Total synthesis of sauropunol A-D isolated from Sauropus rostratus genus plants

WANG Zihao; WANG Chengqian; XU Jinyi; WU Xiaoming; XIE Weijia

doi:10.11665/j.issn.1000-5048.20170407

Journal of China Pharmaceutical University > 2017 > 48(4): 432-439. > DOI: 10.11665/j.issn.1000-5048.20170407

Citation: WANG Zihao, WANG Chengqian, XU Jinyi, WU Xiaoming, XIE Weijia. Total synthesis of sauropunol A-D isolated from Sauropus rostratus genus plants[J]. Journal of China Pharmaceutical University, 2017, 48(4): 432-439. DOI: 10.11665/j.issn.1000-5048.20170407

WANG Zihao, WANG Chengqian, XU Jinyi, WU Xiaoming, XIE Weijia. Total synthesis of sauropunol A-D isolated from Sauropus rostratus genus plants[J]. Journal of China Pharmaceutical University, 2017, 48(4): 432-439. DOI: 10.11665/j.issn.1000-5048.20170407

Citation: WANG Zihao, WANG Chengqian, XU Jinyi, WU Xiaoming, XIE Weijia. Total synthesis of sauropunol A-D isolated from Sauropus rostratus genus plants[J]. Journal of China Pharmaceutical University, 2017, 48(4): 432-439. DOI: 10.11665/j.issn.1000-5048.20170407

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Total synthesis of sauropunol A-D isolated from Sauropus rostratus genus plants

WANG Zihao¹,

WANG Chengqian²,

XU Jinyi²,

WU Xiaoming¹,

XIE Weijia²

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Abstract

Abstract

Sauropunol A-D potentially with anti-inflammatory, anti-bacterial activities were recently isolated from traditional Chinese medicinal plant Sauropus rostratus. Herein, we report the total synthesis of sauropunol( A - D )starting from a commercially available 2-deoxy-D-arabino-hexopyranose. The trifluoromethane sulfonation of intermediates could simultaneously trigger intramolecular cyclization to afford 3, 6-anhydro hexofuranoside scaffold. The following deprotection reaction could produce sauropunol A , B and C / D with total yields of 21%, 5%, and 17%(isomer sauropunol C / D ), respectively. Structures of the target compounds were confirmed by comparison with NMR spectroscopic properties of those previously reported.

Keywords:
Sauropus rostratus,
sauropunol A-D,
3,6-anhydrohexosides,
intramolecular cyclization,
natural products,
total synthesis

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References (16)

References

[1]
Wang PH,Lee SS.Active chemical constituents from Sauropus androgynus[J].J Chin Chem Soc,1997,44(2):145-149.

[2]
Rao SN,Vasanth S,Pattabhi V.Lup-1,20(29)-dien-3-one,a triterpenoid from Agyneia bacciformis,A.Juss[J].Acta Crystallogr,2004,60(6):1092-1093.

[3]
Lu C, Bai L, Shen Y. Five unusual natural carbohydrates from Actinosynnema pretiosum[J].Chem Nat Comp,2008,44(5):594-597.

[4]
Bredt DS,Snyder SH.Nitric oxide,a physiological messenger molecule[J].Annu Rev Biochem,1994,63:175-195.

[5]
Kojda G,Kottenberg K.Regulation of basal myocardial function by NO[J].Cardiovasc Res,1999,41(3):514-523.

[6]
Nathan C,Xie Q.Nitric oxide synthases:roles,tolls,and controls[J].Cell,1994,78(6):915-918.

[7]
Wang CH,Wen L,Liu HL,et al.Five natural carbohydrates from the leaves of Sauropus rostratus[J].Carbohydr Res,2013,384(1):99-101.

[8]
Yang K,Wang Z,Brenner T,et al.Sucrose release from agar gels:effects of dissolution order and the network in homogeneity[J].Food Hydrocolloids,2015,43:100-106.

[9]
Kikuchi H,Saito Y,Komiya J,et al.Furanodictine A and B:amino sugar analogues produced by cellular slime mold dictyostelium discoideum showing neuronal differentiation activity[J].J Org Chem,2001,66(21):6982-6987.

[10]
Saulnier MG,Langley DR,Frennesson DB,et al.Novel 3′,6′-anhydro and N12,N13-bridged glycosylated fluoroindolo[2,3-a]carbazoles as topoisomerase I inhibitors.Fluorine as a leaving group from sp³ carbon[J].Org Lett,2005,7(7):1271-1274.

[11]
Shiraiwa K,Yuan S,Fujiyama A,et al.Benzyl benzoate glycoside and 3-deoxy-D-manno-2-octulosonic acid derivatives from Solidago decurrens[J].J Nat Prod,2011,75(1):88-92.

[12]
Fujita K,Yamamura H,Imoto T,et al.Synthesis of 6A,6X-di-O-(p-tosyl)-.gamma.-cyclodextrins and their structural determination through enzymic hydrolysis of 3A,6A;3X,6X-dianhydro-γ-cyclodextrins[J].J Org Chem,1988,53(9):1943.

[13]
Fujita K,Tahara T,Yamamura H,et al.Specific preparation and structure determination of 3A,3C,3E-tri-O-sulfonyl-β-cyclodextrin[J].J Org Chem,1990,55(3):877.

[14]
Jadhav V,Pedersen CM,Bols M.A study of anhydrocellulosesis a cellulose structure with residues in a ¹C₄conformation more prone to hydrolysis[J].Org Biomol Chem,2011,9(21):7525.

[15]
Liu L,Wang CQ,Liu D,et al.Construction of 3,6-anhydrohexosides via intramolecular cyclization of triflates and its application to the synthesis of natural product isolated from leaves of Sauropus rostratus[J].Org Lett,2014,16(19):5004-5007.

[16]
Zhang CX,Wang CQ,Wang ZH,et al.Total synthesis,structural elucidation and anti-inflammatory activity evaluation of 2-deoxy-3,6-anhydro hexofuranoside derivatives isolated from Sauropus rostratus[J].Org Biomol Chem,2016,14(46):10906-10913.

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[1]	Wang PH,Lee SS.Active chemical constituents from Sauropus androgynus[J].J Chin Chem Soc,1997,44(2):145-149.
[2]	Rao SN,Vasanth S,Pattabhi V.Lup-1,20(29)-dien-3-one,a triterpenoid from Agyneia bacciformis,A.Juss[J].Acta Crystallogr,2004,60(6):1092-1093.
[3]	Lu C, Bai L, Shen Y. Five unusual natural carbohydrates from Actinosynnema pretiosum[J].Chem Nat Comp,2008,44(5):594-597.
[4]	Bredt DS,Snyder SH.Nitric oxide,a physiological messenger molecule[J].Annu Rev Biochem,1994,63:175-195.
[5]	Kojda G,Kottenberg K.Regulation of basal myocardial function by NO[J].Cardiovasc Res,1999,41(3):514-523.
[6]	Nathan C,Xie Q.Nitric oxide synthases:roles,tolls,and controls[J].Cell,1994,78(6):915-918.
[7]	Wang CH,Wen L,Liu HL,et al.Five natural carbohydrates from the leaves of Sauropus rostratus[J].Carbohydr Res,2013,384(1):99-101.
[8]	Yang K,Wang Z,Brenner T,et al.Sucrose release from agar gels:effects of dissolution order and the network in homogeneity[J].Food Hydrocolloids,2015,43:100-106.
[9]	Kikuchi H,Saito Y,Komiya J,et al.Furanodictine A and B:amino sugar analogues produced by cellular slime mold dictyostelium discoideum showing neuronal differentiation activity[J].J Org Chem,2001,66(21):6982-6987.
[10]	Saulnier MG,Langley DR,Frennesson DB,et al.Novel 3′,6′-anhydro and N12,N13-bridged glycosylated fluoroindolo[2,3-a]carbazoles as topoisomerase I inhibitors.Fluorine as a leaving group from sp³ carbon[J].Org Lett,2005,7(7):1271-1274.
[11]	Shiraiwa K,Yuan S,Fujiyama A,et al.Benzyl benzoate glycoside and 3-deoxy-D-manno-2-octulosonic acid derivatives from Solidago decurrens[J].J Nat Prod,2011,75(1):88-92.
[12]	Fujita K,Yamamura H,Imoto T,et al.Synthesis of 6A,6X-di-O-(p-tosyl)-.gamma.-cyclodextrins and their structural determination through enzymic hydrolysis of 3A,6A;3X,6X-dianhydro-γ-cyclodextrins[J].J Org Chem,1988,53(9):1943.
[13]	Fujita K,Tahara T,Yamamura H,et al.Specific preparation and structure determination of 3A,3C,3E-tri-O-sulfonyl-β-cyclodextrin[J].J Org Chem,1990,55(3):877.
[14]	Jadhav V,Pedersen CM,Bols M.A study of anhydrocellulosesis a cellulose structure with residues in a ¹C₄conformation more prone to hydrolysis[J].Org Biomol Chem,2011,9(21):7525.
[15]	Liu L,Wang CQ,Liu D,et al.Construction of 3,6-anhydrohexosides via intramolecular cyclization of triflates and its application to the synthesis of natural product isolated from leaves of Sauropus rostratus[J].Org Lett,2014,16(19):5004-5007.
[16]	Zhang CX,Wang CQ,Wang ZH,et al.Total synthesis,structural elucidation and anti-inflammatory activity evaluation of 2-deoxy-3,6-anhydro hexofuranoside derivatives isolated from Sauropus rostratus[J].Org Biomol Chem,2016,14(46):10906-10913.

[1]	LIU Xiaohan, TAN Yunying, LI Qiang, CHEN Xu, FU Junjie, YIN Jian. Synthesis and antitumor activity evaluation of glycoconjugates derived from natural product harmine[J]. Journal of China Pharmaceutical University, 2023, 54(6): 729-742. DOI: 10.11665/j.issn.1000-5048.2023041101
[2]	SUN Dongyu, GONG Jingxu, LI Xuwen, HAN Guanying, GUO Yuewei. Studies on methyl xestopongoate analogues:design, synthesis and antitumor activities[J]. Journal of China Pharmaceutical University, 2018, 49(4): 413-421. DOI: 10.11665/j.issn.1000-5048.20180405
[3]	QIAO Yixue, MOU Yi, HUANG Zhangjian, AI Yong, KANG Fenghua, LAI Yisheng, ZHANG Yihua. Synthesis and antitumor activities of novel CDDO-Me analogues[J]. Journal of China Pharmaceutical University, 2015, 46(3): 289-293. DOI: 10.11665/j.issn.1000-5048.20150305
[4]	GU Xiaoke, TANG Xiaobo, HUANG Zhangjian, PENG Hui, ZHANG Yihua. Synthesis and antitumor activity of NO-releasing alkoxylbiphenyl derivatives[J]. Journal of China Pharmaceutical University, 2014, 45(6): 657-661. DOI: 10.11665/j.issn.1000-5048.20140606
[5]	HU Kun, ZHOU Anfei, JIANG Hefei, XU Yuanyuan, HUANG Qianhui, YANG Jie, CHEN Xin, REN Jie. Synthesis and antitumor activities of podophyllotoxin derivatives[J]. Journal of China Pharmaceutical University, 2014, 45(1): 33-38. DOI: 10.11665/j.issn.1000-5048.20140105
[6]	LIU Dexiu, PAN Huaying, SHI Hui, HUANG Xiaoying, LOU Hongxiang. Synthesis and antitumor activity of a novel bisbibenzyl derivative[J]. Journal of China Pharmaceutical University, 2013, 44(6): 515-519. DOI: 10.11665/j.issn.1000-5048.20130605
[7]	HU Kun, XU Hua-jin, XIN Wen-qun, CHEN Xin, REN Jie. Synthesis and antitumor activity of nitrogen mustard derivatives of formononetin[J]. Journal of China Pharmaceutical University, 2012, 43(2): 113-119.
[8]	ZHA Xiao-ming, ZHANG Fei-ran, SHAN Jia-qi, CHEN Yan-ke, ZHANG Yi-hua, LIU Jun, SUN Hong-bin. Synthesis and in vitro antitumor activities of novel soladulcidine derivatives[J]. Journal of China Pharmaceutical University, 2010, 41(6): 493-498.
[9]	Synthesis and antitumor activity of ent-kaurene diterpenoids[J]. Journal of China Pharmaceutical University, 2010, 41(1): 20-25.
[10]	ZHOU Mei, MA Lin, HAO Xiao-jiang, YANG Xiao-sheng. Antitumor activities of chemical constituents of Cephalotaxus fortunei in Guizhou province[J]. Journal of China Pharmaceutical University, 2009, 40(3): 209-212.

Total synthesis of sauropunol A-D isolated from Sauropus rostratus genus plants

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