Terpenic compounds which include in their structure a perhidrindanic fragment derive
biogeneticaly from a rearrangement of spongiane, kaurane, abietane and other skeletons. It
includes a ring contraction step and other oxidative degradations. Representatives of this family
are broadly found in natural sources, including both terrestrial and marine organisms. The
current communication is an overview of the most recently isolated such perhidrindanes, their
biological activity and basic synthetic routes.
Taiwaniaquinoids, have been recently reported from terrestrial natural sources [1]. These
compounds, such as taiwaniaquinone D (1), dichroanal B (2), isolated from Salvia dichroanta
[2], taiwavioquinol A (3) and standishinal (4) found in Thuja Standishi [3] possess hight level of
biological activity. Preliminary studies have revealed for many of them relevant cytotoxic
activity [4], while standishinal (4) is a potential antitumor agent.

The perhidrindanic skeleton is also present in a number of natural products isolated from
marine environment. Known examples include (+)-austrodoral (5) and (+)-austrodoric acid (6)
isolated from Antarctic nudibranch Austrodoris kerguelenensis [5], norisolide (7) and
chromodorolides A-C (8-10) isolated from Chromodoris norrisi [6]. Many moluscs are known to
harvest this kind of metabolites and use them for own defence. From the biological point of
view, these compounds are known to possess antifungal, antifeedant and antitumor activity [7].

References:
1. Majetichi, G,; Shimkus, I. M. Nat. Prod. 2010, 73, 284-298.
2. Kawazoe, K.; Yamamoto, M.; Takaishi, Y.; Honda, G.; Fujita, T.; Sezic, E.; Yesilada, E.
Phytochemistry 1999, 50, 493-497.
3. Ohtsu, H.; Ivamoto, M.; Ohishi, U.; Matsunaga, S.; Tanaka, R. Tetrahedron Lett. 1999, 40, 6419-
6422.
4. Chang, C. –I.; Chang, J.-Y.; Kuo, C. –C.; Pan, W. –Y.; Kuo, Y.-H. Planta Med. 2005, 71, 72-76.
5. Gavagnin, M.; Carbone, M.;; Mollo, E.; Cimino, G. Tetrahedron Lett. 2003, 44, 1495.
6. Hochlowski, I. E.; Faulkner, D. J.; Hatsumoto, G.K.; Clardy, J. J. Org. Chem. 1983, 48, 1141.
7. Guizzunti, G.; Brady, T. P.; Malholtra, V,; Theodorakis, E. A. J. Am. Chem. Soc. 2006, 128, 4190.