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Minor diterpene glycosides from the leaves of Stevia rebaudiana.
J Nat Prod. 2014 May 23; 77(5):1231-5.JN

Abstract

Two new diterpene glycosides in addition to five known glycosides have been isolated from a commercial extract of the leaves of Stevia rebaudiana. Compound 1 (rebaudioside KA) was shown to be 13-[(O-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid 2-O-β-d-glucopyranosyl-β-d-glucopyranosyl ester and compound 2, 12-α-[(2-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid β-d-glucopyranosyl ester. Five additional known compounds were identified, rebaudioside E, rebaudioside M, rebaudioside N, rebaudioside O, and stevioside, respectively. Enzymatic hydrolysis of stevioside afforded the known ent-kaurane aglycone 13-hydroxy-ent-kaur-16-en-19-oic acid (steviol) (3). The isolated metabolite 1 possesses the ent-kaurane aglycone steviol (3), while compound 2 represents the first example of the isomeric diterpene 12-α-hydroxy-ent-kaur-16-en-19-oic acid existing as a glycoside in S. rebaudiana. The structures of the isolated metabolites 1 and 2 were determined based on comprehensive 1D- and 2D-NMR (COSY, HSQC, and HMBC) studies. A high-quality crystal of compound 3 has formed, which allowed the acquisition of X-ray diffraction data that confirmed its structure. The structural similarities between the new metabolites and the commercially available stevioside sweeteners suggest the newly isolated metabolites should be examined for their organoleptic properties. Accordingly rebaudiosides E, M, N, O, and KA have been isolated in greater than gram quantities.

Authors+Show Affiliations

Ironstone Separations, Inc. , Etta, Mississippi 38627, United States.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24758242

Citation

Ibrahim, Mohamed A., et al. "Minor Diterpene Glycosides From the Leaves of Stevia Rebaudiana." Journal of Natural Products, vol. 77, no. 5, 2014, pp. 1231-5.
Ibrahim MA, Rodenburg DL, Alves K, et al. Minor diterpene glycosides from the leaves of Stevia rebaudiana. J Nat Prod. 2014;77(5):1231-5.
Ibrahim, M. A., Rodenburg, D. L., Alves, K., Fronczek, F. R., McChesney, J. D., Wu, C., Nettles, B. J., Venkataraman, S. K., & Jaksch, F. (2014). Minor diterpene glycosides from the leaves of Stevia rebaudiana. Journal of Natural Products, 77(5), 1231-5. https://doi.org/10.1021/np4009656
Ibrahim MA, et al. Minor Diterpene Glycosides From the Leaves of Stevia Rebaudiana. J Nat Prod. 2014 May 23;77(5):1231-5. PubMed PMID: 24758242.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Minor diterpene glycosides from the leaves of Stevia rebaudiana. AU - Ibrahim,Mohamed A, AU - Rodenburg,Douglas L, AU - Alves,Kamilla, AU - Fronczek,Frank R, AU - McChesney,James D, AU - Wu,Chongming, AU - Nettles,Brian J, AU - Venkataraman,Sylesh K, AU - Jaksch,Frank, Y1 - 2014/04/23/ PY - 2014/4/25/entrez PY - 2014/4/25/pubmed PY - 2014/10/1/medline SP - 1231 EP - 5 JF - Journal of natural products JO - J Nat Prod VL - 77 IS - 5 N2 - Two new diterpene glycosides in addition to five known glycosides have been isolated from a commercial extract of the leaves of Stevia rebaudiana. Compound 1 (rebaudioside KA) was shown to be 13-[(O-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid 2-O-β-d-glucopyranosyl-β-d-glucopyranosyl ester and compound 2, 12-α-[(2-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy]ent-kaur-16-en-19-oic acid β-d-glucopyranosyl ester. Five additional known compounds were identified, rebaudioside E, rebaudioside M, rebaudioside N, rebaudioside O, and stevioside, respectively. Enzymatic hydrolysis of stevioside afforded the known ent-kaurane aglycone 13-hydroxy-ent-kaur-16-en-19-oic acid (steviol) (3). The isolated metabolite 1 possesses the ent-kaurane aglycone steviol (3), while compound 2 represents the first example of the isomeric diterpene 12-α-hydroxy-ent-kaur-16-en-19-oic acid existing as a glycoside in S. rebaudiana. The structures of the isolated metabolites 1 and 2 were determined based on comprehensive 1D- and 2D-NMR (COSY, HSQC, and HMBC) studies. A high-quality crystal of compound 3 has formed, which allowed the acquisition of X-ray diffraction data that confirmed its structure. The structural similarities between the new metabolites and the commercially available stevioside sweeteners suggest the newly isolated metabolites should be examined for their organoleptic properties. Accordingly rebaudiosides E, M, N, O, and KA have been isolated in greater than gram quantities. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/24758242/Minor_diterpene_glycosides_from_the_leaves_of_Stevia_rebaudiana_ DB - PRIME DP - Unbound Medicine ER -