sugii et al. (2005)
AP Anti-viral activity: influenza virus neuraminidase Park et al. (2011)
ST Anti-thrombotic activity: TNFα-induced PAI-1 Ohkura et al. (2011)
WP Anti-viral activity: SARS-CoV (3CLpro, PLpro) Park et al. (2015)
ST Anti-diabetic activity: PTP1B Li et al. (2015)
 Xanthoangelol E (10) RT First isolation from the part Baba et al. (1990b)
RT Anti-ulcer activity (details in the patent) Murakami et al. (1992)
RT Anti-thrombotic activity: arachidonic acid metabolism in platelets Fujita et al. (1992)
RT Anti-hypertensive activity: phenylephrine-induced vasoconstriction in rat aortic rings Matsuura et al. (2001)
RT Anti-allergic activity: compound 48/80-induced histamine Nakata and Baba (2001)
LF First isolation from the part Shin et al. (2011)
AP Anti-inflammatory activity: NO, iNOS, COX-2 (IκB degradation, NF-κB nuclear translocation) Chang et al. (2014)
WP Anti-viral activity: SARS-CoV (3CLpro, PLpro) Park et al. (2015)
ST Anti-diabetic activity: PTP1B Li et al. (2015)
 Ashitaba-chalcone (11) RT Anti-tumor-promoter activity: TPA-stimulated 32Pi-incorporation Okuyama et al. (1991)
 Xanthoangelol H (12) RT First isolation from the part Nakata et al. (1999)
EXD Anti-tumor-promoter activity: EBV-EA by TPA Akihisa et al. (2003)
ST Cytotoxicities: human neuroblastoma (IMR-32, NB-39) Nishimura et al. (2007)
ST Whitening activity: melanin formation in melanoma cells Arung et al. (2012)
 Deoxyxanthoangelol H (13) EXD First isolation from the part Akihisa et al. (2006)
EXD Anti-inflammatory activity (details in the patent) Akihisa et al. (2007)
ST Whitening activity: melanin formation in melanoma cells Arung et al. (2012)
 Xanthoangelol I (14) EXD

Anti-tumor-promoter activity: EBV-EA by TPA

Anti-tumor-initiator activity: NOR 1

Akihisa et al. (2006)
ST Cytotoxicities: human neuroblastoma (IMR-32, NB-39) Nishimura et al. (2007)
 2″-Hydroxy-xanthoangelol I (15) RT Protective effect on nerve cells (details in the patent) Onogi et al. (2004)
RT Preventive effect against metabolic syndrome: adiponectin Ohnogi et al. (2012b)
 Xanthoangelol J (16) EXD Anti-tumor-promoter activity: EBV-EA by TPA Akihisa et al. (2006)
Anti-tumor-initiator activity: NOR 1
 Xanthoangelol K (17) ST Anti-diabetic activity: PTP1B Li et al. (2015)
 Xanthoangelol L (18) ST First isolation from the part Li et al. (2015)
 Jejuchalcone D (19) ST First isolation from the part Li et al. (2015)
 Xanthoangelol M (20) ST Anti-diabetic activity: PTP1B Li et al. (2015)
 4-Hydroxy-2′,3′-(2,3-dihydro-2-hydroxy isopropylfurano)-4′-methoxychalcone (21) RT Preventive effect against metabolic syndrome: adiponectin production Ohnogi et al. (2012b)
 Jejuchalcone E (22) ST First isolation from the part Li et al. (2015)
 Dorsmannin A (23) EXD First isolation from the part Akihisa et al. (2006)
 Xanthokeismin A (24) ST Anti-oxidative activity: superoxide-scavenging Aoki et al. (2008)
AP Anti-inflammatory activity: NO, iNOS, COX-2 (IκB degradation, NF-κB nuclear translocation) Chang et al. (2014)
 Xanthokeismin B (25) ST Anti-oxidative activity: superoxide-scavenging Aoki et al. (2008)
 Xanthokeismin C (26) ST Anti-oxidative activity: superoxide-scavenging Aoki et al. (2008)
 4,2′,4′-Trihydroxy-3′-[(6E)-2-hydroxy-7-methyl-3-methylene-6-octenyl]chalcone (27)

LF

AP

Anti-inflammatory activity: IL-6 in TNF-α-stimulated osteosarcoma cells

Protective activity on damaged normal cells: HSPs

Shin et al. (2011)

Kil et al. (2015a)

 Xanthokeistal A (28)

AP

WP

Anti-viral activity: influenza virus neuraminidase

Anti-viral activity: SARS-CoV (3CLpro, PLpro)

Park et al. (2011)

Park et al. (2015)

 4,2′4′-Trihydroxy-3′-[(2E)-6,7-dihydroxy-3,7-dimethyl-2-octenyl] chalcone (29)

RT

AP

First isolation from the part

First isolation from the part

Ohnogi et al. (2012b)

Luo et al. (2012)

 4,2′-Dihydroxy-3′,4′-{2,3-dihydro-2-[(4E)-1-hydroxy-1,5-dimethyl-4-hexenyl]furano}

chalcone (30)

RT Preventive effect against metabolic syndrome: adiponectin production Ohnogi et al. (2012b)
 Angelichalcone (31)

RT

RT

Protective effect on nerve cells (details in the patent)

Osteogenesis promotive activity (details in the patent)

Onogi et al. (2004)

Ohnogi et al. (2004)

 4,2′,4′-Trihydroxy-3′-[(2E,5E)-7-methoxy-3,7-dimethyl-2,5-octadienyl] chalcone (32) AP First isolation from the part Kil et al. (2015a)
 (±)-4,2′,4′-Trihydroxy-3′-[(2E)-6-hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (33) AP First isolation from the part Kil et al. (2015a)
 4,2′,4′-Trihydroxy-3′-[(2E)-3-methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (34) AP First isolation from the part Kil et al. (2015a)
 2′,3′-Furano-4-hydroxy-4′-methoxychalcone (35) AP First isolation from the part Kil et al. (2015a)
 (±)-4-Hydroxy-2′,3′-(2,3-dihydro-2-methoxyfurano)-4′-methoxychalcone (36) AP First isolation from the part Kil et al. (2015a)
 3′-Carboxymethyl- 4,2′-dihydroxy-4′-methoxy chalcone (37) AP First isolation from the part Kil et al. (2016)
 (±)-4,2′,4′-Trihydroxy-3′-[(3-hydroxy-2,2-dimethyl-6-methylenecyclohexyl)methyl]chalcone (38) AP First isolation from the part Kil et al. (2016)
 2″-Hydroxy angelichalcone (39) AP First isolation from the part Kil et al. (2016)
 Artocarmitin A (40) AP First isolation from the part Kil et al. (2016)
 Dihydrochalcones
 Deoxydihydroxanthoan EXD First isolation from the part Akihisa et al. (2006)
 Gelol H (41) ST whitening activity: melanin formation in melanoma cells Arung et al. (2012)
 Erioschalcone A (42) AP First isolation from the part Luo et al. (2012)
Flavones
 Cynaroside (43) (=luteolin-7-O-β-d-glucopyranoside) AP Anti-hyperlipidemic acitivity Park et al. (1995)
AP Anti-cholesterogenic activity: HMG-CoA reductase Park et al. (1997b)
AP Anti-mutagenic activity (AFB1) Park et al. (1997a)
AP Anti-oxidative activity: epoxide hydrolase in liver Park et al. (2002)
AP Anti-oxidative activity: DPPH radical scavenging Kim et al. (2005)
AP Anti-depressant activity: DBH Kim et al. (2013)
ST Anti-diabetic activity: PTP1B Li et al. (2015)
 Luteolin-7-O-β-d-rutinoside (44) AP First isolation from the part Park et al. (1995)
AP Anti-mutagenic activity (AFB1) Park et al. (1997a)
AP Anti-oxidative activity: DPPH radical scavenging Kim et al. (2005)
  Luteolin (45) LF First isolation from the part Sugamoto et al. (2008)
Flavonol glycosides
 Kaempferol-3-O-α-d-arabinopyranoside (46) AP Anti-oxidative activity: DPPH radical scavenging Kim et al. (2005)
 Isoquercitrin (=quercetin-3-O-β-d-glucopyranoside) (47) AP Anti-oxidative activity: DPPH radical scavenging Kim et al. (2005)
 Hyperoside (=quercetin-3-O-β-d-galactopyranoside) (48) AP First isolation from the part Park et al. (1996)
AP Anti-cholesterogenic activity: HMG-CoA reductase Park et al. (1997b)
AP Anti-mutagenic activity (AFB1) Park et al. (1997a)
AP Anti-oxidative activity: DPPH radical scavenging Kim et al. (2005)
 Quercitrin (49) (=quercetin-3-O-β-d-rhamnopyranoside) LF First isolation from the part Sugamoto et al. (2008)
 Quercetin-3-O-α-d-arabinopyranoside (50) AP Anti-oxidative activity: DPPH radical scavenging Kim et al. (2005)
 Flavanones
 Munduleaflavanone A (51) EXD Anti-tumor-promoter activity: EBV-EA by TPA Akihisa et al. (2003)
AP Anti-diabetic activity: α-glucosidase Luo et al. (2012)
 Munduleaflavanone B (52) EXD Anti-tumor-promoter activity: EBV-EA by TPA Akihisa et al. (2006)
Anti-tumor-initiator activity: NOR 1
EXD anti-inflammatory activity: TPA-induced mouse ear edema Akihisa et al. (2007)
 Isobavachin (53) EXD Anti-tumor-promoter activity: EBV-EA by TPA Akihisa et al. (2006)
 Prostratol F (54) EXD Anti-tumor-promoter activity: EBV-EA by TPA Akihisa et al. (2003)
 Sophoraflavanone A (55) (=8-geranylnaringenin) EXD Anti-tumor-promoter activity: EBV-EA by TPA Akihisa et al. (2006)
Anti-tumor-initiator activity: NOR 1
EXD Anti-inflammatory activity: TPA-induced mouse ear edema Akihisa et al. (2007)
 4′-O-Geranylnaringenin (56) EXD Anti-tumor-promoter activity: EBV-EA by TPA Akihisa et al. (2003)
Coumarins
Umbelliferone (57) RT First isolation from the part Baba et al. (1990b)
Scopoletin (58) RT First isolation from the part Baba et al. (1990b)
Demethylsuberosin (59) AP Anti-diabetic activity: α-glucosidase Luo et al. (2012)
Osthenol (60) EXD Anti-tumor-promoter activity: EBV-EA by TPA Akihisa et al. (2006)
Anti-tumor-initiator activity: NOR 1
EXD Anti-inflammatory activity (details in the patent) Akihisa et al. (2007)
7-O-β-d-Glucopyranosyloxy-8-prenyl coumarin (61) RT NGF production enhancive effect on in mouse fibroblasts (details in the patent) Ohnogi et al. (2002)
Psoralen (62) RT First isolation from the part Hata and Kozawa (1961)
AP First isolation from the part Luo et al. (2012)
 Ergapten (63) RT First isolation from the part Hata and Kozawa (1961)
FR First isolation from the part Baba et al. (1990a)
AP First isolation from the part Luo et al. (2012)
ST Anti-diabetic activity: PTP1B Li et al. (2015)
Xanthotoxin (64) RT First isolation from the part Hata and Kozawa (1961)
FR First isolation from the part Baba et al. (1990a)
EXD First isolation from the part Akihisa et al. (2006)
AP First isolation from the part Luo et al. (2012)
Isopimpinellin (65) RT First isolation from the part Baba et al. (1990b)
FR First isolation from the part Nakata et al. (1997)
EXD First isolation from the part Akihisa et al. (2006)
Imperatorin (66) FR First isolation from the part Baba et al. (1990a)
RT First isolation from the part Nakata et al. (1997)
AP First isolation from the part Luo et al. (2012)
Isogosferol (67) FR First isolation from the part Baba et al. (1990a)
Isoimperatorin (68) FR First isolation from the part Baba et al. (1990a)
RT First isolation from the part Nakata et al. (1997)
Saxaline (69) FR First isolation from the part Nakata et al. (1997)
Marmesin (70) RT First isolation from the part Baba et al. (1990b)
(−)-Oxypeucedanin (71) FR First isolation from the part Baba et al. (1990a)
RT First isolation from the part Nakata et al. (1997)
(+)-Oxypeucedanin hydrate (72) FR, First isolation from the part Nakata et al. (1997)
RT First isolation from the part
(−)-Oxypeucedanin hydrate (73) FR First isolation from the part Baba et al. (1990a)
(−)-Tert-O-methoxy peucedanin hydrate (74) FR First isolation from the part Baba et al. (1990a)
(−)-Sec-O-acetoxy peucedanin hydrate(75) FR First isolation from the part Baba et al. (1990a)
Pseudoisopsoralen (76) AP First isolation from the part Luo et al. (2012)
Angelicin (77) RT First isolation from the part Hata and Kozawa (1961)
Columbianadin (78) RT First isolation from the part Kozawa et al. (1978)
FR First isolation from the part Baba et al. 1990a)
(3′R)-Hydroxy columbianadin (79) (=(8S,9R)-8-angeloyl oxy-8,9-dihydrooroselol) EXD Anti-tumor-promoter activity: EBV-EA by TPA Akihisa et al. (2003)
RT First isolation from the part Sugamoto et al. (2009)
(8S,9R)-9-Angeloyloxy-8,9-dihydrooroselol (80) RT First isolation from the part Kozawa et al. (1978)
RT Anti-tumor-promoter activity: TPA-stimulated 32Pi-incorporation Okuyama et al. (1991)
Archangelicin (81) RT First isolation from the part Kozawa et al. (1978)
FR First isolation from the part Baba et al. (1990a)
RT Anti-tumor-promoter activity: TPA-stimulated 32Pi-incorporation Okuyama et al. (1991)
Lomatin (82) FR First isolation from the part Baba et al. (1990a)
Selinidin (83) RT First isolation from the part Baba et al. (1990b)
FR First isolation from the part Baba et al. (1990a)
EXD Anti-tumor-initiator activity: NOR 1 Akihisa et al. (2003)
EXD Anti-allergic activity: lgE-mediated mast cell activation (β-hexosaninidase, LTC4, TNF-α, FcεRI β-chain PLCγ1, p38 MAPK, IκB-α) Kishiro et al. (2008)
AP First isolation from the part Luo et al. (2012)
ST Anti-diabetic activity: PTP1B Li et al. (2015)
Selidinin (84) EXD Anti-inflammatory activity (details in the patent) Akihisa et al. (2007)
O-Isobutyroyllomatin (85) ST Anti-diabetic activity: PTP1B Li et al. (2015)
Khellactone (86) AP First isolation from the part Luo et al. (2012)
ST Anti-diabetic activity: PTP1B Li et al. (2015)
3′-Senecioyl khellactone (87) EXD Anti-tumor-promoter activity: EBV-EA by TPA Akihisa et al. (2003)
Anti-tumor-initiator activity: NOR 1
AP Anti-diabetic activity: α-glucosidase Luo et al. (2012)
Peguangxienin (88) EXD Anti-inflammatory activity: TPA-induced mouse ear edema Akihisa et al. (2007)
(3′R,4′R)-3′-Angeloyl khellactone (89) (miswritten as isolaserpitin) RT First isolation from the part Baba et al. (1990b)
FR First isolation from the part Baba et al. (1990a)
EXD

Anti-tumor-promoter activity: EBV-EA by TPA

Anti-tumor-initiator activity: NOR 1

Akihisa et al. (2003)
EXD Anti-inflammatory activity (details in the patent) Akihisa et al. (2007)
4′-Senecioyl khellactone (90) EXD Anti-tumor-promoter activity: EBV-EA by TPA Akihisa et al. (2003)
Anti-tumor-initiator activity: NOR 1
Isolemanidin (91) (miswritten as laserpitin) RT First isolation from the part Baba et al. (1990b)
FR First isolation from the part Baba et al. (1990a)
EXD

Anti-tumor-promoter activity: EBV-EA by TPA

Anti-tumor-initiator activity: NOR 1

Akihisa et al. (2003)
ST Anti-hyperlipidemic activity: serum HDL↑, hepatic TG↓ (hepatic TG lipase, differentiation factor 1) Ogawa et al. (2005b)
EXD Anti-inflammatory activity: TPA-induced mouse ear edema Akihisa et al. (2007)
Pteryxin (92) EXD

Anti-tumor-promoter activity: EBV-EA by TPA

Anti-tumor-initiator activity: NOR 1

Akihisa et al. (2003)
EXD Anti-inflammatory activity (details in the patent) Akihisa et al. (2007)
(+)-Cis-(3′R,4′R)-methylkhellactone (93) AP First isolation from the part Kil et al. (2016)
(−)-Trans-(3′R,4′S)-methylkhellactone (94), AP First isolation from the part Kil et al. (2016)
Dihydrocoumarin
 3,4-Dihydroxanthotoxin (95) AP First isolation from the part Kil et al. (2016)
Phenolics
5-n-Pentadecylresorcinol (96) EXD First isolation from the part Akihisa et al. (2003)
(Z)-p-Coumaryl alcohol (97) AP First isolation from the part Kil et al. (2016)
Acetylenes
Falcarindiol (98) EXD First isolation from the part Akihisa et al. (2003)
AP Anti-diabetic activity: α-glucosidase Luo et al. (2012)
ST Anti-diabetic activity: PTP1B Li et al. (2015)
Acetylenes
(11S,16R,Z)-11,16-Dihydroxyoctadeca-9,17-dien-12,14-diynyl acetate (99) EXD First isolation from the part Akihisa et al. (2006)
(10S,15R,Z)-10,15-Dihydroxyheptadeca-8,16-dien-11,13-diynyl acetate (100) AP Anti-diabetic activity: α-glucosidase Luo et al. (2012)
(11S,16R,Z)-Octadeca-9,17-dien-12,14-diyne-1,11,16-triol (101) AP First isolation from the part Luo et al. (2012)
Angelicol B (102) AP First isolation from the part Luo et al. (2012)
Sesquiterpene
Ashitabaol A (103) SD Anti-oxidative: free radical scavenging Aoki and Ohta (2010)
Diterpene
Steviol-13-O-β-d-glucopyranoside 19-β-d-glucopyranosyl ester (104) LF First isolation from the part Zhou et al. (2012)
Triterpenes
Daucosterol (105) LF First isolation from the part Zhou et al. (2012)
Stigmasterol (106) LF First isolation from the part Zhou et al. (2012)
Triterpenes
Pregnenolone (107) AP Anti-oxidative activity: DPPH radical scavenging Luo et al. (2012)
Nucleoside
Adenosine (108) AP First isolation from the part Park et al. (1996)
Saccharide
Sucrose (109) AP First isolation from the part Park et al. (1996)
AP Anti-mutagenic activity (AFB1) Park et al. (1997a)
Acids
Angelic acid (110) RT First isolation from the part Hata and Kozawa (1961)
Behenic acid (111) RT First isolation from the part Hata and Kozawa (1961)
Others
 1-Cerotol (112) LF First isolation from the part Zhou et al. (2012)
 (E)-2,6-Dimethylocta-5,7-diene-2,3-diol (113) AP First isolation from the part Luo et al. (2012)
 Angelicol A (114) AP Anti-oxidative activity: DPPH radical scavenging Luo et al. (2012)

aPlant part code: WP whole plant, RT root, AP aerial part (including stem and leaf), ST stem, LF leaf, EXD exudate, FR fruit, SD seed; other source code: Syn synthetic, Com commercial