Monoterpene indole alkaloids from the aerial parts of Ophiorrhiza brevidentata and their immunological activities

doi:10.1007/s13659-025-00575-y

Natural Products and Bioprospecting ›› 2026, Vol. 16 ›› Issue (2): 20-20.DOI: 10.1007/s13659-025-00575-y

• ORIGINAL ARTICLES • Previous Articles Next Articles

Monoterpene indole alkaloids from the aerial parts of Ophiorrhiza brevidentata and their immunological activities

Fan Xu¹, Zheng-Hui Li^1,2, Meng-Lin Feng¹, Jia-Yu Jin¹, Bao-Bao Shi^1,2, Ji-Kai Liu^1,2

1. School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, People's Republic of China;
2. International Cooperation Base for Active Substances in Traditional Chinese Medicine in Hubei Province, School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, People's Republic of China

Received:2025-09-04 Online:2026-04-22 Published:2026-04-22
Contact: Bao-Bao Shi,Email:2021068@mail.scuec.edu.cn;Ji-Kai Liu,Email:liujikai@mail.scuec.edu.cn
Supported by:
National Natural Science Foundation of China, 82204239, baobao shi, Hubei Province Department of Education Scientific Research Program Guidance Project, B2024255, baobao shi, Fundamental Research Funds for the South-Central MinZu University, YZY24019, baobao shi

Monoterpene indole alkaloids from the aerial parts of Ophiorrhiza brevidentata and their immunological activities

Fan Xu¹, Zheng-Hui Li^1,2, Meng-Lin Feng¹, Jia-Yu Jin¹, Bao-Bao Shi^1,2, Ji-Kai Liu^1,2

1. School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, People's Republic of China;
2. International Cooperation Base for Active Substances in Traditional Chinese Medicine in Hubei Province, School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, People's Republic of China

通讯作者: Bao-Bao Shi,Email:2021068@mail.scuec.edu.cn;Ji-Kai Liu,Email:liujikai@mail.scuec.edu.cn
基金资助:
National Natural Science Foundation of China, 82204239, baobao shi, Hubei Province Department of Education Scientific Research Program Guidance Project, B2024255, baobao shi, Fundamental Research Funds for the South-Central MinZu University, YZY24019, baobao shi

Abstract

Abstract: Phytochemical study of the EtOAc extract of Ophiorrhiza brevidentata resulted in the discovery of 10 new monoterpene indole alkaloids (1-10), along with 13 known compounds (11 - 23). Compound 1 possess an unprecedented skeleton consisting of fused 6/5/6/7/6 polycyclic systems. The structural characterization of these compounds was achieved using Nuclear Magnetic Resonance, Mass Spectrometry and Quantum Chemical Calculations. Compounds 3-5 and 9 exhibited strong inhibition on lipopolysaccharide-induced B cell proliferation with IC₅₀ values ranging from 3.6-9.1 μM with excellent selectivity indices (SI > 10).

Key words: Monoterpene indole alkaloids, ophiorrhiza brevidentata, immunological activity

摘要： Phytochemical study of the EtOAc extract of Ophiorrhiza brevidentata resulted in the discovery of 10 new monoterpene indole alkaloids (1-10), along with 13 known compounds (11 - 23). Compound 1 possess an unprecedented skeleton consisting of fused 6/5/6/7/6 polycyclic systems. The structural characterization of these compounds was achieved using Nuclear Magnetic Resonance, Mass Spectrometry and Quantum Chemical Calculations. Compounds 3-5 and 9 exhibited strong inhibition on lipopolysaccharide-induced B cell proliferation with IC₅₀ values ranging from 3.6-9.1 μM with excellent selectivity indices (SI > 10).

关键词: Monoterpene indole alkaloids, ophiorrhiza brevidentata, immunological activity

Fan Xu, Zheng-Hui Li, Meng-Lin Feng, Jia-Yu Jin, Bao-Bao Shi, Ji-Kai Liu. Monoterpene indole alkaloids from the aerial parts of Ophiorrhiza brevidentata and their immunological activities[J]. Natural Products and Bioprospecting, 2026, 16(2): 20-20.

References

[1] Wijeyesinghe S, Beura LK, Pierson MJ, Stolley JM, Adam OA, Ruscher R, et al. Expansible residence decentralizes immune homeostasis. Nature. 2021;592(7854):457.
[2] Pisetsky DS. Pathogenesis of autoimmune disease. Nat Rev Nephrol. 2023;19(8):509-24.
[3] Fugger L, Jensen LT, Rossjohn J. Challenges, progress, and prospects of developing therapies to treat autoimmune diseases. Cell. 2020;181(1):63-80.
[4] Song Y, Li J, Wu Y. Evolving understanding of autoimmune mechanisms and new therapeutic strategies of autoimmune disorders. Signal Transduct Target Ther. 2024;9(1):263.
[5] Wu Y, Huang YP, Wu Y, Sun JH, Xie QB, Yin G. Systemic immune-inflammation index as a versatile biomarker in autoimmune disorders: insights from rheumatoid arthritis, lupus, and spondyloarthritis. Front Immunol. 2025;16:1621209.
[6] Bhat R, Tonutti A, Timilsina S, Selmi C, Gershwin ME. Perspectives on mycophenolate mofetil in the management of autoimmunity. Clin Rev Allergy Immunol. 2023;65(1):86-100.
[7] Gabrielli F, Bernasconi E, Toscano A, Avossa A, Cavicchioli A, Andreone P, et al. Side effects of immunosuppressant drugs after liver transplant. Pharmaceuticals. 2025;18(3):342.
[8] Dobbels F, Moons P, Abraham I, Larsen CP, Dupont L, De Geest S. Measuring symptom experience of side-effects of immunosuppressive drugs: the modified transplant symptom occurrence and distress scale. Transpl Int. 2008;21(8):764-73.
[9] Leroy C, Rigot JM, Leroy M, Decanter C, Le Mapihan K, Parent AS, et al. Immunosuppressive drugs and fertility. Orphanet J Rare Dis. 2015;10:136.
[10] Taher M, Shaari SS, Susanti D, Arbain D, Zakaria ZA. Genus Ophiorrhiza: a review of its distribution, traditional uses, phytochemistry, biological activities and propagation. Molecules. 2020;25(11):2611.
[11] Martins D, Nunez CV. Secondary metabolites from Rubiaceae species. Molecules. 2016;20(7):13422-95.
[12] Shi BB, Ai HL, Duan KT, Feng T, Liu JK. Ophiorrhines F and G, key biogenetic intermediates of ophiorrhine alkaloids from Ophiorrhiza japonica and their immunosuppressant activities. J Nat Prod. 2022;85(2):453-7.
[13] Shi BB, Zhang GR, Li ZH, Liu JK. Three new oxygenated yohimbane-type alkaloids from Ophiorrhiza japonica. Fitoterapia. 2023;166:105442.
[14] Shi BB, Xu F, Zhang GR, He Y, Liu Q, Feng ML, et al. Glucoconjugated monoterpene indole alkaloids with xanthine oxidase inhibitory activity from Ophiorrhiza japonica. Phytochemistry. 2024;224:114169.
[15] Feng T, Duan KT, He SJ, Wu B, Zheng YS, Ai HL, et al. Ophiorrhines A and B, two immunosuppressive monoterpenoid indole alkaloids from Ophiorrhiza japonica. Org Lett. 2018;20(24):7926-8.
[16] Zhang GJ, Hu F, Jiang H, Dai LM, Liao HB, Li N, et al. Mappianines A-E, structurally diverse monoterpenoid indole alkaloids from Mappianthus iodoides. Phytochemistry. 2018;145:68-76.
[17] Rolfsen WN, Olaniyi AA, Verpoorte R, Bohlin L. Some new decussine type alkaloids from Strychnos decussata, Strychnos dale and Strychnos elaecocarpa. J Nat Prod. 1981;44(4):415-21.
[18] Kato L, de Oliveira CMA, Faria EO, Ribeiro LC, Carvalho BG, da Silva CC, et al. Antiprotozoal alkaloids from Psychotria prunifolia (Kunth) Steyerm. J Braz Chem Soc. 2012;23(2):355-60.
[19] Kutney JP, Brown RT. The structural elucidation of sitsirikine, dihydrositsirikine and isositsirikine. Three new alkaloids from Vinca rosea Linn. Tetrahedron. 1966;22(1):321-36.
[20] Levesque J, Jacquesy R, Foucher JP. Alcoyl-gluco-alcaloides: nouveaux composes isoles de pauridiantha lyalii brem (rubiacees). Tetrahedron. 1982;38(10):1417-24.
[21] Onozawa T, Kitajima M, Kogure N, Peerakam N, Santiarworn D, Takayama H. A cyclopeptide and a tetrahydroisoquinoline alkaloid from Ophiorrhiza nutans. J Nat Prod. 2017;80(7):2156-60.
[22] Kan-fan C, Zuanazzi JA, Quirion JC, Husson HP, Henriques A. Deppeaninol, a new β-carboline alkaloid from Deppea blumenaviensis (Rubiaceae). Nat Prod Res. 1995;7(4):317-21.
[23] Lin SZ, Deiana L, Tseggai A, Córdova A. Concise total synthesis of dihydrocorynanthenol, protoemetinol, protoemetine, 3-epi-Protoemetinol and emetine. Eur J Org Chem. 2012;2012(2):398-408.
[24] Brandt V, Tits M, Geerlings A, Frédérich M, Penelle J, Delaude C, et al. β-Carboline glucoalkaloids from Strychnos mellodora. Phytochemistry. 1999;51(8):1171-6.
[25] Lamidi M, Ollivier E, Mahiou V, Faure R, Debrauwer L, Nze Ekekang L, et al. Gluco-indole alkaloids from the bark of Nauclea diderrichii. ¹H and ¹³C NMR assignments of 3α-5α-tetrahydrodeoxycordifoline lactam and cadambine acid. Magn Reson Chem. 2005;43(5):427-9.
[26] Morita H, Ichihara Y, Takeya K, Watanabe K, Itokawa H, Motidome M. A new indole alkaloid glycoside from the leaves of Palicourea marcgravii. Planta Med. 1989;55(3):288-9.
[27] Zhang Z, ElSohly HN, Jacob MR, Pasco DS, Walker LA, Clark AM. New indole alkaloids from the bark of Nauclea orientalis. J Nat Prod. 2001;64(8):1001-5.
[28] Itoh A, Tanahashi T, Nagakura N, Nishi T. Two chromone-secoiridoid glycosides and three indole alkaloid glycosides from Neonauclea sessilifolia. Phytochemistry. 2003;62(3):359-69.
[29] Berger A, Kostyan MK, Klose SI, Gastegger M, Lorbeer E, Brecker L, et al. Loganin and secologanin derived tryptamine-iridoid alkaloids from Palicourea crocea and Palicourea padifolia (Rubiaceae). Phytochemistry. 2015;116:162-9.
[30] Xiao XB, Lin YX, Xu GB, Gong XB, Gu Y, Tong JF, et al. Two new cytotoxic alkaloids from Mappianthus iodoides Hand Mazz. Helv Chim Acta. 2011;94(9):1594-9.
[31] Arbain D, Putra DP, Sargent MV. The alkaloids of Ophiorrhiza filistipula. Aust J Chem. 1993;46(7):977-85.
[32] Muangrom W, Bacher M, Berger A, Valant-Vetschera K, Vajrodaya S, Schinnerl J. A novel tryptophan-derived alkaloid and other constituents from Guettarda speciosa (Rubiaceae: Cinchonoideae-Guettardeae). Biochem Syst Ecol. 2021;95:104239.
[33] Wang B, Dai Z, Liu L, Wei X, Zhu PF, Yu HF, et al. Indole glycosides from aqueous fraction of Strychnos nitida. Nat Prod Bioprospect. 2016;6(6):285-90.
[34] Cardoso CL, Siqueira Silva DH, Tomazela DM, Verli H, Young MC, Furlan M, et al. Turbinatine, a potential key intermediate in the biosynthesis of corynanthean-type indole alkaloids. J Nat Prod. 2003;66(7):1017-21.

Monoterpene indole alkaloids from the aerial parts of Ophiorrhiza brevidentata and their immunological activities

Monoterpene indole alkaloids from the aerial parts of Ophiorrhiza brevidentata and their immunological activities

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 2

Recommended Articles

Metrics

Comments

[1]	Ke-Pu Huang, Li-Li Xu, Sheng Li, Yin-Ling Wei, Lian Yang, Xiao-Jiang Hao, Hong-Ping He, Yu Zhang. Uncarialines A-E, new alkaloids from Uncaria rhynchophylla and their anticoagulant activity [J]. Natural Products and Bioprospecting, 2023, 13(2): 13-13.
[2]	Yan Deng, Mei-Fen Bao, Bao-Bao Shi, Jing Wu, Xiang-Hai Cai. Three New Indole Alkaloids from Tabernaemontana divaricata [J]. Natural Products and Bioprospecting, 2018, 8(3): 183-188.