Three new 14-noreudesmane-type sesquiterpenoids from the roots of Hippophae rhamnoides

doi:10.1007/s13659-025-00581-0

Natural Products and Bioprospecting ›› 2026, Vol. 16 ›› Issue (2): 30-30.DOI: 10.1007/s13659-025-00581-0

• ORIGINAL ARTICLES • Previous Articles

Three new 14-noreudesmane-type sesquiterpenoids from the roots of Hippophae rhamnoides

Fatima Abdurrahman Galadanchi^1,2,3, Polina Lopukhina^1,2,3, Sisi Bai^1,2,3, Guohao Dong^1,2,3, Zhongyu Zhou^1,2,3, Haihui Xie^1,2,3, Xiaoyi Wei^1,2,3

1. Guangdong Provincial Key Laboratory of Applied Botany and Key Laboratory of National Forestry and Grassland Administration On Plant Conservation and Utilization in Southern China, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, China;
2. South China National Botanical Garden, Guangzhou 510650, China;
3. University of Chinese Academy of Sciences, Beijing 100049, China

Received:2025-10-19 Online:2026-04-22 Published:2026-04-22
Contact: Zhongyu Zhou,Email:zhouzhongyu@scbg.ac.cn
Supported by:
This research was supported by the Natural Science Foundation of Guangdong Province (grant number 2025A1515010367), National Natural Science Foundation of China (grant number 31970376), and Guangdong Science and Technology Plan Project (grant number 2023B1212060046).

Three new 14-noreudesmane-type sesquiterpenoids from the roots of Hippophae rhamnoides

Fatima Abdurrahman Galadanchi^1,2,3, Polina Lopukhina^1,2,3, Sisi Bai^1,2,3, Guohao Dong^1,2,3, Zhongyu Zhou^1,2,3, Haihui Xie^1,2,3, Xiaoyi Wei^1,2,3

1. Guangdong Provincial Key Laboratory of Applied Botany and Key Laboratory of National Forestry and Grassland Administration On Plant Conservation and Utilization in Southern China, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, China;
2. South China National Botanical Garden, Guangzhou 510650, China;
3. University of Chinese Academy of Sciences, Beijing 100049, China

通讯作者: Zhongyu Zhou,Email:zhouzhongyu@scbg.ac.cn
基金资助:
This research was supported by the Natural Science Foundation of Guangdong Province (grant number 2025A1515010367), National Natural Science Foundation of China (grant number 31970376), and Guangdong Science and Technology Plan Project (grant number 2023B1212060046).

Abstract

Abstract: Hippophae rhamnoides L. (Elaeagnaceae), commonly known as sea buckthorn, is a medicinal plant valued for its diverse bioactive constituents and broad therapeutic potential. Phytochemical investigation of its roots led to the isolation of three new 14-noreudesmane-type sesquiterpenoids (1-3), together with sixteen known compounds (4-19). Their structures and absolute configurations were determined using comprehensive spectroscopic analyses and quantum chemical computations of electronic circular dichroism (ECD) spectra and ¹³C NMR shifts. Three new sesquiterpenoids (1-3) were tested for their antioxidant, anti-inflammatory, antibacterial, and α-glucosidase inhibitory activities. Unfortunately, none exhibited significant activity under the tested conditions. Among the isolated known compounds, all those displaying α-glucosidase inhibitory and antibacterial activities are pentacyclic triterpenoids. Hippophamide (17) showed significant DPPH and ABTS radical-scavenging activity. These results enriched the chemical profile of H. rhamnoides roots.

Key words: Hippophae rhamnoides, 14-noreudesmane sesquiterpenoids, Bioactivity

摘要： Hippophae rhamnoides L. (Elaeagnaceae), commonly known as sea buckthorn, is a medicinal plant valued for its diverse bioactive constituents and broad therapeutic potential. Phytochemical investigation of its roots led to the isolation of three new 14-noreudesmane-type sesquiterpenoids (1-3), together with sixteen known compounds (4-19). Their structures and absolute configurations were determined using comprehensive spectroscopic analyses and quantum chemical computations of electronic circular dichroism (ECD) spectra and ¹³C NMR shifts. Three new sesquiterpenoids (1-3) were tested for their antioxidant, anti-inflammatory, antibacterial, and α-glucosidase inhibitory activities. Unfortunately, none exhibited significant activity under the tested conditions. Among the isolated known compounds, all those displaying α-glucosidase inhibitory and antibacterial activities are pentacyclic triterpenoids. Hippophamide (17) showed significant DPPH and ABTS radical-scavenging activity. These results enriched the chemical profile of H. rhamnoides roots.

关键词: Hippophae rhamnoides, 14-noreudesmane sesquiterpenoids, Bioactivity

Fatima Abdurrahman Galadanchi, Polina Lopukhina, Sisi Bai, Guohao Dong, Zhongyu Zhou, Haihui Xie, Xiaoyi Wei. Three new 14-noreudesmane-type sesquiterpenoids from the roots of Hippophae rhamnoides[J]. Natural Products and Bioprospecting, 2026, 16(2): 30-30.

References

[1] Singh V. Global distribution of sea buckthorn (Hippophae sp) resources and their utilization. In: The Sea Buckthorn Genome. UK: Springer International Publishing; 2022.
[2] Jubayer MF, Mazumder MAR, Nayik GA, Ansari MJ, Ranganathan TV. Hippophae rhamnoides L.: Sea buckthorn. In: Immunity Boosting Medicinal Plants of the Western Himalayas. UK: Springer; 2023.
[3] Ma QG, He NX, Huang HL, Fu XM, Zhang ZL, Shu JC, et al. Hippophae rhamnoides L.: a comprehensive review on the botany, traditional uses, phytonutrients, health benefits, quality markers, and applications. J Agric Food Chem. 2023;71:4769-88.
[4] Dong W, Tang Y, Qiao J, Dong Z, Cheng J. Sea buckthorn bioactive metabolites and their pharmacological potential in digestive diseases. Front Pharmacol. 2025;16:1637676.
[5] He N, Wang Q, Huang H, Chen J, Wu G, Zhu M, et al. A comprehensive review on extraction, structure, detection, bioactivity, and metabolism of flavonoids from sea buckthorn (Hippophae rhamnoides L.). J Food Biochem. 2023;2023:4839124.
[6] Kubczak M, Khassenova AB, Skalski B, Michlewska S, Wielanek M, Sklodowska M, et al. Hippophae rhamnoides L. leaf and twig extracts as rich sources of nutrients and bioactive compounds with antioxidant activity. Sci Rep. 2022;12:1095.
[7] Ma Q, Guan Y, Sang Z, Dong J, Wei R. Isolation and characterization of auronlignan derivatives with hepatoprotective and hypolipidemic activities from the fruits of Hippophae rhamnoides L. Food Funct. 2022;13:7750-61.
[8] Lee DE, Park KH, Hong JH, Kim SH, Park KM, Kim KH. Anti-osteoporosis effects of triterpenoids from the fruit of sea buckthorn (Hippophae rhamnoides) through the promotion of osteoblast differentiation in mesenchymal stem cells, C3H10T1/2. Arch Pharm Res. 2023;46:771-81.
[9] Tkacz K, Wojdyło A, Turkiewicz IP, Nowicka P. Triterpenoids, phenolic compounds, macro-and microelements in anatomical parts of sea buckthorn (Hippophae rhamnoides L.) berries, branches and leaves. J Food Compos Anal. 2021;103:104107.
[10] Ding J, Hu N, Li G, Wang H-L. Megastigmanes and flavonoids from seeds of Hippophae rhamnoides. Chem Nat Compd. 2024;60:21-5.
[11] Hibasami H, Mitani A, Katsuzaki H, Imai K, Yoshioka K, Komiya T. Isolation of five types of flavonol from sea buckthorn (Hippophae rhamnoides) and induction of apoptosis by some of the flavonols in human promyelotic leukemia HL-60 cells. Int J Mol Med. 2005;15:805-9.
[12] Xu Y, Xu Y, Huang Z, Luo Y, Gao R, Xue J, et al. 3-pentanol glycosides from root nodules of the actinorhizal plant Alnus cremastogyne. Phytochemistry. 2023;207:113582.
[13] Jin Y, Xu Y, Huang Z, Zhou Z, Wei X. Metabolite pattern in root nodules of the actinorhizal plant Casuarina equisetifolia. Phytochemistry. 2021;186:112724.
[14] Rédei D, Kúsz N, Rafai T, Bogdanov A, Burián K, Csorba A, et al. 14-noreudesmanes and a phenylpropane heterodimer from sea buckthorn berry inhibit Herpes simplex type 2 virus replication. Tetrahedron. 2019;75:1364-70.
[15] Wolinski K, Hinton JF, Pulay P. Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. J Am Chem Soc. 1990;112:8251-60.
[16] Lodewyk MW, Soldi C, Jones PB, Olmstead MM, Rita J, Shaw JT, et al. The correct structure of aquatolide-experimental validation of a theoretically predicted structural revision. J Am Chem Soc. 2012;134:18550-3.
[17] Ditchfield R. Self-consistent perturbation theory of diamagnetism: I. a gauge-invariant LCAO method for NMR chemical shifts. Mol Phys. 1974;27:789-807.
[18] Ditchfield R. Molecular orbital theory of magnetic shielding and magnetic susceptibility. J Chem Phys. 1972;56:5688-91.
[19] Smith SG, Goodman JM. Assigning stereochemistry to single diastereoisomers by GIAO NMR calculation: the DP4 probability. J Am Chem Soc. 2010;132:12946-59.
[20] Grimblat N, Zanardi MM, Sarotti AM. Beyond DP4: an improved probability for the stereochemical assignment of isomeric compounds using quantum chemical calculations of NMR shifts. J Org Chem. 2015;80:12526-34.
[21] Zhang XL, Na HY, Li PS, Chen YX, Li ZL, Liang GD, et al. Hipponorterpenes A and B, two new 14-noreudesmane-type sesquiterpenoids from the juice of Hippophae rhamnoides. Phytochem Lett. 2022;52:82-6.
[22] Yang CY, Geng CA, Huang XY, Wang H, Xu HB, Liang WJ, et al. Noreudesmane sesquiterpenoids from the leaves of Nicotiana tabacum. Fitoterapia. 2014;96:81-7.
[23] Park DH, Lee JW, Jin Q, Jeon WK, Lee MK, Hwang BY. A new noreudesmane-type sesquiterpenoid from Alpinia oxyphylla. Bull Korean Chem Soc. 2014;35:1565-7.
[24] Kuhnert E, Surup F, Wiebach V, Bernecker S, Stadler M. Botryane, noreudesmane and abietane terpenoids from the ascomycete Hypoxylon rickii. Phytochemistry. 2015;117:116-22.
[25] Tao Q, Ma K, Yang Y, Wang K, Chen B, Huang Y, et al. Bioactive sesquiterpenes from the edible mushroom Flammulina velutipes and their biosynthetic pathway confirmed by genome analysis and chemical evidence. J Org Chem. 2016;81:9867-77.
[26] Ramesh AS, Christopher JG, Radhika R, Setty CR, Thankamani V. Isolation, characterisation and cytotoxicity study of arjunolic acid from Terminalia arjuna. Nat Prod Res. 2012;26:1549-52.
[27] Wang F, Li ZL, Cui HH, Hua HM, Jing YK, Liang SW. Two new triterpenoids from the resin of Boswellia carterii. J Asian Nat Prod Res. 2011;13:193-7.
[28] Kamiya K, Yoshioka K, Saiki Y, Ikutat A, Satak T. Triterpenoids and flavonoids from Paeonia lactiflora. Phytochemistry. 1997;44:141-4.
[29] Xia M, Tan J, Yang L, Shang Z, Zhao Q, Shi G. Studies on chemical constituents in Patrinia scabiosaefolia. Chin Tradit Herbal Drugs. 2010;41:1612-5.
[30] Osman W, Ibrahim M, Adam M, Mothana R, Mohammed M, Abdoon I, et al. Isolation and characterization of four terpenoidal compounds with potential antimicrobial activity from Tarconanthus camphorantus L. (Asteraceae). J Pharm Bioallied Sci. 2019;11:373-9.
[31] Castellano JM, Sara RR, Perona JS. Oleanolic acid: extraction, characterization and biological activity. Nutrients. 2022;14:623.
[32] Gnoatto SC, Klimpt AD, Nascimento SD, Galera P, Boumediene K, Gosmann G, et al. Evaluation of ursolic acid isolated from Ilex paraguariensis and derivatives on aromatase inhibition. Eur J Med Chem. 2008;43:1865-77.
[33] Murakami C, Myoga K, Kasai R, Ohtani K, Kurokawa T, Ishibashi S, et al. Screening of plant constituents for effect on glucose transport activity in Ehrlich ascites tumour cells. Chem Pharm Bull. 1993;41:2129-31.
[34] Kwon HC, Zee SD, Cho SY, Chop SU, Lee KR. Cytotoxic ergosterols from Paecilomyces sp. J300. Arch Pharm Res. 2002;25:851-5.
[35] Jibril S, Sirat HM, Zakari A, Sani IM, Kendeson CA, Abdullahi Z, et al. Isolation of chemical constituents from n-hexane leaf extract of Cassia singueana del. (Fabaceae). Chem Search J. 2019;10:14-20.
[36] Ododo MM, Choudhury MK, Dekebo AH. Structure elucidation of β-sitosterol with antibacterial activity from the root bark of Malva parviflora. Springerplus. 2016;5:1-11.
[37] Zhimin L, Lijun W, Bingya J, Bohang S, Huang J, Huiyuan G. Chemical constituents of chestnut kernel (III). J Shenyang Pharm Univ. 2008;25:856.
[38] Zhu XD, Xu B, Wang F. Studies on the chemical components of Osyris wightiana. Nat Prod Res Dev. 2009;21:956-9.
[39] OuYang J, Zhou WN, Li G, Wang XY, Ding CX, Suo YR, et al. Three new alkaloids from Hippophae rhamnoides Linn. subsp. sinensis Rousi. Helv Chim Acta. 2015;98:1287-91.
[40] Guangshu W, Muxin Z, Xiaohong Y, Jingda X. Studies on the non-alkaloid constituents of Hippeastrun vittatum in Amaryllidaceae. Chin Pharm J. 2005;40:498-9.
[41] Wang Yan WY, Su BingHe SB, Zhou XiaoYu ZX, Wang TianMin WT, Zhai YanJun ZY. Study on chemical constituents of processed fructus Polygoni orientalis. Liaoning J Tradit Chin Med. 2012;39:505-8.
[42] Gaussian 09, revision D.01. 2013, Gaussian, Inc.: Wallingford CT.
[43] Neese F. Software update: the ORCA program system, version 4.0. WIRES Comput Mol Sci. 2018;8:e1327.
[44] Becke AD. Density-functional thermochemistry III. The role of exact exchange. J Chem Phys. 1993;98:5648-52.
[45] Lee CT, Yang WT, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B. 1988;37:785-9.
[46] Grimme S, Antony J, Ehrlich S, Krieg H. A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J Chem Phys. 2010;132:154104.
[47] Grimme S, Ehrlich S, Goerigk L. Effect of the damping function in dispersion corrected density functional theory. J Comput Chem. 2011;32:1456-65.
[48] Goerigk L, Grimme S. Efficient and accurate Double-Hybrid-Meta-GGA density functionals evaluation with the extended GMTKN30 database for general main group thermochemistry, kinetics, and noncovalent interactions. J Chem Theory Comput. 2011;7:291-309.
[49] Weigend F, Ahlrichs R. Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: design and assessment of accuracy. Phys Chem Chem Phys. 2005;7:3297-305.
[50] Marenich AV, Cramer CJ, Truhlar DG. Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J Phys Chem B. 2009;113:6378-96.
[51] Chen G, Wang Y, Zhao C, Korpelainen H, Li C. Genetic diversity of Hippophae rhamnoides populations at varying altitudes in the Wolong natural reserve of China as revealed by ISSR markers. Silvae Genet. 2008;57:29.
[52] Perdew JP, Burke K, Ernzerhof M. Generalized gradient approximation made simple. Phys Rev Lett. 1996;77:3865-8.
[53] Peverati R, Truhlar DG. M11-L: a local density functional that provides improved accuracy for electronic structure calculations in chemistry and physics. J Phys Chem Lett. 2012;3:117-24.
[54] Perdew JP, Ruzsinszky A, Csonka GI, Constantin LA, Sun JW. Workhorse semilocal density functional for condensed matter physics and quantum chemistry. Phys Rev Lett. 2009;103:026403.
[55] Bruhn T, Schaumloeffel A, Hemberger Y, Bringmann G. SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality. 2013;25:243-9.
[56] Ma Q, Xie H, Li S, Zhang R, Zhang M, Wei X. Flavonoids from the pericarps of Litchi chinensis. J Agric Food Chem. 2014;62:1073-8.
[57] Cheng XL, Li HX, Chen J, Wu P, Xue JH, Zhou ZY, et al. Bioactive diarylheptanoids from Alpinia coriandriodora. Nat Prod Bioprospect. 2021;11:63-72.
[58] Liu SB, Zeng L, Xu QL, Chen YL, Lou T, Zhang SX, et al. Polycyclic phenol derivatives from the leaves of Spermacoce latifolia and their antibacterial and α-glucosidase inhibitory activity. Molecules. 2022;27:3334.

Three new 14-noreudesmane-type sesquiterpenoids from the roots of Hippophae rhamnoides

Three new 14-noreudesmane-type sesquiterpenoids from the roots of Hippophae rhamnoides

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