Merrilactone A is one of the four sesquiterpenes that were newly discovered from the fruit of Illicium merrillianum in 2000.[1] Members of the genus Illicium include Chinese star anise, widely used as a spice for flavouring food and beverages, and also poisonous plants such as Japanese star anise.[2] Chemical studies of Illicium have developed rapidly over the last 20 years, and merrilactone A has been shown to have neurotrophic activity in fetal rat corticalneuron cultures.[3] This has led researchers to believe that Merrilactone A may hold therapeutic potential in the treatment of neuro-degenerative diseases such as Alzheimer's disease and Parkinson's disease.[4]
Merrilactone A occurs naturally in Illicium merrillianum, a plant indigenous to southern China and Myanmar.[3] The genus Illicium belongs to the family Illiciaceae and is an evergreen shrub or tree. Approximately 40 species are disjunctively distributed in eastern North America, Mexico, the West Indies, and eastern Asia. The highest concentration of species is in northern Myanmar and southern China, where nearly 35 species have been described. The fruits of the Illicium species are distinctive star-shaped follicles that have a characteristic refreshing flavour. The fruits of Illicium merrillianum also have an aromatic odor, bland taste and cause numbness of the tongue when chewed.[2]
The only economically important product from this genus is the fruit of Illicium verum, or Chinese star anise, which is widely used as a spice for flavouring food and beverages. In contrast, the fruit of Japanese star anise, Illicium anisatum, have been known to be very toxic for several centuries.
Biological activity
Merrilactone A was found to exhibit a significant neurotrophic activity, such as greatly promoting neurite outgrowth in the primary cultures of fetal rat corticalneurons at concentrations from 10 to 0.1 μmol/L. It was also found that this compound had a property of neuroprotection at same concentration.[1]
Biosynthesis
This compound is originated from mevalonic acid pathway which produce dimethylallyl diphosphate (DMAPP) from acetyl-CoA. Three DMAPPs, or one DMAPP and two isopentenyl diphosphate (IPP), are made into a farnesyl diphosphate (FPP), which is the fundamental precursor of sesquiterpene, and then sesquiterpene cyclise enzymes cause it a cyclization. The synthesis up to here is well known, though process after the first cyclization was unclear. Anislactone-type sesquiterpenes which merrilactone A belongs to has been thought to be biosynthesized from majucin since they have γ-lactone.[5] However, this pathway has trouble to elucidate some configurations and other feature they have. The biosynthesis shown in the figure was newly proposed and solved these problems. The point of this pathway is that seco-prezizaane, anislactone and tashironin group which are all found in Illicium are all derived from the same intermediate 6. This is expected to be able to give all characteristic sesquiterpenes in Illicium plants a reasonable explanation of biosynthesis.
Total synthesis
Since the discovery of merrilactone A, many methods of total synthesis have been proposed, of which four produce racemic material,[6][7][8][9] and two produce the natural enantiomer.[10][11]
References
^ abFukuyama, Yoshiyasu; Huang, Jian-mei; Nakade, Kousuke; Yokoyama, Ritsuko (2001-09-01). 72 (P-29) シキミ科植物(Illicium merrillianum)のアニスラクトン型セスキテルペンの構造と神経突起伸展活性(ポスター発表の部) [72 (P-29) Structure and Neurotrophic Activity of Anislactone-type Sesquiterpenes from Illicium merrillianum]. Symposium on the chemistry of natural products (in Japanese). Vol. 43. pp. 425–430. Retrieved 2009-12-16.
^ abJodral, M. M. (2004). Illicium, Pimpinella and Foeniculum. Granada: CRC Press. ISBN0-415-32246-4.
^ abHuang, Jian-mei; Yokoyama, Ritsuko; Yang, Chun-shu; Yoshiyasu, Fukuyama (August 2000). "Merrilactone A, a novel neurotrophic sesquiterpene dilactone from Illicium merrillianum". Tetrahedron Letters. 41 (32): 6111–6114. doi:10.1016/S0040-4039(00)01023-6.
^Inoue, Masayuki; Lee, Nayoung; Kasuya, Satoshi; Sato, Takaaki; Hirama, Masahiro; Moriyama, Miyako; Fukuyama, Yoshiyasu (2007-04-13). "Total synthesis and bioactivity of an unnatural enantiomer of Merrilactone A: development of an enantioselective desymmetrization strategy". Journal of Organic Chemistry. 72 (8): 3065–3075. doi:10.1021/jo0700474. PMID 17355151.
^Kouno, I.; Mori, K.; Okamoto, S.; Sato, S. Structures of Anislactone A and B; Novel Type of Sesquiterpene Lactones from the Pericarps of Illicium anisatum. Chem. Pharm. Bull. 1990, 38, 3060-3063
^Birman, Vladimir B.; Danishefsky, Samuel J. (2002). "The Total Synthesis of (±)-Merrilactone A". Journal of the American Chemical Society. 124 (10): 2080–1. doi:10.1021/ja012495d. PMID 11878938.
^Inoue, Masayuki; et al. (2003). "Total Synthesis of Merrilactone A". J. Am. Chem. Soc. 125 (36): 10772–3. doi:10.1021/ja036587+. PMID 12952441.
^Mehta, Goverdhan; Singh, S. Robindro (2006). "Total Synthesis of (±)-Merrilactone A". Angewandte Chemie International Edition. 45 (6): 953–5. doi:10.1002/anie.200503618. PMID 16381043.
^He, Wei; Huang, Jie; Sun, Xiufeng; Frontier, Alison J. (2008). "Total Synthesis of (±)-Merrilactone A". Journal of the American Chemical Society. 130 (1): 300–8. doi:10.1021/ja0761986. PMID 18067294.
^Waters, Stephen P.; Tian, Yuan; Li, Yue-Ming; Danishefsky, Samuel J. (2005). "Total Synthesis of (−)-Scabronine G, an Inducer of Neurotrophic Factor Production". Journal of the American Chemical Society. 127 (39): 13514–5. doi:10.1021/ja055220x. PMID 16190712.
^Inoue, Masayuki; Sato, Takaaki; Hirama, Masahiro (2006). "Asymmetric Total Synthesis of (−)-Merrilactone A: Use of a Bulky Protecting Group as Long-Range Stereocontrolling Element". Angewandte Chemie International Edition. 45 (29): 4843–8. doi:10.1002/anie.200601358. PMID 16795104.
January 31, 2023
merrilactone, four, sesquiterpenes, that, were, newly, discovered, from, fruit, illicium, merrillianum, 2000, members, genus, illicium, include, chinese, star, anise, widely, used, spice, flavouring, food, beverages, also, poisonous, plants, such, japanese, st. Merrilactone A is one of the four sesquiterpenes that were newly discovered from the fruit of Illicium merrillianum in 2000 1 Members of the genus Illicium include Chinese star anise widely used as a spice for flavouring food and beverages and also poisonous plants such as Japanese star anise 2 Chemical studies of Illicium have developed rapidly over the last 20 years and merrilactone A has been shown to have neurotrophic activity in fetal rat cortical neuron cultures 3 This has led researchers to believe that Merrilactone A may hold therapeutic potential in the treatment of neuro degenerative diseases such as Alzheimer s disease and Parkinson s disease 4 Merrilactone A NamesPreferred IUPAC name 1aS 2S 3aS 3bS 6aS 6bR 2 Hydroxy 1a 3b 6a trimethylhexahydro 3H 6H 3a 1a1 epoxyethano oxeto 2 3 4 3 4 pentaleno 1 2 c furan 6 8 dioneOther names Merrilactone AIdentifiersCAS Number 301842 37 5 Y3D model JSmol Interactive imageChemSpider 8101770 NPubChem CID 9926135UNII DZS2XP3QH2 YInChI InChI 1S C15H18O6 c1 11 6 19 10 18 12 11 2 9 14 5 8 17 20 15 11 14 4 7 16 13 14 3 21 9 h7 9 16H 4 6H2 1 3H3 t7 9 11 12 13 14 15 m0 s1 NKey RJVZPYYKUUJWSI YTDOHZAMSA N NInChI 1 C15H18O6 c1 11 6 19 10 18 12 11 2 9 14 5 8 17 20 15 11 14 4 7 16 13 14 3 21 9 h7 9 16H 4 6H2 1 3H3 t7 9 11 12 13 14 15 m0 s1Key RJVZPYYKUUJWSI YTDOHZAMBWSMILES O C2OC C 3 C 54OC O C C 51 C O C H 1 C 23C C H O C4 C CPropertiesChemical formula C 15H 18O 6Molar mass 294 303 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Occurrence 2 Biological activity 3 Biosynthesis 4 Total synthesis 5 ReferencesOccurrence EditMerrilactone A occurs naturally in Illicium merrillianum a plant indigenous to southern China and Myanmar 3 The genus Illicium belongs to the family Illiciaceae and is an evergreen shrub or tree Approximately 40 species are disjunctively distributed in eastern North America Mexico the West Indies and eastern Asia The highest concentration of species is in northern Myanmar and southern China where nearly 35 species have been described The fruits of the Illicium species are distinctive star shaped follicles that have a characteristic refreshing flavour The fruits of Illicium merrillianum also have an aromatic odor bland taste and cause numbness of the tongue when chewed 2 The only economically important product from this genus is the fruit of Illicium verum or Chinese star anise which is widely used as a spice for flavouring food and beverages In contrast the fruit of Japanese star anise Illicium anisatum have been known to be very toxic for several centuries Biological activity EditMerrilactone A was found to exhibit a significant neurotrophic activity such as greatly promoting neurite outgrowth in the primary cultures of fetal rat cortical neurons at concentrations from 10 to 0 1 mmol L It was also found that this compound had a property of neuroprotection at same concentration 1 Biosynthesis EditThis compound is originated from mevalonic acid pathway which produce dimethylallyl diphosphate DMAPP from acetyl CoA Three DMAPPs or one DMAPP and two isopentenyl diphosphate IPP are made into a farnesyl diphosphate FPP which is the fundamental precursor of sesquiterpene and then sesquiterpene cyclise enzymes cause it a cyclization The synthesis up to here is well known though process after the first cyclization was unclear Anislactone type sesquiterpenes which merrilactone A belongs to has been thought to be biosynthesized from majucin since they have g lactone 5 However this pathway has trouble to elucidate some configurations and other feature they have The biosynthesis shown in the figure was newly proposed and solved these problems The point of this pathway is that seco prezizaane anislactone and tashironin group which are all found in Illicium are all derived from the same intermediate 6 This is expected to be able to give all characteristic sesquiterpenes in Illicium plants a reasonable explanation of biosynthesis Total synthesis EditSince the discovery of merrilactone A many methods of total synthesis have been proposed of which four produce racemic material 6 7 8 9 and two produce the natural enantiomer 10 11 References Edit a b Fukuyama Yoshiyasu Huang Jian mei Nakade Kousuke Yokoyama Ritsuko 2001 09 01 72 P 29 シキミ科植物 Illicium merrillianum のアニスラクトン型セスキテルペンの構造と神経突起伸展活性 ポスター発表の部 72 P 29 Structure and Neurotrophic Activity of Anislactone type Sesquiterpenes fromIllicium merrillianum Symposium on the chemistry of natural products in Japanese Vol 43 pp 425 430 Retrieved 2009 12 16 a b Jodral M M 2004 Illicium Pimpinella and Foeniculum Granada CRC Press ISBN 0 415 32246 4 a b Huang Jian mei Yokoyama Ritsuko Yang Chun shu Yoshiyasu Fukuyama August 2000 Merrilactone A a novel neurotrophic sesquiterpene dilactone from Illicium merrillianum Tetrahedron Letters 41 32 6111 6114 doi 10 1016 S0040 4039 00 01023 6 Inoue Masayuki Lee Nayoung Kasuya Satoshi Sato Takaaki Hirama Masahiro Moriyama Miyako Fukuyama Yoshiyasu 2007 04 13 Total synthesis and bioactivity of an unnatural enantiomer of Merrilactone A development of an enantioselective desymmetrization strategy Journal of Organic Chemistry 72 8 3065 3075 doi 10 1021 jo0700474 PMID 17355151 Kouno I Mori K Okamoto S Sato S Structures of Anislactone A and B Novel Type of Sesquiterpene Lactones from the Pericarps of Illicium anisatum Chem Pharm Bull 1990 38 3060 3063 Birman Vladimir B Danishefsky Samuel J 2002 The Total Synthesis of Merrilactone A Journal of the American Chemical Society 124 10 2080 1 doi 10 1021 ja012495d PMID 11878938 Inoue Masayuki et al 2003 Total Synthesis of Merrilactone A J Am Chem Soc 125 36 10772 3 doi 10 1021 ja036587 PMID 12952441 Mehta Goverdhan Singh S Robindro 2006 Total Synthesis of Merrilactone A Angewandte Chemie International Edition 45 6 953 5 doi 10 1002 anie 200503618 PMID 16381043 He Wei Huang Jie Sun Xiufeng Frontier Alison J 2008 Total Synthesis of Merrilactone A Journal of the American Chemical Society 130 1 300 8 doi 10 1021 ja0761986 PMID 18067294 Waters Stephen P Tian Yuan Li Yue Ming Danishefsky Samuel J 2005 Total Synthesis of Scabronine G an Inducer of Neurotrophic Factor Production Journal of the American Chemical Society 127 39 13514 5 doi 10 1021 ja055220x PMID 16190712 Inoue Masayuki Sato Takaaki Hirama Masahiro 2006 Asymmetric Total Synthesis of Merrilactone A Use of a Bulky Protecting Group as Long Range Stereocontrolling Element Angewandte Chemie International Edition 45 29 4843 8 doi 10 1002 anie 200601358 PMID 16795104 Retrieved from https en wikipedia org w index php title Merrilactone A amp oldid 1105148799, wikipedia, wiki, book, books, library,
