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01-01-2014 | Note

Opaciniols A–C, new terpenoids from Garcinia opaca

Authors: Reika Mori, Alfarius Eko Nugroho, Yusuke Hirasawa, Chin Piow Wong, Toshio Kaneda, Osamu Shirota, A. Hamid A. Hadi, Hiroshi Morita

Published in: Journal of Natural Medicines | Issue 1/2014

Abstract

Three new terpenoids, opaciniols A–C (1–3), were isolated from the barks of Garcinia opaca, together with malabarica-17,21-dien-3β,14-diol (4) and 13βH-malabarica-14,17,21-trien-3β-ol (5). Their structures were determined on the basis of NMR spectroscopic data. 3 and 4 showed moderate cytotoxicity against HL-60 cells.

Gustafsson MHG, Bittrich V, Stevens PF (2002) Phylogeny of Clusiaceae based on rbcL sequences. Int J Plant Sci 163:1045–1054CrossRef

Chantarasriwong O, Batova A, Chavasiri W, Theodorakis EA (2010) Chemistry and biology of the caged Garcinia xanthones. Chem Eur J 16:9944–9962PubMedCrossRef

Obolskiy D, Pischel I, Siriwatanametanon N, Heinrich M (2009) Garcinia mangostana L.: a phytochemical and pharmacological review. Phytother Res 23:1047–1065PubMedCrossRef

Klaiklay S, Sukpondma Y, Rukachaisirikul V, Phongpaichit S (2013) Friedolanostanes and xanthones from the twigs of Garcinia hombroniana. Phytochemistry 85:161–166PubMedCrossRef

Rukachaisirikul V, Saelim S, Karnsomchoke P, Phongpaichit S (2005) Friedolanostanes and lanostanes from the leaves of Garcinia hombroniana. J Nat Prod 68:1222–1225PubMedCrossRef

Vieira LMM, Kijjoa A, Wilairat R, Nascimento MSJ, Gales L, Damas AM, Silva AMS, Mondranondra I-O, Herz W (2004) Bioactive friedolanostanes and 11(10→8)-abeolanostanes from the bark of Garcinia speciosa. J Nat Prod 67:2043–2047PubMedCrossRef

Chung M-I, Su H-J, Lin C-N (1998) A novel triterpenoid of Garcinia subelliptica. J Nat Prod 61:1015–1016PubMedCrossRef

Nguyen HD, Trinh BTD, Tran QN, Nguyen HD, Pham HD, Hansen PE, Duus F, Connolly JD, Nguyen L-HD (2011) Friedolanostane, friedocycloartane and benzophenone constituents of the bark and leaves of Garcinia benthami. Phytochemistry 72:290–295PubMedCrossRef

Vieira LMM, Kijjoa A, Silva AMS, Mondranondra I-O, Kengthong S, Gales L, Damas AM, Herz W (2004) Lanostanes and friedolanostanes from the bark of Garcinia speciosa. Phytochemistry 65:393–398PubMedCrossRef

10.

Rukachaisirikul V, Adair A, Dampawan P, Taylor WC, Turner PC (2000) Lanostanes and friedolanostanes from the pericarp of Garcinia hombroniana. Phytochemistry 55:183–188PubMedCrossRef

11.

Yamasaki F, Machida S, Nakata A, Nugroho AE, Hirasawa Y, Kaneda T, Shirota O, Hagane N, Sugizaki T, Morita H (2013) Haworforbins A–C, new phenolics from Haworthia cymbiformis. J Nat Med 67:212–216PubMedCrossRef

12.

Zaima K, Deguchi J, Matsuno Y, Kaneda T, Hirasawa Y, Morita H (2013) Vasorelaxant effect of FR900359 from Ardisia crenata on rat aortic artery. J Nat Med 67:196–201PubMedCrossRef

13.

Zaima K, Koga I, Iwasawa N, Hosoya T, Hirasawa Y, Kaneda T, Ismail IS, Lajis NH, Morita H (2013) Vasorelaxant activity of indole alkaloids from Tabernaemontana dichotoma. J Nat Med 67:9–16PubMedCrossRef

14.

Deguchi J, Motegi Y, Nakata A, Hosoya T, Morita H (2013) Cyclic diarylheptanoids as inhibitors of NO production from Acer nikoense. J Nat Med 67:234–239PubMedCrossRef

15.

Nugroho AE, Hirasawa Y, Wong CP, Kaneda T, Hadi AHA, Shirota O, Ekasari W, Widyawaruyanti A, Morita H (2012) Antiplasmodial indole alkaloids from Leuconotis griffithii. J Nat Med 66:350–353PubMedCrossRef

16.

Wong CP, Shimada M, Nugroho AE, Hirasawa Y, Kaneda T, Hadi AHA, Osamu S, Morita H (2012) Ceramicines J–L, new limonoids from Chisocheton ceramicus. J Nat Med 66:566–570PubMedCrossRef

17.

Zaima K, Takeyama Y, Koga I, Saito A, Tamamoto H, Azziz SSSA, Mukhtar MP, Awang K, Hadi AHA, Morita H (2012) Vasorelaxant effect of isoquinoline derivatives from two species of Popowia perakensis and Phaeanthus crassipetalus on rat aortic artery. J Nat Med 66:421–427PubMedCrossRef

18.

Morita H, Mori R, Deguchi J, Oshimi S, Hirasawa Y, Ekasari W, Widyawaruyanti A, Hadi AHA (2012) Antiplasmodial decarboxyportentol acetate and 3,4-dehydrotheaspirone from Laumoniera bruceadelpha. J Nat Med 66:571–575PubMedCrossRef

19.

Hosoya T, Nakata A, Yamasaki F, Abas F, Shaari K, Lajis NH, Morita H (2012) Curcumin-like diarylpentanoid analogues as melanogenesis inhibitors. J Nat Med 66:166–176PubMedCrossRef

20.

Oshimi S, Zaima K, Matsuno Y, Hirasawa Y, Iizuka T, Studiawan H, Indrayanto G, Zaini NC, Morita H (2008) Studies on the constituents from the fruits of Phaleria macrocarpa. J Nat Med 62:207–210PubMedCrossRef

21.

Hoshino T, Shimizu K, Sato T (2004) Deletion of the Gly600 residue of Alicyclobacillus acidocaldarius squalene cyclase alters the substrate specificity into that of the eukaryotic-type cyclase specific to (3S)-2,3-oxidosqualene. Angew Chem 43:6700–6703CrossRef

22.

Morlacchi P, Wilson WK, Xiong Q, Bhaduri A, Sttivend D, Kolesnikova MD, Matsuda SPT (2009) Product profile of PEN3: the last unexamined oxidosqualene cyclase in Arabidopsis thaliana. Org Lett 11:2627–2630PubMedCrossRef

23.

Hasegawa S, Kaneko N, Hirose Y (1987) Triterpenes from the seed of Abies firma. Phytochemistry 26:1095–1099CrossRef

Title: Opaciniols A–C, new terpenoids from Garcinia opaca
Authors: Reika Mori
Alfarius Eko Nugroho
Yusuke Hirasawa
Chin Piow Wong
Toshio Kaneda
Osamu Shirota
A. Hamid A. Hadi
Hiroshi Morita
Publication date: 01-01-2014
Publisher: Springer Japan
Published in: Journal of Natural Medicines / Issue 1/2014
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-013-0764-1

At a glance: The STEP trials

Springer Medicine

Opaciniols A–C, new terpenoids from Garcinia opaca

Abstract

At a glance: The STEP trials

Springer Medicine

Abstract

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