Progress on Chemical and pharmacological research of C6-C3 compounds in genus Illicium

DENG Hua-ping; SUN Lei; XI Zhong-xin; LI Xia; CHEN Cheng; SUN Lian-na

doi:10.3969/j.issn.1006-0111.2012.01.003

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2012 > 30(1): 8-13

DENG Hua-ping, SUN Lei, XI Zhong-xin, LI Xia, CHEN Cheng, SUN Lian-na. Progress on Chemical and pharmacological research of C6-C3 compounds in genus Illicium[J]. Journal of Pharmaceutical Practice and Service, 2012, 30(1): 8-13. doi: 10.3969/j.issn.1006-0111.2012.01.003

Citation:

DENG Hua-ping, SUN Lei, XI Zhong-xin, LI Xia, CHEN Cheng, SUN Lian-na. Progress on Chemical and pharmacological research of C₆-C₃ compounds in genus Illicium[J]. Journal of Pharmaceutical Practice and Service, 2012, 30(1): 8-13. doi: 10.3969/j.issn.1006-0111.2012.01.003

Progress on Chemical and pharmacological research of C₆-C₃ compounds in genus Illicium

doi: 10.3969/j.issn.1006-0111.2012.01.003

1.
School of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350108, China;Department of Pharmacognosy, School of Pharmacy, Second Military Medical University, Shanghai 200433, China
2.
Department of Pharmacognosy, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2011-10-11
Rev Recd Date: 2011-10-30

Abstract

Objective To review the chemical and pharmacological study of the C₆-C₃ compounds from genus Illicium and provide the reference for further development of genus Illicium. Methods Relevant literatures of C₆-C₃ compounds in genus Illicium were searched and summarized. Results and Conclusion The plants of this genus had varying types C₆-C₃ compounds which had good anti-inflammatory, neurotrophic, anti-cancer and anti-oxidation activities. The C₆-C₃ compounds in this genus had broad prospects for medicinal development.
- Genus Illicium,
- C₆-C₃ compounds,
- biological activity

References

[1]	中国科学院中国植物志编辑委员会. 中国植物志:第30卷[M]. 北京:科学出版社,1996:199.
[2]	Shibuya M, Abe K, Nakahashi Y, et al. Phenolic components from leaf oil of Illicium anisatum L[J]. Chem Pharm Bull, 1978, 26(9):2671.
[3]	Yakushijin K, Tohshima T, Suzuki R, et al. Studies on the constituents of the plants of Illicium species. II. structures of phenolic components[J]. Chem Pharm Bull, 1983, 31(8):2879.
[4]	Kouno I, Yanagida Y, Shimono S, et al. Phenylpropanoids from the barks of Illicium difengpi[J]. Chem Pharm Bull, 1992, 40(9):2461.
[5]	Sy LK, Saunders RMK, Brown GD. Phytochemistry of Illicium dunnianum and the systematic position of the illiciaceae[J].Phytochemisty, 1997, 44(6):1099.
[6]	Sy LK, Brown GD. Novel Phenylpropanoids and Lignans from Illicium verum[J]. J Nat Prod, 1998, 61(8):987.
[7]	Jiang ZH, Tanaka T, Kouno I. New phenylpropanoid glycosides from the fruits of Illicium anisatum[J]. Chem Pharm Bull, 1999, 47(3):421.
[8]	Lee SW, Li G, Lee KS,et al. A new phenylpropanoid glucoside from the fruits of Illicium verum[J]. Arch Pharm Res, 2003, 26(8):591.
[9]	Lee SW, Li G, Lee KS, et al. Preventive agents against sepsis and new phenylpropanoid glucosides from the fruits of Illicium verum[J]. Planta Med, 2003, 69(9):861.
[10]	Song WY, Ma YB, Bai X, et al. Two new compounds and anti-HIV active constituents from Illicium verum[J]. Planta Med, 2007, 73(4):372.
[11]	Moriyama M, Huang JM, Yang CS, et al. Two New Sesquiterpenoids and Two new prenylated phenylpropanoids from Illicium fargesii, and neuroprotective activity of Macranthol[J]. Chem Pharm Bull, 2008, 56(8):1201.
[12]	Takaoka S, Takaoka N, Minoshima Y, et al. Isolation, synthesis, and neurite outgrowth-promoting activity of llicinin A from the flowers of Illicium anisatum[J]. Tetrahedron, 2009, 65(40):8354.
[13]	Lin YX, Fazary AE, Chen SY, et al. Illicaborins A-C, three prenylated C₆-C₃ compounds from the fruits of Illicium arborescens[J]. Food Chemistry, 2010, 123(4):1105.
[14]	Kubo M, Shima N, Harada K, et al. New prenylated C₆-C₃ compounds from the twigs of Illicium anisatum[J]. Chem Pharm Bull, 2011, 59(7):898.
[15]	Ma SG, Tang WZ, Yu SS, et al. Four new phenolic diglycosides from the roots of Illicium oligandrum[J]. Carbohydrate Research, 2011, 346(9)1165.
[16]	Kouno I, Hashimoto A, Kawano N, et al. New sesqui-neolignan from the pericarps of Illicium macranthum[J].Chem Pharm Bull, 1989, 37(5):1291.
[17]	Kouno I, Morisaki T,Hara Y,et al. Two new sesquineolignans from the bark of Illicium dunnianum[J]. Chem Pharm Bull, 1991, 39(10):2606.
[18]	Kouno I, Hashimoto M, Enjoji S, et al. Isolation of neoanisatin derivatives from the pericarps of Illicium majus with other constituents[J]. Chem Pharm Bull, 1991, 39(7):1773.
[19]	Kouno I, Iwamoto C, Kameda Y, et al. A new triphenyl-type neolignan and a biphenylneolignan from the bark of Illicium simonsii[J]. Chem Pharm Bull,1994, 42(1):112.
[20]	Schmidt TJ, Heilmann J. Tetrahydrofuran lignans from Illicium floridanum and their activity in a luminol enhanced chemiluminescence assay[J]. Planta Med, 2000, 66(8):749.
[21]	Tang WZ, Liu YB, Yu SS, et al. New sesquiterpene lactone and neolignan glycosides with antioxidant and anti-inflammatory activities from the fruits of Illicium oligandrum[J]. Planta Med, 2007, 73(5):484.
[22]	Moriyama M, Huang JM, Yang CS, et al. Structure and neurotrophic activity of novel sesqui-neolignans from the pericarps of Illicium fargesii[J]. Tetrahedron, 2007, 63(20):4243.
[23]	Fang L, Du D, Ding GZ, et al. Neolignans and glycosides from the stem bark of Illicium difengpi[J]. J Nat Prod, 2010, 73(5):818.
[24]	Xiang WJ, Ma L, Hu LH. Neolignans and flavonoids from the root bark of Illicium henryi[J]. Fitoterapia, 2010, 81(8):1228.
[25]	Yakushijin K, Tohshima T, Kitagawa E, et al. Studies on the constituents of the plants of Illicium Species. III. Structure elucidations of novel phytoquinoids,Illicinones and Illifunones from Illicium tashiroi MAXIM. and I. arborescens HAYATA[J]. Chem Pharm Bull, 1984, 32(1):11.
[26]	Fukuyama Y, Shida N, Sakurai N, et al. Prenylated C₆-C₃ compounds from Illicium tashiroi[J] Phytochemistry, 1992, 31(11):3975.
[27]	Fukuyama Y, Shida N, Hata Y, et al. Prenylated C₆-C₃ compounds related to Illicinone E from Illicium tashiroi[J]. Phytochemistry, 1994, 37(6):1653.
[28]	Fukuyama Y, Okamoto K, Kubo Y, et al. New chlorine-containing prenylated C₆-C₃ compounds increasing choline acetyltransferase (ChAT) activity in culture of postnatal rat septal neurons from Illicium tashiroi[J]. Chem Pharm Bull, 1994, 42(10):2199.
[29]	Fukuyama Y, Shida N, Kodama M, et al. Tricycloillicinone, a novel prenylated C₆-C₃ compound increasing choline acetyltransferase (ChAT) activity, isolated from Illicium tashiroi[J]. Chem Pharm Bull, 1995, 43(12):2270.
[30]	Fukuyama Y, Hata Y, Kodama M. Bicycloillicinone asarone acetal_ A novel prenylated C₆-C₃ compound increasing choline acetyltransferase (ChAT) activity from Illicium tashiroi[J].Planta Med, 1997, 63(3):275.
[31]	Sy LK, Brown GD. A sesquilignan from Illicium dunnianum[J]. Phytochemistry, 1996,43(6):1417.
[32]	Kouno I, Shimamoto S, Jiang ZH, et al. Prenylated C₆-C₃ compounds from root bark of Illicium anisatum[J]. Phytochemistry, 1997, 46(8):1389.
[33]	唐文照,庾石山. 少药八角果实及茎皮化学成分和药理活性研究［D］. 北京:中国协和医科大学,2007.
[34]	Tang WZ, Ma SG, Yu SS, et al. Rearranged prenylated C₆-C₃ compounds and a highly oxygenated seco-prezizaane-type sesquiterpene from the stem bark of Illicium oligandrum[J]. J Nat Prod, 2009, 72(6):1017.
[35]	Wu XF, Li Y, Lu HN, et al. Prenylated C₆-C₃ compounds from the fruits of Illicium simonsii[J]. Journal of Asian Natural Products Research, 2009, 11(12):1056.
[36]	Chang JY, Abd Ei-Razek MH, Chen YH, et al. Phytoquinoids and secoprezizaane-type sesquiterpenes from Illicium arborescens[J]. Helvetica Chimica Acta, 2010, 93(1):123.
[37]	Ma SG, Tang WZ, Liu YX, et al. Prenylated C₆-C₃ compounds with molecular diversity from the roots of Illicium oligandrum[J]. Phytochemistry, 2011, 72(1):115.
[38]	Itoigawa M, Ito C, Tokuda H, et al. Cancer chemopreventive activity of phenylpropanoids and phytoquinoids from Illicium plants[J]. Cancer Letters, 2004, 214(2):165.

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通讯作者: 陈斌, [email protected]

1.
沈阳化工大学材料科学与工程学院沈阳 110142

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Progress on Chemical and pharmacological research of C₆-C₃ compounds in genus Illicium

1. School of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350108, China;Department of Pharmacognosy, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

2. Department of Pharmacognosy, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2011-10-11

Rev Recd Date: 2011-10-30

Key words:

Abstract: Objective To review the chemical and pharmacological study of the C₆-C₃ compounds from genus Illicium and provide the reference for further development of genus Illicium. Methods Relevant literatures of C₆-C₃ compounds in genus Illicium were searched and summarized. Results and Conclusion The plants of this genus had varying types C₆-C₃ compounds which had good anti-inflammatory, neurotrophic, anti-cancer and anti-oxidation activities. The C₆-C₃ compounds in this genus had broad prospects for medicinal development.

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Reference (38)

[1]	中国科学院中国植物志编辑委员会. 中国植物志:第30卷[M]. 北京:科学出版社,1996:199.
[2]	Shibuya M, Abe K, Nakahashi Y, et al. Phenolic components from leaf oil of Illicium anisatum L[J]. Chem Pharm Bull, 1978, 26(9):2671.
[3]	Yakushijin K, Tohshima T, Suzuki R, et al. Studies on the constituents of the plants of Illicium species. II. structures of phenolic components[J]. Chem Pharm Bull, 1983, 31(8):2879.
[4]	Kouno I, Yanagida Y, Shimono S, et al. Phenylpropanoids from the barks of Illicium difengpi[J]. Chem Pharm Bull, 1992, 40(9):2461.
[5]	Sy LK, Saunders RMK, Brown GD. Phytochemistry of Illicium dunnianum and the systematic position of the illiciaceae[J].Phytochemisty, 1997, 44(6):1099.
[6]	Sy LK, Brown GD. Novel Phenylpropanoids and Lignans from Illicium verum[J]. J Nat Prod, 1998, 61(8):987.
[7]	Jiang ZH, Tanaka T, Kouno I. New phenylpropanoid glycosides from the fruits of Illicium anisatum[J]. Chem Pharm Bull, 1999, 47(3):421.
[8]	Lee SW, Li G, Lee KS,et al. A new phenylpropanoid glucoside from the fruits of Illicium verum[J]. Arch Pharm Res, 2003, 26(8):591.
[9]	Lee SW, Li G, Lee KS, et al. Preventive agents against sepsis and new phenylpropanoid glucosides from the fruits of Illicium verum[J]. Planta Med, 2003, 69(9):861.
[10]	Song WY, Ma YB, Bai X, et al. Two new compounds and anti-HIV active constituents from Illicium verum[J]. Planta Med, 2007, 73(4):372.
[11]	Moriyama M, Huang JM, Yang CS, et al. Two New Sesquiterpenoids and Two new prenylated phenylpropanoids from Illicium fargesii, and neuroprotective activity of Macranthol[J]. Chem Pharm Bull, 2008, 56(8):1201.
[12]	Takaoka S, Takaoka N, Minoshima Y, et al. Isolation, synthesis, and neurite outgrowth-promoting activity of llicinin A from the flowers of Illicium anisatum[J]. Tetrahedron, 2009, 65(40):8354.
[13]	Lin YX, Fazary AE, Chen SY, et al. Illicaborins A-C, three prenylated C₆-C₃ compounds from the fruits of Illicium arborescens[J]. Food Chemistry, 2010, 123(4):1105.
[14]	Kubo M, Shima N, Harada K, et al. New prenylated C₆-C₃ compounds from the twigs of Illicium anisatum[J]. Chem Pharm Bull, 2011, 59(7):898.
[15]	Ma SG, Tang WZ, Yu SS, et al. Four new phenolic diglycosides from the roots of Illicium oligandrum[J]. Carbohydrate Research, 2011, 346(9)1165.
[16]	Kouno I, Hashimoto A, Kawano N, et al. New sesqui-neolignan from the pericarps of Illicium macranthum[J].Chem Pharm Bull, 1989, 37(5):1291.
[17]	Kouno I, Morisaki T,Hara Y,et al. Two new sesquineolignans from the bark of Illicium dunnianum[J]. Chem Pharm Bull, 1991, 39(10):2606.
[18]	Kouno I, Hashimoto M, Enjoji S, et al. Isolation of neoanisatin derivatives from the pericarps of Illicium majus with other constituents[J]. Chem Pharm Bull, 1991, 39(7):1773.
[19]	Kouno I, Iwamoto C, Kameda Y, et al. A new triphenyl-type neolignan and a biphenylneolignan from the bark of Illicium simonsii[J]. Chem Pharm Bull,1994, 42(1):112.
[20]	Schmidt TJ, Heilmann J. Tetrahydrofuran lignans from Illicium floridanum and their activity in a luminol enhanced chemiluminescence assay[J]. Planta Med, 2000, 66(8):749.
[21]	Tang WZ, Liu YB, Yu SS, et al. New sesquiterpene lactone and neolignan glycosides with antioxidant and anti-inflammatory activities from the fruits of Illicium oligandrum[J]. Planta Med, 2007, 73(5):484.
[22]	Moriyama M, Huang JM, Yang CS, et al. Structure and neurotrophic activity of novel sesqui-neolignans from the pericarps of Illicium fargesii[J]. Tetrahedron, 2007, 63(20):4243.
[23]	Fang L, Du D, Ding GZ, et al. Neolignans and glycosides from the stem bark of Illicium difengpi[J]. J Nat Prod, 2010, 73(5):818.
[24]	Xiang WJ, Ma L, Hu LH. Neolignans and flavonoids from the root bark of Illicium henryi[J]. Fitoterapia, 2010, 81(8):1228.
[25]	Yakushijin K, Tohshima T, Kitagawa E, et al. Studies on the constituents of the plants of Illicium Species. III. Structure elucidations of novel phytoquinoids,Illicinones and Illifunones from Illicium tashiroi MAXIM. and I. arborescens HAYATA[J]. Chem Pharm Bull, 1984, 32(1):11.
[26]	Fukuyama Y, Shida N, Sakurai N, et al. Prenylated C₆-C₃ compounds from Illicium tashiroi[J] Phytochemistry, 1992, 31(11):3975.
[27]	Fukuyama Y, Shida N, Hata Y, et al. Prenylated C₆-C₃ compounds related to Illicinone E from Illicium tashiroi[J]. Phytochemistry, 1994, 37(6):1653.
[28]	Fukuyama Y, Okamoto K, Kubo Y, et al. New chlorine-containing prenylated C₆-C₃ compounds increasing choline acetyltransferase (ChAT) activity in culture of postnatal rat septal neurons from Illicium tashiroi[J]. Chem Pharm Bull, 1994, 42(10):2199.
[29]	Fukuyama Y, Shida N, Kodama M, et al. Tricycloillicinone, a novel prenylated C₆-C₃ compound increasing choline acetyltransferase (ChAT) activity, isolated from Illicium tashiroi[J]. Chem Pharm Bull, 1995, 43(12):2270.
[30]	Fukuyama Y, Hata Y, Kodama M. Bicycloillicinone asarone acetal_ A novel prenylated C₆-C₃ compound increasing choline acetyltransferase (ChAT) activity from Illicium tashiroi[J].Planta Med, 1997, 63(3):275.
[31]	Sy LK, Brown GD. A sesquilignan from Illicium dunnianum[J]. Phytochemistry, 1996,43(6):1417.
[32]	Kouno I, Shimamoto S, Jiang ZH, et al. Prenylated C₆-C₃ compounds from root bark of Illicium anisatum[J]. Phytochemistry, 1997, 46(8):1389.
[33]	唐文照,庾石山. 少药八角果实及茎皮化学成分和药理活性研究［D］. 北京:中国协和医科大学,2007.
[34]	Tang WZ, Ma SG, Yu SS, et al. Rearranged prenylated C₆-C₃ compounds and a highly oxygenated seco-prezizaane-type sesquiterpene from the stem bark of Illicium oligandrum[J]. J Nat Prod, 2009, 72(6):1017.
[35]	Wu XF, Li Y, Lu HN, et al. Prenylated C₆-C₃ compounds from the fruits of Illicium simonsii[J]. Journal of Asian Natural Products Research, 2009, 11(12):1056.
[36]	Chang JY, Abd Ei-Razek MH, Chen YH, et al. Phytoquinoids and secoprezizaane-type sesquiterpenes from Illicium arborescens[J]. Helvetica Chimica Acta, 2010, 93(1):123.
[37]	Ma SG, Tang WZ, Liu YX, et al. Prenylated C₆-C₃ compounds with molecular diversity from the roots of Illicium oligandrum[J]. Phytochemistry, 2011, 72(1):115.
[38]	Itoigawa M, Ito C, Tokuda H, et al. Cancer chemopreventive activity of phenylpropanoids and phytoquinoids from Illicium plants[J]. Cancer Letters, 2004, 214(2):165.

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Progress on Chemical and pharmacological research of C₆-C₃ compounds in genus Illicium

doi: 10.3969/j.issn.1006-0111.2012.01.003

Abstract

References

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通讯作者: 陈斌, [email protected]

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Progress on Chemical and pharmacological research of C₆-C₃ compounds in genus Illicium

doi: 10.3969/j.issn.1006-0111.2012.01.003

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Progress on Chemical and pharmacological research of C6-C3 compounds in genus Illicium

doi: 10.3969/j.issn.1006-0111.2012.01.003

Abstract

References

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通讯作者: 陈斌, [email protected]

Article Metrics

Related

Proportional views