New phenylbutenoids and terpene glycosides from Ginkgo biloba leaves

Zeshi SUN , Shan LIN , Zhi-Li WU , Hong-Yuan DONG , Xi-Ke XU , Hui-Liang LI , Jinxin WANG

Chinese Journal of Natural Medicines ›› 2024, Vol. 22 ›› Issue (2) : 161 -170.

PDF (1216KB)
Chinese Journal of Natural Medicines ›› 2024, Vol. 22 ›› Issue (2) :161 -170. DOI: 10.1016/S1875-5364(24)60588-1
Original article
research-article
New phenylbutenoids and terpene glycosides from Ginkgo biloba leaves
Author information +
History +
PDF (1216KB)

Abstract

Our continued works on the chemical constituents of Ginkgo biloba (G. biloba) leaves has led to the isolation of two novel phenylbutenoids (1, 2), along with five previously unidentified terpene glycosides (37). Among them, compounds 1 and 2 represent unique (Z)-phenylbutenoids, 36 are megastigmane glycosides, and 7 is identified as a rare bilobanone glycoside (Fig. 1). This study marks the first reported isolation of phenylbutenoid and bilobanone glycoside from G. biloba. The chemical structures of these compounds were elucidated through extensive spectroscopic analysis, including HR-ESI-MS and various 1D and 2D NMR experiments. Furthermore, the absolute configurations of these molecules were determined using Mosher’s method, ECD experiments, and Cu-Kα X-ray crystallographic analyses.

Keywords

Ginkgo biloba / Phenylbutenoid / Megastigmane glycoside / Bilobanone glycoside

Cite this article

Download citation ▾
Zeshi SUN, Shan LIN, Zhi-Li WU, Hong-Yuan DONG, Xi-Ke XU, Hui-Liang LI, Jinxin WANG. New phenylbutenoids and terpene glycosides from Ginkgo biloba leaves. Chinese Journal of Natural Medicines, 2024, 22(2): 161-170 DOI:10.1016/S1875-5364(24)60588-1

登录浏览全文

4963

注册一个新账户 忘记密码

References

[1]

Banin RM, Hirata BKS, Andrade IS, et al. Beneficial effects of Ginkgo biloba extract on insulin signaling cascade, dyslipidemia, and body adiposity of diet-induced obese rats[J]. Braz J Med Biol Res, 2014, 47(9): 780-788.

[2]

Eisvand F, Razavi BM, Hosseinzadeh H. The effects of Ginkgo biloba on metabolic syndrome: a review[J]. Phytother Res, 2020, 34(8): 1798-1811.

[3]

Singh SK, Srivastav S, Castellani RJ, et al. Neuroprotective and antioxidant effect of Ginkgo biloba extract against AD and other neurological disorders[J]. Neurotherapeutics, 2019, 16(3): 666-674.

[4]

Dong W, Zhao S, Wen S, et al. A preclinical randomized controlled study of ischemia treated with Ginkgo biloba extracts: are complex components beneficial for treating acute stroke[J]. Curr Res Transl Med, 2020, 68(4): 197-203.

[5]

Ji H, Zhou X, Wei W, et al. Ginkgol biloba extract as an adjunctive treatment for ischemic stroke: a systematic review and meta-analysis of randomized clinical trials[J]. Medicine, 2020, 99(2): e18568.

[6]

Liu L, Wang Y, Zhang J, et al. Advances in the chemical constituents and chemical analysis of Ginkgo biloba leaf, extract, and phytopharmaceuticals[J]. J Pharm Biomed Anal, 2021, 193: 113704.

[7]

Wang X, Gong X, Zhang H, et al. In vitro anti-aging activities of Ginkgo biloba leaf extract and its chemical constituents[J]. Food Sci Technol, 2020, 40: 476-482.

[8]

Dong HL, Lin S, Wu QL, et al. A new bilobalide isomer and two cis-coumaroylated flavonol glycosides from Ginkgo biloba leaves[J]. Fitoterapia, 2020, 142: 104516.

[9]

Yu H, Dong LH, Zhang Y, et al. A network pharmacology-based strategy for predicting the protective mechanism of Ginkgo biloba on damaged retinal ganglion cells[J]. Chin J Nat Med, 2022, 20(1): 54-66.

[10]

Okhti ZA, Abdalah ME, Hanna DB. Phytochemical structure and biological effect of Ginkgo biloba leaves: a review[J]. Int J Pharm Res, 2021, 13(2): 1138-1143.

[11]

Akiba S, Chiba M, Mukaida Y, et al. The leaf extract of Ginkgo biloba L. suppresses oxidized LDL-stimulated fibronectin production through an antioxidant action in rat mesangial cells[J]. Br J Pharmacol, 2004, 142(3): 419-424.

[12]

Mashayekh A, Pham DL, Yousem DM, et al. Effects of Ginkgo biloba on cerebral blood flow assessed by quantitative MR perfusion imaging: a pilot study[J]. Neuroradiology, 2011, 53(3): 185-191.

[13]

Shinozuka K, Umegaki K, Kubota Y, et al. Feeding of Ginkgo biloba extract (GBE) enhances gene expression of hepatic cytochrome P-450 and attenuates the hypotensive effect of nicardipine in rats [J]. Life Sci, 2002, 70( 23): 2783-2792.

[14]

Naik SR, Panda VS. Antioxidant and hepatoprotective effects of Ginkgo biloba phytosomes in carbon tetrachloride-induced liver injury in rodents[J]. Liver Int, 2007, 27(3): 393-399.

[15]

Cho KS, Lee IM, Sim S, et al. Ginkgo biloba extract ( EGb 761®) inhibits glutamate-induced up-regulation of tissue plasminogen activator through inhibition of c-Fos translocation in rat primary cortical neurons[J]. Phytother Res, 2016, 30(1): 58-65.

[16]

Liu XG, Lu X, Gao W, et al. Structure, synthesis, biosynthesis,and activity of the characteristic compounds from Ginkgo biloba L.[J]. Nat Prod Rep, 2022, 39: 474-511.

[17]

Ude C, Schubert-Zsilavecz M, Wurglics M. Ginkgo biloba extracts: a review of the pharmacokinetics of the active ingredients[J]. Clin Pharmacokinet, 2013, 52(9): 727-749.

[18]

Wu Z, Wang Q, Fu L, et al. Vlasoulides A and B, a pair of neuroprotective C32 dimeric sesquiterpenes with a hexacyclic 5/7/5/5/(5)/7 carbon skeleton from the roots of Vladimiria souliei[J]. RSC Adv, 2021, 11(11): 6159-6162.

[19]

Seo S, Tomita Y, Tori K, et al. Determination of the absolute configuration of a secondary hydroxy group in a chiral secondary alcohol using glycosidation shifts in carbon-13 nuclear magnetic resonance spectroscopy[J]. J Am Chem Soc, 1978, 100(11): 3331-3339.

[20]

Kasai R, Suzuo M, Asakawa J, et al. Carbon-13 chemical shifts of isoprenoid-β-D-glucopyranosides and -β-D-mannopyranosides. Stereochemical influences of aglycones alcohols[J]. Tetrahedron Lett, 1977, 18(2): 175-178.

[21]

Yamano Y, Ito M. Synthesis of optically active vomifoliol and roseoside stereoisomers[J]. Chem Pharm Bull, 2005, 53(5): 541-546.

[22]

Yamano Y, Shimizu Y, Ito M. Stereoselective synthesis of optically active 3-hydroxy-7,8-dihydro-β-ionol-glucosides[J]. Chem Pharm Bull, 2003, 51(7): 878-882.

[23]

Shu P, Wei X, Xue Y, et al. Wilsonols A-L, megastigmane sesquiterpenoids from the leaves of Cinnamomum wilsonii[J]. J Nat Prod, 2013, 76(7): 1303-1312.

[24]

Wang Y, Zhao B, Ma HR, et al. Two new sesquiterpenoid glycosides from the leaves of Lycium barbarum[J]. J Asian Nat Prod Res, 2016, 18(9): 871-877.

Funding

National Natural Science Foundation of China(82141203)

National Natural Science Foundation of China(82003624)

National Natural Science Foundation of China(82004003)

National Natural Science Foundation of China(82004215)

Science and Technology Commission of Shanghai Municipality(20YF1458700)

Science and Technology Commission of Shanghai Municipality(20YF1459000)

Innovation Team and Talents Cultivation Program of National Administration of Traditional Chinese Medicine(ZYYCXTDD-202004)

Shanghai Frontiers Science Center of TCM Chemical Biology, Shanghai Engineering Research Center for the Preparation of Bioactive Natural Products(16DZ2280200)

PDF (1216KB)

0

Accesses

0

Citation

Detail

Sections
Recommended

/