Skip to main content
Top
Published in: Journal of Natural Medicines 1/2008

01-01-2008 | Original Paper

Two new lignan glucosides from the fruit of Vitex cannabifolia

Authors: Toru Yamasaki, Tetsuro Kawabata, Chikako Masuoka, Junei Kinjo, Tsuyoshi Ikeda, Toshihiro Nohara, Masateru Ono

Published in: Journal of Natural Medicines | Issue 1/2008

Login to get access

Abstract

Two new phenyldihydronaphthalene-type lignan glucosides, vitecannasides A (1) and B (2) were isolated from the fruit of Vitex cannabifolia Sieb. et. Zucc. (Verbenaceae) along with the six known lignan derivatives (38), four known iridoid glucosides (912), three known flavonoids (1315), and one known phenylbutanone glucoside (16). Their chemical structures were determined on the basis of spectroscopic data as well as chemical evidence. The scavenging effect of 1, 2, and 1116 on the stable free radical 1,1-diphenyl-2-picrylhydrazyl was examined. Compounds 1, 2, 14, and 15 exhibited stronger activity than that of l-cysteine. Especially, 14 and 15 showed more potent activity than that of α-tocopherol.
Literature
1.
go back to reference Mitsuru H, Ogata K, Nitta A, Hoshikawa K, Yanagi M, Yamazaki K (1989) Useful plants of the world. Heibonsha Ltd., Japan, p 1099 Mitsuru H, Ogata K, Nitta A, Hoshikawa K, Yanagi M, Yamazaki K (1989) Useful plants of the world. Heibonsha Ltd., Japan, p 1099
2.
go back to reference Taguchi H (1976) Studies on the constituents of Vitex cannabifolia. Chem Pharm Bull 24:1668–1670 Taguchi H (1976) Studies on the constituents of Vitex cannabifolia. Chem Pharm Bull 24:1668–1670
3.
go back to reference Iwagawa T, Nakahara A, Nakatani M (1993) Iridoids from Vitex cannabifolia. Phytochemistry 32:453–454CrossRef Iwagawa T, Nakahara A, Nakatani M (1993) Iridoids from Vitex cannabifolia. Phytochemistry 32:453–454CrossRef
4.
go back to reference Ono M, Oishi H, Abe H, Masuoka C, Okawa M, Ikeda T, Nohara T (2006) New iridoid glucosides from the aerial parts of Verbena brasiliensis. Chem Pharm Bull 54:1421–1424PubMedCrossRef Ono M, Oishi H, Abe H, Masuoka C, Okawa M, Ikeda T, Nohara T (2006) New iridoid glucosides from the aerial parts of Verbena brasiliensis. Chem Pharm Bull 54:1421–1424PubMedCrossRef
5.
go back to reference Ono M, Nishida Y, Masuoka C, Li J, Okawa M, Ikeda T, Nohara T (2004) Lignan derivatives and a norditerpene from the seeds of Vitex negundo. J Nat Prod 67:2073–2075PubMedCrossRef Ono M, Nishida Y, Masuoka C, Li J, Okawa M, Ikeda T, Nohara T (2004) Lignan derivatives and a norditerpene from the seeds of Vitex negundo. J Nat Prod 67:2073–2075PubMedCrossRef
6.
go back to reference Chawla AS, Sharma AK, Handa SS, Dhar KL (1992) A lignan from Vitex negundo seeds. Phytochemistry 31:4378–4379CrossRef Chawla AS, Sharma AK, Handa SS, Dhar KL (1992) A lignan from Vitex negundo seeds. Phytochemistry 31:4378–4379CrossRef
7.
go back to reference Kawazoe K, Yutani A, Tamemoto K, Yuasa S, Shibata H, Higuti T, Takaishi Y (2001) Phenylnaphtalene compounds from the subterranean parts of Vitex rotundifolia and their antibacterial activity against methicillin-resistant Staphylococcus aureus. J Nat Prod 64:588–591PubMedCrossRef Kawazoe K, Yutani A, Tamemoto K, Yuasa S, Shibata H, Higuti T, Takaishi Y (2001) Phenylnaphtalene compounds from the subterranean parts of Vitex rotundifolia and their antibacterial activity against methicillin-resistant Staphylococcus aureus. J Nat Prod 64:588–591PubMedCrossRef
8.
go back to reference Ono M, Masuoka C, Odake Y, Ikegashira S, Ito Y, Nohara T (2000) Antioxidative constituents from Tessaria integrifolia. Food Sci Technol Res 6:106–114CrossRef Ono M, Masuoka C, Odake Y, Ikegashira S, Ito Y, Nohara T (2000) Antioxidative constituents from Tessaria integrifolia. Food Sci Technol Res 6:106–114CrossRef
9.
go back to reference Dutta PK, Chowdhury US, Chakravarty AK, Achari B, Pakrashi SC (1983) Studies on Indian medical plants-part LXXV Nishindaside, a novel iridoid glycoside from Vitex negundo. Tetrahedron 39:3067–3072CrossRef Dutta PK, Chowdhury US, Chakravarty AK, Achari B, Pakrashi SC (1983) Studies on Indian medical plants-part LXXV Nishindaside, a novel iridoid glycoside from Vitex negundo. Tetrahedron 39:3067–3072CrossRef
10.
go back to reference Ono M, Ito Y, Kubo S, Nohara T (1997) Two new iridoids from Vitcis trifoliae Fructus (fruit of Vitex rotundifolia L.). Chem Pharm Bull 45:1094–1097 Ono M, Ito Y, Kubo S, Nohara T (1997) Two new iridoids from Vitcis trifoliae Fructus (fruit of Vitex rotundifolia L.). Chem Pharm Bull 45:1094–1097
11.
go back to reference Ono M, Ueno M, Masuoka C, Ikeda T, Nohara T (2005) Iridoid glucosides from the fruit of Genipa americana. Chem Pharm Bull 53:1342–1344PubMedCrossRef Ono M, Ueno M, Masuoka C, Ikeda T, Nohara T (2005) Iridoid glucosides from the fruit of Genipa americana. Chem Pharm Bull 53:1342–1344PubMedCrossRef
12.
go back to reference Roitman JN, James LF (1985) Chemistry of toxic range plants. Highly oxygenated flavonol methyl ethers from Gutierrezia microcephala. Phytochemistry 24:835–848CrossRef Roitman JN, James LF (1985) Chemistry of toxic range plants. Highly oxygenated flavonol methyl ethers from Gutierrezia microcephala. Phytochemistry 24:835–848CrossRef
13.
go back to reference Harbone JB, Marbry TJ (1982) The flavonoids: advances in research. Chapman and Hall, New York, p 74 Harbone JB, Marbry TJ (1982) The flavonoids: advances in research. Chapman and Hall, New York, p 74
14.
go back to reference Fujita M, Inoue T, Nagai M (1985) O-Methylation effect on the cabon-13 nuclear magnetic resonance signals of ortho-substituted phenols. II. Yakugaku Zasshi 105:140–248 Fujita M, Inoue T, Nagai M (1985) O-Methylation effect on the cabon-13 nuclear magnetic resonance signals of ortho-substituted phenols. II. Yakugaku Zasshi 105:140–248
15.
go back to reference Kouno I, Inoue M, Onizuka Y, Fujisaki T, Kawano N (1988) Iridoid and phenolic glucoside from Vitex rotundifolia. Phytochemistry 27:611–612CrossRef Kouno I, Inoue M, Onizuka Y, Fujisaki T, Kawano N (1988) Iridoid and phenolic glucoside from Vitex rotundifolia. Phytochemistry 27:611–612CrossRef
16.
go back to reference Kasai R, Suzuo M, Asakawa J, Tanaka O (1977) Carbon-13 chemical shifts of isoprenoid-β-d-glucopyranosides and -β-d-mannopyranosides. Stereochemical influences of aglycone alcohols. Tetrahedron Lett 1977:175–178CrossRef Kasai R, Suzuo M, Asakawa J, Tanaka O (1977) Carbon-13 chemical shifts of isoprenoid-β-d-glucopyranosides and -β-d-mannopyranosides. Stereochemical influences of aglycone alcohols. Tetrahedron Lett 1977:175–178CrossRef
17.
go back to reference Tori K, Seo S, Yoshimura Y, Arita H, Tomita Y (1977) Glycosidation shifts in carbon-13 NMR spectroscopy: carbon-13 signal shifts from aglycone and glucose to glucoside. Tetrahedron Lett 1977:179–182CrossRef Tori K, Seo S, Yoshimura Y, Arita H, Tomita Y (1977) Glycosidation shifts in carbon-13 NMR spectroscopy: carbon-13 signal shifts from aglycone and glucose to glucoside. Tetrahedron Lett 1977:179–182CrossRef
18.
go back to reference Ono M, Masuoka C, Ito Y, Nohara T (1998) Antioxidative constituents from Viticis trifoliae Fructus (fruit of Vitex rotundifolia L.). Food Sci Technol Res 4:9–13 Ono M, Masuoka C, Ito Y, Nohara T (1998) Antioxidative constituents from Viticis trifoliae Fructus (fruit of Vitex rotundifolia L.). Food Sci Technol Res 4:9–13
19.
go back to reference Yokozawa T, Chen CP, Dong E, Tanaka T, Nonaka G, Nishioka I (1998) Study on the inhibitory effect of tannins and flavonoids against the 1,1-diphenyl-2-picrylhydrazyl radical. Biochem Pharmacol 56:213–222PubMedCrossRef Yokozawa T, Chen CP, Dong E, Tanaka T, Nonaka G, Nishioka I (1998) Study on the inhibitory effect of tannins and flavonoids against the 1,1-diphenyl-2-picrylhydrazyl radical. Biochem Pharmacol 56:213–222PubMedCrossRef
20.
go back to reference Uchiyama M, Suzuki Y, Fukuzawa K (1968) Biochemical studies of physiological function of tocopheronolactone. 1. Yakugaku Zasshi 88:678–683PubMed Uchiyama M, Suzuki Y, Fukuzawa K (1968) Biochemical studies of physiological function of tocopheronolactone. 1. Yakugaku Zasshi 88:678–683PubMed
Metadata
Title
Two new lignan glucosides from the fruit of Vitex cannabifolia
Authors
Toru Yamasaki
Tetsuro Kawabata
Chikako Masuoka
Junei Kinjo
Tsuyoshi Ikeda
Toshihiro Nohara
Masateru Ono
Publication date
01-01-2008
Publisher
Springer-Verlag
Published in
Journal of Natural Medicines / Issue 1/2008
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-007-0184-1

Other articles of this Issue 1/2008

Journal of Natural Medicines 1/2008 Go to the issue