Salvileucalin B, A Novel Diterpenoid with an Unprecedented Rearranged Neoclerodane Skeleton from Salvia leucantha Cav.

被引：71

作者：

Aoyagi, Yutaka ^{[1
]}

Yamazaki, Akira ^{[1
]}

Nakatsugawa, Chihiro ^{[1
]}

Fukaya, Haruhiko ^{[1
]}

Takeya, Koichi ^{[1
]}

Kawauchi, Susumu ^{[2
]}

Izumi, Hiroshi ^{[3
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Tokyo 1920392, Japan

[2] Tokyo Inst Technol, Dept Organ & Polymer Mat, Meguro Ku, Tokyo 1528552, Japan

[3] Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058569, Japan

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 20期

关键词：

D O I：

10.1021/ol801620u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Salvileucalin B (2), having an unprecedented rearranged neoclerodane skeleton, was isolated from the aerial parts of Salvia leucantha Cav. (Labiatae) along with salvileucalin A (1). The absolute structures were elucidated by spectroscopic analysis, X-ray crystallographic analysis, and vibrational circular dichroism. Compound 2 represents a novel neoclerodane, characterized by a tricyclo[3.2.1.0(2,7)]octane substructure incorporating the exocyclic C-20 methylene of 1. This molecule exerted cytotoxic activity against A549 and HT-29 cells with IC50 values of 5.23 and 1.88 mu g/mL, respectively.

引用

页码：4429 / 4432

页数：4

共 34 条

[21] CLERODANE DITERPENOIDS [J].

MERRITT, AT ;

LEY, SV .

NATURAL PRODUCT REPORTS, 1992, 9 (03) :243-287

[22] Stereochemical studies of sialic acid derivatives by vibrational circular dichroism [J].

Nakahashi, Atsufumi ;

Taniguchi, Tohru ;

Miura, Nobuaki ;

Monde, Kenji .

ORGANIC LETTERS, 2007, 9 (23) :4741-4744

[23] A novel diterpenoid with a rearranged neoclerodane skeleton from Salvia leucantha CAV. [J].

Narukawa, Yuji ;

Hatano, Keiichiro ;

Takeda, Tadahiro .

JOURNAL OF NATURAL MEDICINES, 2006, 60 (03) :206-209

[24] Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A [J].

Nozawa, Masato ;

Suka, Yuhki ;

Hoshi, Takashi ;

Suzuki, Toshio ;

Hagiwara, Hisahiro .

ORGANIC LETTERS, 2008, 10 (07) :1365-1368

[25] Skeleton-rearranged pentacyclic diterpenoids possessing a cyclobutane ring from Euphorbia wallichii [J].

Pan, Li ;

Zhou, Ping ;

Zhang, Xiaofeng ;

Peng, Shulin ;

Ding, Lisheng ;

Qiu, Samuel X. .

ORGANIC LETTERS, 2006, 8 (13) :2775-2778

[26] The cumbiasins, structurally novel diterpenes possessing intricate carbocyclic skeletons from the West Indian sea whip Pseudopterogorgia elisabethae (Bayer) [J].

Rodríguez, AD ;

Ramírez, C ;

Shi, YP .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6682-6687

[27] Synthetic studies of neoclerodane diterpenes from Salvia divinorum:: Preparation and opioid receptor activity of salvinicin analogues [J].

Simpson, Denise S. ;

Katavic, Peter L. ;

Lozama, Anthony ;

Harding, Wayne W. ;

Parrish, Damon ;

Deschamps, Jeffrey R. ;

Dersch, Christina M. ;

Partilla, John S. ;

Rothman, Richard B. ;

Navarro, Hernan ;

Prisinzano, Thomas E. .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (15) :3596-3603

[28] Chemistry and biology of biosynthetic Diels-Alder reactions [J].

Stocking, EM ;

Williams, RM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (27) :3078-3115

[29] Diterpenoids from cultured Erythropodium caribaeorum [J].

Taglialatela-Scafati, O ;

Deo-Jangra, U ;

Campbell, M ;

Roberge, M ;

Andersen, RJ .

ORGANIC LETTERS, 2002, 4 (23) :4085-4088

[30]

Tokoroyama T, 2000, SYNTHESIS-STUTTGART, P611

← 1 2 3 4 →