Top

Published in:

01-04-2016 | Original Paper

Acylated neo-clerodane type diterpenoids from the aerial parts of Scutellaria coleifolia Levl. (Lamiaceae)

Authors: Shin-ichiro Kurimoto, Jian-Xin Pu, Han-Dong Sun, Hirofumi Shibata, Yoshihisa Takaishi, Yoshiki Kashiwada

Published in: Journal of Natural Medicines | Issue 2/2016

Abstract

Twenty new neo-clerodane type diterpenoids, scutefolides G₁-S (1–20), were isolated from the 70 % aqueous acetone extract of the aerial parts of Scutellaria coleifolia. Their structures were elucidated by extensive spectroscopic analyses. The absolute configurations of 1, 2, 7, 8, 14 and 15 were determined by means of the CD exciton chirality method. Compounds 1, 2, 5, 7, 8, 12, 14, 15, 18 and 19 were evaluated for their cytotoxic activities against four human cancer cell lines, and anti-bacterial activities against methicillin-resistant Staphylococcus aureus.

Shang X, He X, He X, Li M, Zhang R, Fan P, Zhang Q, Jia Z (2010) The genus Scutellaria an ethnopharmacological and phytochemical review. J Ethnopahrmacol 128:279–313CrossRef

Ministry of Health (2011) Labour and Welfare of Japan (in Japanese). The Japanese Pharmacopoeia, 16th edn. Tokyo

Pharmacopoeia Commission Ministry of Public Health (2000) Pharmacopoeia of the People’s Republic in China. Part 1 (in Chinese). Beijing

Wang TS, Wang SQ, Xiao DL (2012) A review of phytochemistry and antitumor activity of a valuable medicinal species: Scutellaria barbata. J Med Plants Res 6:4259–4275

Kurimoto S, Pu JX, Sun HD, Takaishi Y, Kashiwada Y (2015) Coleifolides A and B, two new sesterterpenoids from the aerial parts of Scutellaria cleifolia Levl. Chem Biodivers 12:1200–1207CrossRefPubMed

Kurimoto S, Pu JX, Sun HD, Takaishi Y, Kashiwada Y (2015) Acylated neo-clerodanes and 19-nor-neo-clerodanes from the aerial parts of Scutellaria coleifolia (Lamiaceae). Phytochemistry 116:298–304CrossRefPubMed

Bozov PI, Malakov PY, Papanov GY, de la Torre MC, Rodríguez B, Perales A (1993) Scutalpin A, a neo-clerodane diterpene from Scutellaria alpina. Phytochemistry 34:453–456CrossRef

Lin YL, Kuo YL (1989) Four new neoclerodane-type diterpenoids, scutellones B, G, H, and I, from aerial parts of Scutellaria rivularis. Chem Pharm Bull 37:582–585CrossRef

de la Torre MC, Rodríguez B, Bruno M, Piozzi F, Savona G, Vassallo N, Servettaz O (1995) Neo-Clerodane diterpenoids from Scutellaria alpina. Phytochemistry 38:181–187CrossRef

10.

Malakov PY, Papanov GY (1996) Neo-clerodane diterpenoids from Scutellaria orientalis subsp. pinnatifida. Phytochemistry 43:173–178CrossRef

11.

Kizu H, Imoto Y, Tomimori T, Kikuchi T, Kadota S, Tsubono K (1997) Studies on the constituents of Scutellaria species. XVIII. Structures of neoclerodane-type diterpenoids from the whole herb of Scutellaria rivularis Wall. Chem Pharm Bull 45:152–160CrossRef

12.

Muñoz DM, de la Torre MC, Rodríguez B, Simmonds MSJ, Blaney WM (1997) Neo-clerodane insect antifeedants from Scutellaria alpina subsp. javalambrensis. Phytochemistry 44:593–597CrossRef

13.

Esquivel B, Domínguez RM, Toscano RA (2001) Neoclerodane diterpenoids from Scutellaria caerulea. J Nat Prod 64:778–782CrossRefPubMed

14.

Nguyen VH, Pham VC, Nguyen TTH, Tran VH, Doan TMH (2009) Novel antioxidant neo-clerodane diterpenoids from Scutellaria barbata. Eur J Org Chem 2009:5810–5815CrossRef

15.

Lee H, Kim Y, Choi I, Min BS, Shim SH (2010) Two novel neo-clerodane diterpenoids from Scutellaria barbata. Bioorg Med Chem Lett 20:288–290CrossRefPubMed

16.

Zhu F, Di YT, Liu LL, Zhang Q, Fang Q, Yang TQ, Hao XJ, He HP (2010) Cytotoxic neoclerodane diterpenoids from Scutellaria barbata. J Nat Prod 73:233–236CrossRefPubMed

17.

Nie XP, Qu GW, Yue XD, Li GS, Dai SJ (2010) Scutelinquanines A–C, three new cytotoxic neo-clerodane diterpenoid from Scutellaria barbata. Phytochem Lett 3:190–193CrossRef

18.

Wang F, Ren FC, Li YJ, Liu JK (2010) Scutebarbatines W–Z, new neo-clerodane diterpenoids from Scutellaria barbata and structure revision of a series of 13-spiro neo-clerodanes. Chem Pharm Bull 58:1267–1270CrossRefPubMed

19.

Raccuglia RA, Bellone G, Loziene K, Piozzi F, Rosselli S, Maggio A, Bruno M, Simmonds MSJ (2010) Hastifolins A–G, antifeedant neo-clerodane diterpenoids from Scutellaria hastifolia. Phytochemistry 71:2087–2091CrossRefPubMed

20.

Lee H, Shim SH (2011) neo-Clerodane diterpenoids from the aerial parts of Scutellaria barbata. Helv Chim Acta 94:643–649CrossRef

21.

Dai SJ, Peng WB, Zhang DW, Shen L, Wang WY, Ren Y (2009) J Nat Prod 72:1793–1797CrossRefPubMed

22.

Dai SJ, Tao JY, Liu K, Jiang YT, Shen L (2006) neo-Clerodane diterpenoids from Scutellaria barbata with cytotoxic activities. Phytochemistry 67:1326–1330CrossRefPubMed

23.

Miyaichi Y, Kizu H, Yamaguchi Y, Tomimori T (1994) Studies on the constituents of Scutellaria spices. XV. On the diterpenoid constituents of the leaves of Scutellaria alpina L. Yakugaku Zasshi 114:264–271PubMed

24.

Hussein AA, de la Torre MC, Jimeno ML, Rodríguez B, Bruno M, Piozzi F, Servettaz O (1996) A neo-clerodane diterpenoids from Scutellaria baicalensis. Phytochemistry 43:835–837CrossRef

25.

de la Torre MC, Rodríguez B, Bruno M, Vassallo N, Bondì ML, Piozzi F, Servettaz O (1997) Neoclerodane diterpenoids from Scutellaria polyodon. J Nat Prod 60:1229–1235CrossRef

26.

Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55–63CrossRefPubMed

27.

Shibata H, Kondo K, Katsuyama R, Kawazoe K, Sato Y, Murakami K, Takaishi Y, Arakaki N, Higuti T (2005) Alkyl gallates, intensifiers of β-lactam susceptibility in methicillin-resistant Staphylococcus aureus. Antimicrob Agents Chemother 49:549–555PubMedCentralCrossRefPubMed

Title: Acylated neo-clerodane type diterpenoids from the aerial parts of Scutellaria coleifolia Levl. (Lamiaceae)
Authors: Shin-ichiro Kurimoto
Jian-Xin Pu
Han-Dong Sun
Hirofumi Shibata
Yoshihisa Takaishi
Yoshiki Kashiwada
Publication date: 01-04-2016
Publisher: Springer Japan
Published in: Journal of Natural Medicines / Issue 2/2016
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-016-0967-3

Keynote webinar | Spotlight on medication adherence

Springer Medicine

Acylated neo-clerodane type diterpenoids from the aerial parts of Scutellaria coleifolia Levl. (Lamiaceae)

Abstract

Keynote webinar | Spotlight on medication adherence

Springer Medicine

Abstract

Please log in to get access to this content

Other articles of this Issue 2/2016

In vitro and in vivo antiherpetic effects of (1R,2R)-1-(5′-methylful-3′-yl)propane-1,2,3-triol

Erratum to: LC-MS-based quantification method for Achyranthes root saponins

Anti-osteoporotic effects of Pueraria candollei var. mirifica on bone mineral density and histomorphometry in estrogen-deficient rats

Investigation of sedative and hypnotic effects of Amygdalus communis L. extract: behavioral assessments and EEG studies on rat

Two new bicyclic sulfoxides from Welsh onion

Three new xanthones from the leaves of Garcinia lancilimba